Polymerizable compound, polymerizable composition, polymer, optically anisotropic body, and method for producing polymerizable compound

Patent metadata

Field	Value
Publication number	US-10173992-B2
Application number	US-201615179145-A
Country	US
Kind code	B2
Filing date	Jun 10, 2016
Priority date	Jul 9, 2012
Publication date	Jan 8, 2019
Grant date	Jan 8, 2019

Abstract

A polymerizable compound has a practical low melting point, excellent solubility in a general-purpose solvent, and can produce an optical film at low cost, exhibits low reflected luminance, and achieves uniform conversion of polarized light over a wide wavelength band, an optically anisotropic article. A carbonyl compound is useful as a raw material for producing the polymerizable compound. (In the formula (I), Y 1 to Y 8 represent —C(═O)—O—, G 1 and G 2 represent a C 1-20 divalent linear aliphatic group, Z 1 and Z 2 represent a C 2-10 alkenyl group that is unsubstituted, or substituted with a halogen atom, A x represents a C 2-30 organic group with at least one aromatic ring, A y represents a hydrogen atom or C 1-20 alkyl group, A 1 represents a trivalent aromatic group, A 2 and A 3 represent a C 3-30 divalent alicyclic hydrocarbon group, A 4 and A 5 represent a C 6-30 divalent aromatic group or the like, and Q 1 represents a hydrogen atom.)

First claim

The invention claimed is:

1. A polymer obtained by polymerizing a polymerizable compound represented by a formula (I),

or a polymerizable composition comprising at least one polymerizable compound represented by a formula (I) and an initiator; wherein
Y 1 to Y 8 are independently a chemical single bond, —O—, —S—, —O—C(═O)—, —C(═O)—O—, —O—C(═O)—O—, —NR 1 —C(═O)—, —C(═O)—NR 1 —, —O—C(═O)—NR 1 —, —NR 1 —C(═O)—O—, —NR 1 —C(═O)—NR 1 —, —O—NR 1 —, or —NR 1 —O—, R 1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
G 1 and G 2 are independently a substituted or unsubstituted divalent linear aliphatic group having 1 to 20 carbon atoms that optionally includes —O—, —S—, —O—C(═O)—, —C(═O)—O—, —O—C(═O)—O—, —NR 2 —C(═O)—, —C(═O)—NR 2 —, —NR 2 —, or —C(═O)—, provided that a case where the aliphatic group includes two or more contiguous —O— or —S— is excluded, R 2 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
Z 1 and Z 2 are independently an alkenyl group having 2 to 10 carbon atoms that is unsubstituted, or substituted with a halogen atom,
A x is an organic group having 2 to 30 carbon atoms that includes at least one aromatic ring selected from a group consisting of an aromatic hydrocarbon ring and a heteroaromatic ring,
A y is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, —C(═O)—R 3 , —SO 2 —R 4 , —C(═S)NH—R 9 , or an organic group having 2 to 30 carbon atoms that includes at least one aromatic ring selected from a group consisting of an aromatic hydrocarbon ring and a heteroaromatic ring, R 3 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 5 to 12 carbon atoms, R 4 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a phenyl group, or a 4-methylphenyl group, R 9 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, or a substituted or unsubstituted aromatic group having 5 to 20 carbon atoms,
provided that the aromatic ring included in A x and A y is substituted or unsubstituted, and
A x and A y are optionally bonded to each other to form a ring,
A 1 is a substituted or unsubstituted trivalent aromatic group,
A 2 and A 3 are independently a substituted or unsubstituted divalent alicyclic hydrocarbon group having 3 to 30 carbon atoms,
A 4 and A 5 are independently a substituted or unsubstituted divalent aromatic group having 6 to 30 carbon atoms, and
Q 1 is a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

2. The polymer according to claim 1 , the polymer being a liquid crystalline polymer.

3. An optically anisotropic article comprising the polymer according to claim 2 .

4. A method comprising:
reacting a raw material comprising a carbonyl compound to produce a polymerizable compound; wherein
the carbonyl compound is represented by a formula (4):

where
Y 1 to Y 8 are independently a chemical single bond, —O—, —S—, —O—C(═O)—, —C(═O)—O—, —O—C(═O)—O—, —NR 1 —C(═O)—, —C(═O)—NR 1 —, —O—C(═O)—NR 1 —, —NR 1 —C(═O)—O—, —NR 1 —C(═O)—NR 1 —, —O—NR 1 —, or —NR 1 —O—, R 1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
G 1 and G 2 are independently a substituted or unsubstituted divalent linear aliphatic group having 1 to 20 carbon atoms that optionally includes —O—, —S—, —O—C(═O)—, —C(═O)—O—, —O—C(═O)—O—, —NR 2 —C(═O)—, —C(═O)—NR 2 —, —NR 2 —, or —C(═O)—, provided that a case where the aliphatic group includes two or more contiguous —O— or —S— is excluded, R 2 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
Z 1 and Z 2 are independently an alkenyl group having 2 to 10 carbon atoms that is unsubstituted, or substituted with a halogen atom,
A 1 is a substituted or unsubstituted trivalent aromatic group,
A 2 and A 3 are independently a substituted or unsubstituted divalent alicyclic hydrocarbon group having 3 to 30 carbon atoms,
A 4 and A 5 are independently a substituted or unsubstituted divalent aromatic group having 6 to 30 carbon atoms, and
Q 1 is a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; and
the polymerizable compound is represented by a formula (I):

where
A x is an organic group having 2 to 30 carbon atoms that includes at least one aromatic ring selected from a group consisting of an aromatic hydrocarbon ring and a heteroaromatic ring,
A y is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, —C(═O)—R 3 , —SO 2 —R 4 , —C(═S)NH—R 9 , or an organic group having 2 to 30 carbon atoms that includes at least one aromatic ring selected from a group consisting of an aromatic hydrocarbon ring and a heteroaromatic ring, R 3 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 5 to 12 carbon atoms, R 4 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a phenyl group, or a 4-methylphenyl group, R 9 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, or a substituted or unsubstituted aromatic group having 5 to 20 carbon atoms, provided that the aromatic ring included in A x and A y is substituted or unsubstituted, and A x and A y are optionally bonded to each other to form a ring, and
Y 1 to Y 8 , G 1 , G 2 , Z 1 , Z 2 , A 1 , A 2 , A 3 , A 4 , A 5 and Q 1 are the same as defined above in connection with formula (4).

5. The method according claim 4 , wherein A 1 of the carbonyl compound represented by formula (4) is a substituted or unsubstituted trivalent benzene ring group, or a substituted or unsubstituted trivalent naphthalene ring group.

6. The method according claim 4 , wherein A 2 and A 3 of the carbonyl compound represented by formula (4) are independently a substituted or unsubstituted divalent cyclohexyl group.

7. The method according claim 4 , wherein Z 1 and Z 2 of the carbonyl compound represented by formula (4) are independently CH 2 ═CH—, CH 2 ═C(CH 3 )—, or CH 2 ═C(Cl)—.

Assignees

• Zeon Corp

Inventors

• Sakamoto Kei
• Kiriki Satoshi
• Okuyama Kumi
• TAIRA Kanako

Classifications

• C08F22/1006

  of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate · CPC title

• C07D277/82 Primary

  Nitrogen atoms · CPC title

• G02B5/30

  Polarising elements (light-modulating devices with active elements G02F1/00) · CPC title

• C08F22/26

  of unsaturated alcohols {(C08F22/1006 takes precedence)} · CPC title

• C07C69/753

  of polycyclic acids · CPC title