# US 2019/0377218 A1 · Liquid crystal device including insulating film, light control window and production method

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- Number: US 2019/0377218 A1
- Document ID: US20190377218A1
- Status: Published application
- Kind: A1
- Application number: 16/432,948
- Filed: 2019-06-06
- Published: 2019-12-12
- Earliest claimed: 2018-06-08
- Assignees: Jnc Corporation
- Applicants: Jnc Corporation
- Inventors: CHIEN CHENG LIU; YI CHENG LAN; YI PIN LEE; REN LUNG CHEN; KUIE HUA HSIEH; CHUN HUNG CHIANG; Hiroaki FUJITA
- Web page: https://patentgrep.com/patent/US20190377218A1

## CPC

- G02F 1/133345: {Insulating layers (G02F1/1335, G02F1/1337, G02F1/135, G02F1/136 take precedence)}
- C09K 19/3001: {Cyclohexane rings}
- C09K 19/3003: {Compounds containing at least two rings in which the different rings are directly linked (covalent bond)}
- C09K 19/3059: {in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds}
- C09K 19/3402: {having oxygen as hetero atom (sugars C09K19/0422)}
- C09K 19/542: {Macromolecular compounds}
- C09K 19/56: Aligning agents
- G02F 1/1334: based on polymer dispersed liquid crystals, e.g. microencapsulated liquid crystals
- G02F 1/1341: Filling or closing of cells
- H01B 3/422: {Linear saturated polyesters derived from dicarboxylic acids and dihydroxy compounds}
- C09K 2019/0448: {the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate}
- C09K 2019/2035: {Ph-COO-Ph}
- C09K 2019/2078: {Ph-COO-Ph-COO-Ph}
- C09K 2019/3009: {Cy-Ph}
- C09K 2019/301: {Cy-Cy-Ph}
- C09K 2019/3016: {Cy-Ph-Ph}
- C09K 2019/3063: {Cy-Ph-C≡C-Ph}
- C09K 2019/3422: {the heterocyclic ring being a six-membered ring}
- C09K 2019/548: {stabilizing the alignment; Polymer stabilized alignment}
- C09K 2323/055: Epoxy
- C09K 2323/057: Ester polymer, e.g. polycarbonate, polyacrylate or polyester
- G02F 1/13347: {working in reverse mode, i.e. clear in the off-state and scattering in the on-state}
- G02F 1/13415: {Drop filling process}
- G02F 2202/023: curable
- 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
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H01B: CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES (selection for magnetic properties H01F1/00; waveguides H01P {; printed circuits H05K})

## Abstract

To prevent arcing discharge of a liquid crystal device. Provided is a liquid crystal device including a liquid crystal layer, a first substrate, a second substrate and an insulating film, wherein the liquid crystal layer is arranged between the first substrate and the second substrate, the first substrate includes electrode 1, the second substrate includes electrode 2, the insulating film is arranged between electrode 1 and electrode 2, and the insulating film is a cured product of a thermosetting polymer composition.

## Claims

### Claim 1

A liquid crystal device, comprising a liquid crystal layer, a first substrate, a second substrate and an insulating film, wherein
the liquid crystal layer is arranged between the first substrate and the second substrate,
the first substrate includes electrode 1,
the second substrate includes electrode 2,
the insulating film is arranged between electrode 1 and electrode 2, and
the insulating film is a cured product of a thermosetting polymer composition.

### Claim 2 (depends on 1)

The liquid crystal device according to claim 1, wherein the insulating film is in contact with electrode 1.

### Claim 3 (depends on 2)

The liquid crystal device according to claim 2, wherein the insulating film is also in contact with electrode 2.

### Claim 4 (depends on 1)

The liquid crystal device according to claim 1, wherein the liquid crystal layer includes a liquid crystal composition and a polymer.

### Claim 5 (depends on 1)

The liquid crystal device according claim 1, wherein
the thermosetting polymer composition is a composition containing polyester amide acid obtained by allowing a mixture of tetracarboxylic dianhydride, diamine and a polyhydroxy compound to react, an epoxy compound, an epoxy curing agent and a solvent, and
an insulating film is obtained by (a) applying a thermosetting polymer composition to a substrate, and (b) heating the resulting material.

