Pyrene derivatives and organic electronic device using pyrene derivatives

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.

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.

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.

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.

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.

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.

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.

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.