# US 8,465,671 B2 · Dichroic dye for color filter, composition comprising the same for color filter and color filter array prepared therefrom

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- Number: US 8,465,671 B2
- Document ID: US8465671B2
- Status: Granted
- Kind: B2
- Application number: 12/312,493
- Filed: 2007-11-23
- Published: 2010-03-18
- Granted: 2013-06-18
- Earliest claimed: 2006-11-24
- Assignees: LG Chem, Ltd.
- Applicants: Yong-Il Cho; Sin-Young Kim
- Inventors: Yong-Il Cho; Sin-Young Kim
- Web page: https://patentgrep.com/patent/US8465671B2

## CPC

- C09B 43/28: by etherification of hydroxyl groups
- G02B 5/201: {in the form of arrays}
- G02B 5/3016: {involving passive liquid crystal elements (optical properties of liquid crystals G02F1/0063; polarising elements associated with active liquid crystal devices G02F1/133528)}
- G02F 1/133516: {Methods for their manufacture, e.g. printing, electro-deposition or photolithography}
- G02F 1/133533: {Colour selective polarisers (G02F1/1347 takes precedence)}
- G02F 1/133711: {by organic films, e.g. polymeric films}
- 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)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- 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

There is provided a novel dichroic dye having liquid crystal properties, dichroic properties and polymerizable reactivity, the dichroic dye being used to form a color filter layer having excellent physical properties such as dichroic ratio, heat resistance, durability, high contrast ratio and polarizing properties, a composition comprising the same for color filter, a color filter array plate (an upper plate) prepared therefrom, and a liquid crystal display comprising the color filter array plate. The dichroic dye has a structure of R1-L1-M-L2-D (wherein, D is a dichroic structure, M is a structure with liquid crystal properties, R1 is a reactive end functional group, and L and L1 are linking structures that link R1, M, and D), and the composition for forming a color filter layer includes the dichroic dye. Also, the color filter array plate, which comprises color filter layer formed of the composition of this invention and the liquid crystal display, which comprise the color filter array plate but does not requires an upper alignment film and/or a polarization plate are provided. The color filter array plate and the liquid crystal display comprising the same have excellent physical properties such as durability, polarizing degree, resolution and contrast ratio.

## Claims

### Claim 1

A dichroic dye of the structure of (reactive end functional group)-L1-M-L2-D, wherein D is a dichroic structure, M is a liquid crystal structure, and L1 and L2 are linking structures which link the reactive end functional group, M, and D,
wherein the dichroic structure D is an azo dye having following formula:
wherein R1-R4 and R7-R12 are substituents selected from the group consisting of hydrogen, C1-C20 straight or branched chain alkyl groups, halogen groups, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1-C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, carboxyl groups, carbamoyl groups, C1-C20 aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20 aliphatic sulfonylamino groups, C6-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups, and imide groups; and R5 and R6 are coupled to form a phenyl group.

### Claim 2 (depends on 1)

The dichroic dye of claim 1, wherein the dichroic structure D has its own liquid crystal properties.

### Claim 3 (depends on 1)

The dichroic dye of claim 1, wherein the liquid crystal structure M is at least one selected from the group consisting of:
wherein, Z represents —COO—, —OCO—, —CH2CH2—, —CH═CH—, —C≡C— or a single bond and R1-R12 are substituents selected from the group consisting of hydrogen, C1-C20 straight or branched chain alkyl groups halogen groups, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1-C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, carboxyl groups, carbamoyl groups, C1-C20 aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20 aliphatic sulfonylamino groups, C6-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups, and imide groups.

### Claim 4 (depends on 1)

The dichroic dye of claim 1, wherein the reactive end functional group is selected from the group consisting of:

### Claim 5 (depends on 1)

The dichroic dye of claim 1, wherein the dichroic dye has a structure of R1-L1-M-L2-D-L3-R2, where an end functional group R2 and a linking structure L3 are further added to the other end of a dichroic dye in which a reactive end functional group R1 and a linking structure L1 are not coupled.

