Polymerizable composition and optically anisotropic body using same

Patent metadata

Field	Value
Publication number	US-11697695-B2
Application number	US-201615543430-A
Country	US
Kind code	B2
Filing date	Jan 12, 2016
Priority date	Jan 16, 2015
Publication date	Jul 11, 2023
Grant date	Jul 11, 2023

Abstract

A polymerizable composition containing: a) a polymerizable compound having one or two or more polymerizable groups and satisfying formula (I): Re(450 nm)/Re(550 nm)<1.0 (I); b) at least one photopolymerization initiator selected from the group consisting of alkylphenone-based compounds, acylphosphine oxide-based compounds, and oxime ester-based compounds; and c) a polymerization inhibitor. An optically anisotropic body, a retardation film, an antireflective film, and a liquid crystal display device that are produced using the polymerizable liquid crystal composition. The polymerizable composition is excellent in solubility and has high storage stability, so that no precipitation of crystals etc. occurs. When a film-shaped polymer is produced by polymerizing the above composition, the unevenness of the surface of the coating film is small while the alignment of the liquid crystal is maintained, and high durability is obtained. Therefore, the polymerizable composition is useful.

First claim

The invention claimed is:

1. A polymerizable composition comprising:
a) a polymerizable compound having one or more polymerizable groups and satisfying formula (I):
Re(450 nm)/Re(550 nm)<1.0  (I)

wherein Re(450 nm) is an in-plane retardation at a wavelength of 450 nm when the polymerizable compound having one or more polymerizable groups is aligned on a substrate such that the direction of long axes of molecules of the polymerizable compound is substantially horizontal to the substrate, and Re(550 nm) is an in-plane retardation at a wavelength of 550 nm when the polymerizable compound having one or more polymerizable groups is aligned on the substrate such that the direction of the long axes of the molecules of the polymerizable compound is substantially horizontal to the substrate;

b) at least one photopolymerization initiator represented by formula (b-1):

wherein R 1 s each independently represent a group selected from formula (R 1 -1) to (R 1 -4) and formula (R 1 -6) below:

R 2 represents a group selected from a single bond, —O—, —C(CH 3 ) 2 , —C(OCH 3 ) 2 , and —C(CH 2 CH 3 )—N(CH 3 )2; and R 3 represents a group selected from formula (R 3 -1) to formula (R 3 -8) below:

 and

c) a phenol-based polymerization inhibitor selected from the group consisting of a hydroquinone, methoxyphenol, methylhydroquinone, tert-butylhydroquinone, or tert-butylcatechol,
wherein the polymerizable compound having one or more polymerizable groups and satisfying formula (I) comprises at least one selected from liquid crystalline compounds represented by general formula (1) and at least one selected from liquid crystalline compound represented by general formula (2):

wherein P 11 to P 22 each represent any of general formulas (P-1) to (P-3):

S 11 to S 22 each represent an alkylene group which has 1 to 20 carbon atoms and in which one —CH 2 — group or two or more nonadjacent —CH 2 — groups may be each independently replaced by —O—, —COO—, —OCO—, —OCO—O—, —CO—NH—, —NH—CO—, —CH═CH—, —C≡C—, or formula (S-1) below:

when a plurality of S 11 s to S 22 s are present, they may be the same or different;

X 11 to X 22 each represent —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 provided that each P—(S—X)— bond contains no —O—O—; when a plurality of X 11 s to X 22 s are present, they may be the same or different;
MG 11 to MG 21 each independently represent formula (a):

wherein A 11 and A 12 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, each of which may be unsubstituted or substituted by at least one L 1 ; when a plurality of A 11 s and/or A 12 s are present, they may be the same or different;

Z 11 and Z 12 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—, —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; when a plurality of Z 11 s and/or Z 12 s are present, they may be the same or different;
M represents a group selected from formula (M-1) to formula (M-2) below:

the groups represented by formula (M-1) to formula (M-2) may be unsubstituted or substituted by at least one L 1 ;
G is formula (G-1) below:

wherein R 3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, the alkyl group being linear or branched, wherein the branched alkyl has 3 to 20 carbon atoms, any hydrogen atom in the alkyl group being optionally replaced by a fluorine atom, one —CH 2 — group or more nonadjacent —CH 2 — groups in the alkyl group being each independently optionally replaced by —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, or —C≡C—;
W 81 represents formula (W-a-5):

wherein s represents an integer from 0 to 4;
W 82 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, the alkyl group being linear or branched, wherein the branched alkyl has 3 to 20 carbon atoms, any hydrogen atom in the alkyl group being optionally replaced by a fluorine atom, one —CH 2 — group or more nonadjacent —CH 2 — groups in the alkyl group being each independently optionally replaced by —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, or —C≡C—; the meaning of W 82 may be the same as the meaning of W 81 ;
L 1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro 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 an alkyl group having 1 to 20 carbon atoms, the alkyl group being linear or branched, wherein the branched alkyl has 3 to 20 carbon atoms, any hydrogen atom in the alkyl group being optionally replaced by a fluorine atom, one —CH 2 — group or more nonadjacent —CH 2 — groups in the alkyl group being each independently optionally replaced by a group selected from —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—, and —C≡C—; when a plurality of L 1 s are present in the compound, they may be the same or different;
j11 represents an integer from 1 to 5; and j12 represents an integer of 1 to 5 while j11+j12 is an integer from 2 to 5;
R 11 each represent 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 an alkyl group having 1 to 20 carbon atoms, the alkyl group being linear or branched, wherein the branched alkyl has 3 to 20 carbon atoms, any hydrogen atom in the alkyl group being optionally replaced by a fluorine ato

Assignees

• Dainippon Ink & Chemicals

Inventors

• Endo Kouichi
• Ishii Toru
• Kuwana Yasuhiro
• Hatsusaka Kazuaki
• Yamamoto Mika

Classifications

• C09K19/2007

  the chain containing -COO- or -OCO- groups · CPC title

• C08F2/50

  with sensitising agents · CPC title

• C08F2/48

  by ultraviolet or visible light · CPC title

• C08F20/38

  Esters containing sulfur · CPC title

• G02B5/30

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