Liquid crystal aligning agents for forming photo-aligning liquid crystal alignment layers, liquid crystal alignment layers and liquid crystal display devices using the same

Patent metadata

Field	Value
Publication number	US-9909065-B2
Application number	US-201314395578-A
Country	US
Kind code	B2
Filing date	Apr 10, 2013
Priority date	Apr 24, 2012
Publication date	Mar 6, 2018
Grant date	Mar 6, 2018

Abstract

A photo-aligning liquid crystal aligning agent for forming a liquid crystal alignment layer capable of materializing a liquid crystal display device, which has a high transmittance while maintaining a liquid crystal aligning property, a voltage holding ratio and the like, and in which flickering is inhibited from being caused after operating for a long time. The photo-aligning liquid crystal aligning agent contains [A] polyamic acid or a derivative thereof which is synthesized by reacting tetracarboxylic acid dianhydride and diamine, and [B] polyamic acid or a derivative thereof obtained by reacting tetracarboxylic acid dianhydride having no photoreactive structure and diamine having no photoreactive structure.

First claim

What is claimed is:

1. A photo-aligning liquid crystal aligning agent containing:
[A] polyamic acid or a derivative thereof having a photoreactive structure which is synthesized by reacting tetracarboxylic acid dianhydride and diamine, wherein the tetracarboxylic acid dianhydride and the diamine contain at least one tetracarboxylic acid dianhydride having a photoreactive structure and diamine having a photoreactive structure which are selected from the group of compounds represented by the following Formulas (I) to (VII), and at least one tetracarboxylic acid dianhydride having no photoreactive structure selected from the group of compounds represented by the following Formulas (AN-I) to (AN-VII), wherein a compound represented by the following Formula (AN-4-17) is required, and
[B] polyamic acid or a derivative thereof obtained by reacting tetracarboxylic acid dianhydride having no photoreactive structure and diamine having no photoreactive structure:
R 2 —C≡C—R 3   (I)

R 2 —C≡C—C≡C—R 3   (II)

R 2 —C≡C—CH═CH—R 3   (III)

R 2 —C≡C—R 4 —C≡C—R 3   (IV)

R 2 —C≡C—R 4 —CH═CH—R 3   (V)

R 2 —CH═CH—R 3   (VI)

R 2 —N═N—R 3   (VII)

in Formulas (I) to (VII), R 2 and R 3 each are independently a monovalent organic group having —NH 2 or a monovalent organic group having —CO—O—CO—, and R 4 is a divalent organic group having an aromatic ring,

in Formulas (AN-I), (AN-IV) and (AN-V), plural X each are independently a single bond or —CH 2 —;
in Formula (AN-II), G is a single bond, alkylene having 1 to 20 carbon atoms, —CO—, —O—, —S—, —SO 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 —; in Formulas (AN-II) to (AN-IV), plural Y each are independently one selected from the group of the following trivalent groups:

at least one hydrogen of the above groups may be substituted with methyl, ethyl or phenyl;
in Formulas (AN-III) to (AN-V), a ring A is a monocyclic hydrocarbon group having 3 to 10 carbon atoms or a condensed polycyclic hydrocarbon group having 6 to 30 carbon atoms; at least one hydrogen of the above group may be substituted with methyl, ethyl or phenyl; an atomic bonding coupled with the ring is connected with optional carbon constituting the ring, and two atomic bondings may be connected with the same carbon;
in Formula (AN-VI), X 10 is alkylene having 2 to 6 carbon atoms; Me represents methyl; and Ph represents phenyl;
in Formula (AN-VII), plural G 10 each are independently —O—, —COO— or —OCO—; and plural r each are independently 0 or 1;

in Formula (AN-4-17), m is 8;
wherein in [B], the diamine having no photoreactive structure is at least one selected from the group of compounds represented by the following Formulas (DI-1) to (DI-12), wherein at least one compound represented by the following Formulas (DI-5-29) and (DI-9-1) is required,

