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Patent Analysis of

Organic electroluminescent materials and devices

Updated Time 12 June 2019

Patent Registration Data

Publication Number

US10153443

Application Number

US15/652298

Application Date

18 July 2017

Publication Date

11 December 2018

Current Assignee

UNIVERSAL DISPLAY CORPORATION

Original Assignee (Applicant)

UNIVERSAL DISPLAY CORPORATION

International Classification

H01L51/00,C09K11/06,C07F15/00,H01L51/50

Cooperative Classification

H01L51/0085,C07F15/0033,C09K11/06,H01L51/0094,H01L51/5016

Inventor

DYATKIN, ALEXEY BORISOVICH,TSAI, JUI-YI,JI, ZHIQIANG,XIA, CHUANJUN

Patent Images

This patent contains figures and images illustrating the invention and its embodiment.

US10153443 Organic electroluminescent materials devices 1 US10153443 Organic electroluminescent materials devices 2 US10153443 Organic electroluminescent materials devices 3
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Abstract

The present invention includes novel metal complexes derived from pyridyl substituted aromatic compound core structures. These compounds can be used as emitters for PHOLEDs.

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Claims

1. A compound comprising a first ligand LA of Formula I: Formula I;

wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring; wherein RA represents from disubstitution to the possible maximum number of substitution; wherein RB represents monosubstitution to the possible maximum number of substitution, or no substitution; wherein ZA and ZB are each independently selected from the group consisting of carbon or nitrogen; wherein at least two adjacent RA are joined and fused to ring A and have the following formula: wherein A1, A2, A3, and A4 are each independently CR or N; each R can be the same or different; wherein Z1 and Z2 are each independently selected from the group consisting of O, S, Se, NR′, CR′R″, and SiR′R″; wherein the ring containing Z1 and Z2 is a non-aromatic ring; wherein R, R′, R″, RA, and RB are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any adjacent substituents are optionally joined or fused into a ring; wherein the ligand LA is coordinated to a metal M; wherein the metal M can be coordinated to other ligands; and wherein the ligand LA is optionally linked with other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand.

2. The compound of claim 1, wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

3. The compound of claim 1, wherein M is Ir or Pt.

4. The compound of claim 1, wherein each of A1, A2, A3, and A4 is independently CR.

5. The compound of claim 1, wherein ring B connects to ring A through a C—C bond.

6. The compound of claim 1, wherein Z1 and Z2 are a pair selected from the group consisting of: (O and NR′), (O and SiR′R″), (SiR′R″ and SiR′R″), (O and O), (O and CR′R″), (SiR′R″ and CR′R″), and (CR′R″ and CR′R″).

7. The compound of claim 1, wherein ZA is an sp2 neutral nitrogen atom of an N-heterocyclic ring selected from the group consisting of pyridine, pyrimidine, imidazole, benzoimidazole, pyrazole, oxazole, and triazole.

8. The compound of claim 1, wherein ZA is a neutral carbon atom of an N-heterocyclic carbene.

9. The compound of claim 1, wherein the compound has the formula M(LA)x(LB)y(LC)z;

wherein LB is a second ligand, and LC is a third ligand, and LB and LC can be the same or different; wherein x is 1, 2, or 3; wherein y is 0, 1, or 2; wherein z is 0, 1, or 2; wherein x+y+z is the oxidation state of the metal M; wherein the second ligand LB and the third ligand LC are each independently selected from the group consisting of: wherein X1 to X13 are each independently selected from the group consisting of carbon and nitrogen; wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″; wherein R′ and R″ are optionally fused or joined to form a ring; wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution; wherein R′, R″, Ra, Rb, Rc, and Rd are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or a multidentate ligand.

