CN111183205B - Liquid crystal composition and liquid crystal display element - Google Patents

Liquid crystal composition and liquid crystal display element Download PDF

Info

Publication number
CN111183205B
CN111183205B CN201880065166.8A CN201880065166A CN111183205B CN 111183205 B CN111183205 B CN 111183205B CN 201880065166 A CN201880065166 A CN 201880065166A CN 111183205 B CN111183205 B CN 111183205B
Authority
CN
China
Prior art keywords
liquid crystal
crystal composition
mass
compound represented
general formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201880065166.8A
Other languages
Chinese (zh)
Other versions
CN111183205A (en
Inventor
须藤豪
大石晴己
谷口士朗
栗泽和树
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
Original Assignee
DIC Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by DIC Corp filed Critical DIC Corp
Publication of CN111183205A publication Critical patent/CN111183205A/en
Application granted granted Critical
Publication of CN111183205B publication Critical patent/CN111183205B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/16Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/18Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/08Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/32Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/34Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/44Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells

Landscapes

  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

The object of the present invention is to provide a liquid crystal composition having a negative Δε and T NI High, gamma 1 Small, delta n large, K 11 Is small. Provided is a liquid crystal display element corresponding to a high-definition VA type, PSA type, PSVA type or the like, which has a high response speed, a high VHR and a high transmittance and has no or little display defects by using the liquid crystal composition. The liquid crystal display element is suitable for liquid crystal televisions, smart phones, notebook computers, tablet computers, vehicle-mounted LCD, PID (public information display ) and the like. The liquid crystal composition of the present invention solves the above problems by a liquid crystal composition containing a compound represented by the general formula (S1), the general formula (S2) and the general formula (S3).

