Method for producing polymerizable compound

1. A method for producing a polymerizable compound comprising:

a step of reacting a compound represented by General Formula (I-B-a):

W 2 —NH—NH 2    (I-B-a)

wherein W 2 represents a linear or branched alkyl group having 2 to 20 carbon atoms in which one —CH 2 — or two or more non-adjacent —CH 2 —'s may each independently be substituted with —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 arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom,

with a compound represented by General Formula (I-B-b):

wherein r represents an integer of 0 to 4, L W1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which one —CH 2 — or two or more non-adjacent —CH 2 —'s may each independently be substituted with —O—, —S—, —CH═CH—, —CF═CF—, or —C≡C—, and arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, plural L W1 's, if any, may be the same or different, and LG 1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, a methylsulfanyl group, a hydroxyl group, a mercapto group, an amino group, a methylamino group, a dimethylamino group, a hydrazinyl group, or a benzothiazol-2-yl disulfanyl group

to thereby obtain a compound represented by General Formula (I-C):

wherein W 2 , r, and L W1 represent the same meanings as defined above,

the compound represented by General Formula (I-B-a) is produced by a reaction between a compound represented by General Formula (I-A) and hydrazine:

W 2 -LG 2    (I-A)

W 2 represents the same meaning as defined in General Formula (I-B-a), and LG 2 represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyl group, or a p-toluenesulfonyl group the reaction is carried out in the presence of an alkali or a base,

the polymerizable compound is represented by General Formula (I):

wherein W 2 , r, and L W1 represent the same meanings as defined in General Formula (I-B-a) or General Formula (I-B-b);

P 1 represents a polymerizable group, and the polymerizable group is a group polymerizable by radical polymerization, radical addition polymerization, cationic polymerization, or anionic polymerization;

Sp 1 represents a spacer group, and plural Sp 1 's, if any, may be the same or different;

X 1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —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—, —CF═CF—, or —C≡C—, a single bond, and plural X 1 's, if any, may be the same or different;

k 1 represents an integer of 0 to 10;

R represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms in which arbitrary hydrogen atoms in the group may be substituted with a fluorine atom, and one —CH 2 — or two or more non-adjacent —CH 2 —'s may each independently be substituted with —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —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—, —CF═CF—, or —C≡C—, or R represents a group represented by —(X 2 —Sp 2 ) k2 -P 2 , where P 2 represents a polymerizable group, and the polymerizable group is a group polymerizable by radical polymerization, radical addition polymerization, cationic polymerization, or anionic polymerization, Sp 2 represents a spacer group, plural Sp 2 's, if any, Sp 2 's may be the same or different, X 2 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —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—, —CF═CF—, —C≡C—, or a single bond, plural X 2 's, if any, may be the same or different, and k2 represents an integer of 0 to 10;

A 1 and A 2 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more substituents L, plural A 1 's, if any, may be the same or different, and plural A 2 's, if any, may be the same or different, L represents 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 having 1 to 20 carbon atoms in which one —CH 2 — or two or more non-adjacent —CH 2 —'s may each independently be substituted with —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 arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, or L may represent a group represented by P L —(Sp L -X L ) kL — where, P L represents a polymerizable group, and the polymerizable group is a group polymerizable by radical polymerization, radical addition polymerization, cationic polymerization, or anionic polymerization, Sp L represents a spacer group or a single bond, plural Sp L 's, if any, may be the same or different, X L represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —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—, —CF═CF—, —C≡C—, or a single bond, plural X L 's, if any, may be the same or different, kL represents an integer of 0 to 10, and plural kL's, if present in the compound, may be the same or different;

Z 1 and Z 2 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, plural Z 1 's, if any, may be the same or different, and plural Z 2 's, if any, may be the same or different;

m1 and m2 each independently represent an integer of 0 to 6, provided that m1+m2 represents an integer of 0 to 6;

M represents a trivalent aromatic group which may be substituted; and

Y represents a hydrogen atom, 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 having 1 to 20 carbon atoms in which one —CH 2 — or two or more non-adjacent —CH 2 —'s may each independently be substituted with —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 arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, provided that the compound represented by General Formula (I) does not include an —O—O— bond.

2. The method for producing a polymerizable compound according to claim 1 , wherein, in General Formula (I-B-a), W 2 represents a linear or branched alkyl group having 2 to 20 carbon atoms in which one —CH 2 — or two or more non-adjacent —CH 2 —'s may each independently be substituted with —O—, —S—, —CH═CH—, —CF═CF—, or —C≡C—, provided that arbitrary hydrogen atoms in the alkyl group and the hydroxyalkyl group may be substituted with a fluorine atom.

3. The method for producing a polymerizable compound according to claim 1 ,

wherein, in General Formula (I), O 1 , and if present, P 2 represent a group selected from Formula (P-1) to Formula (P-20):

4. The method for producing a polymerizable compound according to claim 1 ,

wherein, in General Formula (I), Sp 1 and if present, Sp 1 each independently represent an alkylene group having 1 to 20 carbon atoms in which one —CH 2 — or two or more non-adjacent —CH 2 —'s may each independently be substituted with —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH—, or —C≡C—.

5. The method for producing a polymerizable compound according to claim 1 ,

wherein, in General Formula (I), M represents a group selected from Formula (M-1) to Formula (M-6):

wherein these groups are unsubstituted or may be substituted with one or more substituents L M (L M represents 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 having 1 to 20 carbon atoms in which one —CH 2 — or two or more non-adjacent —CH 2 —'s may each independently be substituted with —O—, —S—, —CO—, —OCO—, —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 arbitrary hydrogen atoms in the alkyl group may be substituted with a fluorine atom, or L M may represent a group represented by P LM —(Sp LM -X LM ) kLM — where P LM represents a polymerizable group, and the polymerizable group is a group polymerizable by radical polymerization, radical addition polymerization, cationic polymerization, or anionic polymerization, Sp′ represents a spacer group or a single bond, plural Sp LM 's, if any, may be the same or different, X LM represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —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—, —CF═CF—, —C≡C—, or a single bond, plural s, if any, may be the same or different, kLM represents an integer of 0 to 10, and plural L M 's present in the compound, these L M 's may be the same or different, and any —CH═ may each independently be substituted with —N═.