### Claim 6 (depends on 5)

The dichroic dye of claim 5, wherein the end functional group R2 is a reactive functional group selected from the group consisting of
or an unreactive functional group selected from the group consisting of C1-C20 alkyl groups, C1-C20 alkoxy groups, and cyclohexyl groups.

### Claim 7 (depends on 1)

The dichroic dye of claim 1, wherein the linking structures are the same or different, and independently selected from the group consisting of
(wherein, n represents integer from 1 to 12).

### Claim 8 (depends on 5)

The dichroic dye of claim 5, wherein the linking structures are the same or different, and independently selected from the group consisting of
(wherein, n represents integer from 1 to 12).

### Claim 9 (depends on 1)

A composition for forming a color filter layer, comprising 1 to 98.85 parts by weight of the dichroic dye defined in claim 1, and 0.15 to 5 parts by weight of other additives.

### Claim 10 (depends on 9)

The composition of claim 9, further comprising up to 95 parts by weight of a curable liquid crystal compound.

### Claim 11 (depends on 10)

The composition of claim 10, wherein the curable liquid crystal compound comprises ester compounds having acrylate groups.

### Claim 12 (depends on 10)

The composition of claim 10, wherein the curable liquid crystal compound is at least one selected from the group consisting of the following Formulas (a) to (d):
(wherein, linking structures P-P4 curable functional groups are the same or different, and independently selected from the group consisting of
linking structures S-S4 are the same or different, and independently selected from the group consisting of
(wherein, n represents integer ranging from 1 to 12),
a liquid crystal structure M′ is at least one selected from the group consisting of:
wherein, Z represents —COO—, —OCO—, —CH2CH2—, —CH═CH—, —C≡C— or a single bond and R1-R12 are substituents selected from the group consisting of hydrogen, C1-C20 straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl, halogen groups such as fluorine, chlorine, bromine, and iodine, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1-C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, C1-C20 carboxyl groups, carbamoyl groups, C1-C20 aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, N—C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20 aliphatic sulfonylamino groups, C5-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups, and imide groups, and
end functional groups R′ are at least one selected from the group consisting of H, F, Cl, Br, I, CN, SCN, SF5H, NO2, C1-20 straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl, C1-C20 alkoxy groups, and C1-C20 aliphatic groups).

### Claim 13 (depends on 10)

The composition of claim 10, wherein the curable liquid crystal compound is at least one selected from the group consisting of compounds of the following Formulas (1) to (4)

### Claim 14 (depends on 9)

The composition of claim 9, further comprising 1 to 10 parts by weight of a curing agent.

### Claim 15 (depends on 9)

A color filter array plate comprising a color filter layer formed of the composition for forming a color filter layer defined as defined in claim 9.

### Claim 16 (depends on 15)

The color filter array plate of claim 15, wherein the color filter array plate comprising:
a substrate having orientation; and
a color filter layer formed on the substrate and made of the composition.

### Claim 17 (depends on 15)

The color filter array plate of claim 15, wherein the color filter array plate comprising:
a substrate;
an alignment film formed on the substrate; and
a color filter layer formed on the alignment film and made of the composition.

### Claim 18 (depends on 15)

The color filter array plate of claim 15, wherein the color filter layer is coated with a dried film thickness of 0.1-10 μm.

### Claim 19 (depends on 15)

A liquid crystal display comprising the color filter array plate defined in claim 15.

### Claim 20 (depends on 19)

The liquid crystal display of claim 19, wherein the liquid crystal display does not require a polarization plate and/or an alignment film.

### Claim 21 (depends on 15)

The liquid crystal display comprising a upper plate, the color filter array plate defined in claim 15, an electrode, a liquid crystal, a lower alignment film, a lower plate and a lower polarization plate, all of which are formed in sequence as viewed from the top thereof.