Spontaneous alignment assistant for liquid crystal compositions

Patent metadata

Field	Value
Publication number	US-11345857-B2
Application number	US-202016950139-A
Country	US
Kind code	B2
Filing date	Nov 17, 2020
Priority date	Oct 26, 2016
Publication date	May 31, 2022
Grant date	May 31, 2022

Abstract

The spontaneous orientation aid for a liquid crystal composition provides storage stability and allows liquid crystal molecules to be vertically aligned without a PI layer when added to a liquid crystal composition. When used in a liquid crystal composition, the spontaneous orientation aid can adsorb to substrates sandwiching a liquid crystal composition (liquid crystal layer) and keep the liquid crystal molecules aligned in a vertical direction. The spontaneous orientation aid makes it possible to align liquid crystal molecules without a PI layer (to induce vertical alignment of liquid crystal molecules under no applied voltage and to achieve horizontal alignment of the liquid crystal molecules under an applied voltage).

First claim

The invention claimed is:

1. A liquid crystal composition comprising:
a spontaneous orientation aid represented by general formula (ii):
a compound selected from the group consisting of compounds represented by general formulae (N-1-10) and (N-1-11), and
a compound represented by General Formula (L-3.1):

wherein the liquid crystal composition has a negative dielectric anisotropy (ΔΣ),
wherein in the general formula (ii), Z ii1 represents a single bond, —COO—, —OCO—, —OCOO—, —OOCO—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 —CH 2 COO—, —OCOCH 2 —CH 2 —, —CH═C(CH 3 )COO—, —OCOC(CH 3 )═CH—, —CH 2 —CH(CH 3 )COO—, —OCOCH(CH 3 )—CH 2 —, or an alkylene group having 2 to 20 carbon atoms, wherein one or more —CH 2 —'s not adjacent to each other in the alkylene group may be replaced with —O— in which at least one Z ii1 represents a single bond;
A ii1 represents 1,4-phenylene group or a 1,4-cyclohexyl group wherein a hydrogen atom in these ring structures may be replaced with a halogen atom, P i1 -Sp i1 - wherein P i1 is described below and Sp i1 represents an alkylene group having a carbon number of 1 to 18 or a single bond, or R i1 wherein R i1 represents a hydrogen atom, a linear or branched alkyl group having 1 to 40 carbon atoms, a halogenated alkyl group, or P i1 -Sp i1 -, wherein —CH 2 — in the alkyl group may be replaced with —CH═CH—, —C≡C—, —O—, —NH—, —COO—, or —OCO—, provided that —O— moieties are not bonded in series, provided that 2, 3, 5 or 6 position of at least one A ii1 is substituted with P i1 -Sp i1 -,
when a plurality of Z i1 's or A i1 's are present, these may be the same or different,
m ii1 represents an integer of 2 to 4,
R ii1 and R ii2 each independently represent, a linear or branched alkyl group having 1 to 40 carbon atoms, or a halogenated alkyl group, wherein —CH 2 — in the alkyl group may be replaced with —CH═CH—, —C≡C—, —O—, —NH—, —COO—, or —OCO—, provided that —O— moieties are not bonded in series, at least one of R ii1 and R ii2 represents K i1 - R k -,
P i1 represents a substituent selected from the group consisting of substituents represented by general formula (P-1) to general formula (P-15) in which each black point on a right end represents atomic bonding,

K i1 represents a substituent represented by one of the general formulae (K-1), (K-9) and (K-10),

wherein W K1 represents a methine group, C—CH 3 , C—C 2 H 5 , or a nitrogen atom,
X K1 and Y K1 each independently represent an oxygen atom,
Z K1 represents an oxygen atom,
each black point on the left end in the general formula (K-1), general formula (K-9) and general formula (K-10) represents atomic bonding,
K i1 - R k - represents —CH 2 —O—K i1 , —(CH 2 ) 2 —O—CH 2 - K i1 , —O—CH 2 —K i1 , —O—(CH 2 ) 2 —K i1 , —O—(CH 2 ) 3 —K i1 , —O—(CH 2 ) 2 —O—K i1 , —O—(CH 2 ) 2 —O—CH 2 - K i1 , —O—(CH 2 ) 7 —O—CH 2 -K i1 , —O—(CH 2 ) 9 —O—CH 2 -K i1 , or —O—(CH 2 ) 8 —O—(CH 2 ) 2 —K i1 ;

wherein
R N1101 and R N1111 each independently represent an alkyl group having 1 to 8 carbon atoms, wherein one —CH 2 — or two or more —CH 2 —'s not adjacent to each other in the alkyl group each may be independently replaced with —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—,
R N1102 and R N1112 each independently represent a methoxy group or an ethoxy group,

