# US 2014/0154428 A1 · Cinnamic acid derivative, polymer thereof, and liquid crystal alignment layer comprising cured product thereof

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2014/0154428 A1
- Document ID: US20140154428A1
- Status: Published application
- Kind: A1
- Application number: 14/129,848
- Filed: 2012-06-26
- Published: 2014-06-05
- Earliest claimed: 2011-06-30
- Assignees: DIC Corporation
- Inventors: Martin Schadt; Sayaka Nose; Yutaka Nagashima; Isa Nishiyama; Haruyoshi Takatsu
- Web page: https://patentgrep.com/patent/US20140154428A1

## CPC

- G02F 1/133711: {by organic films, e.g. polymeric films}
- C07C 69/734: Ethers
- C07D 207/452: with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
- C08F 22/40: Imides, e.g. cyclic imides
- C08F 122/20: Esters containing oxygen in addition to the carboxy oxygen
- C08F 122/40: Imides, e.g. cyclic imides
- C09K 19/56: Aligning agents
- C07C 2601/02: with a three-membered ring
- C07C 2601/08: the ring being saturated
- C07C 2601/14: The ring being saturated
- C09K 2019/0448: {the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate}
- C09K 2323/02: Alignment layer characterised by chemical composition
- G02F 1/133738: {for homogeneous alignment}
- G02F 1/133742: {for homeotropic alignment}
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Provided is a liquid crystal alignment layer of which a constituent member is a compound represented by the general formula (I).

## Claims

### Claim 1

A compound represented by the general formula (I):
(wherein L represents a polymerizable group and Sp1 and Sp2 each represent a spacer unit,
A01 and A02 each independently represent a group selected from the group consisting of:
(a) a trans-1,4-cyclohexylene group (one methylene group or two or more non-adjacent methylene groups present in this group may be substituted with —O—, —NH—, or —S—),
(b) a 1,4-phenylene group (one or two or more —CH═'s present in this group may be substituted with —N═), and
(c) a 1,4-cyclohexenylene group, a 2,5-thiophenylene group, a 2,5-furanylene group, a 1,4-bicyclo(2.2.2)octylene group, a naphthalene-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, and a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, in which the group (a), (b), or (c) may be each unsubstituted or may have one or more hydrogen atoms substituted with a fluorine atom, a chlorine atom, a cyano group, a methyl group, or a methoxy group,
X1, X2, Y1 and Y2 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or an alkyl group having 1 to 20 carbon atoms, but a hydrogen atom in the alkyl group may be substituted with a fluorine atom, and one CH2 group or two or more non-adjacent CH2 groups may be substituted with —O—, —CO—O—, —O—CO— and/or —CH═CH—,
Z is represented by the general formula (IIa) or (IIb):
(in which the dashed line represents a bond to a carbon atom, to which Z is bonded, and
R1 and R2 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 30 carbon atoms, one —CH2— group or two or more non-adjacent —CH2— groups in R1 and R2 may be substituted with —O—, —CO—, —CO—O—, —O—CO—, —CO—NH—, —NH—CO—, —NCH3—, —CH═CH—, —CF═CF—, and/or —C≡C—, one or two or more —CH2— groups in R1 and R2 may be each independently substituted with a cycloalkyl group with a 3- to 8-membered ring, and a hydrogen atom in R1 and R2 may be substituted with an alkyl group having 1 to 20 carbon atoms, a cyano group, or a halogen atom),
W represents —O— or —NR3—, in which R3 represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or a cycloalkyl group with a 3- to 8-membered ring, which may have the alkyl group interposed therein as a linking group, a hydrogen atom in the alkyl group may be unsubstituted or may be substituted with a fluorine atom or a chlorine atom, a hydrogen atom in the cycloalkyl group may be unsubstituted or may be substituted with an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine atom, or a chlorine atom, and
r and t each independently represent 1 or 2).

### Claim 2 (depends on 1)

The compound according to claim 1, wherein in the general formula (I), L represents any substituent selected from the group consisting of the general formulae (III-1) to (III-17):
(wherein the dashed line represents a bond to Sp1 and R's independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms).

### Claim 3 (depends on 1)

The compound according to claim 1, wherein in the general formula (I), Sp1 and Sp2 are each independently a structure represented by the following general formula (IV):
[Chem. 4]
—Z1A1-Z2pA2-Z3q— (IV)
(wherein which in Sp1, the left dashed line represents a bond to L and the right dashed line represents a bond to A01, and in Sp2, the left dashed line represents a bond to W and the right dashed line represents a bond to A02,
in Sp1 and Sp2, independently,
Z1, Z2 and Z3 each independently represent a single bond, —(CH2)u— (in which u represents 1 to 20), —OCH2—, —CH2O—, —COO—, —OCO—, —CH═CH—, —CF═CF—, —CF2O—, —OCF2—, —CF2CF2—, or —C≡C—, and one or more of the non-adjacent CH2 groups in these groups may be independently substituted with —O—, —CO—, —CO—O—, —O—CO—, —Si(CH3)2—O—Si(CH3)2—, —NR—, —NR—CO—, —CO—NR—, —NR—CO—O—, —O—CO—NR—, —NR—CO—NR—, —CH═CH—, —C≡C—, or —O—CO—O— (in which R's independently represent hydrogen or an alkyl group having 1 to 5 carbon atoms), and
A1 and A2 each independently represent a group selected from the group consisting of:
(a) a trans-1,4-cyclohexylene group (one methylene group or two or more non-adjacent methylene groups present in this group may be substituted with —O—, —NH—, or —S—),
(b) a 1,4-phenylene group (one or two or more —CH═'s present in this group may be substituted with —N═), and
(c) a 1,4-cyclohexenylene group, a 2,5-thiophenylene group, a 2,5-furanylene group, a 1,4-bicyclo(2.2.2)octylene group, a naphthalene-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, and a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, in which the group (a), (b), or (c) may be each unsubstituted or may have one or more hydrogen atoms substituted with a fluorine atom, a chlorine atom, a cyano group, a methyl group, or a methoxy group, and
p represents 0 or 1, and q represents 0, 1, or 2).

### Claim 4 (depends on 1)

The compound according to claim 1, wherein in the general formula (IIa) or (IIb), R1 represents a linear or branched alkyl group having 1 to 20 carbon atoms, one —CH2— group or two or more —CH2— groups in R1 may be each independently substituted with a cycloalkyl group with a 3- to 8-membered ring, and a hydrogen atom in R1 may be substituted with an alkyl group having 1 to 20 carbon atoms, a cyano group, or a halogen atom.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein in the general formula (I), X1, X2, Y1 and Y2 each represent a hydrogen atom.

### Claim 6 (depends on 2)

The compound according to claim 2, wherein L in the general formula (I) is represented by the general formula (III-1), (III-2), (III-6), (III-7), or (III-13).

### Claim 7 (depends on 1)

The compound according to claim 1, wherein Sp1 in the general formula (I) represents a linear or branched alkylene group having 1 to 20 carbon atoms, or the alkylene group having one or more CH2 groups which are not adjacent to each other substituted with —O— or —COO—.

### Claim 8 (depends on 1)

The compound according to claim 1, wherein A01 in the general formula (I) represents a 1,4-phenylene group having one or more hydrogen atoms which may be substituted with a fluorine atom, a chlorine atom, a methyl group, or a methoxy group.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein Sp2 in the general formula (I) represents a linear or branched alkylene group having 1 to 20 carbon atoms, or the alkylene group having one or more CH2 groups which are not adjacent to each other substituted with —O— or —COO—.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein A02 in the general formula (I) represents a 1,4-phenylene group having one or more hydrogen atoms which may be substituted with a fluorine atom, a chlorine atom, a methyl group, or a methoxy group.

### Claim 11 (depends on 2)

The compound according to claim 2, wherein L in the general formula (I) is represented by the general formula (III-1) or (III-2).

### Claim 12 (depends on 1)

A polymer constituted with a cured product of a composition containing the compound according to claim 1, wherein the cured product has a structural unit represented by the general formula (V):
(wherein which Sp1, Sp2, A01, A02, X1, X2, Y1, Y2, W, Z, r, and t have the same definitions as in the general formula (I), Mb and Md each represent a monomer unit of the polymer, y and w each represent a molar fraction of the copolymer, each satisfying 0<y≦1 and 0≦w<1, n represents 4 to 100,000, the order in which Mb and Md are arranged may be the same as or different from that shown in the formula, and the monomer units of Mb and Md may be each independently constituted with one or two or more different units).

