CN109575936A - Liquid crystal compound, liquid crystal composition, and liquid crystal display element - Google Patents
Liquid crystal compound, liquid crystal composition, and liquid crystal display element Download PDFInfo
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 156
- 150000001875 compounds Chemical class 0.000 title claims abstract description 95
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- -1 5- indanyl Chemical group 0.000 claims description 9
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 239000012071 phase Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 210000002858 crystal cell Anatomy 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IKOXJOTULSXNNR-UHFFFAOYSA-N 3-propylcyclopentan-1-ol Chemical compound CCCC1CCC(O)C1 IKOXJOTULSXNNR-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- UGTFAOKMOKDAIM-UHFFFAOYSA-N C(CC)C1CC(CC1)=O.C(CC)C1CC(CC1)=O Chemical compound C(CC)C1CC(CC1)=O.C(CC)C1CC(CC1)=O UGTFAOKMOKDAIM-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/301—Cy-Cy-Ph
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3016—Cy-Ph-Ph
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Disclosed are a liquid crystal compound, a liquid crystal composition, and a liquid crystal display element. The liquid crystal compound has a structure shown in a formula (I), is a negative liquid crystal compound and has lower dielectric anisotropy and higher vertical dielectric constant, so that the driving voltage of the liquid crystal compound is favorably reduced, and a liquid crystal display element containing the liquid crystal compound has better transmissivity.
Description
Technical field
The present invention relates to liquid-crystal compounds, liquid-crystal composition and liquid crystal display elements (device, device), and especially
It is related to negative type liquid crystal compound and the LCD compound with lower dielectric anisotropy and higher vertical dielectric constant
Object, liquid-crystal composition and the liquid crystal display element comprising liquid-crystal composition.
Background technique
Liquid crystal display element is the display element changed using the photoelectricity of liquid crystal, with small in size, light-weight, low electric power
The advantages that consumption is good with display quality, therefore the market mainstream is had become in recent years.
It include liquid-crystal composition in liquid crystal display element, liquid-crystal composition includes more than one liquid-crystal compounds, is
The performance of liquid crystal display element is promoted, liquid-crystal compounds should have characteristics that (1) chemical property and physical property are stablized；
(2) clearing point (phase transition temperature of nematic phase to liquid phase) with higher；(3) nematic lower limit temperature is lower；(4) with it is other
The intermiscibility (compatibility) of liquid-crystal compounds is excellent；(5) absolute value of dielectric anisotropy it is larger (i.e. positive type liquid crystal have it is higher
Dielectric anisotropy, negative type liquid crystal have lower dielectric anisotropy).
When in liquid crystal display element comprising chemical property and physical property stable liquid-crystal compounds, voltage guarantor can be improved
Holdup.When using having higher clearing point and nematic phase lower limit temperature lower liquid-crystal compounds, nematic temperature can be widened
Range is spent, so that the use temperature range of liquid crystal display element be made to become larger, and then expands the application range of liquid crystal display element.When
When using the liquid-crystal compounds excellent with the intermiscibility of other liquid-crystal compounds, the property of liquid-crystal composition can be promoted.Due to list
One liquid-crystal compounds is difficult to have above-mentioned all features, therefore liquid-crystal composition generally comprises more than one liquid-crystal compounds,
When the intermiscibility of liquid-crystal compounds to each other is higher, be conducive to the uniformity and stability of liquid-crystal composition.When using absolute
It is worth the liquid-crystal compounds of biggish dielectric anisotropy, for example, when the negative type liquid crystal with lower dielectric anisotropy, then favorably
In the driving voltage for reducing negative type liquid crystal compound, when using the negative type liquid crystal compound with higher vertical dielectric constant,
The transmissivity (penetration) of liquid crystal display element can then be promoted.
Therefore, the performance of liquid-crystal compounds and liquid crystal display element is closely bound up, how to improve the molecule of liquid-crystal compounds
Structure is the target that related practitioner makes great efforts further to improve the quality of liquid crystal display element.
Summary of the invention
It is that (i.e. dielectric is respectively to different for minus liquid-crystal compounds it is an object of the present invention to provide a kind of liquid-crystal compounds
Property less than 0) and have lower dielectric anisotropy and higher vertical dielectric constant.
It is a further object of the present invention to provide a kind of liquid-crystal compositions, and it includes liquid-crystal compounds above-mentioned, therefore are conducive to
Reduce driving voltage.
Another object of the present invention is to provide a kind of liquid crystal display element, and it includes liquid-crystal compositions above-mentioned, therefore can mention
Rise the transmissivity of liquid crystal display element.
A kind of embodiment according to the present invention, provides a kind of liquid-crystal compounds, has the structure as shown in formula (I):
Wherein R1With R2The alkynyl of the alkyl of carbon number 1 to 10, the alkenyl of carbon number 2 to 10 or carbon number 2 to 10 is respectively stood alone as,
Wherein R1With R2In arbitrary H can be replaced (instead of) by F, n and m respectively stand alone as 0 or 1, and n+m=1 or n+m=2.
Another embodiment according to the present invention, provides a kind of liquid-crystal composition, and it includes LCD compounds as described above
Object.
A further embodiment according to the present invention provides a kind of liquid crystal display element, and it includes liquid crystal groups as described above
Close object.
Specific embodiment
Liquid-crystal compounds
Liquid-crystal compounds of the invention has the structure as shown in formula (I):
In formula (I), R1With R2Respectively stand alone as the alkynes of the alkyl of carbon number 1 to 10, the alkenyl of carbon number 2 to 10 or carbon number 2 to 10
Base, wherein R1With R2In arbitrary H can be replaced by F, n and m respectively stand alone as 0 or 1, and n+m=1 or n+m=2.This hair as a result,
Bright liquid-crystal compounds is minus liquid-crystal compounds and has lower dielectric anisotropy and higher vertical dielectric constant,
Forenamed vertical dielectric constant refers to perpendicular to average dielectric constant measured by long axis of liquid crystal molecule.
In liquid-crystal compounds above-mentioned, R1With R2The alkyl of carbon number 1 to 5 can be respectively stood alone as, n and m can respectively be stood alone as
0 or 1, and n+m=1.
Liquid-crystal compounds above-mentioned can have the structure as shown in formula (I-1), formula (I-2), formula (I-3) or formula (I-4):
Liquid-crystal composition
Liquid-crystal composition of the invention includes liquid-crystal compounds above-mentioned, is please referred to above, herein about liquid-crystal compounds
It will not go into details.
According to liquid-crystal composition above-mentioned, the content based on the liquid-crystal composition is 100 weight percent (%), is liquid-crystalized
The content for closing object can be 0.1 weight percent to 35 weight percent.
According to liquid-crystal composition above-mentioned, the chemical combination as shown in formula (II), formula (III) and formula (IV) can further include
At least one of object:
R3–A1–Z1–A2-R4(II)；
R5–A3–Z2–A4–Z3–A5–R6(III)；
R7–A6–Z4–A7–Z5–A8–Z6–A9–R8 (IV)。
In formula (II) into formula (IV), R3、R4、R5、R6、R7With R8Respectively stand alone as F, the alkyl of carbon number 1 to 10 or carbon number 2
To 10 alkenyl, R3、R4、R5、R6、R7With R8In arbitrary H can be replaced by F, and R3、R4、R5、R6、R7With R8In arbitrary-CH2-
It can be replaced by-O-.A1、A2、A3、A4、A5、A6、A7、A8With A9It is sub- respectively to stand alone as 1,4- cyclohexylidene, 1,4- phenylene, 1,3-
Cyclopenta, bicyclic [2.2.2] octyl of dioxa-of divalent, bicyclic [2.2.2] octyl of trioxa-of divalent or divalent
2,5- indanyls, and A1、A2、A3、A4、A5、A6、A7、A8With A9In arbitrary H can be replaced by F, alkyl or alkoxy.Z1、Z2、Z3、
Z4、Z5With Z6Respectively stand alone as singly-bound ,-CH2-、-CH2O-、-C2H4-、-C≡C-、-CF2O- or-COO-.
Alternatively, in formula (II), R3With R4The alkenyl of F, the alkyl of carbon number 1 to 10 or carbon number 2 to 10 can be respectively stood alone as,
A1With A21 or 4 cyclohexylidene or Isosorbide-5-Nitrae-phenylene, Z can respectively be stood alone as1It can be singly-bound or-C ≡ C.Or at formula (II)
In, R3With R4The alkyl of carbon number 1 to 10 or the alkenyl of carbon number 2 to 10, A can respectively be stood alone as1With A2It can be 1 or 4 cyclohexylidene, Z1
It can be singly-bound.
Alternatively, in formula (III), R5With R6The alkenyl of F, the alkyl of carbon number 1 to 10 or carbon number 2 to 10 can be respectively stood alone as,
R5With R6In arbitrary H can be replaced by F, and R5With R6In arbitrary-CH2It can be replaced by-O-, A3、A4With A5It can respectively stand alone as
2, the 5- indanyl of 1 or 4 cyclohexylidene, Isosorbide-5-Nitrae-phenylene or divalent, and A3、A4With A5In arbitrary H can be replaced by F, Z2With Z3
Singly-bound ,-CH can respectively be stood alone as2-、-CH2O-、-C2H4-、-C≡C-、-CF2O- or-COO-.
Alternatively, in formula (IV), R7With R8The alkenyl of F, the alkyl of carbon number 1 to 10 or carbon number 2 to 10 can be respectively stood alone as,
R7With R8In arbitrary H can be replaced by F, and R7With R8In arbitrary-CH2It can be replaced by-O-, A6、A7、A8With A9It can be respectively independent
For 2, the 5- indanyl of 1 or 4 cyclohexylidene, Isosorbide-5-Nitrae-phenylene, 1,3- cyclopentylene or divalent, and A6、A7、A8With A9In it is any
H can be replaced by F, Z4、Z5With Z6Singly-bound or-CF can respectively be stood alone as2O-。
For example, the compound of formula (II) can be but be not limited to structure such as formula (II-1) to formula (II-17) shown in any one
Compound:
Above-mentioned formula (II-1) to formula (II-17) compound represented can be used alone, and also can be used simultaneously two or more.
For example, formula (III) compound can be but be not limited to structure such as formula (III-1) to formula (III-33) shown in any one
Compound:
Above-mentioned formula (III-1) to formula (III-33) compound represented can be used alone, and also can be used simultaneously two or more.
For example, formula (IV) compound can be but be not limited to structure such as formula (IV-1) to formula (IV-9) chemical combination shown in any one
Object:
Above-mentioned formula (IV-1) to formula (IV-9) compound represented can be used alone, and also can be used simultaneously two or more.
Liquid-crystal composition above-mentioned can further include structure such as formula (II), formula (III) and formula (IV) compound represented
At least one, refer to that liquid-crystal composition can be only comprising in structure such as formula (II), formula (III) and formula (IV) compound represented
One kind, also can be simultaneously comprising two kinds therein or more kinds of.
Liquid-crystal composition above-mentioned can include structure such as formula (II), formula (III) and formula (IV) compound represented, base simultaneously
It is 100 weight percent in the content of the liquid-crystal composition, which may include 0.1 weight percent to 25 weight hundred
Divide the liquid-crystal compounds of ratio, formula (II) compound, 15 weight percent to 75 weights of 5 weight percent to 75 weight percent
Measure formula (III) compound of percentage and formula (IV) compound of 1 weight percent to 50 weight percent.
It can include selectively further additive, additive can be dopant or stabilization in foregoing liquid crystal composition
Agent.The additive can be but be not limited to structure such as formula (V-1) to formula (V-14) any one compound represented:
Liquid crystal display element
Liquid crystal display element of the invention includes liquid-crystal composition above-mentioned.About liquid-crystal composition please refer to above,
In addition this is not repeated, structure and the manufacturing method of liquid crystal display element be it is as known in the art, in addition do not repeat herein.
Embodiment
The synthesis of liquid-crystal compounds
The present invention will be further illustrated with embodiment below, will be used however, it should be noted that embodiment only illustrates, and
It is not necessarily to be construed as the limitation to implementation of the invention.
The liquid-crystal compounds of formula (I-1): the liquid-crystal compounds of formula (I-1) can be obtained using method shown in synthesis flow 1,
Synthesis flow 1.
First stage reaction, the synthesis of 3- propyl cyclopentanol (3-propylcyclopentanol, compound 1): will
The 3- propyl-cyclopentanone (3-propylcyclopentanone) of 5.04g (40mmol) is placed in the mono- neck bottle of 250mL, adds four
Hydrogen furans (tetrahydrofuran, THF) is simultaneously uniformly mixed to form a solution.The solution is moved on to containing 0.76g (20mmol)
Lithium aluminium hydride (lithium aluminium hydride, LAH) and the 250mL two-neck bottle of anhydrous tetrahydro furan in, in nitrogen
Ice bath reacts 1 hour under environment.After the reaction was completed, distilled water is slowly dropped into two-neck bottle, until reactant is creamy white, benefit
It is filtered to remove solid with pumping, collects filtrate, extracts filtrate with ethyl acetate and distilled water, is removed followed by instrument is concentrated under reduced pressure
Solvent obtains the compound 1 of 4.86g, yield 95%.
Second stage reaction, formula (I-1) liquid-crystal compounds synthesis: by compound 1, the 2.09g of 1.28g (10mmol)
4- ethyoxyl -2,3- the difluorophenol (4-ethoxy-2,3-difluoro-phenol) and 3.93g (15mmol) of (12mmol)
Triphenylphosphine (triphenylphosphine, PPh3) be placed in 250mL two-neck bottle, it adds tetrahydrofuran and uniformly mixes
Afterwards, in a nitrogen environment, it reacts 15 minutes at room temperature, the azoformic acid diisopropyl of 3.03g (15mmol) is slowly added dropwise later
Ester (diisopropyl azodicarboxylate, DIAD) is in two-neck bottle, then at reaction 14 hours at room temperature.Reaction is completed
Afterwards, product is left so that instrument removing solvent is concentrated under reduced pressure, a small amount of methylene chloride is added and dissolves product to form a solution, then this is molten
Liquid slowly instills in the n-hexane of 10 times of amounts so that solid is precipitated, and is filtered to remove solid followed by pumping, collects filtrate, using subtracting
Press concentrating instrument remove filtrate in solvent, then with column chromatography purifying (purging with liquid proportional is ethyl acetate: n-hexane=1:
5) product of 1.42g, yield 50%, by product with high-resolution mass spectrometer (high resolution mass, are obtained
Spectrometry) and nuclear magnetic resonance spectrometer (Nuclear Magnetic Resonance, NMR) measures, can be true
Recognize errorless (the MS m/z:248 [M] of liquid-crystal compounds that product is formula (I-1)+；1H-NMR(400MHz,CDC13): δ 6.450-
6.65 (m, 2H), δ 4.11-4.32 (m, 1H), δ 3.87 (t, 2H), δ 1.56-1.67 (m, 4H), δ 1.08-1.52 (m, 6H), δ
0.89-1.02 (m, 3H), δ 0.72-0.94 (m, 4H)).
The liquid-crystal compounds of formula (I-2): the 2.09g in the second stage reaction of the liquid-crystal compounds of formula (I-1) will be synthesized
4- ethyoxyl -2,3- the difluorophenol (4-ethoxy-2,3-difluoro-phenol) of (12mmol) is changed to 2.26g
4- propoxyl group -2,3- difluorophenol (4-propoxy-2,3-difluoro-phenol) of (12mmol), remaining step all with formula
(I-1) synthetic method of liquid-crystal compounds is identical, and the product of 1.99g, yield 66%, by product with high resolution mass spectrum can be obtained
Instrument and NMR instrument measure, and can confirm that product is errorless (the MS m/z:248 [M] of liquid-crystal compounds of formula (I-2)+；1H-NMR
(400MHz,CDC13): δ 6.50-6.70 (m, 2H), δ 4.00-4.20 (m, 1H), δ 3.91 (t, 2H), δ 1.68-1.72 (m,
4H), δ 1.18-1.50 (m, 8H), δ 1.00 (t, 3H), δ 0.7-0.96 (m, 4H)).
The liquid-crystal compounds of formula (I-3): the 2.09g in the second stage reaction of the liquid-crystal compounds of formula (I-1) will be synthesized
4- ethyoxyl -2,3- the difluorophenol (4-ethoxy-2,3-difluoro-phenol) of (12mmol) is changed to 2.42g
4- butoxy -2,3- difluorophenol (4-butoxy-2,3-difluoro-phenol) of (12mmol), remaining step all with formula
(I-1) synthetic method of liquid-crystal compounds is identical, and the product of 1.99g, yield 64%, by product with high resolution mass spectrum can be obtained
Instrument and NMR instrument measure, and can confirm that product is errorless (the MS m/z:298 [M] of liquid-crystal compounds of formula (I-3)+；1H-NMR
(400MHz,CDC13): δ 6.44-6.74 (m, 2H), δ 4.60-4.80 (m, 1H), δ 3.90-4.02 (m, 2H), δ 1.68-1.82
(m, 4H), δ 1.52-1.62 (m, 2H), δ 1.20-1.42 (m, 7H), δ 1.06-1.20 (m, 1H), δ 0.92-1.06 (m, 3H), δ
0.7-0.92(m,4H))。
The synthesis of the liquid-crystal compounds of formula (I-4): it will synthesize in the second stage reaction of the liquid-crystal compounds of formula (I-1)
4- ethyoxyl -2,3- the difluorophenol (4-ethoxy-2,3-difluoro-phenol) of 2.09g (12mmol) is changed to 1.46g
2, the 3- difluoro hydroquinone (2,3-difluoro-hydroquinone) of (5mmol), liquid of remaining step all with formula (I-1)
The synthetic method of brilliant compound is identical, and the product of 0.62g can be obtained, and yield 34% surveys product with high-resolution mass spectrometer
Amount can confirm that product is errorless (the MS m/z:366 [M] of liquid-crystal compounds of formula (I-4)+)。
Liquid-crystal compounds/liquid-crystal composition evaluation method
Following prepare liquid can be liquid-crystal compounds or liquid-crystal composition.
Clearing point temperature (Tni, DEG C): differential scanning calorimeter (DSC) system is used, prepare liquid is placed in aluminium dish smart scale
0.5 to 10mg, the starting point of the endothermic peak and exothermic peak that occur by prepare liquid by phase change determines phase change temperature.Phase
The representation of variation are as follows: crystalline phase is denoted as C, and smectic phase is denoted as S, and nematic phase is denoted as N, and liquid is denoted as I.Wherein,
It is clearing point temperature (Tni) by the phase transition temperature of nematic phase to liquid.
Dielectric anisotropy (Δ ε): prepare liquid is fitted into liquid crystal cell, at a temperature of 25 DEG C, is applied to the liquid crystal cell
The voltage of 0V to 30V is ε ‖ being parallel to average dielectric constant measured by long axis of liquid crystal molecule direction, perpendicular to liquid crystal molecule
Average dielectric constant measured by long axis is ε ⊥, dielectric anisotropy (Δ ε)=ε ‖-ε ⊥.
Rotary viscosity (γ 1, mPaS): prepare liquid is fitted into liquid crystal cell, at a temperature of 25 DEG C, is applied to the liquid crystal cell
The voltage for adding 30V is added the conversion of dielectric anisotropy (Δ ε) factor through instrument, rotary viscosity γ 1 can be obtained.
Refractive anisotrop (Δ n): using be equipped on an eyepiece polarizer Abbe (Abbe) refractometer (manufacturer:
ATAGO；Model: DR-M2), prepare liquid is measured.Firstly, wiping the headprism surface of Abbe refractometer in one direction, connect
A small amount of prepare liquid is added dropwise on headprism, then under 25 DEG C of test temperature, using wavelength be 589nm optical filtering mating plate
Carry out the measurement of refractive anisotrop.When polarization direction is parallel with wiping direction, the refractive index measured is n ‖；When polarisation side
To it is vertical with wiping direction when, the refractive index that measures is n ⊥；Refractive anisotrop (Δ n)=n ‖-n ⊥.
The evaluation result of liquid-crystal compounds
By liquid-crystal compounds (I-1) of the invention~liquid-crystal compounds (I-4) and the liquid-crystal compounds (R- of comparative example
1)~liquid-crystal compounds (R-5) carries out the measurement such as Δ ε, ε ⊥ and Δ n, and records the result in table 1.
Liquid-crystal compounds (R-1)~liquid-crystal compounds (R-5) structural formula is as shown in table 2.
As shown in Table 1, liquid crystal of liquid-crystal compounds of the invention (the I-1)~liquid-crystal compounds (I-4) compared to comparative example
Compound (R-1)~liquid-crystal compounds (R-5) has lower dielectric anisotropy and higher vertical dielectric constant.
The embodiment and comparative example of liquid-crystal composition
Prepare the liquid-crystal composition of Examples 1 to 3.Liquid-crystal composition about Examples 1 to 3 at being respectively in table three,
The property measurement results of liquid-crystal composition about Examples 1 to 3 are listed in table four.
As shown in Table 4, liquid-crystal compounds according to the present invention can be used for deploying negative type liquid crystal composition, advantageously reduce
The dielectric anisotropy of liquid-crystal composition and the vertical dielectric constant for improving liquid-crystal composition, and then liquid crystal combination can be reduced
The driving voltage of object, and promote the transmissivity of liquid crystal display element.
Although the present invention is disclosed above with embodiment, however, it is not to limit the invention, those skilled in the art
Without departing from the spirit and scope of the present invention, when can make it is various change and retouch, therefore protection scope of the present invention
When being subject to appended claims institute defender.
Claims (14)
1. a kind of liquid-crystal compounds has the structure as shown in formula (I):
Wherein R1With R2The alkynyl of the alkyl of carbon number 1 to 10, the alkenyl of carbon number 2 to 10 or carbon number 2 to 10 is respectively stood alone as, wherein
R1With R2In arbitrary H can be replaced by F, n and m respectively stand alone as 0 or 1, and n+m=1 or n+m=2.
2. liquid-crystal compounds as described in claim 1, wherein R1With R2The alkyl of carbon number 1 to 5 is respectively stood alone as, n and m is respectively
Stand alone as 0 or 1, and n+m=1.
3. liquid-crystal compounds as described in claim 1 has such as formula (I-1), formula (I-2), formula (I-3) or formula (I-4) institute
The structure shown:
4. a kind of liquid-crystal composition, it includes liquid-crystal compounds as described in claim 1.
5. liquid-crystal composition as claimed in claim 4, wherein in formula (I), R1With R2Respectively stand alone as the alkane of carbon number 1 to 5
Base, n and m respectively stand alone as 0 or 1, and n+m=1.
6. liquid-crystal composition as claimed in claim 4, wherein the liquid-crystal compounds has such as formula (I-1), formula (I-2), formula (I-
Or structure shown in formula (I-4) 3):
7. liquid-crystal composition as claimed in claim 4, wherein the content based on the liquid-crystal composition is 100 weight %, the liquid
The content of brilliant compound is 0.1 weight % to 35 weight %.
8. liquid-crystal composition as claimed in claim 4 is further included as shown in formula (II), formula (III) and formula (IV)
At least one of compound:
R3–A1–Z1–A2-R4(II)；
R5–A3–Z2–A4–Z3–A5–R6(III)；
R7–A6–Z4–A7–Z5–A8–Z6–A9–R8(IV)；
Wherein R3、R4、R5、R6、R7With R8Respectively stand alone as the alkenyl of F, the alkyl of carbon number 1 to 10 or carbon number 2 to 10, R3、R4、R5、
R6、R7With R8In arbitrary H can be replaced by F, and R3、R4、R5、R6、R7With R8In arbitrary-CH2It can be replaced by-O-；
Wherein A1、A2、A3、A4、A5、A6、A7、A8With A9Respectively stand alone as 1,4- cyclohexylidene, 1,4- phenylene, the Asia 1,3- ring penta
Bicyclic [2.2.2] octyl of dioxa-, bicyclic [2.2.2] octyl of trioxa-of divalent or the 2,5- of divalent of base, divalent
Indanyl, and A1、A2、A3、A4、A5、A6、A7、A8With A9In arbitrary H can be replaced by F, alkyl or alkoxy；And
Wherein Z1、Z2、Z3、Z4、Z5With Z6Respectively stand alone as singly-bound ,-CH2-、-CH2O-、-C2H4-、-C≡C-、-CF2O- or-
COO-。
9. liquid-crystal composition as claimed in claim 8, wherein in formula (II), R3With R4Respectively stand alone as the alkane of F, carbon number 1 to 10
The alkenyl of base or carbon number 2 to 10, A1With A2Respectively stand alone as 1 or 4 cyclohexylidene or Isosorbide-5-Nitrae-phenylene, Z1For singly-bound or-C ≡ C-；
Wherein in formula (III), R5With R6Respectively stand alone as the alkenyl of F, the alkyl of carbon number 1 to 10 or carbon number 2 to 10, R5With R6In appoint
The H of meaning can be replaced by F, and R5With R6In arbitrary-CH2It can be replaced by-O-, A3、A4With A5Respectively stand alone as the Asia 1,4- hexamethylene
2, the 5- indanyl of base, Isosorbide-5-Nitrae-phenylene or divalent, and A3、A4With A5In arbitrary H can be replaced by F, Z2With Z3Respectively stand alone as
Singly-bound ,-CH2-、-CH2O-、-C2H4-、-C≡C-、-CF2O- or-COO-；And
Wherein in formula (IV), R7With R8Respectively stand alone as the alkenyl of F, the alkyl of carbon number 1 to 10 or carbon number 2 to 10, R7With R8In appoint
The H of meaning can be replaced by F, and R7With R8In arbitrary-CH2It can be replaced by-O-, A6、A7、A8With A9Respectively stand alone as the Asia 1,4- ring
Hexyl, Isosorbide-5-Nitrae-phenylene, 1,3- cyclopentylene or divalent 2,5- indanyl, and A6、A7、A8With A9In arbitrary H can be taken by F
Generation, Z4、Z5With Z6Respectively stand alone as singly-bound or-CF2O-。
10. liquid-crystal composition as claimed in claim 8, wherein in formula (II), R3With R4Respectively stand alone as the alkane of carbon number 1 to 10
The alkenyl of base or carbon number 2 to 10, A1With A2For 1 or 4 cyclohexylidene, Z1For singly-bound.
11. liquid-crystal composition as claimed in claim 8 includes shown in structure such as formula (II), formula (III) and formula (IV) simultaneously
Compound.
12. liquid-crystal composition as claimed in claim 11, wherein the content based on the liquid-crystal composition is 100 weight %, it should
Liquid-crystal composition includes:
The liquid-crystal compounds of 0.1 weight % to 25 weight %；
Formula (II) compound of 5 weight % to 75 weight %；
Formula (III) compound of 15 weight % to 75 weight %；And
Formula (IV) compound of 1 weight % to 50 weight %.
13. liquid-crystal composition as claimed in claim 4, further includes additive.
14. a kind of liquid crystal display element, it includes the liquid-crystal compositions as described in any one of claim 4 to 13.
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| TW201914988A (en) | 2019-04-16 |
| CN109575936B (en) | 2020-11-03 |
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