10. The compound of claim 9, wherein the ligand LA is selected from the group consisting of:

11. The compound of claim 10, wherein the compound has the formula Ir(LA)n(LB)3-n; wherein n is 1, 2, or 3.

12. The compound of claim 11, wherein the ligand LB is selected from the group consisting of:

LBj, j
RB1
RB2
RB3
RB4
 1.
H
H
H
H
 2.
CH3
H
H
H
 3.
H
CH3
H
H
 4.
H
H
CH3
H
 5.
H
H
H
CH3
 6.
CH3
H
CH3
H
 7.
CH3
H
H
CH3
 8.
H
CH3
CH3
H
 9.
H
CH3
H
CH3
 10.
H
H
CH3
CH3
 11.
CH3
CH3
CH3
H
 12.
CH3
CH3
H
CH3
 13.
CH3
H
CH3
CH3
 14.
H
CH3
CH3
CH3
 15.
CH3
CH3
CH3
CH3
 16.
CH2CH3
H
H
H
 17.
CH2CH3
CH3
H
H
 18.
CH2CH3
H
CH3
H
 19.
CH2CH3
H
H
CH3
 20.
CH2CH3
CH3
CH3
H
 21.
CH2CH3
CH3
H
CH3
 22.
CH2CH3
H
CH3
CH3
 23.
CH2CH3
CH3
CH3
CH3
 24.
H
CH2CH3
H
H
 25.
CH3
CH2CH3
H
H
 26.
H
CH2CH3
CH3
H
 27.
H
CH2CH3
H
CH3
 28.
CH3
CH2CH3
CH3
H
 29.
CH3
CH2CH3
H
CH3
 30.
H
CH2CH3
CH3
CH3
 31.
CH3
CH2CH3
CH3
CH3
 32.
H
H
CH2CH3
H
 33.
CH3
H
CH2CH3
H
 34.
H
CH3
CH2CH3
H
 35.
H
H
CH2CH3
CH3
 36.
CH3
CH3
CH2CH3
H
 37.
CH3
H
CH2CH3
CH3
 38.
H
CH3
CH2CH3
CH3
 39.
CH3
CH3
CH2CH3
CH3
 40.
CH(CH3)2
H
H
H
 41.
CH(CH3)2
CH3
H
H
 42.
CH(CH3)2
H
CH3
H
 43.
CH(CH3)2
H
H
CH3
 44.
CH(CH3)2
CH3
CH3
H
 45.
CH(CH3)2
CH3
H
CH3
 46.
CH(CH3)2
H
CH3
CH3
 47.
CH(CH3)2
CH3
CH3
CH3
 48.
H
CH(CH3)2
H
H
 49.
CH3
CH(CH3)2
H
H
 50.
H
CH(CH3)2
CH3
H
 51.
H
CH(CH3)2
H
CH3
 52.
CH3
CH(CH3)2
CH3
H
 53.
CH3
CH(CH3)2
H
CH3
 54.
H
CH(CH3)2
CH3
CH3
 55.
CH3
CH(CH3)2
CH3
CH3
 56.
H
H
CH(CH3)2
H
 57.
CH3
H
CH(CH3)2
H
 58.
H
CH3
CH(CH3)2
H
 59.
H
H
CH(CH3)2
CH3
 60.
CH3
CH3
CH(CH3)2
H
 61.
CH3
H
CH(CH3)2
CH3
 62.
H
CH3
CH(CH3)2
CH3
 63.
CH3
CH3
CH(CH3)2
CH3
 64.
CH2CH(CH3)2
H
H
H
 65.
CH2CH(CH3)2
CH3
H
H
 66.
CH2CH(CH3)2
H
CH3
H
 67.
CH2CH(CH3)2
H
H
CH3
 68.
CH2CH(CH3)2
CH3
CH3
H
 69.
CH2CH(CH3)2
CH3
H
CH3
 70.
CH2CH(CH3)2
H
CH3
CH3
 71.
CH2CH(CH3)2
CH3
CH3
CH3
 72.
H
CH2CH(CH3)2
H
H
 73.
CH3
CH2CH(CH3)2
H
H
 74.
H
CH2CH(CH3)2
CH3
H
 75.
H
CH2CH(CH3)2
H
CH3
 76.
CH3
CH2CH(CH3)2
CH3
H
 77.
CH3
CH2CH(CH3)2
H
CH3
 78.
H
CH2CH(CH3)2
CH3
CH3
 79.
CH3
CH2CH(CH3)2
CH3
CH3
 80.
H
H
CH2CH(CH3)2
H
 81.
CH3
H
CH2CH(CH3)2
H
 82.
H
CH3
CH2CH(CH3)2
H
 83.
H
H
CH2CH(CH3)2
CH3
 84.
CH3
CH3
CH2CH(CH3)2
H
 85.
CH3
H
CH2CH(CH3)2
CH3
 86.
H
CH3
CH2CH(CH3)2
CH3
 87.
CH3
CH3
CH2CH(CH3)2
CH3
 88.
C(CH3)3
H
H
H
 89.
C(CH3)3
CH3
H
H
 90.
C(CH3)3
H
CH3
H
 91.
C(CH3)3
H
H
CH3
 92.
C(CH3)3
CH3
CH3
H
 93.
C(CH3)3
CH3
H
CH3
 94.
C(CH3)3
H
CH3
CH3
 95.
C(CH3)3
CH3
CH3
CH3
 96.
H
C(CH3)3
H
H
 97.
CH3
C(CH3)3
H
H
 98.
H
C(CH3)3
CH3
H
 99.
H
C(CH3)3
H
CH3
100.
CH3
C(CH3)3
CH3
H
101.
CH3
C(CH3)3
H
CH3
102.
H
C(CH3)3
CH3
CH3
103.
CH3
C(CH3)3
CH3
CH3
104.
H
H
C(CH3)3
H
105.
CH3
H
C(CH3)3
H
106.
H
CH3
C(CH3)3
H
107.
H
H
C(CH3)3
CH3
108.
CH3
CH3
C(CH3)3
H
109.
CH3
H
C(CH3)3
CH3
110.
H
CH3
C(CH3)3
CH3
111.
CH3
CH3
C(CH3)3
CH3
112.
CH2C(CH3)3
H
H
H
113.
CH2C(CH3)3
CH3
H
H
114.
CH2C(CH3)3
H
CH3
H
115.
CH2C(CH3)3
H
H
CH3
116.
CH2C(CH3)3
CH3
CH3
H
117.
CH2C(CH3)3
CH3
H
CH3
118.
CH2C(CH3)3
H
CH3
CH3
119.
CH2C(CH3)3
CH3
CH3
CH3
120.
H
CH2C(CH3)3
H
H
121.
CH3
CH2C(CH3)3
H
H
122.
H
CH2C(CH3)3
CH3
H
123.
H
CH2C(CH3)3
H
CH3
124.
CH3
CH2C(CH3)3
CH3
H
125.
CH3
CH2C(CH3)3
H
CH3
126.
H
CH2C(CH3)3
CH3
CH3
127.
CH3
CH2C(CH3)3
CH3
CH3
128.
H
H
CH2C(CH3)3
H
129.
CH3
H
CH2C(CH3)3
H
130.
H
CH3
CH2C(CH3)3
H
131.
H
H
CH2C(CH3)3
CH3
132.
CH3
CH3
CH2C(CH3)3
H
133.
CH3
H
CH2C(CH3)3
CH3
134.
H
CH3
CH2C(CH3)3
CH3
135.
CH3
CH3
CH2C(CH3)3
CH3
136.
CH2C(CH3)2CF3
H
H
H
137.
CH2C(CH3)2CF3
CH3
H
H
138.
CH2C(CH3)2CF3
H
CH3
H
139.
CH2C(CH3)2CF3
H
H
CH3
140.
CH2C(CH3)2CF3
CH3
CH3
H
141.
CH2C(CH3)2CF3
CH3
H
CH3
142.
CH2C(CH3)2CF3
H
CH3
CH3
143.
CH2C(CH3)2CF3
CH3
CH3
CH3
144.
H
CH2C(CH3)2CF3
H
H
145.
CH3
CH2C(CH3)2CF3
H
H
146.
H
CH2C(CH3)2CF3
CH3
H
147.
H
CH2C(CH3)2CF3
H
CH3
148.
CH3
CH2C(CH3)2CF3
CH3
H
149.
CH3
CH2C(CH3)2CF3
H
CH3
150.
H
CH2C(CH3)2CF3
CH3
CH3
151.
CH3
CH2C(CH3)2CF3
CH3
CH3
152.
H
H
CH2C(CH3)2CF3
H
153.
CH3
H
CH2C(CH3)2CF3
H
154.
H
CH3
CH2C(CH3)2CF3
H
155.
H
H
CH2C(CH3)2CF3
CH3
156.
CH3
CH3
CH2C(CH3)2CF3
H
157.
CH3
H
CH2C(CH3)2CF3
CH3
158.
H
CH3
CH2C(CH3)2CF3
CH3
159.
CH3
CH3
CH2C(CH3)2CF3
CH3
160.
CH2CH2CF3
H
H
H
161.
CH2CH2CF3
CH3
H
H
162.
CH2CH2CF3
H
CH3
H
163.
CH2CH2CF3
H
H
CH3
164.
CH2CH2CF3
CH3
CH3
H
165.
CH2CH2CF3
CH3
H
CH3
166.
CH2CH2CF3
H
CH3
CH3
167.
CH2CH2CF3
CH3
CH3
CH3
168.
H
CH2CH2CF3
H
H
169.
CH3
CH2CH2CF3
H
H
170.
H
CH2CH2CF3
CH3
H
171.
H
CH2CH2CF3
H
CH3
172.
CH3
CH2CH2CF3
CH3
H
173.
CH3
CH2CH2CF3
H
CH3
174.
H
CH2CH2CF3
CH3
CH3
175.
CH3
CH2CH2CF3
CH3
CH3
176.
H
H
CH2CH2CF3
H
177.
CH3
H
CH2CH2CF3
H
178.
H
CH3
CH2CH2CF3
H
179.
H
H
CH2CH2CF3
CH3
180.
CH3
CH3
CH2CH2CF3
H
181.
CH3
H
CH2CH2CF3
CH3
182.
H
CH3
CH2CH2CF3
CH3
183.
CH3
CH3
CH2CH2CF3
CH3
184.
H
H
H
185.
CH3
H
H
186.
H
CH3
H
187.
H
H
CH3
188.
CH3
CH3
H
189.
CH3
H
CH3
190.
H
CH3
CH3
191.
CH3
CH3
CH3
192.
H
H
H
193.
CH3
H
H
194.
H
CH3
H
195.
H
H
CH3
196.
CH3
CH3
H
197.
CH3
H
CH3
198.
H
CH3
CH3
199.
CH3
CH3
CH3
200.
H
H
H
201.
CH3
H
H
202.
H
CH3
H
203.
H
H
CH3
204.
CH3
CH3
H
205.
CH3
H
CH3
206.
H
CH3
CH3
207.
CH3
CH3
CH3
208.
H
H
H
209.
CH3
H
H
210.
H
CH3
H
211.
H
H
CH3
212.
CH3
CH3
H
213.
CH3
H
CH3
214.
H
CH3
CH3
215.
CH3
CH3
CH3
216.
H
H
H
217.
CH3
H
H
218.
H
CH3
H
219.
H
H
CH3
220.
CH3
CH3
H
221.
CH3
H
CH3
222.
H
CH3
CH3
223.
CH3
CH3
CH3
224.
H
H
H
225.
CH3
H
H
226.
H
CH3
H
227.
H
H
CH3
228.
CH3
CH3
H
229.
CH3
H
CH3
230.
H
CH3
CH3
231.
CH3
CH3
CH3
232.
H
H
H
233.
CH3
H
H
234.
H
CH3
H
235.
H
H
CH3
236.
CH3
CH3
H
237.
CH3
H
CH3
238.
H
CH3
CH3
239.
CH3
CH3
CH3
240.
H
H
H
241.
CH3
H
H
242.
H
CH3
H
243.
H
H
CH3
244.
CH3
CH3
H
245.
CH3
H
CH3
246.
H
CH3
CH3
247.
CH3
CH3
CH3
248.
H
H
H
249.
CH3
H
H
250.
H
CH3
H
251.
H
H
CH3
252.
CH3
CH3
H
253.
CH3
H
CH3
254.
H
CH3
CH3
255.
CH3
CH3
CH3
256.
H
H
H
257.
CH3
H
H
258.
H
CH3
H
259.
H
H
CH3
260.
CH3
CH3
H
261.
CH3
H
CH3
262.
H
CH3
CH3
263.
CH3
CH3
CH3
264.
H
H
H
265.
CH3
H
H
266.
H
CH3
H
267.
H
H
CH3
268.
CH3
CH3
H
269.
CH3
H
CH3
270.
H
CH3
CH3
271.
CH3
CH3
CH3
272.
H
H
H
273.
CH3
H
H
274.
H
CH3
H
275.
H
H
CH3
276.
CH3
CH3
H
277.
CH3
H
CH3
278.
H
CH3
CH3
279.
CH3
CH3
CH3
280.
H
H
H
281.
CH3
H
H
282.
H
CH3
H
283.
H
H
CH3
284.
CH3
CH3
H
285.
CH3
H
CH3
286.
H
CH3
CH3
287.
CH3
CH3
CH3
288.
H
H
H
289.
CH3
H
H
290.
H
CH3
H
291.
H
H
CH3
292.
CH3
CH3
H
293.
CH3
H
CH3
294.
H
CH3
CH3
295.
CH3
CH3
CH3
296.
H
H
H
297.
CH3
H
H
298.
H
CH3
H
299.
H
H
CH3
300.
CH3
CH3
H
301.
CH3
H
CH3
302.
H
CH3
CH3
303.
CH3
CH3
CH3
304.
H
H
H
305.
CH3
H
H
306.
H
CH3
H
307.
H
H
CH3
308.
CH3
CH3
H
309.
CH3
H
CH3
310.
H
CH3
CH3
311.
CH3
CH3
CH3
312.
H
H
H
313.
CH3
H
H
314.
H
CH3
H
315.
H
H
CH3
316.
CH3
CH3
H
317.
CH3
H
CH3
318.
H
CH3
CH3
319.
CH3
CH3
CH3
320.
H
H
H
321.
CH3
H
H
322.
H
CH3
H
323.
H
H
CH3
324.
CH3
CH3
H
325.
CH3
H
CH3
326.
H
CH3
CH3
327.
CH3
CH3
CH3
328.
CH(CH3)2
H
CH2CH3
H
329.
CH(CH3)2
H
CH(CH3)2
H
330.
CH(CH3)2
H
CH2CH(CH3)2
H
331.
CH(CH3)2
H
C(CH3)3
H
332.
CH(CH3)2
H
CH2C(CH3)3
H
333.
CH(CH3)2
H
CH2CH2CF3
H
334.
CH(CH3)2
H
CH2C(CH3)2CF3
H
335.
CH(CH3)2
H
H
336.
CH(CH3)2
H
H
337.
CH(CH3)2
H
H
338.
CH(CH3)2
H
H
339.
CH(CH3)2
H
H
340.
CH(CH3)2
H
H
341.
C(CH3)3
H
CH2CH3
H
342.
C(CH3)3
H
CH(CH3)2
H
343.
C(CH3)3
H
CH2CH(CH3)2
H
344.
C(CH3)3
H
C(CH3)3
H
345.
C(CH3)3
H
CH2C(CH3)3
H
346.
C(CH3)3
H
CH2CH2CF3
H
347.
C(CH3)3
H
CH2C(CH3)2CF3
H
348.
C(CH3)3
H
H
349.
C(CH3)3
H
H
350.
C(CH3)3
H
H
351.
C(CH3)3
H
H
352.
C(CH3)3
H
H
353.
C(CH3)3
H
H
354.
CH2C(CH3)3
H
CH2CH3
H
355.
CH2C(CH3)3
H
CH(CH3)2
H
356.
CH2C(CH3)3
H
CH2CH(CH3)2
H
357.
CH2C(CH3)3
H
C(CH3)3
H
358.
CH2C(CH3)3
H
CH2C(CH3)3
H
359.
CH2C(CH3)3
H
CH2CH2CF3
H
360.
CH2C(CH3)3
H
CH2C(CH3)2CF3
H
361.
CH2C(CH3)3
H
H
362.
CH2C(CH3)3
H
H
363.
CH2C(CH3)3
H
H
364.
CH2C(CH3)3
H
H
365.
CH2C(CH3)3
H
H
366.
CH2C(CH3)3
H
H
367.
H
CH2CH3
H
368.
H
CH(CH3)2
H
369.
H
CH2CH(CH3)2
H
370.
H
C(CH3)3
H
371.
H
CH2C(CH3)3
H
372.
H
CH2CH2CF3
H
373.
H
CH2C(CH3)2CF3
H
374.
H
H
375.
H
H
376.
H
H
377.
H
H
378.
H
H
379.
H
H
380.
H
CH2CH3
H
381.
H
CH(CH3)2
H
382.
H
CH2CH(CH3)2
H
383.
H
C(CH3)3
H
384.
H
CH2C(CH3)3
H
385.
H
CH2CH2CF3
H
386.
H
CH2C(CH3)2CF3
H
387.
H
H
388.
H
H
389.
H
H
390.
H
H
391.
H
H
392.
H
H
393.
H
CH2CH(CH3)2
H
394.
H
C(CH3)3
H
395.
H
CH2C(CH3)3
H
396.
H
CH2CH2CF3
H
397.
H
CH2C(CH3)2CF3
H
398.
H
H
399.
H
H
400.
H
H
401.
H
H
402.
H
H
403.
H
H
404.
H
CH2CH(CH3)2
H
405.
H
C(CH3)3
H
406.
H
CH2C(CH3)3
H
407.
H
CH2CH2CF3
H
408.
H
CH2C(CH3)2CF3
H
409.
H
H
410.
H
H
411.
H
H
412.
H
H
413.
H
H
414.
H
H
415.
H
CH2CH(CH3)2
H
416.
H
C(CH3)3
H
417.
H
CH2C(CH3)3
H
418.
H
CH2CH2CF3
H
419.
H
CH2C(CH3)2CF3
H
420.
H
H
421.
H
H
422.
H
H
423.
H
H
424.
H
H
425.
H
H
426.
CD3
H
H
H
427.
H
CD3
H
H
428.
H
H
CD3
H
429.
H
H
H
CD3
430.
CD3
H
CD3
H
431.
CD3
H
H
CD3
432.
H
CD3
CD3
H
433.
H
CD3
H
CD3
434.
H
H
CD3
CD3
435.
CD3
CD3
CD3
H
436.
CD3
CD3
H
CD3
437.
CD3
H
CD3
CD3
438.
H
CD3
CD3
CD3
439.
CD3
CD3
CD3
CD3
440.
CD2CH3
H
H
H
441.
CD2CH3
CD3
H
H
442.
CD2CH3
H
CD3
H
443.
CD2CH3
H
H
CD3
444.
CD2CH3
CD3
CD3
H
445.
CD2CH3
CD3
H
CD3
446.
CD2CH3
H
CD3
CD3
447.
CD2CH3
CD3
CD3
CD3
448.
H
CD2CH3
H
H
449.
CD3
CD2CH3
H
H
450.
H
CD2CH3
CD3
H
451.
H
CD2CH3
H
CD3
452.
CD3
CD2CH3
CD3
H
453.
CD3
CD2CH3
H
CD3
454.
H
CD2CH3
CD3
CD3
455.
CD3
CD2CH3
CD3
CD3
456.
H
H
CD2CH3
H
457.
CD3
H
CD2CH3
H
458.
H
CD3
CD2CH3
H
459.
H
H
CD2CH3
CD3
460.
CD3
CD3
CD2CH3
H
461.
CD3
H
CD2CH3
CD3
462.
H
CD3
CD2CH3
CD3
463.
CD3
CD3
CD2CH3
CD3
464.
CD(CH3)2
H
H
H
465.
CD(CH3)2
CD3
H
H
466.
CD(CH3)2
H
CD3
H
467.
CD(CH3)2
H
H
CD3
468.
CD(CH3)2
CD3
CD3
H
469.
CD(CH3)2
CD3
H
CD3
470.
CD(CH3)2
H
CD3
CD3
471.
CD(CH3)2
CD3
CD3
CD3
472.
H
CD(CH3)2
H
H
473.
CD3
CD(CH3)2
H
H
474.
H
CD(CH3)2
CD3
H
475.
H
CD(CH3)2
H
CD3
476.
CD3
CD(CH3)2
CD3
H
477.
CD3
CD(CH3)2
H
CD3
478.
H
CD(CH3)2
CD3
CD3
479.
CD3
CD(CH3)2
CD3
CD3
480.
H
H
CD(CH3)2
H
481.
CD3
H
CD(CH3)2
H
482.
H
CD3
CD(CH3)2
H
483.
H
H
CD(CH3)2
CD3
484.
CD3
CD3
CD(CH3)2
H
485.
CD3
H
CD(CH3)2
CD3
486.
H
CD3
CD(CH3)2
CD3
487.
CD3
CD3
CD(CH3)2
CD3
488.
CD(CD3)2
H
H
H
489.
CD(CD3)2
CD3
H
H
490.
CD(CD3)2
H
CD3
H
491.
CD(CD3)2
H
H
CD3
492.
CD(CD3)2
CD3
CD3
H
493.
CD(CD3)2
CD3
H
CD3
494.
CD(CD3)2
H
CD3
CD3
495.
CD(CD3)2
CD3
CD3
CD3
496.
H
CD(CD3)2
H
H
497.
CD3
CD(CD3)2
H
H
498.
H
CD(CD3)2
CD3
H
499.
H
CD(CD3)2
H
CD3
500.
CD3
CD(CD3)2
CD3
H
501.
CD3
CD(CD3)2
H
CD3
502.
H
CD(CD3)2
CD3
CD3
503.
CD3
CD(CD3)2
CD3
CD3
504.
H
H
CD(CD3)2
H
505.
CD3
H
CD(CD3)2
H
506.
H
CD3
CD(CD3)2
H
507.
H
H
CD(CD3)2
CD3
508.
CD3
CD3
CD(CD3)2
H
509.
CD3
H
CD(CD3)2
CD3
510.
H
CD3
CD(CD3)2
CD3
511.
CD3
CD3
CD(CD3)2
CD3
512.
CD2CH(CH3)2
H
H
H
513.
CD2CH(CH3)2
CD3
H
H
514.
CD2CH(CH3)2
H
CD3
H
515.
CD2CH(CH3)2
H
H
CD3
516.
CD2CH(CH3)2
CD3
CD3
H
517.
CD2CH(CH3)2
CD3
H
CD3
518.
CD2CH(CH3)2
H
CD3
CD3
519.
CD2CH(CH3)2
CD3
CD3
CD3
520.
H
CD2CH(CH3)2
H
H
521.
CD3
CD2CH(CH3)2
H
H
522.
H
CD2CH(CH3)2
CD3
H
523.
H
CD2CH(CH3)2
H
CD3
524.
CD3
CD2CH(CH3)2
CD3
H
525.
CD3
CD2CH(CH3)2
H
CD3
526.
H
CD2CH(CH3)2
CD3
CD3
527.
CD3
CD2CH(CH3)2
CD3
CD3
528.
H
H
CD2CH(CH3)2
H
529.
CD3
H
CD2CH(CH3)2
H
530.
H
CD3
CD2CH(CH3)2
H
531.
H
H
CD2CH(CH3)2
CD3
532.
CD3
CD3
CD2CH(CH3)2
H
533.
CD3
H
CD2CH(CH3)2
CD3
534.
H
CD3
CD2CH(CH3)2
CD3
535.
CD3
CD3
CD2CH(CH3)2
CD3
536.
CD2C(CH3)3
H
H
H
537.
CD2C(CH3)3
CD3
H
H
538.
CD2C(CH3)3
H
CD3
H
539.
CD2C(CH3)3
H
H
CD3
540.
CD2C(CH3)3
CD3
CD3
H
541.
CD2C(CH3)3
CD3
H
CD3
542.
CD2C(CH3)3
H
CD3
CD3
543.
CD2C(CH3)3
CH3
CD3
CD3
544.
H
CD2C(CH3)3
H
H
545.
CD3
CD2C(CH3)3
H
H
546.
H
CD2C(CH3)3
CD3
H
547.
H
CD2C(CH3)3
H
CD3
548.
CD3
CD2C(CH3)3
CD3
H
549.
CD3
CD2C(CH3)3
H
CD3
550.
H
CD2C(CH3)3
CD3
CD3
551.
CD3
CD2C(CH3)3
CD3
CD3
552.
H
H
CD2C(CH3)3
H
553.
CD3
H
CD2C(CH3)3
H
554.
H
CD3
CD2C(CH3)3
H
555.
H
H
CD2C(CH3)3
CD3
556.
CD3
CD3
CD2C(CH3)3
H
557.
CD3
H
CD2C(CH3)3
CD3
558.
H
CD3
CD2C(CH3)3
CD3
559.
CD3
CD3
CD2C(CH3)3
CD3
560.
CD2C(CH3)2CF3
H
H
H
561.
CD2C(CH3)2CF3
CD3
H
H
562.
CD2C(CH3)2CF3
H
CD3
H
563.
CD2C(CH3)2CF3
H
H
CD3
564.
CD2C(CH3)2CF3
CD3
CD3
H
565.
CD2C(CH3)2CF3
CD3
H
CD3
566.
CD2C(CH3)2CF3
H
CD3
CD3
567.
CD2C(CH3)2CF3
CD3
CD3
CD3
568.
H
CD2C(CH3)2CF3
H
H
569.
CD3
CD2C(CH3)2CF3
H
H
570.
H
CD2C(CH3)2CF3
CD3
H
571.
H
CD2C(CH3)2CF3
H
CD3
572.
CD3
CD2C(CH3)2CF3
CD3
H
573.
CD3
CD2C(CH3)2CF3
H
CD3
574.
H
CD2C(CH3)2CF3
CD3
CD3
575.
CD3
CD2C(CH3)2CF3
CD3
CD3
576.
H
H
CD2C(CH3)2CF3
H
577.
CD3
H
CD2C(CH3)2CF3
H
578.
H
CD3
CD2C(CH3)2CF3
H
579.
H
H
CD2C(CH3)2CF3
CD3
580.
CD3
CD3
CD2C(CH3)2CF3
H
581.
CD3
H
CD2C(CH3)2CF3
CD3
582.
H
CD3
CD2C(CH3)2CF3
CD3
583.
CD3
CD3
CD2C(CH3)2CF3
CD3
584.
CD2CH2CF3
H
H
H
585.
CD2CH2CF3
CD3
H
H
586.
CD2CH2CF3
H
CD3
H
587.
CD2CH2CF3
H
H
CD3
588.
CD2CH2CF3
CD3
CD3
H
589.
CD2CH2CF3
CD3
H
CD3
590.
CD2CH2CF3
H
CD3
CD3
591.
CD2CH2CF3
CD3
CD3
CD3
592.
H
CD2CH2CF3
H
H
593.
CD3
CD2CH2CF3
H
H
594.
H
CD2CH2CF3
CD3
H
595.
H
CD2CH2CF3
H
CD3
596.
CD3
CD2CH2CF3
CD3
H
597.
CD3
CD2CH2CF3
H
CD3
598.
H
CD2CH2CF3
CD3
CD3
599.
CD3
CD2CH2CF3
CD3
CD3
600.
H
H
CD2CH2CF3
H
601.
CD3
H
CD2CH2CF3
H
602.
H
CD3
CD2CH2CF3
H
603.
H
H
CD2CH2CF3
CD3
604.
CD3
CD3
CD2CH2CF3
H
605.
CD3
H
CD2CH2CF3
CD3
606.
H
CD3
CD2CH2CF3
CD3
607.
CD3
CD3
CD2CH2CF3
CD3
608.
H
H
H
609.
CD3
H
H
610.
H
CD3
H
611.
H
H
CD3
612.
CD3
CD3
H
613.
CD3
H
CD3
614.
H
CD3
CD3
615.
CD3
CD3
CD3
616.
H
H
H
617.
CD3
H
H
618.
H
CD3
H
619.
H
H
CD3
620.
CD3
CD3
H
621.
CD3
H
CD3
622.
H
CD3
CD3
623.
CD3
CD3
CD3
624.
H
H
H
625.
CD3
H
H
626.
H
CD3
H
627.
H
H
CD3
628.
CD3
CD3
H
629.
CD3
H
CD3
630.
H
CD3
CD3
631.
CD3
CD3
CD3
632.
H
H
H
633.
CD3
H
H
634.
H
CD3
H
635.
H
H
CD3
636.
CD3
CD3
H
637.
CD3
H
CD3
638.
H
CD3
CD3
639.
CD3
CD3
CD3
640.
H
H
H
641.
CD3
H
H
642.
H
CD3
H
643.
H
H
CD3
644.
CD3
CD3
H
645.
CD3
H
CD3
646.
H
CD3
CD3
647.
CH3
CD3
CD3
648.
H
H
H
649.
CD3
H
H
650.
H
CD3
H
651.
H
H
CD3
652.
CD3
CD3
H
653.
CD3
H
CD3
654.
H
CD3
CD3
655.
CD3
CD3
CD3
656.
H
H
H
657.
CD3
H
H
658.
H
CD3
H
659.
H
H
CD3
660.
CD3
CD3
H
661.
CD3
H
CD3
662.
H
CD3
CD3
663.
CD3
CD3
CD3
664.
H
H
H
665.
CD3
H
H
666.
H
CD3
H
667.
H
H
CD3
668.
CD3
CD3
H
669.
CD3
H
CD3
670.
H
CD3
CD3
671.
CD3
CD3
CD3
672.
H
H
H
673.
CD3
H
H
674.
H
CD3
H
675.
H
H
CD3
676.
CD3
CD3
H
677.
CD3
H
CD3
678.
H
CD3
CD3
679.
CD3
CD3
CD3
680.
H
H
H
681.
CD3
H
H
682.
H
CD3
H
683.
H
H
CD3
684.
CD3
CD3
H
685.
CD3
H
CD3
686.
H
CD3
CD3
687.
CD3
CD3
CD3
688.
H
H
H
689.
CD3
H
H
690.
H
CD3
H
691.
H
H
CD3
692.
CD3
CD3
H
693.
CD3
H
CD3
694.
H
CD3
CD3
695.
CD3
CD3
CD3
696.
H
H
H
697.
CD3
H
H
698.
H
CD3
H
699.
H
H
CD3
700.
CD3
CD3
H
701.
CD3
H
CD3
702.
H
CD3
CD3
703.
CD3
CD3
CD3
704.
H
H
H
705.
CD3
H
H
706.
H
CD3
H
707.
H
H
CD3
708.
CD3
CD3
H
709.
CD3
H
CD3
710.
H
CD3
CD3
711.
CD3
CD3
CD3
712.
H
H
H
713.
CD3
H
H
714.
H
CD3
H
715.
H
H
CD3
716.
CD3
CD3
H
717.
CD3
H
CD3
718.
H
CD3
CD3
719.
CD3
CD3
CD3
720.
H
H
H
721.
CD3
H
H
722.
H
CD3
H
723.
H
H
CD3
724.
CD3
CD3
H
725.
CD3
H
CD3
726.
H
CD3
CD3
727.
CD3
CD3
CD3
728.
H
H
H
729.
CD3
H
H
730.
H
CD3
H
731.
H
H
CD3
732.
CH3
CH3
H
733.
CD3
H
CD3
734.
H
CD3
CD3
735.
CD3
CD3
CD3
736.
H
H
H
737.
CD3
H
H
738.
H
CD3
H
739.
H
H
CD3
740.
CD3
CD3
H
741.
CD3
H
CD3
742.
H
CD3
CD3
743.
CD3
CD3
CD3
744.
H
H
H
745.
CD3
H
H
746.
H
CD3
H
747.
H
H
CD3
748.
CD3
CD3
H
749.
CD3
H
CD3
750.
H
CD3
CD3
751.
CD3
CD3
CD3
752.
CD(CH3)2
H
CD2CH3
H
753.
CD(CH3)2
H
CD(CD3)2
H
754.
CD(CH3)2
H
CD2CH(CH3)2
H
755.
CD(CH3)2
H
C(CH3)3
H
756.
CD(CH3)2
H
CD2C(CH3)3
H
757.
CD(CH3)2
H
CD2CH2CF3
H
758.
CD(CH3)2
H
CD2C(CH3)2CF3
H
759.
CD(CH3)2
H
H
760.
CD(CH3)2
H
H
761.
CD(CH3)2
H
H
762.
CD(CH3)2
H
H
763.
CD(CH3)2
H
H
764.
CD(CH3)2
H
H
765.
C(CH3)3
H
CD2CH3
H
766.
C(CH3)3
H
CD(CD3)2
H
767.
C(CH3)3
H
CD2CH(CH3)2
H
768.
C(CH3)3
H
CD2C(CH3)3
H
769.
C(CH3)3
H
CD2CH2CF3
H
770.
C(CH3)3
H
CD2C(CH3)2CF3
H
771.
C(CH3)3
H
H
772.
C(CH3)3
H
H
773.
C(CH3)3
H
H
774.
C(CH3)3
H
H
775.
C(CH3)3
H
H
776.
C(CH3)3
H
H
777.
CD2C(CH3)3
H
CD2CH3
H
778.
CD2C(CH3)3
H
CD(CD3)2
H
779.
CD2C(CH3)3
H
CD2CH(CH3)2
H
780.
CD2C(CH3)3
H
C(CH3)3
H
781.
CD2C(CH3)3
H
CD2C(CH3)3
H
782.
CD2C(CH3)3
H
CD2CH2CF3
H
783.
CD2C(CH3)3
H
CD2C(CH3)2CF3
H
784.
CD2C(CH3)3
H
H
785.
CD2C(CH3)3
H
H
786.
CD2C(CH3)3
H
H
787.
CD2C(CH3)3
H
H
788.
CD2C(CH3)3
H
H
789.
CD2C(CH3)3
H
H
790.
H
CD2CH3
H
791.
H
CD(CD3)2
H
792.
H
CD2CH(CH3)2
H
793.
H
C(CH3)3
H
794.
H
CD2C(CH3)3
H
795.
H
CD2CH2CF3
H
796.
H
CD2C(CH3)2CF3
H
797.
H
H
798.
H
H
799.
H
H
800.
H
H
801.
H
H
802.
H
H
803.
H
CD2CH3
H
804.
H
CD(CD3)2
H
805.
H
CD2CH(CH3)2
H
806.
H
C(CH3)3
H
807.
H
CD2C(CH3)3
H
808.
H
CD2CH2CF3
H
809.
H
CD2C(CH3)2CF3
H
810.
H
H
811.
H
H
812.
H
H
813.
H
H
814.
H
H
815.
H
H
816.
H
CD2CH3
H
817.
H
CD(CD3)2
H
818.
H
CD2CH(CH3)2
H
819.
H
C(CH3)3
H
820.
H
CD2C(CH3)3
H
821.
H
CD2CH2CF3
H
822.
H
CD2C(CH3)2CF3
H
823.
H
H
824.
H
H
825.
H
H
826.
H
H
827.
H
H
828.
H
H
829.
H
CD2CH3
H
830.
H
CD(CD3)2
H
831.
H
CD2CH(CH3)2
H
832.
H
C(CH3)3
H
833.
H
CD2C(CH3)3
H
834.
H
CD2CH2CF3
H
835.
H
CD2C(CH3)2CF3
H
836.
H
H
837.
H
H
838.
H
H
839.
H
H
840.
H
H
841.
H
H
842.
H
CD2CH3
H
843.
H
CD(CD3)2
H
844.
H
CD2CH(CH3)2
H
845.
H
C(CH3)3
H
846.
H
CD2C(CH3)3
H
847.
H
CD2CH2CF3
H
848.
H
CD2C(CH3)2CF3
H
849.
H
H
850.
H
H
851.
H
H
852.
H
H
853.
H
H
854.
H
H.

