# US 10,483,468 B2 · Compound and organic electronic device using the same

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- Number: US 10,483,468 B2
- Document ID: US10483468B2
- Status: Granted
- Kind: B2
- Application number: 15/829,033
- Filed: 2017-12-01
- Published: 2018-06-07
- Granted: 2019-11-19
- Earliest claimed: 2016-12-07
- Assignees: Shanghai Nichem Fine Chemical Co., Ltd.
- Applicants: Nichem Fine Technology Co., Ltd.
- Inventors: Hui-Ling Wu; Liang-Di Liao; Shwu-Ju Shieh; Chi-Chung Chen
- Web page: https://patentgrep.com/patent/US10483468B2

## CPC

- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- C07D 311/82: Xanthenes
- C07D 335/12: Thioxanthenes
- 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 50/16: Electron transporting layers
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/625: {containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/655: {comprising only sulfur as heteroatom}
- 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 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/1092: containing sulfur as the only heteroatom
- G01R 33/46: NMR spectroscopy
- H10K 50/165: comprising dopants
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G01R: MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES (indicating correct tuning of resonant circuits H03J3/12)

## 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 X1 and X2 are each independently C(R3), the two (R3)s are the same or different, and the two (R3)s are joined together to form a first aryl ring; X3 and X4 are each independently C(Rb), the two (Rb)s are the same or different, the two (Rb)s are joined to form a second aryl ring, and the second aryl ring is a polycyclic aromatic ring.

## Claims

### Claim 1

A compound represented by the following Formula (I):
wherein X1 and X2 are each independently C(Ra), the two (Ra)s are the same or different, and the two (Ra)s are joined together to form a first aryl ring;
wherein X3 and X4 are each independently C(Rb), the two (Rb)s are the same or different, and the two (Rb)s are joined to form a second aryl ring, and the second aryl ring is a polycyclic aromatic ring;
wherein Z1 to Z12 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a halogen group, a cyano group, a nitro group, 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 heterocyeloalkyl group having 3 to 60 ring carbon atoms, an aryl group having 6 to 60 ring carbon atoms, a heteroaryl group having 3 to 60 ring carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 60 ring carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 ring carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 60 ring carbon atoms, a phosphine group having 1 to 40 carbon atoms, and a phosphine oxide group having 1 to 40 carbon atoms.

### Claim 2 (depends on 1)

The compound as claimed in claim 1, wherein the polycyclic aromatic ring is selected from the group consisting of: naphthalene ring, anthracene ring, phenanthrene ring, pyrene ring, 9,9-dimethylfluorene ring, benzophenanthrene ring, benzopyrene ring, fluoranthene ring, triphenylene ring and benzofluoranthene ring.

### Claim 3 (depends on 1)

The compound as claimed in claim 1, wherein the compound is represented by any one of the following Formulae (I-I) to (I-XII):
wherein n1 is a positive integral from 0 to 4, and T is selected from the group consisting of: a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a phenyl group.

### Claim 4 (depends on 1)

The compound as claimed in claim 1, wherein the first aryl ring extended from X1 and X2 is a substituted or unsubstituted 6 to 60-membered carbon ring.

### Claim 5 (depends on 4)

The compound as claimed in claim 4, wherein the substituted or unsubstituted 6 to 60-membered carbon ring is selected from the group consisting of: a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted of unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted pyrene ring, a substituted or unsubstituted benzopyrene ring, a substituted or unsubstituted fluoranthene ring, a substituted or unsubstituted benzofluoranthene ring, and a substituted or unsubstituted fluorene ring.

### Claim 6 (depends on 5)

The compound as claimed in claim 5, wherein the substituted or unsubstituted 6 to 60-membered carbon ring is a substituted or unsubstituted benzene structure.

