IP Library › Granted Patent US 11,230,521
Granted Patent B2
US 11,230,521 · App. 15/921,936 · Granted Jan 25, 2022

Monoamine compound and organic electroluminescence device including the same

Inventors: Ichinori Takada (Yokohama, JP); Takuya Uno (Yokohama, JP); Xiulan Jin (Yokohama, JP)
Assignee: Samsung Display Co., Ltd.
C07C211/54C07D307/91C07D333/76C07F7/0805C09K11/06H01L51/006H01L51/0059H01L51/0061H01L51/0072H01L51/0073H01L51/0074H01L51/0094H01L51/5056H01L51/5072C07C2603/26C09K2211/1007C09K2211/1011C09K2211/1088C09K2211/1092
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Quick Facts
Patent No.
US 11,230,521
App. No.
15/921,936
Granted
Jan 25, 2022
Kind
B2
Abstract

An monoamine compound and an organic electroluminescence device including the monoamine compound, the monoamine compound being represented by the following Formula 1:

Claims (64)

1. A monoamine compound represented by the following Formula 1:

wherein, in Formula 1,

Ar 1 is a group represented by the following Formula 2,

Ar 2 and Ar 3 are each independently a group represented by the following Formula 2, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

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 2 to 30 ring carbon atoms,

wherein, in Formula 2,

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 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

R 1 to R 4 are separate or form a ring by combining adjacent groups with each other,

l is 0 or 1,

m, n, and o are each independently an integer of 0 to 4, and

p is an integer of 0 to 5,

wherein at least one selected from Ar 1 , Ar 2 and Ar 3 is different from at least an other one selected from Ar 1 , Ar 2 and Ar 3 , and

wherein when L 1 to L 3 are each independently a direct linkage, and one selected from Ar 2 and Ar 3 is a group represented by Ar-18, an other one selected from Ar 2 and Ar 3 is a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group derived from an aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or the group represented by Ar-18,

wherein in Ar-18, * is a bonding location,

wherein in Ar 1 represented by Formula 2, when R 1 to R 4 are each a hydrogen atom, l is 1, and

wherein the monoamine compound represented by Formula 1 is a single amine group compound.

2. The monoamine compound as claimed in claim 1 , wherein the compound represented Formula 1 is represented by the following Formula 1-1, 1-2 or 1-6:

wherein, in Formulae 1-1, 1-2 and 1-6, Ar 2 , Ar 3 , L 1 to L 3 , R 1 to R 4 , and l to p are defined the same as those of Formula 1.

3. The monoamine compound as claimed in claim 1 , wherein the compound represented Formula 1 is represented by one of the following Formulae 1-3 to 1-5:

wherein, in Formulae 1-3 to 1-5, Ar 2 , Ar 3 , L 1 to L 3 , R 1 to R 4 , and l to p are defined the same as those of Formula 1.

4. The monoamine compound as claimed in claim 1 , wherein the group represented by Formula 2 is a group represented by one of the following Ar-1 to Ar-7 and Ar-9 to Ar-10, in which * is a bonding location:

5. The monoamine compound as claimed in claim 1 , wherein Ar 2 and Ar 3 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthryl group.

6. The monoamine compound as claimed in claim 1 , wherein Ar 2 and Ar 3 are each independently a group represented by one of the following Ar-11 to Ar-16, in which * is a bonding location:

7. The monoamine compound as claimed in claim 1 , wherein Ar 2 and Ar 3 are each independently a substituted or unsubstituted heteroaryl group that includes O or S as a heteroatom.

8. The monoamine compound as claimed in claim 1 , wherein Ar 2 and Ar 3 are each independently a group represented by the following Ar-17 or Ar-18, which * is a bonding location:

9. The monoamine compound as claimed in claim 1 , wherein Ar 2 and Ar 3 are each independently a substituted or unsubstituted triphenylsilyl group.

10. The monoamine compound as claimed in claim 1 , wherein L 1 to L 3 are each independently a direct linkage or a substituted or unsubstituted phenylene group.

11. A compound of the following Compound Group 1:

12. An organic electroluminescence device, comprising:

a first electrode;

an organic layer on the first electrode, the organic layer including a hole transport region, an emission layer, and an electron transport region; and

a second electrode on the organic layer,

wherein the organic layer includes a monoamine compound represented by the following Formula 1:

wherein, in Formula 1,

Ar 1 is a group represented by the following Formula 2,

Ar 2 and Ar 3 are each independently a group represented by the following Formula 2, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,

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 2 to 30 ring carbon atoms,

wherein, in Formula 2,

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 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

R 1 to R 4 are separate or form a ring by combining adjacent groups with each other,

l is 0 or 1,

m, n, and o are each independently an integer of 0 to 4, and

p is an integer of 0 to 5,

wherein at least one selected from Ar 1 , Ar 2 and Ar 3 is different from at least an other one selected from Ar 1 , Ar 2 and Ar 3 , and

wherein when L 1 to L 3 are each independently a direct linkage, and one selected from Ar 2 and Ar 3 is a group represented by Ar-18, an other one selected from Ar 2 and Ar 3 is a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group derived from an aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or the group represented by Ar-18,

wherein in Ar-18, * is a bonding location,

wherein in Ar 1 represented by Formula 2, when R 1 to R 4 are each a hydrogen atom, l is 1, and

wherein the monoamine compound represented by Formula 1 is a single amine group compound.

13. The organic electroluminescence device as claimed in claim 12 , wherein the hole transport region includes the monoamine compound represented by Formula 1.

14. The organic electroluminescence device as claimed in claim 12 , wherein the emission layer emits blue light.

15. The organic electroluminescence device as claimed in claim 12 , wherein the compound represented Formula 1 is represented by the following Formula 1-1, 1-2 or 1-6:

wherein, in Formulae 1-1, 1-2 and 1-6, Ar 2 , Ar 3 , L 1 to L 3 , R 1 to R 4 , and l to p are defined the same as those of Formula 1.

16. The organic electroluminescence device as claimed in claim 12 , wherein the compound represented Formula 1 is represented by one of the following Formulae 1-3 to 1-5:

wherein, in Formulae 1-3 to 1-5, Ar 2 , Ar 3 , L 1 to L 3 , R 1 to R 4 , and l to p are defined the same as those of Formula 1.

17. The organic electroluminescence device as claimed in claim 12 , wherein the group represented by Formula 2 is a group represented by one of the following Ar-1 to Ar-7 and Ar-9 to Ar-10, in which * is a bonding location:

18. The organic electroluminescence device as claimed in claim 12 , wherein Ar 2 and Ar 3 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted heteroaryl group that includes O or S as a heteroatom.

19. The organic electroluminescence device as claimed in claim 12 , wherein L 1 to L 3 are each independently a direct linkage or a substituted or unsubstituted phenylene group.

20. An organic electroluminescence device, comprising:

a first electrode;

an organic layer on the first electrode, the organic layer including a hole transport region, an emission layer, and an electron transport region; and

a second electrode on the organic layer,

wherein the organic layer includes a monoamine compound,

the hole transport region includes the monoamine compound, and

the monoamine compound is a compound of the following Compound Group 1:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 15, 2018
From: TAKADA, ICHINORI; UNO, TAKUYA; JIN, XIULAN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 045231/0377 →
Priority Claims (1)
KR 10-2017-0097827 · Aug 1, 2017 · national
Continuity (1)
Related Publication 20190039996A1 · Feb 7, 2019