IP Library › Granted Patent US 11,038,123
Granted Patent B2
US 11,038,123 · App. 15/934,943 · Granted Jun 15, 2021

Compound and organic electronic device using the same

Inventors: Hui-Ling Wu (Jhubei, TW); Ming-Zer Lee (Jhubei, TW); Shwu-Ju Shieh (Jhubei, TW); Chi-Chung Chen (Jhubei, TW)
Assignee: SHANGHAI NICHEM FINE CHEMICAL CO., LTD.
H01L51/0073H01L51/5012H01L51/5064H01L51/5072H01L51/5092H01L51/5096H01L51/5206H01L51/5221H01L51/56C07D307/91H01L2251/5384
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Quick Facts
Patent No.
US 11,038,123
App. No.
15/934,943
Granted
Jun 15, 2021
Kind
B2
Abstract

Provided are a novel compound and an organic electronic device using the same. The novel compound is represented by the following Formula (I): wherein n1, n2, m1, m2, m3, and g1 are each independently an integral, and the sum of n1 and n2 is 2 or 3; Ant is L 1 , L 2 and L 3 are each independently an arylene group; G 1 and G 2 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and a heteroaryl group; and R 1 and R 2 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, an alkyl group, and an aryl group.

Claims (50)

1. A compound for a host material of an emission layer represented by the following Formula (I′):

wherein *1 is bonded to *a, *2 is bonded to *b, and two *3s are bonded to two *4s, respectively;

wherein n1 is an integer from 1 to 3, n2 is an integer from 0 to 2, and the sum of n1 and n2 is 2 or 3;

m1 and m2 are each independently an integer 0 or 1, m1 and m2 are the same or different; and m3 is 0;

g1 is an integer from 0 to 9;

R 1 and R 2 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, an alkyl group having 1 to 12 carbon atoms, and an aryl group having 6 to 30 ring carbon atoms, and R 1 and R 2 are the same or different;

L 1 , L 2 and L 3 are each independently an arylene group having 6 to 60 ring carbon atoms, and L 1 , L 2 and L 3 are the same or different;

Ant is

G 1 and G 2 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 60 ring carbon atoms, a heterocycloalkyl group having 3 to 60 ring carbon atoms, an aryl group having 6 to 60 ring carbon atoms, and a heteroaryl group having 3 to 60 ring carbon atoms;

wherein the group of

in Formula (I′) is represented by

the group of

is represented by any one of the following formulae:

wherein R 11 to R 13 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, an alkyl group having 1 to 12 carbon atoms, and an aryl group having 6 to 30 ring carbon atoms, and R 11 to R 13 are the same or different: and

the group of

in Formula (I′) is represented by

2. The compound for a host material of an emission layer as claimed in claim 1 , wherein the group of

in Formula (I′) is represented by any one of the following formulae:

wherein R 21 to R 23 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, an alkyl group having 1 to 12 carbon atoms, and an aryl group having 6 to 30 ring carbon atoms, and R 21 to R 23 are the same or different.

3. The compound for a host material of an emission layer as claimed in claim 1 , wherein the heteroaryl group having 3 to 60 ring carbon atoms represented by G 2 is represented by any one of the following formulae:

wherein R 31 to R 33 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, an alkyl group having 1 to 12 carbon atoms, and an aryl group having 6 to 30 ring carbon atoms, and R 31 to R 33 are the same or different.

4. The compound for a host material of an emission layer as claimed in claim 1 , wherein the compound is represented by the following Formula (I′″):

G 1 is selected from the group consisting of: the alkyl group having 1 to 40 carbon atoms, the alkenyl group having 2 to 40 carbon atoms, the alkynyl group having 2 to 40 carbon atoms, and the aryl group having 6 to 60 ring carbon atoms; and

G 2 is selected from the group consisting of: the hydrogen atom, the deuterium atom, the alkyl group having 1 to 40 carbon atoms, the alkenyl group having 2 to 40 carbon atoms, the alkynyl group having 2 to 40 carbon atoms, and the aryl group having 6 to 60 ring carbon atoms.

5. The compound for a host material of an emission layer as claimed in claim 1 , wherein the aryl groups having 6 to 60 ring carbon atoms represented by G 1 and G 2 are each independently selected from the group consisting of: a phenyl group, a biphenylyl group, a terphenylyl group, a quaterphenylyl group, a quinquephenylyl group, a naphthyl group, an acenaphthelenyl group, an anthryl group, a benzanthryl group, an aceanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a picenyl group, a pentacenyl group, a pyrenyl group, a benzopyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluoranthenyl group, a benzofluoranthenyl group, a tetracenyl group, a perylenyl group, a coronyl group, a dibenzanthryl group, a naphthylphenyl group, an indacenyl group, a triphenylenyl group, a benzotriphenylenyl group, and any isomeric group thereof.