Description

Liquid crystal composition and liquid crystal display element
Technical Field
The present invention relates to a liquid crystal composition and a liquid crystal display element using the same.
Background
Liquid crystal display elements are used for various household electrical appliances such as watches and calculators, industrial measurement equipment, automotive panels, mobile phones, smart phones, notebook computers, tablet computers, televisions, and the like. As a liquid crystal display method, a typical liquid crystal display method includes: TN (twisted nematic), STN (super twisted nematic), GH (guest-host), IPS (in-plane switching) and FFS (fringe field switching technique), OCB (optically compensated birefringence), ECB (electrically controlled birefringence), VA (vertical alignment), CSH (color supervertical) and FLC (ferroelectric liquid crystal) and the like. The driving method may be: static driving, multiplex driving, simple matrix method, active Matrix (AM) method driven by TFT (thin film transistor), TFD (thin film diode) or the like. Among these display modes, IPS type, FFS type, ECB type, VA type, CSH type, and the like have a characteristic of a liquid crystal composition exhibiting a negative value using dielectric anisotropy (Δ∈).
Among these, VA-type, PSA-type, and FFS-type display systems using AM driving are used in, for example, liquid crystal televisions, monitors, smartphones, and tablet computers, and further applications as outdoor display elements are being developed from the viewpoint of optimal viewing angle, transmittance, power consumption, and the like.
As a liquid crystal composition having negative Δ∈, a liquid crystal composition using the following liquid crystal compounds (a) and (B) having a 2, 3-difluorophenylene skeleton is disclosed (refer to patent document 1).
[ chemical 1]
Figure BDA0002440322440000011
The liquid crystal composition uses the liquid crystal compounds (C) and (D) as the liquid crystal compound having a Δ∈ of substantially 0, but the liquid crystal composition has not yet achieved sufficiently low viscosity for liquid crystal compositions requiring high-speed response such as liquid crystal televisions.
[ chemical 2]
Figure BDA0002440322440000021
On the other hand, there have been disclosed liquid crystal compositions using a liquid crystal compound (E), which introduce a liquid crystal composition having a small refractive index anisotropy Δn in combination with the above-mentioned liquid crystal compound (D) (refer to patent document 2) and a liquid crystal composition to which a liquid crystal compound (F) is added in order to improve the response speed (refer to patent document 3). However, it is known that: the liquid crystal compound having an alkenyl group such as the liquid crystal compound (F) causes a decrease in reliability of the liquid crystal display element, specifically, a decrease in Voltage Holding Ratio (VHR) is liable to occur.
[ chemical 3]
Figure BDA0002440322440000022
In addition, a liquid crystal composition using a liquid crystal compound (G) and a liquid crystal compound (F) has been disclosed (refer to patent document 4), but a faster response speed is required.
[ chemical 4]
Figure BDA0002440322440000023
However, in the present day of the development of high definition of liquid crystal display elements, further improvement of transmittance is regarded as an important point, and a liquid crystal composition for providing a liquid crystal display element satisfying the same is being demanded.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 8-104869
Patent document 2: european patent application publication No. 0474062
Patent document 3: japanese patent laid-open No. 2006-037054
Patent document 4: japanese patent laid-open No. 2001-354967
Disclosure of Invention
Problems to be solved by the invention
The invention provides a liquid crystal composition capable of achieving a fast response speed, a high VHR and a high transmittance, and a liquid crystal display element of VA type, PSA type, PSVA type and the like using the same.
Means for solving the problems
As a result of intensive studies, the present inventors have found that the above problems can be solved by a liquid crystal composition comprising a combination of compounds having specific chemical structures, and have completed the present invention.
ADVANTAGEOUS EFFECTS OF INVENTION
The liquid crystal composition delta epsilon of the invention is negative and T NI High, gamma 1 Small, delta n large, K 11 Is small. A liquid crystal display element corresponding to a high definition VA type, PSA type, PSVA type or the like, which has a high response speed, a high VHR and a high transmittance and is free from or little in display failure by using the liquid crystal composition, can be provided. The liquid crystal display element is suitable for liquid crystal televisions, smart phones, notebook computers, tablet computers, vehicle-mounted LCD, PID (public information display ) and the like.
Drawings
Fig. 1 is a graph showing the effects of examples 1 to 3.
Detailed Description
The present invention is a liquid crystal composition containing 1 or 2 or more compounds represented by the general formula (S1), 1 or 2 or more compounds represented by the general formula (S2), and 1 or 2 or more compounds represented by the general formula (S3), wherein Δε is negative; further, the present invention is a liquid crystal display element using the above liquid crystal composition,
[ chemical 5]
Figure BDA0002440322440000031
(wherein R is S1 R is R S2 Each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, R S3 R is R S5 Each independently represents 1 carbon atomAn alkyl group of up to 8, an alkoxy group of up to 1 to 8 carbon atoms, or an alkenyl group of up to 2 to 8 carbon atoms, or an alkenyloxy group of up to 2 to 8 carbon atoms, R S4 R is R S6 Each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms).
The content of the compound of the general formula (S1) in the liquid crystal composition of the present invention is preferably 10 mass%, more preferably 15 mass%, more preferably 20 mass%, more preferably 25 mass%, more preferably 30 mass%, more preferably 35 mass%, and is preferably 50 mass%, more preferably 45 mass%, more preferably 40 mass%, more preferably 35 mass%, more preferably 30 mass%, as the lower limit value.
The content of the compound of the general formula (S2) in the liquid crystal composition of the present invention is preferably 10 mass%, more preferably 12 mass%, still more preferably 14 mass%, still more preferably 15 mass%, still more preferably 20 mass%, still more preferably 25 mass%, and is preferably 40 mass%, more preferably 35 mass%, still more preferably 30 mass% as the lower limit value.
The content of the compound of the general formula (S3) in the liquid crystal composition of the present invention is preferably 10 mass%, more preferably 15 mass%, more preferably 17 mass%, more preferably 19 mass%, more preferably 20 mass%, more preferably 24 mass%, and is preferably 40 mass%, more preferably 35 mass%, more preferably 30 mass% as the lower limit value.
The compound represented by the general formula (S1) is preferably a compound represented by the formula (S1-1), the formula (S1-2) or the formula (S1-3).
[ chemical 6]
Figure BDA0002440322440000041
The liquid crystal composition of the present invention particularly preferably contains a compound represented by the formula (S1-1) as the compound represented by the general formula (S1).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S1-2) as the compound represented by the general formula (S1).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S1-3) as the compound represented by the general formula (S1).
The liquid crystal composition of the present invention particularly preferably contains a compound represented by the formula (S1-1) and a compound represented by the formula (S1-2) as the compound represented by the general formula (S1).
The liquid crystal composition of the present invention particularly preferably contains a compound represented by the formula (S1-1) and a compound represented by the formula (S1-3) as the compound represented by the general formula (S1).
The liquid crystal composition of the present invention may further contain a compound represented by the formula (S1-5) or the formula (S1-6).
[ chemical 7]
Figure BDA0002440322440000051
The compound represented by the general formula (S2) is preferably a compound represented by the formula (S2-1), the formula (S2-2), the formula (S2-3) or the formula (S2-4).
[ chemical 8]
Figure BDA0002440322440000052
The liquid crystal composition of the present invention particularly preferably contains a compound represented by the formula (S2-1) as the compound represented by the general formula (S2).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S2-2) as the compound represented by the general formula (S2).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S2-3) as the compound represented by the general formula (S2).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S2-4) as the compound represented by the general formula (S2).
The liquid crystal composition of the present invention further preferably contains a compound represented by the formula (S2-1) and a compound represented by the formula (S2-2) as the compound represented by the general formula (S2).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S2-1) and a compound represented by the formula (S2-3) as the compound represented by the general formula (S2).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S2-1) and a compound represented by the formula (S2-4) as the compound represented by the general formula (S2).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S2-3) and a compound represented by the formula (S2-4) as the compound represented by the general formula (S2).
The compound represented by the general formula (S3) is preferably a compound represented by the general formula (S3-1), the general formula (S3-2), the general formula (S3-3), or the general formula (S3-4).
[ chemical 9]
Figure BDA0002440322440000061
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S3-1) as the compound represented by the general formula (S3).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S3-2) as the compound represented by the general formula (S3).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S3-3) as the compound represented by the general formula (S3).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S3-4) as the compound represented by the general formula (S3).
The liquid crystal composition of the present invention further preferably contains a compound represented by the formula (S3-1) and a compound represented by the formula (S3-2) as the compound represented by the general formula (S3).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S3-1) and a compound represented by the formula (S3-3) as the compound represented by the general formula (S3).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S3-2) and a compound represented by the formula (S3-3) as the compound represented by the general formula (S3).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (S3-2) and a compound represented by the formula (S3-4) as the compound represented by the general formula (S3).
The liquid crystal composition of the present invention more preferably contains a compound represented by the formula (S3-1), a compound represented by the formula (S3-2), and a compound represented by the formula (S3-3) as the compound represented by the general formula (S3).
The liquid crystal composition of the present invention more preferably contains a compound represented by the formula (S3-1), a compound represented by the formula (S3-2), and a compound represented by the formula (S3-4) as the compound represented by the general formula (S3).
The liquid crystal composition of the present invention particularly preferably contains a compound represented by the formula (S3-1), a compound represented by the formula (S3-2), a compound represented by the formula (S3-3), and a compound represented by the formula (S3-4) as the compound represented by the general formula (S3).
The liquid crystal composition of the present invention may further contain 1 or 2 or more compounds selected from the group of compounds represented by the general formulae (N-02) and (N-04),
[ chemical 10]
Figure BDA0002440322440000081
(wherein R is 21 R is R 22 Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms, 1 of which groups is not adjacent to or above 2-CH 2 Can be independently and individually substituted by-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution, Z is Z 1 Respectively and independently represent a single bond, -CH 2 CH 2 -、-OCH 2 -、-CH 2 O-, -COO-, -OCO-, or-C.ident.C-, m each independently represents 1 or 2).
