# US 11,910,709 B2 · Organic compound, and electronic element and electronic device using same

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- Number: US 11,910,709 B2
- Document ID: US11910709B2
- Status: Granted
- Kind: B2
- Application number: 17/913,193
- Filed: 2021-05-11
- Published: 2023-09-21
- Granted: 2024-02-20
- Earliest claimed: 2020-05-12
- Assignees: Shaanxi Lighte Optoelectronics Material Co., Ltd.
- Applicants: Shaanxi Lighte Optoelectronics Material Co., Ltd.
- Inventors: Kongyan Zhang; Tiantian Ma; Jiamei Cao
- Web page: https://patentgrep.com/patent/US11910709B2

## CPC

- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- C07D 251/24: to three ring carbon atoms
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/10: linked by a carbon chain containing aromatic rings
- C07D 405/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present disclosure belongs to the technical field of organic materials and relates to an organic compound, and an electronic element and electronic device using the same. The organic compound has the structure represented by the following Formula I. The organic compound of the present disclosure can improve the performance of the electronic element.

## Claims

### Claim 1

An organic compound, having a structure represented by the following formula 3-1, formula 3-2 or formula 3-4:
wherein Z is selected from O, S, C(R3R4), and N(R5);
R3 and R4 are the same or different, and are each independently selected from alkyl with 1 to 4 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl with 3 to 12 carbon atoms;
R5 is selected from substituted or unsubstituted aryl with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 20 carbon atoms, and substituents in R5 are each independently selected from deuterium, fluorine, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, and trialkylsilyl with 3 to 7 carbon atoms;
X1, X2 and X3 are the same or different, and are each independently selected from C(H) or N, and at least one of X1, X2 and X3 is N;
R1 and R2 are the same or different, and are each independently selected from deuterium, fluorine, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, trialkylsilyl with 3 to 7 carbon atoms, and a group D; wherein the group D is selected from substituted or unsubstituted aryl with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 20 carbon atoms, and substituents in the group D are each selected from deuterium, fluorine, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, and trialkylsilyl with 3 to 7 carbon atoms; n1 represents the number of R1, and n2 represents the number of R2; R1 and R2 are represented by Ri, and n1 to n2 are represented by ni, i is a variable representing 1 or 2; ni is each independently selected from 0, 1, 2, 3 or 4; and any two nis are the same or different when ni is greater than one; optionally, any two adjacent Ris form a ring;
Ari is selected from the group consisting of the following groups:
wherein, in formula 3-2 and formula 3-4, one hydrogen of Ar1 is replaced by an Ad;
L1, L2 and L3 are the same or different, and are each independently selected from a single bond, substituted or unsubstituted arylene with 6 to 35 carbon atoms, and substituted or unsubstituted heteroarylene with 3 to 30 carbon atoms;
Ar2 is selected from a substituted or unsubstituted group V1, and the unsubstituted group V1 is selected from the group consisting of the following groups:
the substituted group V1 has one or more substituents, wherein the substituents are each independently selected from deuterium, fluorine, alkyl with 1 to 4 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, trialkylsilyl with 3 to 7 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, cyclopentyl, cyclohexyl, pyridyl, and phenyl;
substituents in L1 to L3 are the same or different, and are each independently selected from deuterium, halogen group, a group A, trialkylsilyl with 3 to 12 carbon atoms, triarylsilyl with 18 to 24 carbon atoms, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, alkenyl with 2 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms; the group A is selected from substituted or unsubstituted heteroaryl with 3 to 20 carbon atoms or substituted or unsubstituted aryl with 6 to 20 carbon atoms, and substituents in the group A are selected from deuterium, halogen group, and alkyl with 1 to 4 carbon atoms; optionally, any two adjacent substituents form a ring; and
Ad represents adamantyl, in formula 3-1 and formula 3-2, just only one Ad is present; in formula 3-4, just only two Ads are present.

