IP Library › Granted Patent US 11,502,257
Granted Patent B2
US 11,502,257 · App. 16/654,608 · Granted Nov 15, 2022

Organic electroluminescence device and amine compound for organic electroluminescence device

Inventors: Ichiro Imada (Yokohama, JP); Ichinori Takada (Yokohama, JP)
Assignee: Samsung Display Co., Ltd.
H01L51/0059H01L51/0052H01L51/0072H01L51/0073H01L51/0074H01L51/0094
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Quick Facts
Patent No.
US 11,502,257
App. No.
16/654,608
Granted
Nov 15, 2022
Kind
B2
Abstract

Provided are an organic electroluminescence device including an amine compound represented by Formula 1 in at least one of a plurality of organic layers and an amine compound represented by Formula 1.

Claims (47)

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, at least one of the organic layers including an amine compound represented by Formula 1:

where L 1 to L 3 are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms,

1, m, and n are each independently 1 or 2,

Ar 1 to Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, or a group represented by Formula 2, provided that at least one of Ar 1 to Ar 3 is the group represented by Formula b 2 :

where X is CR 2 R 3 or NR 4 ,

R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 ring carbon atoms, or form a ring by combining adjacent groups with each other,

p is an integer of 1 to 12, and

q is 1 or 2.

2. The organic electroluminescence device as claimed in claim 1 , wherein Formula 2 is represented by Formula 3-1 or 3-2:

where R 1 to R 4 , and q are the same as defined in Formula 2.

3. The organic electroluminescence device as claimed in claim 2 , wherein R 1 to R 4 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 ring carbon atoms, and q is the same as defined in Formula 2.

4. The organic electroluminescence device as claimed in claim 3 , wherein R 1 to R 4 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

5. The organic electroluminescence device as claimed in claim 1 , wherein L 1 to L 3 are each independently a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted fluorenylene group.

6. The organic electroluminescence device as claimed in claim 1 , wherein Ar 1 to Ar 3 are each independently the group represented by Formula 2, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

7. The organic electroluminescence device as claimed in claim 1 , wherein Ar 1 to Ar 3 are each independently:

the group represented by Formula 2,

an aryl group substituted with a methyl group, an aryl group substituted with an unsubstituted phenyl group, or an aryl group substituted with a triphenylsilyl group, or

a heteroaryl group substituted with a methyl group, a heteroaryl group substituted with an unsubstituted phenyl group, or a heteroaryl group substituted with a triphenylsilyl group.

8. The organic electroluminescence device as claimed in claim 1 , wherein one or two from Ar 1 to Ar 3 are represented by Formula 2.

9. The organic electroluminescence device as claimed in claim 1 , wherein the organic layers include:

a hole transport region disposed on the first electrode;

an emission layer disposed on the hole transport region; and

an electron transport region disposed on the emission layer, and

the hole transport region includes the amine compound represented by Formula 1.

10. The organic electroluminescence device as claimed in claim 1 , wherein the amine compound is a compound selected from Compound Group 1:

11. An amine compound represented by Formula 1:

where L 1 to L 3 are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms,

l, m, and n are each independently 1 or 2,

Ar 1 to Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, or a group represented by Formula 2, provided that at least one of Ar 1 to Ar 3 is the group represented by Formula 2:

where X is CR 2 R 3 or NR 4 ,

R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 ring carbon atoms, or form a ring by combining adjacent groups with each other,

p is an integer of 1 to 12, and

q is 1 or 2.

12. The amine compound as claimed in claim 11 , wherein Formula 2 is represented by Formula 3-1 or 3-2:

where R 1 to R 4 , and q are the same as defined in Formula 2.

13. The amine compound as claimed in claim 12 , wherein R 1 to R 4 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 ring carbon atoms, and q is the same as defined in Formula 2.

14. The amine compound as claimed in claim 12 , wherein R 1 to R 4 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

15. The amine compound as claimed in claim 12 , wherein Formula 3-1 is represented by Formula 4-1-1 or 4-1-2, and Formula 3-2 is represented by Formula 4-2:

where R 1 , R 2 , R 4 and q are the same as defined in Formulae 3-1 and 3-2.

16. The amine compound as claimed in claim 11 , wherein L 1 to L 3 are each independently a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted fluorenylene group.

17. The amine compound as claimed in claim 11 , wherein Ar 1 to Ar 3 are each independently the group represented by Formula 2, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

18. The amine compound as claimed in claim 11 , wherein Ar 1 to Ar 3 are each independently the group represented by Formula 2, an aryl group substituted with a methyl group, an unsubstituted phenyl group, or a triphenylsilyl group, or a heteroaryl group substituted with a methyl group, an unsubstituted phenyl group, or a triphenylsilyl group.

19. The amine compound as claimed in claim 11 , wherein one or two of Ar 1 to Ar 3 are represented by Formula 2.

20. The amine compound as claimed in claim 11 , wherein the amine compound is a compound selected from Compound Group 1:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 16, 2019
From: IMADA, ICHIRO; TAKADA, ICHINORI
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 050735/0995 →
Priority Claims (1)
KR 10-2018-0124547 · Oct 18, 2018 · national
Continuity (1)
Related Publication 20200127208A1 · Apr 23, 2020