13. The compound of claim 12, wherein the compound is the Compound x having the formula Ir(LAi)(LBj)2;

wherein x=854t+j−854; i is an integer from 1 to 368, and j is an integer from 1 to 854.

14. An organic light-emitting device (OLED) comprising:

an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a compound comprising a first ligand LA of Formula I: Formula I;

wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring; wherein RA represents from disubstitution to the possible maximum number of substitution; wherein RB represents monosubstitution to the possible maximum number of substitution, or no substitution; wherein ZA and ZB are each independently selected from the group consisting of carbon or nitrogen; wherein at least two adjacent RA are joined and fused to ring A and have the following formula: wherein A1, A2, A3, and A4 are each independently CR or N; each R can be the same or different; wherein Z1 and Z2 are each independently selected from the group consisting of O, S, Se, NR′, CR′R″, and SiR′R″; wherein the ring containing Z1 and Z2 is a non-aromatic ring; wherein R, R′, R″, RA, and RB are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any adjacent substituents are optionally joined or fused into a ring; wherein the ligand LA is coordinated to a metal M; wherein the metal M can be coordinated to other ligands; and wherein the ligand LA is optionally linked with other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand.

15. The OLED of claim 14, wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

16. The OLED of claim 14, wherein the organic layer further comprises a host, wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host is an unfused substituent independently selected from the group consisting of CnH2n+1, OCnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH═CH—CnH2n+1, C≡CCnH2n+1, Ar1, Ar1-Ar2, CnH2n—Ar1, or no substitution;

wherein n is from 1 to 10; and wherein Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

17. The OLED of claim 14, wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

18. The OLED of claim 14, wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of: and combinations thereof.

19. A consumer product comprising an organic light-emitting device (OLED) comprising:

an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a compound comprising a first ligand LA of Formula I: Formula I;

wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring; wherein RA represents from disubstitution to the possible maximum number of substitution; wherein RB represents monosubstitution to the possible maximum number of substitution, or no substitution; wherein ZA and ZB are each independently selected from the group consisting of carbon or nitrogen; wherein at least two adjacent RA are joined and fused to ring A and have the following formula: wherein A1, A2, A3, and A4 are each independently CR or N; each R can be the same or different; wherein Z1 and Z2 are each independently selected from the group consisting of O, S, Se, NR′, CR′R″, and SiR′R″; wherein the ring containing Z1 and Z2 is a non-aromatic ring; wherein R, R′, R″, RA, and RB are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any adjacent substituents are optionally joined or fused into a ring; wherein the ligand LA is coordinated to a metal M; wherein the metal M can be coordinated to other ligands; and wherein the ligand LA is optionally linked with other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand.

