IP Library Granted Patent US 10,633,353
Granted Patent B2
US 10,633,353 · App. 15/532,224 · Granted Apr 28, 2020

Polymerizable compound, composition, polymer, optically anisotropic body, liquid crystal display element, and organic EL display

Inventors: Sayaka Nose (Kita-adachi-gun, JP); Yuji Ohashi (Kita-adachi-gun, JP); Junichi Mamiya (Kita-adachi-gun, JP); Akihiro Koiso (Kita-adachi-gun, JP); Tatsufumi Yamazaki (Kita-adachi-gun, JP)
Assignee: DIC CORPORATION
C07D277/82C07C243/22C07D209/40C07D263/58C07D277/50C07D277/84C08F122/24H01L51/0036H01L51/5293C07C2601/14C07C2603/18
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Quick Facts
Patent No.
US 10,633,353
App. No.
15/532,224
Granted
Apr 28, 2020
Kind
B2
Abstract

It is an object of the present invention to provide a polymerizable compound having a good liquid crystal property, a good alignment property, sufficient solubility in solvents, high preservation stability in a solution state, and high optical stability; a composition including the polymerizable compound; a polymer produced by polymerizing the polymerizable compound, such as a resin produced using the polymerizable compound; an optically anisotropic body including the polymer; and a liquid crystal display element and an organic EL device that include the optically anisotropic body. As a result of conducting intensive studies in order to achieve the above object, the compound represented by General Formula (I) is developed.

Claims (31)

1. A polymerizable compound represented by General Formula (1) below,

wherein P 1 and P 2 represent a polymerizable functional group represented by Formula (P-1) or (P-2),

Sp 1 and Sp 2 represent a divalent spacer group or a single bond;

A 1 and A 2 each independently represent a divalent alicyclic or aromatic hydrocarbon group having 3 to 20 carbon atoms, the divalent alicyclic or aromatic hydrocarbon group may be optionally substituted with one or more substituents, and a carbon atom included in the alicyclic or aromatic hydrocarbon group may be replaced with a hetero atom;

Z 1 , Z 2 , Z 3 , and Z 4 each independently represent a divalent linking group or a single bond in which Z 1 directly bonded to U is —CH 2 O— or —CF 2 O—, and Z 2 directly bonded to U is —CH 2 O— or —CF 2 O—;

U represents a trivalent aromatic group selected from the group consisting of Formulae (U-1), (U-2), (U-5) and (U-6), that may be optionally substituted with one or more substituents,

T represents a group selected from Formulae (T-1) and (T-2) below,

where Q 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be optionally substituted with one or more substituents;

W 1 represents an organic group having 2 to 30 carbon atoms, the organic group includes an aromatic hydrocarbon group, a carbon atom included in the aromatic hydrocarbon group may be replaced with a hetero atom, and the aromatic hydrocarbon group may be optionally substituted with one or more substituents;

Y 1 represents —(Z 5 -A 3 )q-Z 6 -Sp 3 -P 3 , Z 5 and Z 6 represent the same things as Z 1 to Z 4 , A 3 represents the same thing as A 1 and A 2 , Sp 3 represents the same thing as Sp 1 and Sp 2 , P 3 represents the same thing as P 1 and P 2 , and q represents an integer of 0 to 4; and

m and n each independently represent an integer of 2 to 4; and,

when a plurality of A 1 groups, A 2 groups, A 3 groups, Z 1 groups, Z 2 groups, and Z 5 groups are present, they may be identical to or different from one another.

2. The polymerizable compound according to claim 1 , wherein, in General Formula (1), one or both of Z 3 and Z 4 each independently represent —OCO—CH═CH—*, —OCO—CH 2 CH 2 —*, —COO—CH 2 CH 2 —*, —O—CH═CH—*, or —O—CH 2 CH 2 —* wherein the above groups are bonded to the A 1 or A 2 group on the side denoted by *.

