WO2005095311A9 - ベンゼン誘導体、液晶組成物および液晶表示素子 - Google Patents
ベンゼン誘導体、液晶組成物および液晶表示素子Info
- Publication number
- WO2005095311A9 WO2005095311A9 PCT/JP2005/005837 JP2005005837W WO2005095311A9 WO 2005095311 A9 WO2005095311 A9 WO 2005095311A9 JP 2005005837 W JP2005005837 W JP 2005005837W WO 2005095311 A9 WO2005095311 A9 WO 2005095311A9
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- compound
- carbons
- alkyl
- independently
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
-
- 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
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
-
- 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
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
- C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
-
- 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
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
Definitions
- the present invention relates to a liquid crystal compound, a liquid crystal composition, and a liquid crystal display element. More specifically, the present invention relates to a benzene derivative, a liquid crystal composition containing the benzene derivative and having a nematic phase, and a liquid crystal display device containing the composition.
- Liquid crystal display elements are based on the liquid crystal operation mode, PC (phase change), TN (twisted nematic), S ⁇ (super twisted nematic), BTN (Bistable twisted nematic, E B) , OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment), etc.
- This element is classified into PM (passive matrix) and AM (active matrix) based on the driving method.
- PM (passive matrix) is classified into static and mano-replex (multiplex)
- AM is classified into TFT (thin film transistor), MIM (metal insulator metal), etc.
- liquid crystal display elements contain a liquid crystal composition.
- a liquid crystal display element is sometimes simply referred to as an element.
- a liquid crystal composition may be simply referred to as a composition.
- a liquid crystal compound may be simply referred to as a compound.
- the composition preferably has appropriate physical properties. The general physical properties necessary for the compound that is a component of the composition are as follows.
- the clearing point is the transition temperature of the liquid crystal phase isotropic phase.
- the liquid crystal phase is nematic and smectic. It means ku phase.
- a compound having a large dielectric anisotropy often has a high viscosity.
- a composition is prepared by mixing many compounds. Therefore, these compounds are preferably miscible with other compounds. Since the device may be used at temperatures below freezing, compounds with good compatibility at low temperatures are preferred.
- a compound having a high! /, A clearing point or a low liquid crystal phase! / And a minimum temperature contributes to a wide temperature range of the nematic phase in the composition.
- Preferred compositions have low viscosity and optical anisotropy suitable for the device mode.
- the large dielectric anisotropy of the compound contributes to the low threshold voltage of the composition. With such a composition, an element having characteristics such as a wide usable temperature range, a short response time, a large contrast ratio, a small driving voltage, a small power consumption, and a large voltage holding ratio can be obtained. .
- a compound ⁇ having 2, 3 difluoro 1, 4 phenylene in a partial structure is generally known (see Non-Patent Document 2).
- Dielectric constant As a compound for improving the anisotropy, a compound ( ⁇ ), difluoromethyl, in which trifluoromethyl is bonded to the side orientation of the compound molecule in order to make the negative dielectric anisotropy even larger.
- the compounds (iii) and (iv) to which is bound are reported! /, (See Patent Document 1, Non-patent Document 1, Non-patent Document 2 and Patent Document 2).
- Patent Document 1 Japanese Patent Laid-Open No. 8-040953
- Patent Document 2 WO2000 / 03963 non-fret
- Non-patent literature l Synlett. 1999, No.4, 389-396
- Non-Patent Document 2 Angew. Chem. Int. Ed. 2000, 39, 4216-4235
- the first object of the present invention is to exhibit negative dielectric anisotropy and to have a relatively high clearing point, relatively small viscosity, appropriate optical anisotropy, and other liquid crystalline compounds.
- the object is to provide a liquid crystal compound having an excellent balance of physical properties such as excellent compatibility.
- a second object is to provide a liquid crystal composition containing this compound and having a wide temperature range of a nematic phase, a small viscosity, suitable optical anisotropy, and a low threshold voltage.
- the third object is to provide a liquid crystal display device containing this composition and having a short response time, a small power consumption, a large contrast, and a high voltage holding ratio.
- a liquid crystal compound is a generic term for a compound having a liquid crystal phase such as a nematic phase or a smectic phase, and a compound having no liquid crystal phase but useful as a component of a liquid crystal composition.
- a liquid crystal display element is a general term for a liquid crystal display panel and a liquid crystal display module.
- the upper limit temperature of the nematic phase is the phase transition temperature of the nematic phase isotropic phase, and may simply be abbreviated as the upper limit temperature.
- the lower limit temperature of the nematic phase is sometimes simply abbreviated as the lower limit temperature.
- the ability to describe a compound represented by formula (1) as compound (1) is S.
- a plurality of consecutive CH— is not replaced by O. It may be a branched group. This means that any CH— in these groups is O or
- the same applies when CH CH is replaced.
- the amount of the compound expressed as a percentage shown in the composition is a weight percentage (% by weight) based on the total weight of the composition.
- the present invention includes the following items.
- Ra and Rb are independently hydrogen or alkyl of 120 carbons; in this alkyl, any one CH— is replaced by one O S CO or one SiH—.
- Any hydrogen may be replaced by halogen
- a u A 12 A 2 A 21 and A 22 are each independently 1,4-cyclohexylene, 1,4 phenylene, decahydronaphthalene 1,6-6-diyl, 1,2,3,4-tetrahydronaphthalene 2, 6-gyl, or naphthalene 1, 2, 6-gyl; in these rings, one or two non-adjacent ones CH— are replaced by one OS CO or one SiH—.
- CH) —CH CH, one (CH) CF O—, or OCF (CH) one;
- z u z 12 z 2 z 21 and z 22 are independently a single bond,-(CH) COO -oco
- j k m n p and q are independently 0 or 1, and their sum is 1 2 or 3;
- Ra in formula (1) is not hydrogen, alkoxy or alkoxymethyl, and Ra in formula (2) is 1-alkenyl.
- Ra and Rb are independently hydrogen or alkyl of 1 to 20 carbon atoms; in this alkyl, any —CH— that is not located at the terminal is O—, —S or —CO—
- a U , A 12 , A 2 , A 21 and A 22 are each independently 1,4-cyclohexylene, 1,4 phenylene, decahydronaphthalene 1,6 diyl, 1, 2, 3, 4 tetrahydro Naphthalene-1,6 or naphthalene-1,6 diyl; in these rings, one or two non-adjacent —CH— is replaced by —O—, —S, or —CO.
- any hydrogen may be replaced by a halogen
- CH) —CH CH, one (CH) CF O—, or OCF (CH) one;
- Z u Z 12 Z 2 Z 21 and Z 22 are each independently a single bond,-(CH) —coo— -oco
- Ra is not hydrogen, alkoxy or alkoxymethyl! /, But no shift; formula (2-2), formula (2-5) and formula In (2-9)! /, Ra is 1 alkenyl.
- Ra and Rb are independently alkyl having 1 to 10 carbons, alkoxy having 1 to 10 carbons, 2 to carbons; alkoxyalkyl having 10 carbons, alkenyl having 2 to 10 carbons, and 3 to 10 carbons; Alkenyloxy, perfluoroalkyl having 1 to 10 carbons, or perfluoroalkoxy having 10 to 10 carbons;
- a u A 12 A 2 A 21 and A 22 are independently 1,4-cyclohexylene, 1,3-dioxane 1,2,5 gil, 4,6 dioxane 1,2,5 gil, 1,4 Diene, 2 Phenoreoro 1, 4 Phenolene, 3 Funenole 1, 4 Phenolene, 2, 3 Diphnoleolo 1, 4 —Phenylene, Decahydronaphthalene 1, 2 6 Dinore, 1, 2, 3, 4 tetrahydronaphthalene-2,6 dinore or naphthalene 2,6 dil;
- Z 11 and Z 12 are independently a single bond, — (CH 2) — — COO— — OCO— —CF 2 O
- CH CH (CH) CF O—, or OCF (CH);
- Z 2 Z 21 and Z 22 are independently a single bond, (CH) COO oco c
- ) -CH CH- (CH) CF O-, or OCF (CH)--;
- Ra and Rb forces are independently alkyl having 1 to 10 carbons, alkoxy having 1 to 10 carbons, 2 to carbons; alkoxyalkyl having 10 carbons or 2 to 10 carbons;
- a U A 12 A 2 A 21 and A 22 forces Independently 1, 4-cyclohexylene, 1, 4 phenylene, 2 funneloreol, 1, 4 phenolylene, 3 funneloreol, 1, 4 phenolylene, or 2, 3-difunoleolone 1 , 4 phenylene;
- Z 2 Z 21 and Z 22 are independently a single bond, (CH) -OCH C
- Ra is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons
- Rb is alkoxy having 1 to C: L0;
- a U , A 12 , A 2 , A 21 and A 22 forces Independently 1,4-cyclohexylene, 1,4 phenylene, 2-funoleolone, 1,4 phenylene, or 3-funoleolone, 1,4 Is bilen;
- Z 2 , Z 21 and Z 22 are independently a single bond, CH 2 O—, — OCH —, — CF 0 —, or
- Y is a single bond, (CH 3) 2 CH 2 CH—, -CF 0 1, -OCF, 1 (CH 2) 1,-
- a 1 or A 2 is 1,4-cyclohexylene, Y or Z 2 is a single bond in Formula (1-1) to Formula (1-9), and Formula (2 — The compound according to any one of [3] to [6], wherein Z 2 is a single bond in formulas (2-9).
- a 1 or A 2 is 1, 4 phenylene, Y or Z 2 in formulas (1-1) to (1-9) is a single bond, and 2-1) to formula (2-9), Z 2 is a single bond,
- [0021] is represented by formula (2-1); A 1 is 1,4 cyclohexylene; and W is one (CH ) I,-CH 2 O—, or CF 2 O 3, The chemical compound according to any one of [3] and [6]
- a 1 and A 11 are both 1,4-cyclohexylene; Z 11 is a single bond; and W is one (CH)-CH O, or one CF O—, [3]
- [0024] [16] represented by any one of formula (12), formula (14), formula (15), formula (17), formula (18), and formula (19); And Z 2- CH O— — OCH — CF O—, or
- Ra is an alkyl having 1 to 10 carbons; or an alkyl having 2 to 10 carbon atoms; an alkenyl having 10 carbons; and Rb is an alkoxy having 1 to 10 carbon atoms.
- Ra is an alkyl having 1 to 10 carbons; or an alkyl having 2 to 10 carbons; an alkenyl having 10 carbons; and Rb is an alkoxy having 1 to 10 carbon atoms.
- a 1 and A 11 are both 1,4-cyclohexylene; Y is —CH 2 CH 1; and Z 11 is a single bond;
- [0027] is represented by formula (1-3); Ra is an alkyl having 1 to 10 carbons; or an alkyl having 2 to 10 carbons; an alkenyl having 10 carbons; and Rb is an alkoxy having 1 to 10 carbon atoms.
- Ra is an alkyl having 1 to 10 carbons; or an alkyl having 2 to 10 carbon atoms; an alkenyl having 10 carbons; and Rb is an alkoxy having 1 to 10 carbon atoms.
- Ra is an alkyl having 1 to 10 carbons; or an alkyl having 2 to 10 carbon atoms;
- a 1 is 1,4-cyclohexylene; and
- Y is a single bond.
- Ra is an alkyl having 1 to 10 carbons; or an alkyl having 2 to 10 carbon atoms; an alkenyl having 10 carbons; and Rb is an alkoxy having 1 to 10 carbon atoms.
- a 1 is 1,4-cyclohexylene; and Y is —CH 2 CH 1.
- [0031] is represented by the formula (2-1); Ra is an alkyl having 1 to 10 carbons; or an alkyl having 2 to 10 carbon atoms; an alkenyl having 10 carbons; and Rb is an alkoxy having 1 to 10 carbon atoms.
- a 1 is 1,4-cyclohexylene; and W is — (CH 2) 1.
- [24] is represented by the formula (2-1); Ra is an alkyl having 1 to 10 carbons; or an alkyl having 2 to 10 carbon atoms; an alkenyl having 10 carbons; and Rb is an alkoxy having 1 to 10 carbon atoms.
- a 1 is 1,4-cyclohexylene; and W is —CH 2 O—.
- Ra is an alkyl having 1 to 10 carbons; or an alkyl having 2 to 10 carbon atoms; an alkenyl having 10 carbons; and Rb is an alkoxy having 1 to 10 carbon atoms.
- Ra is an alkyl having 1 to 10 carbons; or an alkyl having 2 to 10 carbons; an alkenyl having 10 carbons; and Rb is an alkoxy having 1 to 10 carbons.
- a 1 and A 11 are both 1,4-cyclohexylene; Z 11 is a single bond; and W is —CH 2 O—.
- [28] is represented by formula (2-3); Ra is 1 to C carbon; 10 alkyl or 2 to C; alkenyl, and Rb is alkoxy having 1 to 10 carbons; Yes; A 1 is 1,4-phenol, and A 11 is 1,4-cyclohexylene; Z 11 is a single bond; and W is one (CH 2) one. [3] The compound according to item.
- [0037] is represented by formula (2-3); Ra is 1 to C carbon; 10 alkyl or 2 to C; alkenyl having 10 carbons; and Rb is alkoxy having 1 to 10 carbons. Yes; A 11 is 1, 4 —Phenylene; Z 11 is a single bond; and W is one (CH 3) —, as described in paragraph [3].
- [0038] is represented by formula (2-6); 11 ⁇ 2 is alkenyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and Rb is alkoxy having 1 to 10 carbons; A 11 and A 12 are both 1,4-cyclohexylene; Z 11 and Z 12 are single bonds; and W is — (CH 2) 1 or 1 CH 2 O 3. Compound.
- Ra is an alkyl having 1 to 10 carbon atoms
- Rb is an alkyl having 1 to 10 carbon atoms or an alkenyl having 2 to 10 carbon atoms
- a 2 is 1,4-cyclohexylene
- Z 2 is —OCH—.
- Ra is an alkyl having 1 to 10 carbon atoms
- Rb is an alkyl having 1 to 10 carbon atoms or an alkenyl having 2 to 10 carbon atoms
- a 2 and A 21 are both 1,4-cyclohexylene
- Z 2 is —OCH—
- Z 21 is a single bond.
- Ra and Rb are each independently 1 to C carbon; alkyl of 10 or alkenyl of 2 to 10 carbon; A 1 and A 2 are both 1
- Ra and Rb are each independently 1 to 10 carbon atoms; alkyl having 10 carbons or 2 to 10 carbon atoms; A 1 being 1, 4—
- the compound according to item [3], which is cyclohexylene and A 2 is 1,4 phenylene; and Y and Z 2 are both single bonds.
- Ra and Rb are each independently 1 to 10 carbon atoms; 10 alkyls or 2 to 10 carbons; A 1 is 1, 4
- R 1 is alkyl having 1 10 carbons; in this alkyl, any —CH
- X 1 is fluorine, chlorine -OCF -OCHF -CF -CHF CH F OCF CHF, or OC
- F CHFCF; B 1 and D are independently 1,4-cyclohexylene, 1,4-fuel
- R 2 and R 3 are independently alkyl having 1 to 10 carbons; in this alkyl, any —CH— may be replaced by —O—. Is —CH
- X 2 is 1 CN or 1 C ⁇ C—CN
- G is 1, 4-cyclohexylene, 1, 4-phenylene, 1,3-dioxane-1,5-5-diyl or pyrimidine-1,2,5-diyl
- J is 1,4-cyclohexylene, 1,4-phenylene, pyrimidine-1, 5-zyl, or 1,4-phenylene, where at least one hydrogen is replaced by fluorine
- Z 6 is — (CH 2) —,
- L 3 , L 4 and L 5 are independently
- [39] It comprises at least one of the compounds described in [1] and a compound represented by each of the formula (8), the formula (9), the formula (10), the formula (11), and the formula (12).
- R 4 is alkyl having 1 to 10 carbon atoms
- R 5 is fluorine or alkyl having 1 10 carbon atoms; in these alkyls, any —CH— is replaced by —O
- M and P 1 are independently 1,4-cyclohexylene, 1,4 phenylene or decahydro-2,6 naphthylene;
- Z 7 and Z 8 are independent -(CH) -COO or a single bond;
- L 6 and L 7 are independently hydrogen or
- L 6 and L 7 are fluorine.