The compounds represented by the general formulae (N-02) and (N-04) have negative dielectric anisotropy (. DELTA.. Epsilon.) and their absolute values show values greater than 2. Here, Δε is the following value: a value extrapolated from a measured value of dielectric anisotropy of a composition obtained by adding the compound to a composition that is substantially dielectric neutral at 25 ℃.
R 21 Preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and still more preferably an alkyl group having 1 to 4 carbon atoms. Wherein Z is 1 When the compound represents a single bond or other than a single bond, R 21 Preferably an alkyl group having 1 to 3 carbon atoms.
R 22 Preferably an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and still more preferably an alkoxy group having 1 to 4 carbon atoms.
At R 21 R is R 22 In the case of an alkenyl group, a group represented by any one of the formulae (R1) to (R5) (the black dot in the formulae represents a carbon atom in the ring structure) is preferable, and the formula (R1) or the formula (R2) is preferable. In detail, when low rotational viscosity (γ1) is important, formula (R1) is preferable, and when high (T Ni ) Or a high elastic constant (K33), the formula (R2) is preferable.
[ chemical 11]
Figure BDA0002440322440000082
Z 1 Respectively and independently represent a single bond, -CH 2 CH 2 -、-OCH 2 -、-CH 2 O-、-COO-、-OCO-、-OCF 2 -、-CF 2 O-, -CH=CH-, -CF=CF-, or-C≡C-, preferably a single bond, -CH 2 CH 2 -、-OCH 2 -、-CH 2 O-, more preferably a single bond, -CH 2 CH 2 -or-CH 2 O-。
In the general formula (N-02), Z is preferable 1 Is a single bond, m is 1, R 21 Is alkyl of 2 to 4 carbon atoms, R 22 A compound which is an alkoxy group having 1 to 4 carbon atoms.
In the general formula (N-04), Z is preferable 1 is-CH 2 CH 2 -、R 21 Is alkyl of 1 to 4 carbon atoms, R 22 A compound which is an alkoxy group having 1 to 4 carbon atoms.
The fluorine atom of the compounds represented by the general formulae (N-02) and (N-04) may be substituted with a chlorine atom which is also a halogen group. Among them, the content of the compound substituted with a chlorine atom is preferably as small as possible, and more preferably not.
The hydrogen atoms of the rings of the compounds represented by the general formulae (N-02) and (N-04) may be further substituted with fluorine atoms or chlorine atoms. Among them, the content of the compound substituted with a chlorine atom is preferably as small as possible, and more preferably not.
The compound represented by the general formula (N-02) and (N-04) is preferably a compound having a negative Δε and an absolute value of more than 3.
The compound represented by the general formula (N-02) preferably contains 1 or 2 or more compounds selected from the group consisting of the compounds represented by the general formula (N-02-1), the general formula (N-02-2), and the general formula (N-02-3),
[ chemical 12]
Figure BDA0002440322440000091
(R 21 R is R 22 Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms, 1 of which groups is not adjacent to or above 2-CH 2 -may each be independently substituted by-ch=ch-, -c≡c-, -O-, -CO-, -COO-, or-OCO-.
R 21 Each independently is preferably an alkyl group having 1 to 4 carbon atoms, R 22 Alkoxy groups having 1 to 4 carbon atoms are preferable.
The liquid crystal composition of the present invention preferably further comprises a compound represented by the general formula (N-02-3).
As the compound represented by the general formula (N-04), 1 or 2 or more compounds represented by the general formula (N-04-1) may be contained,
[ chemical 13]
Figure BDA0002440322440000101
(R 21 R is R 22 Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms, 1 of which groups is not adjacent to or above 2-CH 2 -may each be independently substituted by-ch=ch-, -c≡c-, -O-, -CO-, -COO-, or-OCO-.
R in the formula (N-04-1) 21 Preferably an alkyl group having 1 to 4 carbon atoms, R 23 Alkoxy groups having 1 to 4 carbon atoms are preferable.
The liquid crystal composition of the present invention particularly preferably contains a compound represented by the general formula (N-04-1).
The preferable lower limit of the content of the compound represented by the general formula (N-02) is 0%, 1%, 5% and 10% relative to the total amount of the liquid crystal composition of the present invention, and the upper limit is 10% and 5% relative to the total amount of the liquid crystal composition of the present invention.
The preferable lower limit value of the content of the compound represented by the general formula (N-04) is 0%, 1%, 5% and 10% relative to the total amount of the liquid crystal composition of the present invention, and the upper limit value is 30%, 25%, 20%, 15%, 10% and 5% relative to the total amount of the liquid crystal composition of the present invention.
The liquid crystal composition of the present invention may further contain 1 or 2 or more compounds represented by the general formula (N-06).
[ chemical 14]
Figure BDA0002440322440000111
(wherein R is 21 R is R 22 The same meaning as described above is indicated. )
The liquid crystal composition of the present invention preferably does not contain the compound represented by the formula (N-06).
The liquid crystal composition of the present invention preferably does not contain a cyclohexene ring-containing compound.
The liquid crystal composition of the present invention contains 1 or 2 or more compounds selected from the group of compounds represented by the general formulae (NU-02) to (NU-07) as compounds having a Δε of substantially 0,
[ 15]
Figure BDA0002440322440000112
(wherein R is NU21 、R NU22 、R NU31 、R NU32 、R NU41 、R NU42 、R NU51 、R NU52 、R NU61 、R NU62 、R NU71 R is R NU72 Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms, 1 of which groups is not adjacent to or above 2-CH 2 -may each be independently substituted by-ch=ch-, -c≡c-, -O-, -CO-, -COO-, or-OCO-.
R NU21 、R NU22 、R NU31 、R NU32 、R NU41 、R NU42 、R NU51 、R NU52 、R NU61 、R NU62 、R NU71 R is R NU72 Each independently is preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-05) and the general formula (NU-02).
The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-05) and a compound represented by the general formula (NU-03).
The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-05) and the general formula (NU-04).
The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-05) and the general formula (NU-06).
The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-06) and the general formula (NU-07).
The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-02), the general formula (NU-03) and the general formula (NU-04).
The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-03), the general formula (NU-04) and the general formula (NU-05).
The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-03), the general formula (NU-04) and the general formula (NU-06).
The liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-03), the general formula (NU-05) and the general formula (NU-06).
The liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds selected from the group of compounds represented by the general formula (NU-02), the general formula (NU-03) and the general formula (NU-05).
The content of the compound represented by the general formula (NU-02) is preferably 0 to 30% by mass, more preferably 1 to 25% by mass, and still more preferably 1 to 20% by mass.
The content of the compound represented by the general formula (NU-03) is preferably 0 to 20% by mass, more preferably 1 to 20% by mass, and still more preferably 1 to 15% by mass.
The content of the compound represented by the general formula (NU-04) is preferably 0 to 20% by mass, more preferably 1 to 15% by mass, and still more preferably 1 to 10% by mass.
The content of the compound represented by the general formula (NU-05) is preferably 0 to 30% by mass, more preferably 1 to 25% by mass, and still more preferably 2 to 20% by mass.
The content of the compound represented by the general formula (NU-06) is preferably 0 to 20% by mass, more preferably 0 to 15% by mass, and still more preferably 1 to 10% by mass.
The content of the compound represented by the general formula (NU-07) is preferably 0 to 20% by mass, more preferably 0 to 15% by mass, and still more preferably 1 to 10% by mass.
The liquid crystal composition of the present invention particularly preferably contains a compound represented by the general formula (NU-05).
The liquid crystal composition of the present invention particularly preferably contains a compound represented by the general formula (NU-05) selected from the group of compounds represented by the formulas (NU-05-1) to (NU-05-10).
[ 16]
Figure BDA0002440322440000131
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-1).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-2).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-3).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-6).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-9).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-10).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-1) and a compound represented by the formula (NU-05-2).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-2) and a compound represented by the formula (NU-05-3).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-5) and a compound represented by the formula (NU-05-6).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-6) and a compound represented by the formula (NU-05-9).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-1), a compound represented by the formula (NU-05-2) and a compound represented by the formula (NU-05-3).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-1), a compound represented by the formula (NU-05-2) and a compound represented by the formula (NU-05-6).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-2), a compound represented by the formula (NU-05-3) and a compound represented by the formula (NU-05-6).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-1), a compound represented by the formula (NU-05-6) and a compound represented by the formula (NU-05-9).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-05-2), a compound represented by the formula (NU-05-6) and a compound represented by the formula (NU-05-9).
The liquid crystal composition of the present invention particularly preferably contains a compound represented by the general formula (NU-03) selected from the group of compounds represented by the formulas (NU-03-1) to (NU-03-2).
[ chemical 17]
Figure BDA0002440322440000151
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-03-1).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-03-2).
The liquid crystal composition of the present invention preferably contains a compound represented by the formula (NU-03-1) and a compound represented by the formula (NU-03-2).
The liquid crystal composition of the present invention particularly preferably contains a compound represented by the general formula (NU-02) as a compound selected from the group of compounds represented by the formulas (NU-02-1) to (NU-02-2).
[ chemical 18]
Figure BDA0002440322440000152
The liquid crystal composition of the present invention particularly preferably contains a compound represented by the formula (NU-02-1).
The liquid crystal composition of the present invention is a liquid crystal composition having negative delta epsilon, and contains a compound having negative delta epsilon and an absolute value of 3 or more. The compounds having negative Δε and an absolute value of 3 or more have electron-withdrawing groups such as 2 or more halogen atoms and cyano groups in the short axis direction of the molecule, and particularly have electron-withdrawing groups on adjacent carbon atoms in the same aromatic ring. The compounds having negative Δε and an absolute value of 3 or more are often compounds having structures represented by formulas (NS-1) to (NS-4) in the molecule.
In the liquid crystal composition of the present invention, the lower limit value of the total content of the compounds represented by the general formulae (S2) and (S3) in the total amount of the compounds having a negative Δ∈ and an absolute value of 3 or more is preferably 90 mass%, preferably 92 mass%, preferably 94 mass%, preferably 96 mass%, preferably 98 mass%, preferably 99 mass%, preferably substantially 100 mass% excluding additives such as antioxidants and polymerizable compounds, and the upper limit value is preferably substantially 100 mass% excluding additives such as antioxidants and polymerizable compounds.
