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

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

• General Formula (1)
• where:
• L1, L2, L3 and L4 each independently represent —O—, —S—, —OCH2—, —CH2O—, —CH2CH2—, —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—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH2CH2—, —OCO—CH2CH2—, —CH2CH2—COO—, —CH2CH2—OCO—, —COO—CH2—, —OCO—CH2—, —CH2—COO—, —CH2—OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C— or a single bond;
• A1 and A2 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;
• A3 and A4 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 R2 each independently represent a group selected from the following general formula (R-1):
• -L5-Rsp1—Z1 where:
• General formula (R-1):
• L5 represents —O—, —S—, —OCH2—, —CH2O—, —CH2CH2—, —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—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH2CH2—, —OCO—CH2CH2—, —CH2CH2—COO—, —CH2CH2—OCO—, —COO—CH2—, —OCO—CH2—, —CH2—COO—, —CH2—OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C— or a single bond;
• Rsp1 represents a single bond or an alkylene group containing 1 to 20 carbon atoms, in which one —CH2— or two or more non-adjacent —CH2— are each independently optionally replaced by —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH— or —C≡C—;
• and
• Z1 represents a polymerizable functional group selected from the following formulae (Z-1) to (Z-8):
• where Rz 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;
• D1 and D2 each independently represent a group selected from the following general formula (D-1):
• where:
• G1 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;
• Q1 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;
• J1 represents —O—, —S—, —COO—, —OCO—, —OCO—O—, —NQ2-, —N═CQ2-, —CO—NQ2-, —OCO—NQ2- or —O—NQ2-;
• Q2 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 -(L6-A5)q-L7-Rsp2—Z2;
• 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 —CH2— or two or more non-adjacent —CH2— in the alkyl group are each independently optionally replaced by —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —SO2—, —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 —CH2— or two or more non-adjacent —CH2— in the cycloalkyl or cycloalkenyl group are each independently optionally replaced by —O—, —CO—, —COO—, —OCO— or —O—CO—O—;
• where:
• L6 represents —O—, —S—, —OCH2—, —CH2O—, —CH2CH2—, —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—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH2CH2—, —OCO—CH2CH2—, —CH2CH2—COO—, —CH2CH2—OCO—, —COO—CH2—, —OCO—CH2—, —CH2—COO—, —CH2—OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C— or a single bond;
• A5 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;
• L7 represents —O—, —S—, —OCH2—, —CH2O—, —CH2CH2—, —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—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH2CH2—, —OCO—CH2CH2—, —CH2CH2—COO—, —CH2CH2—OCO—, —COO—CH2—, —OCO—CH2—, —CH2—COO—, —CH2—OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C— or a single bond;
• Rsp2 represents a single bond or an alkylene group containing 1 to 20 carbon atoms, in which one —CH2— or two or more non-adjacent —CH2— are each independently optionally replaced by —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH— or —C≡C—;
• Z2 represents a polymerizable functional group selected from the following formulae (Z-1) to (Z-8):
• where Rz 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 L6s, as well as plural A5s, are present, they are optionally the same or different from each other;
• and
• Q1 and Q2 are optionally bound to each other to form a ring
• the substituent groups E, E1 and E2 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 —CH2— or two or more non-adjacent —CH2— 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, E1 and E2 each independently represent a group represented by -LE-RspE—ZE,
• where:
• LE represents —O—, —S—, —OCH2—, —CH2O—, —CH2CH2—, —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—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH2CH2—, —OCO—CH2CH2—, —CH2CH2—COO—, —CH2CH2—OCO—, —COO—CH2—, —OCO—CH2—, —CH2—COO—, —CH2—OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C— or a single bond;
• RspE represents a single bond or an alkylene group containing 1 to 20 carbon atoms, in which one —CH2— or two or more non-adjacent —CH2— are each independently optionally replaced by —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH— or —C≡C—;
• and
• ZE represents a polymerizable functional group selected from the following formulae (Z-1) to (Z-8):
• where Rz 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:
• when plural substituent groups Es, as well as plural substituent groups E1s and plural substituent groups E2s, are present in the compound, they are optionally the same or different from each other;
• when plural L3s, as well as plural L4s, plural A3s and plural A4s, are present, they are optionally the same or different from each other;
• m1 and m2 each independently represent an integer of 1 to 4;
• and
• n1 and n2 each independently represent an integer of from 0 to 3.