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

Patent metadata

Field	Value
Publication number	US-10633353-B2
Application number	US-201515532224-A
Country	US
Kind code	B2
Filing date	Dec 1, 2015
Priority date	Dec 4, 2014
Publication date	Apr 28, 2020
Grant date	Apr 28, 2020

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.

First claim

The invention claimed is:

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 .

Assignees

• Dainippon Ink & Chemicals

Inventors

• Nose Sayaka
• Ohashi Yuji
• Mamiya Junichi
• Koiso Akihiro
• Yamazaki Tatsufumi

Classifications

• C07C251/88

  having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines · CPC title

• 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

• C07D263/58

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2 · CPC title

• C07C2602/42

  the bicyclo ring system containing seven carbon atoms · CPC title

• C08G65/18

  Oxetanes · CPC title