20. The consumer product of claim 19, wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, and a sign.

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Claim Tree

  • 1
    1. A compound comprising
    • a first ligand LA of Formula I: Formula I
    • wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring
    • wherein RA represents from disubstitution to the possible maximum number of substitution
    • wherein RB represents monosubstitution to the possible maximum number of substitution, or no substitution
    • wherein ZA and ZB are each independently selected from the group consisting of carbon or nitrogen
    • wherein at least two adjacent RA are joined and fused to ring A and have the following formula: wherein A1, A2, A3, and A4 are each independently CR or N
    • each R can be the same or different
    • wherein Z1 and Z2 are each independently selected from the group consisting of O, S, Se, NR′, CR′R″, and SiR′R″
    • wherein the ring containing Z1 and Z2 is a non-aromatic ring
    • wherein R, R′, R″, RA, and RB are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof
    • wherein any adjacent substituents are optionally joined or fused into a ring
    • wherein the ligand LA is coordinated to a metal M
    • wherein the metal M can be coordinated to other ligands
    • and wherein the ligand LA is optionally linked with other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand.
    • 2. The compound of claim 1, wherein
      • M is selected from the group consisting of
    • 3. The compound of claim 1, wherein
      • M is Ir or Pt.
    • 4. The compound of claim 1, wherein
      • each of A1, A2, A3, and A4 is independently CR.
    • 5. The compound of claim 1, wherein
      • ring B connects to ring A through a C—C bond.
    • 6. The compound of claim 1, wherein
      • Z1 and Z2 are a pair selected from the group consisting of:
    • 7. The compound of claim 1, wherein
      • ZA is an sp2 neutral nitrogen atom of an N-heterocyclic ring selected from the group consisting of
    • 8. The compound of claim 1, wherein
      • ZA is a neutral carbon atom of an N-heterocyclic carbene.
    • 9. The compound of claim 1, wherein
      • the compound has the formula M(LA)x(LB)y(LC)z; wherein
  • 14
    14. An organic light-emitting device (OLED) comprising:
    • an anode
    • a cathode
    • and an organic layer, disposed between the anode and the cathode, comprising a compound comprising a first ligand LA of Formula I: Formula I
    • wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring
    • wherein RA represents from disubstitution to the possible maximum number of substitution
    • wherein RB represents monosubstitution to the possible maximum number of substitution, or no substitution
    • wherein ZA and ZB are each independently selected from the group consisting of carbon or nitrogen
    • wherein at least two adjacent RA are joined and fused to ring A and have the following formula: wherein A1, A2, A3, and A4 are each independently CR or N
    • each R can be the same or different
    • wherein Z1 and Z2 are each independently selected from the group consisting of O, S, Se, NR′, CR′R″, and SiR′R″
    • wherein the ring containing Z1 and Z2 is a non-aromatic ring
    • wherein R, R′, R″, RA, and RB are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof
    • wherein any adjacent substituents are optionally joined or fused into a ring
    • wherein the ligand LA is coordinated to a metal M
    • wherein the metal M can be coordinated to other ligands
    • and wherein the ligand LA is optionally linked with other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand.
    • 15. The OLED of claim 14, wherein
      • the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.
    • 16. The OLED of claim 14, wherein
      • the organic layer further comprises
    • 17. The OLED of claim 14, wherein
      • the organic layer further comprises
    • 18. The OLED of claim 14, wherein
      • the organic layer further comprises
  • 19
    19. A consumer product comprising
    • an organic light-emitting device (OLED) comprising: an anode
    • a cathode
    • and an organic layer, disposed between the anode and the cathode, comprising a compound comprising a first ligand LA of Formula I: Formula I
    • wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring
    • wherein RA represents from disubstitution to the possible maximum number of substitution
    • wherein RB represents monosubstitution to the possible maximum number of substitution, or no substitution
    • wherein ZA and ZB are each independently selected from the group consisting of carbon or nitrogen
    • wherein at least two adjacent RA are joined and fused to ring A and have the following formula: wherein A1, A2, A3, and A4 are each independently CR or N
    • each R can be the same or different
    • wherein Z1 and Z2 are each independently selected from the group consisting of O, S, Se, NR′, CR′R″, and SiR′R″
    • wherein the ring containing Z1 and Z2 is a non-aromatic ring
    • wherein R, R′, R″, RA, and RB are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof
    • wherein any adjacent substituents are optionally joined or fused into a ring
    • wherein the ligand LA is coordinated to a metal M
    • wherein the metal M can be coordinated to other ligands
    • and wherein the ligand LA is optionally linked with other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand.
    • 20. The consumer product of claim 19, wherein
      • the consumer product is selected from the group consisting of
See all independent claims <>

Description

FIELD

The present invention relates to compounds for use as emitters, and devices, such as organic light emitting diodes, including the same.

BACKGROUND

Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.

OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.

One application for phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as “saturated” colors. In particular, these standards call for saturated red, green, and blue pixels. Alternatively the OLED can be designed to emit white light. In conventional liquid crystal displays emission from a white backlight is filtered using absorption filters to produce red, green and blue emission. The same technique can also be used with OLEDs. The white OLED can be either a single EML device or a stack structure. Color may be measured using CIE coordinates, which are well known to the art.

One example of a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy)3, which has the following structure:

In this, and later figures herein, we depict the dative bond from nitrogen to metal (here, Ir) as a straight line.

As used herein, the term “organic” includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices. “Small molecule” refers to any organic material that is not a polymer, and “small molecules” may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the “small molecule” class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety. The core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a “small molecule,” and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.

As used herein, “top” means furthest away from the substrate, while “bottom” means closest to the substrate. Where a first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is “in contact with” the second layer. For example, a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.

As used herein, “solution processible” means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.

A ligand may be referred to as “photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material. A ligand may be referred to as “ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.

As used herein, and as would be generally understood by one skilled in the art, a first “Highest Occupied Molecular Orbital” (HOMO) or “Lowest Unoccupied Molecular Orbital” (LUMO) energy level is “greater than” or “higher than” a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since ionization potentials (IP) are measured as a negative energy relative to a vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative). On a conventional energy level diagram, with the vacuum level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. A “higher” HOMO or LUMO energy level appears closer to the top of such a diagram than a “lower” HOMO or LUMO energy level.

As used herein, and as would be generally understood by one skilled in the art, a first work function is “greater than” or “higher than” a second work function if the first work function has a higher absolute value. Because work functions are generally measured as negative numbers relative to vacuum level, this means that a “higher” work function is more negative. On a conventional energy level diagram, with the vacuum level at the top, a “higher” work function is illustrated as further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.

More details on OLEDs, and the definitions described above, can be found in U.S. Pat. No. 7,279,704, which is incorporated herein by reference in its entirety.

There is need in the art for novel emitters which can be used for electroluminescent devices. The present invention addresses this unmet need in the art.

SUMMARY

According to an embodiment, a compound is provided comprising a first ligand LA of Formula I:

Formula I;

wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring;

wherein RA represents from disubstitution to the possible maximum number of substitution;

wherein RB represents monosubstitution to the possible maximum number of substitution, or no substitution;

wherein ZA and ZB are each independently selected from the group consisting of carbon or nitrogen;

wherein at least two adjacent RA are joined and fused to ring A and have the following formula:

wherein A1, A2, A3, and A4 are each independently CR or N;

each R can be the same or different;

wherein Z1 and Z2 are each independently selected from the group consisting of O, S, Se, NR′, CR′R″, and SiR′R″;

wherein the ring containing Z1 and Z2 is a non-aromatic ring;

wherein R, R′, R″, RA, and RB are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein any adjacent substituents are optionally joined or fused into a ring;

wherein the ligand LA is coordinated to a metal M;

wherein the metal M can be coordinated to other ligands; and

wherein the ligand LA is optionally linked with other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand.

According to another embodiment, an organic light emitting diode/device (OLED) is also provided. The OLED can include an anode, a cathode, and an organic layer, disposed between the anode and the cathode. The organic layer can include a compound comprising a first ligand LA of Formula I. According to yet another embodiment, the organic light emitting device is incorporated into a device selected from a consumer product, an electronic component module, and/or a lighting panel.

According to another embodiment, a consumer product comprising one or more organic light emitting devices is also provided. The organic light emitting device can include an anode, a cathode, and an organic layer, disposed between the anode and the cathode, wherein the organic layer can include a compound comprising a first ligand LA of Formula I. The consumer product can be a flat panel display, a computer monitor, a medical monitors television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, and/or a sign.

According to another embodiment, a formulation comprising a compound comprising a first ligand LA of Formula I is provided.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows an organic light emitting device.

FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.

DETAILED DESCRIPTION

Generally, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer(s). The injected holes and electrons each migrate toward the oppositely charged electrode. When an electron and hole localize on the same molecule, an “exciton,” which is a localized electron-hole pair having an excited energy state, is formed. Light is emitted when the exciton relaxes via a photoemissive mechanism. In some cases, the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.

The initial OLEDs used emissive molecules that emitted light from their singlet states (“fluorescence”) as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.

More recently, OLEDs having emissive materials that emit light from triplet states (“phosphorescence”) have been demonstrated. Baldo et al., “Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,” Nature, vol. 395, 151-154, 1998; (“Baldo-I”) and Baldo et al., “Very high-efficiency green organic light-emitting devices based on electrophosphorescence,” Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999) (“Baldo-II”), are incorporated by reference in their entireties. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704 at cols. 5-6, which are incorporated by reference.

FIG. 1 shows an organic light emitting device 100. The figures are not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a barrier layer 170. Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in U.S. Pat. No. 7,279,704 at cols. 6-10, which are incorporated by reference.

More examples for each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of emissive and host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, disclose examples of cathodes including compound cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, electrically-conductive, sputter-deposited ITO layer. The theory and use of blocking layers is described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers may be found in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.

FIG. 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230, device 200 may be referred to as an “inverted” OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200. FIG. 2 provides one example of how some layers may be omitted from the structure of device 100.

The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non-limiting example, and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an “organic layer” disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2.

Structures and materials not specifically described may also be used, such as OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. By way of further example, OLEDs having a single organic layer may be used. OLEDs may be stacked, for example as described in U.S. Pat. No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety. The OLED structure may deviate from the simple layered structure illustrated in FIGS. 1 and 2. For example, the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties.

Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For the organic layers, preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety. Other suitable deposition methods include spin coating and other solution based processes. Solution based processes are preferably carried out in nitrogen or an inert atmosphere. For the other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and OVJD. Other methods may also be used. The materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processability than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.

Devices fabricated in accordance with embodiments of the present invention may further optionally comprise a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damaging exposure to harmful species in the environment including moisture, vapor and/or gases, etc. The barrier layer may be deposited over, under or next to a substrate, an electrode, or over any other parts of a device including an edge. The barrier layer may comprise a single layer, or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate an inorganic or an organic compound or both. The preferred barrier layer comprises a mixture of a polymeric material and a non-polymeric material as described in U.S. Pat. No. 7,968,146, PCT Pat. Application Nos. PCT/US2007/023098 and PCT/US2009/042829, which are herein incorporated by reference in their entireties. To be considered a “mixture”, the aforesaid polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and/or at the same time. The weight ratio of polymeric to non-polymeric material may be in the range of 95:5 to 5:95. The polymeric material and the non-polymeric material may be created from the same precursor material. In one example, the mixture of a polymeric material and a non-polymeric material consists essentially of polymeric silicon and inorganic silicon.

Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, lighting devices such as discrete light source devices or lighting panels, etc. that can be utilized by the end-user product manufacturers. Such electronic component modules can optionally include the driving electronics and/or power source(s). Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of consumer products that have one or more of the electronic component modules (or units) incorporated therein. Such consumer products would include any kind of products that include one or more light source(s) and/or one or more of some type of visual displays. Some examples of such consumer products include flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cell phones, tablets, phablets, personal digital assistants (PDAs), wearable device, laptop computers, digital cameras, camcorders, viewfinders, micro-displays that are less than 2 inches diagonal, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screen, or a sign. Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C., and more preferably at room temperature (20-25 degrees C.), but could be used outside this temperature range, for example, from −40 degree C. to +80 degree C.

The materials and structures described herein may have applications in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures. More generally, organic devices, such as organic transistors, may employ the materials and structures.

The term “halo,”“halogen,” or “halide” as used herein includes fluorine, chlorine, bromine, and iodine.

The term “alkyl” as used herein contemplates both straight and branched chain alkyl radicals. Preferred alkyl groups are those containing from one to fifteen carbon atoms and includes methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, and the like. Additionally, the alkyl group may be optionally substituted.

The term “cycloalkyl” as used herein contemplates cyclic alkyl radicals. Preferred cycloalkyl groups are those containing 3 to 10 ring carbon atoms and includes cyclopropyl, cyclopentyl, cyclohexyl, adamantyl, and the like. Additionally, the cycloalkyl group may be optionally substituted.

The term “alkenyl” as used herein contemplates both straight and branched chain alkene radicals. Preferred alkenyl groups are those containing two to fifteen carbon atoms. Additionally, the alkenyl group may be optionally substituted.

The term “alkynyl” as used herein contemplates both straight and branched chain alkyne radicals. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group may be optionally substituted.

The terms “aralkyl” or “arylalkyl” as used herein are used interchangeably and contemplate an alkyl group that has as a substituent an aromatic group. Additionally, the aralkyl group may be optionally substituted.

The term “heterocyclic group” as used herein contemplates aromatic and non-aromatic cyclic radicals. Hetero-aromatic cyclic radicals also means heteroaryl. Preferred hetero-non-aromatic cyclic groups are those containing 3 to 7 ring atoms which includes at least one hetero atom, and includes cyclic amines such as morpholino, piperdino, pyrrolidino, and the like, and cyclic ethers, such as tetrahydrofuran, tetrahydropyran, and the like. Additionally, the heterocyclic group may be optionally substituted.

The term “aryl” or “aromatic group” as used herein contemplates single-ring groups and polycyclic ring systems. The polycyclic rings may have two or more rings in which two carbons are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is aromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty carbon atoms, more preferably six to twelve carbon atoms. Especially preferred is an aryl group having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group may be optionally substituted.

The term “heteroaryl” as used herein contemplates single-ring hetero-aromatic groups that may include from one to five heteroatoms. The term heteroaryl also includes polycyclic hetero-aromatic systems having two or more rings in which two atoms are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is a heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. Preferred heteroaryl groups are those containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza-analogs thereof. Additionally, the heteroaryl group may be optionally substituted.

The alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocyclic group, aryl, and heteroaryl may be unsubstituted or may be substituted with one or more substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, cyclic amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

As used herein, “substituted” indicates that a substituent other than H is bonded to the relevant position, such as carbon. Thus, for example, where R1 is mono-substituted, then one R1 must be other than H. Similarly, where R1 is di-substituted, then two of R1 must be other than H. Similarly, where R1 is unsubstituted, R1 is hydrogen for all available positions.

The “aza” designation in the fragments described herein, i.e. aza-dibenzofuran, aza-dibenzothiophene, etc. means that one or more of the C—H groups in the respective fragment can be replaced by a nitrogen atom, for example, and without any limitation, azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. One of ordinary skill in the art can readily envision other nitrogen analogs of the aza-derivatives described above, and all such analogs are intended to be encompassed by the terms as set forth herein.