2. The liquid crystal composition according to claim 1 wherein the compound represented by general formula (ii) is the compound represented by general formula (ii-1):

wherein Z ii1 , A ii1 and m ii1 each have the same meaning as Z ii1 , A ii1 and m ii1 ,
K ii1 has the same meaning as K i1 ,
R ii10 represents a hydrogen atom, a linear or branched alkyl group having 1 to 40 carbon atoms, a halogenated alkyl group, or P i1 -Sp i1 -, wherein —CH 2 — in the alkyl group may be replaced with —CH═CH—, —C≡C—, —O—, —NH—, —COO—, or —OCO—, provided that —O— moieties are not bonded in series, and
in the compound represented by formula (ii-1), K ii1 represent a substituent represented by one of the general formulae (K-1), (K-9) and (K-10).

3. The liquid crystal composition according to claim 1 , further comprising:
a compound represented by general formula (L):

wherein
R L1 and R L2 each independently represent an alkyl group having 1 to 8 carbon atoms, wherein one —CH 2 — or two or more —CH 2 —'s not adjacent to each other in the alkyl group each may be independently replaced with —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—,
n L1 represents 0, 1, 2, or 3,
A L1 , A L2 , and A L3 each independently represent a group selected from the group consisting of (a) a 1,4-cyclohexylene group, wherein one —CH 2 — or two or more —CH 2 —'s not adjacent to each other in this group may be replaced with —O—, (b) a 1,4-phenylene group, wherein one —CH═ or two or more —CH═'s not adjacent to each other in this group may be replaced with —N═, and (c) a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a decahydronaphthalene-2,6-diyl group, wherein one —CH═ or two or more —CH═'s not adjacent to each other in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be replaced with —N═, wherein the group (a), the group (b), and the group (c) each may be independently substituted with a cyano group, a fluorine atom, or a chlorine atom,
Z L1 and Z L2 each independently represent a single bond, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —OCF 2 —, —CF 2 O—, —CH═N—N═CH—, —CH═CH—, —CF═CF—, or —C≡C—,
when n L1 is 2 or 3 and a plurality of A L2 's are present, these may be the same or different, and
when n L1 is 2 or 3 and a plurality of Z L2 's are present, these may be the same or different, exclusive of compounds represented by general formulae (N-1), (N-2), and (N-3).

4. The liquid crystal composition according to claim 1 , further comprising:
at least one polymerizable compound.

5. The liquid crystal composition according to claim 4 , wherein the at least one polymerizable compound includes one or more compounds represented by general formula (P):

wherein
Z p1 represents a fluorine atom, a cyano group, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms in which a hydrogen atom may be replaced with a halogen atom, an alkoxy group having 1 to 15 carbon atoms in which a hydrogen atom may be replaced with a halogen atom, an alkenyl group having 1 to 15 carbon atoms in which a hydrogen atom may be replaced with a halogen atom, an alkenyloxy group having 1 to 15 carbon atoms in which a hydrogen atom may be replaced with a halogen atom, or -SP p2 - R P2 ,
R P1 and R P2 each represent one of formula (R-I) to formula (R-IX):

wherein Sp P1 and Sp P2 is bonded at a position marked

Assignees

• Dainippon Ink & Chemicals

Inventors

• Kimura Masaomi
• Inoue Yuuichi
• AKIYAMA Hidenari
• Hayashi Masanao
• Kusumoto Tetsuo

Classifications

• C07D317/64 Primary

  Oxygen atoms · CPC title

• C09K19/14

  linked by a carbon chain · CPC title

• C09K19/2007

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

• G02F1/133765

  without a surface treatment · CPC title

• C09K19/12

  at least two benzene rings directly linked, e.g. biphenyls · CPC title