In the liquid crystal composition of the present invention, the lower limit value of the total content of the compounds represented by the general formulae (S2) and (S3) in the total amount of the compounds having the structures represented by the formulae (NS-1) to (NS-4) in the molecule is preferably 90% by mass, more preferably 92% by mass, still more preferably 94% by mass, still more preferably 96% by mass, still more preferably 98% by mass, still more preferably 99% by mass, and still more preferably substantially 100% by mass excluding additives such as antioxidants and polymerizable compounds, and the upper limit value is preferably substantially 100% by mass excluding additives such as antioxidants and polymerizable compounds.
[ chemical 19]
Figure BDA0002440322440000161
(wherein, at the same time, other structures are combined.)
The liquid crystal composition of the present invention contains the compound represented by the general formula (S1), the compound represented by the general formula (S2), and the compound represented by the general formula (S3), and preferably further contains 1 or 2 or more compounds selected from the group of compounds represented by the general formulae (NU-02) to (NU-07), and the total upper limit of the content thereof is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, and the total lower limit of the content thereof is preferably 80 mass%, 82 mass%, 84 mass%, 86 mass%, 88 mass%, 90 mass%, 92 mass%, 94 mass%, 96 mass%, 98 mass%, 99 mass%, 100 mass% with respect to the entire liquid crystal composition.
The liquid crystal composition of the invention is the following liquid crystal composition, namely: the composition comprises 10 to 50 mass% of a compound represented by the general formula (S1), 14 to 34 mass% of a compound represented by the general formula (S2), 19 to 39 mass% of a compound represented by the general formula (S3), 3 to 30 mass% of a compound represented by the general formula (NU-05), 1 to 20 mass% of a compound represented by the general formula (NU-03-1), and 0 to 20 mass% of a compound represented by the general formula (NU-03-2), wherein the total of the components is 85 to 100 mass% and the dielectric anisotropy (delta epsilon) is negative.
The liquid crystal composition of the invention is the following liquid crystal composition, namely: the composition comprises 10 to 50 mass% of a compound represented by the general formula (S1), 14 to 34 mass% of a compound represented by the general formula (S2), 19 to 39 mass% of a compound represented by the general formula (S3), 3 to 30 mass% of a compound represented by the general formula (NU-05), 1 to 20 mass% of a compound represented by the general formula (NU-03-1), and 0 to 20 mass% of a compound represented by the general formula (NU-03-2), wherein the total of the components is 90 to 100 mass% and the dielectric anisotropy (delta epsilon) is negative.
The liquid crystal composition of the invention is the following liquid crystal composition, namely: the composition comprises 10 to 50 mass% of a compound represented by the general formula (S1), 14 to 34 mass% of a compound represented by the general formula (S2), 19 to 39 mass% of a compound represented by the general formula (S3), 3 to 30 mass% of a compound represented by the general formula (NU-05), 1 to 20 mass% of a compound represented by the general formula (NU-03-1), 0 to 20 mass% of a compound represented by the general formula (NU-03-2), 1 to 25 mass% of a compound represented by the general formula (NU-02-1), and the total of the components is 85 to 100 mass% and the dielectric anisotropy (Deltaε) is negative.
The liquid crystal composition of the invention is the following liquid crystal composition, namely: the composition comprises 10 to 50 mass% of a compound represented by the general formula (S1), 14 to 34 mass% of a compound represented by the general formula (S2), 19 to 39 mass% of a compound represented by the general formula (S3), 3 to 30 mass% of a compound represented by the general formula (NU-05), 1 to 20 mass% of a compound represented by the general formula (NU-03-1), 0 to 20 mass% of a compound represented by the general formula (NU-03-2), 1 to 25 mass% of a compound represented by the general formula (NU-02-1), and the total of the components is 90 to 100 mass% and the dielectric anisotropy (Deltaε) is negative.
The liquid crystal composition of the present invention may contain 1 or 2 or more polymerizable compounds.
The liquid crystal composition of the present invention may contain 1 or 2 or more polymerizable compounds represented by the general formula (RM),
[ chemical 20]
Figure BDA0002440322440000181
(wherein R is 101 To R 112 Respectively and independently represent P 13 -S 13 -, a hydrogen atom, a fluorine atom, an alkyl group having 1 to 18 carbon atoms or an alkoxy group, the hydrogen atom in the group being optionally substituted by a fluorine atom, n RM Represents 0 or 1, P 11 、P 12 P 13 Each independently represents a group selected from the group consisting of the formulae (Re-1) to (Re-9), S 11 、S 12 S and S 13 Each independently represents a single bond or an alkylene group having 1 to 15 carbon atoms, 1-CH in the alkylene group 2 -or non-contiguous more than 2-CH 2 -can be substituted by-O-, -OCO-or-COO-in such a way that the oxygen atoms are not directly adjacent, in the presence of a plurality of P' s 13 S and S 13 In the case of (2), may be the same or different,
[ chemical 21]
Figure BDA0002440322440000182
(wherein R is 11 、R 12 、R 13 、R 14 R is R 15 Each independently represents any one of an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, m r5 、m r7 、n r5 N is as follows r7 Each independently represents 0, 1, or 2)).
The liquid crystal composition containing the polymerizable compound represented by the general formula (RM) is suitable for the production of PSA-type or PSVA-type liquid crystal display elements. It is also suitable for the case of manufacturing NPS type or PI-less type liquid crystal display elements.
In the general formula (RM), R 101 、R 102 、R 103 、R 104 、R 105 、R 106 、R 107 R is R 108 Respectively and independently represent P 13 -S 13 Any one of an alkyl group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, a fluorine atom or a hydrogen atom, and in the case of an alkyl group and an alkoxy group, the number of carbon atoms is preferably 1 to 16, more preferably 1 to 10, still more preferably 1 to 4, particularly preferably 1. The alkyl group and the alkoxy group may be linear or branched, and are preferably linear.
In the general formula (RM), R 101 、R 102 、R 103 、R 104 、R 105 、R 106 、R 107 R is R 108 Preferably represents P 13 -S 13 -, an alkoxy group having 1 to 3 carbon atoms which may be substituted with a fluorine atom, a fluorine atom or a hydrogen atom, more preferably represents P 13 -S 13 -any one of an alkoxy group having 1 to 3 carbon atoms, a fluorine atom or a hydrogen atom. The alkoxy group preferably has 1 to 3 carbon atoms, more preferably 1 to 2 carbon atoms, and particularly preferably 1 carbon atom.
In the general formula (RM), P 11 、P 12 P 13 Preferably, the compound is represented by the formula (Re-1), the formula (Re-2), the formula (Re-3) or the formula (Re-4), more preferably by the formula (Re-1), still more preferably by the formula (acryl group) or the formula (methacryl group), and particularly preferably by the formula (methacryl group).
In the general formula (RM), P 11 、P 12 P 13 All of the groups may be the same polymerizable group or may be different polymerizable groups. Preferably P 11 P 12 At least one of (C) is of the formula (Re-1), more preferably an acryl or methacryl group, still more preferably a methacryl group, particularly preferably P 11 P 12 Is a methacryloyl group.
In the above formula (RM), S 11 、S 12 S and S 13 Each independently is preferably a single bond or an alkylene group having 1 to 5 carbon atoms, and particularly preferably a single bond. At S 11 、S 12 S and S 13 In the case of a single bond, the amount of the polymerizable compound remaining after ultraviolet irradiation is sufficiently small, and display failure due to a change in pretilt angle becomes difficult to occur, and display failure of a PSA-type or PSVA-type liquid crystal display element does not occur or becomes extremely small. At S 11 、S 12 S and S 13 In the case of 1 to 3 carbon atoms, the liquid crystal display element is suitable for NPS type liquid crystal display elements.
The lower limit of the content of the polymerizable compound represented by the general formula (RM) in the liquid crystal composition of the present invention is preferably 0.01 mass%, preferably 0.02 mass%, preferably 0.03 mass%, preferably 0.04 mass%, preferably 0.05 mass%, preferably 0.06 mass%, preferably 0.07 mass%, preferably 0.08 mass%, preferably 0.09 mass%, preferably 0.1 mass%, preferably 0.12 mass%, preferably 0.15 mass%, preferably 0.17 mass%, preferably 0.2 mass%, preferably 0.22 mass%, preferably 0.25 mass%, preferably 0.27 mass%, preferably 0.3 mass%, preferably 0.32 mass%, preferably 0.35 mass%, preferably 0.37 mass%, preferably 0.4 mass%, preferably 0.42 mass%, preferably 0.45 mass%, preferably 0.5 mass%, preferably 0.55 mass%. The upper limit of the content of the polymerizable compound represented by the general formula (RM) in the liquid crystal composition of the present invention is preferably 5% by mass, preferably 4.5% by mass, preferably 4% by mass, preferably 3.5% by mass, preferably 3% by mass, preferably 2.5% by mass, preferably 2% by mass, preferably 1.5% by mass, preferably 1% by mass, preferably 0.95% by mass, preferably 0.9% by mass, preferably 0.85% by mass, preferably 0.8% by mass, preferably 0.75% by mass, preferably 0.7% by mass, preferably 0.65% by mass, preferably 0.6% by mass, preferably 0.55% by mass, preferably 0.5% by mass, preferably 0.45% by mass, preferably 0.4% by mass.
Further specifically, the content is preferably 0.2 to 0.6 mass% when a sufficient pretilt angle or a small residual amount of the polymerizable compound or a high Voltage Holding Ratio (VHR) is obtained, and the content is preferably 0.01 to 0.4 mass% when suppression of precipitation at low temperature is important. In particular, in the case where a rapid response speed is obtained, the content thereof is preferably increased to 2 mass%.
In the case of containing a plurality of polymerizable compounds represented by the general formula (RM), the content of each is preferably 0.01 to 0.4% by mass. Therefore, in order to solve all of these problems, it is particularly preferable to adjust the polymerizable compound represented by the general formula (RM) to a range of 0.1 to 0.6 mass%.
The polymerizable compound represented by the general formula (RM) according to the present invention is preferably a compound represented by the general formulae (RM-1) to (RM-10),
[ chemical 22]
Figure BDA0002440322440000201
[ chemical 23]
Figure BDA0002440322440000211
[ chemical 24]
Figure BDA0002440322440000221
In PSA-type liquid crystal display elements using these, the residual amount of polymerizable compound is small, the pretilt angle is sufficiently set, and there are no or very few defects such as alignment defects and display defects due to changes in pretilt angle.
The liquid crystal composition of the present invention contains 1 or 2 or more compounds having a terphenyl structure or a tetrabenzene structure and having a dielectric anisotropy Δεof greater than +2, that is, compounds having positive dielectric anisotropy. The Δε of the compound was the following value: a value extrapolated from a measured value of dielectric anisotropy of a composition obtained by adding the compound to a composition that is substantially dielectric neutral at 25 ℃. The compound can be used in combination with desired properties such as solubility at low temperature, transfer temperature, electrical reliability, refractive index anisotropy, and the like, and in particular, the reactivity of the polymerizable compound in the liquid crystal composition containing the polymerizable compound can be accelerated.
The lower limit of the preferable content of the compound having a terphenyl structure or a tetrabiphenyl structure and having a dielectric constant anisotropy Δεof more than +2 relative to the total amount of the liquid crystal composition of the present invention is 0.1%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 10%. The upper limit of the preferable content relative to the total amount of the liquid crystal composition of the present invention is, for example, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3% in one embodiment of the present invention.
As the compound having a terphenyl structure or a tetrabiphenyl structure and having a dielectric constant anisotropy of more than +2 which can be used in the liquid crystal composition of the present invention, for example, the compound represented by the formulae (M-8.51) to (M-8.54), the compound represented by the formulae (M-7.1) to (M-7.4), the compound represented by the formulae (M-7.11) to (M-7.14), and the compound represented by the formulae (M-7.21) to (M-7.24) are preferably contained.
