# US 10,312,459 B2 · Compound and organic electronic device using the same

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- Number: US 10,312,459 B2
- Document ID: US10312459B2
- Status: Granted
- Kind: B2
- Application number: 15/412,834
- Filed: 2017-01-23
- Published: 2017-07-27
- Granted: 2019-06-04
- Earliest claimed: 2016-01-27
- Assignees: Nichem Fine Technology Co., Ltd.
- Applicants: Nichem Fine Technology Co., Ltd.
- Inventors: Liang-Di Liao; Hui-Ling Wu; Shwu-Ju Shieh; Chi-Chung Chen
- Web page: https://patentgrep.com/patent/US10312459B2

## CPC

- C07F 15/0033: {Iridium compounds}
- C07C 211/61: with at least one of the condensed ring systems formed by three or more rings
- C07C 255/51: containing at least two cyano groups bound to the carbon skeleton
- C07D 213/06: containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D 213/22: containing two or more pyridine rings directly linked together, e.g. bipyridyl
- C07D 213/38: having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- C07D 213/57: Nitriles
- C07D 223/14: condensed with carbocyclic rings or ring systems
- C07D 235/18: with aryl radicals directly attached in position 2
- C07D 239/26: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 239/74: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
- C07D 251/24: to three ring carbon atoms
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 313/06: condensed with carbocyclic rings or ring systems
- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/342: {comprising iridium}
- H10K 85/624: {containing six or more rings}
- H10K 85/625: {containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene}
- 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}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07C 2603/18: Fluorenes; Hydrogenated fluorenes
- C07C 2603/98: containing at least one ring with more than six ring members
- C07C 2603/99: containing eight-membered rings
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1033: with oxygen
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/171: {Electron injection layers}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 2101/10: Triplet emission
- Y02E 10/549: Organic PV cells
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Provided are a novel compound and an organic electronic device using the same. The novel compound is represented by the following Formula (I):

## Claims

### Claim 1

A compound represented by the following Formula (I):
wherein one of G1 to G4 is selected from the group consisting of: an heteroaryl group having 3 to 60 carbon atoms and containing at least one nitrogen atom, an aryl group having 6 to 60 carbon atoms and substituted with at least one functional group, and an arylboron group having 6 to 60 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 fluoro group, and a chloro group;
the others of G1 to G4 and G5 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a halogen group, a substituted or nonsubstituted aryl group having 6 to 60 carbon atoms, a substituted or nonsubstituted heteroaryl group having 3 to 60 carbon atoms, and a substituted or nonsubstituted arylboron group having 6 to 60 carbon atoms;
wherein h, i, j, k, l are each independently an integral of 1 to 4.

### Claim 2 (depends on 1)

The compound as claimed in claim 1, wherein h, i, j, k, l are each independently an integral of 1 to 2, and the total of h, i, j, k, and l is not more than 6.

### Claim 3 (depends on 1)

The compound as claimed in claim 1, wherein the compound is represented by the following Formulae (I-I) to (I-XV):
wherein j, k, l are each independently an integral of 1 to 3.

### Claim 4 (depends on 1)

The compound as claimed in claim 1, wherein the heteroaryl group having 3 to 60 carbon atoms and containing the at least one nitrogen atom 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, a trifluoromethyl 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 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 30 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 an integral from 1 to 4, and m is an integral from 1 to 3.

### Claim 5 (depends on 1)

The compound as claimed in claim 1, wherein the heteroaryl group having 3 to 60 carbon atoms and containing the at least one nitrogen atom is selected from the group consisting of:
wherein R1 and R2 are each selected from the group consisting of: a phenyl group, a napthyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a cyano group, a nitro group, a trifluoromethyl group, a fluoro group, a biphenyl group, a phenylnapthyl group, a phenylpyridine group, a phenylpyrimidine group, a phenylpyrazine group, a phenylpyridazine group, a cyanophenyl group, a nitrophenyl group, and a trifluoromethylphenyl group.

### Claim 6 (depends on 5)

The compound as claimed in claim 5, wherein R1 and R2 are each selected from the group consisting of: the pyridine group, the pyrimidine group, the pyrazine group, the pyridazine group, the cyano group, the nitro group, the trifluoromethyl group, the fluoro group, the phenylpyridine group, the phenylpyrimidine group, the phenylpyrazine group, the phenylpyridazine group, the cyanophenyl group, the nitrophenyl group, and the trifluoromethylphenyl group.

### Claim 7 (depends on 1)

The compound as claimed in claim 1, wherein the heteroaryl group having 3 to 60 carbon atoms and containing the at least one nitrogen atom is selected from the group consisting of:

### Claim 8 (depends on 1)

The compound as claimed in claim 1, wherein the aryl group having 6 to 60 carbon atoms and substituted with the at least one functional group is selected from the group consisting of:
wherein R1 is selected from the group consisting of: a hydrogen atom, a deuterium atom, a halogen group, a cyano group, a nitro group, a trifluoromethyl 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 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 30 carbon atoms, a phosphine group having 1 to 30 carbon atoms, and a phosphine oxide group having 1 to 30 carbon atoms;
wherein o is an integral from 0 to 4, p is an integral from 1 to 5, and the total of o and p is not more than 5.

### Claim 9 (depends on 1)

The compound as claimed in claim 1, wherein G3 to G5 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, and a halogen group.

### Claim 10 (depends on 1)

The compound as claimed in claim 1, wherein G1 and G2 are the same.

### Claim 11 (depends on 1)

The compound as claimed in claim 1, wherein G3 and G4 are the same.

### Claim 12 (depends on 1)

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

### Claim 13 (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 14 (depends on 13)

The organic electronic device as claimed in claim 13, wherein the organic electronic device is an organic light emitting device.

### Claim 15 (depends on 14)

The organic electronic device as claimed in claim 14, 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;
an electron injection layer formed between the electron transport layer and the second electrode.

### Claim 16 (depends on 14)

The organic electronic device as claimed in claim 14, 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 hole blocking layer;
an electron transport layer formed on the hole blocking layer;
an electron injection layer formed between the electron transport layer and the second electrode.

### Claim 17 (depends on 3, 13)

The organic electronic device as claimed in claim 13, wherein the organic layer comprises the compound as claimed in claim 3.

### Claim 18 (depends on 4, 13)

The organic electronic device as claimed in claim 13, wherein the organic layer comprises the compound as claimed in claim 4.

### Claim 19 (depends on 5, 13)

The organic electronic device as claimed in claim 13, wherein the organic layer comprises the compound as claimed in claim 5.

### Claim 20 (depends on 13)

The organic electronic device as claimed in claim 13, wherein the compound is selected from the group consisting of: