US4381886A — Liquid crystal display element

Claim 1

Independent Claim 78 words

In a liquid crystal display element comprising substrates having electrodes and liquid crystal orientation controlling films on the sides thereof facing a liquid crystal layer and one or more liquid crystal layers interposed between said substrates, the improvement wherein the liquid crystal orientation controlling film is made from a copolymer having structural units of the formulae: ##STR30## wherein Ar 1 is a dihydrazide residue; Ar 2 is a tetracarboxylic acid residue; and Ar 3 is a diamine residue.

Claim 2

Dependent Claim 78 words

In a liquid crystal display element comprising substrates having electrodes and liquid crystal orientation controlling films on the sides thereof facing a liquid crystal layer and one or more liquid crystal layers interposed between said substrates, the improvement wherein the liquid crystal orientation controlling film is made from a copolymer having structural units of the formulae: ##STR30## wherein Ar 1 is a dihydrazide residue; Ar 2 is a tetracarboxylic acid residue; and Ar 3 is a diamine residue.

Claim 3

Dependent Claim 40 words

A liquid crystal display element according to claim 1, wherein the dihydrazide residue Ar 1 is ##STR31## in which X is --O--, --CH 2 --, --SO 2 --, --CO-- or --S--; and n is an integer of 1 to 8.

Claim 4

Dependent Claim 32 words

A liquid crystal display element according to claim 1, wherein the tetracarboxylic acid residue Ar 2 is ##STR32## in which X is --O--, --SO 2 --, --CO--, ##STR33## or --CH 2 --.

Claim 5

Dependent Claim 54 words

A liquid crystal display element according to claim 1, wherein the diamine residue Ar 3 is ##STR34## in which X is --O--, --CH 2 --, --SO 2 --, --CO--, --S--, or ##STR35## Y is an alkylene group, an alkyl group or a phenylene group; and Z is an alkyl group or an aryl group.

Claim 6

Dependent Claim 209 words

In a liquid crystal display element comprising substrates having electrodes and liquid crystal orientation controlling films on the sides thereof facing a liquid crystal layer and one or more liquid crystal layers interposed between said substrates, the improvement wherein the liquid crystal orientation controlling film is made from a copolymer produced by reacting a dihydrazide of the formula: ##STR36## wherein Ar 1 is a dihydrazide residue, a diamine of the formula: H.sub.2 N--Ar.sub.3 --NH.sub.2 wherein Ar 3 is a diamine residue, and a tetracarboxylic acid dianhydride of the formula: ##STR37## wherein Ar 2 is a tetracarboxylic acid residue, in a solvent at a temperature of 50° C. or less to form a polyhydrazide acid-amide acid having structural units of the formulae: ##STR38## wherein Ar 1 , Ar 2 and Ar 3 are as defined above; and values of m and n are those which can give a reduced viscosity (η sp/c ) of 0.1 dl/g or more measured by using dimethyl sulfoxide as a solvent in a concentration of 0.1 g/l at 30° C., said polyhydrazide acid-amide acid being subjected to ring closure with heating to give the copolymer having structural units of the formulae: ##STR39## wherein Ar 1 , Ar 2 and Ar 3 are as defined above.

Claim 7

Dependent Claim 209 words

In a liquid crystal display element comprising substrates having electrodes and liquid crystal orientation controlling films on the sides thereof facing a liquid crystal layer and one or more liquid crystal layers interposed between said substrates, the improvement wherein the liquid crystal orientation controlling film is made from a copolymer produced by reacting a dihydrazide of the formula: ##STR36## wherein Ar 1 is a dihydrazide residue, a diamine of the formula: H.sub.2 N--Ar.sub.3 --NH.sub.2 wherein Ar 3 is a diamine residue, and a tetracarboxylic acid dianhydride of the formula: ##STR37## wherein Ar 2 is a tetracarboxylic acid residue, in a solvent at a temperature of 50° C. or less to form a polyhydrazide acid-amide acid having structural units of the formulae: ##STR38## wherein Ar 1 , Ar 2 and Ar 3 are as defined above; and values of m and n are those which can give a reduced viscosity (η sp/c ) of 0.1 dl/g or more measured by using dimethyl sulfoxide as a solvent in a concentration of 0.1 g/l at 30° C., said polyhydrazide acid-amide acid being subjected to ring closure with heating to give the copolymer having structural units of the formulae: ##STR39## wherein Ar 1 , Ar 2 and Ar 3 are as defined above.

