IP Library Granted Patent US 11,440,901
Granted Patent B2
US 11,440,901 · App. 16/568,516 · Granted Sep 13, 2022

Composition of matter for use in organic light-emitting diodes

Inventors: YuSeok Yang (Fukuoka, JP); Yong Joo Cho (Fukuoka, JP); Yoshitake Suzuki (Fukuoka, JP); Shuo-Hsien Cheng (Fukuoka, JP); Jorge Aguilera-Iparraguirre (Roslindale, MA)
Assignee: KYULUX, INC.
C07D403/14C07D413/14C07D417/14C07D471/04C07D487/04C07F7/0816H01L51/0059H01L51/0067H01L51/0069H01L51/0072H01L51/0094H01L51/5206H01L51/5221
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Quick Facts
Patent No.
US 11,440,901
App. No.
16/568,516
Granted
Sep 13, 2022
Kind
B2
Abstract

The present disclosure relates to compounds of Formula (1) as useful materials for OLEDs. A is CN, cyanoaryl, or heteroaryl having at least one nitrogen atom as a ring-constituting atom; and D 1 , D 2 and D 3 are diarylamino or carbazolyl.

Claims (30)

1. A compound of Formula (I):

wherein:

A is selected from CN, aryl that is substituted with at least one cyano, and a group represented by Formula (III):

wherein:

one of X 1 , X 2 and X 3 is N,

the other two of X 1 , X 2 and X 3 are independently N or C(R 13 ),

R 11 , R 12 and R 13 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl, and

* represents a point of attachment to Formula (I); and

D 1 , D 2 and D 3 are independently selected from substituted or unsubstituted 1-carbazolyl, substituted or unsubstituted 2-carbazolyl, substituted or unsubstituted 3-carbazolyl, substituted or unsubstituted 4-carbazolyl, and group represented by Formula (II):

wherein:

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; or two or more instances of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 taken together can form a ring system, or R 5 and R 6 taken together can form single bond, and

L 1 is selected from single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene.

2. The compound of claim 1 , wherein D 1 , D 2 and D 3 are the same.

3. The compound of claim 1 , wherein two of D 1 , D 2 and D 3 are the same.

4. The compound of claim 1 , wherein D 1 and D 3 are the same.

5. The compound of claim 1 , wherein at least one of D 1 , D 2 and D 3 has at least one carbazole ring.

6. The compound of claim 5 , wherein the carbazole ring is substituted by at least one selected from substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl.

7. The compound of claim 5 , wherein the carbazole ring is substituted at 3-position, 6-position, or 3- and 6-positions.

8. The compound of claim 1 , wherein R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , or R 4 and R 5 are taken together to form a ring system.

9. The compound of claim 1 , wherein at least one of R 1 , R 2 , R 3 and R 4 is substituted or unsubstituted carbazolyl.

10. The compound of claim 1 , wherein A is CN.

11. The compound of claim 1 , wherein when D 1 , D 2 and D 3 are independently substituted or unsubstituted 9-carbazolyl, then A is substituted or unsubstituted cyanoaryl, or group represented by Formula (III).

12. The compound of claim 1 , wherein when D 1 , D 2 and D 3 are independently substituted or unsubstituted 9-carbazolyl, and A is cyano, then all of D 1 , D 2 and D 3 are not the same.

13. The compound of claim 1 , wherein when D 1 , D 2 and D 3 are independently substituted or unsubstituted 9-carbazolyl, and A is cyano, then at least one of D 1 , D 2 and D 3 is 9-carbazolyl substituted with at least one selected from substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl.

14. An organic light-emitting diode (OLED) comprising the compound of claim 1 .

15. An organic light-emitting diode (OLED) of claim 14 , wherein light emission of the OLED occurs mainly in the compound.

16. The organic light-emitting diode (OLED) of claim 14 , comprising an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises a host material and the compound.

17. The organic light-emitting diode (OLED) of claim 14 , comprising an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises the compound and a light-emitting material, and light emission of the OLED occurs mainly in the light-emitting material.

18. The organic light-emitting diode (OLED) of claim 14 , comprising an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises a host material, an assistant dopant and a light-emitting material, and the assistant dopant is the compound.

19. A screen or a display comprising the compound of claim 1 .

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 4, 2020
From: AGUILERA-IPARRAGUIRRE, JORGES
To: KYULUX NORTH AMERICA, INC.
Reel/Frame 051714/0210 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ADDING INVENTOR'S NAME PREVIOUSLY RECORDED AT REEL: 050957 FRAME: 0121. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Feb 4, 2020
From: YANG, YUSEOK; CHO, YONG JOO; SUZUKI, YOSHITAKE; CHENG, SHUO-HSIEN
To: KYULUX, INC.
Reel/Frame 051795/0371 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2019
From: CHO, YONG JOO; SUZUKI, YOSHITAKE; CHENG, SHUO-HSIEN
To: KYULUX NORTH AMERICA, INC.
Reel/Frame 050957/0121 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2019
From: KYULUX NORTH AMERICA, INC.
To: KYULUX, INC.
Reel/Frame 050957/0279 →
Continuity (3)
Provisional Application 62730131 · Sep 12, 2018
Provisional Application 62730178 · Sep 12, 2018
Related Publication 20200079760A1 · Mar 12, 2020
Cited By (1)
US 12,685,012