Liquid crystal aligning agent, liquid crystal alignment film, and liquid crystal display element

Patent metadata

Field	Value
Publication number	US-11111387-B2
Application number	US-201615748461-A
Country	US
Kind code	B2
Filing date	Jul 29, 2016
Priority date	Jul 30, 2015
Publication date	Sep 7, 2021
Grant date	Sep 7, 2021

Abstract

The present invention relates to a polymer composition which contains (A) a photosensitive side-chain polymer that exhibits liquid crystallinity in a predetermined temperature range and has a repeating unit comprising a vertically aligning group, and (B) an organic solvent. The present invention provides: a liquid crystal alignment film which has excellent tilt angle characteristics, while being provided with alignment controllability with high efficiency; a polymer composition which enables the achievement of this liquid crystal alignment film; a twisted nematic liquid crystal display element; and a vertical field switching mode liquid crystal display element.

First claim

What is claimed is:

1. A polymer composition, comprising:
(A) a side chain polymer which is a photosensitive side chain polymer exhibiting liquid crystallinity in a predetermined temperature range and has a repeating unit comprising from 0.1 to 50 mol % of a vertically alignable group; and
(B) an organic solvent;
wherein the vertically alignable group is
at least one member selected from the group consisting of alkyl having 6 to 17 carbon atoms:
wherein component (A) comprises one or more photosensitive sidechains of the following formula:

wherein A, B, and D each independently represent a single bond, —O—, —CH 2 —, —COO—, —OCO—, —CONH—, —NH—CO—, —CH═CH—CO—O—, or —O—CO—CH═CH—;
S represents an alkylene group having 1 to 12 carbon atoms, and a hydrogen atom bonded thereto may be replaced with a halogen group;
T represents a single bond or an alkylene group having 1 to 12 carbon atoms, and a hydrogen atom bonded thereto may be replaced with a halogen group;
Y 2 represents a group selected from the group consisting of a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and a combination thereof, and hydrogen atoms bonded thereto may be each independently substituted with —NO 2 , —CN, —CH═C(CN) 2 , —CH═CH—CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms;
R represents hydroxy;
P and Q each independently represent a group selected from the group consisting of a divalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a pyrrole ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and a combination thereof, and when X is CH═CH—CO—O— or —O—CO—CH═CH—, P or Q on a side to which —CH═CH— is bonded is an aromatic ring; and
l1 represents 0 or 1;
l2 represents an integer of 0 to 2;
when both l1 and l2 are 0, A also represents a single bond when T is a single bond;
when l1 is 1, B also represents a single bond when T is a single bond.

2. The polymer composition of claim 1 , wherein the component (A) has one or a plurality of liquid crystalline side chains selected from the group consisting of the following formulae (21) to (31):

wherein:
A and B each independently represent a single bond, —O—, —CH 2 —, —COO—, —OCO—, —CONH—, —NH—CO—, —CH═CH—CO—O—, or —O—CO—CH═CH—;
Y 3 is a group selected from the group consisting of a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing heterocyclic ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, and a combination thereof, and hydrogen atoms bonded thereto may be each independently substituted with —NO 2, —CN, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an alkyloxy group having 1 to 5 carbon atoms;
R 3 represents a hydrogen atom, —NO 2 , —CN, —CH═C(CN) 2 , —CH═CH—CN, a halogen group, a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing heterocyclic ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms;
one of q1 and q2 is 1 and the other is 0;
l represents an integer of 1 to 12, and m represents an integer of 0 to 2, provided that the sum of all ms in the formulae (23) and (24) is 2 or more, the sum of all ms in the formulae (25) and (26) is 1 or more, and m1, m2, and m3 each independently represent an integer of 1 to 3;
R 2 represents a hydrogen atom, —NO 2 , —CN, a halogen group, a monovalent benzene ring, a naphthalene ring, a biphenyl ring, a furan ring, a nitrogen-containing heterocyclic ring, an alicyclic hydrocarbon having 5 to 8 carbon atoms, an alkyl group, or an alkyloxy group; and
Z 1 and Z 2 , each represent a single bond, —CO—, —CH 2 O—, —CH═N—, or —CF 2 —.

3. A method for producing a substrate comprising a liquid crystal alignment film having an alignment control ability, wherein the liquid crystal alignment film is obtained by a method comprising:
[I] applying the composition according to claim 1 onto a substrate having an electrode for driving a liquid crystal to form a coating film;
[II] irradiating the coating film obtained in [I] with polarized ultraviolet light in an oblique direction; and
[III] heating the coating film obtained in [II].

4. A substrate comprising the liquid crystal alignment film produced by the method according to claim 3 .

5. A twisted nematic type liquid crystal display element, comprising the substrate according to claim 4 .

6. A method for producing a twisted nematic type liquid crystal display element, wherein the liquid crystal display element is obtained by a method comprising:
preparing a first substrate, which is the substrate according to claim 4 ;
obtaining a second substrate comprising a liquid crystal alignment film having alignment control ability in which the liquid crystal alignment film is obtained by a method comprising
[I′] applying the polymer composition on a second substrate to form a coating film,
[II′] irradiating the coating film obtained in [I′] with polarized ultraviolet light,
[III′] heating the coating film obtained in [II′], and
[IV] obtaining a liquid crystal display element by arranging the first substrate and the second substrate to oppose each other such that the liquid crystal alignment films of the first substrate and the second substrate oppose each other through liquid crystal and directions of liquid crystal alignment are orthogonal to each other.

7. A twisted nematic type liquid crystal display element, produced by the method according to claim 6 .

8. The polymer composition if claim 1 wherein the vertically alignable group is at least one member selected from the group consisting of C 6 H 13 , C 12 H 25 , and C 16 H 33 .

9. The polymer composition of claim 8 wherein the vertically alignable group is C 6 H 13 .

10. The polymer composition of claim 8 wherein the vertically alignable group is C 12 H 25 .

11. The polymer composition of claim 8 wherein the vertically alignable group is C 16 H 33 .

Assignees

• Nissan Chemical Ind Ltd

Inventors

• Nagi Tatsuya

Classifications

• G02F1/133711

  by organic films, e.g. polymeric films · CPC title

• G02F1/133703

  by introducing organic surfactant additives into the liquid crystal material · CPC title

• G02F1/1337

  Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers · CPC title

• C09K2323/02

  Alignment layer characterised by chemical composition · CPC title

• C09K2019/548

  stabilizing the alignment; Polymer stabilized alignment · CPC title