WO1997003146A1 - Liquid crystal composition - Google Patents

Liquid crystal composition Download PDF

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Publication number
WO1997003146A1
WO1997003146A1 PCT/EP1996/002860 EP9602860W WO9703146A1 WO 1997003146 A1 WO1997003146 A1 WO 1997003146A1 EP 9602860 W EP9602860 W EP 9602860W WO 9703146 A1 WO9703146 A1 WO 9703146A1
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WO
WIPO (PCT)
Prior art keywords
liquid crystal
crystal composition
composition according
nematic liquid
crown ether
Prior art date
Application number
PCT/EP1996/002860
Other languages
French (fr)
Inventor
Yoshiko Tsuruta
Yuji Nakazono
Atsushi Sawada
Ryoko Kimura
Kenichi Nishikawa
Keiko Kobayashi
Original Assignee
Merck Patent Gmbh
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 Merck Patent Gmbh filed Critical Merck Patent Gmbh
Priority to DE19681567T priority Critical patent/DE19681567B4/en
Priority to JP52976596A priority patent/JP4195083B2/en
Publication of WO1997003146A1 publication Critical patent/WO1997003146A1/en

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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
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58—Dopants or charge transfer agents
    • 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
    • C09K19/58—Dopants or charge transfer agents
    • C09K19/582—Electrically active dopants, e.g. charge transfer agents
    • C09K19/584—Electrically active dopants, e.g. charge transfer agents having a condensed ring system; macrocyclic compounds

Definitions

  • This invention relates to a nematic liquid crystal composition which exhibits a resistivity of at least 1 ⁇ 10 11 ⁇ cm, characterized in that it contains 1 to 10,000 ppm of a crown ether.
  • LCD liquid crystalline display devices
  • a LCD even may become breed ON state" due to the same electrostatic effect, if such a device is touched or rubbed by clothes in order to clean it.
  • the Japanese laid-open application JP 4-028-788 suggest to improve the electrostatic behavior of a LCD by reducing the specific resistivity of the liquid crystal by doping it with a cryptand.
  • the resulting liquid crystal compositions have specific resistivities of less than 1 ⁇ 10 10 ⁇ cm.
  • a method of reducing the sodium ions in LCD's by adding crown ethers to the liquid crystal is dislosed in the Japanese laid-open application JP 5-088-148.
  • the Japanese laid-open application JP 54-106-084 discloses that the crosstalk of multiplexed LCD's can be reduced by adding crown ethers or cryptands to the liquid crystal.
  • nematic liquid crystalline compositions with specific resistance of 1 ⁇ 10 11 ⁇ cm being doped with up to 10,000 ppm of a crown ether are suitable to reduce the electrostatic problems of a LCD.
  • nematic liquid crystal composition which exhibits a resistivity of at least 1 ⁇ 10 11 ⁇ cm, characterized in that it contains 1 to 10,000 ppm of a crown ether.
  • a further object of the invention is to provide a method of improving the electrostatic behavior of a LCD with the aid of such a composition.
  • the nematic liquid crystal composition according to the invention are preferably doped by a crown ether.
  • the expression crown ether in-dudes cyclic polyethers and the corresponding benzo derivatives. They are preferably cyclic compounds of formula A or B
  • n is an integer between 4 and 8, in particular a compound of formula Aa or Ba
  • nematic compositions according to the invention make it possible to achieve a high value for the specific resistance simultaneously accompanied by a fast discharge of the electrostatic charge, as a result of which outstanding LCD's can be achieved.
  • the specific resistivity of the inventive compositions is > 1 ⁇ 10 11 ⁇ cm, preferably between 2 ⁇ 10 11 and 1 ⁇ 10 14 ⁇ cm.
  • the discharge time depends on the amount of the added crown ether. As a rule, even only 1 ppm of the crown ether yields a reduction of the discharge time of at least 30 %, depending on the type of the un-doped composition the discharge time is reduced of 50 to 85 % with the aid of 1 ppm of the crown ether. Therefore, the content of the crown ether in the composition is preferably less than 10,000 ppm, preferably 1 to 1,000 ppm.
  • the invention is applied to nematic compositions for TN or STN devices, in particular for high threshold voltage TN-LCD's or active matrix LCD. Both these types of display preferably operate in the first transmission minimum as suggested by Gooch and Tarry (e.g. CH. Gooch, H.A. Tarry, Electron. Lett. 10, 2-4, 1974).
  • the birefringence ( ⁇ n) of the nematic compositions according to the invention is preferably 0.11 or less, in particular 0.07 to 0.105, most preferred 0.090 to 0.102.
  • the viscosity at 20 °C of the inventive compositions is preferably ⁇ 25 mPas.
  • the nematic phase range is preferably at least 70 °C, in particular at least 80 °C and extends at least from -20 ° to + 70 °C
  • the nematic composition as a rule contains at least 3 , preferably 5 to 20, in particular 8 to 15 mesogenic compounds.
  • the dielectric anisotropy ( ⁇ ) of the inventive compositions is as a rule higher than + 1.5.
  • ⁇ is between + 3.0 and + 10.0.
  • the threshold voltage of the compositions according to the invention is preferably smaller than 3,5 V, in particular smaller than 3.0 V.
  • the nematic liquid crystal composition according to the invention preferably contains at least one liquid crystalline compound of formula I and at least one compound of formula II,
  • R 1 , R 2 and R 3 are each independently alkyl, alkoxy or alkenyl with up to 12 C atoms,
  • X is -CN, F, Cl, -OCF 3 or -OCF 2 H
  • Z 1 and Z 2 are each independently -C ⁇ C-, -CH 2 CH 2 -, -COO- or
  • L 1 and L 2 each independently denote H or F
  • n 0 or 1
  • o 0, 1 or 2.
  • the nematic liquid crystal composition according to the invention contains at least one compound selected from formulae la to le and at least one compound selected from formulae IIa. IIb and IIe:
  • q 0 or 1
  • L 3 is H or F.
  • Another aspect of this invention is a method of improving the discharge time of an electrostatically charged liquid crystal display device with the aid of the inventive compositions.
  • Experiment A applying 10 kV by electrostatic discharge simulator
  • Experiment B applying 10V 10 seconds by a DC power supply
  • compositions of the mixtures of the Examples 1 to 10 is specified below, the individual compounds are coded as follows:
  • a nematic composition A is formulated comprising:
  • FIG. 1 The correlation of the discharge time and the concentration of the crown ether of Experiment A is shown in FIG. 1;
  • FIG. 2 gives the correlation between the specific resistivity and the discharge time.
  • a nematic composition B is formulated comprising:
  • a nematic composition C is formulated comprising:
  • FIG.1 Discharge time ( ⁇ dc ) as a function of the concentration of 18- Crown-6 in composition A with experiment A (Electrostatic discharge simulator, applied voltage 10 kV).
  • FIG.2 Discharge time ( ⁇ dc ) as a function of the specific resistivity in composition A with experiment A (Electrostatic discharge simulator, applied voltage 10 kV).
  • FIG.3 Discharge time ( ⁇ dc ) as a function of the specific resistivity in composition A ( - ⁇ - ) and B ( ) with experiment A (Electrostatic discharge simulator, applied voltage 10 kV).
  • FIG.4 Discharge time ( ⁇ dc ) as a function of the specific resistivity in composition A ( - ⁇ - ) and B ( ) with experiment B (DC 30V, applied 10 s).
  • FIG.5 Discharge time ( ⁇ dc ) as a function of the specific resistivity in composstion A ( - ⁇ - ) and B ( ) with experiment C (Rubbing with paper).

