Polymerizable compound, and liquid crystal composition and liquid crystal display element in which the compound is used

Patent metadata

Field	Value
Publication number	US-11760934-B2
Application number	US-201816754409-A
Country	US
Kind code	B2
Filing date	Nov 1, 2018
Priority date	Nov 17, 2017
Publication date	Sep 19, 2023
Grant date	Sep 19, 2023

Abstract

The compound is represented by general formula (i). In the compound, in a group K i1 , at least two secondary carbon atoms in an alkyl group (a linear alkyl, halogenated alkyl, or cyanogenated alkyl group having 3 to 40 carbon atoms) are replaced with —C(═X i1 )— and/or —CH(—CN)—, where X i1 is an oxygen atom, a sulfur atom, NH, or NR 13 ; in addition, a group A i2 , a group A i3 , or the group K i1 includes, as a substituent, at least one P i1 -Sp i1 - group, where P i1 is a polymerizable group, and SP i1 is a spacer group or a single bond. The liquid crystal composition including the compound represented by general formula (i) can be adsorbed onto substrates between which a liquid crystal layer is held, and, consequently, without the use of an alignment film, liquid crystal molecules can be maintained in a state in which the liquid crystal molecules are aligned in a vertical direction.

First claim

The invention claimed is:

1. A compound represented by general formula (i),

wherein
R i1 independently represents a linear alkyl or halogenated alkyl group having 1 to 40 carbon atoms, or a branched alkyl having 3 to 40 carbon atoms, and a secondary carbon atom in the group is optionally replaced with —O—, —CH═CH—, or —C≡C— provided that oxygen atoms are not directly adjacent to each other,
A i1 , A i2 , and A i3 each independently represent a divalent aromatic group, a divalent cycloaliphatic group, or a divalent heterocyclic compound group; a hydrogen atom in A i1 is optionally replaced with L i1 , and hydrogen atoms in A i2 and A i3 are optionally replaced with L i1 , P i1 -Sp i1 -, or K i1 ; and L i1 represents a halogen atom, a cyano group, a nitro group, a linear alkyl or halogenated alkyl group having 1 to 40 carbon atoms, or a branched alkyl having 3 to 40 carbon atoms, and a secondary carbon atom in the alkyl group is optionally replaced with —CH═CH—, —C≡C—, —O—, —NH—, —COO—, or —OCO— provided that oxygen atoms are not directly adjacent to each other,
Z i1 and Z i2 each independently represent a single bond, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —OCOO—, —CF 2 O—, —OCF 2 —, —CH═CHCOO—, —OCOCH═CH—, —CH═C(CH 3 )COO—, —OCOC(CH 3 )═CH—, —CH 2 —CH(CH 3 )COO—, —OCOCH(CH 3 )—CH 2 —, —OCH 2 CH 2 O—, or an alkylene group having 2 to 20 carbon atoms, and one —CH 2 — group or two or more non-adjacent —CH 2 — groups in the alkylene group are optionally replaced with —O—, —COO—, or —OCO—,
K i1 is a group represented by one of general formulae (K-1) to (K-5),

wherein
Y i1 represents a linear or branched alkyl, halogenated alkyl, or cyanogenated alkyl group having 3 to 20 carbon atoms; at least two secondary carbon atoms in the alkyl group are replaced with —C(═X i1 )— and/or —CH(—CN)—; a secondary carbon atom in the alkyl group is optionally replaced with —CH═CH—, —C≡C—, —O—, —NH—, —COO—, or —OCO— provided that oxygen atoms are not directly adjacent to each other; a hydrogen atom in the alkyl group is optionally replaced with P i1 -Sp i1 -; and X i1 represents an oxygen atom, a sulfur atom, NH, or NR i1 ,
S i1 and S i3 each independently represent an alkylene group having 1 to 6 carbon atoms or a single bond, and —CH 2 — in the alkylene group is optionally replaced with —CH═CH—, —C≡C—, —C(═CH 2 )—, —C(═CHR i3 )—, —C(═CR i32 )—, —O—, —NH—, —C(═O)—, —COO—, or —OCO— provided that oxygen atoms are not directly adjacent to each other, R i3 represents a linear alkyl group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, and a secondary carbon atom in the alkyl group is optionally replaced with —O—, —CH═CH—, or —C≡C— provided that oxygen atoms are not directly adjacent to each other,
S i2 represents a carbon atom,
R i2 represents a hydrogen atom or a linear alkyl having 1 to 20 carbon atoms or branched alkyl having 3 to 20 carbon atoms, and a secondary carbon atom in the group is optionally replaced with —O—, —CH═CH— or —C≡C— provided that oxygen atoms are not directly adjacent to each other,
P i1 represents a polymerizable group selected from the group consisting of the groups represented by general formulae (P-1) to (P-16),

