Polymerizable composition including polymerizable liquid crystal compound, film, and method of manufacturing film

1. A polymerizable composition comprising: a polymerizable liquid crystal compound; and a urethane (meth)acrylate monomer,

wherein the polymerizable liquid crystal compound is represented by Formula (I), and

the urethane (meth)acrylate monomer includes a urethane bond represented by Formula (II) and three or more (meth)acryloyl groups,

Q 1 -Sp 1 A-L m-1 A-Sp 2 -Q 2   (I)

in Formula (I),

A's each independently represent an unsubstituted cyclohexylene group or a phenylene group having a group represented by —C(═O)—X 3 -Sp 3 -Q 3 as a substituent, provided that the polymerizable liquid crystal compound includes at least one unsubstituted cyclohexylene group and at least one phenylene group having a —C(═O)—X 3 -Sp 3 -Q 3 group as a substituent,

L represents a single bond, or a linking group selected from the group consisting of —CH 2 O—, —OCH 2 —, —(CH 2 ) 2 OC(═O)—, —C(═O)O(CH 2 ) 2 —, —C(═O)O—, —OC(═O)—, —OC(═O)O—, —CH═CH—C(═O)O—, and —OC(═O)—CH═CH—,

m represents an integer of 4 to 12,

Sp 1 and Sp 2 each independently represent a single bond or a linking group selected from the group consisting of a linear or branched alkylene group having 1 to 20 carbon atoms and a group in which one or more —CH 2 -'s in a linear or branched alkylene group having 1 to 20 carbon atoms are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—,

Q 1 and Q 2 each independently represent a hydrogen atom or a polymerizable group selected from the group consisting of groups represented by Formulae Q-1 to Q-5:

here, at least one of Q 1 and Q 2 represents a polymerizable group, and

in Formula (II), R represents a hydrogen atom or a hydrocarbon group,

the substituent in the recited groups that may have a substituent, is selected from the group consisting of an alkyl group, a cycloalkyl group, an alkoxy group, an alkyl ether group, an amide group, an amino group, a halogen atom, and a group obtained by combining two or more of the above substituents or a substituent represented by —C(═O)—X 3 -Sp 3 -Q 3 ,

in —C(═O)—X 3 -Sp 3 -Q 3 , X 3 represents a single bond, —O—, —S—, or —N(Sp 4 -Q 4 )-, or represents a nitrogen atom that forms a ring structure together with Q 3 and Sp 3 ,

each Sp 3 independently represents a group in which one or more —CH 2 -'s in a linear or branched alkylene group having 1 to 20 carbon atoms are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—,

each Sp 4 independently represents a single bond or a linking group selected from the group consisting of a linear or branched alkylene group having 1 to 20 carbon atoms and a group in which one or more —CH 2 -'s in a linear or branched alkylene group having 1 to 20 carbon atoms are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—, and

Q 3 and Q 4 each independently represents a hydrogen atom, a cycloalkyl group, a group in which one or more —CH 2 -'s in a cycloalkyl group are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—, or any one polymerizable group selected from the group consisting of groups represented by Formulae Q-1 to Q-5 above.

2. The polymerizable composition according to claim 1 , wherein, in Formula (II), R represents a hydrogen atom.

3. The polymerizable composition according to claim 1 , wherein both of Q 1 and Q 2 are polymerizable groups represented by Formula Q-1 or Q-2.

4. The polymerizable composition according to claim 1 , wherein L is —C(═O)O— or —OC(═O)—.

5. The polymerizable composition according to claim 1 , wherein both of Q 1 and Q 2 are polymerizable groups represented by Formula Q-1 or Q-2, and L is —C(═O)O— or —OC(═O)—.

6. The polymerizable composition according to claim 1 , wherein m is 4 to 5.

7. The polymerizable composition according to claim 1 , wherein the total mass of the urethane (meth)acrylate monomer is 1 to 10 mass % with respect to the total solids content of the polymerizable composition.

8. The polymerizable composition according to claim 1 , further comprising: a polymerization initiator.

9. The polymerizable composition according to claim 1 , further comprising: a chiral compound.

10. A film comprising: a layer obtained by curing the polymerizable composition according to claim 1 .

11. The polymerizable composition according to claim 1 , wherein the polymerizable liquid crystal compound is represented by Formula (I-21) or (I-31):

wherein in Formula (I-21), A 21 and A 22 each independently represents a trans-1,4-cyclohexylene group that may have a substituent, an arylene group that may have a substituent, or a heteroarylene group that may have a substituent,

all of the substituents each independently represents one to four substituents selected from the group consisting of —CO—X 21 -Sp 23 -Q 23 , an alkyl group, and an alkoxy group,

m21 represents an integer of 1 or 2, n21 represents an integer of 0 or 1,

in a case where m21 represents 2, n21 represents 0,

in a case where m21 represents 2, two A 21 's may be identical to or different from each other,

at least one of A 21 and A 22 is an arylene group that may have a substituent or a heteroarylene group that may have a substituent,

