# US 11,444,252 B2 · Nitrogen-containing compound, organic electroluminescent device and electronic apparatus

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- Number: US 11,444,252 B2
- Document ID: US11444252B2
- Status: Granted
- Kind: B2
- Application number: 17/596,885
- Filed: 2020-07-24
- Published: 2022-07-07
- Granted: 2022-09-13
- Earliest claimed: 2019-12-30
- Assignees: Shaanxi Lighte Optoelectronics Material Co., Ltd.
- Applicants: Shaanxi Lighte Optoelectronics Material Co., Ltd.
- Inventors: Linnan Ma; Tiantian Ma; Peng Nan
- Web page: https://patentgrep.com/patent/US11444252B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C07D 401/14: containing three or more hetero rings
- C07D 403/14: containing three or more hetero rings
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/14: containing three or more hetero rings
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/14: containing three or more hetero rings
- C09K 11/06: containing organic luminescent materials
- 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 85/6574: {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
- H10K 85/342: {comprising iridium}
- H10K 2101/10: Triplet emission
- H10K 2101/90: {Multiple hosts in the emissive layer}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present disclosure relates to the technical field of organic materials, and provided therein is a nitrogen-containing compound, comprising at least three directly or indirectly linked fused ring systems. A first fused ring system is a fluorenyl group spiro-linked by adamantane, and adamantyl can greatly increase the electron cloud density of a conjugated structure of the first fused ring system by means of a hyperconjugation effect, which can increase hole mobility. The three fused ring systems enable the nitrogen-containing compound of the present disclosure to have a high first triplet energy level so that the nitrogen-containing compound of the present disclosure is suitable as the host material of an organic light-emitting layer in an organic electroluminescent device. Further provided in the present disclosure are an organic electroluminescent device comprising the described nitrogen-containing compound and an electronic apparatus, and the described nitrogen-containing compound can improve the performance of the organic electroluminescent device.

## Claims

### Claim 1

A nitrogen-containing compound, wherein the structural formula of the nitrogen-containing compound is as shown in formula 1:
wherein ring A is benzene ring;
X is selected from C (Z1Z2), N(Z3), O or S;
Z1 and Z2 are the same or different, and are each independently selected from: methyl, or substituted or unsubstituted aryl with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, or alternatively, Z1 and Z2 are connected with each other to form saturated or unsaturated 5- to -13-membered rings together with the atoms to which they are jointly connected;
Z3 is selected from substituted or unsubstituted aryl with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms;
the substituents of the Z1, Z2 and Z3 are the same or different from each other, and are each independently selected from: deuterium, fluorine, chlorine, bromine, cyano, methyl, aryl with 6 to 20 carbon atoms, or heteroaryl with 6 to 18 carbon atoms;
Y, R1, R2 and R3 are the same or different, and are each independently selected from: deuterium, fluorine, chlorine, bromine, or cyano;
n and n3 are the same or different, and are each independently selected from 0, 1, 2, 3 or 4; n1 and n2 are the same or different, and are each independently selected from 0, 1, 2 or 3;
when n is 2, 3 or 4, any two Y are the same or different; when n1 is 2 or 3, any two R1 are the same or different; when n2 is 2 or 3, any two R2 are the same or different; when n3 is 2, 3 or 4, any two R3 are the same or different;
L is selected from: single bond or unsubstituted T1 or substituted T1, wherein unsubstituted T1 is selected from the group consisting of the following substituents:
substituted T1 is a group formed by substituting the unsubstituted T1 by one or more substituent(s) selected from deuterium, fluorine, chlorine, cyano and methyl and when a plurality of substituents are included on the substituted T1 any two substituents are the same or different.

### Claim 2 (depends on 1)

The nitrogen-containing compound according to claim 1, wherein L is selected from: single bond or unsubstituted T2 or substituted T2, wherein the unsubstituted T2 is selected from the group consisting of the following substituents:
substituted T2 is a group formed by substituting the unsubstituted T2 by one or more substituent(s) selected from deuterium, fluorine, chlorine, cyano and methyl, and when a plurality of substituents are included on the substituted T2, any two substituents are the same or different.

### Claim 3 (depends on 1)

The nitrogen-containing compound according to claim 1, wherein Z1 and Z2 are each independently selected from methyl and phenyl, or alternatively, Z1 and Z2 are connected with each other to form 5- to 10-membered cycloalkyl together with the atoms to which they are jointly connected; and Z3 is selected from substituted or unsubstituted T3;
wherein unsubstituted T3 is selected from the group consisting of the following substituents:
substituted T3 is a group formed by substituting the unsubstituted T3 by one or more substituent(s) selected from deuterium, fluorine, chlorine, cyano, methyl, aryl with 6 to 13 carbon atoms and heteroaryl with 12 carbon atoms, and when a plurality of substituents are included on the substituted T3, any two substituents are the same or different.

### Claim 4 (depends on 1)

The nitrogen-containing compound according to claim 1, wherein the Z3 is independently selected from substituted or unsubstituted T6, wherein unsubstituted T6 is independently selected from the groups as shown below:
substituted T6 is a group formed by substituting the unsubstituted T6 by one or more substituent(s) selected from deuterium, fluorine, chlorine, cyano, methyl, aryl with 6 to 13 carbon atoms and heteroaryl with 12 carbon atoms, and when a plurality of substituents are included on the substituted T6, any two substituents are the same or different.

### Claim 5 (depends on 1)

The nitrogen-containing compound according to claim 1, wherein Z1 and Z2 are each independently selected from methyl and phenyl, or alternatively, Z1 and Z2 are connected with each other to form cyclopentyl, cyclohexyl or adamantyl together with the atoms to which they are jointly connected; and Z3 is selected from substituted or unsubstituted T4;
wherein unsubstituted T4 is selected from the group consisting of the following substituents:
substituted T4 is a group formed by substituting the unsubstituted T4 by one or more substituent(s) selected from deuterium, fluorine, chlorine, cyano, methyl, phenyl, naphthyl, dibenzothiophenyl and dibenzofuranyl, and when a plurality of substituents are included on the substituted T4, any two substituents are the same or different.

### Claim 6 (depends on 1)

The nitrogen-containing compound according to claim 1, wherein the Z3 is independently selected from substituted or unsubstituted T7, wherein unsubstituted T7 is independently selected from the groups as shown below:
substituted T7 is a group formed by substituting the unsubstituted T7 by one or more substituent(s) selected from deuterium, fluorine, chlorine, cyano, methyl, phenyl, naphthyl, dibenzothiophenyl and dibenzofuranyl, and when a plurality of substituents are included on the substituted T7, any two substituents are the same or different.

### Claim 7 (depends on 1)

The nitrogen-containing compound according to claim 1, wherein
is selected from

### Claim 8 (depends on 1)

The nitrogen-containing compound according to claim 1, which has the structure as shown in any one of formula 2-4 to formula 2-19 below:

### Claim 9 (depends on 1)

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

### Claim 10 (depends on 1)

An organic electroluminescent device, comprising an anode, a cathode arranged opposite the anode, and a functional layer arranged between the anode and the cathode;
wherein the functional layer contains the nitrogen-containing compound according to claim 1.

### Claim 11 (depends on 10)

The organic electroluminescent device according to claim 10, wherein a host material of an organic light emitting layer in the functional layer comprises the nitrogen-containing compound.

### Claim 12 (depends on 10)

An electronic apparatus, comprising the organic electroluminescent device according to claim 10.

### Claim 13 (depends on 11)

An electronic apparatus, comprising the organic electroluminescent device according to claim 11.