3. The polymerizable compound according to claim 1 , wherein, in General Formula (1), all of the A 1 groups and/or all of the A 2 groups are divalent alicyclic hydrocarbon groups that may be optionally substituted with one or more substituents.

4. The polymerizable compound according to claim 1 , wherein, in General Formula (1), both of m and n are integers of 2 to 4, wherein two or more A 1 groups and/or two or more A 2 groups are each independently a divalent aromatic hydrocarbon group that may be optionally substituted with one or more substituents, and wherein the Z 1 group with which the two or more A 1 groups are connected to each other and/or the Z 2 group with which the two or more A 2 groups are connected to each other is not a single bond.

5. The polymerizable compound according to claim 1 , wherein, in General Formula (1), Sp 1 and/or Sp 2 represents a single bond.

6. The polymerizable compound according to claim 1 , wherein, in Formulae (U-1), (U-2), (U-5) and (U-6),

one or more hydrogen atoms bonded to each of the above rings may be replaced with F, Cl, CF 3 , OCF 3 , a cyano group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, or an alkenoyloxy group having 2 to 8 carbon atoms.

7. The polymerizable compound according to claim 1 , wherein, in General Formula (1), W 1 represents a group selected from General Formulae (W-1) to (W-20) below,

wherein the above groups may have a bond at any position; Q 2 represents —O—, —S—, —NR 4 — wherein R 4 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, or —CO—; —CH═ groups included in each of the above groups may be each independently replaced with —N═; —CH 2 — groups included in each of the above groups may be each independently replaced with —O—, —S—, —NR 5 — wherein R 5 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, —SO—, —SO 2 —, or —CO— in which the polymerizable compound represented by General Formula (1) does not include two oxygen atoms directly bonded to each other; and the above groups may be optionally substituted with one or more L W substituents, where L W represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms, the alkyl group may be linear or branched, a hydrogen atom included in the alkyl group may be replaced with a fluorine atom, and one —CH 2 — group included in the alkyl group or two or more —CH 2 — groups that are included in the alkyl group and not adjacent to one another may be each independently replaced with a group selected from —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, and —C≡C—.

8. A composition comprising the polymerizable compound according to claim 1 .

9. A method for producing a polymer, the method comprising:

providing the composition according to claim 8 ; and

polymerizing the composition.

10. A method for producing an optically anisotropic body, the method comprising:

providing the composition according to claim 8 ;

aligning the polymerizable compound; and

polymerizing the composition.

11. A method for producing the optically anisotropic body according to claim 10 , wherein the optically anisotropic body is then provided for producing a liquid crystal display element comprising the optically anisotropic body.

12. A method for producing the optically anisotropic body according to claim 10 , wherein the optically anisotropic body is then provided for producing an organic EL device comprising the optically anisotropic body.

13. A liquid crystal material, an organic EL material, an organic semiconductor material, and an electronic material that comprise the polymerizable compound according to claim 1 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2024
From: DIC CORPORATION
To: SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIAL CO., LTD.
Reel/Frame 067528/0688 →
CORRECTIVE ASSIGNMENT TO CORRECT THE DOCKET NUMBER PREVIOUSLY RECORDED ON REEL 042566 FRAME 0032. ASSIGNOR(S) HEREBY CONFIRMS THE ASSSIGNMENT. Recorded Jun 15, 2017
From: NOSE, SAYAKA; OHASHI, YUJI; MAMIYA, JUNICHI; KOISO, AKIHIRO; YAMAZAKI, TATSUFUMI
To: DIC CORPORATION
Reel/Frame 042856/0967 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2017
From: NOSE, SAYAKA; OHASHI, YUJI; MAMIYA, JUNICHI; KOISO, AKIHIRO; YAMAZAKI, TATSUFUMI
To: DIC CORPORATION
Reel/Frame 042566/0032 →
Priority Claims (1)
JP 2014-245866 · Dec 4, 2014 · national
Continuity (1)
Related Publication 20170260150A1 · Sep 14, 2017