IP Library Granted Patent US 10,047,289
Granted Patent B2
US 10,047,289 · App. 15/035,354 · Granted Aug 14, 2018

Liquid crystal display device

Inventors: Shinji Ogawa (Kita-adachi-gun, JP); Yoshinori Iwashita (Kita-adachi-gun, JP)
Assignee: DIC CORPORATION
C09K19/3066C09K19/0403C09K19/3003C09K19/322C09K19/56G02F1/1337G02F1/1368G02F1/13439G02F1/133365G02F1/136286C09K2019/0448C09K2019/0466C09K2019/122C09K2019/123C09K2019/301C09K2019/3004C09K2019/3009C09K2019/3016C09K2019/3019C09K2019/3021G02F2001/133738G02F2201/121G02F2201/123G02F2202/10
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Quick Facts
Patent No.
US 10,047,289
App. No.
15/035,354
Granted
Aug 14, 2018
Kind
B2
Abstract

Provided is a liquid crystal display device including first and second opposing substrates, a liquid crystal layer containing a liquid crystal composition between the first and second substrates, a plurality of gate lines and data lines arranged in a matrix on the first substrate, thin-film transistors disposed at intersections of the gate lines and the data lines, and pixel electrodes that are driven by the transistors and that are made of a transparent conductive material. Each thin-film transistor includes a gate electrode, an oxide semiconductor layer disposed over the gate electrode with an insulating layer therebetween, and source and drain electrodes electrically connected to the oxide semiconductor layer. The liquid crystal composition contains at least one compound selected from the group consisting of compounds represented by general formulas (LC1) and (LC2) and at least one compound selected from the group consisting of compounds represented by general formulas (II-a) to (II-f).

Claims (89)

1. A liquid crystal display device comprising:

first and second opposing substrates;

a liquid crystal layer comprising a liquid crystal composition between the first and second substrates;

a plurality of gate lines and data lines arranged in a matrix on the first substrate;

thin-film transistors disposed at intersections of the gate lines and the data lines; and

pixel electrodes that are driven by the transistors and that comprise a transparent conductive material,

each thin-film transistor comprising a gate electrode, an oxide semiconductor layer disposed over the gate electrode with an insulating layer therebetween, and source and drain electrodes electrically connected to the oxide semiconductor layer,

wherein formula (LC-I) is expressed as

in which R 31 is an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, an alkenyl group of 2 to 10 carbon atoms, or an alkenyloxy group of 2 to 10 carbon atoms,

each of M 31 to M 33 represents one of following structures,

M 34 represents

in which X 31 and X 32 are each independently hydrogen or fluorine, and Y 31 is fluorine, chlorine, cyano, —CF 3 , —OCH 2 F, —OCHF 2 , or —OCF 3 ,

n 31 and n 32 are each independently 0, 1, or 2, with the proviso that n 31 +n 32 is 0, 1, or 2, wherein each occurrence of M 31 and M 33 , if present, may be the same or different, and n 33 is 0 or 1,

wherein the liquid crystal composition comprises:

at least one compound selected from the group consisting of compounds represented by general formula (LC-I) in which n 33 is 1;

at least one compound selected from the group consisting of compounds represented by general formula (LC-I) in which n 33 is 0;

at least one compound selected from the group consisting of compounds represented by general formula (II-b); and

optionally at least one compound selected from the group consisting of compounds represented by general formulas (II-a) and (II-c) to (II-f):

wherein R 19 to R 30 are each independently an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, or an alkenyl group of 2 to 10 carbon atoms; and X 21 is hydrogen or fluorine,

wherein the compounds represented by general formulas (II-a) to (II-f) are included in an amount of 5% to 80% by mass in the liquid crystal composition.

2. The liquid crystal display device according to claim 1 , wherein the oxide semiconductor layer comprises an oxide containing at least one element selected from In, Ga, Zn, and Sn.

3. The liquid crystal display device according to claim 1 , wherein the oxide semiconductor layer comprises an oxide containing In, Ga, and Zn.