- a liquid crystal composition that may contain at least one optically active compound:
- R 6 and R 7 are independently alkyl having 1 to 10 carbon atoms; Any —CH— can be replaced by —O— (CH 2) —is —CH
- IT and R 3 are independently alkyl having 1 10 carbons; in this alkyl, any —CH— may be replaced by 0— (CH 3) —is —CH
- X 2 is one CN or one C ⁇ C—CN
- G is 1,4-cyclohexylene, 1, 4 —Phenylene, 1,3 dioxane 1,2,5 gil or pyrimidine 1,2,5 gil
- J is 1,4 cyclohexylene, 1,4 phenylene, 1,2,5 gil, or at least Is 1, 4 -phenylene with one hydrogen replaced by fluorine
- Z 6 is — (CH 2)
- L 3 L 4 and L 5 are independently
- Hydrogen or fluorine and b c and d are independently 0 or 1.
- R 6 and R 7 are independently alkyl having 1 10 carbons; in this alkyl, any —CH— may be replaced by —O— CH
- CH CH may be replaced by any hydrogen and any hydrogen may be replaced by fluorine;
- Chobi 11 is independently 1, 4-cyclohexylene, 1, 4 phenylene, pyrimidine-2 5-zyl, or 1,4 phenylene with at least one hydrogen replaced by fluorine; and
- Z 9 and Z 1 are independently C ⁇ C—COO, one (CH 2) —C
- R 6 and R 7 are independently alkyl having 1 10 carbon atoms; in this alkyl, any —CH— may be replaced by — ⁇ — CH
- CH CH may be replaced by any hydrogen and any hydrogen may be replaced by fluorine;
- Chobi 11 is independently 1, 4-cyclohexylene, 1, 4 phenylene, pyrimidine-2 5-zyl, or 1,4 phenylene with at least one hydrogen replaced by fluorine; and
- Z 9 and Z 1 are independently C ⁇ C—COO, one (CH 2) —C
- R 6 ⁇ Q— Z 9 — T 1 U— R 7 (15) where R 6 and R 7 are independently alkyls of 1 10 carbons; in this alkyl, any —CH— Is an arbitrary one that can be replaced by —O (CH 2) — is —CH
- the compound of the present invention has general physical properties necessary for liquid crystal compounds, stability to heat, light, etc., appropriate optical anisotropy, appropriate dielectric anisotropy, and superiority to other liquid crystal compounds. Compatible with each other.
- the liquid crystal composition of the present invention contains at least one of these compounds, and has a high maximum temperature of the nematic phase, a low minimum temperature of the nematic phase, a small viscosity, a suitable optical anisotropy, and a low threshold voltage.
- Have The liquid crystal display device of the present invention contains this composition and has a wide temperature range in which it can be used, a short response time, a large contrast ratio, and a low driving voltage.
- the compound of the present invention is represented by either formula (1) or formula (2).
- Ra and Rb in formula (1) and formula (2) are independently hydrogen or alkyl having! In this alkyl, any one CH— is one O S— —CO.
- Ra or Rb are hydrogen, anolenoquinole, alkoxy, alkoxyalkyl, alkoxyalkoxy, alkylthio, alkylthioalkoxy, isyl, isylalkyl, acyloxy, acyloxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, anolenoquinole, alkenyl.
- Rogen are fluorine and chlorine.
- a more preferred halogen is fluorine.
- straight chains are preferred over branches. Even when Ra and Rb are branched groups, they are preferred when they are optically active.
- Ra and Rb include alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, 2 to 2 carbon atoms; alkoxyalkyl having 10 carbon atoms, alkenyl having 2 to 0 carbon atoms, and 2 to 0 carbon atoms. Alkenyloxy, perfluoroalkyl having 1 to 10 carbon atoms, and perfluoroalkoxy having 1 to 10 carbon atoms. More preferred examples are alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkoxy having 2 to 10 carbon atoms, alkoxyalkyl having 2 to 10 carbon atoms and alkenyl having 2 to 10 carbon atoms. Further preferred Ra is C 1 -C 10 alkyl or C 2 10 alkenyl, and particularly preferred R b is C 1 10 alkoxy.
- CH CH in alkenyl depends on the position of the double bond.
- alkyl is —CH 2 C 3 H 2 C 3 C 4 C 4 C 4 C
- alkoxy is OCH 2 -OC
- xyalkyl are —CH 2 OCH 2 CH 2 OC 2 CH 2 O 2 CH, 1 (
- alkenyl is —CH ⁇ CH—CH ⁇ CHCH—CH—CH ⁇ CH
- HCH and OCH CH CHC H.
- a specific example of an alkyl in which at least one hydrogen is replaced by a halogen is one (C H) -CF CH F -CF CHF CH CF CF CF (CH) F C
- alkoxy substituted with a rogen is — ⁇ (CH) F —OCF CH F
- At least one hydrogen is halogen
- Ra or Rb is CH C H C H C H C
- Ra or Rb are CH C H C H C H
- CH CHC H
- Ra CH C H C H C H C H
- Rb More preferred specific examples of Rb are —OCH 2 —OC 2 H and —O
- Equation (1) and Equation (2) A U A 12 A 2 A 21 and A 22 are independently 1,4-cyclocyclohexylene, 1,4-phenolene, decahydronaphthalene-1,6-diyl, 1,2,3,4- Tetrahydronaphthalene 2,6 dinore or naphthalene 2,6 dinore. In these rings, one or two non-adjacent CH— are OS CO
- One or two non-adjacent one CH— is 101, 1 S, 1 C01 or 1 SiH
- Examples of the cyclic group replaced with 2 2 are groups represented by the following formulas (16-1) to (16-30). Preferred examples among these are the formula (16-1), the formula (16-2), the formula (16-3), the formula (164), the formula (16-13), and the formula (16-21). .
- Examples of the cyclic group in which arbitrary hydrogen is replaced by halogen are cyclic groups represented by the following formulas (17-1) to (17-17). Preferred examples among these include formula (17-1), formula (172), formula (17-3), formula (17-5), formula (17-7), formula (17-8), formula (17-10), formula (17-14), formula (17-16) and formula (17-17).
- a u A 12 A 2 A 21 or A 22 are 1,4-cyclohexylene, 1,3 dioxane 2,5 dinore, 4,6 dioxane 2,5 dinole, 1,4 phenol Len 2 Funoleo 1, 1, 4 Fenylene, 3 Funoleo 1, 4, 4 Fenylene, 2, 3 Difunoleo low 1, 4 Fenylene, Decahydronaphthalene 2, 6 Dinore, 1, 2, 3, 4 Tetrahydr Lonaphthalene 1,2,6 dinore and Naphthalene 1,2,6 dill.
- More preferred ⁇ columns are 1,4-cyclohexylene, 1,4 phenylene, 2 fluorolone, 1,4 phenylene, 3 phenoleol, 1,4 phenylene, or 2,3 diphenoleol, 1,4 phenylene. is there . Further preferred examples are 1,4 cyclohexylene, 1,4 phenylene, 2 fluoro-1,4 phenylene, and 3-funoleolone 1,4 phenylene. Particularly preferred examples of ⁇ 1 or ⁇ 2 are 1,4-cyclohexylene and 1,4 phenylene.
- YWZ u Z 12 Z 2 Z 21 and Z 22 in the [0072] formula (1) and (2) is a linking group.
- Y is a single bond, (CH) ⁇ — COO— — OCO— —CF O— —OCF— — CH
- a preferred example of Y is a single bond, — (CH 2) —COO——OCO——CF 2 O——O
- the configuration of such a linking group with respect to the double bond is preferably trans rather than cis.
- W are one (CH 3) — and one CH 2 O 3.
- CH C
- Trans is preferable to cis for the configuration of the double bond.
- Preferred examples of Z 2 , Z u , Z 12 , Z 21 or Z 22 are a single bond, one (CH) one, -COO-,-
- -OCF one, one CH2 CH, one (CH) CF 0 1 and 10 CF (CH 2) —.
- Z 2 , Z u , Z 12 , Z 21 or Z 22 are single bonds, —CH 2 O—, —O
- Trans is preferred over cis.
- j, k, m, n, p and q are each independently 0 or 1, and their sum is 1, 2 or 3. That is, the compound (1) and the compound (2) are compounds having 2 to 4 rings.
- Ra in formula (1) is not hydrogen, alkoxy or alkoxymethyl
- Ra in formula (2) is 1 alkenyl.
- the sum of j, k and m is preferably 1 or 2.
- the sum of np and q is preferably 1 or 2.
- a 1 or A 2 are 1,4-phenylene and 1,4-cyclohexylene.
