# US 7,745,819 B2 · Pyrene derivatives and organic electronic device using pyrene derivatives

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- Number: US 7,745,819 B2
- Document ID: US7745819B2
- Status: Granted
- Kind: B2
- Application number: 11/474,980
- Filed: 2006-06-27
- Published: 2007-03-29
- Granted: 2010-06-29
- Earliest claimed: 2005-06-30
- Assignees: LG Chem, Ltd.
- Inventors: Dong Hoon Lee; Kong Kyeom Kim; Jae Soon Bae; Dae Woong Lee; Jung Bum Kim
- Web page: https://patentgrep.com/patent/US7745819B2

## CPC

- C09K 11/06: containing organic luminescent materials
- H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}
- H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene}
- H10K 85/141: {comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1092: containing sulfur as the only heteroatom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/14: Carrier transporting layers
- H10K 50/17: Carrier injection layers
- H10K 50/171: {Electron injection layers}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- Y02E 10/549: Organic PV cells
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present invention provides an organic electronic device using the compound of the formula (1) and a pyrene derivative having a new structure.

## Claims

### Claim 1

An organic light-emitting device comprising a first electrode, a second electrode and at least one organic material layer arranged between the first electrode and the second electrode, in which at least one organic material layer comprises a compound represented by the following formula (1):
wherein n is an integer of 1 or 2;
X is CH or N;
Y is NR0 when n=1 and N when n=2 wherein R0 is selected from the group consisting of a substituted or unsubstituted alkyl group and a substituted or unsubstituted aryl group;
R1 to R9 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1 to R9 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 2 (depends on 1)

The organic light-emitting device according to claim 1, wherein the compound of the formula (1) is the compound of the following formula (2):
wherein m and n are each an integer of 1 or 2;
X1 and X2 are each independently CH or N;
Y1 and Y2 are each independently NR0 when n=1 and N when n=2 wherein R0 is selected from the group consisting of a substituted or unsubstituted alkyl group and a substituted or unsubstituted aryl group;
R1 to R4 and R7 to R10 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1 to R4 and R7 to R10 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 3 (depends on 1)

The organic light-emitting device according to claim 1, wherein the compound of the formula (1) is selected from the compounds of the following formulas (3) to (8):
wherein R1 to R10 and A1 to A4 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1 to R10 and A1 to A4 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 4 (depends on 1, 2, 3)

The organic light-emitting device according to any one of claims 1 to 3, wherein the organic material layer comprises an electron-injecting layer and an electron-transporting layer, and the electron-injecting layer and the electron-transporting layer comprise the compound of the formula (1).

### Claim 5 (depends on 1, 2, 3)

The organic light-emitting device according to any one of claims 1 to 3, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer comprises the compound of the formula (1).

### Claim 6 (depends on 1, 2, 3)

The organic light-emitting device according to any one of claims 1 to 3, wherein the organic material layer comprises a hole-injecting layer or hole-transporting layer, and the hole-injecting layer or hole-transporting layer comprises the compound of the formula (1).

### Claim 7 (depends on 1, 2, 3)

The organic light-emitting device according to any one of claims 1 to 3, wherein the organic material layer comprises a layer simultaneously performing electron injection/transportation and light emission, and the layer comprises the compound of the formula (1).

### Claim 8

An organic solar cell comprising a first electrode, a second electrode and at least one organic material layer arranged between the first electrode and the second electrode, in which at least one organic material layer comprises a compound represented by the following formula (1):
wherein n is an integer of 1 or 2;
X is CH or N;
Y is NR0 when n=1 and N when n=2 wherein R0 is selected from the group consisting of a substituted or unsubstituted alkyl group and a substituted or unsubstituted aryl group;
R1 to R9 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1to R9may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 9 (depends on 8)

