# US 12,016,242 B2 · Heterocyclic compound and application thereof

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- Number: US 12,016,242 B2
- Document ID: US12016242B2
- Status: Granted
- Kind: B2
- Application number: 17/191,837
- Filed: 2021-03-04
- Published: 2022-07-14
- Granted: 2024-06-18
- Earliest claimed: 2021-01-05
- Assignees: Wuhan Tianma Micro-Electronics Co., Ltd.; Wuhan Tianma Microelectronics Co., Ltd. Shanghai Branch
- Applicants: Wuhan Tianma Micro-Electronics Co., Ltd.; Wuhan Tianma Microelectronics Co., Ltd. Shanghai Branch
- Inventors: Wei Gao; Wenpeng Dai; Lei Zhang; Quan Ran; Lu Zhai; Lilian Kuang
- Web page: https://patentgrep.com/patent/US12016242B2

## CPC

- C07D 491/048: the oxygen-containing ring being five-membered
- C07D 491/147: the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
- C07D 495/14: Ortho-condensed systems
- C09K 11/06: containing organic luminescent materials
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 59/879: {comprising refractive means, e.g. lenses}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

A heterocyclic compound containing heteroatom substituted fluorene is provided in the present disclosure. The heterocyclic compound includes a structure: Y1 is selected from O or S; X1, X2, X3, X4, X5, X6, X7, and X8 are independently selected from CRa or N; X9, X10, X11, X12, X13, X14, X15, X16, X17, X18, X19, X20, X21, X22, X23, and X24 are independently selected from CR1 or N; Ra is independently selected from hydrogen, deuterium, tritium, halogen, nitrile, cyano, nitro, hydroxyl, carbonyl, ester, carboxyl, imide, amide, C1-C20 alkoxy, C1-C20 alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C3-C20 cycloalkenyl, silyl, boron, phosphine oxide, phosphine, sulfonyl, amine, C6-C30 aryl, C3-C30 heteroaryl, or a ring structure; Y2, and Y3 are independently selected from O, S or NR2; Ar1 and Ar2 are independently selected from aryl or heteroaryl; and R1 and R2 are independently selected from hydrogen, deuterium, C1-C20 alkyl, C6-C30 aryl, or C3-C30 heteroaryl.

## Claims

### Claim 1

A heterocyclic compound, having a structure shown in formula I, comprising:
wherein:
Y1 is selected from 0 or S;
X1, X2, X3, X4, X5, X6, X7, and X8 are independently selected from CRa or N, and at least one of X1, X2, X3, X4, X5, X6, X7, and X8 is N;
X9, X10, X11, X12, X13, X14, X15, X16, X17, X18, X19, X20, X21, X22, X23, and X24 are independently selected from CR1 or N;
when there are a plurality of CRa in X1-X8, Ra are same or different; and Ra is independently selected from hydrogen, deuterium, tritium, halogen, nitrile, cyano, nitro, hydroxyl, carbonyl, ester, carboxyl, imide, amide, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted phosphine oxide, substituted or unsubstituted phosphine, substituted or unsubstituted sulfonyl, substituted or unsubstituted amine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or a ring structure formed by bonding adjacent groups;
Y2, and Y3 are independently selected from O, S or NR2;
Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and
R1 and R2 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

### Claim 2 (depends on 1)

The heterocyclic compound according to claim 1, wherein:
Ar1 and Ar2 are independently selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, fluoranthyl, triphenyl, pyrrolyl, pyranyl, thienyl, pyridyl, pyrimidinyl, triazinyl, benzofuranyl, benzothienyl, dibenzofuranyl, or dibenzothienyl.

### Claim 3 (depends on 2)

The heterocyclic compound according to claim 2, wherein Ar1 and Ar2 are independently selected from any one of following structures:
wherein # denotes a connection location.

### Claim 4 (depends on 1)

The heterocyclic compound according to claim 1, wherein:
Y2 and Y3 are independently selected from O, S, or NR2, wherein R2 is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, fluoranthyl, triphenyl, pyrrolyl, pyranyl, thienyl, pyridyl, pyrimidinyl, triazinyl, benzofuranyl, benzothienyl, dibenzofuranyl, or dibenzothienyl.

### Claim 5 (depends on 1)

The heterocyclic compound according to claim 1, wherein:
in the structure
in the formula I, X9, X10, X11, X12, X13, X14, X15, and X16 are independently selected from CR1 or N, and at least one of X9, X10, X11, X12, X13, X14, X15, and X16 is N; and
R1 is selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

### Claim 6 (depends on 5)

The heterocyclic compound according to claim 5, wherein: the structure of
is selected from any one of following structures:

### Claim 7 (depends on 1)

The heterocyclic compound according to claim 1, wherein:
the structure of
is selected from:

### Claim 8 (depends on 1)

The heterocyclic compound according to claim 1, wherein:
in the structure
in the formula I, X17, X18, X19, X20, X21, X22, X23, and X24 are independently selected from CR1 or N, and at least one of X17, X18, X19, X20, X21, X22, X23, and X24 is N; and
R1 is selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

### Claim 9 (depends on 8)

The heterocyclic compound according to claim 8, wherein:
the structure of
is selected from any one of following structures:

### Claim 10 (depends on 1)

The heterocyclic compound according to claim 1, wherein:
the structure of
is selected from:

### Claim 11 (depends on 1)

The heterocyclic compound according to claim 1, wherein:
any 1 to 6 of X1, X2, X3, X4, X5, X6, X7, and X8 are N.

