# US 10,119,030 B2 · Rhodamine-based coloring composition

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- Number: US 10,119,030 B2
- Document ID: US10119030B2
- Status: Granted
- Kind: B2
- Application number: 15/129,607
- Filed: 2015-03-27
- Published: 2017-05-25
- Granted: 2018-11-06
- Earliest claimed: 2014-03-28
- Assignees: Fujifilm Wako Pure Chemical Corporation
- Applicants: Wako Pure Chemical Industries, Ltd.
- Inventors: Katsufumi Suzuki; Tomoaki Horie; Yukihiko Shida
- Web page: https://patentgrep.com/patent/US10119030B2

## CPC

- C09B 69/103: {containing a diaryl- or triarylmethane dye}
- C07D 311/80: Dibenzopyrans; Hydrogenated dibenzopyrans
- C08F 20/36: containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate}
- C08F 220/1807: {C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate}
- C08F 220/56: Acrylamide; Methacrylamide
- C09B 11/24: Phthaleins containing amino groups {; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes}
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

A coloring composition having higher heat resistance as compared with the conventional coloring composition, including a compound represented by general formula (1), and a polymer having a monomer unit derived from the compound. (wherein R1 to R4 each independently represent a hydrogen atom, an alkyl group; R7 represents a hydrogen atom or a methyl group; R8 and R9 each independently represent a hydrogen atom or an alkyl group; Y represents a nitrogen atom or a group represented by formula (1-1): A1 represents an alkylene group having at least one group selected from —O—, —OCO—, —COO—, —NHCO—, —CONH—, —NHCONH— and an arylene group in the chain; A2 represents —NH— or —O—; An −represents an anion containing an aryl group having an electron-withdrawing substituent; n represents an integer of 0 to 3; R8 and R9 may form a cyclic structure of a 5 to 6 membered ring together with —N—(CH2)n—Y— bonding thereto.)

## Claims

### Claim 1

A compound represented by the following general formula (1):
wherein R1 to R4 each independently represent a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, a sulfoalkyl group having 1 to 6 carbon atoms, a carboxyalkyl group having 2 to 7 carbon atoms, a cyanoalkyl group having 2 to 7 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, a phenyl group having a substituent or not having a substituent, or a benzyl group having a substituent or not having a substituent; R7 represents a hydrogen atom or a methyl group; An −represents an anion containing an aryl group having an electron-withdrawing substituent, a sulfonyl group having an electron-withdrawing substituent, or a halogenated alkyl group; A1 represents an alkylene group having 1 to 6 carbon atoms which has at least one group selected from —OCO—, —COO— and —NHCONH—in the chain; or an alkylene group having 1 to 6 carbon atoms; and
(a) when A1 represents the alkylene group having 1 to 6 carbon atoms which has at least one group selected from —OCO—, —COO— and —NHCONH— in the chain, A2 represents —NH— or —O—; Y represents a nitrogen atom or the group represented by the following formula (1-1):
n represents an integer of 0 to 3; R8 represents a hydrogen atom; and R9 represents a hydrogen atom; and
(b) when A1 represents the alkylene group having 1 to 6 carbon atoms, A2 represents —NH—or —O—; Y represents a nitrogen atom or the group represented by the above formula (1-1); n represents 2; R8 and R9 form the following cyclic structure of a 6 membered ring
together with —N—(CH2)n—Y— bonding thereto.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein the electron-withdrawing substituent in An−is a halogen atom.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein the electron-withdrawing substituent in An−is a fluorine atom.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein the electron-withdrawing substituent in An−is a quaternary boron anion.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein An−is a tetrakis(perfluorophenyl)borate anion.

### Claim 6 (depends on 1)

A coloring composition comprising the compound according to claim 1.

### Claim 7 (depends on 1)

A coloring composition for a color filter comprising the compound according to claim 1.

### Claim 8 (depends on 1)

The compound according to claim 1, wherein the alkylene group having 1 to 6 carbon atoms which has at least one group selected from —OCO—, —COO— and —NHCONH—in the chain in A1 is the groups represented by the following general formulae (21-3′) or (21-4′);
—OCO—(CH2)h4′—COO—(CH2)h4— (21-3′)
wherein h4 and h4′ each independently represent an integer of 1 to 3,
—NHCONH—(CH2)h5′— (21-4′)
wherein h5′ represents an integer of 1 to 6.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein A1 is the group represented by the following general formula (21-3′);
—OCO—(CH2)h4′—COO—(CH2)h4— (21-3′)
wherein h4 and h4′ each independently represent an integer of 1 to 3, A2 is —NH— or —O—; Y is the nitrogen atom or the group represented by the above formula (1-1); n is the integer of 0 to 3; R8 is the hydrogen atom; and R9 is the hydrogen atom.

