# US 12,760,028 B2 · Organic compound, organic electroluminescent device and electronic apparatus thereof

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- Number: US 12,760,028 B2
- Document ID: US12760028B2
- Status: Granted
- Kind: B2
- Application number: 18/003,918
- Filed: 2022-03-22
- Published: 2023-09-21
- Granted: 2026-10-13
- Earliest claimed: 2021-04-16
- Assignees: Shaanxi Lighte Optoelectronics Material Co., Ltd.
- Applicants: Shaanxi Lighte Optoelectronics Material Co., Ltd.
- Inventors: Na Yue; Zhengshen Hua; Youngkook Kim; Yingwen Li
- Web page: https://patentgrep.com/patent/US12760028B2

## CPC

- C07D 487/06: Peri-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C09K 11/06: containing organic luminescent materials
- H10K 85/00: Organic materials used in the body or electrodes of devices covered by this subclass
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/624: {containing six or more rings}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- 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}
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present application relates to an organic compound, and there are electron transport and injection groups and a conjugated fused heteroaromatic ring in a structure of the organic compound. The organic compound can be used in a functional layer of an organic light-emitting device (OLED). When used in an OLED, the organic compound of the present application can improve the light-emitting efficiency and service life of the OLED.

## Claims

### Claim 1

An organic compound with a structure shown in formula 1:
wherein R5 and R6 are the same or different, and are each independently selected from the group consisting of alkyl with 1 to 6 carbon atoms, haloalkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 15 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 12 carbon atoms; or R5 and R6 are optionally connected to form a 5- to 18-membered aliphatic ring or a substituted or unsubstituted 5- to 18-membered aromatic ring together with the carbon atom to which they are jointly connected, and a substituent on the 5- to 18-membered aromatic ring is selected from the group consisting of deuterium, halogen, and alkyl with 1 to 6 carbon atoms;
R1, R2, R3, and R4 are the same or different, and are each independently selected from the group consisting of a group shown in formula 2, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, hydrogen, deuterium, halogen, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, and trialkylsilyl with 3 to 12 carbon atoms, and any one or two of R1, R2, R3, and R4 are the group shown in formula 2,
wherein Het is electron-deficient 6- to 18-membered nitrogen-containing heteroarylene;
L1, L2, and L3 are each independently selected from the group consisting of a single bond, substituted or unsubstituted arylene with 6 to 30 carbon atoms, and substituted or unsubstituted heteroarylene with 3 to 30 carbon atoms;
Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted aryl with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms;
n1 and n4 are the same or different, represent a number of R1 and a number of R4 respectively, and are each independently selected from the group consisting of 1, 2, 3, and 4; n3 represents a number of R3 and is selected from the group consisting of 1 and 2; and n2 represents a number of R2 and is selected from the group consisting of 1, 2, and 3;
substituents in L1, L2, L3, Ar1, Ar2, R5, and R6 are the same or different, and are each independently selected from the group consisting of deuterium, cyano, halogen, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms, trialkylsilyl with 1 to 12 carbon atoms, arylsilyl with 6 to 18 carbon atoms, aryloxy with 6 to 20 carbon atoms, and arylthio with 6 to 20 carbon atoms; and
optionally, in Ar1 and Ar2, any two adjacent substituents connected to form a substituted or unsubstituted 5- to 15-membered ring, and a substituent on the 5 to 15-membered ring is independently selected from the group consisting of deuterium, cyano, halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, trialkylsilyl with 3 to 6 carbon atoms, aryl with 6 to 12 carbon atoms, and heteroaryl with 5 to 12 carbon atoms.

### Claim 2 (depends on 1)

The organic compound according to claim 1, wherein R5 and R6 are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, phenyl, naphthyl, biphenyl, fluorenyl, dimethylfluorenyl, anthracenyl, phenanthryl, pyridyl, dibenzothienyl, dibenzofuranyl, and carbazolyl; or R5 and R6 are connected to form a fluorene ring, cyclopentane, cyclohexane, or
together with the carbon atom to which they are jointly connected.

