IP Library Granted Patent US 11,725,003
Granted Patent B2
US 11,725,003 · App. 16/848,401 · Granted Aug 15, 2023

Amine derivative and an organic electroluminescent device thereof

Inventors: Qian Zhao (Changchun, CN); Hui Liu (Changchun, CN); Yingxue Wang (Changchun, CN)
Assignee: Changchun Hyperions Technology Co., Ltd
C07D413/12C07D235/18C07D263/57C07D277/66C07D403/12C07D417/12H01L51/006H01L51/0073
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Quick Facts
Patent No.
US 11,725,003
App. No.
16/848,401
Granted
Aug 15, 2023
Kind
B2
Abstract

The present disclosure discloses an amine derivative and an organic electroluminescent device thereof, and relates to a technical field of organic photoelectric materials. The technical problem to be solved by the present disclosure is that the current light extraction material has poor thermal stability and the organic electroluminescent device has short service life. The amine derivative of the present disclosure is a diamine with a bridging group containing a fluorenyl group or a spirofluorenyl group, and the substituent group on N contains at least one benzoxazolyl group, benzothiazolyl group or benzimidazolyl group. The organic electroluminescent device of the present disclosure comprises an anode, an organic layer, a cathode and a light extraction layer, the organic layer is located between the anode and the cathode, and the light extraction layer comprises the amine derivative of Formula I according to the present disclosure.

Claims (28)

1. An amine derivative, wherein the amine derivative is represented by Formula I,

wherein both Ar 1 and Ar 2 are selected from a group as shown in Formula II,

wherein the amine derivative is as shown in Formula I-2,

L 1 is selected from the group consisting of a single bond, a substituted or unsubstituted C6-C18 arylene group, and a substituted or unsubstituted C3-C18 heteroarylene group; a is selected from an integer of 0 to 4, and R 1 is selected from the group consisting of a substituted or unsubstituted C1-C15 alkyl group, and a substituted or unsubstituted C6-C18 aryl group, and when a is greater than 1, each R 1 is the same or different, X is selected from O, S or N (R x ), and R x is selected from the group consisting of a substituted or unsubstituted C1-C15 alkyl group, and a substituted or unsubstituted C6-C18 aryl group;

Ar 3 and Ar 4 are independently selected from the group consisting of a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group;

L is selected from the group consisting of one of the groups as shown below,

R is selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C6-C18 aryl group, and a substituted or unsubstituted C3-C18 heteroaryl group; and

L 11 and L 12 are independently selected from the group consisting of a single bond, a substituted or unsubstituted C6-C18 arylene group, and a substituted or unsubstituted C3-C18 heteroarylene group.

2. The amine derivative according to claim 1 , wherein Formula II is selected from the group consisting of groups as shown below,

wherein, b is selected from an integer of 0 to 4, and R 2 is selected from the group consisting of a substituted or unsubstituted C1-C10 alkyl group, and a substituted or unsubstituted C6-C18 aryl group, when b is greater than 1, each R 2 is the same or different;

c is selected from an integer of 0 to 4, and R 3 is selected from the group consisting of a substituted or unsubstituted C1-C10 alkyl group, and a substituted or unsubstituted C6-C18 aryl group, when c is greater than 1, each R 3 is the same or different.

3. The amine derivative according to claim 1 , wherein Ar 3 and Ar 4 are independently selected from one of the groups as shown below,

wherein, d is selected from an integer of 0 to 5, and R 4 is selected from a substituted or unsubstituted C1-C10 alkyl group, when d is greater than 1, each R 4 is the same or different;

e is selected from an integer of 0 to 4, and R 5 is selected from the group consisting of a substituted or unsubstituted C1-C10 alkyl group, and a substituted or unsubstituted C6-C18 aryl group, when e is greater than 1, each R 5 is the same or different;

f is selected from an integer of 0 to 4, and R 6 is selected from the group consisting of a substituted or unsubstituted C1-C10 alkyl group, and a substituted or unsubstituted C6-C18 aryl group, when f is greater than 1, each R 6 is the same or different;

g is selected from an integer of 0 to 5, and R 7 is selected from the group consisting of a substituted or unsubstituted C1-C10 alkyl group, and a substituted or unsubstituted C6-C18 aryl group, when g is greater than 1, each R 7 is the same or different;

R 0 is selected from the group consisting of a substituted or unsubstituted C1-C10 alkyl group, and a substituted or unsubstituted C6-C18 aryl group; and

L 2 is selected from the group consisting of a single bond, a substituted or unsubstituted C6-C18 arylene group, and a substituted or unsubstituted C3-C18 heteroarylene group.

4. The amine derivative according to claim 3 , wherein Ar 3 and Ar 4 are independently selected from one of the groups as shown below,

wherein, R 4 is selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl, and each R 4 is the same or different;

R 5 is selected from the group consisting of methyl, ethyl, propyl, and butyl, and each R 5 is the same or different; and

R 7 is selected from the group consisting of methyl, ethyl, propyl, butyl, phenyl, tolyl, and ethylphenyl, and each R 7 is the same or different.

5. The amine derivative according to claim 1 , wherein Formula II is selected from one of the groups as shown below,

wherein, R 1 is selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl, and each R 1 is the same or different;

R 2 is selected from the group consisting of methyl, ethyl, propyl, and butyl, and each R 2 is the same or different; and

R 3 is selected from the group consisting of methyl, ethyl, propyl, and butyl.

6. The amine derivative according to claim 1 , wherein the amine derivative is selected from one of the structures as shown below,

7. An organic electroluminescent device, comprising an anode, an organic layer, a cathode and a light extraction layer, the organic layer is located between the anode and the cathode, the organic layer comprises a hole transport layer, a light emitting layer, and an electron transport layer, with the hole transport layer being located between the anode and the light emitting layer, and the electron transport layer being located between the light emitting layer and the cathode, the light extraction layer being located on a side of the cathode away from the anode, and the light extraction layer contains the amine derivative according to claim 1 .

Assignments (1)
CHANGE OF NAME Recorded Nov 19, 2020
From: CHANGCHUN HYPERIONS SCIENTIFIC CO., LTD
To: CHANGCHUN HYPERIONS TECHNOLOGY CO., LTD
Reel/Frame 054483/0585 →
Priority Claims (1)
CN 201910631205.2 · Jul 12, 2019 · national
Continuity (1)
Related Publication 20210009574A1 · Jan 14, 2021