It is to be understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. phenyl, phenylene, naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g. benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered to be equivalent.

In one aspect, the present invention includes phosphorescent metal complexes derived from pyridyl substituted aromatic compound core structures. These compounds can be used as emitters for PHOLEDs.

Compounds of the Invention

In one aspect, the present invention includes a compound comprising a first ligand LA of Formula I:

Formula I;

wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring;

wherein RA represents from disubstitution to the possible maximum number of substitution;

wherein RB represents monosubstitution to the possible maximum number of substitution, or no substitution;

wherein ZA and ZB are each independently selected from the group consisting of carbon or nitrogen;

wherein at least two adjacent RA are joined and fused to ring A and have the following formula:

wherein A1, A2, A3, and A4 are each independently CR or N;

each R can be the same or different;

wherein Z1 and Z2 are each independently selected from the group consisting of O, S, Se, NR′, CR′R″, and SiR′R″;

wherein the ring containing Z1 and Z2 is a non-aromatic ring;

wherein R, R′, R″, RA, and RB are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein any adjacent substituents are optionally joined or fused into a ring;

wherein the ligand LA is coordinated to a metal M;

wherein the metal M can be coordinated to other ligands; and

wherein the ligand LA is optionally linked with other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand.

In one embodiment, M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu. In another embodiment, M is Ir or Pt.

In one embodiment, the compound is homoleptic. In another embodiment, the compound is heteroleptic.

In one embodiment, each of A1, A2, A3, and A4 is independently CR. In one embodiment, ring B connects to ring A through a C—C bond.

In one embodiment, ZA an sp2 neutral nitrogen atom of an N-heterocyclic ring selected from the group consisting of pyridine, pyrimidine, imidazole, benzoimidazole, pyrazole, oxazole, and triazole. In one embodiment, ZA is a neutral carbon atom of an N-heterocyclic carbene.

In one embodiment, Z1 and Z2 are a pair selected from the group consisting of: (O and NR′), (O and SiR′R″), (SiR′R″ and SiR′R″), (O and O), (O and CR′R″), (SiR′R″ and CR′R″), and (CR′R″ and CR′R″).

In one embodiment, the compound has the formula M(LA)x(LB)y(LC)z;

wherein LB is a second ligand, and LC is a third ligand, and LB and LC can be the same or different;

wherein x is 1, 2, or 3;

wherein y is 0, 1, or 2;

wherein z is 0, 1, or 2;

wherein x+y+z is the oxidation state of the metal M;

wherein the second ligand LB and the third ligand LC are each independently selected from the group consisting of:

wherein X1 to X13 are each independently selected from the group consisting of carbon and nitrogen;

wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;

wherein R′ and R″ are optionally fused or joined to form a ring;

wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;

wherein R′, R″, Ra, Rb, Rc, and Rd are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or a multidentate ligand.

In one embodiment, the ligand LA is selected from the group consisting of:

In one embodiment, the compound has the formula Ir(LA)n(LB)3-n; wherein n is 1, 2, or 3.

In one embodiment, the ligand LB is selected from the group consisting of:


