Liquid crystal aligning agent, liquid crystal alignment film, method for producing same, liquid crystal element and polymer

Patent metadata

Field	Value
Publication number	US-11061282-B2
Application number	US-201816479921-A
Country	US
Kind code	B2
Filing date	Feb 13, 2018
Priority date	Feb 28, 2017
Publication date	Jul 13, 2021
Grant date	Jul 13, 2021

Abstract

According to the present invention, a liquid crystal aligning agent is configured to contain a polymer (P) which has at least one partial structure selected from the group consisting of a partial structure represented by formula (1) and a partial structure represented by formula (2). In formula (1) and formula (2), X1 represents a tetravalent organic group that has a cyclobutane ring structure, while having at least one substituent in the ring portion of the cyclobutane ring; X2 represents a divalent organic group of a specific structure which has an aliphatic structure and a divalent nitrogen-containing heterocyclic group; and each of R5 and R6 independently represents a hydrogen atom or a monovalent organic group having 1-6 carbon atoms.

First claim

The invention claimed is:

1. A liquid crystal aligning agent comprising a polymer (P) having at least one selected from the group consisting of a partial structure represented by the following Formula (1) and a partial structure represented by the following Formula (2):

In Formula (1) and Formula (2), X 1 is a tetravalent organic group having a cyclobutane ring structure and has at least one substituent in a ring portion of a cyclobutane ring; X 2 is a divalent organic group represented by the following Formula (4); R 5 and R 6 each are independently a hydrogen atom or a monovalent organic group having 1 to 6 carbon atoms,
*-A 1 -Y 1 -Z 1 -Y 2 -A 2 -*  (4)

In Formula (4), A 1 and A 2 each are independently a divalent aromatic ring group and may have a substituent in a ring portion; here, at least one of A 1 and A 2 is a divalent nitrogen-containing heterocyclic group in which two hydrogen atoms are removed from a ring portion of one nitrogen-containing heterocyclic ring selected from the group consisting of a pyridine ring, a pyrazine ring, a pyrimidine ring and a pyridazine ring and may have a substituent in a ring portion; Y 1 and Y 2 each are independently an oxygen atom, a sulfur atom, or —NR 7 —, wherein R 7 is a hydrogen atom or a monovalent organic group; Z 1 is a divalent organic group having an aliphatic structure and 1 to 15 carbon atoms, at least one substituent for Y 1 and Y 2 and Z 1 may be bonded to form a ring structure, and substituents for Y 1 and Y 2 may be bonded to form a ring structure together with Z 1 , and * indicates a bond.

2. The liquid crystal aligning agent according to claim 1 ,
wherein Z 1 is a divalent organic group represented by the following Formula (5):

In Formula (5), R 9 and R 10 each are independently an alkanediyl group, and a total number of carbon atoms for R 9 and R 10 is 1 to 15; here, in Formula (4), at least one substituent for Y 1 and Y 2 and R 9 may be bonded to form a ring structure, at least one substituent for Y 1 and Y 2 and R 10 may be bonded to form a ring structure, and at least one substituent for Y 1 and Y 2 and a substituent for Y 3 may be bonded to form a ring structure together with R 9 or R 10 ; Y 3 is an oxygen atom, a sulfur atom, or —NR 8 —, wherein R 8 is a hydrogen atom or a monovalent organic group; p is an integer of 0 to 4; when p is 2 or more, a plurality of R 9 's and Y 3 's may be the same or different from each other.

3. The liquid crystal aligning agent according to claim 1 ,
wherein X 1 is a tetravalent organic group represented by the following Formula (3):

In Formula (3), R 1 to R 3 each are independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a thioalkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, or —COR 20 , wherein R 20 is an alkyl group having 1 to 6 carbon atoms, a fluorine-containing alkyl group, an alkoxy group or a fluorine-containing alkoxy group; R 4 is a halogen atom, an alkyl group having 1 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a thioalkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, or —COR 20 ; here, adjacent groups among R 1 to R 4 may be bonded to form a ring structure, and * indicates a bond.

