Compound and carrier system having the compound

Patent metadata

Field	Value
Publication number	US-9496095-B2
Application number	US-201314372462-A
Country	US
Kind code	B2
Filing date	Feb 27, 2013
Priority date	Mar 7, 2012
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

A novel compound represented by general formula (1), a carrier system including a carrier having the novel compound fixed thereon, and a photoelectric conversion device having the carrier system.

In formula (1), Z is a C1-C50 conjugated group; R1 is a C6-C20 aromatic hydrocarbon group, a C7-C20 aromatic hydrocarbon group substituted by an aliphatic hydrocarbon group, or a C1-C20 aliphatic hydrocarbon group, each substituted by carboxyl, cyano, amino, amide, or nitro, the aliphatic hydrocarbon group being optionally interrupted by —O—, etc.; R2 is hydrogen or an optionally substituted C1-C20 hydrocarbon group; R30, R31, R32, R33, R40, R41, R42, R43, and R44 are each hydrogen or optionally substituted hydrocarbon group, and adjacent two of them may be connected to form a ring; R5 is hydrogen or cyano; and R11 is represented by formula (11-1) or (11-2),

wherein n, ring A, and the like are as defined in the description.

First claim

The invention claimed is:

1. A novel compound represented by general formula (1):

wherein Z represents a conjugated group having 1 to 50 carbon atoms selected from an unsaturated aliphatic hydrocarbon group, an aromatic hydrocarbon group, an aromatic heterocyclic group, and a group composed of one or more of these groups;
R1 represents an aromatic hydrocarbon group having 6 to 20 carbon atoms, an aromatic hydrocarbon group having 7 to 20 carbon atoms and substituted by an aliphatic hydrocarbon group, or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, the aromatic hydrocarbon group having 6 to 20 carbon atoms, the substituted aromatic hydrocarbon group having 7 to 20 carbon. atoms, and the aliphatic hydrocarbon group being substituted by at least one of a carboxyl group, a cyano group, an amino group, an amide group, and a nitro group, the aliphatic hydrocarbon group being optionally interrupted by an interrupting group selected from —O—, —COO—, —OCO—, —NR 24 —, —NR 24 COO —, and —OCONR 24 — at up to 3 positions and, upon the interruption occurring at 2 or 3 positions, the interrupting groups not being adjacent to each other; wherein R 24 an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aromatic hydrocarbon group having 7 to 15 carbon atoms and substituted by an aliphatic hydrocarbon group, or an aliphatic hydrocarbon group having 1 to 10 carbon atoms, the aromatic hydrocarbon group having 6 to 10 carbon atoms, the substituted aromatic hydrocarbon group having 7 to 15 carbon atoms, and the aliphatic hydrocarbon group being optionally substituted with a carboxyl group, a cyano group, an amino group, an amide group, or a nitro group;
R2 represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 20 carbon atoms;
R30, R31, R32, R33, R40, R41, R42, R43, and R44 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group; R30 and R31, R40 and R41, R41 and R42, R42 and R43, or R33 and R44 being optionally connected to each other to form a ring;
R5 represents a hydrogen atom or a cyano group; and
R11 represents a group represented by structural formula (11-1) or(11-2):

wherein n represents an integer of 1 to 4: ring A represents a benzene ring, a naphthalene ring, a cyclohexane ring, a cyclohexene ring, or a cyclohexadiene ring; the hydrogen atoms other than that of the carboxyl group in formulae (11-1) and (11-2) being optionally displaced by a carboxyl group, a cyano group, an amino group, an amide group, a nitro group, an aliphatic hydrocarbon group having 1 to 4 carbon atoms and substituted by at least one group selected from a carboxyl group, a cyano group, an amino group, an amide group and a nitro group, or an unsubstituted aliphatic hydrocarbon group having 1 to 4 carbon atoms.

2. The novel compound according to claim 1 , being represented by general formula (2):

wherein. Z, R1,R11, R2, R30, R31, R32, R40, R41, R42, R3, and R5 are as defined for general formula (1).