Abstract

The invention relates to a nematic liquid crystal composition which exhibits a resistivity of at least 1 x 1011 Φcm which contains 1 to 10,000 ppm of a crown ether and to a method of improving the electrostic behavior of a liquid crystal display device with the aid of such a composition.

Description

Liquid Crystal Composition
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a nematic liquid crystal composition which exhibits a resistivity of at least 1 × 1011 Ωcm, characterized in that it contains 1 to 10,000 ppm of a crown ether.
2. Description of the prior art
Liquid crystalline display devices (LCD) with liquid crystals having high resistivities suffer from the following problems:
• In the manufacturing process of LCD's, static electricity forms electric fields in the device for example when a protective film is peeled off from a polarizer. This electric field aligns the liquid crystalline compounds and the device becomes„ ON state". Therefore, the manufacturing of the display has to be interrupted until the electricity has been discharged.
• A LCD even may become„ ON state" due to the same electrostatic effect, if such a device is touched or rubbed by clothes in order to clean it.
It was an object of this invention to provide a solution for this disadvantage, i.e. to find a method to reduce the time of discharging a LCD without adversely affecting the resistivity of the liquid crystal.
The Japanese laid-open application JP 4-028-788 suggest to improve the electrostatic behavior of a LCD by reducing the specific resistivity of the liquid crystal by doping it with a cryptand. The resulting liquid crystal compositions have specific resistivities of less than 1 × 1010 Ωcm.
A method of reducing the sodium ions in LCD's by adding crown ethers to the liquid crystal is dislosed in the Japanese laid-open application JP 5-088-148. The Japanese laid-open application JP 54-106-084 discloses that the crosstalk of multiplexed LCD's can be reduced by adding crown ethers or cryptands to the liquid crystal.
There is no suggestion that nematic liquid crystalline compositions with specific resistance of 1 × 1011 Ωcm being doped with up to 10,000 ppm of a crown ether are suitable to reduce the electrostatic problems of a LCD.
SUMMARY OF THE INVENTION
Accordingly, it is an object of the invention to provide a nematic liquid crystal composition which exhibits a resistivity of at least 1 × 1011 Ωcm, characterized in that it contains 1 to 10,000 ppm of a crown ether.
A further object of the invention is to provide a method of improving the electrostatic behavior of a LCD with the aid of such a composition.
PREFERRED EMBODIMENTS
The nematic liquid crystal composition according to the invention are preferably doped by a crown ether. The expression crown ether in-dudes cyclic polyethers and the corresponding benzo derivatives. They are preferably cyclic compounds of formula A or B
[(CH2)2mO]m A,
[(CH2)2m-4O] m-2 ' (C6H4O)2 B,
in which m is an integer between 4 and 8, in particular a compound of formula Aa or Ba
Figure imgf000004_0001
The nematic compositions according to the invention make it possible to achieve a high value for the specific resistance simultaneously accompanied by a fast discharge of the electrostatic charge, as a result of which outstanding LCD's can be achieved.
The specific resistivity of the inventive compositions is > 1 × 1011 Ωcm, preferably between 2 × 1011 and 1 × 1014 Ωcm.
The discharge time depends on the amount of the added crown ether. As a rule, even only 1 ppm of the crown ether yields a reduction of the discharge time of at least 30 %, depending on the type of the un-doped composition the discharge time is reduced of 50 to 85 % with the aid of 1 ppm of the crown ether. Therefore, the content of the crown ether in the composition is preferably less than 10,000 ppm, preferably 1 to 1,000 ppm.
In principle, it is possible to add said crown ether to any kind of nematic composition. Preferably, the invention is applied to nematic compositions for TN or STN devices, in particular for high threshold voltage TN-LCD's or active matrix LCD. Both these types of display preferably operate in the first transmission minimum as suggested by Gooch and Tarry (e.g. CH. Gooch, H.A. Tarry, Electron. Lett. 10, 2-4, 1974). Accordingly, the birefringence (Δn) of the nematic compositions according to the invention is preferably 0.11 or less, in particular 0.07 to 0.105, most preferred 0.090 to 0.102.
The viscosity at 20 °C of the inventive compositions is preferably≤ 25 mPas. The nematic phase range is preferably at least 70 °C, in particular at least 80 °C and extends at least from -20 ° to + 70 °C
The nematic composition as a rule contains at least 3 , preferably 5 to 20, in particular 8 to 15 mesogenic compounds. The dielectric anisotropy (Δε) of the inventive compositions is as a rule higher than + 1.5. Preferably Δε is between + 3.0 and + 10.0.