[ chemical 25]
Figure BDA0002440322440000231
[ chemical 26]
Figure BDA0002440322440000232
[ chemical 27]
Figure BDA0002440322440000241
[ chemical 28]
Figure BDA0002440322440000242
To increase T of liquid crystal composition Ni The liquid crystal composition according to the present invention may contain the following compounds: compounds of formula (L-7.1) to formula (L-7.4), formula (L-7.11) to formula (L-7.13), formula (L-7.21) to formula (L-7.23), formula (L-7.31) to formula (L-7.34), formula (L-7.41) to formula (L-7.44), and formula (L-7.51) to formula (L-7.53) have a 4-ring dielectric constant of substantially zero (approximately in the range of-2 to +2).
[ chemical 29]
Figure BDA0002440322440000251
[ chemical 30]
Figure BDA0002440322440000252
[ 31]
Figure BDA0002440322440000253
[ chemical 32]
Figure BDA0002440322440000254
[ 33]
Figure BDA0002440322440000261
[ chemical 34]
Figure BDA0002440322440000262
In addition to the above-mentioned compounds, the liquid crystal composition of the present invention may contain a usual nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, antioxidant, ultraviolet absorber, light stabilizer, infrared absorber, or the like.
Examples of the antioxidants include hindered phenols (hindered phenols) represented by the general formulae (H-1) to (H-4).
[ 35]
Figure BDA0002440322440000271
In the general formulae (H-1) to (H-3), R H1 Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 2 to 10 carbon atoms, 1-CH being present in the groups 2 -or non-contiguous more than 2-CH 2 Each independently substituted by-O-or-S-and, in addition, 1 or more than 2 hydrogen atoms present in the radical may each independently be substituted by fluorine or chlorine atoms. More specifically, an alkyl group having 2 to 7 carbon atoms, an alkoxy group having 2 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms is preferable, and an alkyl group having 3 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms is more preferable.
In the general formula (H-4), M H4 Represents a single bond or an alkylene group having 1 to 10 carbon atoms, a 1, 4-phenylene group (any hydrogen atom in the group may be substituted with a fluorine atom), or a trans-1, 4-cyclohexylene group.
In the general formulae (H-1) to (H-4), 1 or non-adjacent 2 or more-ch=groups in the 1, 4-phenylene groups may be substituted with-n=groups. In addition, the hydrogen atoms in the 1, 4-phenylene group may be each independently substituted with a fluorine atom or a chlorine atom.
General formula (H-2)1 or non-contiguous more than 2-CH in 1, 4-cyclohexylene group in the general formula (H-4) 2 -may be substituted by-O-or-S-. In addition, the hydrogen atoms in the 1, 4-cyclohexylene group may be each independently substituted with a fluorine atom or a chlorine atom.
More specifically, for example, the formulae (H-11) to (H-15) can be cited.
[ 36]
Figure BDA0002440322440000281
When the liquid crystal composition of the present invention contains an antioxidant, the lower limit of the content thereof is 5 mass ppm, preferably 10 mass ppm, preferably 20 mass ppm, preferably 50 mass ppm, and the upper limit of the content thereof is 2000 mass ppm, preferably 1000 mass ppm, preferably 500 mass ppm, preferably 100 mass ppm.
When the liquid crystal composition of the present invention contains a light stabilizer, a hindered amine-based Tinuvin770 (manufactured by BASF) or LA-57 (manufactured by ADEKA) may be used, and the lower limit of the content thereof is preferably 50 mass ppm or more, preferably 100 mass ppm or more, preferably 200 mass ppm or more, and the upper limit of the content thereof is 2000 mass ppm, preferably 1000 mass ppm, preferably 500 mass ppm.
Nematic phase-isotropic liquid phase transition temperature (T) of the liquid crystal composition of the present invention NI ) From 60℃to 120℃and more preferably from 70℃to 110℃and particularly preferably from 70℃to 85 ℃. In the case of liquid crystal television applications, T NI Preferably 70 to 80 ℃, T in the case of mobile applications NI Preferably 75 to 90 ℃, T in the case of vehicle-mounted use, PID (public information display ), etc NI Preferably from 90 to 110 ℃.
The liquid crystal composition of the present invention has a refractive index anisotropy (Δn) at 20 ℃ of 0.080 to 0.140, more preferably 0.090 to 0.130, particularly preferably 0.100 to 0.120.
The liquid crystal composition of the present invention has a rotational viscosity (. Gamma.) at 20 ℃ 1 ) 50 to 160 mPas, preferably 55 to 160 mPas, preferably 60 to 160 mPas, preferably 80 to 150 mPas, preferably90 to 140 mPas, preferably 90 to 130 mPas, preferably 90 to 120 mPas.
The liquid crystal composition of the present invention has a dielectric anisotropy (. DELTA.. Epsilon.) of from-1.5 to-4.0, preferably from-1.5 to-3.5, more preferably from-1.7 to-3.2, more preferably from-1.7 to-3.0, more preferably from-1.7 to-2.7, and particularly preferably from-1.7 to-2.5 at 20 ℃.
The liquid crystal display element using the liquid crystal composition of the present invention is useful particularly for an active matrix driving liquid crystal display element, and can be suitably used for a liquid crystal display element such as VA, FFS, IPS, PSA, PSVA, PS-IPS or PS-FFS, NPS, PI-less.
The liquid crystal display element of the present invention preferably includes a 1 st substrate and a 2 nd substrate which are disposed to face each other, a common electrode provided on the 1 st substrate or the 2 nd substrate, a pixel electrode provided on the 1 st substrate or the 2 nd substrate and having a thin film transistor, and a liquid crystal layer provided between the 1 st substrate and the 2 nd substrate and containing a liquid crystal composition. Optionally, an alignment film for controlling the alignment direction of the liquid crystal molecules may be provided on the opposite surface side of at least one of the 1 st substrate and the 2 nd substrate so as to be in contact with the liquid crystal layer. As the alignment film, a vertical alignment film, a horizontal alignment film, or the like may be appropriately selected in accordance with the driving mode of the liquid crystal display element, and a known alignment film such as a rubbing alignment film (for example, polyimide) or a photo alignment film (for example, decomposed polyimide) may be used. Further, a color filter may be provided on the 1 st substrate or the 2 nd substrate, and a color filter may be provided on the pixel electrode or the common electrode.
As the 2-sheet substrate used for the liquid crystal cell of the liquid crystal display element according to the present invention, glass or a transparent material having flexibility such as plastic may be used, and one of them may be an opaque material such as silicon. The transparent substrate having the transparent electrode layer can be obtained by, for example, sputtering Indium Tin Oxide (ITO) on a transparent substrate such as a glass plate.
The color filter can be produced by, for example, pigment dispersion, printing, electrodeposition, dyeing, or the like. In the case of describing a method of producing a color filter by a pigment dispersion method as an example, the curable coloring composition for a color filter is applied to the transparent substrate, subjected to patterning treatment, and then cured by heating or light irradiation. By performing this step for each of the 3 colors of red, green, and blue, a pixel portion for a color filter can be manufactured. In addition, pixel electrodes including active elements such as TFTs, thin film diodes, and metal-insulator-metal resistor elements may be provided on the substrate.
The 1 st substrate and the 2 nd substrate are preferably opposed to each other with the common electrode and the pixel electrode layer inside.
The spacing between the 1 st substrate and the 2 nd substrate can be adjusted by the spacers. In this case, the thickness of the obtained light control layer is preferably adjusted so that the thickness is 1 to 100. Mu.m. More preferably 1.5 to 10. Mu.m, when a polarizing plate is used, the product of the refractive index anisotropy Deltan of the liquid crystal and the cell thickness d is preferably adjusted so that the contrast ratio becomes maximum. In addition, when two polarizing plates are provided, the polarizing axis of each polarizing plate can be adjusted so that the viewing angle and contrast are good. Further, a retardation film for expanding the viewing angle may be used. Examples of the spacer include: glass particles, plastic particles, alumina particles, photoresist (photoresist) materials, and the like. Then, a sealant such as an epoxy thermosetting composition is screen-printed on the substrates in a shape provided with a liquid crystal injection port, and the substrates are bonded to each other, and the sealant is thermally cured by heating.
As a method for sandwiching the liquid crystal composition between 2 substrates, a general vacuum injection method, an ODF method, or the like can be used.
In order to form the alignment state of the liquid crystal display element of the present invention, the liquid crystal display element can be produced by using a liquid crystal composition containing a polymerizable compound in a liquid crystal composition and polymerizing the polymerizable compound in the liquid crystal composition.
The method for polymerizing the polymerizable compound contained in the liquid crystal composition of the present invention is preferably the following method: in order to obtain good alignment performance of the liquid crystal layer, it is desirable to polymerize at a proper polymerization rate, and therefore, the liquid crystal layer is polymerized by irradiation of active energy rays such as ultraviolet rays or electron beams singly or in combination or sequentially. In the case of using ultraviolet rays, a polarized light source may be used, and a non-polarized light source may also be used. In addition, in the case of polymerization in a state where the liquid crystal composition is sandwiched between 2 substrates, at least the substrate on the irradiation surface side must have appropriate transparency to active energy rays. In addition, the following means may be used: after polymerizing only a specific portion using a mask at the time of light irradiation, conditions such as an electric field, a magnetic field, or a temperature are changed, whereby the orientation state of the unpolymerized portion is changed, and further an active energy ray is irradiated to polymerize. In particular, when ultraviolet exposure is performed, it is preferable to perform ultraviolet exposure while applying an alternating electric field to the liquid crystal composition. The applied alternating electric field is preferably alternating current with a frequency of 10Hz to 10kHz, more preferably with a frequency of 60Hz to 10kHz, the voltage being selected depending on the desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled by the applied voltage. In the case of a PSVA type liquid crystal display element, the pretilt angle is preferably controlled to 80 to 89.9 degrees from the viewpoints of alignment stability and contrast.
The temperature at which the active energy rays such as ultraviolet rays and electron beams are irradiated for polymerizing the polymerizable compound contained in the liquid crystal composition of the present invention is not particularly limited. For example, when the liquid crystal composition of the present invention is applied to a liquid crystal display element having a substrate with an alignment film, it is preferable that the liquid crystal composition is maintained in a liquid crystal state within a temperature range. It is preferably polymerized at a temperature close to room temperature, i.e., typically 15 to 35 ℃.
On the other hand, for example, when the liquid crystal composition of the present invention is applied to a liquid crystal display element having a substrate without an alignment film, the temperature range may be wider than the above-described temperature range when the composition is applied to the liquid crystal display element having a substrate with an alignment film.
As the lamp for generating ultraviolet rays, a metal halogen lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, or the like can be used. The wavelength of the irradiated ultraviolet light is preferably ultraviolet light in a wavelength region other than the absorption wavelength region of the liquid crystal composition, and if necessary, the ultraviolet light is preferably filtered off. Intensity of irradiated ultraviolet raysThe degree of rotation is preferably 0.1mW/cm 2 ~100W/cm 2 More preferably 2mW/cm 2 ~50W/cm 2 . The energy of the irradiated ultraviolet rays can be suitably adjusted, and is preferably 10mJ/cm 2 To 500J/cm 2 More preferably 100mJ/cm 2 ~200J/cm 2 . When ultraviolet rays are irradiated, the intensity may be changed. The time for irradiating ultraviolet rays may be appropriately selected depending on the intensity of the irradiated ultraviolet rays, and is preferably 10 seconds to 3600 seconds, more preferably 10 seconds to 600 seconds.
