# US 7,408,072 B2 · Heteropolycyclic compound and dye

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- Number: US 7,408,072 B2
- Document ID: US7408072B2
- Status: Granted
- Kind: B2
- Application number: 10/588,697
- Filed: 2005-02-10
- Published: 2007-08-09
- Granted: 2008-08-05
- Earliest claimed: 2004-02-13
- Assignees: Kochi University
- Inventors: Katsuhira Yoshida; Yousuke Ooyama
- Web page: https://patentgrep.com/patent/US7408072B2

## CPC

- C09B 11/02: derived from diarylmethanes
- C09B 57/00: Other synthetic dyes of known constitution
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)

## Abstract

The present invention provides heteropolycyclic compounds represented by General Formulae (1) and (2): wherein R1 is a straight- or branched-chain C1-C10 alkyl group or the like; R2 and R3 are the same or different and are each a straight- or branched-chain C1-C10 alkyl group or the like; R4 and R5 are each a hydrogen atom; X is —OH or the like; X′ is a straight- or branched-chain C1-C10 alkyl group or the like; and Z is —O— or the like. The heteropolycyclic compounds of the present invention have appropriate optical absorption wavelengths and fluorescence wavelengths and a high luminescence intensity, and can be advantageously used in various applications as colorants that have excellent performance in terms of heat resistance, light resistance, solubility, dispersibility in resist materials, solid luminescence, etc.

## Claims

### Claim 1

A heteropolycyclic compound represented by formula (1):
wherein R1 is a straight- or branched-chain C1-C10 alkyl group, a substituted or unsubstituted C5-C10 cycloalkyl group or a substituted or unsubstituted phenyl group;
R2 and R3 are the same or different and are each a straight- or branched-chain C1-C10 alkyl group, a substituted or unsubstituted C5-C10 cycloalkyl group or a substituted or unsubstituted phenyl group, or R2 and R3 may be linked to each other to form, together with the nitrogen atom to which they are attached, a heterocyclic ring;
R4 and R5 are each a hydrogen atom;
X is a straight-chain C1-C10 alkyl group, an —OCOR6 group, or an —OR6 group;
R6 is a hydrogen atom, a straight- or branched-chain C1-C6 alkyl group or a substituted or unsubstituted C5-C10 cycloalkyl group; and
Z is —O— or —NR6— wherein R6 is as defined above.

### Claim 2 (depends on 1)

A heteropolycyclic compound according to claim 1, wherein, in formula (1), R1 is a straight- or branched-chain C1-C10 alkyl group or a substituted or unsubstituted phenyl group; R2 and R3 are each independently a straight- or branched-chain C1-C10 alkyl group; and X a straight-chain C1-C10 alkyl group, a hydroxy group or an —OCOR6 group wherein R6 is a hydrogen atom or a straight- or branched-chain C1-C6 alkyl group; and Z is —O— or —NR6— wherein R6 is a hydrogen atom or a straight- or branched-chain C1-C6 alkyl group.

### Claim 3

A heteropolycyclic compound represented by formula (2):
wherein R1 is a straight- or branched-chain C1-C10 alkyl group, a substituted or unsubstituted C5-C10 cycloalkyl group or a substituted or unsubstituted phenyl group;
R2 and R3 are the same or different and are each a straight- or branched-chain C1-C10 alkyl group, a substituted or unsubstituted C5-C10 cycloalkyl group or a substituted or unsubstituted phenyl group, or R2 and R3 may be linked to each other to form, together with the nitrogen atom to which they are attached, a heterocyclic ring;
R4 and R5 are each a hydrogen atom;
X is a straight-chain C1-C10 alkyl group, an —OCOR6 group, or an —OR6 group;
R6 is a hydrogen atom, a straight- or branched-chain C1-C6 alkyl group or a substituted or unsubstituted C5-C10 cycloalkyl group; and
Z is —O— or —NR6— wherein R6 is as defined above.

### Claim 4 (depends on 3)

A heteropolycyclic compound according to claim 3, wherein, in formula (2), R1 is a straight- or branched-chain C1-C10 alkyl group or a substituted or unsubstituted phenyl group; R2 and R3 are each independently a straight- or branched-chain C1-C10 alkyl group; and X a straight-chain C1-C10 alkyl group, a hydroxy group or an —OCOR6 group wherein R6 is a hydrogen atom or a straight- or branched-chain C1-C6 alkyl group; and Z is —O— or —NR6— wherein R6 is a hydrogen atom or a straight- or branched-chain C1-C6 alkyl group.

### Claim 5 (depends on 1)

A colorant comprising a heteropolycyclic compound according to claim 1.

### Claim 6 (depends on 1)

A pigment or dye comprising a heteropolycyclic compound according to claim 1.

### Claim 7 (depends on 2)

A colorant comprising a heteropolycyclic compound according to claim 2.

### Claim 8 (depends on 3)

A colorant comprising a heteropolycyclic compound according to claim 3.

### Claim 9 (depends on 4)

A colorant comprising a heteropolycyclic compound according to claim 4.

### Claim 10 (depends on 2)

A pigment or dye comprising a heteropolycyclic compound according to claim 2.

### Claim 11 (depends on 3)

A pigment or dye comprising a heteropolycyclic compound according to claim 3.

### Claim 12 (depends on 4)

A pigment or dye comprising a heteropolycyclic compound according to claim 4.
