Polymerizable compound, polymerizable liquid crystalline composition, macromolecular compound and film

A polymerizable liquid crystalline composition containing a compound and a chiral agent, wherein the compound has a benzoxazinone ring and an aromatic ring that directly bonds to the benzoxazinone ring, and has a mesogenic core substituted by a substituent having a polymerizable functional group, wherein the compound is represented by the following formula (I):

• wherein each of R1 and R2 independently represents a hydrogen atom, a halogen, NO2, CN, NCS, a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms (here, among —CH2— that configure the alkyl group, one —CH2— or two or more non-adjacent —CH2— may be substituted by —O—, —S—, —CO—, —COO—, —OCO—, —OCOO—, —CH═CH—, —C≡C—, —CONR3—, —NR3CO— or —NR3—) or P-Sp-L-, and at least one of R1 and R2 is P-Sp-L-;
• P represents a polymerizable functional group;
• Sp represents a single bond or an alkylene group having 1 to 12 carbon atoms (here, among non-terminal —CH2— that configure the alkylene group, one non-terminal —CH2— or two or more non-adjacent non-terminal —CH2— may be substituted by —O—, —S—, —CO—, —COO—, —OCO—, —CH═CH—, —C≡C—, —CONR4—, —NR4CO— or —NR4—);
• L represents —O—, —S—, —CO—, —COO—, —OCO—, —OCOO—, —CONR5—, —NR5CO—, —NR5— or a single bond;
• when Sp is a single bond, L is also a single bond;
• each of A1 and A2 independently represents a 1,4-phenylene group;
• one or two or more hydrogen atoms in the 1,4-phenylene group may be substituted by an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, an acyloxy group having 2 to 5 carbon atoms, an acyl group having 2 to 4 carbon atoms, an amide group having 2 to 5 carbon atoms, a cyano group or a halogen atom;
• each of Z1 and Z2 independently represents —COO—, —OCO—, —CONR6—, —NR6CO—, —OCH2—, —CH2O—, —CH2S—, —SCH2—, —CH2CH2— or a single bond;
• each of X1, X2, X3, X4, X5, X6 and X7 independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, an acyloxy group having 2 to 5 carbon atoms, an acyl group having 2 to 4 carbon atoms, an amide group having 2 to 5 carbon atoms, a cyano group or a halogen atom;
• each of R3, R4, R5 and R6 independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
• each of m and n independently represents 0, 1 or 2, and m+n=1 or 2.

A macromolecular compound obtained by polymerizing a compound which has a benzoxazinone ring and an aromatic ring that directly bonds to the benzoxazinone ring, and has a mesogenic core substituted by a substituent having a polymerizable functional group, wherein the compound is represented by the following formula (I):

• wherein each of R1 and R2 independently represents a hydrogen atom, a halogen, NO, CN, NCS, a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms (here, among —CH2— that configure the alkyl group, one —CH2— or two or more non-adjacent —CH2— may be substituted by —O—, —S—, —CO—, —COO—, —OCO—, —OCOO—, —CH═CH—, —C≡C—, —CONR3—, —NR3CO— or —NR3—) or P-Sp-L-, and at least one of R1 and R2 is P-Sp-L-;
• P represents a polymerizable functional group;
• Sp represents a single bond or an alkylene group having 1 to 12 carbon atoms (here, among non-terminal —CH2— that configure the alkylene group, one non-terminal —CH2— or two or more non-adjacent non-terminal —CHz— may be substituted by —O—, —S—, —CO—, —COO—, —OCO—, —CH═CH—, —C≡C—, —CONR4—, —NR4CO— or —NR4—);
• L represents —O—, —S—, —CO—, —COO—, —OCO—, —OCOO—, —CONR5—, —NR5CO—, —NR5— or a single bond;
• when Sp is a single bond, L is also a single bond;
• each of A1 and A2 independently represents a 1,4-phenylene group;
• one or two or more hydrogen atoms in the 1,4-phenylene group may be substituted by an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, an acyloxy group having 2 to 5 carbon atoms, an acyl group having 2 to 4 carbon atoms, an amide group having 2 to 5 carbon atoms, a cyano group or a halogen atom;
• each of Z1 and Z2 independently represents —COO—, —OCO—, —CONR6—, —NR6CO—, —OCH2—, —CH2O—, —CH2S—, —SCH2—, —CH2CH2— or a single bond;
• each of X1, X2, X3, X4, X5, X6 and X7 independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, an acyloxy group having 2 to 5 carbon atoms, an acyl group having 2 to 4 carbon atoms, an amide group having 2 to 5 carbon atoms, a cyano group or a halogen atom;
• each of R3, R4, R5 and R6 independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
• each of m and n independently represents 0, 1 or 2, and m+n=1 or 2.

A film using a compound which has a benzoxazinone ring and an aromatic ring that directly bonds to the benzoxazinone ring, and has a mesogenic core substituted by a substituent having a polymerizable functional group, wherein the compound is represented by the following formula (I):

• wherein each of R1 and R2 independently represents a hydrogen atom, a halogen, NO2, CN, NCS, a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms (here, among —CH2— that configure the alkyl group, one —CH2— or two or more non-adjacent —CH2— may be substituted by —O—, —S—, —CO—, —COO—, —OCO—, —OCOO—, —CH═CH—, —C≡C—, —CONR3—, —NR3CO— or —NR3—) or P-Sp-L-, and at least one of R1 and R2 is P-Sp-L-;
• P represents a polymerizable functional group;
• Sp represents a single bond or an alkylene group having 1 to 12 carbon atoms (here, among non-terminal —CH2— that configure the alkylene group, one non-terminal —CH2— or two or more non-adjacent non-terminal —CH2— may be substituted by —O—, —S—, —CO—, —COO—, —OCO—, —CH═CH—, —C≡C—, —CONR4—, —NR4CO— or —NR4—);
• L represents —O—, —S—, —CO—, —COO—, —OCO—, —OCOO—, —CONR5—, —NR5CO—, —NR5— or a single bond;
• when Sp is a single bond, L is also a single bond;
• each of A1 and A2 independently represents a 1,4-phenylene group;
• one or two or more hydrogen atoms in the 1,4-phenylene group may be substituted by an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, an acyloxy group having 2 to 5 carbon atoms, an acyl group having 2 to 4 carbon atoms, an amide group having 2 to 5 carbon atoms, a cyano group or a halogen atom;
• each of Z1 and Z2 independently represents —COO—, —OCO—, —CONR6—, —NR6CO—, —OCH2—, —CH2O—, —CH2S—, —SCH2—, —CH2CH2— or a single bond;
• each of X1, X2, X3, X4, X5, X6 and X7 independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, an acyloxy group having 2 to 5 carbon atoms, an acyl group having 2 to 4 carbon atoms, an amide group having 2 to 5 carbon atoms, a cyano group or a halogen atom;
• each of R3, R4, R5 and R6 independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
• each of m and n independently represents 0, 1 or 2, and m+n=1 or 2.