in Formula (DI-1), m is an integer of 1 to 12;
in Formulas (DI-3), (DI-5), (DI-6) and (DI-7), plural G 21 each are independently a single bond, 13 NH—, —O—, —S—, —S—S—, —SO 2 —, CO—, —CONH—, —NHCO—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —(CH 2 ) m′ —, —O—(CH 2 ) m′ —O—, —N(CH 3 )—C(CH 2 ) k —N(CH 3 )— or —S—(CH 2 ) m′ —S—; plural m′ each are independently an integer of 1 to 12, and k is an integer of 1 to 5;
in Formulas (DI-6) and (DI-7), plural G 22 each are independently a single bond, —O—, —S—, CO—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 — or alkylene having 1 to 10 carbon atoms;

at least one hydrogen of a cyclohexane ring and a benzene ring in Formulas (DI-2) to (DI-7) may be substituted with —F, —CH 3 , —OH, —CF 3 , —CO 2 H—, —CONH 2 or benzyl, and in addition thereto, in Formula (DI-4), at least one hydrogen of the benzene ring may be substituted with at least one of group represented the following Formulas (DI-4-a) to (DI-4-c):

in Formulas (DI-4-a) and (DI-4-b), plural R 20 each are independently hydrogen or —CH 3 ;
in Formulas (DI-2) to (DI-7), groups in which bonding positions are not fixed to any of carbon atoms constituting the rings show that the bonding positions thereof in the rings are optional; and the bonding position of —NH 2 in the cyclohexane ring or the benzene ring is an optional position excluding the bonding position of G 21 or G 22 ;

in Formula (DI-8), R 21 and R 22 each are independently alkyl having 1 to 3 carbon atoms or phenyl;

plural G 23 each are independently alkylene having 1 to 6 carbon atoms, phenylene or phenylene substituted with alkyl;
w is an integer of 1 to 10;
in Formula (DI-9), plural R 23 each are independently alkyl having 1 to 5 carbon atoms, alkoxy having 1 to 5 carbon atoms or Cl;

plural p each are independently an integer of 0 to 3, and q is an integer of 0 to 4;
in Formula (DI-10), R 24 is hydrogen, alkyl having 1 to 4 carbon atoms, phenyl or benzyl;
in Formula (DI-11), G 24 is —CH 2 — or —NH—;
in Formula (DI-12), G 25 is a single bond, alkylene having 2 to 6 carbon atoms or 1,4-phenylene; and r is 0 or 1;
in Formula (DI-12), groups in which bonding positions are not fixed to any of carbon atoms constituting the rings show that the bonding positions thereof in the rings are optional;
in Formulas (DI-9), (DI-11) and (DI-12), the bonding positions of —NH 2 bonded to the benzene rings are optional positions;

in Formula (DI-5-29), k is an integer of 1 to 5.

2. The photo-aligning liquid crystal aligning agent as described in claim 1 , wherein in [A], the photoreactive structure is present in a principal chain of the polyamic acid or the derivative thereof.

3. The photo-aligning liquid crystal aligning agent as described in claim 1 , wherein in [A], the tetracarboxylic acid dianhydride having a photoreactive structure and the diamine having a photoreactive structure are at least one selected from the group of compounds represented by the following Formulas (I-1), (II-1), (III-1), (IV-1), (IV-2), (V-1), (VI-1) and (VII-1) to (VII-3):

in Formulas (I-1), (II-1), (III-1), (IV-1), (V-1), (VI-1), (VII-1) and (VII-2), groups in which bonding positions are not fixed to any of carbon atoms constituting the rings show that the bonding positions thereof in the rings are optional;
in Formula (VII-1), plural R 4 each are independently —CH 3 , —OCH 3 , —CF 3 or —COOCH 3 ; and
plural b each are independently an integer of 0 to 2.

4. The photo-aligning liquid crystal aligning agent as described in claim 3 , wherein in [A], the tetracarboxylic acid dianhydride having a photoreactive structure and the diamine having a photoreactive structure are at least one selected from the group of compounds represented by the following Formulas (II-1-1), (VI-1-1), (VII- 1- 1) and (VII-3):

5. The

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Ooki Youichiro
• Katano Yuko
• Matsuda Tomoyuki
• Izawa Keisuke
• Hisada Rika

Classifications

• G02F1/133723 Primary

  Polyimide, polyamide-imide · CPC title

• C09D179/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• G02F1/133788

  by light irradiation, e.g. linearly polarised light photo-polymerisation · CPC title

• C08G73/1096

  containing azo linkage in the main chain · CPC title

• C08G73/106

  containing silicon · CPC title