Examples
The present invention will be further described in detail with reference to the following examples, but the present invention is not limited to these examples. In the following examples and comparative examples, the term "%" means "% by mass". The following codes are used for the description of the compounds in the examples.
(side chain)
-n -C n H 2n+1 Straight-chain alkyl of carbon number n
n- C n H 2n+1 Linear alkyl of carbon number n
-On -OC n H 2n+1 Straight-chain alkoxy of carbon number n
nO- C n H 2n+1 Linear alkoxy of O-carbon number n
-V -CH=CH 2
V- CH 2 =CH-
-V1 -CH=CH-CH 3
1V- CH 3 -CH=CH-
-F -F
-OCF3 -OCF 3
(linking group)
-CF2O- -CF 2 -O-
-OCF2- -O-CF 2 -
-1O- -CH 2 -O-
-O1- -O-CH 2 -
-2- -CH 2 -CH 2 -
-COO- -COO-
-OCO- -OCO-
-single bond
(Ring structure)
[ 37]
Figure BDA0002440322440000321
In the examples, the measured characteristics are as follows.
T NI : nematic phase-isotropic liquid phase transition temperature (. Degree. C.)
An: refractive index anisotropy at 20 DEG C
Δε: dielectric constant anisotropy at 20 DEG C
γ 1 : rotational viscosity at 20 ℃ (mPa. S)
K 11 : elastic constant K at 20 DEG C 11 (pN)
K 33 : elastic constant K at 20 DEG C 33 (pN)
RT: response speed (msec) when voltage is applied
VHR: voltage holding ratio at 70℃at 1V, 0.6Hz (%)
T: transmittance (%) when voltage is applied.
(results of preparation and evaluation of liquid Crystal composition)
Liquid crystal compositions of example 1 (LC-1), example 2 (LC-2), example 3 (LC-3) and comparative example 1 (LC-A) were prepared, and physical properties were measured. The composition ratios and physical property values of these liquid crystal compositions are shown in table 1.
TABLE 1
Figure BDA0002440322440000331
These liquid crystal compositions are described as K 11 K is as follows 33 The composition ratio was adjusted so that the physical properties were similar to each other.
Delta epsilon of example 1 (LC-1) is negative and T NI High, gamma 1 Small, delta n large, K 11 Is small. Due to gamma associated with response speed 1 /K 33 The value of (2) is smaller, thus implying a faster response speed. And (3) confirming: the FFS type and VA type liquid crystal display devices obtained using the liquid crystal composition of example 1 have a fast response speed, a high VHR and a high transmittance. In addition, it was confirmed that: these liquid crystal display elements have no display failure. That is, it is confirmed that: the liquid crystal composition of example 1 (LC-1) and a liquid crystal display element using the same solve the problems of the present invention. The cell thickness (d) of the liquid crystal display element is determined so that the value of retardation (Δnd) becomes 360.
A PSA-type liquid crystal display element was produced by preparing a polymerizable compound-containing liquid crystal composition obtained by mixing 99.7% of the liquid crystal composition of example 1 (LC-1) and 0.3% of the polymerizable compound (RM-1). The present invention was found to solve the problems of the present invention by showing the same physical properties. Further, the liquid crystal composition containing the polymerizable compound obtained by replacing the polymerizable compound (RM-1) with the polymerizable compound (RM-2), the polymerizable compound (RM-4), or the polymerizable compound (RM-5) also exhibits excellent effects in the same manner.
Delta epsilon of example 2 (LC-2) is negative and T NI High, gamma 1 Small, delta n large, K 11 Is small. And (3) confirming: the VA-mode liquid-crystal display device obtained using the liquid-crystal composition of example 2 has a fast response speed, a high VHR and a high transmittance. In addition, it was confirmed that: these liquid crystal display elements have no display failure. That is, it is confirmed that: the liquid crystal composition of example 2 (LC-2) and a liquid crystal display element using the same solve the problems of the present invention.
A PSA type liquid crystal display element was produced by preparing a polymerizable compound-containing liquid crystal composition obtained by mixing 99.6% of the liquid crystal composition of example 2 (LC-2) and 0.4% of the polymerizable compound (RM-2). It was confirmed that the problems of the present invention are also solved. Further, the liquid crystal composition containing the polymerizable compound obtained by replacing the polymerizable compound (RM-2) with the polymerizable compound (RM-1), the polymerizable compound (RM-4), or the polymerizable compound (RM-5) also exhibits excellent effects in the same manner.
Delta epsilon of example 3 (LC-3) is negative, T NI High, gamma 1 Small, delta n large, K 11 Is small. And (3) confirming: the VA-mode liquid-crystal display device obtained using the liquid-crystal composition of example 3 has a fast response speed, a high VHR and a high transmittance. In addition, it was confirmed that: these liquid crystal display elements have no display failure. That is, it is confirmed that: the liquid crystal composition of example 3 (LC-3) and a liquid crystal display element using the same solve the problems of the present invention.
A PSA-type liquid crystal display element was produced by preparing a polymerizable compound-containing liquid crystal composition obtained by mixing 99.75% of the liquid crystal composition of example 3 (LC-3) and 0.25% of the polymerizable compound (RM-4). It was confirmed that the problems of the present invention are also solved. Further, the liquid crystal composition containing the polymerizable compound obtained by replacing the polymerizable compound (RM-4) with the polymerizable compound (RM-1), the polymerizable compound (RM-2), or the polymerizable compound (RM-5) also exhibits excellent effects in the same manner.
A PSA-type liquid crystal display element was produced by preparing a liquid crystal composition containing a polymerizable compound obtained by mixing 99.72% of the liquid crystal composition of example 3 (LC-3) and 0.28% of the polymerizable compound (RM-12). It was confirmed that the problems of the present invention are also solved.
A PSA-type liquid crystal display element was produced by preparing a liquid crystal composition containing a polymerizable compound obtained by mixing 99.72% of the liquid crystal composition of example 3 (LC-3) and 0.28% of the polymerizable compound (RM-14). It was confirmed that the problems of the present invention are also solved.
A PSA-type liquid crystal display element was produced by preparing a liquid crystal composition containing a polymerizable compound obtained by mixing 99.72% of the liquid crystal composition of example 3 (LC-3) and 0.28% of the polymerizable compound (RM-15). It was confirmed that the problems of the present invention are also solved.
On the other hand, comparative example 1 (LC-A) is se:Sub>A liquid crystal composition containing 3-Cy-1O-Ph5-O2, K 11 Large. And (3) confirming: FFS type and VA type liquid crystal display elements obtained using the liquid crystal composition of comparative example 1 were low in VHR and transmittance, and display failure occurred. That is, it is confirmed that: the liquid crystal composition of comparative example 1 (LC-se:Sub>A) and the liquid crystal display element using the same cannot solve the problems of the present invention.
Further, se:Sub>A liquid crystal composition was prepared by replacing 3-Cy-1O-Ph5-O2 of comparative example 1 (LC-A) with 3-Cy-Cy-1O-Ph5-O2, and as se:Sub>A result, it was confirmed that the VA type liquid crystal display element had low VHR and low transmittance, and display failure occurred. That is, it is confirmed that: the liquid crystal composition containing 3-Cy-Cy-1O-Ph5-O2 and the liquid crystal display element using the same cannot solve the problems of the present invention.
Liquid crystal compositions of example 4 (LC-4), example 5 (LC-5), example 6 (LC-6) and comparative example 2 (LC-B) were prepared, and physical properties were measured. The composition ratios and physical property values of these liquid crystal compositions are shown in table 2.
TABLE 2
Figure BDA0002440322440000361
And (3) confirming: the problems of the present invention are solved by setting Δεof examples 4 (LC-4), 5 (LC-5) and 6 (LC-6) to be negative. On the other hand, confirm: the VHR of comparative example 2 (LC-B) was 76%, and the problem could not be solved.
A PSA-type liquid crystal display element was produced by preparing a polymerizable compound-containing liquid crystal composition obtained by mixing 99.6% of the liquid crystal composition of example 4 (LC-4) and 0.4% of the polymerizable compound (RM-1). It was confirmed that the problems of the present invention are also solved.
A PSA type liquid crystal display element was produced by preparing a polymerizable compound-containing liquid crystal composition obtained by mixing 99.6% of the liquid crystal composition of example 4 (LC-4) and 0.4% of the polymerizable compound (RM-2). It was confirmed that the problems of the present invention are also solved.
A PSA-type liquid crystal display element was produced by preparing a polymerizable compound-containing liquid crystal composition obtained by mixing 99.6% of the liquid crystal composition of example 4 (LC-4) and 0.4% of the polymerizable compound (RM-3). It was confirmed that the problems of the present invention are also solved.
A PSA-type liquid crystal display element was produced by preparing a liquid crystal composition containing a polymerizable compound obtained by mixing 99.6% of the liquid crystal composition of example 4 (LC-4) and 0.4% of the polymerizable compound (RM-4). It was confirmed that the problems of the present invention are also solved.
A PSA type liquid crystal display element was produced by preparing a polymerizable compound-containing liquid crystal composition obtained by mixing 99.6% of the liquid crystal composition of example 4 (LC-4) and 0.4% of the polymerizable compound (RM-5). It was confirmed that the problems of the present invention are also solved.
In example 5 (LC-5), the same experiment as in example 4 was also performed, and it was confirmed that the problem of the present invention was solved.
In example 6 (LC-6), the same experiment as in example 4 was also performed, and it was confirmed that the problem of the present invention was solved.
A liquid crystal composition containing a polymerizable compound was prepared by mixing 99.65% of the liquid crystal composition of example 6 (LC-6) and 0.35% of the polymerizable compound (RM-11), and a PSA-type liquid crystal display element was produced. It was confirmed that the problems of the present invention are also solved.
A PSA type liquid crystal display element was produced by preparing a polymerizable compound-containing liquid crystal composition obtained by mixing 99.65% of the liquid crystal composition of example 6 (LC-6) and 0.35% of the polymerizable compound (RM-12). It was confirmed that the problems of the present invention are also solved.
A PSA type liquid crystal display element was produced by preparing a polymerizable compound-containing liquid crystal composition obtained by mixing 99.65% of the liquid crystal composition of example 6 (LC-6) and 0.35% of the polymerizable compound (RM-14). It was confirmed that the problems of the present invention are also solved.
A liquid crystal composition containing a polymerizable compound was prepared by mixing 99.65% of the liquid crystal composition of example 6 (LC-6) and 0.35% of the polymerizable compound (RM-15), and a PSA-type liquid crystal display element was produced. It was confirmed that the problems of the present invention are also solved.
Comparative example 2 (LC-B) was a liquid crystal composition containing 3-Cy-Cy-1O-Ph5-O2, and it was confirmed that: FFS type and VA type liquid crystal display elements produced using the same have low VHR and low transmittance, and display failure occurs. That is, it is confirmed that: the liquid crystal composition of comparative example 2 (LC-B) and the liquid crystal display element using the same cannot solve the problems of the present invention.
Symbol description
1. Transmittance of liquid crystal display element using liquid crystal composition of (LC-1)
2. Transmittance of liquid crystal display element using liquid crystal composition of (LC-2)
3. Transmittance of liquid crystal display element using liquid crystal composition of (LC-3)

