Compound, polymer, liquid crystal alignment layer, liquid crystal display device, and optically anisotropic material

Patent metadata

Field	Value
Publication number	US-9683174-B2
Application number	US-201415039727-A
Country	US
Kind code	B2
Filing date	Nov 27, 2014
Priority date	Nov 29, 2013
Publication date	Jun 20, 2017
Grant date	Jun 20, 2017

Abstract

[Object]
To provide a liquid crystal alignment layer that can easily be formed, to which an anchoring force can be efficiently induced with less polarized light for exposure, and that is effective in controlling the orientation and pretilt angle of liquid crystal molecules, and a compound and polymer that can be used for such a liquid crystal alignment layer.
[Solution]
A compound is represented by general formula (I):

where
L is a polymerizable group; Sp is a spacer unit containing methylene; Q is a direct bond, —O—, or other group; A contains a group selected from the group consisting of trans-1,4-cyclohexylene and other groups; s is an integer of 1 to 4, where if s is 2 to 4, each A may be the same or different; X and Y are each independently hydrogen or other group; and M is any of general formulas (IIa), (IIb), and (IIc):

First claim

The invention claimed is:

1. A compound represented by general formula (I):

wherein
L is a polymerizable group;
Sp is a spacer unit comprising methylene;
Q is a direct bond, —O—,—CO—O—, or —O—CO—;
A comprises a group selected from the group consisting of trans-1,4-cyclohexylene (wherein one or more non-adjacent methylene groups present in this group are optionally replaced with —O—, —NH—, or —S—), 1,4-phenylene (wherein one or more —CH═groups present in this group are optionally replaced with—N═), 1,4-cyclohexenylene, 2,5-thiophenylene, 2,5-furanylene, 1,4-bicyclo[2,2,2]octylene, naphdialene-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, and 1,2,3,4-tetrahydronaphthalene-2,6-diyi, wherein the groups are unsubstituted, or one or more hydrogen atoms present therein are optionally replaced with fluorine, chlorine, cyano, methyl, or methoxy;
s is an integer of 1 to 4, wherein ifs is 2 to 4, each A may be the same or different;
X and Y are each independently hydrogen, fluorine, chlorine, cyano, or an alkyl group of 1 to 20 carbon atoms, wherein any hydrogen atom present in the alkyl group is optionally replaced with fluorine, and if one or more non-adjacent methylene groups are present in the alkyl group, the one or more non-adjacent methylene groups are optionally replaced with —O—, —CO—O—, —O—CO—, and/or —CH═CH—, and
M is any of general. formulas (IIa), (IIb), and (IIc):

wherein
the dashed line is a linkage to the carbon atom;
R 1 is an alkylene group of 1 to 30 carbon atoms, wherein each R 1 , if present, may be the same or different;
R 2 is hydrogen or an alkyl group of 1 to 30 carbon atoms; and
if one or more non-adjacent methylene groups are present in R I and .R 2 , the one or more non-adjacent methylene groups are optionally replaced with —O—, —CO—, —CO—O—, —CO—, —CO—NH—, —NH—CO—, —NCH 3 —, —CH═CH—, —CF═CF—, and/or —C═C—, and any hydrogen atom present in R 1 and R 2 is optionally replaced with an alkyl group of 1 to 20 carbon atoms, cyano, or halogen.

2. The compound according to claim 1 , wherein R 1 in general formulas (IIa), (IIb), and (IIc) is represented by general formula (IId):

wherein
the dashed line is a linkage to the oxygen or nitrogen atom, and * is a linkage to the cyano group;
W 1 is methylene (wherein any hydrogen atom present in this group is optionally replaced with an alkyl group of 1 to 5 carbon atoms), —CO—O—, or —CO—NH—;
R 4 is an alkylene group of 1 to 20 carbon atoms, wherein if one or more non-adjacent methylene groups are present in the alkylene group, the one or more non-adjacent methylene groups are optionally replaced with —O—, —CO—, —CO—O—, —O—CO—, —CO—NH—, —NH—CO—, or —NCH 3 —; and
R 5 is hydrogen or an alkyl group of 1 to 5 carbon atoms, wherein any hydrogen atom present in the alkyl group is optionally replaced with fluorine or chlorine.

3. The compound according to claim 1 , wherein A in general formula (I) is 1,4-phenyiene wherein one or more hydrogen atoms present in the 1,4-phenylene group are optionally replaced with fluorine, chlorine, methyl, or methoxy.