LBj, j
RB1
RB2
RB3
RB4
 1.
H
H
H
H
 2.
CH3
H
H
H
 3.
H
CH3
H
H
 4.
H
H
CH3
H
 5.
H
H
H
CH3
 6.
CH3
H
CH3
H
 7.
CH3
H
H
CH3
 8.
H
CH3
CH3
H
 9.
H
CH3
H
CH3
 10.
H
H
CH3
CH3
 11.
CH3
CH3
CH3
H
 12.
CH3
CH3
H
CH3
 13.
CH3
H
CH3
CH3
 14.
H
CH3
CH3
CH3
 15.
CH3
CH3
CH3
CH3
 16.
CH2CH3
H
H
H
 17.
CH2CH3
CH3
H
H
 18.
CH2CH3
H
CH3
H
 19.
CH2CH3
H
H
CH3
 20.
CH2CH3
CH3
CH3
H
 21.
CH2CH3
CH3
H
CH3
 22.
CH2CH3
H
CH3
CH3
 23.
CH2CH3
CH3
CH3
CH3
 24.
H
CH2CH3
H
H
 25.
CH3
CH2CH3
H
H
 26.
H
CH2CH3
CH3
H
 27.
H
CH2CH3
H
CH3
 28.
CH3
CH2CH3
CH3
H
 29.
CH3
CH2CH3
H
CH3
 30.
H
CH2CH3
CH3
CH3
 31.
CH3
CH2CH3
CH3
CH3
 32.
H
H
CH2CH3
H
 33.
CH3
H
CH2CH3
H
 34.
H
CH3
CH2CH3
H
 35.
H
H
CH2CH3
CH3
 36.
CH3
CH3
CH2CH3
H
 37.
CH3
H
CH2CH3
CH3
 38.
H
CH3
CH2CH3
CH3
 39.
CH3
CH3
CH2CH3
CH3
 40.
CH(CH3)2
H
H
H
 41.
CH(CH3)2
CH3
H
H
 42.
CH(CH3)2
H
CH3
H
 43.
CH(CH3)2
H
H
CH3
 44.
CH(CH3)2
CH3
CH3
H
 45.
CH(CH3)2
CH3
H
CH3
 46.
CH(CH3)2
H
CH3
CH3
 47.
CH(CH3)2
CH3
CH3
CH3
 48.
H
CH(CH3)2
H
H
 49.
CH3
CH(CH3)2
H
H
 50.
H
CH(CH3)2
CH3
H
 51.
H
CH(CH3)2
H
CH3
 52.
CH3
CH(CH3)2
CH3
H
 53.
CH3
CH(CH3)2
H
CH3
 54.
H
CH(CH3)2
CH3
CH3
 55.
CH3
CH(CH3)2
CH3
CH3
 56.
H
H
CH(CH3)2
H
 57.
CH3
H
CH(CH3)2
H
 58.
H
CH3
CH(CH3)2
H
 59.
H
H
CH(CH3)2
CH3
 60.
CH3
CH3
CH(CH3)2
H
 61.
CH3
H
CH(CH3)2
CH3
 62.
H
CH3
CH(CH3)2
CH3
 63.
CH3
CH3
CH(CH3)2
CH3
 64.
CH2CH(CH3)2
H
H
H
 65.
CH2CH(CH3)2
CH3
H
H
 66.
CH2CH(CH3)2
H
CH3
H
 67.
CH2CH(CH3)2
H
H
CH3
 68.
CH2CH(CH3)2
CH3
CH3
H
 69.
CH2CH(CH3)2
CH3
H
CH3
 70.
CH2CH(CH3)2
H
CH3
CH3
 71.
CH2CH(CH3)2
CH3
CH3
CH3
 72.
H
CH2CH(CH3)2
H
H
 73.
CH3
CH2CH(CH3)2
H
H
 74.
H
CH2CH(CH3)2
CH3
H
 75.
H
CH2CH(CH3)2
H
CH3
 76.
CH3
CH2CH(CH3)2
CH3
H
 77.
CH3
CH2CH(CH3)2
H
CH3
 78.
H
CH2CH(CH3)2
CH3
CH3
 79.
CH3
CH2CH(CH3)2
CH3
CH3
 80.
H
H
CH2CH(CH3)2
H
 81.
CH3
H
CH2CH(CH3)2
H
 82.
H
CH3
CH2CH(CH3)2
H
 83.
H
H
CH2CH(CH3)2
CH3
 84.
CH3
CH3
CH2CH(CH3)2
H
 85.
CH3
H
CH2CH(CH3)2
CH3
 86.
H
CH3
CH2CH(CH3)2
CH3
 87.
CH3
CH3
CH2CH(CH3)2
CH3
 88.
C(CH3)3
H
H
H
 89.
C(CH3)3
CH3
H
H
 90.
C(CH3)3
H
CH3
H
 91.
C(CH3)3
H
H
CH3
 92.
C(CH3)3
CH3
CH3
H
 93.
C(CH3)3
CH3
H
CH3
 94.
C(CH3)3
H
CH3
CH3
 95.
C(CH3)3
CH3
CH3
CH3
 96.
H
C(CH3)3
H
H
 97.
CH3
C(CH3)3
H
H
 98.
H
C(CH3)3
CH3
H
 99.
H
C(CH3)3
H
CH3
100.
CH3
C(CH3)3
CH3
H
101.
CH3
C(CH3)3
H
CH3
102.
H
C(CH3)3
CH3
CH3
103.
CH3
C(CH3)3
CH3
CH3
104.
H
H
C(CH3)3
H
105.
CH3
H
C(CH3)3
H
106.
H
CH3
C(CH3)3
H
107.
H
H
C(CH3)3
CH3
108.
CH3
CH3
C(CH3)3
H
109.
CH3
H
C(CH3)3
CH3
110.
H
CH3
C(CH3)3
CH3
111.
CH3
CH3
C(CH3)3
CH3
112.
CH2C(CH3)3
H
H
H
113.
CH2C(CH3)3
CH3
H
H
114.
CH2C(CH3)3
H
CH3
H
115.
CH2C(CH3)3
H
H
CH3
116.
CH2C(CH3)3
CH3
CH3
H
117.
CH2C(CH3)3
CH3
H
CH3
118.
CH2C(CH3)3
H
CH3
CH3
119.
CH2C(CH3)3
CH3
CH3
CH3
120.
H
CH2C(CH3)3
H
H
121.
CH3
CH2C(CH3)3
H
H
122.
H
CH2C(CH3)3
CH3
H
123.
H
CH2C(CH3)3
H
CH3
124.
CH3
CH2C(CH3)3
CH3
H
125.
CH3
CH2C(CH3)3
H
CH3
126.
H
CH2C(CH3)3
CH3
CH3
127.
CH3
CH2C(CH3)3
CH3
CH3
128.
H
H
CH2C(CH3)3
H
129.
CH3
H
CH2C(CH3)3
H
130.
H
CH3
CH2C(CH3)3
H
131.
H
H
CH2C(CH3)3
CH3
132.
CH3
CH3
CH2C(CH3)3
H
133.
CH3
H
CH2C(CH3)3
CH3
134.
H
CH3
CH2C(CH3)3
CH3
135.
CH3
CH3
CH2C(CH3)3
CH3
136.
CH2C(CH3)2CF3
H
H
H
137.
CH2C(CH3)2CF3
CH3
H
H
138.
CH2C(CH3)2CF3
H
CH3
H
139.
CH2C(CH3)2CF3
H
H
CH3
140.
CH2C(CH3)2CF3
CH3
CH3
H
141.
CH2C(CH3)2CF3
CH3
H
CH3
142.
CH2C(CH3)2CF3
H
CH3
CH3
143.
CH2C(CH3)2CF3
CH3
CH3
CH3
144.
H
CH2C(CH3)2CF3
H
H
145.
CH3
CH2C(CH3)2CF3
H
H
146.
H
CH2C(CH3)2CF3
CH3
H
147.
H
CH2C(CH3)2CF3
H
CH3
148.
CH3
CH2C(CH3)2CF3
CH3
H
149.
CH3
CH2C(CH3)2CF3
H
CH3
150.
H
CH2C(CH3)2CF3
CH3
CH3
151.
CH3
CH2C(CH3)2CF3
CH3
CH3
152.
H
H
CH2C(CH3)2CF3
H
153.
CH3
H
CH2C(CH3)2CF3
H
154.
H
CH3
CH2C(CH3)2CF3
H
155.
H
H
CH2C(CH3)2CF3
CH3
156.
CH3
CH3
CH2C(CH3)2CF3
H
157.
CH3
H
CH2C(CH3)2CF3
CH3
158.
H
CH3
CH2C(CH3)2CF3
CH3
159.
CH3
CH3
CH2C(CH3)2CF3
CH3
160.
CH2CH2CF3
H
H
H
161.
CH2CH2CF3
CH3
H
H
162.
CH2CH2CF3
H
CH3
H
163.
CH2CH2CF3
H
H
CH3
164.
CH2CH2CF3
CH3
CH3
H
165.
CH2CH2CF3
CH3
H
CH3
166.
CH2CH2CF3
H
CH3
CH3
167.
CH2CH2CF3
CH3
CH3
CH3
168.
H
CH2CH2CF3
H
H
169.
CH3
CH2CH2CF3
H
H
170.
H
CH2CH2CF3
CH3
H
171.
H
CH2CH2CF3
H
CH3
172.
CH3
CH2CH2CF3
CH3
H
173.
CH3
CH2CH2CF3
H
CH3
174.
H
CH2CH2CF3
CH3
CH3
175.
CH3
CH2CH2CF3
CH3
CH3
176.
H
H
CH2CH2CF3
H
177.
CH3
H
CH2CH2CF3
H
178.
H
CH3
CH2CH2CF3
H
179.
H
H
CH2CH2CF3
CH3
180.
CH3
CH3
CH2CH2CF3
H
181.
CH3
H
CH2CH2CF3
CH3
182.
H
CH3
CH2CH2CF3
CH3
183.
CH3
CH3
CH2CH2CF3
CH3
184.
H
H
H
185.
CH3
H
H
186.
H
CH3
H
187.
H
H
CH3
188.
CH3
CH3
H
189.
CH3
H
CH3
190.
H
CH3
CH3
191.
CH3
CH3
CH3
192.
H
H
H
193.
CH3
H
H
194.
H
CH3
H
195.
H
H
CH3
196.
CH3
CH3
H
197.
CH3
H
CH3
198.
H
CH3
CH3
199.
CH3
CH3
CH3
200.
H
H
H
201.
CH3
H
H
202.
H
CH3
H
203.
H
H
CH3
204.
CH3
CH3
H
205.
CH3
H
CH3
206.
H
CH3
CH3
207.
CH3
CH3
CH3
208.
H
H
H
209.
CH3
H
H
210.
H
CH3
H
211.
H
H
CH3
212.
CH3
CH3
H
213.
CH3
H
CH3
214.
H
CH3
CH3
215.
CH3
CH3
CH3
216.
H
H
H
217.
CH3
H
H
218.
H
CH3
H
219.
H
H
CH3
220.
CH3
CH3
H
221.
CH3
H
CH3
222.
H
CH3
CH3
223.
CH3
CH3
CH3
224.
H
H
H
225.
CH3
H
H
226.
H
CH3
H
227.
H
H
CH3
228.
CH3
CH3
H
229.
CH3
H
CH3
230.
H
CH3
CH3
231.
CH3
CH3
CH3
232.
H
H
H
233.
CH3
H
H
234.
H
CH3
H
235.
H
H
CH3
236.
CH3
CH3
H
237.
CH3
H
CH3
238.
H
CH3
CH3
239.
CH3
CH3
CH3
240.
H
H
H
241.
CH3
H
H
242.
H
CH3
H
243.
H
H
CH3
244.
CH3
CH3
H
245.
CH3
H
CH3
246.
H
CH3
CH3
247.
CH3
CH3
CH3
248.
H
H
H
249.
CH3
H
H
250.
H
CH3
H
251.
H
H
CH3
252.
CH3
CH3
H
253.
CH3
H
CH3
254.
H
CH3
CH3
255.
CH3
CH3
CH3
256.
H
H
H
257.
CH3
H
H
258.
H
CH3
H
259.
H
H
CH3
260.
CH3
CH3
H
261.
CH3
H
CH3
262.
H
CH3
CH3
263.
CH3
CH3
CH3
264.
H
H
H
265.
CH3
H
H
266.
H
CH3
H
267.
H
H
CH3
268.
CH3
CH3
H
269.
CH3
H
CH3
270.
H
CH3
CH3
271.
CH3
CH3
CH3
272.
H
H
H
273.
CH3
H
H
274.
H
CH3
H
275.
H
H
CH3
276.
CH3
CH3
H
277.
CH3
H
CH3
278.
H
CH3
CH3
279.
CH3
CH3
CH3
280.
H
H
H
281.
CH3
H
H
282.
H
CH3
H
283.
H
H
CH3
284.
CH3
CH3
H
285.
CH3
H
CH3
286.
H
CH3
CH3
287.
CH3
CH3
CH3
288.
H
H
H
289.
CH3
H
H
290.
H
CH3
H
291.
H
H
CH3
292.
CH3
CH3
H
293.
CH3
H
CH3
294.
H
CH3
CH3
295.
CH3
CH3
CH3
296.
H
H
H
297.
CH3
H
H
298.
H
CH3
H
299.
H
H
CH3
300.
CH3
CH3
H
301.
CH3
H
CH3
302.
H
CH3
CH3
303.
CH3
CH3
CH3
304.
H
H
H
305.
CH3
H
H
306.
H
CH3
H
307.
H
H
CH3
308.
CH3
CH3
H
309.
CH3
H
CH3
310.
H
CH3
CH3
311.
CH3
CH3
CH3
312.
H
H
H
313.
CH3
H
H
314.
H
CH3
H
315.
H
H
CH3
316.
CH3
CH3
H
317.
CH3
H
CH3
318.
H
CH3
CH3
319.
CH3
CH3
CH3
320.
H
H
H
321.
CH3
H
H
322.
H
CH3
H
323.
H
H
CH3
324.
CH3
CH3
H
325.
CH3
H
CH3
326.
H
CH3
CH3
327.
CH3
CH3
CH3
328.
CH(CH3)2
H
CH2CH3
H
329.
CH(CH3)2
H
CH(CH3)2
H
330.
CH(CH3)2
H
CH2CH(CH3)2
H
331.
CH(CH3)2
H
C(CH3)3
H
332.
CH(CH3)2
H
CH2C(CH3)3
H
333.
CH(CH3)2
H
CH2CH2CF3
H
334.
CH(CH3)2
H
CH2C(CH3)2CF3
H
335.
CH(CH3)2
H
H
336.
CH(CH3)2
H
H
337.
CH(CH3)2
H
H
338.
CH(CH3)2
H
H
339.
CH(CH3)2
H
H
340.
CH(CH3)2
H
H
341.
C(CH3)3
H
CH2CH3
H
342.
C(CH3)3
H
CH(CH3)2
H
343.
C(CH3)3
H
CH2CH(CH3)2
H
344.
C(CH3)3
H
C(CH3)3
H
345.
C(CH3)3
H
CH2C(CH3)3
H
346.
C(CH3)3
H
CH2CH2CF3
H
347.
C(CH3)3
H
CH2C(CH3)2CF3
H
348.
C(CH3)3
H
H
349.
C(CH3)3
H
H
350.
C(CH3)3
H
H
351.
C(CH3)3
H
H
352.
C(CH3)3
H
H
353.
C(CH3)3
H
H
354.
CH2C(CH3)3
H
CH2CH3
H
355.
CH2C(CH3)3
H
CH(CH3)2
H
356.
CH2C(CH3)3
H
CH2CH(CH3)2
H
357.
CH2C(CH3)3
H
C(CH3)3
H
358.
CH2C(CH3)3
H
CH2C(CH3)3
H
359.
CH2C(CH3)3
H
CH2CH2CF3
H
360.
CH2C(CH3)3
H
CH2C(CH3)2CF3
H
361.
CH2C(CH3)3
H
H
362.
CH2C(CH3)3
H
H
363.
CH2C(CH3)3
H
H
364.
CH2C(CH3)3
H
H
365.
CH2C(CH3)3
H
H
366.
CH2C(CH3)3
H
H
367.
H
CH2CH3
H
368.
H
CH(CH3)2
H
369.
H
CH2CH(CH3)2
H
370.
H
C(CH3)3
H
371.
H
CH2C(CH3)3
H
372.
H
CH2CH2CF3
H
373.
H
CH2C(CH3)2CF3
H
374.
H
H
375.
H
H
376.
H
H
377.
H
H
378.
H
H
379.
H
H
380.
H
CH2CH3
H
381.
H
CH(CH3)2
H
382.
H
CH2CH(CH3)2
H
383.
H
C(CH3)3
H
384.
H
CH2C(CH3)3
H
385.
H
CH2CH2CF3
H
386.
H
CH2C(CH3)2CF3
H
387.
H
H
388.
H
H
389.
H
H
390.
H
H
391.
H
H
392.
H
H
393.
H
CH2CH(CH3)2
H
394.
H
C(CH3)3
H
395.
H
CH2C(CH3)3
H
396.
H
CH2CH2CF3
H
397.
H
CH2C(CH3)2CF3
H
398.
H
H
399.
H
H
400.
H
H
401.
H
H
402.
H
H
403.
H
H
404.
H
CH2CH(CH3)2
H
405.
H
C(CH3)3
H
406.
H
CH2C(CH3)3
H
407.
H
CH2CH2CF3
H
408.
H
CH2C(CH3)2CF3
H
409.
H
H
410.
H
H
411.
H
H
412.
H
H
413.
H
H
414.
H
H
415.
H
CH2CH(CH3)2
H
416.
H
C(CH3)3
H
417.
H
CH2C(CH3)3
H
418.
H
CH2CH2CF3
H
419.
H
CH2C(CH3)2CF3
H
420.
H
H
421.
H
H
422.
H
H
423.
H
H
424.
H
H
425.
H
H
426.
CD3
H
H
H
427.
H
CD3
H
H
428.
H
H
CD3
H
429.
H
H
H
CD3
430.
CD3
H
CD3
H
431.
CD3
H
H
CD3
432.
H
CD3
CD3
H
433.
H
CD3
H
CD3
434.
H
H
CD3
CD3
435.
CD3
CD3
CD3
H
436.
CD3
CD3
H
CD3
437.
CD3
H
CD3
CD3
438.
H
CD3
CD3
CD3
439.
CD3
CD3
CD3
CD3
440.
CD2CH3
H
H
H
441.
CD2CH3
CD3
H
H
442.
CD2CH3
H
CD3
H
443.
CD2CH3
H
H
CD3
444.
CD2CH3
CD3
CD3
H
445.
CD2CH3
CD3
H
CD3
446.
CD2CH3
H
CD3
CD3
447.
CD2CH3
CD3
CD3
CD3
448.
H
CD2CH3
H
H
449.
CD3
CD2CH3
H
H
450.
H
CD2CH3
CD3
H
451.
H
CD2CH3
H
CD3
452.
CD3
CD2CH3
CD3
H
453.
CD3
CD2CH3
H
CD3
454.
H
CD2CH3
CD3
CD3
455.
CD3
CD2CH3
CD3
CD3
456.
H
H
CD2CH3
H
457.
CD3
H
CD2CH3
H
458.
H
CD3
CD2CH3
H
459.
H
H
CD2CH3
CD3
460.
CD3
CD3
CD2CH3
H
461.
CD3
H
CD2CH3
CD3
462.
H
CD3
CD2CH3
CD3
463.
CD3
CD3
CD2CH3
CD3
464.
CD(CH3)2
H
H
H
465.
CD(CH3)2
CD3
H
H
466.
CD(CH3)2
H
CD3
H
467.
CD(CH3)2
H
H
CD3
468.
CD(CH3)2
CD3
CD3
H
469.
CD(CH3)2
CD3
H
CD3
470.
CD(CH3)2
H
CD3
CD3
471.
CD(CH3)2
CD3
CD3
CD3
472.
H
CD(CH3)2
H
H
473.
CD3
CD(CH3)2
H
H
474.
H
CD(CH3)2
CD3
H
475.
H
CD(CH3)2
H
CD3
476.
CD3
CD(CH3)2
CD3
H
477.
CD3
CD(CH3)2
H
CD3
478.
H
CD(CH3)2
CD3
CD3
479.
CD3
CD(CH3)2
CD3
CD3
480.
H
H
CD(CH3)2
H
481.
CD3
H
CD(CH3)2
H
482.
H
CD3
CD(CH3)2
H
483.
H
H
CD(CH3)2
CD3
484.
CD3
CD3
CD(CH3)2
H
485.
CD3
H
CD(CH3)2
CD3
486.
H
CD3
CD(CH3)2
CD3
487.
CD3
CD3
CD(CH3)2
CD3
488.
CD(CD3)2
H
H
H
489.
CD(CD3)2
CD3
H
H
490.
CD(CD3)2
H
CD3
H
491.
CD(CD3)2
H
H
CD3
492.
CD(CD3)2
CD3
CD3
H
493.
CD(CD3)2
CD3
H
CD3
494.
CD(CD3)2
H
CD3
CD3
495.
CD(CD3)2
CD3
CD3
CD3
496.
H
CD(CD3)2
H
H
497.
CD3
CD(CD3)2
H
H
498.
H
CD(CD3)2
CD3
H
499.
H
CD(CD3)2
H
CD3
500.
CD3
CD(CD3)2
CD3
H
501.
CD3
CD(CD3)2
H
CD3
502.
H
CD(CD3)2
CD3
CD3
503.
CD3
CD(CD3)2
CD3
CD3
504.
H
H
CD(CD3)2
H
505.
CD3
H
CD(CD3)2
H
506.
H
CD3
CD(CD3)2
H
507.
H
H
CD(CD3)2
CD3
508.
CD3
CD3
CD(CD3)2
H
509.
CD3
H
CD(CD3)2
CD3
510.
H
CD3
CD(CD3)2
CD3
511.
CD3
CD3
CD(CD3)2
CD3
512.
CD2CH(CH3)2
H
H
H
513.
CD2CH(CH3)2
CD3
H
H
514.
CD2CH(CH3)2
H
CD3
H
515.
CD2CH(CH3)2
H
H
CD3
516.
CD2CH(CH3)2
CD3
CD3
H
517.
CD2CH(CH3)2
CD3
H
CD3
518.
CD2CH(CH3)2
H
CD3
CD3
519.
CD2CH(CH3)2
CD3
CD3
CD3
520.
H
CD2CH(CH3)2
H
H
521.
CD3
CD2CH(CH3)2
H
H
522.
H
CD2CH(CH3)2
CD3
H
523.
H
CD2CH(CH3)2
H
CD3
524.
CD3
CD2CH(CH3)2
CD3
H
525.
CD3
CD2CH(CH3)2
H
CD3
526.
H
CD2CH(CH3)2
CD3
CD3
527.
CD3
CD2CH(CH3)2
CD3
CD3
528.
H
H
CD2CH(CH3)2
H
529.
CD3
H
CD2CH(CH3)2
H
530.
H
CD3
CD2CH(CH3)2
H
531.
H
H
CD2CH(CH3)2
CD3
532.
CD3
CD3
CD2CH(CH3)2
H
533.
CD3
H
CD2CH(CH3)2
CD3
534.
H
CD3
CD2CH(CH3)2
CD3
535.
CD3
CD3
CD2CH(CH3)2
CD3
536.
CD2C(CH3)3
H
H
H
537.
CD2C(CH3)3
CD3
H
H
538.
CD2C(CH3)3
H
CD3
H
539.
CD2C(CH3)3
H
H
CD3
540.
CD2C(CH3)3
CD3
CD3
H
541.
CD2C(CH3)3
CD3
H
CD3
542.
CD2C(CH3)3
H
CD3
CD3
543.
CD2C(CH3)3
CH3
CD3
CD3
544.
H
CD2C(CH3)3
H
H
545.
CD3
CD2C(CH3)3
H
H
546.
H
CD2C(CH3)3
CD3
H
547.
H
CD2C(CH3)3
H
CD3
548.
CD3
CD2C(CH3)3
CD3
H
549.
CD3
CD2C(CH3)3
H
CD3
550.
H
CD2C(CH3)3
CD3
CD3
551.
CD3
CD2C(CH3)3
CD3
CD3
552.
H
H
CD2C(CH3)3
H
553.
CD3
H
CD2C(CH3)3
H
554.
H
CD3
CD2C(CH3)3
H
555.
H
H
CD2C(CH3)3
CD3
556.
CD3
CD3
CD2C(CH3)3
H
557.
CD3
H
CD2C(CH3)3
CD3
558.
H
CD3
CD2C(CH3)3
CD3
559.
CD3
CD3
CD2C(CH3)3
CD3
560.
CD2C(CH3)2CF3
H
H
H
561.
CD2C(CH3)2CF3
CD3
H
H
562.
CD2C(CH3)2CF3
H
CD3
H
563.
CD2C(CH3)2CF3
H
H
CD3
564.
CD2C(CH3)2CF3
CD3
CD3
H
565.
CD2C(CH3)2CF3
CD3
H
CD3
566.
CD2C(CH3)2CF3
H
CD3
CD3
567.
CD2C(CH3)2CF3
CD3
CD3
CD3
568.
H
CD2C(CH3)2CF3
H
H
569.
CD3
CD2C(CH3)2CF3
H
H
570.
H
CD2C(CH3)2CF3
CD3
H
571.
H
CD2C(CH3)2CF3
H
CD3
572.
CD3
CD2C(CH3)2CF3
CD3
H
573.
CD3
CD2C(CH3)2CF3
H
CD3
574.
H
CD2C(CH3)2CF3
CD3
CD3
575.
CD3
CD2C(CH3)2CF3
CD3
CD3
576.
H
H
CD2C(CH3)2CF3
H
577.
CD3
H
CD2C(CH3)2CF3
H
578.
H
CD3
CD2C(CH3)2CF3
H
579.
H
H
CD2C(CH3)2CF3
CD3
580.
CD3
CD3
CD2C(CH3)2CF3
H
581.
CD3
H
CD2C(CH3)2CF3
CD3
582.
H
CD3
CD2C(CH3)2CF3
CD3
583.
CD3
CD3
CD2C(CH3)2CF3
CD3
584.
CD2CH2CF3
H
H
H
585.
CD2CH2CF3
CD3
H
H
586.
CD2CH2CF3
H
CD3
H
587.
CD2CH2CF3
H
H
CD3
588.
CD2CH2CF3
CD3
CD3
H
589.
CD2CH2CF3
CD3
H
CD3
590.
CD2CH2CF3
H
CD3
CD3
591.
CD2CH2CF3
CD3
CD3
CD3
592.
H
CD2CH2CF3
H
H
593.
CD3
CD2CH2CF3
H
H
594.
H
CD2CH2CF3
CD3
H
595.
H
CD2CH2CF3
H
CD3
596.
CD3
CD2CH2CF3
CD3
H
597.
CD3
CD2CH2CF3
H
CD3
598.
H
CD2CH2CF3
CD3
CD3
599.
CD3
CD2CH2CF3
CD3
CD3
600.
H
H
CD2CH2CF3
H
601.
CD3
H
CD2CH2CF3
H
602.
H
CD3
CD2CH2CF3
H
603.
H
H
CD2CH2CF3
CD3
604.
CD3
CD3
CD2CH2CF3
H
605.
CD3
H
CD2CH2CF3
CD3
606.
H
CD3
CD2CH2CF3
CD3
607.
CD3
CD3
CD2CH2CF3
CD3
608.
H
H
H
609.
CD3
H
H
610.
H
CD3
H
611.
H
H
CD3
612.
CD3
CD3
H
613.
CD3
H
CD3
614.
H
CD3
CD3
615.
CD3
CD3
CD3
616.
H
H
H
617.
CD3
H
H
618.
H
CD3
H
619.
H
H
CD3
620.
CD3
CD3
H
621.
CD3
H
CD3
622.
H
CD3
CD3
623.
CD3
CD3
CD3
624.
H
H
H
625.
CD3
H
H
626.
H
CD3
H
627.
H
H
CD3
628.
CD3
CD3
H
629.
CD3
H
CD3
630.
H
CD3
CD3
631.
CD3
CD3
CD3
632.
H
H
H
633.
CD3
H
H
634.
H
CD3
H
635.
H
H
CD3
636.
CD3
CD3
H
637.
CD3
H
CD3
638.
H
CD3
CD3
639.
CD3
CD3
CD3
640.
H
H
H
641.
CD3
H
H
642.
H
CD3
H
643.
H
H
CD3
644.
CD3
CD3
H
645.
CD3
H
CD3
646.
H
CD3
CD3
647.
CH3
CD3
CD3
648.
H
H
H
649.
CD3
H
H
650.
H
CD3
H
651.
H
H
CD3
652.
CD3
CD3
H
653.
CD3
H
CD3
654.
H
CD3
CD3
655.
CD3
CD3
CD3
656.
H
H
H
657.
CD3
H
H
658.
H
CD3
H
659.
H
H
CD3
660.
CD3
CD3
H
661.
CD3
H
CD3
662.
H
CD3
CD3
663.
CD3
CD3
CD3
664.
H
H
H
665.
CD3
H
H
666.
H
CD3
H
667.
H
H
CD3
668.
CD3
CD3
H
669.
CD3
H
CD3
670.
H
CD3
CD3
671.
CD3
CD3
CD3
672.
H
H
H
673.
CD3
H
H
674.
H
CD3
H
675.
H
H
CD3
676.
CD3
CD3
H
677.
CD3
H
CD3
678.
H
CD3
CD3
679.
CD3
CD3
CD3
680.
H
H
H
681.
CD3
H
H
682.
H
CD3
H
683.
H
H
CD3
684.
CD3
CD3
H
685.
CD3
H
CD3
686.
H
CD3
CD3
687.
CD3
CD3
CD3
688.
H
H
H
689.
CD3
H
H
690.
H
CD3
H
691.
H
H
CD3
692.
CD3
CD3
H
693.
CD3
H
CD3
694.
H
CD3
CD3
695.
CD3
CD3
CD3
696.
H
H
H
697.
CD3
H
H
698.
H
CD3
H
699.
H
H
CD3
700.
CD3
CD3
H
701.
CD3
H
CD3
702.
H
CD3
CD3
703.
CD3
CD3
CD3
704.
H
H
H
705.
CD3
H
H
706.
H
CD3
H
707.
H
H
CD3
708.
CD3
CD3
H
709.
CD3
H
CD3
710.
H
CD3
CD3
711.
CD3
CD3
CD3
712.
H
H
H
713.
CD3
H
H
714.
H
CD3
H
715.
H
H
CD3
716.
CD3
CD3
H
717.
CD3
H
CD3
718.
H
CD3
CD3
719.
CD3
CD3
CD3
720.
H
H
H
721.
CD3
H
H
722.
H
CD3
H
723.
H
H
CD3
724.
CD3
CD3
H
725.
CD3
H
CD3
726.
H
CD3
CD3
727.
CD3
CD3
CD3
728.
H
H
H
729.
CD3
H
H
730.
H
CD3
H
731.
H
H
CD3
732.
CH3
CH3
H
733.
CD3
H
CD3
734.
H
CD3
CD3
735.
CD3
CD3
CD3
736.
H
H
H
737.
CD3
H
H
738.
H
CD3
H
739.
H
H
CD3
740.
CD3
CD3
H
741.
CD3
H
CD3
742.
H
CD3
CD3
743.
CD3
CD3
CD3
744.
H
H
H
745.
CD3
H
H
746.
H
CD3
H
747.
H
H
CD3
748.
CD3
CD3
H
749.
CD3
H
CD3
750.
H
CD3
CD3
751.
CD3
CD3
CD3
752.
CD(CH3)2
H
CD2CH3
H
753.
CD(CH3)2
H
CD(CD3)2
H
754.
CD(CH3)2
H
CD2CH(CH3)2
H
755.
CD(CH3)2
H
C(CH3)3
H
756.
CD(CH3)2
H
CD2C(CH3)3
H
757.
CD(CH3)2
H
CD2CH2CF3
H
758.
CD(CH3)2
H
CD2C(CH3)2CF3
H
759.
CD(CH3)2
H
H
760.
CD(CH3)2
H
H
761.
CD(CH3)2
H
H
762.
CD(CH3)2
H
H
763.
CD(CH3)2
H
H
764.
CD(CH3)2
H
H
765.
C(CH3)3
H
CD2CH3
H
766.
C(CH3)3
H
CD(CD3)2
H
767.
C(CH3)3
H
CD2CH(CH3)2
H
768.
C(CH3)3
H
CD2C(CH3)3
H
769.
C(CH3)3
H
CD2CH2CF3
H
770.
C(CH3)3
H
CD2C(CH3)2CF3
H
771.
C(CH3)3
H
H
772.
C(CH3)3
H
H
773.
C(CH3)3
H
H
774.
C(CH3)3
H
H
775.
C(CH3)3
H
H
776.
C(CH3)3
H
H
777.
CD2C(CH3)3
H
CD2CH3
H
778.
CD2C(CH3)3
H
CD(CD3)2
H
779.
CD2C(CH3)3
H
CD2CH(CH3)2
H
780.
CD2C(CH3)3
H
C(CH3)3
H
781.
CD2C(CH3)3
H
CD2C(CH3)3
H
782.
CD2C(CH3)3
H
CD2CH2CF3
H
783.
CD2C(CH3)3
H
CD2C(CH3)2CF3
H
784.
CD2C(CH3)3
H
H
785.
CD2C(CH3)3
H
H
786.
CD2C(CH3)3
H
H
787.
CD2C(CH3)3
H
H
788.
CD2C(CH3)3
H
H
789.
CD2C(CH3)3
H
H
790.
H
CD2CH3
H
791.
H
CD(CD3)2
H
792.
H
CD2CH(CH3)2
H
793.
H
C(CH3)3
H
794.
H
CD2C(CH3)3
H
795.
H
CD2CH2CF3
H
796.
H
CD2C(CH3)2CF3
H
797.
H
H
798.
H
H
799.
H
H
800.
H
H
801.
H
H
802.
H
H
803.
H
CD2CH3
H
804.
H
CD(CD3)2
H
805.
H
CD2CH(CH3)2
H
806.
H
C(CH3)3
H
807.
H
CD2C(CH3)3
H
808.
H
CD2CH2CF3
H
809.
H
CD2C(CH3)2CF3
H
810.
H
H
811.
H
H
812.
H
H
813.
H
H
814.
H
H
815.
H
H
816.
H
CD2CH3
H
817.
H
CD(CD3)2
H
818.
H
CD2CH(CH3)2
H
819.
H
C(CH3)3
H
820.
H
CD2C(CH3)3
H
821.
H
CD2CH2CF3
H
822.
H
CD2C(CH3)2CF3
H
823.
H
H
824.
H
H
825.
H
H
826.
H
H
827.
H
H
828.
H
H
829.
H
CD2CH3
H
830.
H
CD(CD3)2
H
831.
H
CD2CH(CH3)2
H
832.
H
C(CH3)3
H
833.
H
CD2C(CH3)3
H
834.
H
CD2CH2CF3
H
835.
H
CD2C(CH3)2CF3
H
836.
H
H
837.
H
H
838.
H
H
839.
H
H
840.
H
H
841.
H
H
842.
H
CD2CH3
H
843.
H
CD(CD3)2
H
844.
H
CD2CH(CH3)2
H
845.
H
C(CH3)3
H
846.
H
CD2C(CH3)3
H
847.
H
CD2CH2CF3
H
848.
H
CD2C(CH3)2CF3
H
849.
H
H
850.
H
H
851.
H
H
852.
H
H
853.
H
H
854.
H
H

