IP Library Granted Patent US 10,927,300
Granted Patent B2
US 10,927,300 · App. 16/340,798 · Granted Feb 23, 2021

Spontaneous alignment assistant for liquid crystal compositions

Inventors: Masaomi Kimura (Kita-adachi-gun, JP); Yuuichi Inoue (Kita-adachi-gun, JP); Hidenari Akiyama (Kita-adachi-gun, JP); Masanao Hayashi (Kita-adachi-gun, JP); Tetsuo Kusumoto (Kita-adachi-gun, JP)
Assignee: DIC CORPORATION
C09K19/56C07C69/54C07C69/612C07D305/06C07D309/06C07D309/30C07D309/32C07D317/64C07D319/06C09K19/12C09K19/14C09K19/2007C09K19/30C09K19/3402C09K19/3405G02F1/13G02F1/139G02F1/1337C09K2019/3422C09K2323/00C09K2323/02G02F1/1362
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Quick Facts
Patent No.
US 10,927,300
App. No.
16/340,798
Granted
Feb 23, 2021
Kind
B2
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. The spontaneous orientation aid for a liquid crystal composition includes a compound having a partial structure represented by formula (i), particularly in which K i1 is represented by one of formula (K-1) to formula (K-11). 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).

Claims (73)

1. A liquid crystal composition having a negative dielectric anisotropy (Δε) comprising a compound represented by general formula (ii-2):

wherein A ii1 and A iii1 each represent the same meaning as A ii1 ,

m ii1 represents an integer of 2 to 4,

R ii1 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,

W ki represents a methine group, C—CH 3 , or C—C 2 H 5 ,

X ii1 represents a single bond, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —OCOO—, —OOCO—, —CF 2 O—, —OCF 2 —, —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 —OCH 2 CH 2 O—, provided that at least one X ii1 represents —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 —OCH 2 CH 2 O—, and

Y ii1 represents a single bond, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —OCOO—, —OOCO—, —CF 2 O—, —OCF 2 —, —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 —CH 2 — or two or more —CH 2 —'s not adjacent to each other in the alkylene group may be replaced with —O—, —COO—, or —OCO—.

2. 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 0-, (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.

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 by *, R 2 to R 6 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, W represents a single bond, —O—, or a methylene group, T represents a single bond or —COO—, p, t, and q each independently represent 0, 1, or 2,

Sp P1 and Sp P2 each represent a spacer group,

L P1 and L P2 each independently represent a single bond, —O—, —S—, —CH 2 —, —OCH 2 —, —CH 2 O—, —CO—, —C 2 H 4 —, —COO—, —OCO—, —OCOOCH 2 —, —CH 2 OCOO—, —OCH 2 CH 2 O—, —CO—NR a —, —NR a —CO—, —SCH 2 —, —CH 2 S—, —CH═CR a —COO—, —CH═CR a —OCO—, —COO—CR a ═CH—, —OCO—CR a ═CH—, —COO—CR a ═CH—COO—, —COO—CR a ═CH—OCO—, —OCO—CR a ═CH—COO—, —OCO—CR a ═CH—OCO—, —(CH 2 ) z —C(═O)—O—, —(CH 2 ) z —O—(C═O)—, —O—(C═O)—(CH 2 ) z —, —(C═O)—O—(CH 2 ) z —, —CH 2 (CH 3 )C—C(═O)—O—, —CH 2 (CH 3 )C—O—(C═O)—, —O—(C═O)—C(CH 3 )CH 2 , —(C═O)—O—C(CH 3 )—CH 2 , —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —CF 2 —, —CF 2 O—, —OCF 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, or —C≡C—, wherein R a 's each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and z represents an integer of 1 to 4,

M P2 represents a 1,4-phenylene group, a 1,4-cyclohexylene group, 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 indane-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 1,3-dioxane-2,5-diyl group, or a single bond,

M P2 may be unsubstituted or substituted with an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group, or —R P1 ,

M P1 represents one of the following formulae (i-11) to (ix-11):

wherein SP P1 is bonded at a position marked by *, and L P1 , L P2 , or Z P1 is bonded at a position marked by **,

M P3 represents one of formulae (i-13) to (ix-13):

wherein Z P1 is bonded at a position marked by *, and L P2 is bonded at a position marked by **,

m P2 to m P4 each independently represent 0, 1, 2, or 3,

m P1 and m P5 each independently represent 1, 2, or 3,

when a plurality of Z P1 's are present, these may be the same or different,

when a plurality of R P1 's are present, these may be the same or different,

when a plurality of R P2 's are present, these may be the same or different,

when a plurality of Sp P1 's are present, these may be the same or different,

when a plurality of Sp P2 's are present, these may be the same or different,

when a plurality of L P1 's are present, these may be the same or different, and

when a plurality of M P2 's are present, these may be the same or different.