- a particularly preferred example of formula (1) and formula (2) is that when A 1 and A 2 are both 1,4-phenylene, A 1 is 1,4-phenylene, and A When 2 is 1,4-cyclohexylene, A 1 is 1,4-cyclohexylene, and A 2 is 1,4 phenylene, and A 1 and A 2 are both 1,4-cyclohexane. This is the case for hexylene.
- Y are single bonds, CH 2) CF 3 O and C
- H CH.
- Z 2 is a single bond, CH 2 O— —OCH CF
- Z 2 is preferably —CH 2 O— —OCH 2 CF 3 O or OCF—.
- Ra is alkyl or alkenyl
- Rb is alkoxy
- a 1 and A 11 are independently 1,4-phenylene or 1,4-cyclohexylene and both Y and Z 11 are preferably a single bond.
- Ra is alkyl or alkenyl
- Rb is alkoxy
- a 1 is 1,4-cyclohexylene.
- Y is preferably a single bond or one (CH 3) 2 —. At this time, Y is one (C
- H is one.
- Ra is alkyl or alkenyl
- Rb is alkoxy
- a 1 and A 11 are both 1 , 4 cyclohexylene
- ⁇ is-(CH)
- Z 11 is preferably a single bond.
- Ra and Rb are independently alkyl or alkenyl, and A 1 and A 2 are both 1, 4-phenylene, and is preferably Y, and Z 2 are both single bonds.
- Ra and Rb are independently alkyl or alkenyl, and A 1 is 1 , 4-cyclohexylene, A 2 is 1,4 phenylene, and Y and Z 2 are both single bonds.
- Ra and Rb are independently alkyl or alkenyl, and A 1 is 1 , 4 phenylene, A 2 is 1,4-cyclohexylene, and both Y and Z 2 are preferably single bonds.
- Z 2 is preferably a single bond.
- a 1 is preferably 1,4-cyclohexylene.
- Ra is alkyl or alkenyl
- Rb is alkoxy
- a 1 is 1 , 4-cyclohexylene
- W is preferably one (CH 3) one.
- a bond is preferred.
- a 11 and A 12 are both 1,4-cyclohexylene, Y is one (CH) — And both z 11 and are preferably a single bond.
- compound (1) and compound (2) may contain isotopes such as 2 H (deuterium) and 13 C in an amount greater than the natural abundance. At this time, there is no significant difference in the physical properties of the compounds.
- Preferred examples of the formula (1) are the following formulas (11) to (19), and preferred examples of the formula (2) are formulas (2-1) to (2-9). .
- formula (1 1) to formula (1-9) it is particularly preferred that at least one of Y and Z 2 is a single bond.
- Z 2 it is particularly preferable that Z 2 is a single bond.
- Ra is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons
- Rb is alkoxy having 1 to 10 carbons
- a 1 is 1, 4—
- Preferred is cyclohexylene and Y is a single bond or one (CH) —! / '
- Ra is alkyl having 1 to 10 carbon atoms
- Rb is alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms
- a 2 is 1,4-cyclohexylene.
- Z 2 is preferably —OCH—.
- Ra is alkyl having 1 10 carbons or alkenyl having 2 10 carbons
- Rb is alkoxy having 1 10 carbons
- a 1 and A 11 Are both 1,4-sucrose xylene, and both Y and Z 11 are preferably single bonds.
- Ra is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons
- Rb is alkoxy having 1 to 10 carbons
- both A 1 and A 11 are 1, 4
- xylene is xylene
- Y is one (CH)
- Z 11 is a single bond.
- Ra is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons
- Rb is alkoxy having 1 to 10 carbons
- a 1 is 1,4-phenylene.
- the a xylene a 1 1 is to 1, 4 Shikuro and arbitrariness preferred that Y and Z 11 are both single bonds.
- Ra is alkyl having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms
- Rb is alkoxy having 1 to 10 carbon atoms
- both A 1 and A 11 are 1, 4
- it is phenylene
- Y and Z 11 are both single bonds.
- Ra and Rb are each independently an alkyl having 1 to 10; alkyl having 10 carbons or an alcohol having 2-10 carbon atoms, and A 1 and A 2 being both 1, 4 Yes, and Y and Z 2 are preferably both single bonds! /
- Ra and Rb are independently 1 to carbon atoms; alkenyl of alkyl carbon atoms or 2 10 10, a xylene A 1 is to 1, 4 cycloalkyl, A 2 Is 1,4 phenylene and both Y and Z 2 are preferably single bonds.
- the number of carbon atoms Ra and Rb are independently 1; 10 alkyl or alkenyl having 2 to 10, an A, 4-phenylene, A 2 is 1, 4-cyclohex It is preferably silene, and both Y and z 2 are preferably a single bond.
- Ra is alkyl having 1 to 10 carbons
- Rb is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons
- a 2 and A 21 are both 1 , 4-cyclohexylene
- Z 2 is —OCH—
- Z 21 is preferably a single bond.
- Ra is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons
- Rb is alkoxy having 1 to 10 carbons
- W is-(CH) —Or— CH
- O and A 1 is 1,4-cyclohexylene.
- a 1 and A 11 are preferably 1,4-cyclohexylene and Z 11 is a single bond.
- Ra is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons
- Rb is alkoxy having 1 to 10 carbons
- W is-(CH) —Or— CH
- O 1 , A 1 and A 11 are both 1,4-cyclohexylene, and Z 11 is a single bond.
- the liquid crystal composition of the present invention is a composition containing at least one of the compound (1) and the compound (2) and may contain at least one optically active compound.
- the composition of the present invention may contain a liquid crystal compound other than the compound (1) and the compound (2).
- a preferred liquid crystal compound other than the compound (1) and the compound (2) is a compound selected from the group consisting of compounds represented by the following formulas (3) to (15).
- R 1 is alkyl having 1 to 10 carbon atoms.
- any one non-terminal CH— can be replaced by one O (CH
- X 1 is fluorine, chlorine, OCF -OCHF -CF CHF CH F
- B 1 and D are independently 1, 4—
- E is 1,4-cyclohexylene, 1,4 phenylene, or 1,4-phenylene with at least one hydrogen replaced by fluorine.
- Z 4 and Z 5 are independently — (CH 2) 1, (CH 2) 2 -COO
- L 2 is independently hydrogen or fluorine.
- R 2 and R 3 are independently alkyl having 1 to 10 carbon atoms.
- any —CH— can be replaced by —O (C
- X 2 is one CN or one C ⁇ C—CN.
- G is 1,4-cyclohexylene, 1,4 phenylene, 1,3 dioxane 2,5 diyl or pyrimidine 1,2,5-diyl.
- J is 1,4-cyclohexylene, 1,4-phenylene, pyrimidine-1,2,5-diene, or 1,4-phenylene in which at least one hydrogen is replaced by fluorine.
- Z 6 is one (CH 3) —COO——CF 2 O——OCF—, or a single bond.
- L 3 L 4
- L 5 is independently hydrogen or fluorine.
- bc and d are independently 0 or (or 1?
- R 4 is alkyl having 1 to 10 carbon atoms
- R 5 is fluorine or alkyl having 1 to 10 carbon atoms.
- H may be replaced and any hydrogen may be replaced by fluorine.
- M And P 1 is independently 1,4-cyclohexylene, 1,4 phenylene or decahydro-2,6-naphthylene.
- Z 7 and Z 8 are independently one (CH 2) COO or single connection
- L 6 and L 7 are independently hydrogen or fluorine, and at least one of L 6 and L 7 is fluorine.
- R 6 and R 7 are independently alkyl having 1 to 10 carbon atoms. In this alkyl, any non-terminal CH— may be replaced by O.
- the element may be replaced with fluorine.
- QT and U are independently 1,4-cyclohexylene, 1,4 phenylene, pyrimidine-25 dinole, or 1,4 phenylene with at least one hydrogen replaced with fluorine.
- the first example of the liquid crystal composition in the present invention is at least one compound selected from the group consisting of compound (1) and compound (2), compound (3), compound (4) and compound (5 And at least one compound selected from the group consisting of at least one optically active compound! /, A composition.
- the second example of the liquid crystal composition in the present invention is at least one compound selected from the group consisting of compound (1) and compound (2), compound (61), compound (62) and It is a composition containing at least one compound selected from the group consisting of compound (7) and may contain at least one optically active compound.
- a third example of the liquid crystal composition of the present invention includes at least one compound selected from the group consisting of compound (1) and compound (2), and each of formula (8) to formula (12). At least one compound selected from the group consisting of the compounds represented by at least one An optically active compound may be included! / A composition.
