Cinnamic acid derivative, polymer thereof, and liquid crystal alignment layer comprising cured product thereof

Patent metadata

Field	Value
Publication number	US-10095066-B2
Application number	US-201615168849-A
Country	US
Kind code	B2
Filing date	May 31, 2016
Priority date	Jun 30, 2011
Publication date	Oct 9, 2018
Grant date	Oct 9, 2018

Abstract

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

First claim

The invention claimed is:

1. A polymer constituted with a cured product, wherein the cured product has a structural unit represented by the general formula (V):

wherein Sp 1 and Sp 2 each represent a spacer unit, A 01 and A 02 each independently represent a group selected from the group consisting of:
(a) a trans-1,4-cyclohexylene group wherein 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 wherein 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,
X 1 , X 2 , Y 1 and Y 2 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 CH 2 group or two or more non-adjacent CH 2 groups may be substituted with —O—, —CO—O—, —O—CO—, —CH═CH—or a combination thereof,
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
R 1 R 2 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 30 carbon atoms, wherein one —CH 2 —group or two or more non-adjacent —CH 2 — groups in R 1 and R 2 may be substituted with —O—, —CO—, —CO—O—, —O—CO—, —CO—NH—, —NH—CO—, —NCH 3 —, —CH═CH—, —CF═CF—, —C≡C—, or a combination thereof, wherein one or two or more —CH 2 — groups in R 1 and R 2 may be each independently substituted with a cycloalkyl group with a 3- to 8-membered ring, and a hydrogen atom in R 1 and R 2 may be substituted with an alkyl group having 1 to 20 carbon atoms, a cyano group, or a halogen atom,
W represents —O— or —NR 3 —, in which R 3 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, M b and M d 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 M b and M d are arranged may be the same as or different from that shown in the formula, and the monomer units of M b and M d may be each independently constituted with one or two or more different units.

2. The polymer according to claim 1 , wherein M b 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 Sp 1 , 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.

3. The polymer according to claim 1 , wherein M d 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.

4. The polymer according to claim 3 , wherein in the general formulae (QIII-1) to (QIII-17), the monovalent organic group is represented by the general formula (QIV):
—S a —V a   (QIV)

wherein the dashed line represents a bond to an M d , S a represents a structure represented by the general formula (IV),

wherein in Sp 1 , the left dashed line represents a bond to L and the right dashed line represents a bond to A 01 , and in Sp 2 , the left dashed line represents a bond to W and the right dashed line represents a bond to A 02 ,
in Sp 1 and Sp 2 , independently,
Z 1 , Z 2 and Z 3 each independently represent a single bond, —(CH 2 ) u in which u represents 1 to 20, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CH═CH—, —CF═CF—, —CF 2 O—, —OCF 2 —, —CF 2 CF 2 —, or —C≡C—, and one or more of the non-adjacent CH 2 groups in these groups may be independently substituted with —O—, —CO—, —CO—O—, —O—CO—, —Si(CH 3 ) 2 —O—Si(CH 3 ) 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
A 1 and A 2 each independently represent a group selected from the group consisting of:
(a) a trans-1,4-cyclohexylene group, in which 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 in which 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, and
V a represents a structure represented by the following general formula (VI):

wherein the dashed line represents a bond to S a ,
Z 4 , Z 5 , Z 6 and Z 7 each independently represent a single bond, —(CH 2 ) u — in which u represents 1 to 20, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CH═CH—, —CF═CF—, —CF 2 O—, —OCF 2 —, —CF 2 CF 2 —, or —C≡C—, but one or more of the non-adjacent CH 2 groups in these substituents may be independently substituted with

Assignees

• Dainippon Ink & Chemicals

Inventors

• Schadt Martin
• Nose Sayaka
• Nagashima Yutaka
• Nishiyama Isa
• Takatsu Haruyoshi

Classifications

• C07C2601/08

  the ring being saturated · CPC title

• C07C2601/02

  with a three-membered ring · CPC title

• C08F122/40

  Imides, e.g. cyclic imides · CPC title

• C07C69/734 Primary

  Ethers · CPC title

• C09K19/56

  Aligning agents · CPC title