# US 2016/0355684 A1 · Anthraquinone dye used for a color filter of a lcd

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- Number: US 2016/0355684 A1
- Document ID: US20160355684A1
- Status: Published application
- Kind: A1
- Application number: 15/108,792
- Filed: 2014-01-29
- Published: 2016-12-08
- Earliest claimed: 2014-01-29
- Assignees: Dow Global Technologies LLC
- Applicants: Dow Global Technologies LLC
- Inventors: Yang Li; Guihong Liao; Matthew S. Remy; Juelin Liu; Hua Ren; Yanping Sun; Chao He; Yu Cai; William J. Kruper, JR.
- Web page: https://patentgrep.com/patent/US20160355684A1

## CPC

- C09B 69/008: {Dyes containing a substituent, which contains a silicium atom}
- C07C 221/00: Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07F 7/0838: {Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21)}
- C07F 7/0879: {Hydrosilylation reactions}
- C09B 1/325: {Dyes with no other substituents than the amino groups}
- G02F 1/133514: {Colour filters}
- C07C 2603/24: Anthracenes; Hydrogenated anthracenes
- 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)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS

## Abstract

An anthraquinone compound which is suitable for forming a color filter used for a liquid crystal display device, a composition containing a resin and the anthraquinone compound, an article having a polymer layer containing the compound and a resin, a color filter containing the compound and a method for synthesis of an asymmetric anthraquinone compound are developed.

## Claims

### Claim 1

An anthraquinone compound having siloxane structure, represented by the following formula (1) or formula (2):
wherein R1-10 are independently selected from the group consisting of alkyl group having 1 to 20 carbon atoms, halogen atom, hydrogen atom, hydroxyl group, cyano group, sulfonyl group, sulfo group, sulfato group, aryl group, nitro group, carboxyl group, alkoxy group having 1 to 20 carbon atoms and *—X-L-S1; wherein X is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, sulfonyl group, sulfo group and carboxyl group; L is selected from divalent groups consisting of alkylene, oxyalkylene, cycloalkylene, oxygen atom and hetero-containing alkylene; Si is siloxane containing group represented by —(O—Si(R11)(R12)—)n—O—Si(CH3)3, n is an integer from 0 to 100 and R11, R12 are independently selected from the group consisting of hydrogen atom, alkyl group having 1 to 20 carbon atoms and —(O—Si)m—O—Si(CH3)3, m is an integer from 0 to 100; * means the position which bonds to the benzene ring of formula (1); and at least one of R1-10 is *—X-L-S1:
wherein R1-9 are independently selected from the group consisting of alkyl group having 1 to 20 carbon atoms, halogen atom, hydrogen atom, hydroxyl group, cyano group, sulfonyl group, sulfo group, sulfato group, aryl group, nitro group, carboxyl group and alkoxy group having 1 to 20 carbon atoms, X is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, sulfonyl group, sulfo group and carboxyl group, L is selected from divalent groups consisting of alkylene, oxyalkylene, cycloalkylene, oxygen atom and hetero-containing alkylene; S2 is siloxane containing divalent group represented by —Si(R10)(R11)—(O—Si(R12)(R13))n-O—Si(R14)(R15)—, R10-15 are selected from the group consisting of hydrogen atom, alkyl group having 1 to 20 carbon atoms and —(O—Si)m—O—Si(CH3)3, m is an integer from 0 to 100, n is an integer from 0 to 100.

### Claim 2 (depends on 1)

The compound of claim 1, wherein at least two of R1-10 in formula (1) are *—X-L-S1.

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

The compound of claim 1 or 2, wherein X is oxygen atom.

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

The compound of any of claims 1 to 3, wherein L is alkylene group having 1 to 3 carbon atoms.

### Claim 5 (depends on 1, 2, 3, 4)

The compound of any of claims 1 to 4, wherein n is 2 or less and m is 2 or less.

### Claim 6 (depends on 1, 2, 3, 4, 5)

A composition comprising a resin and the compound of any of claims 1 to 5.

### Claim 7 (depends on 6)

The composition of claim 6, further comprises a radiation-sensitive compound.

### Claim 8 (depends on 6, 7)

An article having a polymer layer formed from the composition of claim 6 or 7.

### Claim 9 (depends on 8)

The article of claim 8, wherein the polymer layer is a negative-type layer.

### Claim 10 (depends on 1, 2, 3, 4, 5)

A color filter comprising at least one the compound of any of claims 1 to 5.

### Claim 11

A method for synthesis of an asymmetric 1,4-diaminoanthraquinone compound wherein the amino groups are substituted with different groups selected from alkyl, aryl and alkylaryl groups, comprising the steps of:
(A) reacting in the presence of at least one catalyst a mixture of 2,3-dihydro-9,10-dihydroxy-1,4-anthraquinone and 1,4-dihydroxyanthraquinone with a compound represented by the formula (3),
R1—NH2 (3)
wherein R1 is an aryl group, alkyl group or an arylalkyl group, R1 can be substituted by the group selected from the group consisting of hydroxyl group, amino group, thiol group, alkyl group having 1 to 20 carbon atoms, aryl group or combination thereof to form a first intermediate, and
(B) reacting in the presence of at least one catalyst the first intermediate with a compound represented by the formula (4)
R2—NH2 (4)
wherein R2 is an aryl group, alkyl group or an arylalkyl group, R2 can be substituted by the group selected from the group consisting of hydroxyl group, amino group, thiol group, alkyl group having 1 to 20 carbon atoms, aryl group or combination thereof, and R1 and R2 are different.

### Claim 12 (depends on 11)

The method of claim 11 wherein R1 of the formula (3) is aryl group and R2 of the formula (4) is aryl group, R1 and R2 are substituted by the group selected from the group consisting of hydroxyl group, amino group, thiol group, alkyl group having 1 to 20 carbon atoms, aryl group or combination thereof, and the substituent of R1 and the substituent of R2 are different.

### Claim 13

A method for synthesis of an asymmetric 1,4 bis(arylamine)anthraquinone compound, comprising the steps of:
(A) reacting in the presence of boric acid a mixture of 2,3-dihydro-9,10-dihydroxy-1,4-anthraquinone and 1,4-dihydroxyanthraquinone with a compound represented by the formula (5)
Ar1—NH2 (5)
wherein Ar1 is aryl group substituted by at least one group selected from the group consisting of hydroxyl group, amino group, thiol group, alkyl group having 1 to 20 carbon atoms, aryl group or combination thereof to form a first intermediate, and
(B) reacting in the presence of boric acid, metal zinc and an acid the first intermediate with a compound represented by the formula (6)
Ar2—NH2 (6)
wherein Ar2 is aryl group substituted by at least one group selected from the group consisting of hydroxyl group, amino group, thiol group, alkyl group having 1 to 20 carbon atoms, aryl group or combination thereof, and the substituent of Ar1 and the substituent of Are are different.

### Claim 14 (depends on 13)

The method for claim 13, wherein the mole ratio of 2,3-dihydro-9,10-dihydroxy-1,4-anthraquinone and 1,4-dihydroxyanthraquinone is 9:1 to 1:1.

### Claim 15 (depends on 13, 14)

The method for claim 13 or 14, wherein the acid is pivalic acid.