- the fourth example of the liquid crystal composition in the present invention is at least one compound selected from the group consisting of compound (1) and compound (2), compound (13), compound (14) and compound.
- the composition comprises at least one compound selected from the group consisting of (15) and may contain at least one optically active compound.
- the fifth example of the liquid crystal composition of the present invention comprises a compound (6-1), a compound (6-2), and a compound (7) in addition to the combination of the compounds shown in the first example.
- a composition further comprising at least one compound selected from the group. That is, at least one compound selected from the group consisting of compound (1) and compound (2), at least one compound selected from the group consisting of compound (3), compound (4) and compound (5), and
- the composition contains at least one compound selected from the group consisting of compound (6-1), compound (6-2) and compound (7), and may contain at least one optically active compound.
- the sixth example of the liquid crystal composition in the present invention is selected from the group consisting of the compound (13), the compound (14) and the compound (15) in addition to the combination of the compounds shown in the first example.
- a composition further comprising at least one compound. That is, at least one compound selected from the group consisting of compound (1) and compound (2), at least one compound selected from the group consisting of compound (3), compound (4) and compound (5) And at least one compound selected from the group consisting of compound (13), compound (14) and compound (15), and may contain at least one optically active compound.
- the seventh example of the liquid crystal composition of the present invention includes, in addition to the combination of the compounds shown in the second example, a compound (13), a compound (14), and a compound (15).
- a composition comprising at least one compound selected from the group consisting of one compound, compound (13), compound (14) and compound (15), and may contain at least one optically active compound. is there.
- the compound of the present invention is a bicyclic, tricyclic or tetracyclic compound having 2-difluoromethyl-3 fluoro1,4 phenylene or 2 trifluoromethyl-3 fluoro 1,4 phenylene.
- the compound of the present invention is extremely physically and chemically stable under the conditions under which the device is normally used, and has good compatibility with other liquid crystal compounds.
- the composition containing the compound of the present invention is stable under conditions in which the device is usually used. Even when the composition is stored at a low temperature, the compound does not precipitate as a crystal or a smectic phase.
- the compound of the present invention has general physical properties necessary for a liquid crystal material, appropriate optical anisotropy, and appropriate dielectric anisotropy.
- the compound of the present invention has negative dielectric anisotropy. If the substituent and the linking group are properly selected, the compound of the present invention exhibits a large negative dielectric anisotropy.
- a compound having a large negative dielectric anisotropy is a useful component for lowering the threshold voltage and / or value voltage of a composition for IPS or VA.
- Ra or Rb is a linear group
- the temperature range of the liquid crystal phase is wide and the viscosity is small.
- Ra or Rb is a branched chain group
- compatibility with other liquid crystal compounds is good.
- a compound in which Ra or Rb is an optically active group is useful as a chiral dopant. By adding this compound to the composition, it is possible to prevent the reverse twisted domain generated in the device.
- a compound in which Ra or Rb is not an optically active group is useful as a component of the composition.
- Ra or Rb is alkenyl! /
- the configuration depends on the position of the double bond.
- Preferable! / Alkenyl compounds having a configuration have a high maximum temperature or a wide temperature range of the liquid crystal phase.
- At least two of A U , A 12 , A 2 , A 21 and A 22 are 1, 4 cyclohexylene.
- the upper limit temperature is high, the optical anisotropy is small, and the viscosity is small.
- the optical anisotropy is relatively large and the orientational order parameter is large.
- the temperature range of the liquid crystal phase with a large optical anisotropy is wide and the upper limit temperature is high.
- YZ u Z 12 Z 2 At least one of Z 21 and Z 22 is a single bond,-(CH) CF O
- This linking group is one (CH) ⁇ ⁇
- the dielectric anisotropy is negative and larger.
- a compound in which at least one of A 1 and A 2 is 1,4 optionally substituted with fluorine, and the linking groups Z 1 and Z 2 directly connected to the parenthesis ring are single bonds is Furthermore, the dielectric anisotropy is negative and larger, and at the same time the optical anisotropy is large.
- the compound (11) to compound (15) and the compound (2-1) to compound (2-5) which are bicyclic or tricyclic have a low viscosity! /.
- the compound (13) to compound (19) and the compound (13) to compound (19) which are tricyclic or tetracyclic have a high maximum temperature.
- a compound having the desired physical properties can be obtained by appropriately selecting the types of terminal groups, rings and bonding groups, and the number of rings. Therefore, the compounds of the present invention, in particular, the compounds (11) to (19) and the compounds (2-1) to (2-9) are useful as components of compositions used in devices such as IPS VA. is there.
- liquid crystal material such as a dielectric anisotropy, a wide temperature range of the liquid crystal phase, and a low viscosity.
- the compound of the present invention can be synthesized by appropriately combining methods in organic synthetic chemistry. Methods for introducing the desired end groups, rings and linking groups into the starting materials are described in Organic Syntheses, John Wiley & Sons, Inc., Organic Reactions, John Wiley & Sons, Inc., Included in omprehensive Organic Synthesis, Pergamon Press, New; ⁇ Experience Course (Maruzen)!
- MSG 1 or MSG 2 is a monovalent organic group having at least one ring.
- a plurality of MSG 1 (or MSG 2) used in the scheme may be the same or different.
- Compound (1A) to Compound (1K) correspond to Compound (1), Compound (2), Compound (11) to Compound (19), or Compound (2-1) to Compound (2-9) .
- n-BuLi, ii)) n-BuLi
- Compound (1A) is synthesized by reacting arylboric acid (21) with compound (22) synthesized by a known method in the presence of a carbonate solution and a catalyst such as tetrakis (triphenylphosphine) palladium. .
- This compound (1A) is obtained by reacting compound (23) synthesized by a known method with n-butyllithium and then with zinc chloride, to give dichlorobis (triphenyl N) Palladium is also synthesized by reacting compound (22) in the presence of a catalyst such as palladium.
- Compound (23) is reacted with n-butyllithium and subsequently with carbon dioxide to obtain carboxylic acid (24).
- Compound (24) and phenol (25) synthesized by a known method are dehydrated in the presence of DDC (1,3-dicyclohexyl carpositimide) and DMAP (4-dimethylaminopyridine) to remove COO.
- the compound (1B) having is synthesized.
- a compound having OCO is also synthesized by this method.
- Compound (1B) is treated with a sulfurizing agent such as Lawson's reagent to give compound (26).
- Compound (26) is fluorinated with hydrogen fluoride pyridine complex and NBS (N bromosuccinimide) to synthesize compound (1C) with -CF 2 O (M. uroboshi et al., Chem. Lett., 1992,
- Compound (1C) can also be synthesized by fluorinating Compound (26) with (Jetylamino) sulfur trifluoride (DAST) (see WH Bunnelle et al., J. Org. Chem. 1990, 55, 768.) .
- DAST Jetylamino sulfur trifluoride
- a compound having OCF is also synthesized by this method. Peer.
- linking groups can also be generated by the method described in irsch et al., Anbew. Chem. Int. Ed. 2001, 40, 1480.
- Compound (1G) is synthesized by hydrogenating compound (1E) in the presence of a catalyst such as palladium / carbon.
- Compound (1F) Compound (1H) is synthesized by catalytic hydrogenation in the presence of a catalyst such as palladium on carbon.
- the compound (23) is treated with n-butyllithium and then reacted with tetrafluoroethylene to obtain the compound (32).
- the compound (22) is treated with n-butyllithium and then reacted with the compound (32) to synthesize the compound (II).
- Compound (33) is obtained by reducing compound (29) with a reducing agent such as sodium borohydride. This is halogenated with hydrobromic acid or the like to obtain compound (34).
- Compound (1J) is synthesized by reacting compound (34) with compound (25) in the presence of potassium carbonate or the like.
- the compound (39) is synthesized by the method disclosed in JP-A-58-126823, JP-A-58-121225, JP-A-59-016840, or JP-A-59-042329. This is synthesized by reacting the 3 fluorobenzene derivative (38) with sec butyllithium, then dimethylformamide or formylpiperidine. These reactions are preferably carried out in a solvent such as ether hydrocarbon such as jetyl ether or tetrahydrofuran at a temperature between 100 ° C. and room temperature.
- Compound (1) is synthesized by reacting compound (39) with a fluorinating agent such as DAST.
- R is alkyl having 119 carbon atoms.
