Polymerizable compounds, compositions, polymers, optically anisotropic articles, liquid crystal display devices and organic EL devices

Patent metadata

Field	Value
Publication number	US-10351643-B2
Application number	US-201415100108-A
Country	US
Kind code	B2
Filing date	Nov 27, 2014
Priority date	Nov 29, 2013
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

An object of the invention is to provide polymerizable compounds having excellent optical characteristics and suited as materials for optically anisotropic articles, compositions containing the polymerizable compounds, polymers obtained by polymerizing the polymerizable compounds, optically anisotropic articles formed of the polymers, and liquid crystal display devices including the optically anisotropic articles.

First claim

The invention claimed is:

1. A polymerizable compound represented by the general formula selected from the group consisting of (1-1), (1-2) and (1-3):

wherein in the formulae (1-1), (1-2) and (1-3), P is a polymerizable functional group, Sp is a spacer group or a single bond,
A 1 , A 2 , A 3 and A 4 each independently represent a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group,
X 1 , X 2 , X 3 and X 4 each independently represent a divalent bonding group or a single bond,
R 1 is an alkyl or alkoxy group having 1 to 12 carbon atoms, or “*-Sp-P” in which * indicates A 4 or A 3 ,
m and n are each independently an integer of 0 to 4 wherein m+n is an integer of 2 or greater,
T 1 and T 2 each independently represent —S—, —O—, —NR 2 —, —CH 2 —, —NH—, —C(═O)—, —S(═O)— or —C(═S)—,
R 2 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a nitro group or a hydroxyl group,
R 3 and R 4 each independently represent a monovalent substituent or form a ring through Y which connects R 3 and R 4 together wherein when such a ring is formed, R 3 and R 4 each independently represent a group selected from the group consisting of —O—, —S—, —SO—, —SO 2 —, —NR— wherein R is a hydrogen atom or a monovalent substituent, ═N—, ═N(+)R— wherein R of ═N(+)R— is a hydrogen atom or a monovalent substituent, —C(═O)—, —C(═S)— and ═CR— wherein R of ═CR— is a hydrogen atom or a monovalent substituent, and
Y represents 2 to 4 atoms selected from the group consisting of carbon atoms and Group XIV to Group XVI nonmetallic atoms, and in combination with R 3 —C—R 4 in the formula forms a 5- to 7-membered ring which may be substituted with a monovalent substituent in place of any hydrogen atom bonded to the 5- to 7-membered ring, except when T 1 and R 3 , and T 2 and R 4 are each the same as each other and when T 1 and R 4 , and T 2 and R 3 are each the same as each other.

2. The polymerizable compound according to claim 1 , wherein R 3 and R 4 are each independently a monovalent substituent and at least one of R 3 and R 4 is a cyano group.

3. The polymerizable compound according to claim 1 , wherein R 3 and R 4 are each independently a monovalent substituent and R 3 or R 4 is an alkyl carboxylate having an alkyl group with 1 to 3 carbon atoms.

4. The polymerizable compound according to claim 1 , wherein the ring formed by R 3 —C—R 4 and Y is any selected from the group consisting of rings represented by the following general formulae (Y-1) to (Y-24):

in the formulae, R is a hydrogen atom or a monovalent substituent, j is an integer of 0 to 4, and the bonds ═C intersected with a wiggly line are to the 5-membered ring including T 1 and T 2 in the general formula (1-0).

5. The polymerizable compound according to claim 1 , wherein X 1 , X 2 , X 3 and X 4 each independently represent a single bond, —CH 2 CH 2 —, —CH═CH—, —CH═CHCOO—, —OCO—CH═CH—, —(CH 2 ) u O—COO—, —(CH 2 ) u —OCO—, —(CH 2 ) u —COO—, —(CH 2 ) u —O—, —O—COO—(CH 2 ) u —, —OCO—(CH 2 ) u —, —COO—(CH 2 ) u — or —O—(CH 2 ) u — wherein u is an integer of 0 to 2.

6. A composition comprising the polymerizable compound described in claim 1 .

7. A polymer obtained by polymerizing the composition described in claim 6 .

8. An optically anisotropic article comprising the polymer described in claim 7 .

9. A liquid crystal display device comprising the optically anisotropic article described in claim 8 .

10. An organic EL device comprising the optically anisotropic article described in claim 8 .

Assignees

• Dainippon Ink & Chemicals

Inventors

• Hasebe Hiroshi
• Aoki Yoshio
• Kotani Kunihiko
• Koiso Akihiro
• Nakata Hidetoshi

Classifications

• G02B5/3016

  involving passive liquid crystal elements (optical properties of liquid crystals G02F1/0063; polarising elements associated with active liquid crystal devices G02F1/133528) · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C09K19/3861

  containing condensed ring systems · CPC title

• G02F1/13363

  Birefringent elements, e.g. for optical compensation · CPC title

• C09K19/34

  containing at least one heterocyclic ring · CPC title