Claim 8

Dependent Claim 40 words

A liquid crystal display element according to claim 5, wherein the dihydrazide residue Ar 1 is ##STR40## in which X is --O--, --CH 2 --, --SO 2 --, --CO-- or --S--; and n is an integer of 1 to 8.

Claim 9

Dependent Claim 74 words

A liquid crystal display element according to claim 5, wherein the dihydrazide is at least one member selected from the group consisting of isophthalic acid dihydrazide, terephthalic acid dihydrazide, 4,4'-oxybis(benzoic acid hydrazide), 4,4'-sulfonyl-bis-(benzoic acid hydrazide), 3,3'-sulfonyl-bis(benzoic acid hydrazide), 4,4'-methylene-bis(benzoic acid hydrazide), 4,4'-carbonyl-bis(benzoic acid hydrazide), 4,4'-biphenyl-di(carbonyl hydrazide), oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, pimelic acid dihydrazide, suberic acid dihydrazide, azelaic acid dihydrazide and sebacic acid dihydrazide.

Claim 10

Dependent Claim 32 words

A liquid crystal display element according to claim 5, wherein the tetracarboxylic acid residue Ar 2 is ##STR41## in which X is --O--, --SO 2 --, --CO--, ##STR42## or --CH 2 --.

Claim 11

Dependent Claim 52 words

A liquid crystal display element according to claim 5, wherein the tetracarboxylic acid dianhydride is at least one member selected from the group consisting of pyromellitic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, cyclopentanetetracarboxylic dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, 2,3,5,6-pyridinetetracarboxylic dianhydride, 4,4'-sulfonyldi(phthalic anhydride), 4,4'-oxydi(phthalic anhydride), 4,4'-carbonyl-di(phthalic anhydride), and 4,4'-isopropylidene-di(phthalic anhydride).

Claim 12

Dependent Claim 54 words

A liquid crystal display element according to claim 5, wherein the diamine residue Ar 3 is ##STR43## in which X is --O--, --CH 2 --, --SO 2 --, --CO--, --S-- or ##STR44## Y is an alkylene group, an alkyl group or a phenylene group; and Z is an alkyl group or an aryl group.

Claim 13

Dependent Claim 46 words

A liquid crystal display element according to claim 5, wherein the diamine is at least one member selected from the group consisting of m-phenylenediamine, p-phenylenediamine, 4,4'-diaminodiphenyl ether, benzidine, 4,4'-diaminoterphenyl, 4,4'-oxydianiline, 3,4'-oxydianiline, 4,4'-methylenedianiline, 4,4'-sulfonyldianiline, 3,3'-sulfonyldianiline, 3,3'-carbonyldianiline, 4,4'-thiodianiline, bis[4-(p-aminophenoxy)phenyl]ether, bis[4-(p-aminophenoxy)phenyl]methane, bis[4-(m-aminophenoxy)phenyl]sulfone, bis[4-(p-aminophenoxy)phenyl]sulfone, 4,4'-bis(p-aminophenoxy)benzophenone, bis[4-(p-aminophenoxy)phenyl]sulfide, bis[4-(p-aminophenoxy)phenyl]propane, 4,4'-diamino-3-carbamoyldiphenyl ether, ##STR45##

Claim 14

Dependent Claim 57 words

A liquid crystal display element according to claim 5, wherein the dihydrazide is at least one member selected from the group consisting of isophthalic acid dihydrazide, terephthalic acid dihydrazide, adipic acid dihydrazide, and sebacic acid dihydrazide; the diamine is at least one member selected from the group consisting of p-phenylenediamine, 4,4'-diaminodiphenyl sulfone, 4,4'-bis(m-aminophenoxy)-diphenyl sulfone, 4,4'-diamino-3-carbamoyldiphenyl ether, ##STR46##

Claim 15

Dependent Claim 37 words

4'-diaminodiphenylmethane, 4,4'-bis(p-aminophenoxy)-diphenyl sulfone, m-phenylenediamine, 4,4'-bis(p-aminophenoxy)-diphenyl-propane, ##STR47## NH 2 , and 4,4'-diaminidiphenyl ether; and the tetracarboxylic acid dianhydride is at least one member selected from the group consisting of pyromellitic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, and 3,3',4,4'-diphenyltetracarboxylic dianhydride.