- Compound (41) is synthesized by sequentially reacting compound (40) with sodium hydride and chloromethyl methyl ether (MOMC1). These reactions are preferably carried out in a solvent such as tetrahydrofuran at a temperature between 20 ° C. and the boiling point of the solvent.
- Compound (42) is synthesized by reacting compound (41) with sec butyllithium and then dimethylformamide or formylpiperidine. These reactions are preferably carried out in a solvent such as ether hydrocarbons such as jetyl ether or tetrahydrofuran, at temperatures between 100 ° C. and room temperature.
- Compound (43) is synthesized by reacting compound (42) with a fluorinating agent such as DAST.
- This reaction is carried out in a solvent such as a halogenated hydrocarbon such as dichloromethane at a temperature between 100 ° C. and the boiling point of the solvent.
- Compound (44) is synthesized by deprotection of compound (43). This reaction is performed by reacting dilute hydrochloric acid such as 2M hydrochloric acid in an alcohol such as ethanol at a temperature between room temperature and the boiling point of the solvent.
- Compound (45) is synthesized by the etherification reaction of compound (44).
- This reaction is carried out in the presence of a base such as sodium carbonate by reacting compound (44) with an alkyl halide such as alkyl iodide at a temperature between room temperature and the boiling point of the solvent in a solvent such as dimethylformamide.
- a base such as sodium carbonate
- np and q are greater than or equal to 1, and Z 2 is — OCO— — OCF — OCF (
- the compounds (46) to (50) are respectively synthesized by using the compound (44) in place of the alcohol (phenol) intermediate in the above-described method for producing a linking group.
- Y, Z U , Z 12 , Z 2 , Z 21 or Z 22 is a single bond
- Compounds (60) and (63) in which A U , A 12 , A 2 , A 21 or A 22 is 1,4 phenylene can be synthesized by the following method in addition to the above synthesis method.
- Compound (60) is synthesized by reacting compound (58) with boric acid compound (59). These reactions preferably use a metal catalyst in a solvent such as an aromatic hydrocarbon such as toluene, an ether hydrocarbon such as dioxane or ethylene glycol dimethyl ether in the presence of a base such as potassium phosphate or carbonated lithium. At a temperature between room temperature and the boiling point of the solvent. Tetrakis (triphenylphosphine) palladium, dichlorobis (triphenylphosphine) palladium, palladium carbon, etc. are used as the metal catalyst.
- Compound (63) is used in the reaction route for synthesizing compound (60) from compound (57) described above! /, And instead of compound (57) and compound (59), compound (44) and The compound (62) is used and synthesized by applying the same reaction procedure.
- the compound (64) is disclosed in JP-A-58-126823, JP-A-58_121225, JP-A-59-016840, or JP-A-59-042329. It is synthesized by reacting the 3 fluorobenzene derivative (38) synthesized by the method with sec butyllithium and then iodine. These reactions are preferably carried out in solvents such as jet hydrocarbons such as jetyl ether or tetrahydrofuran, at temperatures between 100 ° C. and room temperature.
- solvents such as jet hydrocarbons such as jetyl ether or tetrahydrofuran
- Compound (64) is synthesized by reacting methyl fluorosulfonyldifluoroacetate in the presence of cuprous iodide. This reaction is dimethyl Perform in an aprotic polar solvent such as honremamide or dimethyl sulfoxide at a temperature between 60 ° C and the boiling point of the solvent.
- aprotic polar solvent such as honremamide or dimethyl sulfoxide
- n, p and q are 0, Rb is alkoxy, W is —CH ⁇ CH 1, and compound (69) and W is — (CH 2) 1 )
- R in these formulas is alkyl having 1 to 19 carbon atoms.
- compound (66) is synthesized by reacting compound (65) described in Synlett 1999, No. 4, 389-396 with sec-butyllithium and then N-formylpiperidine. These reactions are preferably carried out in a solvent such as ether hydrocarbon such as jetyl ether or tetrahydrofuran at a temperature between 100 ° C. and room temperature.
- Compound (68) is synthesized by allowing Grignard reagent (67) to act on compound (66) and then dehydrating the resulting alcohol in the presence of an acid catalyst such as p-toluenesulfonic acid.
- Compound (69) is synthesized by acting on (68) a THF solution of cesium fluoride or tetraptylammonium fluoride in N, N dimethylformamide.
- Compound (70) can be synthesized by adding hydrogen to compound (69) in the presence of a catalyst such as Pd / C.
- a catalyst such as Pd / C.
- n, p and q are 0, Rb is alkoxy, W is —CH 2 O—
- R in these formulas is alkyl having 1 to 19 carbon atoms.
- the compound (71) can be obtained by reacting the compound (65) described in Synlett 1999, No. 4, 389-396 with sec butyllithium and then bromine. Synthesize. These reactions are preferably carried out in a solvent such as ether hydrocarbon such as jetyl ether or tetrahydrofuran at a temperature between 100 ° C. and room temperature.
- Compound (72) is synthesized by acting compound (71) on a THF solution of cesium fluoride or tetraptyl ammonium fluoride in N, N dimethylformamide.
- Compound (73) is synthesized by reacting compound (72) with a borate ester such as dimethylborate with n-butyllithium, then!
- Compound (74) is synthesized by allowing hydrogen peroxide to act on compound (73).
- Compound (76) can be synthesized by reacting compound ( 74 ) with a halide such as compound (75) under basic conditions.
- Q 3 Ra- (A 1 2 -Z 12 ) — (A 1 1 -Z 1 1 ) —
- R is alkyl having 1 to 19 carbon atoms.
- the compounds (77) to (80) are respectively synthesized by using the compound (74) in place of the alcohol (phenol) intermediate in the above-described method for producing a linking group.
- composition of the present invention will be described in more detail.
- the components of this composition are compound (1) and compound (2), preferably compound (11) to compound (19) and compound (2— ;!) to compound (2-9) It's possible to have only one compound! / Preferable! /
- the composition contains at least one compound selected from compound (1 1) to compound (19) and compound (2-1) to compound (2-9) in a ratio of 1 to 99%. contains.
- This composition also contains a component selected from the compound (3) to the compound (15) group power.
- components are selected in consideration of the dielectric anisotropy of compound (1) and compound (2).
- a preferred composition containing a compound selected from the compound (1) and the compound (2), which has a negative dielectric anisotropy and a medium value is as follows. This preference! /, The composition is at least one selected from the group consisting of compound (3), compound (4) and compound (5) Contains one compound. Another preference! / Composition comprises at least one compound selected from the group consisting of compound (6-1), compound (6-2) and compound (7). Another preferred composition comprises at least two compounds selected from each of these two groups. These compositions are used for the purpose of adjusting the temperature range, viscosity, optical anisotropy, dielectric anisotropy, threshold voltage, etc. of the liquid crystal phase, compound (13), compound (14) and compound (15).
- compositions may further contain at least one compound selected from the group consisting of: These compositions may further contain at least one compound selected from the group consisting of compound (8) to compound (12) for the purpose of further adjusting the physical properties. These compositions may further contain compounds such as other liquid crystal compounds and additives for the purpose of adapting to AM TN devices, STN devices and the like.
- Another preferred composition contains at least one compound selected from the group consisting of compound (13), compound (14) and compound (15).
- This composition may further contain at least one compound selected from the group consisting of compound (8) to compound (12) for the purpose of further adjusting the physical properties.
- This composition may further contain compounds such as other liquid crystalline compounds and additives for the purpose of adapting to AM-TN devices, STN devices and the like.
- compositions and compositions containing a compound selected from the compound (1) and the compound (2) exhibiting a large negative negative dielectric anisotropy are as follows.
- the composition contains at least one compound selected from the group consisting of compound (8) to compound (13).
- This composition may further contain at least one compound selected from the group consisting of compound (13), compound (14) and compound (15).
- This composition may further contain at least one compound selected from the group consisting of compounds (3) to (7) for the purpose of further adjusting the physical properties.
- This composition may further contain other liquid crystalline compounds, additives and other compounds for the purpose of adapting to VA devices and the like.
- Another preferred composition contains at least one compound selected from the group consisting of compound (13), compound (14) and compound (15). This composition may further contain at least one compound selected from the group consisting of compound (8) to compound (12). This composition may further contain at least one compound selected from the group consisting of compound (3) to compound (7). This composition contains other liquid crystalline compounds, additives, etc. A compound may be further contained.