6. A liquid crystal display element comprising:

two substrates; and

a liquid crystal layer including the liquid crystal composition according to claim 1 provided between the two substrates.

7. A liquid crystal display element comprising:

two substrates; and

a liquid crystal layer including the liquid crystal composition according to claim 1 in which the compound represented by general formula (ii-2) has been polymerized.

8. The liquid crystal display element according to claim 6 , which is for active matrix driving.

9. The liquid crystal display element according to claim 6 , which is a PSA type, PSVA type, VA type, IPS type, FFS type, or ECB type.

10. The liquid crystal display element according to claim 6 ,

wherein at least one of the two substrates is not provided with any alignment film.

11. A spontaneous orientation aid for a liquid crystal composition, comprising a compound represented by general formula (ii-2):

wherein A ii1 and A iii1 each represent the same meaning as A ii1 ,

m ii1 represents an integer of 2 to 4,

R ii1 represents a hydrogen atom, a linear or branched alkyl group having 1 to 40 carbon atoms, a halogenated alkyl group, or 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,

W ki represents a methine group, C—CH 3 , or C—C 2 H 5 ,

X ii1 represents a single bond, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —OCOO—, —OOCO—, —CF 2 O—, —OCF 2 —, —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 —OCH 2 CH 2 O—, provided that at least one X ii1 represents —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 —OCH 2 CH 2 O—, and

Y ii1 represents a single bond, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —OCOO—, —OOCO—, —CF 2 O—, —OCF 2 —, —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 —CH 2 — or two or more CH 2 —'s not adjacent to each other in the alkylene group may be replaced with —O—, —COO—, or —OCO—.

12. A compound represented by general formula (ii-2):

wherein A ii1 and A iii1 each represent the same meaning as A ii1 ,

m ii1 represents an integer of 2 to 4,

R ii1 represents a hydrogen atom, a linear or branched alkyl group having 1 to 40 carbon atoms, a halogenated alkyl group, P i1 -Sp i1 -, or 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,

W ki represents a methine group, C—CH 3 , or C—C 2 H 5 ,

X ii1 represents a single bond, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —OCOO—, —OOCO—, —CF 2 O—, —OCF 2 —, —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 —OCH 2 CH 2 O—, provided that at least one X ii1 represents —CH 2 —CH 2 COO—, —OCOCH 2 —CH 2 —, —CH═C(CH)COO—, —OCOC(CH 3 )═CH—, —CH 2 —CH(CH)COO—, —OCOCH(CH)—CH 2 —, or —OCH 2 CH 2 O—, and

Y ii1 represents a single bond, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —OCOO—, —OOCO—, —CF 2 O—, —OCF 2 —, —CH═CHCOO—, —OCOCH═CH—, —CH 2 —CH 2 COO—, —OCOCH 2 —CH 2 —, —CH═C(CH)COO—, —OCOC(CH)═CH—, —CH 2 —CH(CH)COO—, —OCOCH(CH 3 )—CH 2 —, or an alkylene group having 2 to 20 carbon atoms, wherein one —CH 2 — or two or more —CH 2 —'s not adjacent to each other in the alkylene group may be replaced with —O—, —COO—, or —OCO—.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2024
From: DIC CORPORATION
To: SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIAL CO., LTD.
Reel/Frame 067528/0688 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2019
From: KIMURA, MASAOMI; INOUE, YUUICHI; AKIYAMA, HIDENARI; HAYASHI, MASANAO; KUSUMOTO, TETSUO
To: DIC CORPORATION
Reel/Frame 048847/0318 →
Priority Claims (2)
JP JP2016-209592 · Oct 26, 2016 · national
JP JP2017-109171 · Jun 1, 2017 · national
Continuity (1)
Related Publication 20190264108A1 · Aug 29, 2019