IP Library › Granted Patent US 11,335,860
Granted Patent B2
US 11,335,860 · App. 16/413,536 · Granted May 17, 2022

Organic electroluminescence device and condensed cyclic compound for organic electroluminescence device

Inventor: Takuya Uno (Yokohama, JP)
Assignee: Samsung Display Co., Ltd.
H01L51/0072C07D471/22C07D487/16C07D491/22C07D495/22H01L51/006H01L51/0054H01L51/0061H01L51/0073H01L51/0074H01L51/5012H01L51/5092H01L51/5096H01L51/5056H01L51/5072
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Quick Facts
Patent No.
US 11,335,860
App. No.
16/413,536
Granted
May 17, 2022
Kind
B2
Abstract

An organic electroluminescence device of an embodiment includes a first electrode and a second electrode facing each other, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one organic layer includes a condensed cyclic compound represented by Formula 1, thereby showing improved device efficiency and life.

Claims (59)

1. An organic electroluminescence device, comprising:

a first electrode;

a second electrode disposed on the first electrode; and

a plurality of organic layers disposed between the first electrode and the second electrode,

wherein the plurality of organic layers comprise an emission layer,

wherein the emission layer comprises at least one of anthracene derivatives, pyrene derivatives, fluoranthene derivatives, chrysene derivatives, dihydro benzanthracene derivatives, or triphenylene derivatives,

wherein at least one organic layer among the plurality of organic layers comprises a condensed cyclic compound represented by the following Formula 1:

in Formula 1,

each of Ar1, Ar2, and Ar3 is independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms for forming a ring,

excluding a case where one or both of Ar2 or Ar3 is a substituted or unsubstituted carbazole group,

each of X1, X2, and X3 is independently *-L-NR 1 R 2 ,

one of a1, a2, and a3 is 1 and the others are 0,

L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring, and

each of R 1 and R 2 is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms for forming a ring, or combined with each other to form a ring.

2. The organic electroluminescence device of claim 1 , wherein the plurality of organic layers further comprise:

a hole transport region disposed between the first electrode and the emission layer,

wherein the hole transport region comprises the condensed cyclic compound represented by Formula 1.

3. The organic electroluminescence device of claim 2 , wherein the emission layer emits blue light.

4. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by the following Formula 1-1 or Formula 1-2:

in Formula 1-1 and Formula 1-2, Ar1, Ar2, Ar3, L, R 1 and R 2 are the same as defined in Formula 1.

5. The organic electroluminescence device of claim 1 , wherein Ar1 is a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.

6. The organic electroluminescence device of claim 1 , wherein each of Ar2 and Ar3 is independently a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted pyridine ring, or a substituted or unsubstituted quinoline ring.

7. The organic electroluminescence device of claim 1 , wherein Ar2 and Ar3 are the same.

8. The organic electroluminescence device of claim 1 , wherein each of Ar2 and Ar3 is independently represented by any one of the following Ar-a to Ar-i:

in Ar-a to Ar-i,

each of R 11 to R 19 is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring,

each of a11 to a19 is independently an integer of 0 to 4, and

dotted lines represent combined parts forming a condensed ring.

9. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by the following Formula 2-1 or Formula 2-2:

in Formula 2-1 and Formula 2-2,

each of R 3 and R 4 is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring,

“y” and “z” are each independently an integer of 0 to 3, and

X1 to X3, and a1 to a3 are the same as defined in Formula 1.

10. The organic electroluminescence device of claim 1 , wherein at least one organic layer comprises at least one of compounds represented in the following Compound Group 1 and Compound Group 2:

11. A condensed cyclic compound represented by the following Formula 1:

in Formula 1,

each of Ar1, Ar2, and Ar3 is independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms for forming a ring,

excluding a case where one or both of Ar2 and Ar3 is a substituted or unsubstituted carbazole group,

each of X1, X2, and X3 is independently *-L-NR 1 R 2 , and is bonded to a carbon atom of a respective one of the Ar1, Ar2, and Ar3,

any one of a1, a2, and a3 is 1, and the others are 0,

L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring, and

Each of R 1 and R 2 is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms for forming a ring, or combined with each other to form a ring.

12. The condensed cyclic compound of claim 11 , wherein Formula 1 is represented by the following Formula 1-1 or Formula 1-2:

in Formula 1-1 and Formula 1-2, Ar1 to Ar3, L, R 1 and R 2 are the same as defined in Formula 1.

13. The condensed cyclic compound of claim 11 , wherein Ar1 is a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.

14. The condensed cyclic compound of claim 11 , wherein each of Ar2 and Ar3 is independently a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted pyridine ring, or a substituted or unsubstituted quinoline ring.

15. The condensed cyclic compound of claim 11 , wherein Ar2 and Ar3 are the same.

16. The condensed cyclic compound of claim 11 , wherein each of Ar2 and Ar3 is independently represented by any one of the following Ar-a to Ar-i:

in Ar-a to Ar-i,

each of R 11 to R 19 is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring,

each of all to a19 is independently an integer of 0 to 4, and

dotted lines represent combined parts forming a condensed ring.

17. The condensed cyclic compound of claim 11 , wherein Formula 1 is represented by the following Formula 2-1 or Formula 2-2:

in Formula 2-1 and Formula 2-2,

each of R 3 and R 4 is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, or combined with an adjacent group to form a ring,

each of “y” and “z” is independently an integer of 0 to 3, and

X1, X2, X3, a1, a2, and a3 are the same as defined in Formula 1.

18. The condensed cyclic compound of claim 11 , wherein L is a direct linkage or represented by any one of the following L1, L2, L3, and L4:

19. A condensed cyclic compound represented by any of the compounds represented in the following Compound Group 1 and Compound Group 2:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 15, 2019
From: UNO, TAKUYA
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 049189/0728 →
Priority Claims (1)
KR 10-2018-0063453 · Jun 1, 2018 · national
Continuity (1)
Related Publication 20190372019A1 · Dec 5, 2019
Cited By (1)
US 12,426,499