IP Library Granted Patent US 11,038,111
Granted Patent B2
US 11,038,111 · App. 16/200,412 · Granted Jun 15, 2021

Organic electroluminescence device and monoamine compound for organic electroluminescence device

Inventors: Ichinori Takada (Tsurumi-ku, JP); Ichiro Imada (Tsurumi-ku, JP)
Assignee: Samsung Display Co., Ltd.
H01L51/006C07C211/54C07D307/91C07D333/76C07F7/081C09K11/06H01L51/0061C07C2603/26C07C2603/74C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1018H01L51/0052H01L51/0073H01L51/0074H01L51/5012H01L51/5016H01L51/5056H01L51/5088H01L51/5096
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,038,111
App. No.
16/200,412
Granted
Jun 15, 2021
Kind
B2
Abstract

An organic electroluminescence device includes a first electrode and a second electrode which are positioned facing each other, and at least one organic layer between the first electrode and the second electrode, wherein the at least one organic layer includes a monoamine compound which is represented by Formula 1 and includes at least one adamantyl group as a substituent, thereby achieving improved device efficiency:

Claims (85)

1. An organic electroluminescence device, comprising:

a first electrode;

a second electrode on the first electrode; and

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

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

wherein, in Formula 1,

at least one selected from Ar 1 , Ar 2 and Ar 3 is represented by the following Formula 2, and the remaining ones of Ar 1 , Ar 2 and Ar 3 are each independently 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:

in Formula 2,

R 1 to R 3 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 20 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,

“m” is 0 or 1,

“a”, “b”, “x” and “y” are each independently an integer of 0 to 4,

wherein if “m” is 0, “x” is an integer of 1 or more, and if “m” is 1, “x+y” is an integer of 1 or more, and

Ad is represented by the following Formula 3:

in Formula 3,

R 4 is 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 20 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, and

“n” is an integer of 0 to 15.

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

an emission layer; and

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

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

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

an emission layer;

a hole injection layer between the first electrode and the emission layer; and

a hole transport layer between the hole injection layer and the emission layer,

wherein the hole transport layer comprises the monoamine compound represented by Formula 1.

4. The organic electroluminescence device of claim 1 , wherein Formula 3 is represented by the following Formula 3-1 or Formula 3-2:

wherein, in Formula 3-1 and Formula 3-2, R 4 and “n” are the same as defined in Formula 3.

5. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by the following Formula 1-A or Formula 1-B:

wherein, in Formula 1-B,

“m1” and “m2” are each independently 0 or 1, and

“a1”, “a2”, “b1”, “b2”, “x11”, “x12”, “y11”, and “y12” are each independently an integer of 0 to 4,

where if “m1” is 0, “x11” is an integer of 1 or more, if “m1” is 1, “x11+y11” is an integer of 1 or more,

if “m2” is 0, “x12” is an integer of 1 or more, and if “m2” is 1, “x12+y12” is an integer of 1 or more, and

in Formula 1-A and Formula 1-B, Ar 1 and Ar 2 are the same as defined in Formula 1, and R 1 to R 3 , “a”, “b”, “x”, “y”, and Ad are the same as defined in Formula 2.

6. The organic electroluminescence device of claim 5 , wherein Formula 1-A is represented by any one selected from the following Formula 1-1 to Formula 1-3:

wherein, in Formula 1-1 to Formula 1-3, Ar 1 and Ar 2 are the same as defined in Formula 1, and R 1 to R 3 , “a”, “b”, “b”, “x”, “y”, and Ad are the same as defined in Formula 2.

7. The organic electroluminescence device of claim 5 , wherein Ar 1 and Ar 2 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 phenanthryl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

8. The organic electroluminescence device of claim 5 , wherein Ar 1 and Ar 2 are each independently an aryl group having 6 to 30 carbon atoms for forming a ring, the aryl group being an unsubstituted aryl group or an aryl group substituted with at least one selected from a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an arylthio group having 1 to 20 carbon atoms, a triarylsilyl group having 18 to 50 carbon atoms, and an adamantyl group, or

a heteroaryl group having 2 to 30 carbon atoms for forming a ring, the heteroaryl group being an unsubstituted heteroaryl group or a heteroaryl group substituted with at least one selected from a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an arylthio group having 1 to 20 carbon atoms, a triarylsilyl group having 18 to 50 carbon atoms, and an adamantyl group.

9. The organic electroluminescence device of claim 5 , wherein Ar 1 and Ar 2 are each independently represented by any one selected from the following Formula A-1 to Formula A-20:

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

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

wherein, in Formula 1,

at least one selected from Ar 1 , Ar 2 and Ar 3 is represented by the following Formula 2, and the remaining ones of Ar 1 , Ar 2 and Ar 3 are each independently 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:

in Formula 2, R 1 to R 3 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 20 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,

“m” is 0 or 1,

“a”, “b”, “x” and “y” are each independently an integer of 0 to 4,

wherein, if “m” is 0, “x” is an integer of 1 or more, and if “m” is 1, “x+y” is an integer of 1 or more,

Ad is represented by the following Formula 3:

in Formula 3,

R 4 is 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 20 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, and

“n” is an integer of 0 to 15.

