IP Library › Granted Patent US 9,670,185
Granted Patent B2
US 9,670,185 · App. 14/921,446 · Granted Jun 6, 2017

Organic electroluminescent materials and devices

Inventors: Chuanjun Xia (YLawrenceville, NJ); Chun Lin (Yardley, PA); Raymond Kwong (Fo Tan, HK); Scott Joseph (Ewing, NJ); James Esler (Yardley, PA)
Assignee: UNIVERSAL DISPLAY CORPORATION
C07D403/14C07D403/10C07D405/14C07D409/14C07D491/048C09K11/06H01L51/0067H01L51/0072C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092H01L51/0054H01L51/0073
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Quick Facts
Patent No.
US 9,670,185
App. No.
14/921,446
Granted
Jun 6, 2017
Kind
B2
Abstract

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 are useful in OLED devices and can exhibit delayed fluorescence.

Claims (41)

1. 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; and

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; wherein at least one 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 compound 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 compound 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 compound of claim 1 , wherein the electron donor group is selected from the group consisting of:

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

6. The compound 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 compound 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 compound 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 compound 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 compound 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 compound 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 compound 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 compound 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 compound 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

15. The compound of claim 1 , wherein L 1 is

16. The compound of claim 1 , wherein L 1 is

17. The compound of claim 1 , wherein L 1 is

18. The compound of claim 1 , wherein L 1 is

19. The compound of claim 1 , wherein L 1 is

20. The compound of claim 1 , wherein L 1 is

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 26, 2015
From: XIA, CHUANJUN; LIN, CHUN; KWONG, RAYMOND; JOSEPH, SCOTT; ESLER, JAMES
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 036881/0270 →
Continuity (2)
Division 13708189 · Dec 7, 2012
Related Publication 20160060251A1 · Mar 3, 2016