In one embodiment, the compound the compound is the Compound x having the formula Ir(LAi)(LBj)2; wherein x=854t+j−854; i is an integer from 1 to 368, and j is an integer from 1 to 854.

In some embodiments, the compound can be an emissive dopant. In some embodiments, the compound can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.

According to another aspect of the present disclosure, an OLED is also provided. The OLED includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer may include a host and a phosphorescent dopant. The organic layer can include a compound comprising a first ligand LA of Formula I, and its variations as described herein.

The OLED can be incorporated into one or more of a consumer product, an electronic component module, and a lighting panel. The organic layer can be an emissive layer and the compound can be an emissive dopant in some embodiments, while the compound can be a non-emissive dopant in other embodiments.

According to another aspect of the present disclosure, a consumer product comprising an OLED is provided. The OLED may include an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer may include a host and one or more emitter dopants. In one embodiment, the organic layer includes a compound comprising a first ligand LA of Formula I, and its variations as described herein.

Non-limiting examples of consumer products include flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cell phones, tablets, phablets, personal digital assistants (PDAs), wearable device, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays that are less than 2 inches diagonal, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screens, and/or signs.

The organic layer can also include a host. In some embodiments, two or more hosts are preferred. In some embodiments, the hosts used maybe a) bipolar, b) electron transporting, c) hole transporting or d) wide band gap materials that play little role in charge transport. In some embodiments, the host can include a metal complex. The host can be a triphenylene containing benzo-fused thiophene or benzo-fused furan. Any substituent in the host can be an unfused substituent independently selected from the group consisting of CnH2n+1, OCnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH═CH—CnH2n+1, C≡C—CnH2n+1, Ar1, Ar1-Ar2, and CnH2n—Ar1, or the host has no substitution. In the preceding substituents n can range from 1 to 10; and Ar1 and Ar2 can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof. The host can be an inorganic compound. For example, a Zn containing inorganic material e.g. ZnS.

The host can be a compound comprising at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene. The host can include a metal complex. The host can be, but is not limited to, a specific compound selected from the group consisting of:

and combinations thereof. Additional information on possible hosts is provided below.

In yet another aspect of the present disclosure, a formulation that comprises a compound comprising a first ligand LA of Formula I is described. The formulation can include one or more components selected from the group consisting of a solvent, a host, a hole injection material, hole transport material, and an electron transport layer material, disclosed herein.

Combination with Other Materials

The materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device. For example, emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present. The materials described or referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.

Conductivity Dopants:

A charge transport layer can be doped with conductivity dopants to substantially alter its density of charge carriers, which will in turn alter its conductivity. The conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of the semiconductor may also be achieved. Hole-transporting layer can be doped by p-type conductivity dopants and n-type conductivity dopants are used in the electron-transporting layer.

Non-limiting examples of the conductivity dopants that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804 and US2012146012.

HIL/HTL:

A hole injecting/transporting material to be used in the present invention is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injecting/transporting material. Examples of the material include, but are not limited to: a phthalocyanine or porphyrin derivative; an aromatic amine derivative; an indolocarbazole derivative; a polymer containing fluorohydrocarbon; a polymer with conductivity dopants; a conducting polymer, such as PEDOT/PSS; a self-assembly monomer derived from compounds such as phosphonic acid and silane derivatives; a metal oxide derivative, such as MoOx; a p-type semiconducting organic compound, such as 1,4,5,8,9,12-Hexaazatriphenylenehexacarbonitrile; a metal complex, and a cross-linkable compounds.

Examples of aromatic amine derivatives used in HIL or HTL include, but not limit to the following general structures:

Each of Ar1 to Ar9 is selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Each Ar may be unsubstituted or may be substituted by a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

In one aspect, Ar1 to Ar9 is independently selected from the group consisting of:

wherein k is an integer from 1 to 20; X101 to X108 is C (including CH) or N; Z101 is NAr1, O, or S; Ar1 has the same group defined above.

Examples of metal complexes used in HIL or HTL include, but are not limited to the following general formula:

wherein Met is a metal, which can have an atomic weight greater than 40; (Y101-Y102) is a bidentate ligand, Y101 and Y102 are independently selected from C, N, O, P, and S; L101 is an ancillary ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.