The threshold voltage of the compositions according to the invention is preferably smaller than 3,5 V, in particular smaller than 3.0 V.
The nematic liquid crystal composition according to the invention preferably contains at least one liquid crystalline compound of formula I and at least one compound of formula II,
Figure imgf000006_0002
in which
R1, R2 and R3 are each independently alkyl, alkoxy or alkenyl with up to 12 C atoms,
X is -CN, F, Cl, -OCF3 or -OCF2H
the rings A, B, C and D each independently denote
1,4 cyclohexylene, 1 ,4-cyclohexenylene, 1 ,4-phenylene each of which being optionally substituted by one or two fluorine atoms, Z1 and Z2 are each independently -C≡C-, -CH2CH2-, -COO- or
a single bond,
L1 and L2 each independently denote H or F,
n is 0 or 1 , and
o is 0, 1 or 2.
In a particularly preferred embodiment the nematic liquid crystal composition according to the invention contains at least one compound selected from formulae la to le and at least one compound selected from formulae IIa. IIb and IIe:
Figure imgf000006_0001
Figure imgf000007_0001
in which R1, R2, R3, L1, L2, Z1 and the rings B and C have the meaning given in claim 5,
q is 0 or 1, and
L3 is H or F. Another aspect of this invention is a method of improving the discharge time of an electrostatically charged liquid crystal display device with the aid of the inventive compositions. EXAMPLES
Having generally described the invention, a more complete understanding can be obtained by reference to certain specific examples which are provided herein for purposes of illustration only and are not intended to be limiting unless otherwise spepified. In the following examples the temperature properties of the mesophases are indicated in the conventional way by giving the corresponding temperatures (° C). The investigations of the discharge time of the LCD's filed with the inventive compositions have been carried out in a twisted nematic cell (TN) having a cell gap of 5.7 μm using three different methods:
• Experiment A: applying 10 kV by electrostatic discharge simulator; • Experiment B: applying 10V 10 seconds by a DC power supply;
• Experiment C: Generation of static electricity by rubbing cells with paper.
The compositions of the mixtures of the Examples 1 to 10 is specified below, the individual compounds are coded as follows:
Figure imgf000008_0001
Figure imgf000009_0001
Example 1
A nematic composition A is formulated comprising:
Figure imgf000010_0001
Different amounts of 18-Crown-6 are added to this composition. The concentrations of which, the discharge time (τdc) and the specific resistivity (ρ) are given in the following table I
Figure imgf000010_0002
The correlation of the discharge time and the concentration of the crown ether of Experiment A is shown in FIG. 1; FIG. 2 gives the correlation between the specific resistivity and the discharge time.
The correlation of the discharge time and the concentration of the crown ether of Experiment B is shown in FIG. 4;
The correlation of the discharge time and the concentration of the crown ether of Experiment C is shown in FIG. 5.
Example 2
A nematic composition B is formulated comprising:
Figure imgf000011_0001
Different amounts of 18-Crown-6 are added to this composition. The concentrations of which, the discharge time (τdc) and the specific resistivity (ρ) are given in the following table II
Figure imgf000012_0001
The correlation of the discharge time and the concentration of the crown ether of Experiment A is shown in FIG. 3;
The correlation of the discharge time and the concentration of the crown ether of Experiment B is shown in FIG. 4;
The correlation of the discharge time and the concentration of the crown ether of Experiment C is shown in FIG. 5.
Example 3
A nematic composition C is formulated comprising:
Figure imgf000013_0001
Different amounts of 18-Crown-6 are added to this composition. The concentrations of which, the discharge time (τdc) and the specific resistivity (p) are given in the following table III.
Figure imgf000013_0002
BRIEF DESCRIPTION OF THE FIGURES
FIG.1: Discharge time (τdc) as a function of the concentration of 18- Crown-6 in composition A with experiment A (Electrostatic discharge simulator, applied voltage 10 kV).
FIG.2: Discharge time (τdc) as a function of the specific resistivity in composition A with experiment A (Electrostatic discharge simulator, applied voltage 10 kV).
FIG.3: Discharge time (τdc) as a function of the specific resistivity in composition A ( -♦- ) and B (
Figure imgf000014_0001
) with experiment A (Electrostatic discharge simulator, applied voltage 10 kV).
FIG.4: Discharge time (τdc) as a function of the specific resistivity in composition A ( -♦- ) and B (
Figure imgf000014_0002
) with experiment B (DC 30V, applied 10 s).
FIG.5: Discharge time (τdc) as a function of the specific resistivity in composstion A ( -♦- ) and B (
Figure imgf000014_0003
) with experiment C (Rubbing with paper).