### Claim 6 (depends on 5)

The liquid crystal device according to claim 5, wherein
the thermosetting polymer composition satisfies expressions: 0.2≤Z/Y≤8 and 0.2≤(Y+Z)/X≤5, in which X represents a molar concentration of tetracarboxylic dianhydride, Y represents a molar concentration of diamine and Z represents a molar concentration of a polyhydroxy compound, and an epoxy compound is contained in 20 to 400 parts by weight based on 100 parts by weight of polyester amide acid.

### Claim 7 (depends on 5)

The liquid crystal device according to claim 5, wherein a compound having a constitutional unit represented by formula (1) or (2) is a thermosetting polymer composition:
wherein, in formulas (1) and (2), R1 is a residue obtained by eliminating two pieces of —CO—O—CO— from tetracarboxylic dianhydride, and in formula (1), R2 is a residue obtained by eliminating two pieces of —NH2 from diamine, and
in formula (2), R3 is a residue obtained by eliminating two pieces of —OH from a polyhydroxy compound.

### Claim 8 (depends on 7)

The liquid crystal device according to claim 7, wherein the tetracarboxylic dianhydride is one or more kinds of compounds selected from 3,3′,4,4′-diphenyl ether tetracarboxylic dianhydride, 3,3′,4,4′-diphenylsulfone tetracarboxylic dianhydride and 1,2,3,4-butanetetracarboxylic dianhydride.

### Claim 9 (depends on 7)

The liquid crystal device according to claim 7, wherein the diamine is one or more kinds of compounds selected from 3,3′-diaminodiphenyl sulfone and bis(4-(3-aminophenoxy)phenylsulfone.

### Claim 10 (depends on 7)

The liquid crystal device according to claim 7, wherein the polyhydroxy compound is one or more kinds of compounds selected from diethylene glycol, triethylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 2-hydroxybenzyl alcohol, 4-hydroxybenzyl alcohol, 4,4′-isopropylidene bis(2-phenoxyethanol), 2-(4-hydroxyphenyl)ethanol, a (meth)acrylic acid-modified product of ethylene glycol diglycidyl ether, a (meth)acrylic acid-modified product of propylene glycol diglycidyl ether, a (meth)acrylic acid-modified product of tripropylene glycol diglycidyl ether, a (meth)acrylic acid-modified product of glycerol diglycidyl ether, a (meth) acrylic acid-modified product of bisphenol A diglycidyl ether and a (meth) acrylic acid-modified product of propylene oxide-modified bisphenol A diglycidyl ether.

### Claim 11 (depends on 1)

The liquid crystal device according to claim 1, wherein the liquid crystal layer includes compound (3) represented by formula (3), and is positive in dielectric anisotropy:
wherein, in formula (3),
ring A is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl,
Z1 is a single bond, ethylene, carbonyloxy or difluoromethyleneoxy,
R4 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons,
X1 and X2 are independently hydrogen or fluorine,
Y1 is fluorine, chlorine, cyano, alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine, and
a is 1, 2, 3 or 4.

### Claim 12 (depends on 1)

The liquid crystal device according to claim 1, wherein the liquid crystal layer includes compound (4) represented by formula (4), and is negative in dielectric anisotropy:
wherein, in formula (4),
ring B and ring D are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine, naphthalene-2,6-diyl, naphthalene-2,6-diyl in which at least one hydrogen is replaced by fluorine or chlorine, chroman-2,6-diyl, or chroman-2,6-diyl in which at least one hydrogen is replaced by fluorine or chlorine,
ring C is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4,5-trifluoronaphthalene-2,6-diyl or 7,8-difluorochroman-2,6-diyl,
Z2 and Z3 are independently a single bond, ethylene, carbonyloxy or methyleneoxy,
R5 and R6 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons,
b is 1, 2 or 3,
c is 0 or 1, and
a sum of b and c is 3 or less.

### Claim 13 (depends on 1)

The liquid crystal device according to claim 1, wherein the liquid crystal layer includes compound (5) represented by formula (5):
wherein, in formula (5),
ring E and ring F are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene or pyrimidine-2,5-diyl,
Z4 is a single bond, ethylene or carbonyloxy,
R7 and R8 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine or chlorine, and
d is 1, 2 or 3.

