IP Library Granted Patent US 10,351,643
Granted Patent B2
US 10,351,643 · App. 15/100,108 · Granted Jul 16, 2019

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

Inventors: Hiroshi Hasebe (Kita-adachi-gun, JP); Yoshio Aoki (Kita-adachi-gun, JP); Kunihiko Kotani (Kita-adachi-gun, JP); Akihiro Koiso (Kita-adachi-gun, JP); Hidetoshi Nakata (Kita-adachi-gun, JP)
Assignee: DIC CORPORATION
C08F122/24C07D339/06C07D409/04C07D413/04C07D417/04C07D471/04C08F222/10C09K19/02C09K19/32C09K19/34C09K19/3483C09K19/3486C09K19/3491C09K19/3497C09K19/38C09K19/3861G02B5/3016H01L51/004C08F2222/1013C09K2019/0448G02F1/13363G02F2001/133633H01L51/0074H01L51/5281
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Quick Facts
Patent No.
US 10,351,643
App. No.
15/100,108
Granted
Jul 16, 2019
Kind
B2
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.

Claims (20)

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 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2024
From: DIC CORPORATION
To: SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIAL CO., LTD.
Reel/Frame 067528/0688 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 27, 2016
From: HASEBE, HIROSHI; AOKI, YOSHIO; KOTANI, KUNIHIKO; KOISO, AKIHIRO; NAKATA, HIDETOSHI
To: DIC CORPORATION
Reel/Frame 038739/0192 →
Priority Claims (1)
JP 2013-248382 · Nov 29, 2013 · national
Continuity (1)
Related Publication 20170037159A1 · Feb 9, 2017