### Claim 13 (depends on 12)

The polymer according to claim 12, wherein Mb in the general formula (V) represents any one or more selected from the group consisting of the general formulae (QIII-A-1) to (QIII-A-17):
(wherein the dashed line represents a bond to Sp1, R's independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and any hydrogen atom in each of the structures may be substituted with a fluorine atom, a chlorine atom, a methyl group, or a methoxy group).

### Claim 14 (depends on 12)

The polymer according to claim 12, wherein Md in the general formula (V) represents any one or more selected from the group consisting of the general formulae (QIII-1) to (QIII-17):
(wherein the dashed line represents a bond to a hydrogen atom or a monovalent organic group, R's independently represent hydrogen or an alkyl group having 1 to 5 carbon atoms, and any hydrogen atom in each of the structures may be substituted with a fluorine atom, a chlorine atom, a methyl group, or a methoxy group).

### Claim 15 (depends on 12)

The polymer according to claim 12, wherein in the general formulae (QIII-1) to (QIII-17), the monovalent organic group is represented by the general formula (QIV):
[Chem. 8]
—Sa—Va (QIV)
(wherein the dashed line represents a bond to an Md, Sa represents a structure represented by the general formula (IV), and Va represents a structure represented by the following general formula (VI):
[Chem. 9]
—A3-Z4r1A4-Z5s1A5-Z6t1A6-Z7u1R12 (VI)
(wherein the dashed line represents a bond to Sa,
Z4, Z5, Z6 and Z7 each independently represent a single bond, —(CH2)u— (in which u represents 1 to 20), —OCH2—, —CH2O—, —COO—, —OCO—, —CH═CH—, —CF═CF—, —CF2O—, —OCF2—, —CF2CF2—, or but one or more of the non-adjacent CH2 groups in these substituents may be independently substituted with —O—, —CO—, —CO—O—, —O—CO—, —Si(CH3)2—O—Si(CH3)2—, —NR—, —NR—CO—, —CO—NR—, —NR—CO—O—, —O—CO—NR—, —NR—CO—NR—, —CH═CH—, or —O—CO—O— (in which R's independently represent hydrogen or an alkyl group having 1 to 5 carbon atoms),
A3, A4, A5 and A6 each independently represent a group selected from the group consisting of:
(a) a trans-1,4-cyclohexylene group (one methylene group or two or more non-adjacent methylene groups present in this group may be substituted with —O—, —NH—, or —S—),
(b) a 1,4-phenylene group (one or two or more —CH═'s present in this group may be substituted with —N═), and
(c) a 1,4-cyclohexenylene group, a 2,5-thiophenylene group, a 2,5-furanylene group, a 1,4-bicyclo(2.2.2)octylene group, a naphthalene-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, and a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, in which the group (a), (b), or (c) may be each unsubstituted or may have one or more hydrogen atoms substituted with a fluorine atom, a chlorine atom, a cyano group, a methyl group, or a methoxy group,
r1, s1, t1, and u1 each independently represent 0 or 1, and
R12 represents hydrogen, fluorine, chlorine, a cyano group, or an alkyl group having 1 to 20 carbon atoms, a hydrogen atom in the alkyl group may be substituted with a fluorine atom, and one CH2 group or two or more non-adjacent CH2 groups may be substituted with —O—, —CO—O—, —O—CO— and/or —CH═CH—)).

### Claim 16 (depends on 11)

A liquid crystal alignment layer for a vertical alignment mode liquid crystal display element, using the polymer according to claim 11.

### Claim 17 (depends on 16)

A vertical alignment mode liquid crystal display element using the liquid crystal alignment layer according to claim 16.

### Claim 18 (depends on 11)

A liquid crystal alignment layer for a horizontal alignment mode liquid crystal display element, using the polymer according to claim 11.

### Claim 19 (depends on 18)

A horizontal alignment mode liquid crystal display element using the liquid crystal alignment layer according to claim 18.

### Claim 20 (depends on 11)

A liquid crystal alignment layer for an optical anisotropic body, using the polymer according to claim 11.

### Claim 21 (depends on 20)

An optical anisotropic body constituted with a polymer of a polymerizable liquid crystal composition, wherein polymerizable liquid crystal molecules in the polymerizable liquid crystal composition are aligned using the liquid crystal alignment layer according to claim 20.