### Claim 3 (depends on 1)

The organic compound according to claim 1, wherein the Het is selected from the group consisting of triazinylene, pyridylene, pyrimidinylene, quinolinylene, quinoxalinylene, quinazolinylene, isoquinolinylene, benzimidazolylene, benzothiazolylene, benzoxazolylene, phenanthrolinylene, benzoquinazolinylene, phenanthroimidazolylene, benzofuranopyrimidinylene, benzothienopyrimidinylene, and the following groups:

### Claim 4 (depends on 1)

The organic compound according to claim 1, wherein L1, L2, and L3 are each independently selected from the group consisting of a single bond, substituted or unsubstituted arylene with 6 to 18 carbon atoms, and substituted or unsubstituted heteroarylene with 5 to 12 carbon atoms; and
optionally, substituents in L1, L2, and L3 are each independently selected from the group consisting of deuterium, cyano, fluorine, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, and pyridyl.

### Claim 5 (depends on 1)

The organic compound according to claim 1, wherein L1, L2, and L3 are each independently selected from the group consisting of a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthracenylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted dibenzofuranylene, and substituted or unsubstituted carbazolylene; and
substituents in L1, L2, and L3 are each independently selected from the group consisting of deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl, phenyl, naphthyl, and pyridyl.

### Claim 6 (depends on 1)

The organic compound according to claim 1, wherein L1, L2, and L3 are each independently selected from the group consisting of a single bond and a substituted or unsubstituted group W; an unsubstituted group W is selected from the group consisting of the following groups:
wherein
represents a chemical bond; when the group W is substituted by one or more substituents, the one or more substituents are each independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl, phenyl, naphthyl, and pyridyl.

### Claim 7 (depends on 1)

The organic compound according to claim 1, wherein L1, L2, and L3 are each independently selected from the group consisting of a single bond and the following groups:

### Claim 8 (depends on 1)

The organic compound according to claim 1, wherein Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted aryl with 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl with 5 to 20 carbon atoms;
optionally, substituents in Ar1 and Ar2 are each independently selected from the group consisting of deuterium, cyano, fluorine, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 15 carbon atoms, and heteroaryl with 5 to 12 carbon atoms; and optionally, in Ar1 and Ar2, any two adjacent substituents connected to form a substituted or unsubstituted 5- to 13-membered ring, and a substituent on the 5- to 13-membered ring is selected from the group consisting of deuterium, cyano, halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, trialkylsilyl with 3 to 6 carbon atoms, aryl with 6 to 12 carbon atoms, and heteroaryl with 5 to 12 carbon atoms.

### Claim 9 (depends on 1)

The organic compound according to claim 1, wherein Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted spirobifluorenyl; and
substituents in Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl, phenyl, naphthyl, dibenzothienyl, dibenzofuranyl, carbazolyl, and pyridyl.

### Claim 10 (depends on 1)

The organic compound according to claim 1, wherein Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of hydrogen, deuterium, and a substituted or unsubstituted group Y; an unsubstituted group Y is selected from the group consisting of the following groups:
wherein
represents a chemical bond; and when the group Y is substituted by one or more substituents, the one or more substituents are each independently selected from the group consisting of deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, and pyridyl.

### Claim 11 (depends on 1)

The organic compound according to claim 1, wherein Ar1 and Ar2 are the same or different, and are each independently selected from the group consisting of hydrogen, deuterium, and the following groups:

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 1)

The organic compound according to claim 1, wherein R5 and R6 are each independently selected from the group consisting of methyl and the following groups:
or R5 and R6 are linked to form one selected from the group consisting of the following spiro-rings together with carbon atoms attached to the two:

### Claim 14 (depends on 1)

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

### Claim 15 (depends on 1)

An organic light-emitting device (OLED), comprising: an anode and a cathode that are arranged oppositely, and a functional layer arranged between the anode and the cathode,
wherein the functional layer comprises the organic compound according to claim 1; and
optionally, the functional layer comprises an electron transport layer (ETL) and/or a light-emitting layer, and the ETL and/or the light-emitting layer comprises the organic compound.

### Claim 16 (depends on 15)

An electronic apparatus comprising the OLED according to claim 15.