Claims (13)

1. A liquid crystal composition comprising 1 or 2 or more compounds represented by the general formula (S1), 1 or 2 or more compounds represented by the general formula (S2), 1 or 2 or more compounds represented by the general formula (S3), 10 to 50 mass% of the compound represented by the general formula (S1), 14 to 34 mass% of the compound represented by the general formula (S2), 19 to 39 mass% of the compound represented by the general formula (S3), 3 to 30 mass% of the compound represented by the general formula (NU-05), 1 to 20 mass% of the compound represented by the general formula (NU-03-1), 0 to 20 mass% of the compound represented by the general formula (NU-03-2), 1 to 25 mass% of the compound represented by the general formula (NU-02-1), the total mass of these components being 85 to 100 mass% and the anisotropy delta is negative epsilon,
Figure FDA0004142525930000011
Wherein R is S1 R is R S2 Each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, R S3 R is R S5 Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, R S4 R is R S6 Each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms,
Figure FDA0004142525930000012
wherein R is NU51 、R NU52 Independently represent an alkyl group having 1 to 8 carbon atoms and a carbon atomAlkoxy of 1 to 8, alkenyl of 2 to 8 carbon atoms, alkenyloxy of 2 to 8 carbon atoms, 1 of the groups or non-contiguous 2 or more-CH 2 Can be independently and individually substituted by-CH=CH-, -C≡C-, -O-, -CO-, -COO-or-OCO-substitution,
Figure FDA0004142525930000021
2. the liquid crystal composition according to claim 1, wherein the total content of the compounds represented by the general formulae (S2) and (S3) in the total amount of the compounds having the structures represented by the formulae (NS-1) to (NS-4) in the molecule in the liquid crystal composition is 90% by mass or more,
Figure FDA0004142525930000022
wherein the other structures are combined at the same point.
3. The liquid crystal composition according to claim 1 or 2, which contains 1 or 2 or more compounds selected from the group of compounds represented by the general formulae (NU-02) to (NU-04), the general formulae (NU-06) and (NU-07),
Figure FDA0004142525930000023
Figure FDA0004142525930000031
Wherein R is NU21 、R NU22 、R NU31 、R NU32 、R NU41 、R NU42 、R NU61 、R NU62 、R NU71 R is R NU72 Independently represent alkyl group having 1 to 8 carbon atoms, alkoxy group having 1 to 8 carbon atoms, or compound having 2 to 8 carbon atoms8 alkenyl groups, alkenyloxy groups having 2 to 8 carbon atoms, 1 of the groups being non-contiguous with more than 2-CH 2 -may each be independently substituted by-ch=ch-, -c≡c-, -O-, -CO-, -COO-, or-OCO-.
4. The liquid crystal composition according to claim 3, wherein the total content of the compounds represented by the general formulae (S1), (S2), (S3), (NU-02), (NU-03), (NU-04), (NU-05), (NU-06) and (NU-07) in the liquid crystal composition is 95 to 100% by mass based on the entire liquid crystal composition.
5. The liquid crystal composition according to claim 3, wherein the total content of the compounds represented by the general formulae (S1), (S2), (S3), (NU-02), (NU-03), (NU-05), (NU-06) and (NU-07) in the liquid crystal composition is 85 to 100% by mass based on the whole liquid crystal composition.
6. The liquid crystal composition according to claim 1 or 2, which contains 1 or 2 or more compounds having a terphenyl structure or a tetrabenzoyl structure and having a dielectric constant anisotropy Δεof greater than +2.
7. The liquid crystal composition according to claim 1 or 2, which contains 1 or 2 or more compounds represented by the formulae (NU-05-1) to (NU-05-10) as the compound represented by the general formula (NU-05),
Figure FDA0004142525930000041
8. the liquid crystal composition according to claim 1 or 2, wherein the compound represented by the general formula (S1) is a compound represented by the formula (S1-1), the formula (S1-2) or the formula (S1-3),
Figure FDA0004142525930000051
9. the liquid crystal composition according to claim 1, which has refractive index anisotropy Δn in the range of 0.100 to 0.120.
10. The liquid crystal composition according to claim 1, which has a dielectric constant anisotropy Δεranging from-1.7 to-2.5.
11. A liquid crystal display element using the liquid crystal composition according to any one of claims 1 to 9.
12. A liquid crystal display element for active matrix driving using the liquid crystal composition according to any one of claims 1 to 9.
13. A VA-type, IPS-type, FFS-type, PSA-type or PSVA-type liquid crystal display element using the liquid crystal composition according to any one of claims 1 to 9.
CN201880065166.8A 2017-11-21 2018-11-08 Liquid crystal composition and liquid crystal display element Active CN111183205B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2017223605 2017-11-21
JP2017-223605 2017-11-21
PCT/JP2018/041475 WO2019102859A1 (en) 2017-11-21 2018-11-08 Liquid crystal composition and liquid crystal display element

Publications (2)

Publication Number Publication Date
CN111183205A CN111183205A (en) 2020-05-19
CN111183205B true CN111183205B (en) 2023-06-02

Family

ID=66631940

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201880065166.8A Active CN111183205B (en) 2017-11-21 2018-11-08 Liquid crystal composition and liquid crystal display element

Country Status (4)

Country Link
JP (1) JP6525227B1 (en)
CN (1) CN111183205B (en)
TW (1) TWI786218B (en)
WO (1) WO2019102859A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111315848A (en) * 2017-12-11 2020-06-19 Dic株式会社 Liquid crystal display element
JP7326959B2 (en) * 2019-07-24 2023-08-16 Dic株式会社 Composition and liquid crystal display element using the same
JP7409047B2 (en) * 2019-11-27 2024-01-09 Dic株式会社 Composition and liquid crystal display device using the same

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103459552A (en) * 2011-04-06 2013-12-18 Dic株式会社 Nematic liquid crystal composition, liquid crystal display element using same
CN104185671A (en) * 2013-03-26 2014-12-03 Dic株式会社 Liquid crystal composition, and liquid crystal display element using same
WO2014192454A1 (en) * 2013-05-28 2014-12-04 Jnc株式会社 Liquid crystal composition and liquid crystal display element
CN104797687A (en) * 2013-03-21 2015-07-22 Dic株式会社 Liquid crystal composition and liquid crystal display element using same
JP2017145384A (en) * 2016-02-17 2017-08-24 Jnc株式会社 Liquid crystal composition and liquid crystal display element
WO2017145611A1 (en) * 2016-02-25 2017-08-31 Jnc株式会社 Liquid crystal composition and liquid crystal display element
JP2017193596A (en) * 2016-04-18 2017-10-26 Jnc株式会社 Liquid crystal composition and liquid crystal display element
CN110199008A (en) * 2017-03-17 2019-09-03 捷恩智株式会社 Liquid-crystal composition and liquid crystal display element

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5374904B2 (en) * 2007-04-06 2013-12-25 Jnc株式会社 Compound having alkadienyl group and liquid crystal composition using the same
KR101365111B1 (en) * 2007-05-02 2014-02-19 삼성디스플레이 주식회사 Liquid crystal composition and liquid crystal display apparatus using the same
CN101796162B (en) * 2007-08-15 2014-03-19 默克专利股份有限公司 Liquid-crystalline medium
WO2010057575A1 (en) * 2008-11-19 2010-05-27 Merck Patent Gmbh Liquid crystalline medium
GB2491087B (en) * 2010-03-04 2016-11-09 Merck Patent Gmbh Liquid-crystalline medium
US20150337200A1 (en) * 2012-10-23 2015-11-26 Dic Corporation Liquid crystal composition, liquid crystal display element, and liquid crystal display
JP6510419B2 (en) * 2012-12-17 2019-05-08 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung Liquid crystal display and liquid crystal medium having homeotropic alignment
EP2801600B1 (en) * 2013-03-26 2018-11-14 DIC Corporation Liquid crystal composition and liquid crystal display element incorporating same
KR20150070027A (en) * 2013-12-16 2015-06-24 메르크 파텐트 게엠베하 Liquid-crystalline medium
DE112014006109B4 (en) * 2014-01-06 2018-09-20 Dic Corporation A nematic liquid crystal composition and its use for producing a liquid crystal display element
US20170226419A1 (en) * 2014-06-19 2017-08-10 Dic Corporation Polymerizable-monomer-containing liquid crystal composition and liquid crystal display element using same
WO2015198960A1 (en) * 2014-06-25 2015-12-30 Dic株式会社 Liquid crystal display element and method for producing same
CN106795434A (en) * 2014-10-10 2017-05-31 Dic株式会社 Liquid-crystal composition and use its liquid crystal display cells
EP3067405B1 (en) * 2015-03-10 2019-03-27 Merck Patent GmbH Liquid crystalline medium
KR102367600B1 (en) * 2015-03-30 2022-02-28 삼성디스플레이 주식회사 Display device and fabrication method of the same
KR20170015800A (en) * 2015-07-31 2017-02-09 삼성디스플레이 주식회사 Liquid crystal composition and liquid crystal display including the same
WO2017026479A1 (en) * 2015-08-11 2017-02-16 Dic株式会社 Liquid crystal display element
KR20180054688A (en) * 2015-09-15 2018-05-24 메르크 파텐트 게엠베하 Liquid crystal medium with homeotropic alignment
CN107849451A (en) * 2015-11-19 2018-03-27 Dic株式会社 Liquid-crystal composition, liquid crystal display cells and liquid crystal display
CN105694909B (en) * 2016-01-13 2018-08-28 石家庄诚志永华显示材料有限公司 Liquid-crystal composition
CN105567251B (en) * 2016-01-13 2018-07-31 石家庄诚志永华显示材料有限公司 Liquid-crystal composition

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103459552A (en) * 2011-04-06 2013-12-18 Dic株式会社 Nematic liquid crystal composition, liquid crystal display element using same
CN104797687A (en) * 2013-03-21 2015-07-22 Dic株式会社 Liquid crystal composition and liquid crystal display element using same
CN104185671A (en) * 2013-03-26 2014-12-03 Dic株式会社 Liquid crystal composition, and liquid crystal display element using same
WO2014192454A1 (en) * 2013-05-28 2014-12-04 Jnc株式会社 Liquid crystal composition and liquid crystal display element
JPWO2014192454A1 (en) * 2013-05-28 2017-02-23 Jnc株式会社 Liquid crystal composition and liquid crystal display element
JP2017145384A (en) * 2016-02-17 2017-08-24 Jnc株式会社 Liquid crystal composition and liquid crystal display element
WO2017145611A1 (en) * 2016-02-25 2017-08-31 Jnc株式会社 Liquid crystal composition and liquid crystal display element
JP2017193596A (en) * 2016-04-18 2017-10-26 Jnc株式会社 Liquid crystal composition and liquid crystal display element
CN110199008A (en) * 2017-03-17 2019-09-03 捷恩智株式会社 Liquid-crystal composition and liquid crystal display element

Also Published As

Publication number Publication date
CN111183205A (en) 2020-05-19
WO2019102859A1 (en) 2019-05-31
TWI786218B (en) 2022-12-11
JP6525227B1 (en) 2019-06-05
TW201925432A (en) 2019-07-01
JPWO2019102859A1 (en) 2019-12-12

Similar Documents

Publication Publication Date Title
CN109072079B (en) Liquid crystal composition and liquid crystal display element
CN108779395B (en) Nematic liquid crystal composition and liquid crystal display element using same
TWI773789B (en) Liquid crystal composition and liquid crystal display element
CN109423306B (en) Liquid crystal composition and liquid crystal display element
TW201412957A (en) Nematic liquid crystal composition and liquid crystal display element using same
EP2727978A1 (en) Nematic liquid crystal composition and liquid crystal display element using same
CN111154500B (en) Liquid crystal composition and liquid crystal display element
CN111183205B (en) Liquid crystal composition and liquid crystal display element
CN111373017B (en) Liquid crystal composition and liquid crystal display element
JP6452019B1 (en) Liquid crystal composition and liquid crystal display element
TW201425543A (en) Nematic liquid crystal composition and liquid crystal display element using same
TWI597352B (en) Nematic liquid crystal composition and liquid crystal display device using the same
CN113234453A (en) Liquid crystal composition and liquid crystal display
CN113265261A (en) Liquid crystal composition and liquid crystal display
CN112980465B (en) Liquid crystal composition and liquid crystal display element
JP2020097677A (en) Liquid crystal composition and liquid crystal display element
CN111334311B (en) Liquid crystal composition and liquid crystal display element
CN110734770B (en) Liquid crystal composition and liquid crystal display element
CN113249129A (en) Liquid crystal composition and liquid crystal display

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
TR01 Transfer of patent right

Effective date of registration: 20240520

Address after: 606 Huai'an East Road, Shijiazhuang City, Hebei Province

Patentee after: Shijiazhuang Chengzhi Yonghua Display Materials Co.,Ltd.

Country or region after: China

Address before: Tokyo, Japan

Patentee before: DIC Corp.

Country or region before: Japan

TR01 Transfer of patent right