4. The liquid crystal aligning agent according to claim 1 ,
wherein A 1 and A 2 are both a divalent nitrogen-containing heterocyclic group in which two hydrogen atoms are removed from a ring portion of one nitrogen-containing heterocyclic ring selected from the group consisting of a pyridine ring, a pyrazine ring, a pyrimidine ring and a pyridazine ring, and
wherein Y 1 and Y 2 are bonded to carbon atoms adjacent to nitrogen atoms in the ring of the nitrogen-containing heterocyclic ring with respect to the nitrogen-containing heterocyclic ring that A 1 and A 2 have.

5. The liquid crystal aligning agent according to claim 4 ,
wherein the nitrogen-containing heterocyclic ring that A 1 and A 2 have is a pyridine ring, and
wherein bonding sites of Y 1 and Y 2 on the pyridine ring are at the ortho position with respect to a nitrogen atom of the pyridine ring and at the para position with respect to a nitrogen atom in Formula (1) and Formula (2) which is bonded to X 2 .

6. The liquid crystal aligning agent according to claim 1 ,
wherein at least one of Y and Y 2 is —NR 7 —.

7. A liquid crystal alignment film formed using the liquid crystal aligning agent according to claim 1 .

8. A method for producing a liquid crystal alignment film, comprising
a photo-alignment process in which a coating film is framed using the liquid crystal aligning agent according to claim 1 , and a light emission treatment is performed on the coating film to impart a liquid crystal alignment ability.

9. The method for producing a liquid crystal alignment film according to claim 8 , further comprising
a contact process in which the coating film subjected to the light emission treatment is brought into contact with water, a water-soluble organic solvent, or a solvent in which water and a water-soluble organic solvent are mixed.

10. The method for producing a liquid crystal alignment film according to claim 9 , further comprising
a heating process in which the coating film subjected to the light emission treatment is heated in a temperature range of 120° C. or higher and 280° C. or lower in at least one of before the contact process and after the contact process.

11. A liquid crystal element comprising the liquid crystal alignment film according to claim 7 .

12. A polymer comprising at least one selected from the group consisting of a partial structure represented by the following Formula (1) and a partial structure represented by the following Formula (2):

In Formula (1) and Formula (2), X 1 is a tetravalent organic group having a cyclobutane ring structure and has at least one substituent in a ring portion of a cyclobutane ring; X 2 is a divalent organic group represented by the following Formula (4); R 5 and R 6 each are independently a hydrogen atom or a monovalent organic group having 1 to 6 carbon atoms,
*-A 1 -Y 1 -Z 1 -Y 2 -A 2 -*  (4)

In Formula (4), A 1 and A 2 each are independently a divalent aromatic ring group and may have a substituent in a ring portion; here, at least one of A 1 and A 2 is a divalent nitrogen-containing heterocyclic group in which two hydrogen atoms are removed from a ring portion of one nitrogen-containing heterocyclic ring selected from the group consisting of a pyridine ring, a pyrazine ring, a pyrimidine ring and a pyridazine ring and may have a substituent in a ring portion; Y 1 and Y 2 each are independently an oxygen atom, a sulfur atom, or —NR 7 —, wherein R 7 is a hydrogen atom or a monovalent organic group; Z 1 is a divalent organic group having an aliphatic structure and 1 to 15 carbon atoms, at least one substituent for Y 1 and Y 2 and Z 1 may be bonded to form a ring structure, and substi

Assignees

• Jsr Corp

Inventors

• Murakami Takuya
• Yasuike Nobuo
• Suhara Ryou

Classifications

• C08G73/1042

  Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds · CPC title

• G02F1/133723

  Polyimide, polyamide-imide · CPC title

• G02F1/133711

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

• C09K19/542

  Macromolecular compounds · CPC title

• C09K19/56 Primary

  Aligning agents · CPC title