Nematic liquid crystal composition, and liquid crystal display element manufactured using same

Patent metadata

Field	Value
Publication number	US-10465113-B2
Application number	US-201615547964-A
Country	US
Kind code	B2
Filing date	Apr 14, 2016
Priority date	Apr 24, 2015
Publication date	Nov 5, 2019
Grant date	Nov 5, 2019

Abstract

The present invention is a liquid crystal composition having negative dielectric anisotropy containing one or two or more of compounds represented by General Formula (i), and is also a liquid crystal display element using the liquid crystal composition. The problem to be solved by the present invention is to provide a liquid crystal composition with a large refractive index anisotropy (Δn), a low rotational viscosity (γ1), a large elastic constant (K33), a high voltage holding ratio (VHR), and which has a negative dielectric anisotropy (Δε), and a liquid crystal display element which, when using the liquid crystal composition, has a high response speed with excellent display quality in which display defects such as drop marks, burn-in, and display unevenness are absent or suppressed.

First claim

The invention claimed is:

1. A liquid crystal composition having negative dielectric anisotropy, comprising
at least one compound represented by General Formula (i):

wherein R i1 and R i2 each independently represent an alkyl group having 1 to 10 carbon atoms, one or two or more non-adjacent —CH 2 — in R i1 and R i2 may each independently be substituted with —CH═CH—, —C≡—, —O—, —S—, —COO—, —OCO—, or —CO—, and one or two or more of the hydrogen atoms present in R i1 and R i2 may each independently be substituted with a fluorine atom or a chlorine atom;
A i1 and A i2 each independently represent a group selected from a trans-1,4-cyclohexylene group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, a 3,5-difluoro-1,4-phenylene group, a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group;
Z i1 and Z i2 are each independently 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—;
n i1 and n i2 each independently represent 0, 1 or 2, provided that n i1 +n i2 is 2 or more; and
in a case where n i1 is 2 and therefore plural A i1 's and plural Z i1 's are present, plural A i1 's may be the same or different and plural Z i1 's may be the same or different, and in a case where n i2 is 2 and therefore plural A i2 's and plural Z i2 's are present, plural A i2 's may be the same or different and plural Z i2 's may be the same or different.

2. The liquid crystal composition according to claim 1 ,
wherein, in General Formula (i), R i2 is a methyl group.

3. The liquid crystal composition according to claim 1 ,
wherein, in General Formula (i), A i1 and A i2 are each independently a group selected from a trans-1,4-cyclohexylene group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, or a 3-fluoro-1,4-phenylene group.

4. The liquid crystal composition according to claim 1 ,
wherein, in General Formula (i), n i1 is 2, and n i2 is 0.

5. The liquid crystal composition according to claim 1 , further comprising:
at least one compound selected from compounds represented by General Formulas (N-1), (N-2), or (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 10 carbon atoms, and one or two or more non-adjacent —CH 2 — in the alkyl group may each independently be substituted with —CH═CH—, —C≡—, —O—, —S—, —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 (one —CH 2 — or two or more non-adjacent —CH 2 — present in this group may be substituted with —O—)
(b) a 1,4-phenylene group (one —CH═ or two or more non-adjacent —CH═ present in this group may be substituted 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 (one —CH═ or two or more non-adjacent —CH═ present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with —N═), and
the group (a), the group (b), and the group (c) may each independently be 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 independently represent 0, 1, 2, or 3, provided that n N11 +n N12 , n N21 +n N22 , and n N31 +n N32 are each independently 1, 2, or 3; and
in a case where n N11 and/or n N12 is 2 or 3 and a plurality with respect to each of A N11 , A N12 , Z N11 , and Z N12 , is present, the groups or bonds may be the same or different, in a case where n N21 and/or n N22 is 2 or 3 and a plurality with respect to A N21 , A N22 , Z N21 , and Z N22 , the groups or bonds may be the same or different, and in a case where n N31 and/or n N32 is 2 or 3 and a plurality with respect to each of A N31 , A N32 , Z N31 , and Z N32 is present, the plural groups or bonds may be the same or different.

6. The liquid crystal composition according to claim 5 ,
wherein, in General Formula (N-1), A N11 is a trans 1,4-cyclohexylene group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, a 3,5-difluoro-1,4-phenylene group, a 2,3-difluoro-1,4-phenylene group, a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, Z N11 is —OCH 2 —, —CH 2 O—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, or a single bond, n N11 is 1, 2, or 3, and n N12 is 0.

7. The liquid crystal composition according to claim 5 ,
wherein, in General Formula (N-1), A N11 and A N12 are a trans 1,4-cyclohexylene group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo[2.2.2]octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, Z N11 and Z N12 are —OCH 2 —, —CH 2 O—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, or a single bond, and n N11 and n N12 each are 1 or 2.

8. The liquid crystal composition according to claim 5 ,
wherein the total content of General Formulas (N-1), (N-2), and (N-3) is from 10% to 90% by mass.

9. The liquid crystal composition according to claim 1 , further comprising:
at least one compound selected from compounds represented by General Formula (L):

wherein R L1 and R L2 each independently represent an alkyl group having 1 to 10 carbon atoms, and one or two or more non-adjacent —CH 2 — in the alkyl group may each independently be substituted with —CH═CH—, —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 (one —CH 2 — or two or more non-adjacent —CH 2 — present in this group may be substituted with —O—),
(b) a 1,4-phenylene group (one —CH═ or two or more non-adjacent —CH═ present in this group may be substituted 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 (one —CH═ or two or more non-adjacent —CH═ present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with —N═), and
the group (a), the group (b), and the group (c) may each independently be 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 —

Assignees

• Dainippon Ink & Chemicals

Inventors

• Sudo Go
• Hirata Shinichi

Classifications

• C09K19/322

  Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring · CPC title

• C09K19/542

  Macromolecular compounds · CPC title

• C09K2019/3009

  Cy-Ph · CPC title

• C09K19/3066

  in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers · CPC title

• C09K19/3028

  in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds · CPC title