### Claim 12 (depends on 1)

The heterocyclic compound according to claim 1, wherein:
the structure of
is selected from any one of following structures:

### Claim 13 (depends on 12)

The heterocyclic compound according to claim 12, wherein:
the structure of
is selected from any one of following structures:

### Claim 14 (depends on 1)

The heterocyclic compound according to claim 1, wherein:
the structure of
is selected from any one of following structures:

### Claim 15 (depends on 14)

The heterocyclic compound according to claim 14, wherein:
the structure of
is selected from any one of following structures:

### Claim 16 (depends on 1)

The heterocyclic compound according to claim 1, wherein:
the structure of
is selected from any one of following structures:

### Claim 17 (depends on 16)

The heterocyclic compound according to claim 16, wherein:
the structure of
is selected from any one of following structures:

### Claim 18 (depends on 1)

The heterocyclic compound according to claim 1, wherein:
the structure of
is selected from any one of following structures:

### Claim 19 (depends on 1)

The heterocyclic compound according to claim 1, wherein the heterocyclic compound has any one of following structures:

### Claim 20 (depends on 1)

The heterocyclic compound according to claim 1, wherein the heterocyclic compound has any one of following structures:

### Claim 21 (depends on 1)

The heterocyclic compound according to claim 1, wherein the heterocyclic compound has any one of following structures:

### Claim 22 (depends on 1)

The heterocyclic compound according to claim 1, wherein the heterocyclic compound has any one of following structures:

### Claim 23 (depends on 1)

The heterocyclic compound according to claim 1, wherein the heterocyclic compound has any one of following structures:

### Claim 24 (depends on 1)

The heterocyclic compound according to claim 1, wherein the heterocyclic compound has any one of following structures:

### Claim 25

A display panel, comprising an organic light-emitting device, wherein the organic light-emitting device includes an anode, a cathode, and an organic thin film layer between the anode and the cathode; the cathode is covered with a capping layer (CPL); and the CPL layer contains at least a heterocyclic compound, having a structure shown in formula I, the heterocyclic compound comprising:
wherein:
Y1 is selected from 0 or S;
X1, X2, X3, X4, X5, X6, X7, and X8 are independently selected from CRa or N, and at least one of X1, X2, X3, X4, X5, X6, X7, and X8 is N;
X9, X10, X11, X12, X13, X14, X15, X16, X17, X18, X19, X20, X21, X22, X23, and X24 are independently selected from CR1 or N;
when there are a plurality of CRa in X1-X8, Ra are same or different; and Ra is independently selected from hydrogen, deuterium, tritium, halogen, nitrile, cyano, nitro, hydroxyl, carbonyl, ester, carboxyl, imide, amide, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted phosphine oxide, substituted or unsubstituted phosphine, substituted or unsubstituted sulfonyl, substituted or unsubstituted amine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or a ring structure formed by bonding adjacent groups;
Y2, and Y3 are independently selected from 0, S or NR2;
Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and
R1 and R2 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

### Claim 26

A display panel, comprising an organic light-emitting device, wherein the organic light-emitting device includes an anode, a cathode, and an organic thin film layer between the anode and the cathode; the organic thin film layer includes a hole transport layer and/or an electron transport layer, wherein at least one of the hole transport layer and the electron transport layer contains at least a heterocyclic compound, having a structure shown in formula I, the heterocyclic compound comprising:
wherein:
Y1 is selected from 0 or S;
X1, X2, X3, X4, X5, X6, X7, and X8 are independently selected from CRa or N, and at least one of X1, X2, X3, X4, X5, X6, X7, and X8 is N;
X9, X10, X11, X12, X13, X14, X15, X16, X17, X18, X19, X20, X21, X22, X23, and X24 are independently selected from CR1 or N;
when there are a plurality of CRa in X1-X8, Ra are same or different; and Ra is independently selected from hydrogen, deuterium, tritium, halogen, nitrile, cyano, nitro, hydroxyl, carbonyl, ester, carboxyl, imide, amide, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted phosphine oxide, substituted or unsubstituted phosphine, substituted or unsubstituted sulfonyl, substituted or unsubstituted amine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or a ring structure formed by bonding adjacent groups;
Y2, and Y3 are independently selected from O, S or NR2;
Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and
R1 and R2 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.