- a preferred composition containing a compound selected from the compound (1) and the compound (2) having a negative dielectric anisotropy and a small numerical value is as follows.
- the composition comprises at least one compound selected from the group consisting of compound (3), compound (4) and compound (5).
- Another preference! / The composition contains at least one compound selected from the group consisting of compound (6-1), compound (6-2) and compound (7) force.
- Another preferred composition contains at least two compounds selected from each of the two such groups.
- composition may further contain at least one compound selected from the group consisting of compound (8) to compound (12) for the purpose of further adjusting the physical properties.
- This composition may further contain compounds such as other liquid crystal compounds and additives for the purpose of adapting to AM-TN devices, STN devices and the like.
- Another preferred composition contains at least one compound selected from the group consisting of compound (8) to compound (12).
- This composition may further contain at least one compound selected from the group consisting of compound (13), compound (14) and compound (15).
- This composition may further contain at least one compound selected from the group consisting of compound (3) to compound (7) for the purpose of further adjusting the physical properties.
- This composition may further contain a compound such as other liquid crystalline compounds and additives for the purpose of adapting to a VA device and the like.
- the compound (3), the compound (4) and the compound (5) have a positive and large dielectric anisotropy, and are therefore mainly used in compositions for AM-TN devices.
- the amount of these compounds is;!-99%.
- a preferred amount is 10-97%.
- a more preferred amount is 40 to 95%.
- the preferred amount of this compound is 60% or less.
- a more preferred amount is 40% or less.
- Compound (6-1), Compound (6-2), and Compound (7) have very high positive dielectric anisotropy. Since it is large, it is mainly used in compositions for STN devices. In this composition, the amount of these compounds is 1 to 99%. A preferred amount is 10-97%. A more preferred amount is 40 to 95%. When compound (13), compound (14) or compound (15) is further added to this composition, the preferred amount of this compound is 60% or less. A more preferred amount is 40% or less.
- compound (8) to compound (12) have negative dielectric anisotropy, they are mainly used in compositions for VA devices.
- the preferred amount of these compounds is 80% or less. A more preferred amount is 40-80%.
- compound (13), compound (14) or compound (15) is further added to this composition, the preferred amount of this compound is 60% or less. A more preferred amount is 40% or less.
- the dielectric anisotropy of the compounds (13), (14) and (15) is small.
- the compound (13) is mainly used for the purpose of adjusting viscosity or optical anisotropy.
- Compound (14) and Compound (15) are used for the purpose of increasing the temperature range of the liquid crystal phase by increasing the maximum temperature or adjusting the optical anisotropy.
- Increasing the amount of compound (13), compound (14) and compound (15) increases the threshold voltage of the composition and decreases the viscosity. Therefore, it can be used in large amounts as long as the composition threshold is satisfied!
- Compound (3) to Compound (15) are preferred! / Examples are Compound (3-1) to Compound (3-9), Compound (4 1) to Compound (4-97), Compound (5-1) to Compound (5-33), Compound (6-1) to Compound (6-56), Compound (7-1) to Compound (7-3), Compound (8-1) to Compound ( 8-4), Compound (9-1) to Compound (9-6), Compound (10-1) to Compound (10-4), Compound (1 1 1), Compound (12-1), Compound (13 — 1) to Compound (13-14), Compound (14 1 ;! to Compound (1431), and Compound (15-1) to Compound (15-6).
- the symbols in these compounds have the same meaning as the symbols in compounds (3) to (15).
- the composition of the present invention is prepared by a known method.
- the component compounds are mixed and dissolved in each other by heating.
- Appropriate additives may be added to the composition to adjust the physical properties of the composition.
- Such additives are well known to those skilled in the art.
- a composition for a GH device may be prepared by adding a dichroic dye which is a compound such as merocyanine, styrinole, azo, azomethine, azoxy, quinophthalone, anthraquinone, and tetrazine.
- a chiral dopant is added for the purpose of inducing the helical structure of the liquid crystal to give the necessary twist angle. Examples of chiral dopants are the following optically active compounds (Op— ;!) to (Op—13).
- Chiralde pant added to composition And the preferred pitch for TN-TFT devices is in the range of 40-200 m: preferred for STN devices! /, The pitch is in the range of 6-20 am: preferred for BTN devices! /, The pitch is It is in the range of 1 ⁇ 5 to 4 ⁇ m: A relatively large amount of chiral dopant is added to the composition for PC elements. In order to adjust the temperature dependence of the pitch, at least two chiral dopants may be added.
- the composition of the present invention can be used in devices such as PC, TN, STN, BTN, ECB, OCB, IPS, and VA. These elements may be driving force or AM.
- NCAP nonematic curvilinear aligned phase
- PD polymer dispersed
- f row xJiPN polymer network element
- the ratio (percentage) of the component or the liquid crystal compound is a weight percentage (% by weight) based on the total weight of the liquid crystal compound.
- the composition is prepared by measuring the weight of a component such as a liquid crystal compound and then mixing them. Therefore, it is easy to calculate the weight percentage of the component. However, it is not easy to accurately calculate the component ratio by gas chromatographic analysis of the composition. This is because the correction coefficient depends on the type of liquid crystal compound. Fortunately, the correction factor is almost 1. Furthermore, a 1% by weight difference in the component compounds has little effect on the properties of the composition. Therefore, in the present invention, the area ratio of the component peak in the gas chromatograph can be regarded as the weight% of the component compound.
- the results of gas chromatographic analysis can be considered to be equivalent to the weight percent of the liquid crystal compound without correction.
- characteristic values there are three methods: when a compound is used as it is as a sample, when a compound is mixed with mother liquid crystals and used as a sample, and when a composition is used as a sample as it is.
- the ratio of the compound to the base liquid crystal is 10% by weight: 90% by weight, 5% by weight: 95% by weight, 1% by weight: 99% by weight. The order was changed.
- mother liquid crystal A The composition of the mother liquid crystal A is as follows.
- the crystal was represented as C.
- the crystals can be distinguished, they are expressed as C or C, respectively.
- the tic phase is represented as S.
- the liquid (isotropic) was expressed as Iso.
- the nematic phase is represented as N.
- the smectic phase can be distinguished from the smectic B phase, smectic C phase, or smectic A phase, they are expressed as S, S, or S, respectively.
- transition temperature “C”
- the upper limit temperature of the nematic phase may be abbreviated as “upper limit temperature”.
- a sample having a nematic phase is stored in a freezer at 0 ° C., 1 ° C., 1 20 ° C., 1 30 ° C., and 40 ° C. for 10 days, and the liquid crystal phase is observed.
- T is written as -20 ° C.
- the minimum temperature of the nematic phase may be abbreviated as “minimum temperature”
- a mother liquid crystal having a nematic phase is prepared by mixing several compounds having a similar structure.
- a composition in which the compound to be measured and this mother liquid crystal are mixed is obtained.
- An example of the mixing ratio is 15% compound and 85% mother liquid crystal.
- the distance (gap) between the two glass substrates is (0 ⁇ 5 / ⁇ ) ⁇ m, and the twist angle is 80 degrees.
- a sample is placed in a normally white mode liquid crystal display device.
- ⁇ is a value of optical anisotropy measured by the above method.
- a rectangular wave with a frequency of 32 ⁇ is applied to this element. Raise the voltage of the rectangular wave and measure the voltage value when the transmittance of light passing through the element reaches 90%.
- the distance between the two glass substrates (gap) is approximately 9,1 m, and the sample is placed in a normally black mode liquid crystal display device that has been processed in home-to-mouth orientation.
- a rectangular wave with a frequency of 32 Hz is applied to this element. Raise the voltage of the square wave and measure the voltage value when the transmittance of light passing through the element reaches 10%.
- DRX-500 manufactured by Bruker Biospin Co., Ltd.
- Deuterium such as CDC1
- TMS Tetramethylsilane
- GC-14B gas chromatograph manufactured by Shimadzu Corporation was used for the measurement.
- the carrier gas is helium (2 ml / min).
- the sample vaporization chamber was set to 280 ° C and the detector (FID) was set to 300 ° C.
- a chiral column DB-1 (length 30111, inner diameter 0.32 mm, film thickness 0.25 m; dimethylpolysiloxane; nonpolar) made by Agilent Technologies Inc. was used.
- the column was held at 200 ° C for 2 minutes and then heated to 280 ° C at a rate of 5 ° C / min.
- the sample was prepared in an acetone solution (0.1% by weight), and 1 ⁇ 1 was injected into the sample vaporization chamber.