12. The monoamine compound of claim 11 , wherein Formula 3 is represented by the following Formula 3-1 or Formula 3-2:

in Formula 3-1 and Formula 3-2, R 4 and “n” are the same as defined in Formula 3.

13. The monoamine compound of claim 11 , wherein Formula 1 is represented by the following Formula 1-A or Formula 1-B:

in Formula 1-B,

“m1” and “m2” are each independently 0 or 1, and

“a1”, “a2”, “b1”, “b2”, “x11”, “x12”, “y11”, and “y12” are each independently an integer of 0 to 4,

wherein, if “m1” is 0, “x11” is an integer of 1 or more, if “m1” is 1, “x11+y11” is an integer of 1 or more,

if “m2” is 0, “x12” is an integer of 1 or more, and if “m2” is 1, “x12+y12” is an integer of 1 or more, and

in Formula 1-A and Formula 1-B, Ar 1 and Ar 2 are the same as defined in Formula 1, and R 1 to R 3 , “a”, “b”, “b”, “x”, “y”, and Ad are the same as defined in Formula 2.

14. The monoamine compound of claim 13 , wherein Formula 1-A is represented by any one selected from the following Formula 1-1 to Formula 1-3:

in Formula 1-1 to Formula 1-3, Ar 1 and Ar 2 are the same as defined in Formula 1, and R 1 to R 3 , “a”, “b”, “x”, “y”, and Ad are the same as defined in Formula 2.

15. The monoamine compound of claim 14 , wherein Formula 1-1 is represented by any one selected from the following Formula 1-1a to Formula 1-1e:

in Formula 1-1a and Formula 1-1b, “a11” is an integer of 0 to 3,

in Formula 1-1c, Formula 1-1d, and Formula 1-1e, “a12” is an integer of 0 to 2, and

in Formula 1-1a to Formula 1-1e, Ar 1 and Ar 2 are the same as defined in Formula 1, and R 1 , R 2 , and Ad are the same as defined in Formula 2.

16. The monoamine compound of claim 14 , wherein Formula 1-2 is represented by any one selected from the following Formula 1-2a to Formula 1-2c:

in Formula 1-2a, “x1” is 1 or 2,

in Formula 1-2b, “y1” is 1 or 2,

in Formula 1-2c, “x2” is 1 or 2,

R 31 and R 32 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 20 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, and

in Formula 1-2a to Formula 1-2c, Ar 1 and Ar 2 are the same as defined in Formula 1, and “a”, “b”, R 1 , R 2 , R 3 , and Ad are the same as defined in Formula 2.

17. The monoamine compound of claim 14 , wherein Formula 1-3 is represented by any one selected from the following Formula 1-3a to Formula 1-3c:

in Formula 1-3a, “x1” is 1 or 2,

in Formula 1-3b, “y1” is 1 or 2,

in Formula 1-3c, “x2” is 1 or 2,

R 31 and R 32 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 20 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, and

in Formula 1-3a to Formula 1-3c, Ar 1 and Ar 2 are the same as defined in Formula 1, and “a”, “b”, R 1 , R 2 , R 3 , and Ad are the same as defined in Formula 2.

18. The monoamine compound of claim 13 , wherein Ar 1 and Ar 2 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 phenanthryl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

19. The monoamine compound of claim 13 , wherein Ar 1 and Ar 2 are each independently an aryl group having 6 to 30 carbon atoms for forming a ring, the aryl group being an unsubstituted aryl group or an aryl group substituted with at least one selected from a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an arylthio group having 1 to 20 carbon atoms, a triarylsilyl group having 18 to 50 carbon atoms, and an adamantyl group, or

a heteroaryl group having 2 to 30 carbon atoms for forming a ring, the heteroaryl group being an unsubstituted heteroaryl group or a heteroaryl group substituted with at least one selected from a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryloxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an arylthio group having 1 to 20 carbon atoms, a triarylsilyl group having 18 to 50 carbon atoms, and an adamantyl group.

20. The monoamine compound of claim 13 , wherein Ar 1 and Ar 2 are each independently represented by any one selected from the following Formula A-1 to Formula A-20:

21. The monoamine compound of claim 11 , wherein R 1 is a hydrogen atom or an unsubstituted phenyl group.

22. The monoamine compound of claim 11 , wherein the monoamine compound represented by Formula 1 is represented by any one selected from compounds in the following Compound Group 1 and Compound Group 2:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2018
From: TAKADA, ICHINORI; IMADA, ICHIRO
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 047584/0967 →
Priority Claims (2)
KR 10-2017-0160887 · Nov 28, 2017 · national
KR 10-2018-0094264 · Aug 13, 2018 · national
Continuity (1)
Related Publication 20190165273A1 · May 30, 2019
Cited By (1)
US 12,606,741