Claims

Claims
1. Nematic liquid crystal composition which exhibits a resistivity of at least 1 × 1011 Ωcm, characterized in that it contains
• 1 to 10,000 ppm of a crown ether.
2. Nematic liquid crystal composition according to claim 1 , characterized in that the crown ether is a cyclic compound of formula A or B
[(CH2)2mO]m A,
[(CH2)2m-4O]m-2 · (C6H4O)2 B, in which m is an integer between 4 and 8.
3. Nematic liquid crystal composition according to claim 2, characterized in that the crown ether is a compound of formula Aa or Ba
Figure imgf000015_0002
4. Nematic liquid crystal composition according to any of the preceding claims, characterized in that the birefringence is 0.110 or less.
5. Nematic liquid crystal composition according to any of the preceding claims, characterized in that it contains at least one liquid crystalline compound of formula I and at least one compound of formula II.
Figure imgf000015_0001
Figure imgf000016_0001
in which
R1, R2 and R3 are each independently alkyl, alkoxy or alkenyl with up to 12 C atoms,
X is -CN, F, Cl, -OCF3 or -OCF2H
the rings A, B, C and D each independently denote
1,4 cyclohexylene, 1,4-cyclohexenylene, 1,4- phenylene each of which being optionally substituted by one or two fluorine atoms,
Z1 and Z2 are each independently -C≡C-, -CH2CH2-, -COO- or a single bond,
L1 and L2 each independently denote H or F,
n is 0 or 1 , and
o is 0, 1 or 2.
6. Nematic liquid crystal composition according to claim 5, characterized in that it contains at least one compound selected from formulae la to le and at least one compound selected from formulae lla,
Figure imgf000016_0002
Figure imgf000017_0001
in which R1, R2, R3, L1, L2, Z1 and the rings B and C have the meaning given in claim 5,
q is 0 or 1 , and
L3 is H or F.
7. Method of improving the electrostatic behavior of a liquid crystal display device, characterized in that a composition according to any of the preceding claims is used as a dielectric in said display device.
8. Method of improving the discharge time of an electrostatically charged liquid crystal display device, characterized in that a composition according to any of claims 1 to 6 is used as a dielectric in said display device.
PCT/EP1996/002860 1995-07-13 1996-07-01 Liquid crystal composition WO1997003146A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE19681567T DE19681567B4 (en) 1995-07-13 1996-07-01 liquid crystal composition
JP52976596A JP4195083B2 (en) 1995-07-13 1996-07-01 Liquid crystal composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP95110950 1995-07-13
EP95110950.3 1995-07-13