4. The liquid crystal display device according to claim 1 , wherein the liquid crystal layer further comprises a compound represented by general formula (LC):

wherein

R LC is an alkyl group of 1 to 15 carbon atoms, wherein one or more —CH 2 — groups in the alkyl group are optionally replaced with —O—, —CH═CH—, —CO—, —OCO—, —COO—, or —C≡C— such that no oxygen atoms are directly adjacent to each other, and one or more hydrogen atoms in the alkyl group are optionally replaced with halogen;

A LC1 and A LC2 are each independently a group selected from the group consisting of

(a) trans-1,4-cyclohexylene (wherein one or more non-adjacent —CH 2 — groups present in the group are optionally replaced with oxygen or sulfur),

(b) 1,4-phenylene (wherein one or more non-adjacent —CH═ groups present in the group are optionally replaced with nitrogen), and

(c) 1,4-bicyclo(2.2.2)octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and chromane-2,6-diyl,

wherein one or more hydrogen atoms present in groups (a), (b), and (c) are each optionally replaced with fluorine, chlorine, —CF 3 , or —OCF 3 ;

Z LC is a single bond, —CH═CH—, —CF═CF—, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, —COO—, or —OCO—;

Y LC is hydrogen, fluorine, chlorine, cyano, or an alkyl group of 1 to 15 carbon atoms, wherein one or more —CH 2 — groups in the alkyl group are optionally replaced with —O—, —CH═CH—, —CO—, —OCO—, —COO—, —CF 2 O—, or —OCF 2 — such that no oxygen atoms are directly adjacent to each other, and one or more hydrogen atoms in the alkyl group are optionally replaced with halogen; and

a is an integer of 1 to 4, wherein if a is 2, 3, or 4, each occurrence of A LC1 may be the same or different, and each occurrence of Z LC may be the same or different,

with the proviso that compounds represented by general formulas (LC1), (LC2), and (II-a) to (II-f) are excluded.

5. The liquid crystal display device according to claim 1 , wherein the liquid crystal layer further comprises a polymer of a liquid crystal composition comprising at least one polymerizable compound selected from the group consisting of:

polymerizable compounds represented by general formula (VI):

wherein X 3 is hydrogen or methyl; Sp 3 is a single bond, an alkylene group of 1 to 8 carbon atoms, or —O—(CH 2 ) t — (wherein t is an integer of 2 to 7, and the oxygen atom is linked to the aromatic ring); V is a linear or branched polyvalent alkylene group of 2 to 20 carbon atoms or a polyvalent cyclic substituent of 5 to 30 carbon atoms, wherein the alkylene group in the polyvalent alkylene group is optionally substituted with oxygen such that no oxygen atoms are adjacent to each other and is optionally substituted with an alkyl group of 5 to 20 carbon atoms (wherein the alkylene group in the group is optionally substituted with oxygen such that no oxygen atoms are adjacent to each other) or a cyclic substituent; and W is hydrogen, halogen, or an alkylene group of 1 to 8 carbon atoms; and

polymerizable compounds represented by general formula (V):

wherein X 1 and X 2 are each independently hydrogen or methyl; Sp 1 and Sp 2 are each independently a single bond, an alkylene group of 1 to 8 carbon atoms, or —O—(CH 2 ) s — (wherein s is an integer of 2 to 7, and the oxygen atom is linked to the aromatic ring); U is a linear or branched polyvalent alkylene group of 2 to 20 carbon atoms or a polyvalent cyclic substituent of 5 to 30 carbon atoms, wherein the alkylene group in the polyvalent alkylene group is optionally substituted with oxygen such that no oxygen atoms are adjacent to each other and is optionally substituted with an alkyl group of 5 to 20 carbon atoms (wherein the alkylene group in the group is optionally substituted with oxygen such that no oxygen atoms are adjacent to each other) or a cyclic substituent; and k is an integer of 1 to 5.

6. The liquid crystal display device according to claim 1 , further comprising a common electrode comprising a transparent conductive material on the second substrate,

wherein the liquid crystal layer is homogeneously aligned when no voltage is applied.

7. The liquid crystal display device according to any claim 1 , further comprising:

common electrodes disposed on the first or second substrate and separated from the pixel electrodes; and

alignment layers that are disposed between the first and second substrates and the liquid crystal layer and in contact with the liquid crystal layer and that induce homogeneous alignment to the liquid crystal composition, the first and second substrates being transparent insulating substrates,

wherein the shortest path from the pixel electrodes to the common electrodes located close to the pixel electrodes comprises a component parallel to the first or second substrate.

