Spontaneous alignment assistant for liquid crystal compositions

Patent metadata

Field	Value
Publication number	US-2021071084-A1
Application number	US-202016950139-A
Country	US
Kind code	A1
Filing date	Nov 17, 2020
Priority date	Oct 26, 2016
Publication date	Mar 11, 2021
Grant date	—

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

1 . A compound represented by general formula (ii):

wherein 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 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 - (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 (R i1 representing 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 —, provided that when K i1 is (K-11), at least one of Z ii1 is one ofCH 2 CCOO—, —OCOCH 2 —CH 2 —, —CH 2 —CH(CH 3 )COO—, —OCOCH(CH 3 )—CH 2 —, and —OCH 2 CH 2 O—,
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 KI 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 .

2 . The compound 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 . A spontaneous orientation aid for a liquid crystal composition, comprising:
the compound represented by general formula (ii) according to claim 1 .

4 . A liquid crystal composition comprising:
the spontaneous orientation aid for a liquid crystal composition according to claim 3 , wherein the liquid crystal composition has a negative dielectric anisotropy (Δε).

5 . The liquid crystal composition according to claim 1 , further comprising a compound selected from the group consisting of compounds represented by general formulae (N-1), (N-2), and (N-3):

wherein
R N11 , R N12 , R N21 , R N22 , R N31 , and R N32 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—,
A N11 , A N12 , A N21 , A N22 , A N31 , and A N32 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═, (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═, and (d) a 1,4-cyclohexenylene group, wherein the group (a), the group (b), the group (c), and the group (d) each may be independently substituted with a cyano group, a fluorine atom, or a chlorine atom,
Z N11 , Z N12 , Z N21 , Z N22 , Z N31 , and Z N32 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—,
X N21 represents a hydrogen atom or a fluorine atom,
T N31 represents —CH 2 — or an oxygen atom,
n N11 , n N12 , n N21 , n N22 , n N31 , and n N32 each independently represent an integer of 0 to 3, provided that n N11 +n N12 , n N21 +n N22 , and n N31 +n N32 are each independently 1, 2, or 3, two or more occurrences of one of A N11 's to A N32 's and Z N11 's to Z N32 's may be the same or different.

6 . 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

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

• C09K2323/00

  Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition · CPC title

• C07D309/30

  Oxygen atoms, e.g. delta-lactones · CPC title

• G02F1/133703

  by introducing organic surfactant additives into the liquid crystal material · CPC title