Publications (1)

Publication Number Publication Date
WO1997003146A1 true WO1997003146A1 (en) 1997-01-30

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CN (1) CN1137241C (en)
DE (1) DE19681567B4 (en)
TW (1) TW434310B (en)
WO (1) WO1997003146A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
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WO2010145211A1 (en) * 2009-06-16 2010-12-23 Industrial Technology Research Institute Liquid fluorescent composition and light emitting device

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KR101077606B1 (en) * 2003-08-01 2011-10-27 삼성전자주식회사 Liquid crystalline compound having fast response time and high isotropic temperature liquid crystalline composition comprising the same and liquid crystalline display comprising the same
JP5495003B2 (en) * 2008-04-11 2014-05-21 Ｄｉｃ株式会社 Ferroelectric liquid crystal composition and display device using the same
CN104774622B (en) * 2014-01-15 2018-01-26 江苏和成显示科技股份有限公司 Negative liquid crystal composition and the display device comprising the liquid-crystal composition
CN107815323B (en) * 2017-11-16 2018-09-14 黑龙江天有为电子有限责任公司 A kind of liquid-crystal composition and its application in the vehicle-mounted segment encode liquid crystal display of antistatic
JP2023070535A (en) * 2021-11-09 2023-05-19 スタンレー電気株式会社 Liquid crystal display device

Citations (5)

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US3814700A (en) * 1972-08-03 1974-06-04 Ibm Method for controllably varying the electrical properties of nematic liquids and dopants therefor
JPS54106084A (en) * 1978-02-08 1979-08-20 Mitsubishi Electric Corp Liquid crystal composition
EP0385688A2 (en) * 1989-02-27 1990-09-05 Matsushita Electric Industrial Co., Ltd. Ferroelectric liquid crystal composition and ferroelectric liquid crystal display device
EP0429662A1 (en) * 1989-05-27 1991-06-05 Mitsubishi Kasei Corporation Liquid crystal composition and liquid crystal element
WO1991008272A1 (en) * 1989-12-01 1991-06-13 Hoechst Aktiengesellschaft Use of complex ligands for ions in ferroelectric liquid crystal mixtures

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3814700A (en) * 1972-08-03 1974-06-04 Ibm Method for controllably varying the electrical properties of nematic liquids and dopants therefor
JPS54106084A (en) * 1978-02-08 1979-08-20 Mitsubishi Electric Corp Liquid crystal composition
EP0385688A2 (en) * 1989-02-27 1990-09-05 Matsushita Electric Industrial Co., Ltd. Ferroelectric liquid crystal composition and ferroelectric liquid crystal display device
EP0429662A1 (en) * 1989-05-27 1991-06-05 Mitsubishi Kasei Corporation Liquid crystal composition and liquid crystal element
WO1991008272A1 (en) * 1989-12-01 1991-06-13 Hoechst Aktiengesellschaft Use of complex ligands for ions in ferroelectric liquid crystal mixtures

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* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 3, no. 128 (C - 062) *

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Publication number Priority date Publication date Assignee Title
WO2010145211A1 (en) * 2009-06-16 2010-12-23 Industrial Technology Research Institute Liquid fluorescent composition and light emitting device

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Publication number Publication date
KR19990028911A (en) 1999-04-15
JP4195083B2 (en) 2008-12-10
TW434310B (en) 2001-05-16
DE19681567B4 (en) 2007-02-01
DE19681567T1 (en) 1998-10-15
CN1190982A (en) 1998-08-19
KR100433333B1 (en) 2004-07-16
CN1137241C (en) 2004-02-04
JPH11508286A (en) 1999-07-21

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