Claim 16

Dependent Claim 37 words

4'-diaminodiphenylmethane, 4,4'-bis(p-aminophenoxy)-diphenyl sulfone, m-phenylenediamine, 4,4'-bis(p-aminophenoxy)-diphenyl-propane, ##STR47## NH 2 , and 4,4'-diaminidiphenyl ether; and the tetracarboxylic acid dianhydride is at least one member selected from the group consisting of pyromellitic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, and 3,3',4,4'-diphenyltetracarboxylic dianhydride.

Claim 17

Dependent Claim 139 words

In a liquid crystal display element comprising substrates having electrodes and liquid crystal orientation controlling films on the sides thereof facing a liquid crystal layer and one or more liquid crystal layers interposed between said substrates, the improvement wherein the liquid crystal orientation controlling film is produced by using a varnish comprising (a) a polyhydrazide acid-amide acid having structural units of the formulae: ##STR48## wherein Ar 1 is a dihydrazide residue; Ar 2 is a tetracarboxylic acid residue; Ar 3 is a diamine residue; and values of m and n are those which can give a reduced viscosity (η sp/c ) of 0.1 dl/g or more measured by using dimethyl sulfoxide as a solvent in a concentration of 0.1 g/l at 30° C., and (b) a solvent, and heating said varnish for removing the solvent and conducting ring closure.

Claim 18

Dependent Claim 139 words

In a liquid crystal display element comprising substrates having electrodes and liquid crystal orientation controlling films on the sides thereof facing a liquid crystal layer and one or more liquid crystal layers interposed between said substrates, the improvement wherein the liquid crystal orientation controlling film is produced by using a varnish comprising (a) a polyhydrazide acid-amide acid having structural units of the formulae: ##STR48## wherein Ar 1 is a dihydrazide residue; Ar 2 is a tetracarboxylic acid residue; Ar 3 is a diamine residue; and values of m and n are those which can give a reduced viscosity (η sp/c ) of 0.1 dl/g or more measured by using dimethyl sulfoxide as a solvent in a concentration of 0.1 g/l at 30° C., and (b) a solvent, and heating said varnish for removing the solvent and conducting ring closure.

Claim 19

Dependent Claim 32 words

A liquid crystal display element according to claim 13, wherein the solvent is at least one member selected from the group consisting of N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, hexamethylphosphoramide, dimethyl sulfoxide and sulfolane.

Claim 20

Dependent Claim 40 words

A liquid crystal display element according to claim 13, wherein the dihydrazide residue Ar 1 is ##STR49## in which X is --O--, --CH 2 --, --SO 2 --, --CO-- or --S--; and n is an integer of 1 to 8.

Claim 21

Dependent Claim 32 words

A liquid crystal display element according to claim 13, wherein the tetracarboxylic acid residue Ar 2 is ##STR50## in which X is --O--, --SO 2 --, --CO--, ##STR51## or --CH 2 --.

Claim 22

Dependent Claim 55 words

A liquid crystal display element according to claim 13, wherein the diamine residue Ar 3 , is ##STR52## in which X is --O--, --CH 2 --, --SO 2 --, --CO--, --S-- or ##STR53## Y is an alkylene group, an alkyl group or a phenylene group; and Z is an alkyl group or an aryl group.

Claim 23

Dependent Claim 21 words

A liquid crystal display element according to claim 13, wherein the varnish further contains (c) one ore more silane coupling agents.

Claim 24

Dependent Claim 18 words

A liquid crystal display element according to claim 18, wherein the silane coupling agent is γ-aminopropyltriethoxysilane or γ-glycidoxypropyltrimethoxysilane.

Claim 25

Dependent Claim 22 words

A liquid crystal display element according to claim 1, 5 or 13, wherein the liquid crystal display element has a multi-layer structure.

Claim 26

Dependent Claim 31 words

A liquid crystal display element according to claim 1, 5 or 13, wherein a film of silane coupling agent is formed between the electrode and the liquid crystal orientation controlling film.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1986-05-02	1986-11-01	1987-05-03	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1990-05-02	1990-11-01	1991-05-03	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1994-05-02	1994-11-01	1995-05-03	$7700.00	Window Closed / Lapsed

Liquid crystal display element

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