### Claim 14 (depends on 1)

The liquid crystal device according to claim 1, wherein the liquid crystal layer includes
a liquid crystal composition, and
a polymer obtained by polymerizing a composition containing compound (6) represented by formula (6):
P1-Z5-P2 (6)
wherein, in formula (6),
Z5 is alkylene having 1 to 80 carbons, and in the alkylene, at least one hydrogen may be replaced by alkyl having 1 to 5 carbons, fluorine, chlorine or P3, and at least one piece of —CH2— may be replaced by —O—, —CO—, —COO—, —OCO—, —NH—, —N(R9)—, —CH═CH—, —C≡C— or a divalent group having 5 to 35 carbons obtained by eliminating hydrogen from monocyclic hydrocarbon, fused polycyclic hydrocarbon, a heteromonocyclic compound or a fused heterocyclic compound, and in the divalent group, at least one hydrogen may be replaced by R9 or P3,
R9 is alkyl having 1 to 12 carbons, and in the alkyl, at least one piece of —CH2— may be replaced by —O—, —CO—, —COO— or —OCO—, and in the alkyl, at least one piece of —CH2— may be replaced by —O—, —CO—, —COO— or —OCO—,
P1, P2 and P3 are independently a polymerizable group, hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy, cyano, alkyl having 1 to 20 carbons or alkenyl having 2 to 20 carbons, and in the alkyl and the alkenyl, at least one hydrogen may be replaced by fluorine or chlorine, and at least one piece of —CH2— maybe replaced by —O—, —CO—, —COO— or —OCO—, and at least one hydrogen may be replaced by alkyl having 1 to 12 carbons, and in the alkyl, at least one piece of —CH2— may be replaced by —O—, —CO—, —COO— or —OCO—, and at least one of P1 and P2 is a polymerizable group.

### Claim 15 (depends on 14)

The liquid crystal device according to claim 14, wherein P1, P2 and P3 are independently any one of formula (P-1) to formula (P-6):
wherein, in formula (P-1) to formula (P-6), M1, M2 and M3 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine.

### Claim 16 (depends on 1)

The liquid crystal device according to claim 1, wherein the thermosetting polymer composition contains a photopolymerization initiator.

### Claim 17 (depends on 1)

The liquid crystal device according to claim 1, wherein the liquid crystal layer includes a liquid crystal light control layer, and is cloudy during no current flow.

### Claim 18 (depends on 1)

The liquid crystal device according to claim 1, wherein the liquid crystal layer includes a liquid crystal light control layer, and is cloudy during current flow.

### Claim 19 (depends on 1)

The liquid crystal device according to claim 1, wherein the first substrate is a glass plate, an acrylic plate or a plastic film, and the second substrate is a glass plate, an acrylic plate or a plastic film.

### Claim 20 (depends on 1)

A light control window, comprising the liquid crystal device according to claim 1.

### Claim 21 (depends on 1)

A liquid crystal display apparatus, comprising the liquid crystal device according to claim 1, and a light source apparatus.

### Claim 22

A method for producing a light crystal device, comprising: curing a thermosetting polymer composition on a first substrate; inserting a mixture of a liquid crystal composition and a polymerizable compound between the first substrate and a second substrate; and performing UV exposure to the mixture.

### Claim 23 (depends on 22)

The method for producing the light crystal device according to claim 22, wherein an insulating film is obtained by curing.

### Claim 24 (depends on 23)

The method for producing the light crystal device according to claim 23, wherein curing is made by curing of the thermosetting polymer composition.

### Claim 25 (depends on 24)

The method for producing the light crystal device according to claim 24, wherein curing is made by thermosetting.

### Claim 26 (depends on 22)

The method for producing the light crystal device according to claim 22, wherein inserting is made in a state in which an electrode on the first substrate and an electrode on the second substrate are arranged facing with each other.

### Claim 27

A method for producing a liquid crystal device, comprising:
placing a mixture containing a liquid crystal composition and a polymerizable compound on an electrode on a first substrate;
adhering between an adhesive space and a second substrate; and
bonding between the first substrate and the second substrate through the mixture and the adhesive spacer.

### Claim 28 (depends on 27)

The method for producing the liquid crystal device according to claim 27, wherein placing is made by dropwise addition.