### Claim 10

A polymer having a monomer unit derived from the compound represented by the following general formula (1):
wherein R1 to R4 each independently represent a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, a sulfoalkyl group having 1 to 6 carbon atoms, a carboxyalkyl group having 2 to 7 carbon atoms, a cyanoalkyl group having 2 to 7 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, a phenyl group having a substituent or not having a substituent, or a benzyl group having a substituent or not having a substituent; R7 represents a hydrogen atom or a methyl group; An−represents an anion containing an aryl group having an electron-withdrawing substituent, a sulfonyl group having an electron-withdrawing substituent, or a halogenated alkyl group; A1 represents an alkylene group having 1 to 6 carbon atoms which has at least one group selected from —OCO—, —COO— and —NHCONH—in the chain; or an alkylene group having 1 to 6 carbon atoms; and
(a) when A1 represents the alkylene group having 1 to 6 carbon atoms which has at least one group selected from —OCO—, —COO— and —NHCONH— in the chain, A2 represents —NH— or —O—; Y represents a nitrogen atom or the group represented by the following formula (1-1):
n represents an integer of 0 to 3: R9 represents a hydrogen atom; and R9 represents a hydrogen atom; and
(b) when A1 represents the alkylene group having 1 to 6 carbon atoms, A2 represents —NH— or —O— ; Y represents a nitrogen atom or the group represented by the above formula (1-1); n represents 2; R8 and R9 form the following cyclic structure of a 6 membered ring
together with —N—(CH2)n—Y— bonding thereto.

### Claim 11 (depends on 10)

The polymer according to claim 10, wherein the electron-withdrawing substituent in An−is a halogen atom.

### Claim 12 (depends on 10)

The polymer according to claim 10, wherein the electron-withdrawing substituent in An−is a fluorine atom.

### Claim 13 (depends on 10)

The polymer according to claim 10, wherein the electron-withdrawing substituent in An−is a quaternary boron anion.

### Claim 14 (depends on 10)

The polymer according to claim 10, wherein An−is a tetrakis(perfluorophenyl)borate anion.

### Claim 15 (depends on 10)

The polymer according to claim 10, wherein the polymer is a copolymer.

### Claim 16 (depends on 15)

The polymer according to claim 15, wherein the copolymer is a copolymer having one to two kinds of monomer units derived from a compound represented by the following general formula (2), the general formula (3), the general formula (4) or the general formula (5), and the monomer unit derived from the compound represented by the above-described general formula (1), as configuration components:
wherein R11 represents a hydrogen atom or a methyl group; R12 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 13 carbon atoms, an alkoxyalkyl group having 2 to 9 carbon atoms, an alkoxyalkoxyalkyl group having 3 to 9 carbon atoms, an aryloxyalkyl group having 7 to 13 carbon atoms, a morpholinoalkyl group having 5 to 7 carbon atoms, a trialkylsilyl group having 3 to 9 carbon atoms, an alicyclic hydrocarbon group having 6 to 12 carbon atoms which has oxygen or no oxygen, a dialkylaminoalkyl group having 3 to 9 carbon atoms, a fluoroalkyl group having 1 to 18 carbon atoms, an N-alkylenephthalimide group having 9 to 14 carbon atoms, a group represented by the following general formula (2-1):
—(R21—O)q—R22 (2-1)
wherein R21 represents an alkylene group having 1 to 3 carbon atoms which has a hydroxy group as a substituent or no substituent; R22 represents a phenyl group having a hydroxy group as a substituent or not having a substituent, or an alkyl group having 1 to 3 carbon atoms; and q represents an integer of 1 to 3,
a group represented by the following general formula (2-2):
wherein R23 to R25 represent an alkyl group having 1 to 3 carbon atoms; R26 represents an alkylene group having 1 to 3 carbon atoms, or
a group represented by the following general formula (2-3):
wherein 1 represents an integer of 1 to 6; and R27 represents a phenylene group or a cyclohexylene group;
wherein R11 is the same as described above; R13 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; R14 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, a dialkylaminoalkyl group having 3 to 9 carbon atoms, or a hydroxyalkyl group having 1 to 6 carbon atoms; R13 and R14 may form a morpholino group together with a nitrogen atom adjacent thereto,
wherein R15 represents a phenyl group or a pyrrolidino group; and R11 is the same as described above,
wherein R17 represents a nitrogen atom or an oxygen atom; j represents 0 when R17 is an oxygen atom, and 1 when R17 is a nitrogen atom; R16 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, an alkylcycloalkyl group having 6 to 10 carbon atoms, a halogenated cycloalkyl group having 6 to 7 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, which has an alkyl group having 1 to 6 carbon atoms as a substituent, or a halogenated aryl group having 6 to 10 carbon atoms.

### Claim 17 (depends on 10)

A coloring composition comprising the polymer according to claim 10.

### Claim 18 (depends on 10)

A coloring composition for a color filter comprising the polymer according to claim 10.

### Claim 19 (depends on 10)

The polymer according to claim 10, wherein the alkylene group having 1 to 6 carbon atoms which has at least one group selected from —OCO—, —COO— and —NHCONH—in the chain in A1 is the groups represented by the following general formulae (21-3′) or (21-4′);
—OCO—(CH2)h4′—COO—(CH2)h4— (21-3′)
wherein h4 and h4′ each independently represent an integer of 1 to 3,
—NHCONH—(CH2)h5′— (21-4′)
wherein h5′ represents an integer of 1 to 6.

### Claim 20 (depends on 10)

The polymer according to claim 10, wherein A1 is the group represented by the following general formula (21-3′);
—OCO—(CH2)h4′—(CH2)h4— (21-3′)
wherein h4 and h4′ each independently represent an integer of 1 to 3, A2 is —NH— or —O—; Y is the nitrogen atom or the group represented by the above formula (1-1); n is the integer of 0 to 3; R8 is the hydrogen atom; and R9 is the hydrogen atom.