# US 11,079,634 B2 · Liquid crystal display device and method for manufacturing same

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- Number: US 11,079,634 B2
- Document ID: US11079634B2
- Status: Granted
- Kind: B2
- Application number: 16/079,050
- Filed: 2017-02-17
- Published: 2019-02-28
- Granted: 2021-08-03
- Earliest claimed: 2016-02-24
- Assignees: Sharp Kabushiki Kaisha
- Applicants: Sharp Kabushiki Kaisha
- Inventors: Masanobu Mizusaki; Hiroshi Tsuchiya
- Web page: https://patentgrep.com/patent/US11079634B2

## CPC

- G02F 1/133788: {by light irradiation, e.g. linearly polarised light photo-polymerisation}
- C08J 5/18: Manufacture of films or sheets
- G02F 1/133711: {by organic films, e.g. polymeric films}
- G02F 1/133723: {Polyimide, polyamide-imide}
- C09K 2323/023: Organic silicon compound, e.g. organosilicon
- C09K 2323/027: Polyimide
- G02F 1/133715: {by first depositing a monomer}
- 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
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present invention provides a liquid crystal display device that can sufficiently prevent crystallization of a liquid crystal material at low temperatures, and thereby has high response performance suitable for applications such as HMDs. The liquid crystal display device includes: paired substrates; a liquid crystal layer held between the substrates; and a photo-alignment film disposed on a surface facing the liquid crystal layer of at least one of the substrates, the liquid crystal layer containing a liquid crystal material that has a nematic-isotropic phase transition temperature of 75° C. or lower and a nematic phase temperature range narrower than 100° C., the photo-alignment film containing a polymer, the polymer and/or another component of the photo-alignment film containing a hydrophobic group.

## Claims

### Claim 1

A liquid crystal display device comprising:
paired substrates;
a liquid crystal layer held between the substrates; and
a photo-alignment film disposed on a surface facing the liquid crystal layer of at least one of the substrates,
the liquid crystal layer containing a liquid crystal material that has a nematic-isotropic phase transition temperature of 75° C. or lower and a nematic phase temperature range narrower than 100° C.,
the photo-alignment film containing a first polymer and a first compound each containing a hydrophobic group,
wherein the first polymer includes a polyamic acid represented by the following formula (20):
and the first compound is represented by the following formula (21):

### Claim 2

A liquid crystal display device comprising:
paired substrates;
a liquid crystal layer held between the substrates; and
a photo-alignment film disposed on a surface facing the liquid crystal layer of at least one of the substrates,
the liquid crystal layer containing a liquid crystal material that has a nematic-isotropic phase transition temperature of 75° C. or lower and a nematic phase temperature range narrower than 100° C.,
the photo-alignment film containing a first polymer and a first compound each containing a hydrophobic group,
wherein the first polymer includes a polyamic acid represented by the following formula (20):
and the first compound is represented by the following formula (22):

### Claim 3

A liquid crystal display device comprising:
paired substrates;
a liquid crystal layer held between the substrates; and
a photo-alignment film disposed on a surface facing the liquid crystal layer of at least one of the substrates,
the liquid crystal layer containing a liquid crystal material that has a nematic-isotropic phase transition temperature of 75° C. or lower and a nematic phase temperature range narrower than 100° C.,
the photo-alignment film containing a copolymer of a first monomer unit containing a photo-functional group and a second monomer unit containing a hydrophobic group, wherein the copolymer is represented by the following formula (19):

### Claim 4 (depends on 3)

The liquid crystal display device according to claim 3,
wherein the photo-alignment film includes a polysiloxane with a photo-functional group and represented by the following formula (25):

### Claim 5 (depends on 3)

The liquid crystal display device according to claim 3,
wherein the photo-alignment film further contains a second polymer, and
the second polymer contains a hydrophobic group.

### Claim 6 (depends on 5)

The liquid crystal display device according to claim 5,
wherein the second polymer is represented by the following formula (14):
wherein H surrounded by a solid line represents a C4 or greater alkyl, alkenyl, or aralkyl group or a C4 or greater monovalent monocyclic or polycyclic hydrocarbon group; A represents a hydrogen atom, an OH group, a COOH group, or a NH2 group; a -Sp- group represents a —O— group, a —S— group, a —NH— group, a —CO— group, a —COO— group, a —OCO— group, a —NHCO— group, a —CONH— group, or a direct bond; Z represents a hydrogen atom, a CH3 group, or a C2H5 group; p shows the degree of polymerization and is an integer of 1 or greater; and n is any value falling within the range of 0 to 1.

### Claim 7 (depends on 6)

The liquid crystal display device according to claim 6,
wherein the second polymer is represented by the following formula (23) or (24):

### Claim 8 (depends on 5)

The liquid crystal display device according to claim 5,
wherein the second polymer is a polymer containing a monomer unit derived from a monomer represented by the following formula (17):
wherein P's are the same as or different from each other and each represent an acryloyloxy group, a methacryloyloxy group, an acryloylamino group, or a methacryloylamino group; A3 represents a trivalent hydrocarbon group; A4 represents a phenylene group; a —CH2— group in each of A3 and A4 may be replaced by a —O— group or a —S— group unless the —CH2— group neighbors another one; a —CH═ group in each of A3 and A4 may be replaced by a —N═ group unless the —CH═ group neighbors another one; a hydrogen atom in each of A3 and A4 may be replaced by a fluorine atom, a chlorine atom, a —CN group, or a C1 to C12 alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, or alkylcarbonyloxy group, and at least one of their carbon atoms may be replaced by a silicon atom; the alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, or alkylcarbonyloxy group may be linear or branched; the —Z4— group and the —Z5— group are the same as or different from each other and each represent a —O— group, a —S— group, a —NH— group, a —CO— group, a —COO— group, a —OCO— group, a —NHCO— group, a —CONH— group, or a direct bond; L3 represents a C4 or greater alkyl, alkenyl, or aralkyl group or a C4 or greater monovalent monocyclic or polycyclic hydrocarbon group; the alkyl group and the alkenyl group may be linear or branched; at least one hydrogen atom in each of the aralkyl group and the monovalent monocyclic or polycyclic hydrocarbon group may be replaced by a C1 to C8 linear or branched alkyl or alkenyl group; a —CH2— group in each of the alkyl group, the alkenyl group, and the monovalent monocyclic or polycyclic hydrocarbon group may be replaced by a —O— group, a —CO— group, a —COO— group, or a —OCO— group unless oxygen atoms neighbor each other; and n3 is 0 or 1.