US 12,473,492 B2
Compound, liquid crystal composition, and liquid crystal display element, sensor, liquid crystal lens, optical communication device, and antenna using liquid crystal composition
Mika Takasaki, Saitama (JP); Takaya Ikeuchi, Saitama (JP); Megumi Uzawa, Saitama (JP); Noriyuki Sugiyama, Saitama (JP); Go Sudo, Saitama (JP); Masanao Hayashi, Saitama (JP); and Shinichi Hirata, Saitama (JP)
Assigned to DIC Corporation, Tokyo (JP)
Appl. No. 18/578,710
Filed by DIC Corporation, Tokyo (JP)
PCT Filed Jul. 7, 2022, PCT No. PCT/JP2022/026898
§ 371(c)(1), (2) Date Jan. 11, 2024,
PCT Pub. No. WO2023/032466, PCT Pub. Date Mar. 9, 2023.
Claims priority of application No. 2021-143083 (JP), filed on Sep. 2, 2021.
Prior Publication US 2024/0336843 A1, Oct. 10, 2024
Int. Cl. G02F 1/1333 (2006.01); C09K 19/18 (2006.01); C09K 19/34 (2006.01)
CPC C09K 19/18 (2013.01) [C09K 19/3491 (2013.01); C09K 2019/181 (2013.01); C09K 2019/183 (2013.01); C09K 2219/11 (2013.01)] 18 Claims
 
1. A liquid crystal composition comprising at least one compound represented by general formula (i):

OG Complex Work Unit Chemistry
in general formula (i),
Ri1 represents an alkynyl group represented by formula (Ri1-A):

OG Complex Work Unit Chemistry
in general formula (Ri1-A), Ri1A represents an alkyl group having 1 to 18 carbon atoms,
at least one —CH2— in the alkyl group is optionally substituted with —O—, —S—, —CO—, and/or —CS—,
at least one —CH2—CH2— in the alkyl group is optionally substituted with —CO—O—, —O—CO—, —CO—S—, —S—CO—, —CO—NH—, —NH—CO—, —CH═CH—, —CF═CF—, and/or —C≡C—,
at least one —CH2—CH2—CH2— in the alkyl group is optionally substituted with —O—CO—O—, and
at least one hydrogen atom in the alkyl group is optionally substituted with a halogen atom,
where oxygen atoms are not directly bonded to each other, and
black dot represents a bond with Ai1,
Ai1 represents a group selected from the group consisting of the following groups (b), (c), and (d):
(b) a 1,4-phenylene group, wherein one —CH═ or two or more —CH═'s in this group are optionally substituted with —N═,
(c) a 1,4-cyclohexenylene group, a bicyclo[2.2.2]octane-1,4-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, a decahydronaphthalene-2,6-diyl group, an anthracene-2,6-diyl group, an anthracene-1,4-diyl group, an anthracene-9,10-diyl group, a phenanthrene-2,7-diyl group, wherein one —CH═ or two or more —CH═'s in the naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, or phenanthrene-2,7-diyl group are optionally substituted with —N═, and
(d) a thiophene-2,5-diyl group, a benzothiophene-2,5-diyl group, a benzothiophene-2,6-diyl group, a dibenzothiophene-3,7-diyl group, a dibenzothiophene-2,6-diyl group, a thieno[3,2-b]thiophene-2,5-diyl group, a benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group, wherein one —CH═ or two or more non-adjacent —CH═'s in this group are optionally substituted with —N═,
Ai2 and Ai3 each independently represent a group selected from the group consisting of the following groups (a), (b), (c), and (d):
(a) a 1,4-cyclohexylene group, wherein one —CH2— or two or more non-adjacent —CH2—'s in this group are optionally substituted with —O— and/or —S—,
(b) a 1,4-phenylene group, wherein one —CH═ or two or more —CH═'s in this group are optionally substituted with —N═,
(c) a 1,4-cyclohexenylene group, a bicyclo[2.2.2]octane-1,4-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, a decahydronaphthalene-2,6-diyl group, an anthracene-2,6-diyl group, an anthracene-1,4-diyl group, an anthracene-9,10-diyl group, a phenanthrene-2,7-diyl group, wherein one —CH═ or two or more —CH═'s in the naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 5,6,7,8-tetrahydronaphthalene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,4-diyl group, anthracene-9,10-diyl group, or phenanthrene-2,7-diyl group are optionally substituted with —N═, and
(d) a thiophene-2,5-diyl group, a benzothiophene-2,5-diyl group, a benzothiophene-2,6-diyl group, a dibenzothiophene-3,7-diyl group, a dibenzothiophene-2,6-diyl group, a thieno[3,2-b]thiophene-2,5-diyl group, a benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group, wherein one —CH═ or two or more non-adjacent —CH═'s in this group are optionally substituted with —N═,
wherein
at least one hydrogen atom in Ai1, Ai2, and Ai3 is optionally substituted with a substituent Si1,
the substituent Si1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms,
at least one —CH2— in the alkyl group is optionally substituted with —O—, —S—, and/or —CO—,
at least one —CH2—CH2— in the alkyl group is optionally substituted with —CH═CH—, —CF═CF—, —C≡C—, —CO—O—, —O—CO—, —CO—S—, —S—CO—, —CO—NH—, and/or —NH—CO—,
at least one —CH2—CH2—CH2— in the alkyl group is optionally substituted with —O—CO—O—, and
at least one hydrogen atom in the alkyl group is optionally substituted with a halogen atom,
where oxygen atoms are not directly bonded to each other,
a plurality of substituents Si1, if present, are optionally the same or different, and
Zi1 and Zi2 each independently represent a single bond or an alkylene group having 1 to 20 carbon atoms, wherein
at least one —CH2— in the alkylene group is optionally substituted with —O—, —CF2—, and/or —CO—, and
at least one —CH2—CH2— in the alkylene group is optionally substituted with —CH2—CH(CH3)—, —CH(CH3)—CH2—, —CH═CH—, —CF═CF—, —CH═C(CH3)—, —C(CH3)═CH—, —CH═N—, —N═CH—, —N═N—, —C≡C—, —CO—O—, and/or —O—CO—,
where oxygen atoms are not directly bonded to each other, and
ni1 represents an integer of 1.