L 21 , L 22 , L 23 , and L 24 each independently represents a single bond or a linking group selected from the group consisting of —CH 2 O—, —OCH 2 —, —(CH 2 ) 2 OC(═O)—, —C(═O)O(CH 2 ) 2 —, —C(═O)O—, —OC(═O)—, —OC(═O)O—, —CH═CH—C(═O)O—, and —OC(═O)—CH═CH—,

X 21 represents —O—, —S—, or —N(Sp 25 -Q 25 )-, or represents a nitrogen atom that forms a ring structure together with Q 23 and Sp 23 ,

r 21 represents an integer of 1 to 4,

Sp 21 , Sp 22 , Sp 24 , and Sp 25 each independently represents a single bond or a linking group selected from the group consisting of a linear or branched alkylene group having 1 to 20 carbon atoms and a group in which one or more —CH 2 -'s in a linear or branched alkylene group having 1 to 20 carbon atoms are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—,

each Sp 23 independently represents a group in which one or more —CH 2 -'s in a linear or branched alkylene group having 1 to 20 carbon atoms are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—,

Q 21 and Q 22 each independently represents any one polymerizable group selected from the group consisting of groups represented by Formulae Q-1 to Q-5,

Q 23 represents a hydrogen atom, a cycloalkyl group, a group in which one or more —CH 2 -'s in a cycloalkyl group are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—, any one polymerizable group selected from the group consisting of groups represented by Formulae Q-1 to Q-5, or a single bond in a case where X 21 is a nitrogen atom that forms a ring structure together with Q 23 and Sp 23 , and

Q 25 represents a hydrogen atom, a cycloalkyl group, a group in which one or more —CH 2 -'s in a cycloalkyl group are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—, or any one polymerizable group selected from the group consisting of groups represented by Formulae Q-1 to Q-5, and, in a case where Sp 25 is a single bond, Q 25 is not a hydrogen atom;

wherein in Formula (I-31), R 31 and R 32 each independently represents a group selected from the group consisting of an alkyl group, an alkoxy group, and —C(═O)—X 33 -Sp 33 -Q 33 , provided that at least one of R 31 and R 32 represents —C(═O)—X 33 -Sp 33 -Q 33 ,

n31 and n32 each independently represents an integer of 0 to 4,

X 33 represents a single bond, —O—, —S—, or —N(Sp 34 -Q 34 )-, or represents a nitrogen atom that forms a ring structure together with Q 33 and Sp 33 ,

Z 31 represents an arylene group that may have a substituent or a heteroarylene group that may have a substituent,

Z 32 represents a trans-1,4-cyclohexylene group that may have a substituent, an arylene group that may have a substituent, or a heteroarylene group that may have a substituent,

all of the substituents each independently represents one to four substituents selected from the group consisting of an alkyl group, an alkoxy group, and —C(═O)—X 33 -Sp 33 -Q 33 ,

m31 represents an integer of 1 or 2, and m32 represents an integer of 0 to 2,

in a case where m31 and m32 represent 2, two Z 31 's and two Z 32 's may be identical to or different from each other,

L 31 and L 32 each independently represents a linking group selected from the group consisting of a single bond, or a linking group selected from the group consisting of —CH 2 O—, —OCH 2 —, —(CH 2 ) 2 OC(═O)—, —C(═O)O(CH 2 ) 2 —, —C(═O)O—, —OC(═O)—, —OC(═O)O—, —CH═CH—C(═O)O—, and —OC(═O)—CH═CH—,

T 33 represents-Sp 35 -Q 35 ,

Sp 31 , Sp 32 , Sp 34 , and Sp 35 each independently represents a single bond or a linking group selected from the group consisting of a linear or branched alkylene group having 1 to 20 carbon atoms and a group in which one or more —CH 2 -'s in a linear or branched alkylene group having 1 to 20 carbon atoms are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—,

each Sp 33 independently represents a group in which one or more —CH 2 -'s in a linear or branched alkylene group having 1 to 20 carbon atoms are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—,

Q 31 and Q 32 each independently represents any one polymerizable group selected from the group consisting of groups represented by Formulae (Q-1) to (Q-5), and

Q 33 , Q 34 , and Q 35 each independently represents a hydrogen atom, a cycloalkyl group, a group in which one or more —CH 2 -'s in a cycloalkyl group are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—, any one polymerizable group selected from the group consisting of groups represented by Formulae (Q-1) to (Q-5), Q 33 may represent a single bond in a case where a ring structure is formed together with X and Sp 33 , and Q 34 is not hydrogen atom in a case where Sp 34 is a single bond.

12. The polymerizable composition according to claim 1 , wherein m in Formula (I) is 5.

13. The polymerizable composition according to claim 1 , wherein the content of the urethane (meth)acrylate monomer is 1.5 mass % to 5.0 mass % with respect to the total mass solids content of the polymerizable composition.