8. The liquid crystal display device according to claim 1 , further comprising:

common electrodes disposed on the first substrate and separated from the pixel electrodes; and

alignment layers that are disposed between the first and second substrates and the liquid crystal layer and in contact with the liquid crystal layer and that induce homogeneous alignment to the liquid crystal composition,

wherein the shortest distance d between the common electrodes and the pixel electrodes located close to each other is shorter than the shortest distance G between the alignment layers.

9. The liquid crystal display device according to claim 1 , wherein the liquid crystal composition consists of:

said at least one compound selected from the group consisting of compounds represented by general formula (LC-I) in which n 33 is 1;

said at least one compound selected from the group consisting of compounds represented by general formula (LC-I) in which n 33 is 0;

said at least one compound selected from the group consisting of compounds represented by general formula (II-b);

optionally said at least one compound selected from the group consisting of compounds represented by general formulas (II-a) and (II-c) to (II-f), optionally a compound represented by general formula (LC):

wherein

R LC is an alkyl group of 1 to 15 carbon atoms, wherein one or more —CH 2 — groups in the alkyl group are optionally replaced with —O—, —CH═CH—, —CO—, —OCO—, —COO—, or —C≡C— such that no oxygen atoms are directly adjacent to each other, and one or more hydrogen atoms in the alkyl group are optionally replaced with halogen;

A LC1 and A LC2 are each independently a group selected from the group consisting of

(a) trans-1,4-cyclohexylene (wherein one or more non-adjacent —CH 2 — groups present in the group are optionally replaced with oxygen or sulfur),

(b) 1,4-phenylene (wherein one or more non-adjacent —CH═ groups present in the group are optionally replaced with nitrogen), and

(c) 1,4-bicyclo(2.2.2)octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and chromane-2,6-diyl,

wherein one or more hydrogen atoms present in groups (a), (b), and (c) are each optionally replaced with fluorine, chlorine, —CF 3 , or —OCF 3 ;

Z LC is a single bond, —CH═CH—, —CF═CF—, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, —COO—, or —OCO—;

Y LC is hydrogen, fluorine, chlorine, cyano, or an alkyl group of 1 to 15 carbon atoms, wherein one or more —CH 2 — groups in the alkyl group are optionally replaced with —O—, —CH═CH—, —CO—, —OCO—, —COO—, —CF 2 O—, or —OCF 2 — such that no oxygen atoms are directly adjacent to each other, and one or more hydrogen atoms in the alkyl group are optionally replaced with halogen; and

a is an integer of 1 to 4, wherein if a is 2, 3, or 4, each occurrence of A LC1 may be the same or different, and each occurrence of Z LC may be the same or different,

with the proviso that compounds represented by general formulas (LC-I) and (II-a) to (II-f) are excluded; and

optionally at least one polymerizable compound selected from the group consisting of polymerizable compounds represented by general formula (VI) and polymerizable compounds represented by general formula (V):

wherein X 3 is hydrogen or methyl; Sp 3 is a single bond, an alkylene group of 1 to 8 carbon atoms, or —O—(CH 2 ) t — (wherein t is an integer of 2 to 7, and the oxygen atom is linked to the aromatic ring); V is a linear or branched polyvalent alkylene group of 2 to 20 carbon atoms or a polyvalent cyclic substituent of 5 to 30 carbon atoms, wherein the alkylene group in the polyvalent alkylene group is optionally substituted with oxygen such that no oxygen atoms are adjacent to each other and is optionally substituted with an alkyl group of 5 to 20 carbon atoms (wherein the alkylene group in the group is optionally substituted with oxygen such that no oxygen atoms are adjacent to each other) or a cyclic substituent; and W is hydrogen, halogen, or an alkylene group of 1 to 8 carbon atoms; and

wherein X 1 and X 2 are each independently hydrogen or methyl; Sp 1 and Sp 2 are each independently a single bond, an alkylene group of 1 to 8 carbon atoms, or —O—(CH 2 ) s — (wherein s is an integer of 2 to 7, and the oxygen atom is linked to the aromatic ring); U is a linear or branched polyvalent alkylene group of 2 to 20 carbon atoms or a polyvalent cyclic substituent of 5 to 30 carbon atoms, wherein the alkylene group in the polyvalent alkylene group is optionally substituted with oxygen such that no oxygen atoms are adjacent to each other and is optionally substituted with an alkyl group of 5 to 20 carbon atoms (wherein the alkylene group in the group is optionally substituted with oxygen such that no oxygen atoms are adjacent to each other) or a cyclic substituent; and k is an integer of 1 to 5.

