IP Library › Granted Patent US 10,069,081
Granted Patent B2
US 10,069,081 · App. 15/586,997 · Granted Sep 4, 2018

Organic electroluminescent materials and devices

Inventors: Chuanjun Xia (Lawrenceville, NJ); Chun Lin (Yardley, PA); Raymond Kwong (Fo Tan, HK); Scott Joseph (Ewing, NJ); James Esler (Yardley, PA)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0067C07D403/10C07D405/14C07D409/14C07D491/048C07D493/04C07D495/04C09K11/06H01L51/006H01L51/0054H01L51/0061H01L51/0072H01L51/0073H01L51/0074C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1059C09K2211/1088C09K2211/1092H01L51/5012H01L2251/5376
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Quick Facts
Patent No.
US 10,069,081
App. No.
15/586,997
Granted
Sep 4, 2018
Kind
B2
Abstract

Devices containing novel carbazole-containing compounds are provided. The novel compounds also contain electron donor groups, aryl linkers, and at least one nitrogen heterocycle. These novel organic compounds can exhibit delayed fluorescence in the devices.

Claims (45)

1. A first device comprising a first organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer, disposed between the anode and the cathode;

wherein the emissive layer comprises a compound having the formula:

wherein Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are each independently selected from group consisting of CR 9 and N;

wherein any adjacent R 9 are optionally joined to form a fused ring;

wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is N;

wherein L 1 is selected from the group consisting of:

and combinations thereof;

wherein X 1 is O, S, or CRR′;

wherein R, R′ are optionally joined to form a ring;

wherein n 1 is an integer from 1 to 20;

wherein L 1 can be further substituted by a substituent selected from the group consisting of alkyl, aryl, and heteroaryl;

wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group selected from the group consisting of:

wherein X and Y is selected from the group consisting of O, S, NR 14 ; and

wherein R 11 , R 12 , R 13 and R 14 are selected from the group consisting of aryl and heteroaryl;

wherein any two adjacent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are not joined to form a ring;

wherein m is an integer from 1 to 20;

wherein n 2 is an integer from 1 to 20;

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 do not contain an electron acceptor group;

wherein R 9 does not contain an electron donor group;

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof;

wherein R 9 , R, and R′ are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof; and

wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is CR 9 wherein R 9 is selected from aryl and heteroaryl, and can be further substituted.

2. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises the electron donor group selected from the group consisting of:

3. The first device of claim 1 , wherein the compound has the formula:

and

wherein R 91 and R 92 are independently selected from aryl or heteroaryl, and can be further substituted.

4. The first device of claim 1 , wherein the electron donor group is selected from the group consisting of:

5. The first device of claim 1 , wherein the compound is selected from the group consisting of:

6. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure

7. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure

8. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure

9. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure

10. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure

11. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure

12. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure

13. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure

14. The first device of claim 1 , wherein L 1 is

15. The first device of claim 1 , wherein L 1 is

16. The first device of claim 1 , wherein L 1 is

17. The first device of claim 1 , wherein L 1 is

18. The first device of claim 1 , wherein L 1 is

19. The first device of claim 1 , wherein the first device is a consumer product selected from the group consisting of flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, vehicles, a large area wall, theater or stadium screen, and a sign.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 8, 2017
From: XIA, CHUANJUN; LIN, CHUN; KWONG, RAYMOND; JOSEPH, SCOTT; ESLER, JAMES
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 042271/0763 →
Continuity (3)
Continuation 14921446 · Oct 23, 2015
Division 13708189 · Dec 7, 2012
Related Publication 20170237014A1 · Aug 17, 2017