4. The compound according, to claim 1 , wherein X and Y in general formula (I) are hydrogen.

5. The compound according to claim 1 wherein L in general formula (I) is any polymerizable group selected from the group consisting of polymerizable groups represented by general formulas (III-1) to (III-10):

wherein the dashed line is a linkage to Sp; R 30 is hydrogen, fluorine, chlorine, an alkyl group of 1 to 4 carbon atoms, phenyl, or phenoxy; R 31 is hydrogen, chlorine, methyl, or phenyl; and R 32 is each independently hydrogen or an alkyl group of 1 to 5 carbon atoms.

6. The compound according to claim 1 , wherein L in general formula (I) is any of polymerizable groups represented by general formulas (III-1) (III-2) and (III-6):

wherein the dashed line is a linkage to Sp; R 30 and R 31 are each independently hydrogen or methyl; and R 32 is hydrogen or an alkyl group of 1 to 5 carbon atoms.

7. The compound according to claim 1 , wherein -(A) s - in general formula (I) is represented by general formula (IVa):
- - - -A 1 -Z 1 p A 2 -Z 2 q A 3 -Z 3 r **   (IVa)

wherein
the dashed line is a linkage to Q. and ** is a linkage to the carbon atom;
A 1 , A 2 , and A 3 are each independently a group selected from the group consisting of trans-1,4-cyclohexylene (wherein one or more non-adjacent methylene groups present in this group are optionally replaced with —O—, —NH—, or —S—), ,4-phenylene (wherein one or more —CH═groups present in this group are optionally replaced with 1,4-cyclohexenylene, 2,5-thiophenylene, 2,5-aranylene, 1,4-bicyclo[2,2,2]octylene, naphthalene-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, and 1,2,3,4-tetrahydronaphthalene-2,6-diyl, wherein the groups are unsubstituted, or one or more hydrogen atoms present therein are optionally replaced with fluorine, chlorine, cyano, methyl, or methoxy;
Z 1 , Z 2 , and Z 3 are each independently a single bond, an alkylene group of 1 to 20 carbon atoms, —OCH 2 —, —CH 2 O—, —CO —O—,—O—,—CO—,—CH═CH—, —CF═CF—, -CF 2 O—, -OCF 2 —, —CF 2 CF 2 —, or —C≡C— wherein if one or more non-adjacent methylene groups are present in these substituents, the one or more non-adjacent methylene groups are each independently optionally replaced with —O—, —CO—, —CO —O—, —O—CO—, —Si(CH 3 ) 2 —O—Si(CH 3 ) 2 —, —NR 6 —, —NR 6 —CO—, —CO—NR 6 , —NR 6 —CO—O—, —O—CO—NR 6 —, —NR 6 —CO—NR 6 —, —CH═CH—, —C═C—, or —O—CO—O—, wherein R 6 is each independently hydrogen or an alkyl group of 1 to 5 carbon atoms; and
p, q, and r are each an integer of 0 to 4, wherein p+q+r=s.

8. The compound according to claim 7 , wherein, in general formula (IVa),
A 2 is any of trans-1 ,4-cyclohexylene, 2,6-naphthylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, and 1,4-phenylene, wherein one or more hydrogen atoms present in the groups are optionally replaced with fluorine, chlorine, methyl, or methoxy;
Z 2 is any of a single bond, an alkylene group of 1 to 20 carbon atoms, —OCH 2 ,—, —CH 2 O—, —CO—O—, —O—CO—, —CH═CH—, and —C≡—, wherein if one or more non-adjacent methylene groups are present in the groups, the one or more non-adjacent methylene groups are each independently optionally replaced with —O—, —CO—, —CO—O—, —O—CO—, —CH═CH—, or —C≡C—; and
q is 1.

9. The compound according to claim 7 , wherein A 2 in general formula (IVa) is 1,4-phenylene, wherein one or more hydrogen atoms present in the 1,4-phenylene group are optionally replaced with fluorine, chlorine, methyl, or methoxy.

10. A polymer obtained by polymerization of a composition comprising the compound according to claim 1 , the polymer comprising structural units represented by general formula (PI):

wherein La is a group derived from L, and Sp, Q, A, X. Y M, and s are as defined in general formula (I).

11. A liquid crystal alignment layer for use in a vertically aligned liquid crystal display device, the liquid crystal alignment layer comprising a cured product of the polymer according to claim 1

Assignees

• Dainippon Ink & Chemicals

Inventors

• Hasebe Hiroshi
• Maruyama Kazunori
• Kodera Fumiaki
• Kotani Kunihiko
• Nose Sayaka
• Aoki Yoshio
• Kusumoto Tetsuo

Classifications

• C09K19/062

  containing one non-condensed benzene ring · CPC title

• C08F22/10

  Esters · CPC title

• G02F1/133788

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

• C07C255/16

  containing cyano groups and singly-bound oxygen atoms bound to the same carbon atom of an acyclic carbon skeleton · CPC title

• C09K19/56 Primary

  Aligning agents · CPC title