The organic solar cell according to claim 8, wherein the compound of the formula (1) is the compound of the following formula (2):
wherein m and n are each an integer of 1 or 2;
X1 and X2 are each independently CH or N;
Y1 and Y2 are each independently NR0 when n=1 and N when n=2 wherein R0 is selected from the group consisting of a substituted or unsubstituted alkyl group and a substituted or unsubstituted aryl group;
R1 to R4 and R7 to R10 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1 to R4 and R7 to R10 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 10 (depends on 8)

The organic solar cell according to claim 8, wherein the compound of the formula (1) is selected from the compounds of the following formulas (3) to (8):
wherein R1 to R10 and A1 to A4 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1 to R10 and A1 to A4 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 11

An organic photoconductor comprising a first electrode, a second electrode and at least one organic material layer arranged between the first electrode and the second electrode, in which at least one organic material layer comprises a compound represented by the following formula (1):
wherein n is an integer of 1 or 2;
X is CH or N;
Y is NR0 when n=1 and N when n=2 wherein R0 is selected from the group consisting of a substituted or unsubstituted alkyl group and a substituted or unsubstituted aryl group;
R1 to R9 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1to R9may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 12 (depends on 11)

The organic photoconductor according to claim 11, wherein the compound of the formula (1) is the compound of the following formula (2):
wherein m and n are each an integer of 1 or 2;
X1 and X2 are each independently CH or N;
Y1 and Y2 are each independently NR0 when n=1 and N when n=2 wherein R0 is selected from the group consisting of a substituted or unsubstituted alkyl group and a substituted or unsubstituted aryl group;
R1 to R4 and R7 to R10 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1 to R4 and R7 to R10 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 13 (depends on 11)

The organic photoconductor according to claim 11, wherein the compound of the formula (1) is selected from the compounds of the following formulas (3) to (8):
wherein R1 to R10 and A1 to A4 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1 to R10 and A1 to A4 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 14

A compound represented by the following formula (3):
wherein R1 to R9 and A1 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1 to R9 and A1 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 15

A compound represented by the following formula (4):
wherein R2 to R9, A1 and A2 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R2 to R9, A1 and A2 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 16

A compound represented by the following formula (5):
wherein R1 to R9 and A1 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1 to R9 and A1 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 17

A compound represented by the following formula (6):
wherein R1 to R4, R7 to R10, A1 and A2 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1 to R4, R7 to R10, A1 and A2 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 18

A compound represented by the following formula (7):
wherein R2 to R4, R7 to R9, and A1 to A4 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR), a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R2 to R4, R7 to R9, and A1 to A4 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.

### Claim 19

A compound represented by the following formula (8):
wherein R1 to R4, R7 to R10, and A1 to A4 are the same or different from each other and are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silane group, a substituted or unsubstituted boron group, a substituted or unsubstituted aliphatic cyclic group, an amine group (—NHR, —NRR′), a nitrile group (—CN), a nitro group (—NO2), a halogen group, an amide group (—NHCOR, —CONHR, —CONRR′), an ester group (—COOR); a sulfonyl group (—SO2R), a sulfoxide group (—SOR), a sulfonamide group (—SO2NRR′), a sulfonate group (—SO3R), a trifluoromethyl group (—CF3) and -L-M, and the R1 to R4, R7 to R10, and A1 to A4 may form an aromatic, aliphatic or heterocyclic fused ring, together with the adjacent group;
L is a C1-C60 alkylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); a C6-C60 arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR); or 5- to 7-membered heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an amine group (—NHR, —NRR′), an amide group (—NHCOR, —CONHR, —CONRR′), an ether group (—COR) and an ester group (—COOR);
M is selected from the group consisting of an alcohol group (—OH), a thiol group (—SH), a phosphate group (—PO3H), an amine group (—NHR, —NRR′), a substituted or unsubstituted polyolefin, a substituted or unsubstituted polyvinyl, a substituted or unsubstituted polyacrylate, a substituted or unsubstituted polythiophene, a substituted or unsubstituted polypyrrole, and a substituted or unsubstituted polyaniline; and
R and R′ are the same or different from each other and are each independently a hydrogen atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted 5- to 7-membered heterocyclic group.