### Claim 2 (depends on 1)

The organic compound of claim 1, wherein L1 is selected from a single bond, substituted or unsubstituted arylene with 6 to 30 carbon atoms, and substituted or unsubstituted heteroarylene with 5 to 30 carbon atoms; and
L2 and L3 are the same or different, and are each independently selected from a single bond, substituted or unsubstituted arylene with 6 to 25 carbon atoms, or substituted or unsubstituted heteroarylene with 3 to 20 carbon atoms.

### Claim 3 (depends on 1)

The organic compound of claim 1, wherein L1 is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothenylene, and substituted or unsubstituted pyridylene; substituents in the L1 are each independently selected from a group C, deuterium, fluorine, alkyl with 1 to 4 carbon atoms, trialkylsilyl with 3 to 7 carbon atoms, and cycloalkyl with 5 to 10 carbon atoms; the group C is selected from substituted or unsubstituted aryl with 6 to 15 carbon atoms, and substituted or unsubstituted heteroaryl with 5 to 15 carbon atoms, and substituents in the group C are each selected from deuterium, fluorine, and alkyl with 1 to 4 carbon atoms; and
L2 and L3 are the same or different, and are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenyl ene, substituted or unsubstituted fluorenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothenylene, and substituted or unsubstituted pyridylene; substituents in the L2 and L3 are each independently selected from deuterium, fluorine, alkyl with 1 to 4 carbon atoms, trialkylsilyl with 3 to 7 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, and heteroaryl with 5 to 12 carbon atoms.

### Claim 4 (depends on 1)

The organic compound of claim 1, wherein L1 is a single bond, or a substituted or unsubstituted group T1, and the unsubstituted group T1 is selected from the group consisting of the following groups:
wherein the substituted group T1 has one or more substituents, and the substituents in the substituted group T1 are independently selected from deuterium, fluorine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, trialkylsilyl with 3 to 7 carbon atoms, and naphthyl.

### Claim 5 (depends on 1)

The organic compound of claim 1, wherein L2 is selected from a single bond, and a substituted or unsubstituted group T2, and the unsubstituted group T2 is selected from the group consisting of the following groups:
wherein the substituted group T2 has one or more substituents, and the substituents in the substituted group T2 are independently selected from deuterium, fluorine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, trialkylsilyl with 3 to 7 carbon atoms, and phenyl.

### Claim 6 (depends on 1)

The organic compound of claim 1, wherein L3 is a single bond, or a substituted or unsubstituted group T3, and the unsubstituted group T3 is selected from the group consisting of the following groups:
wherein the substituted group T3 has one or more substituents, and the substituents in the substituted group T3 are independently selected from deuterium, fluorine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, and trialkylsilyl with 3 to 7 carbon atoms.

### Claim 7 (depends on 1)

The organic compound of claim 1, -L1-Ar1-Ad is selected from the group consisting of the following structures:

### Claim 8 (depends on 1)

The organic compound of claim 1, wherein in formula 3-1 and formula 3-4,
connected with one Ad is selected from the group consisting of the following groups:

### Claim 9 (depends on 1)

The organic compound of claim 1, wherein the organic compound is selected from the group consisting of the following compounds:

### Claim 10 (depends on 1)

An electronic element, comprising an anode, a cathode which is arranged oppositely to the anode, and a functional layer disposed between the anode and the cathode, wherein the functional layer comprises the organic compound of claim 1.

### Claim 11 (depends on 10)

The electronic element of claim 10, wherein the functional layer comprises an organic light-emitting layer comprising the organic compound.

### Claim 12 (depends on 10)

The electronic element of claim 10, wherein the electronic element is an organic electroluminescent device or photoelectric conversion device.

### Claim 13 (depends on 10)

An electronic device, comprising the electronic element of claim 10.

### Claim 14 (depends on 12)

The electronic element of claim 12, wherein the electronic element is an organic electroluminescent device.

### Claim 15 (depends on 14)

The electronic element of claim 14, wherein the organic electroluminescent device is a green organic electroluminescent device.