3. The novel compound according to claim 2 , wherein the conjugated group as represented by Z is a group composed of 1 to 7 groups linked to one another, the groups being selected from groups represented by formulae (Z-1) through (Z-10):

wherein X represents S, O, NR6or SiR6R7; the hydrogen atoms other than that directly bonded to the nitrogen atom is optionally displaced by a fluorine atom, a chlorine atom, an iodine atom, a cyano group, a nitro group, —OR6, —SR6, —NR6R7, —SiR6R7R8, or an optionally substituted aliphatic hydrocarbon group; R6, R7, and R8 each represent a hydrogen atom or an optionally substituted hydrocarbon group.

4. The noyel compound according to claim 2 , wherein the conjuqated group as represented by Z has at least one group represented by formula (Z-7).

5. The novel compound according to claim 3 , wherein the conjugated group as represented by Z has at least one group represented by formula (Z-7).

6. The novel compound according to claim 1 , wherein the coniugated group as represented by Z is a group composed of 1 to 7 groups linked to one another, the groups being selected from groups represented by formulae (Z-1) through (Z-10):

wherein X represents S, O, NR6, or SiR6R7; the hydrogen atoms other than that directly bonded to the nitrogen atom is optionally displaced by a fluorine atom, a chlorine atom, an iodine atom, a cyano group, a nitro group, —OR6, —SR6, —NR6R7, —SiR6R7R8, or an optionally substituted aliphatic hydrocarbon group; R6, R7, and R8each represent a hydrogen atom or an optionally substituted hydrocarbon group.

7. The novel compound according to claim 6 , wherein the conjugated group as represented by Z has at least one group represented by formula (Z-7).

8. The novel compound according to claim 1 , wherein the conjugated group as represented by Z has at least one group represented by formula (Z-7).

9. A carrier system comprising a carrier and a compound represented. by general formula (1) fixed to the carrier:

wherein Z represents a conjugated group having 1 to 50 carbon atoms selected from an unsaturated aliphatic hydrocarbon group, an aromatic hydrocarbon group, an aromatic heterocyclic group, and a group composed of one or more of these groups;
R1 represents an aromatic hydrocarbon group having 6 to 20 carbon atom, an aromatic hydrocarbon group having 7 to 20 carbon atoms and substituted by an aliphatic hydrocarbon group, or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, the aromatic hydrocarbon group having 6 to 20 carbon atoms, the substituted aromatic hydrocarbon group having 7 to 20 carbon atoms, and the aliphatic hydrocarbon group being substituted by at least cue of a carboxyl group, a cyano group, an amino group, an amide group, and a nitro group, the aliphatic hydrocarbon qroup being optionally interrupted by an interrupting group selected from —O—, —COO—, —OCO—, —NR 24 —, —NR 24 COO—, and —OCONR 24 — at lap to 3 positions and upon the interruption occurring at 2 or 3 positions, the interrupting groups not being adjacent to each other; wherein R 24 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aromatic hydrocarbon group having 7 to 15 carbon atoms and substituted by an aliphatic hydrocarbon group, or an aliphatic hydrocarbon group having 1 to 10 carbon atoms, the aromatic hydrocarbon group having 6 to 10 carbon atoms, the substituted aromatic hydrocarbon group having 7 to 15 carbon atoms, and the aliphatic hydrocarbon group being optionally substituted with a carboxyl group, a cyano group, an amino group, an amide group, or a nitro group;
R2 represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 20 carbon atoms;
R30,R31, R32, R33, R40, R41, R42, R43, and R44 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group; R30 and R31, R40 and R41, R41 and R42, R42 and R43, or R33 and R44 being optionally connected to form a ring;
R5 represents a hydrogen atom or a cyano group; and
R11 represents a group represented

Assignees

• Adeka Corp

Inventors

• Osada Hiroyuki
• Aoyama Yohei

Classifications

• C07D409/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title

• H01G9/2031

  comprising titanium oxide, e.g. TiO2 (H01G9/2036 takes precedence) · CPC title

• Y02E10/542

  Dye sensitized solar cells · CPC title

• H01G9/2059 Primary

  comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution · CPC title