### Claim 7 (depends on 1)

The compound as claimed in claim 1, wherein at least one of Z1 to Z8 in formula (I) is selected from the group consisting of: an alkyl group having 1 to 40 carbon atoms and substituted with at least one functional group, an alkenyl group having 2 to 40 carbon atoms and substituted with at least one functional group, an alkynyl group having 2 to 40 carbon atoms and substituted with at least one functional group, a cycloalkyl group having 3 to 60 ring carbon atoms and substituted with at least one functional group, a heterocycloalkyl group having 3 to 60 ring carbon atoms and substituted with at least one functional group, an aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group, a heteroaryl group having 3 to 60 ring carbon atoms containing at least one nitrogen atom, an alkoxy group having 1 to 40 carbon atoms and substituted with at least one functional group, an aryloxy group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an alkylsilyl group having 1 to 40 carbon atoms and substituted with at least one functional group, an arylsilyl group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an alkylboron group having 1 to 40 carbon atoms and substituted with at least one functional group, an arylboron group having 6 to 60 ring carbon atoms, a phosphine group having 1 to 40 carbon atoms and substituted with at least one functional group, and a phosphine oxide group having 1 to 40 carbon atoms and substituted with at least one functional group, wherein said functional group is selected from the group consisting of: a cyano group, a nitro group, a trifluoromethyl group, a fluor group, and a chloro group.

### Claim 8 (depends on 1)

The compound as claimed in claim 1, wherein at least one of Z1 to Z8 in Formula (I) is selected from the group consisting of:
wherein R1 to R7 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a halogen 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, 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, a heteroaryl group having 3 to 20 ring carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 30 ring carbon atoms, a phosphine group having 1 to 30 carbon atoms, and a phosphine oxide group having 1 to 30 carbon atoms;
wherein n is a positive integral from 0 to 4, m is a positive integral from 0 to 3, o is a positive integral from 0 to 3, and the total of m and o is not more than 5.

### Claim 9 (depends on 1)

The compound as claimed in claim 1, wherein at least one of Z1, Z2. Z3, Z6, Z7, and Z8 in Formula (I) is selected from the group consisting of:
wherein R1 to R7 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a halogen 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, 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, a heteroaryl group having 3 to 20 ring carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 30 ring carbon atoms, a phosphine group having 1 to 30 carbon atoms, and a phosphine oxide group having 1 to 30 carbon atoms;
wherein n is a positive integral from 0 to 4, m is a positive integral from 0 to 3, o is a positive integral from 0 to 3, and the total of m and o is not more than 5;
wherein Z4 and Z5 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a halogen 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, and an alkynyl group having 2 to 12 carbon atoms.

### Claim 10 (depends on 1)

The compound as claimed in claim 1, wherein at least one of Z2, Z3, Z6, and Z7 in Formula (I) is selected from the group consisting of:

### Claim 11 (depends on 1)

The compound as claimed in claim 1, wherein at least one of Z1, Z2, Z3, Z6, Z7, and Z8 in Formula (I) is a substituted triazine group with two phenyl groups, two pyridine groups, two pyrimidine groups, two pyrazine groups, two pyridazine groups, two phenylpyridine groups, two phenylpyrimidine groups, two phenylpyrazine groups, or two phenylpyridazine groups.

### Claim 12 (depends on 1)

The compound as claimed in claim 1, wherein Z9 to Z12 in Formula (I) are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a halogen 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, and an alkynyl group having 2 to 12 carbon atoms.

### Claim 13 (depends on 1)

The compound as claimed in claim 1, wherein the compound is selected from the group consisting of:

### Claim 14 (depends on 1)

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 as claimed in claim 1.

### Claim 15 (depends on 14)

The organic electronic device as claimed in claim 14, wherein the organic electronic device is an organic light emitting device.

### Claim 16 (depends on 15)

The organic electronic device as claimed in claim 15, 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;
an electron transport layer formed on the emission layer, wherein the organic layer is the electron transport layer; and
an electron injection layer formed between the electron transport layer and the second electrode.

### Claim 17 (depends on 15)

The organic electronic device as claimed in claim 15, 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;
a hole blocking layer formed on the emission layer, wherein the organic layer is the bole blocking layer;
an electron transport layer formed on the hole blocking layer; and
an electron injection layer formed between the electron transport layer and the second electrode.

### Claim 18 (depends on 14)

The organic electronic device as claimed in claim 14, wherein the compound is selected from the group consisting of: