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WO2018107911A1 - Composé à cristaux liquides présentant une anisotropie diélectrique négative et application associée - Google Patents

Composé à cristaux liquides présentant une anisotropie diélectrique négative et application associée Download PDF

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Publication number
WO2018107911A1
WO2018107911A1 PCT/CN2017/108000 CN2017108000W WO2018107911A1 WO 2018107911 A1 WO2018107911 A1 WO 2018107911A1 CN 2017108000 W CN2017108000 W CN 2017108000W WO 2018107911 A1 WO2018107911 A1 WO 2018107911A1
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Prior art keywords
liquid crystal
substituted
group
carbon atoms
compound
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Ceased
Application number
PCT/CN2017/108000
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English (en)
Chinese (zh)
Inventor
韩文明
徐爽
徐海彬
陈昭远
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.)
Jiangsu Hecheng Display Technology Co Ltd
Original Assignee
Jiangsu Hecheng Display Technology Co Ltd
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
Priority claimed from CN201710038731.9A external-priority patent/CN108203583B/zh
Application filed by Jiangsu Hecheng Display Technology Co Ltd filed Critical Jiangsu Hecheng Display Technology Co Ltd
Publication of WO2018107911A1 publication Critical patent/WO2018107911A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-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
    • 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
    • C09K19/42—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
    • 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
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL 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
    • G02F1/00—Devices 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
    • G02F1/01—Devices 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 
    • G02F1/13—Devices 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
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods

Definitions

  • the present invention relates to a liquid crystal compound, particularly a liquid crystal compound having negative dielectric anisotropy and use thereof.
  • the liquid crystal display element can be used in various household electric appliances, measuring machines, automobile panels, word processors, computers, printers, televisions, and the like represented by watches and clocks and electronic calculators.
  • PC phase change
  • TN tunnel nematic
  • STN super twisted nematic
  • ECB electrically controlled
  • Birefringence electronically controlled birefringence
  • OCB optical compensated bend
  • IPS in-plane switching
  • VA vertical alignment
  • CSH color super homeotropic
  • the PM is divided into static (static) and multiplex (multiplex) types.
  • the AM is classified into a TFT (thin film transistor), a MIM (metal insulator metal), and the like.
  • the types of TFTs are amorphous silicon and polycrystalline silicon. The latter is classified into a high temperature type and a low temperature type according to a manufacturing process.
  • the liquid crystal display element is classified into a reflection type using natural light, a transmission type using a backlight, and a semi-transmissive type using both natural light and backlight depending on the type of the light source.
  • the IPS mode, the ECB mode, the VA mode, or the CSH mode are different from the conventional TN mode or the STN mode in that the former uses a liquid crystal material having a negative dielectric anisotropy.
  • an AM-driven VA-type display is used in a display element requiring a high-speed and wide viewing angle, and among them, the most desirable one is application to a liquid crystal element such as a television.
  • the liquid crystal material used is required to have a low driving voltage, a high response speed, a wide operating temperature range, a large absolute value of negative dielectric anisotropy, a high phase transition temperature, and good mutual solubility.
  • a highly conjugated molecular structure has a tendency to be inferior in compatibility with other liquid crystal materials, and is difficult to be used as a constituent element of a liquid crystal composition having good electrical characteristics.
  • a liquid crystal compound used as a constituent element of a liquid crystal composition requiring light stability such as a liquid crystal display device of a thin film transistor type is required to have high stability.
  • a liquid crystal display element containing a liquid crystal composition having a large absolute value of dielectric anisotropy can lower the basic voltage value, lower the driving voltage, and further reduce the power consumption.
  • a large number of hydrogen-substituted liquid crystal compounds on a benzene ring have been studied for a long time as a component of a liquid crystal composition having a negative dielectric anisotropy which can be used for a liquid crystal display element.
  • the side fluorine-containing negative compounds such as Ref.2 and Ref.3 avoid the disadvantages of the bis-cyano-negative compound, the negative dielectric anisotropy value is too small (Ref. 2 dielectric anisotropy literature). The value is -4.1, and the Ref. 3 dielectric anisotropy literature value is -6.0). Therefore, compounds with large negative dielectric side fluorine species still need to be explored.
  • liquid crystal host compositions and RM (reactive mesogen) materials disclosed in the prior art still have some drawbacks when used in PSA displays. Therefore, not every soluble RM material is suitable for PSA displays, and it is often difficult to find a more suitable selection criterion than direct PSA testing with pre-tilt measurements. When it is desired to polymerize by means of UV light without the addition of a photoinitiator, which may be advantageous for certain applications, the liquid crystal host composition selection becomes smaller.
  • Prior art PSA displays often exhibit an undesirable "image sticking" effect in which an image produced in the display is made visible by addressing selected pixels even when the voltage for that pixel has been turned off or when When other pixels have been addressed.
  • the ambient light or the UV component of the light emitted by the backlight causes spontaneous polymerization of the unreacted RM material.
  • this may change the tilt angle after several address periods, thereby causing a change in transmittance, while in unaddressed pixels, the tilt angle and transmittance remain unaffected.
  • Another object of the present invention is to provide a method of synthesizing the above liquid crystal composition.
  • Still another object of the present invention is to provide a liquid crystal composition comprising the above liquid crystal compound and a display comprising the liquid crystal composition.
  • the present invention provides a compound having a negative dielectric anisotropy, the compound having the structure of Formula I:
  • the R 1 independently represents a substituted or unsubstituted linear or branched alkyl group of 1 to 10 carbon atoms, and a substituted or unsubstituted linear or branched alkenyl group of 2 to 10 carbon atoms;
  • the R 2 independently represents a substituted or unsubstituted linear or branched alkyl or alkoxy group of 1 to 10 carbon atoms, and a substituted or unsubstituted linear or branched chain of 2 to 10 carbon atoms Alkenyl or alkenyloxy, wherein one or more -CH 2 - may be substituted by -O-, provided that the oxygen atoms are not directly attached;
  • the ring A represents a 1,4-phenylene group or a 1,4-cyclohexylene group
  • the m represents a positive integer of 1-12;
  • n 0 or 1
  • the p represents 0, 1, or 2.
  • R 1 independently represents a substituted or unsubstituted straight or branched alkyl group of 1 to 6 carbon atoms, substituted or unsubstituted 2 to 6 carbon atoms Linear or branched alkenyl.
  • the m represents a positive integer from 1 to 6.
  • the m represents a positive integer of 2-6.
  • the m represents a positive integer of 3-6.
  • R 2 independently represents a substituted or unsubstituted linear or branched alkyl group of 1 to 6 carbon atoms, 2 to 6 carbons.
  • the compound of Formula I is selected from the group consisting of the following compounds of Formulas I-1 to I-4:
  • the R 1 and R 2 each independently represent a substituted or unsubstituted linear or branched alkyl group of 1 to 6 carbon atoms, and a substituted or unsubstituted linear or branched chain of 2 to 6 carbon atoms Alkenyl.
  • the compound of Formula 1-1 is preferably selected from the group consisting of:
  • the R 1 represents a substituted or unsubstituted linear or branched alkyl group of 1 to 6 carbon atoms, and a substituted or unsubstituted linear or branched alkenyl group of 2 to 6 carbon atoms.
  • the compound of Formula 1-2 is preferably selected from the group consisting of:
  • the R 1 represents a substituted or unsubstituted linear or branched alkyl group of 1 to 6 carbon atoms, and a substituted or unsubstituted linear or branched alkenyl group of 2 to 6 carbon atoms.
  • the compound of Formula I-3 is preferably selected from the group consisting of:
  • the R 1 represents a substituted or unsubstituted linear or branched alkyl group of 1 to 6 carbon atoms, and a substituted or unsubstituted linear or branched alkenyl group of 2 to 6 carbon atoms.
  • the compound of Formula 1-4 is preferably selected from the group consisting of:
  • the R 1 represents a substituted or unsubstituted linear or branched alkyl group of 1 to 6 carbon atoms, and a substituted or unsubstituted linear or branched alkenyl group of 2 to 6 carbon atoms.
  • Another aspect of the present invention provides a liquid crystal composition comprising the liquid crystal compound of the formula I of the present invention.
  • the liquid crystal composition further comprises one or more compounds of Formula II and/or one or more compounds of Formula III:
  • the R 3 , R 4 , R 5 and R 6 each independently represent -H, -F, a substituted or unsubstituted linear or branched alkyl or alkoxy group of 1 to 10 carbon atoms, 2 a substituted or unsubstituted linear or branched alkenyl or alkenyloxy group of 10 carbon atoms, wherein one or more -CH 2 - may be substituted by -O-, provided that the oxygen atoms are not directly linked;
  • the ring A, ring B and ring C each independently represent a 1,4-cyclohexyl group, a 1,4-phenylene group, wherein one or more non-adjacent Hs in the 1,4-phenylene group may be F substituted, one or more non-adjacent -CH 2 - in 1,4-cyclohexyl may be substituted by -O-;
  • the a represents 0, 1, or 2, wherein when a represents 0, ring A and ring B are not simultaneously 1,4-cyclohexyl.
  • the liquid crystal composition further comprises
  • the R 7 and R 8 each independently represent -H, -F, a substituted or unsubstituted linear or branched alkyl or alkoxy group of 1 to 10 carbon atoms, and a substitution of 2 to 10 carbon atoms. Or unsubstituted linear or branched alkenyl or alkenyloxy, wherein one or more -CH 2 - may be substituted by -O-, provided that the oxygen atoms are not directly attached;
  • the ring D and the ring E each independently represent a 1,4-cyclohexyl group, a 1,4-phenylene group, wherein one or more of H in the 1,4-phenylene group may be substituted by F, 1,4- One or more non-adjacent -CH 2 - in the cyclohexyl group may be substituted by -O-;
  • the c represents 0 or 1.
  • the liquid crystal composition further comprises
  • R, R 9 and R 10 each independently represent -H, an alkyl group having 1 to 7 carbon atoms or an alkoxy group;
  • the Y 1 and Y 2 each independently represent a single bond, an acetylenic bond, an alkylene group of 1 to 4 carbon atoms, -O-, -COO-, -OCO-, -OCOO-, -CH 2 O- or - OCH 2 -;
  • the X 1 and X 2 each independently represent a single bond, -O-, -COO-, -OCO- or -OCOO-;
  • the m 1 and m 2 each independently represent an integer of 1-6;
  • the d represents 0 or 1.
  • the R independently represents -H, -CH 3, -CH 2 CH 3 or -CH 2 CH 2 CH 3.
  • R 9 and R 10 each independently represent -H or -CH 3 .
  • the Y 1 and Y 2 each independently represent a single bond, -O-, -COO-, -OCO-, -OCOO-, -CH 2 O- or -OCH 2 -, preferably It is a single bond, -O-, -COO-, -OCO- or -OCOO-.
  • X 1 and X 2 each independently represent a single bond, —O—, —COO— or —OCO—.
  • Another aspect of the present invention provides a display device comprising the liquid crystal composition of the present invention.
  • Another aspect of the present invention provides an application of the liquid crystal composition of the present invention in VA, FFS, IPS, PSVA display modes.
  • the liquid crystal compound having the general formula I provided by the present invention has a large absolute value of dielectric anisotropy, high optical anisotropy, high-definition bright spot, and low compared with other negative liquid crystal compounds of the prior art.
  • the polymerizable liquid crystal composition containing the liquid crystal compound has a dielectric value of a large absolute value Anisotropy, low threshold voltage, fast response speed, high contrast, good mutual solubility, and good light stability and low temperature stability, while including the polymerizable liquid crystal composition exhibiting little or no image sticking Effect; and the preparation process of the liquid crystal compound of the formula I of the invention, the raw material is easy to obtain, the synthesis route is simple and easy, and is suitable for large-scale industrial production.
  • the refractive index anisotropy was measured at 25 ° C under a sodium light (589 nm) light source using an Abbe refractometer; the dielectric test box was a TN90 type, and the cell thickness was 7 ⁇ m.
  • ⁇ ⁇ - ⁇ , where ⁇ is the dielectric constant parallel to the molecular axis, ⁇ is the dielectric constant perpendicular to the molecular axis, test conditions: 25°C, 1KHz, test box is TN90 type, box thickness 7 ⁇ m.
  • Afterimage level test continuously drive the display element with 16V voltage, at a fixed time point, observe whether the residual image of the fixed image reaches an unacceptable level; if the residual image of the fixed image has reached an unacceptable level at the observation time point, it is recorded as IS ⁇ "this observation time point", if the residual image of the fixed image does not reach an unacceptable level at the observation time point, it is recorded as IS > "this observation time point”.
  • the fixed observation time points were: 24 hours, 168 hours, 240 hours, 500 hours, and 1000 hours.
  • liquid crystal compounds of the general formula I prepared by the following examples were tested for optical anisotropy and clearing points and the extrapolation parameters were determined as follows:
  • the commercial liquid crystal No. TS023 produced by Jiangsu Hecheng Display Technology Co., Ltd. was selected as the precursor, and the liquid crystal compound represented by Formula I was dissolved in the parent liquid crystal (10% by weight) to test the optical anisotropy of the mixture. Clearing point and dielectric anisotropy, and liquid crystal performance data of the liquid crystal compound represented by Formula I was extrapolated according to a linear relationship according to the ratio added in the matrix.
  • the parent liquid crystal (host) is obtained by mixing the following compounds in a ratio of 20%:40%:40%:
  • the compound represented by the following Table 2 can be converted by the compound C and the compound A to obtain the target compound:
  • liquid crystal properties of the above target compounds are as follows:
  • Example 1 Data for representative compounds of the compound of the formula I-1 are provided in Example 1, by the liquid crystal compounds I-1-10, I-1-6, I-1-2-1 and I in Example 1. As can be seen from the data of -1-2-2, the liquid crystal compound of the formula I-1 has a large absolute value of dielectric anisotropy and a high optical anisotropy.
  • the compound represented by the following Table 3 can be converted by the compound C and the compound A to obtain the target compound:
  • liquid crystal properties of the above target compounds are as follows:
  • Example 2 The data of a representative compound of the compound of the formula I-4 is provided in Example 2, and the data of the liquid crystal compounds I-4-6, I-4-7 and I-4-8 in Example 2 can be seen.
  • the liquid crystal compound of the formula I-4 has a large absolute value of dielectric anisotropy, a high optical anisotropy and a suitably high clearing point.
  • the liquid crystal compositions of Comparative Example 1 were prepared according to the respective compounds and weight percentages listed in Table 4, and were filled in the performance test between the two substrates of the liquid crystal display.
  • the test data are shown in the following table:
  • Example 3 The liquid crystal composition of Example 3 was prepared according to each compound and weight percentage listed in Table 5, and was filled in the performance test between the two substrates of the liquid crystal display.
  • the test data is shown in the following table:
  • Example 4 The liquid crystal composition of Example 4 was prepared according to each compound and weight percentage listed in Table 6, and was filled in the performance test between the two substrates of the liquid crystal display. The test data are shown in the following table:
  • the compound of the present invention has a large absolute value of dielectric anisotropy, a suitably high clearing point, and a suitably high optical anisotropy, and can be applied to a liquid crystal composition. .
  • the liquid crystal compound according to the present invention can be applied to the field of liquid crystals.

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Liquid Crystal Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un composé à cristaux liquides de formule (I) ayant une anisotropie diélectrique négative, le composé à cristaux liquides ayant une grande valeur absolue d'anisotropie diélectrique, une anisotropie optique élevée, des points brillants à haute définition, une faible viscosité, une vitesse de réponse rapide, une rétention de tension élevée, une bonne miscibilité, et une bonne stabilité optique et une bonne stabilité à basse température. Le procédé de préparation du composé à cristaux liquides de formule (I) de la présente invention a des matières premières pouvant être obtenues facilement et une voie de synthèse simple et facile à mettre en oeuvre, et est approprié pour une production industrielle à grande échelle; la présente invention concerne également une composition à cristaux liquides contenant le composé de cristaux liquides, la composition de cristaux liquides ayant de bonnes performances de cristaux liquides.
PCT/CN2017/108000 2016-12-16 2017-10-27 Composé à cristaux liquides présentant une anisotropie diélectrique négative et application associée Ceased WO2018107911A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CN201611169025 2016-12-16
CN201611169025.X 2016-12-16
CN201710038731.9A CN108203583B (zh) 2016-12-16 2017-01-19 具有负介电各向异性的液晶化合物及其应用
CN201710038731.9 2017-01-19

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112048313A (zh) * 2019-06-06 2020-12-08 江苏和成显示科技有限公司 一种液晶组合物及其液晶显示器件
US11634640B2 (en) * 2017-09-28 2023-04-25 Jiangsu Hecheng Display Technology Co., Ltd. Liquid crystal composition and liquid crystal display device having same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4434975A1 (de) * 1994-09-30 1996-04-04 Hoechst Ag Tricyclische Verbindungen und ihre Verwendung in flüssigkristallinen Mischungen
WO1996035674A1 (fr) * 1995-05-10 1996-11-14 Hoechst Aktiengesellschaft Derives de 1-fluoroisoquinoleine et leur utilisation dans des melanges de cristaux liquides
US20080063814A1 (en) * 2006-09-06 2008-03-13 Chisso Corporation Cyclohexene derivative having alkenyl, liquid crystal composition and liquid crystal display device
CN104263383A (zh) * 2014-10-10 2015-01-07 石家庄诚志永华显示材料有限公司 一种液晶介质及应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4434975A1 (de) * 1994-09-30 1996-04-04 Hoechst Ag Tricyclische Verbindungen und ihre Verwendung in flüssigkristallinen Mischungen
WO1996035674A1 (fr) * 1995-05-10 1996-11-14 Hoechst Aktiengesellschaft Derives de 1-fluoroisoquinoleine et leur utilisation dans des melanges de cristaux liquides
US20080063814A1 (en) * 2006-09-06 2008-03-13 Chisso Corporation Cyclohexene derivative having alkenyl, liquid crystal composition and liquid crystal display device
CN104263383A (zh) * 2014-10-10 2015-01-07 石家庄诚志永华显示材料有限公司 一种液晶介质及应用

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11634640B2 (en) * 2017-09-28 2023-04-25 Jiangsu Hecheng Display Technology Co., Ltd. Liquid crystal composition and liquid crystal display device having same
CN112048313A (zh) * 2019-06-06 2020-12-08 江苏和成显示科技有限公司 一种液晶组合物及其液晶显示器件
CN112048313B (zh) * 2019-06-06 2022-09-16 江苏和成显示科技有限公司 一种液晶组合物及其液晶显示器件

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