6. The compound for a host material of an emission layer as claimed in claim 1 , wherein the aryl groups having 6 to 60 ring carbon atoms represented by G 1 and G 2 are each independently selected from the group consisting of:

wherein m is an integer from 1 to 4, n is an integer from 1 to 3, o is an integer 1 or 2, and p is an integer from 1 to 5;

X 1 to X 4 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a halo group, a cyano group, a nitro group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 3 to 30 ring carbon atoms, and an aryloxy group having 6 to 30 ring carbon atoms.

7. The compound for a host material of an emission layer as claimed in claim 1 , wherein the aryl group having 6 to 60 ring carbon atoms represented by G 1 is selected from the group consisting of:

8. The compound for a host material of an emission layer as claimed in claim 1 , wherein the arylene groups having 6 to 60 ring carbon atoms represented by L 1 , L 2 and L 3 are each independently selected from the group consisting of:

wherein m is an integer from 1 to 4, n is an integer from 1 to 3, and o is an integer 1 or 2;

X 1 to X 4 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a halo group, a cyano group, a nitro group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 3 to 30 ring carbon atoms, and an aryloxy group having 6 to 30 ring carbon atoms.

9. The compound for a host material of an emission layer as claimed in claim 1 , wherein g1 is an integer from 0 to 2.

10. The compound for a host material of an emission layer as claimed in claim 9 , wherein g1 is 1, G 1 is represented by

wherein n′1 and n′2 are each independently an integer from 0 to 3, and the sum of n′1 and n′2 is 2 or 3;

m′1, m′2 and m′3 are each independently an integer 0 or 1, and m′1, m′2 and m′3 are the same or different;

R′ 1 and R′ 2 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, an alkyl group having 1 to 6 carbon atoms, and an aryl group having 6 to 18 ring carbon atoms, and R′ 1 and R′ 2 are the same or different;

L′ 1 , L′ 2 and L′ 3 are each independently an arylene group having 6 to 18 ring carbon atoms, L′ 1 , and L′ 2 and L′ 3 are the same or different;

G′ 2 is selected from the group consisting of: a hydrogen atom, a deuterium atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 30 ring carbon atoms, a heterocycloalkyl group having 3 to 30 ring carbon atoms, an aryl group having 6 to 30 ring carbon atoms, and a heteroaryl group having 3 to 30 ring carbon atoms.

11. The compound for a host material of an emission layer as claimed in claim 1 , wherein the compound is selected from the group consisting of:

12. An organic electronic device, comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises the compound for a host material of an emission layer as claimed in claim 1 .

13. The organic electronic device as claimed in claim 12 , wherein the organic electronic device is an organic light emitting device.

14. The organic electronic device as claimed in claim 13 , wherein the organic light emitting device comprises:

a hole injection layer formed on the first electrode;

a hole transport layer formed on the hole injection layer;

an emission layer formed on the hole transport layer, wherein the emission layer comprises a dopant and a first host material, and the first host material is the compound for a host material of an emission layer as claimed in claim 1 ;

an electron transport layer formed on the emission layer; and

an electron injection layer formed between the electron transport layer and the second electrode.

15. The organic electronic device as claimed in claim 14 , wherein the emission layer further comprises a second host material, the second host material is the compound for a host material of an emission layer as claimed in claim 1 , and the second host material is different from the first host material.

16. The organic electronic device as claimed in claim 13 , wherein the organic electronic device is a blue organic electronic device.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 2, 2023
From: SHANGHAI NICHEM FINE CHEMICAL CO., LTD.
To: NICHEM FINE TECHNOLOGY CO., LTD.
Reel/Frame 064473/0215 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 30, 2019
From: NICHEM FINE TECHNOLOGY CO., LTD.
To: SHANGHAI NICHEM FINE CHEMICAL CO., LTD.
Reel/Frame 049041/0049 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2018
From: WU, HUI-LING; LEE, MING-ZER; SHIEH, SHWU-JU; CHEN, CHI-CHUNG
To: NICHEM FINE TECHNOLOGY CO., LTD.
Reel/Frame 045344/0185 →
Continuity (2)
Provisional Application 62476648 · Mar 24, 2017
Related Publication 20180277772A1 · Sep 27, 2018