wherein a black dot at a right end represents a bond,
SP i1 represents a spacer group or a single bond,
n i1 represents an integer of 1 to 3, and n i2 represents 1 or 2, and n i3 represents an integer of 0 to 2; and n i1 +n i2 +n i3 is 3,
R i3 has a same meaning as R i3 in general formula (i),
in general formula (K-1), when any of R i2 , X i1 , Y i1 , S i1 , S i3 , P i1 , and SP i1 is a plurality of units, the units are identical to or different from one another,

wherein S i1 , P i1 , and SP i1 have a same meaning as, respectively, S i1 , P i1 , and SP i1 in general formula (K-1); R K21 represents a linear alkyl group having 1 to 10 carbon atoms, branched alkyl group having 3 to 10 carbon atoms, or halogenated alkyl or cyanogenated alkyl group having 1 to 10 carbon atoms, and at least one secondary carbon atom in the alkyl group is optionally replaced with —CH═CH—, —C≡C—, —O—, or —NH— provided that oxygen atoms are not directly adjacent to each other; and n i4 represents 1, and n iK21 represents 0 or 1
P i1 is the same meaning as in general formula (K-1),
SP i1 represents a spacer group or a single bond,
m i1 represents an integer of 0 to 3, and
in general formula (i), when any of R i1 , A i2 , Z i2 , L i1 , K i1 , X i1 , P i1 , and SP i1 is a plurality of units, the units are identical to or different from one another.

2. The compound according to claim 1 , wherein
A i1 , A i2 , and A i3 in general formula (i) represent a ring system selected from a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenylene group, an anthracene-2,6-diyl group, a phenanthrene-2,7-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, an indan-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and a 1,3-dioxane-2,5-diyl group, and
a hydrogen atom in A i1 is optionally replaced with L i1 , and hydrogen atoms in A i2 and A i3 are optionally replaced with L i1 , P i1 -Sp i1 -, or K i1 .

3. The compound according to claim 1 , wherein P i1 in general formula (i) represents the general formula (P-1) or (P-2).

4. The compound according to claim 1 , wherein R i1 in general formula (i) represents an alkyl group having 3 or more carbon atoms, and —CH 2 — in the alkyl group is optionally replaced with —O— provided that oxygen atoms are not directly adjacent to each other.

5. The compound according to claim 1 , wherein Y i1 in general formula (K-1) represents a group selected from general formula (Y-1),

wherein W iY1 represents a single bond or an oxygen atom; a dashed line represents a single bond or a double bond; when the dashed line represents a single bond, R iY1 represents a hydrogen atom or a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, and a secondary carbon atom in the alkyl group is optionally replaced with —O—, —CH═CH— or —C≡C— provided that oxygen atoms are not directly adjacent to each other; when the dashed line represents a double bond, R iY1 represents ═CH 2 , ═CHR iY4 , or ═CR iY4 2 , where R iY4 represents a hydrogen atom or a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, and a secondary carbon atom in the alkyl group is optionally replaced with —O—, —CH═CH—, or —C≡C— provided that oxygen atoms are not directly adjacent to each other; R iY3 has a same meaning as R iY1 associated with a case where the dashed line represents a single bond; R iY2 represents a hydrogen atom or a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, and a secondary carbon atom in the alkyl group is optionally replaced with —O—, —CH═CH—, or —C≡C— provided that oxygen atoms are not directly adjacent to each other; n iY1 is 0 when the dashed line represents a do

Assignees

• Dainippon Ink & Chemicals

Inventors

• Shimizu Kenta
• Hayashi Masanao
• Kadomoto Yutaka
• Kusumoto Tetsuo
• HOSONO Ayaki
• Yamamoto Shinya
• Miyamoto Masanori
• Kai Hidetomo

Classifications

• C07D319/06 Primary

  not condensed with other rings · CPC title

• C07C69/54 Primary

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C09K19/46 Primary

  containing esters · CPC title

• C07C255/19

  containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton · CPC title

• C08F20/20

  of polyhydric alcohols or {polyhydric} phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title