In one aspect, (Y101-Y102) is a 2-phenylpyridine derivative. In another aspect, (Y101-Y102) is a carbene ligand. In another aspect, Met is selected from Ir, Pt, Os, and Zn. In a further aspect, the metal complex has a smallest oxidation potential in solution vs. Fc+/Fc couple less than about 0.6 V.

Non-limiting examples of the HIL and HTL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN102702075, DE102012005215, EP01624500, EP01698613, EP01806334, EP01930964, EP01972613, EP01997799, EP02011790, EP02055700, EP02055701, EP1725079, EP2085382, EP2660300, EP650955, JP07-073529, JP2005112765, JP2007091719, JP2008021687, JP2014-009196, KR20110088898, KR20130077473, TW201139402, U.S. Pat. No. 6,517,957, US20020158242, US20030162053, US20050123751, US20060182993, US20060240279, US20070145888, US20070181874, US20070278938, US20080014464, US20080091025, US20080106190, US20080124572, US20080145707, US20080220265, US20080233434, US20080303417, US2008107919, US20090115320, US20090167161, US2009066235, US2011007385, US20110163302, US2011240968, US2011278551, US2012205642, US2013241401, US20140117329, US2014183517, U.S. Pat. No. 5,061,569, U.S. Pat. No. 5,639,914, WO05075451, WO07125714, WO08023550, WO08023759, WO2009145016, WO2010061824, WO2011075644, WO2012177006, WO2013018530, WO2013039073, WO2013087142, WO2013118812, WO2013120577, WO2013157367, WO2013175747, WO2014002873, WO2014015935, WO2014015937, WO2014030872, WO2014030921, WO2014104514, WO2014157018.

EBL:

An electron blocking layer (EBL) may be used to reduce the number of electrons and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device may result in substantially higher efficiencies, and or longer lifetime, as compared to a similar device lacking a blocking layer. Also, a blocking layer may be used to confine emission to a desired region of an OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and/or higher triplet energy than the emitter closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and or higher triplet energy than one or more of the hosts closest to the EBL interface. In one aspect, the compound used in EBL contains the same molecule or the same functional groups used as one of the hosts described below.

Host:

The light emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as light emitting material, and may contain a host material using the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complexes or organic compounds may be used as long as the triplet energy of the host is larger than that of the dopant. Any host material may be used with any dopant so long as the triplet criteria is satisfied.

Examples of metal complexes used as host are preferred to have the following general formula:

wherein Met is a metal; (Y103-Y104) is a bidentate ligand, Y103 and Y104 are independently selected from C, N, O, P, and S; L101 is an another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.

In one aspect, the metal complexes are:

wherein (O—N) is a bidentate ligand, having metal coordinated to atoms O and N.

In another aspect, Met is selected from Ir and Pt. In a further aspect, (Y103-Y104) is a carbene ligand.

Examples of other organic compounds used as host are selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Each option within each group may be unsubstituted or may be substituted by a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

In one aspect, the host compound contains at least one of the following groups in the molecule:

wherein each of R101 to R107 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. k is an integer from 0 to 20 or 1 to 20; k′″ is an integer from 0 to 20. X101 to X108 is selected from C (including CH) or N. Z101 and Z102 is selected from NR101, O, or S.

Non-limiting examples of the host materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564, TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, U.S. Pat. No. 7,154,114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO2007063754, WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO2009086028, WO2010056066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO2012128298, WO2012133644, WO2012133649, WO2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472,

Additional Emitters:

One or more additional emitter dopants may be used in conjunction with the compound of the present disclosure. Examples of the additional emitter dopants are not particularly limited, and any compounds may be used as long as the compounds are typically used as emitter materials. Examples of suitable emitter materials include, but are not limited to, compounds which can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.

Non-limiting examples of the emitter materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554, EP1841834, EP1841834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR20120032054, KR20130043460, TW201332980, U.S. Pat. No. 6,699,599, U.S. Pat. No. 6,916,554, US20010019782, US20020034656, US20030068526, US20030072964, US20030138657, US20050123788, US20050244673, US2005123791, US2005260449, US20060008670, US20060065890, US20060127696, US20060134459, US20060134462, US20060202194, US20060251923, US20070034863, US20070087321, US20070103060, US20070111026, US20070190359, US20070231600, US2007034863, US2007104979, US2007104980, US2007138437, US2007224450, US2007278936, US20080020237, US20080233410, US20080261076, US20080297033, US200805851, US2008161567, US2008210930, US20090039776, US20090108737, US20090115322, US20090179555, US2009085476, US2009104472, US20100090591, US20100148663, US20100244004, US20100295032, US2010102716, US2010105902, US2010244004, US2010270916, US20110057559, US20110108822, US20110204333, US2011215710, US2011227049, US2011285275, US2012292601, US20130146848, US2013033172, US2013165653, US2013181190, US2013334521, US20140246656, US2014103305, U.S. Pat. No. 6,303,238, U.S. Pat. No. 6,413,656, U.S. Pat. No. 6,653,654, U.S. Pat. No. 6,670,645, U.S. Pat. No. 6,687,266, U.S. Pat. No. 6,835,469, U.S. Pat. No. 6,921,915, U.S. Pat. No. 7,279,704, U.S. Pat. No. 7,332,232, U.S. Pat. No. 7,378,162, U.S. Pat. No. 7,534,505, U.S. Pat. No. 7,675,228, U.S. Pat. No. 7,728,137, U.S. Pat. No. 7,740,957, U.S. Pat. No. 7,759,489, U.S. Pat. No. 7,951,947, U.S. Pat. No. 8,067,099, U.S. Pat. No. 8,592,586, U.S. Pat. No. 8,871,361, WO06081973, WO06121811, WO07018067, WO07108362, WO07115970, WO07115981, WO08035571, WO2002015645, WO2003040257, WO2005019373, WO2006056418, WO2008054584, WO2008078800, WO2008096609, WO2008101842, WO2009000673, WO2009050281, WO2009100991, WO2010028151, WO2010054731, WO2010086089, WO2010118029, WO2011044988, WO2011051404, WO2011107491, WO2012020327, WO2012163471, WO2013094620, WO2013107487, WO2013174471, WO2014007565, WO2014008982, WO2014023377, WO2014024131, WO2014031977, WO2014038456, WO2014112450.

HBL:

A hole blocking layer (HBL) may be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device may result in substantially higher efficiencies and/or longer lifetime as compared to a similar device lacking a blocking layer. Also, a blocking layer may be used to confine emission to a desired region of an OLED. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and or higher triplet energy than the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and or higher triplet energy than one or more of the hosts closest to the HBL interface.

In one aspect, compound used in HBL contains the same molecule or the same functional groups used as host described above.

In another aspect, compound used in HBL contains at least one of the following groups in the molecule:

wherein k is an integer from 1 to 20; L101 is an another ligand, k′ is an integer from 1 to 3.

ETL:

Electron transport layer (ETL) may include a material capable of transporting electrons. Electron transport layer may be intrinsic (undoped), or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complexes or organic compounds may be used as long as they are typically used to transport electrons.

In one aspect, compound used in ETL contains at least one of the following groups in the molecule:

wherein R101 is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. Ar1 to Ar3 has the similar definition as Ar's mentioned above. k is an integer from 1 to 20. X101 to X108 is selected from C (including CH) or N.

In another aspect, the metal complexes used in ETL contains, but not limit to the following general formula:

wherein (O—N) or (N—N) is a bidentate ligand, having metal coordinated to atoms O, N or N, N; L101 is another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal.

Non-limiting examples of the ETL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US2011210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, U.S. Pat. No. 6,656,612, U.S. Pat. No. 8,415,031, WO2003060956, WO2007111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535,

Charge Generation Layer (CGL)

In tandem or stacked OLEDs, the CGL plays an essential role in the performance, which is composed of an n-doped layer and a p-doped layer for injection of electrons and holes, respectively. Electrons and holes are supplied from the CGL and electrodes. The consumed electrons and holes in the CGL are refilled by the electrons and holes injected from the cathode and anode, respectively; then, the bipolar currents reach a steady state gradually. Typical CGL materials include n and p conductivity dopants used in the transport layers.

In any above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or fully deuterated. Thus, any specifically listed substituent, such as, without limitation, methyl, phenyl, pyridyl, etc. may be undeuterated, partially deuterated, and fully deuterated versions thereof. Similarly, classes of substituents such as, without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc. also may be undeuterated, partially deuterated, and fully deuterated versions thereof.

EXPERIMENTAL SECTION

Synthesis of the Ligand LA3

In a nitrogen flushed 250 mL two-necked round-bottomed flask, 10,10-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-dibenzo[b,e][1,4]oxasiline (10.5 g, 29.8 mmol), 2-bromopyridine (4.71 g, 29.8 mmol), potassium phosphate tribasic hydrate (13.73 g, 59.6 mmol) and Pd(PPh3)4 (0.344 g, 0.298 mmol) were suspended in a DME (110 ml)/water (5 mL) mixture under nitrogen to give a yellow suspension. The reaction was heated to 100° C. under nitrogen overnight, and cooled down to room temperature. The organic phase was separated, filtered and evaporated. The residue was subjected to column chromatography on silica gel eluted with heptanes/EtOAc 4/1 (v/v), a silica gel column eluted with heptanes/THF 9/1, and a C18 column, eluted with MeCN/water 4/1 (v/v). 2-(10,10-Dimethyl-10H-dibenzo[b,e][1,4]oxasilin-4-yl)pyridine was obtained as clear colorless oil (3.1 g, 34% yield).

Synthesis of Compound 1709, IrLA3(LB1)2

In an oven-dried 250 mL two-necked round-bottomed flask, 2-(10,10-dimethyl-10H-dibenzo[b,e][1,4]oxasilin-4-yl)pyridine (5.74 g, 18.91 mmol) and iridium complex triflate (4.5 g, 6.30 mmol), were suspended in ethanol (25 ml)/methanol (25 ml)/under nitrogen to give a dark yellow suspension. The mixture was stirred at 70° C. for 4 days under nitrogen, after which the suspension was cooled and a yellow solid obtained via filtration. The crude product was purified using column chromatography on silica gel, eluting with a gradient mixture of toluene/heptanes 1/1 (v/v) to toluene 100%, then crystallized from toluene/heptanes, to afford a yellow solid (1.1 g, 21%).

Synthesis of the Ligand LA24

In a nitrogen flushed 250 mL two-necked round-bottomed flask, 10-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenoxazine (9 g, 27.8 mmol), 2-bromopyridine (5.28 g, 33.4 mmol), potassium phosphate tribasic hydrate (12.83 g, 55.7 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.644 g, 0.557 mmol) were dissolved in a DME (120 ml)/water (3 mL) mixture under nitrogen to give a yellow suspension. The reaction was heated under nitrogen for 14 h, then cooled down to room temperature. The organic phase was separated and evaporated; the residue was subjected to column chromatography on silica gel, eluted with heptanes/THF 9/1 to 4/1 (v/v) gradient mixture, providing after evaporation a green-yellow fluorescent oil (6.4 g, 84%).

Synthesis of the Ligand LA5

2-(9,9-dimethyl-9H-xanthen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6 g, 17.84 mmol), 2-chloropyridine (2.026 g, 17.84 mmol), 2-chloropyridine 4 (5.67 g, 53.5 mmol) were added to DME (30 ml) and water (7.50 ml). The mixture was degassed with N2. Tetrakis(triphenylphosphine)palladium(0) (0.619 g, 0.535 mmol) was added and the mixture was heated under N2 at 100° C. overnight. After the reaction was cooled to rt, it was extracted with EtOAc. The combined organic phase was washed with brine. The solvent was removed. The residue was coated on Celite and purified on a silica gel column eluted with 3% EtOAc in DCM to yield 5 g (90%).

Synthesis of Compound 2566, IrLA5(LB428)2

Iridium complex triflate (2.0 g) and 2-(9,9-dimethyl-9H-xanthen-4-yl)pyridine (1.844 g, 6.42 mmol) was added to a MeOH (25 ml)/EtOH (25 ml) mixture. The reaction mixture was degassed for 20 mins under N2. The mixture was heated to reflux (80° C.) under N2 for 48 h. After the reaction was cooled down to room temperature, excess MeOH was added. The orange solid was filtered, dried, coated on silica gel, and purified on a silica gel column, eluting with a mixture of DCM and heptane (7/3, v/v), to yield 1.0 g (45%) of the target product.

Synthesis of Compound 2568, IrLA5(LB430)2

Iridium complex triflic salt (2.2 g) and 2-(9,9-dimethyl-9H-xanthen-4-yl)pyridine (1.940 g, 6.75 mmol) were added to a MeOH (25 ml)/EtOH (25 ml) mixture. The reaction mixture was degassed for 20 minutes under N2. The mixture was heated to reflux (80° C.) under N2 for 63 h. After the reaction was cooled down to room temperature, excess MeOH was added. The orange solid was filtered off, dried, coated on silica gel, and purified on a silica gel column, eluting with a mixture of DCM and heptane (7/3, v/v), to yield 1.0 g (42%) of the target material.

It is understood that the various embodiments described herein are by way of example only, and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be substituted with other materials and structures without deviating from the spirit of the invention. The present invention as claimed may therefore include variations from the particular examples and preferred embodiments described herein, as will be apparent to one of skill in the art. It is understood that various theories as to why the invention works are not intended to be limiting.

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Patents Cited in This Cited by
Title Current Assignee Application Date Publication Date
Composition for charge-transporting film and ion compound, charge-transporting film and organic electroluminescent device using same, and method for manufacturing organic electroluminescent device and method for producing charge-transporting film MITSUBISHI CHEMICAL CORPORATION 07 March 2005 22 November 2006
有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 コニカミノルタ株式会社 21 September 2006 03 April 2008
有機エレクトロルミネッセンス素子、表示装置及び照明装置 コニカミノルタホールディングス株式会社 26 October 2005 17 May 2007
Metal coordination compound, luminescence device and display apparatus CANON KABUSHIKI KAISHA 07 March 2002 11 September 2002
Condensed cyclic compound and organic light-emitting device including the same SAMSUNG ELECTRONICS CO., LTD.,SAMSUNG SDI CO., LTD. 24 March 2015 03 February 2016
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US10153443 Organic electroluminescent materials devices 1 US10153443 Organic electroluminescent materials devices 2 US10153443 Organic electroluminescent materials devices 3