Composition for forming thermoset film having photo alignment properties

Patent metadata

Field	Value
Publication number	US-9733519-B2
Application number	US-201013377331-A
Country	US
Kind code	B2
Filing date	Jun 21, 2010
Priority date	Jun 23, 2009
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

A material from which a cured film exhibiting high solvent resistance, liquid crystal-alignment performance, heat resistance and high transparency can be formed. A composition for forming a thermoset film having photo alignment properties, including: a component (A) that is an acrylic copolymer having a photodimerizing moiety and a thermal cross-linking moiety; and a component (B) that is a cross-linking agent.

First claim

The invention claimed is:

1. A composition for forming a thermoset film having photo alignment properties, the composition comprising:
a component (A) that is an acrylic copolymer having a photodimerizing moiety and a thermal cross-linking moiety, the acrylic copolymer being a copolymer of (i) at least one monomer selected from the group consisting of hydroxyl alkyl acrylate and hydroxyl alkyl methacrylate, and (ii) at least one monomer selected from the group consisting of monomers of formula (3) and monomers of formula (4):

wherein:
X 1 is a hydrogen atom, a C 1-18 alkyl group, a phenyl group optionally substituted with a halogen atom or a cyano group, or a biphenyl group optionally substituted with a halogen atom or a cyano group,
X 2 is a hydrogen atom, a cyano group, a C 1-18 alkyl group, a phenyl group, a biphenyl group, or a cyclohexyl group, provided that the C 1-18 alkyl group, the phenyl group, the biphenyl group, and the cyclohexyl group may optionally be bonded through a covalent bond, an ether bond, an ester bond, an amide bond, or a urea bond,
each of X 3 and X 5 is independently a single bond, a branched or straight chain C 1-20 alkylene group, an aromatic ring group, or an aliphatic ring group, and
each of X 4 and X 6 is a polymerizable group; and
a component (B) that is a cross-linking agent selected from the group consisting of an alkoxymethylated glycoluril; an alkoxymethylated benzoguanamine; an alkoxymethylated melamine; a compound obtained by condensation of a melamine compound, a urea compound, a glycoluril compound, or a benzoguanamine compound in which a hydrogen atom of such an amino group is substituted by a methylol group or an alkoxymethyl group; and a polymer produced using acrylamide compounds or methacrylamide compounds that are substituted with a hydroxymethyl group or an alkoxymethyl group,
wherein the composition is curable by heating at a temperature of 70 to 160° C. for 0.3 to 60 minutes to form said thermoset film having photo alignment properties, and
the composition exhibits photo alignment properties after exposure to perpendicular irradiation with linear polarization at 313 nm of 30 mJ/cm 2 or less.

2. The composition for forming a thermoset film having photo alignment properties according to claim 1 , further comprising a component (C) that is an acid or a thermal acid generator.

3. The composition for forming a thermoset film having photo alignment properties according to claim 1 , further comprising a component (D) that is a sensitizer.

4. The composition for forming a thermoset film having photo alignment properties according to claim 1 , wherein the composition contains the component (B) in an amount of 1 to 40 part(s) by mass based on 100 parts by mass of the component (A).

5. The composition for forming a thermoset film having photo alignment properties according to claim 2 , wherein the composition contains the component (B) in an amount of 1 to 40 part(s) by mass and the component (C) in an amount of 0.01 to 5 parts by mass based on 100 parts by mass of the component (A).

6. The composition for forming a thermoset film having photo alignment properties according to claim 3 , wherein the composition contains the component (D) in an amount of 0.1 to 20 parts by mass based on 100 parts by mass of the component (A).

7. A liquid crystal alignment layer formed from the composition for forming a thermoset film having photo alignment properties as claimed in claim 1 .

8. An optical device comprising:
a liquid crystal alignment layer formed from the composition for forming a thermoset film having photo alignment properties as claimed in claim 1 ; and
a retardation layer on the liquid crystal alignment layer.

9. The composition for forming a thermoset film having photo alignment properties according to claim 1 , wherein the component B is a cross-linking agent selected from the group consisting of an alkoxymethylated glycoluril; an alkoxymethylated benzoguanamine; an alkoxymethylated melamine; a compound obtained by condensation of a melamine compound, a urea compound, a glycoluril compound, or a benzoguanamine compound in which a hydrogen atom of such an amino group is substituted by a methylol group or an alkoxymethyl group; and a polymer produced using acrylamide compounds or methacrylamide compounds that are substituted with an alkoxymethyl group.

10. The composition for forming a thermoset film having photo alignment properties according to claim 1 , wherein the composition is curable by heating at a temperature of 80 to 140° C. for 0.5 to 10 minutes to form said thermoset film having photo alignment properties.

11. The composition for forming a thermoset film having photo alignment properties according to claim 1 , wherein each X 4 and X 6 is independently selected from the group consisting of an acryloyl group, a methacryloyl group, a styrene group, a maleimide group, an acrylamide group, and a methacrylamide group.

12. The composition for forming a thermoset film having photo alignment properties according to claim 1 , wherein the at least one monomer selected from the group consisting of hydroxyl alkyl acrylate and hydroxyl alkyl methacrylate is selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, 2,3-dihydroxypropyl acrylate, and 2,3-dihydroxypropyl methacrylate.

Assignees

• Hatanaka Tadashi
• Adachi Isao
• Nissan Chemical Ind Ltd

Inventors

• Hatanaka Tadashi
• Adachi Isao

Classifications

• C08L33/066

  containing -OH groups · CPC title

• G02F2202/025

  thermocurable · CPC title

• C08F220/302

  and two or more oxygen atoms in the alcohol moiety · CPC title

• C09K19/56

  Aligning agents · CPC title

• B32B2457/202

  LCD, i.e. liquid crystal displays · CPC title