Polymerizable liquid crystal compound, polymerizable composition, polymer, retardation film, method for producing retardation film, transfer laminate, optical member, method for producing optical member, and display device

Patent metadata

Field	Value
Publication number	US-11560518-B2
Application number	US-201816754870-A
Country	US
Kind code	B2
Filing date	Oct 10, 2018
Priority date	Oct 13, 2017
Publication date	Jan 24, 2023
Grant date	Jan 24, 2023

Abstract

A polymerizable liquid crystal compound represented by the following general formula (1):(the symbols in the general formula (1) are as described in the DESCRIPTION.)

First claim

The invention claimed is:

1. A polymerizable liquid crystal compound represented by the following general formula (1):
General Formula (1)

where:
L 1 , L 2 , L 3 and L 4 each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C— or a single bond;
A 1 and A 2 each independently represent a divalent alicyclic hydrocarbon group containing 3 to 20 carbon atoms and optionally being unsubstituted or substituted by at least one substituent group E, and any carbon atom of the alicyclic hydrocarbon group is optionally replaced by a heteroatom;
A 3 and A 4 each independently represent a divalent alicyclic or aromatic hydrocarbon group containing 3 to 20 carbon atoms and optionally being unsubstituted or substituted by at least one substituent group E, and any carbon atom of the alicyclic or aromatic hydrocarbon group is optionally replaced by a heteroatom;
R and R 2 each independently represent a group selected from the following general formula (R-1):
-L 5 -R sp1 —Z 1 where:  General formula (R-1):

L 5 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C— or a single bond;
R sp1 represents a single bond or an alkylene group containing 1 to 20 carbon atoms, in which one —CH 2 — or two or more non-adjacent —CH 2 — are each independently optionally replaced by —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH— or —C≡C—; and
Z 1 represents a polymerizable functional group selected from the following formulae (Z-1) to (Z-8):

where R z is each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group or a trifluoromethyl group;
D 1 and D 2 each independently represent a group selected from the following general formula (D-1):

where:
G 1 represents a hydrogen atom or an alkyl group containing 1 to 6 carbon atoms, and the alkyl group is optionally unsubstituted or substituted by at least one substituent group E;
Q 1 represents an organic group containing 2 to 30 carbon atoms and containing an aromatic hydrocarbon group; any carbon atom of the aromatic hydrocarbon group is optionally replaced by a heteroatom; and the aromatic hydrocarbon group is optionally unsubstituted or substituted by at least one substituent group E;
J 1 represents —O—, —S—, —COO—, —OCO—, —OCO—O—, —NQ 2 -, —N═CQ 2 -, —CO—NQ 2 -, —OCO—NQ 2 - or —O—NQ 2 -;
Q 2 represents a hydrogen atom, an alkyl group containing 1 to 20 carbon atoms, a cycloalkyl group containing 3 to 12 carbon atoms, a cycloalkenyl group containing 3 to 12 carbon atoms, an organic group containing 2 to 30 carbon atoms and containing an aromatic hydrocarbon group (any carbon atom of the aromatic hydrocarbon group is optionally replaced by a heteroatom) or -(L 6 -A 5 ) q -L 7 -R sp2 —Z 2 ; the alkyl group, the cycloalkyl group, the cycloalkenyl group and the aromatic hydrocarbon group are each optionally unsubstituted or substituted by at least one substituent group E; the alkyl group is optionally substituted by the cycloalkyl group or the cycloalkenyl group; one —CH 2 — or two or more non-adjacent —CH 2 — in the alkyl group are each independently optionally replaced by —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —SO 2 —, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF— or —C≡C—; one —CH 2 — or two or more non-adjacent —CH 2 — in the cycloalkyl or cycloalkenyl group are each independently optionally replaced by —O—, —CO—, —COO—, —OCO— or —O—CO—O—; where:
L 6 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C— or a single bond;
A 5 represents a divalent alicyclic or aromatic hydrocarbon group containing 3 to 20 carbon atoms and optionally being unsubstituted or substituted by at least one substituent group E, and any carbon atom of the alicyclic or aromatic hydrocarbon group is optionally replaced by a heteroatom;
L 7 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C— or a single bond;
R sp2 represents a single bond or an alkylene group containing 1 to 20 carbon atoms, in which one —CH 2 — or two or more non-adjacent —CH 2 — are each independently optionally replaced by —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH— or —C≡C—;
Z 2 represents a polymerizable functional group selected from the following formulae (Z-1) to (Z-8):

where R z is each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group or a trifluoromethyl group;
q is an integer of 0 to 4;
when plural L 6 s, as well as plural A 5 s, are present, they are optionally the same or different from each other; and
Q 1 and Q 2 are optionally bound to each other to form a ring
the substituent groups E, E 1 and E 2 each independently represent a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl 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 a linear or branched alkyl group containing 1 to 20 carbon atoms, in which one —CH 2 — or two or more non-adjacent —CH 2 — are each independently optionally replaced by —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— or —C≡C—, and any hydrogen atom in the alkyl group is optionally replaced by a fluorine atom: or the substituent groups E, E 1 and E 2 each independently represent a group represented by -L E -R spE —Z E ,

where:
L E represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—,

Assignees

• Dainippon Printing Co Ltd

Inventors

• Motooka Mami
• Okuyama Ken-Ichi
• Okada Kazuyuki
• Takahashi Terutaka
• Endo Mitsuru
• Irie Shunsuke
• Sakaguchi Tsuyoshi
• Akiyama Kei
• Ishikawa Kohei

Classifications

• C07D263/58 Primary

  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

• C07D417/14

  containing three or more hetero rings · CPC title

• G02B5/3083

  Birefringent or phase retarding elements (G02B5/3008, G02B5/3016 take precedence; systems for polarisation control G02B27/286; manufacturing phase modulating patterns by lithographic processes G03F7/001) · CPC title

• C08F22/24

  Esters containing sulfur · CPC title

• C07D519/00

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title