# US 5,350,539 A · Alignment treating agent for liquid crystal cell

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- Number: US 5,350,539 A
- Document ID: US5350539A
- Status: Granted
- Kind: A
- Application number: 07/925,670
- Filed: 1992-08-07
- Granted: 1994-09-27
- Earliest claimed: 1991-08-13
- Assignees: Nissan Chemical Industries, Ltd.
- Inventors: Makoto Mishina; Toyohiko Abe
- Web page: https://patentgrep.com/patent/US5350539A

## CPC

- C08G 73/1067: {Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound}
- G02F 1/133723: {Polyimide, polyamide-imide}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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

The present invention relates to an alignment treating agent for a liquid crystal cell, which comprises an organic solvent-soluble polyimide resin comprising a tetracarboxylic acid and a diamine, at least 10 mol % of the diamine having a bivalent organic group selected from the group consisting of: ##STR1## The aligned film for a liquid crystal using the solvent-soluble polyimide resin of the present invention does not require a heat treatment at a high temperature at the time of forming a resin film and enables to use a substrate poor in heat-resistance, and alignment properties such as a tilt angle and a voltage maintenance of the aligned film are not deteriorated even after durability test at a high temperature.

## Claims

### Claim 1

An alignment treating agent for a liquid crystal cell, which comprises an organic solvent-soluble polyimide resin having a reduced viscosity of from 0.05 to 3.0 dl/g (concentration: 0.5 g/dl in N-methylpyrrolidone at 30.degree. C.) and having the formula (1): ##STR7## wherein R.sub.1 is a tetravalent organic group constituting a tetracarboxylic acid and its derivative, R.sub.2 is a bivalent organic group constituting a diamine and at least 10 mol. % of R.sub.2 is a bivalent organic group selected from the group consisting of ##STR8## wherein X is selected from the group consisting of hydrogen, methyl and methoxy.

### Claim 2 (depends on 1)

The alignment treating agent for a liquid crystal cell according to claim 1, wherein at least 10 mol % of R.sub.2 is a bivalent organic group constituting a diamine selected from the group consisting of aromatic diamines including p-phenylene diamine, 2,5-diaminotoluene, 4,4'-diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dimethoxy-4,4'-diaminobiphenyl, 1,4-bis(4-aminophenyl)benzene and 9,10-bis(4-aminophenyl)anthracene.

### Claim 3 (depends on 1)

The alignment treating agent for a liquid crystal cell according to claim 1, wherein
(i) R.sub.1 is a tetravalent organic group constituting a tetracarboxylic acid and its derivative selected from the group consisting of aromatic tetracarboxylic acids including 3,3',4,4'-biphenyltetracarboxylic acid, 2,3,3',4-biphenyltetracarboxylic acid, bis(3,4-dicarboxyphenyl)ether, 3,3',4,4'-benzophenonetetracarboxylic acid, bis(3,4-dicarboxyphenyl)sulfone, bis(3,4-dicarboxyphenyl)methane, 2,2-bis(3,4-dicarboxyphenyl)propane, 1,1,1,3,3,3-hexafluoro-2,2bis(3,4-2,2-bis(3,4-dicarboxyphenyl)propane, bis(3,4-dicarboxyphenyl)dimethylsilane, bis(3,4-dicarboxyphenyl)diphenylsilane, 2,3,4,5-pyridinetetracarboxylic acid and 2,6-bis(3,4-dicarboxyphenyl)pyridine, and their dianhydrides, and their dicarboxylic acid diacid halides; cycloaliphatic tetracarboxylic acids including cyclobutanetetracarboxylic acid, cyclopentanetetracarboxylic acid, cyclohexanetetracarboxylic acid, 2,3,5-tricarboxycyclopentylacetic acid and 3,4-dicarboxy-1,2,3,4-tetrahydro-1-naphthalenesuccinic acid, and their dianhydrides, and their dicarboxylic acid diacid halides; and aliphatic tetracarboxylic acids including butanetetracarboxylic acid, and their dianhydrides, and their dicarboxylic acid diacid halides; and
(ii) at least 10 mol % of R.sub.2 is a bivalent organic group constituting a diamine selected from the group consisting of aromatic diamines including p-phenylene diamine, 2,5-diaminotoluene, 4,4'-diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dimethoxy-4,4'-diaminobiphenyl, 1,4-bis(4-aminophenyl)benzene and 9,10-bis(4-aminophenyl)anthracene;
and the remaining part of R.sub.2 is a bivalent organic group constituting a primary diamine selected from the group consisting of aromatic diamines including diaminodiphenylmethane, diaminodiphenylether, 2,2-diaminodiphenylpropane, bis(3,5-diethyl-4-aminophenyl)methane, diaminodiphenylsulfone, diaminobenzophenone, diaminonaphthalene, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 4,4'-bis(4-aminophenoxy)diphenylsulfone, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 2,2-bis(4-aminophenyl)hexafluoropropane and 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane; cycloaliphatic diamines including bis(4-aminocyclohexyl)methane and bis(4-amino-3-methylcyclohexyl)methane; aliphatic diamines including tetramethylenediamine and hexamethylenediamine; and diaminosiloxanes having the formula, ##STR9## (wherein n is an integer of from 1 to 10).

### Claim 4 (depends on 1)

The alignment treating agent for a liquid crystal cell according to claim 1, wherein R.sub.2 further includes a bivalent organic group constituting a long chain alkyl-containing diamine selected from the group consisting of: ##STR10## (wherein n is an integer of from 3 to 21).

### Claim 5 (depends on 1)

The alignment treating agent for a liquid crystal cell according to claim 1, wherein at least 20 mol % of R.sub.2 is a bivalent organic group selected from the group consisting of ##STR11## wherein X is selected from the group consisting of hydrogen, methyl and methoxy.

### Claim 6 (depends on 1)

The alignment treating agent for a liquid crystal cell according to claim 1, wherein at least 50 mol % of R.sub.2 is a bivalent organic group selected from the group consisting of ##STR12## wherein X is selected from the group consisting of hydrogen, methyl and methoxy.