IP Library › Granted Patent US 10,840,459
Granted Patent B2
US 10,840,459 · App. 15/962,543 · Granted Nov 17, 2020

Organic electroluminescent materials and devices

Inventors: Chun Lin (Yardley, PA); Zhiqiang Ji (Hillsborough, NJ); Bin Ma (Plainsboro, NJ)
Assignee: Universal Display Corporation
H01L51/0072C07D519/00C09K11/025C09K11/06H01L51/0085C09K2211/1029C09K2211/185H01L51/5016H01L51/5056H01L51/5072H01L51/5096H01L2251/5384
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Quick Facts
Patent No.
US 10,840,459
App. No.
15/962,543
Granted
Nov 17, 2020
Kind
B2
Abstract

A compound having a formula selected from the group consisting of: is disclosed. In these structures, each one of A 1 to A 16 is N or C bonded to the applicable one of R 1 , R 2 , R 3 , and R 4 ; ring A and ring B are joined by a C—C bond; each R 1 to R 6 is independently hydrogen or a variety of substituents; and any two of R 1 to R 6 are optionally joined or fused into a ring, provided that the following compound is excluded: Organic light emitting devices and consumer products containing the compounds are also disclosed.

Claims (50)

1. A compound having a formula selected from the group consisting of:

wherein R 1 , R 2 , R 3 , and R 4 each independently represent no substitutions up to a maximum number of possible substitutions;

wherein each one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , A 10 , A 11 , A 12 , A 13 , A 14 , A 15 , and A 16 is independently N or C bonded to the applicable one of R 1 , R 2 , R 3 , and R 4 ;

wherein ring A and ring B are joined by a C—C bond;

wherein each R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 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

wherein any two of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are optionally joined or fused into a ring, provided that the following compound is excluded:

2. The compound of claim 1 , wherein the compound is selected from the group consisting of:

3. The compound of claim 1 , wherein at least one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , A 10 , A 11 , A 12 , A 13 , A 14 , A 15 , and A 16 is nitrogen.

4. The compound of claim 1 , wherein at least one of adjacent pair of R 1 , R 2 , R 3 , and R 4 is joined to form a fused ring.

5. The compound of claim 1 , wherein R 5 and R 6 are the same.

6. The compound of claim 1 , wherein R 5 and R 6 are different.

7. The compound of claim 1 , wherein at least one of R 5 and R 6 comprises a group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-variants thereof, and combination thereof.

8. The compound of claim 1 , wherein at least one of R 5 and R 6 comprises a group selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, benzimidazole, imidazole, quinoline, isoquinoline, quinazoline, quinoxaline, dibenzoquinazoline and dibenzo quinoxaline.

9. The compound of claim 1 , wherein each one of R 5 and R 6 is independently aryl or heteroaryl.

10. The compound of claim 1 , wherein R 5 and R 6 are selected from the group consisting of biphenyl, o-terphenyl, m-terphenyl, and p-terphenyl.

11. The compound of claim 1 , wherein R 5 and R 6 are each independently selected from the group consisting of:

and any combination thereof;

wherein X, X′, and X″ is selected from the group consisting of O, S, Se, C(CH 3 ) 2 and N-Ph;

wherein X 1 to X 12 are each independently selected from the group consisting of CH and N.

12. The compound of claim 1 , wherein each R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof.

13. The compound of claim 1 , wherein the compound is selected from the group consisting of:

14. A formulation comprising a compound according to claim 1 .

15. 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 having a formula selected from the group consisting of:

wherein R 1 , R 2 , R 3 , and R 4 each independently represent no substitutions up to a maximum number of possible substitutions;

wherein each one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , A 10 , A 11 , A 12 , A 13 , A 14 , A 15 , and A 16 is independently N or C bonded to the applicable one of R 1 , R 2 , R 3 , and R 4 ;

wherein ring A and ring B are joined by a C—C bond;

wherein each R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 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

wherein any two of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are optionally joined or fused into a ring, provided that the following compound is excluded:

16. The OLED of claim 15 , wherein the organic layer is an emissive layer and the compound of Formula I is a host.

17. The OLED of claim 15 , wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the emissive dopant is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:

wherein each Y 1 to Y 13 are independently selected from the group consisting of carbon and nitrogen;

wherein Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═0, S═0, SO 2 , CR e R f , SiR e R f , and GeR e R f ;

wherein R e and R f are optionally fused or joined to form a ring;

wherein each R a , R b , R c , and R d may independently represent from mono substitution to the maximum possible number of substitution, or no substitution;

wherein each R a , R b , R c , R d , R e and R f is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof; and

wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

18. The OLED of claim 15 , wherein the organic layer is a blocking layer and the compound of Formula I is a blocking material in the organic layer, or the organic layer is a transporting layer and the compound of Formula I is a transporting material in the organic layer.

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 having a formula selected from the group consisting of:

wherein R 1 , R 2 , R 3 , and R 4 each independently represent no substitutions up to a maximum number of possible substitutions;

wherein each one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , A 10 , A 11 , A 12 , A 13 , A 14 , A 15 , and A 16 is independently N or C bonded to the applicable one of R 1 , R 2 , R 3 , and R 4 ;

wherein ring A and ring B are joined by a C—C bond;

wherein each R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 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

wherein any two of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are optionally joined or fused into a ring, provided that the following compound is excluded:

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 walls comprising multiple displays tiled together, a theater or stadium screen, and a sign.

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded Apr 27, 2018
From: LIN, CHUN; JI, ZHIQIANG; MA, BIN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 045657/0123 →
Continuity (2)
Provisional Application 62507842 · May 18, 2017
Related Publication 20180337344A1 · Nov 22, 2018