10. The liquid crystal display device according to claim 1 , wherein the liquid crystal composition consists of:

said at least one compound selected from the group consisting of compounds represented by general formula (LC-I) in which n 33 is 1;

said at least one compound selected from the group consisting of compounds represented by general formula (LC-I) in which n 33 is 0;

said at least one compound selected from the group consisting of compounds represented by general formula (II-b);

optionally said at least one compound selected from the group consisting of compounds represented by general formulas (II-a) and (II-c) to (II-f),

optionally a compound represented by general formula (LC):

wherein

R LC is an alkyl group of 1 to 15 carbon atoms, wherein one or more —CH 2 — groups in the alkyl group are optionally replaced with —O—, —CH═CH—, —CO—, —OCO—, —COO—, or —C≡C— such that no oxygen atoms are directly adjacent to each other, and one or more hydrogen atoms in the alkyl group are optionally replaced with halogen;

A LC1 and A LC2 are each independently a group selected from the group consisting of

(a) trans-1,4-cyclohexylene (wherein one or more non-adjacent —CH 2 — groups present in the group are optionally replaced with oxygen or sulfur),

(b) 1,4-phenylene (wherein one or more non-adjacent —CH═ groups present in the group are optionally replaced with nitrogen), and

(c) 1,4-bicyclo(2.2.2)octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and chromane-2,6-diyl,

wherein one or more hydrogen atoms present in groups (a), (b), and (c) are each optionally replaced with fluorine, chlorine, —CF 3 , or —OCF 3 ;

Z LC is a single bond, —CH═CH—, —CF═CF—, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, —COO—, or —OCO—;

Y LC is hydrogen, fluorine, chlorine, cyano, or an alkyl group of 1 to 15 carbon atoms, wherein one or more —CH 2 — groups in the alkyl group are optionally replaced with —O—, —CH═CH—, —CO—, —OCO—, —COO—, —CF 2 O—, or —OCF 2 — such that no oxygen atoms are directly adjacent to each other, and one or more hydrogen atoms in the alkyl group are optionally replaced with halogen; and

a is an integer of 1 to 4, wherein if a is 2, 3, or 4, each occurrence of A LC1 may be the same or different, and each occurrence of Z LC may be the same or different,

with the proviso that compounds represented by general formulas (LC-I) and (II-a) to (II-f) are excluded; and

optionally at least one polymerizable compound represented by general formula (VI):

wherein X 3 is hydrogen or methyl; Sp 3 is a single bond, an alkylene group of 1 to 8 carbon atoms, or —O—(CH 2 ) t — (wherein t is an integer of 2 to 7, and the oxygen atom is linked to the aromatic ring); V is a linear or branched polyvalent alkylene group of 2 to 20 carbon atoms or a polyvalent cyclic substituent of 5 to 30 carbon atoms, wherein the alkylene group in the polyvalent alkylene group is optionally substituted with oxygen such that no oxygen atoms are adjacent to each other and is optionally substituted with an alkyl group of 5 to 20 carbon atoms (wherein the alkylene group in the group is optionally substituted with oxygen such that no oxygen atoms are adjacent to each other) or a cyclic substituent; and W is hydrogen, halogen, or an alkylene group of 1 to 8 carbon atoms.

11. The liquid crystal display device according to claim 1 , wherein assuming that a liquid crystal display device without comprising the liquid crystal composition has a maximum transmittance of 100%, the liquid crystal display device comprising the liquid crystal composition has a maximum transmittance of 88.9% or more.

12. The liquid crystal display device according to claim 11 , wherein the liquid crystal display device comprising the liquid crystal composition has the maximum transmittance from 88.9% to 89.0%.

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 May 25, 2018
From: OGAWA, SHINJI; IWASHITA, YOSHINORI
To: DIC CORPORATION
Reel/Frame 045903/0649 →
Priority Claims (1)
JP 2013-233958 · Nov 12, 2013 · national
Continuity (1)
Related Publication 20160289560A1 · Oct 6, 2016