- the recorder is a C-R5A Chromatopac manufactured by Shimadzu Corporation, or an equivalent.
- the obtained gas chromatogram showed the retention time and peak area corresponding to the component compounds.
- HP—1 length 30m, ID 0 ⁇ 32mm, film thickness 0 ⁇ 25m
- Rtx—1 length 30m, ID 0.32mm, film thickness 0.25mm
- BP-1 length 30m, inner diameter 0 ⁇ 32mm, film thickness 0 ⁇ 25 111).
- a single-force ram CBP1——50-025 (length 50 m, inner diameter 0.25 mm, film thickness 0.25 mm) manufactured by Shimadzu Corporation may be used.
- the area ratio of peaks in the gas chromatogram corresponds to the ratio of component compounds.
- the weight percentage of the component compounds is not completely the same as the area ratio of each peak. However, in the present invention, when these column columns are used, the weight percentage of the component compounds may be regarded as being the same as the area ratio of each peak. This is because there is no significant difference in the correction coefficients of the component compounds.
- a THF solution of 2-fluoro-4-ethoxybromobenzene is added dropwise to the dried shaved magnesium at 40 60 ° C.
- To this solution is added dropwise THF solution of 4 (Provircyclohexyl) cyclohexanone at 40 60 ° C and stirred for another 2 hours.
- the reaction mixture is poured into saturated aqueous ammonium chloride and extracted with toluene.
- the organic layer is washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
- the resulting crude 1-hydroxy-4 4 propyl cyclohexyl cyclohexyl lu 2 fluoroethoxybenzene is used in the second step without purification.
- the aqueous layer was extracted with 100 ml of ethyl acetate, and the organic layer was mixed, washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product. 22.3 g of 3-fluoro-4-ethoxyphenylpolonic acid was obtained. The obtained boric acid derivative was used in the second step without purification.
- the concentrated residue was purified by silica gel column chromatography using a mixed solvent of ethyl acetate / heptane as an eluent to obtain 17 ⁇ 6 g (l l 3 mmol) of 3-fluoro-4-ethoxyphenol.
- the extract layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
- the organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography using a mixed solvent of ethyl acetate / heptane as a developing solvent. Purify and obtain This one more The product was purified by repeated recrystallization to obtain 7.6 g of 2 difluoromethyl 1-3 fluoro 4 ethoxyphenyl methoxymethyl ether.
- the resulting crude triflate derivative (5.5 g) was 4- (propyl cyclohexyl) phenylboric acid 3.2 g (13.2 mmol), potassium bromide 1.6 g (13.2 mmol), potassium phosphate 5 ⁇ lg (24 mmol), 50 ml of dioxane, and 0.4 g (0.3 mmol) of tetrakistriphenylphosphine palladium as a coupling catalyst were mixed and heated to reflux for 5 hours. The reaction mixture was poured into water and extracted with 100 ml of toluene, and then the organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
- the concentrated residue was purified by silica gel column chromatography using a mixed solvent of ethyl acetate / heptane as an eluent, and further purified by repeated recrystallization from a mixed solvent of heptane / ethanol. Hexinole) phenyl-2-fluoro-3 difluoromethyl-ethoxybenzene was obtained. The melting point of this compound was 82.2 ° C.
- 2-Fluoro-4-methylphenyl methoxymethyl ether obtained in the first step is dissolved in terahydrofuran and cooled to 70 ° C under a nitrogen atmosphere and acetone dry ice refrigerant.
- To this solution is added sec butyl lithium dropwise under a nitrogen atmosphere, and the mixture is stirred at 70 ° C for 1 hour.
- dimethylformamide is added dropwise at -70 ° C.
- the mixture is stirred at the same temperature for 2 hours.
- the reaction mixture is poured into saturated aqueous ammonium chloride and extracted with hexane.
- the organic layer is washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
- the resulting residue is purified by silica gel column chromatography to obtain 2 fluoro-3 formyl-4 methylphenyl methoxymethyl ether.
- Fluoro-3 formyl-4 methylphenyl methoxymethyl ether obtained in the second step is dissolved in dichloromethane and cooled to 0 ° C. in a nitrogen atmosphere, and then added with jetylaminosulfur trifluoride (DAST) at room temperature. Stir for hours.
- the solution is poured into an aqueous sodium hydrogen carbonate solution and extracted with heptane.
- the organic layer is washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Concentrated residue Is purified by silica gel column chromatography to obtain 2 fluoro 3 difluoromethylolene 4 methylphenyl methoxymethyl ether.
- Ethylphenylboric acid is mixed with 3-fluoro-4-sulfinpalladium in a toluene / ethanol mixed solvent and heated to reflux for 8 hours.
- the reaction mixture is poured into water and extracted with 100 ml of toluene.
- the organic layer is washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
- the concentrated residue is purified by silica gel column chromatography. And purified by repeated recrystallization to obtain pure 3-fluoro-4- (4-ethylphenyl) anisole.
- 3-Fluoro-4 (4-ethylphenyl) phenyl methoxymethyl ether obtained in the third step is dissolved in terahydrofuran and cooled to 70 ° C under a nitrogen atmosphere and acetone dry ice refrigerant.
- To this solution add sec butyl lithium dropwise under a nitrogen atmosphere, and then stir at -70 ° C for 1 hour.
- dimethylformamide is added dropwise at -70 ° C, followed by stirring at the same temperature for 2 hours.
- the reaction mixture is poured into saturated aqueous ammonium chloride and extracted with hexane.
- the organic layer is washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
- Step 5 2-Honoreminole 3-Funoreo port 4- (4-Ethenolefenole) phenol methoxymethyl ether obtained in Step 4 is dissolved in dichloromethane and cooled to 0 ° C in a nitrogen atmosphere. Add orido (DAST) and stir at room temperature for 20 hours. The solution is poured into an aqueous sodium hydrogen carbonate solution and extracted with heptane. The organic layer is washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The concentrated residue is purified by silica gel column chromatography to obtain 2-difluoromethenole 3-funoleo port 4 4 ethino ref.
- DAST orido
- 2-Difluoromethyl 3-fluoro-4- (4-ethylphenyl) phenol and pyridine obtained in the sixth step are dissolved in dichloromethane, and trifluoromethanesulfonic anhydride is added at about 5 ° C under a nitrogen atmosphere, and the mixture is heated at the same temperature for 2 hours. Stir.
- the reaction mixture is poured into an aqueous sodium hydrogen carbonate solution and extracted with dichloromethane.
- the organic layer is washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude triflate derivative.
- the resulting crude triflate derivative is mixed with 4 pentylphenylboric acid, potassium bromide, and potassium phosphate in dioxane, tetrakistriphenylphosphine palladium is added as a coupling catalyst, and the mixture is heated to reflux for 8 hours.
- the reaction mixture is poured into water and extracted with toluene.
- the organic layer is washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
- the concentrated residue is purified by silica gel column chromatography, and further purified by repeated recrystallization to obtain pure 4 pentyl-2 'difluoromethyl 3'-fluoro 4 "-ethyl terphenyl.
- reaction mixture was poured into 100 ml of saturated ammonium chloride water and extracted with 200 ml of toluene.
- the organic layer was washed sequentially with 100 ml of water and 100 ml of saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and crude 1-hydroxy 1 1 1 (2-trifluoromethyl-3 fluoro-4 ethoxy-5 trimethylsilylphenyl). 20-7 g of) -2— (4 (4 (propyl) cyclohexyl) cyclohexyl) ethane was obtained.
- Example 7 ⁇ - (4- (4-Propylcyclohexyl) cyclohexyl) 2-trifluoromethyl-3 fluoro-4-etoxystyrene obtained in Example 7 7.89 g was dissolved in 200 mL of a toluene solvent mixture solvent. . A palladium carbon catalyst was added to this solution under a nitrogen atmosphere, and a hydrogenation reaction was performed at room temperature and pressure for 2 days. After completion of the reaction, the catalyst was removed by filtration.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006511662A JP5145711B2 (ja) | 2004-04-01 | 2005-03-29 | ベンゼン誘導体、液晶組成物および液晶表示素子 |
US10/593,874 US7838087B2 (en) | 2004-04-01 | 2005-03-29 | Benzene derivative, liquid crystal composition and liquid crystal display device |
EP05727795A EP1731493B1 (en) | 2004-04-01 | 2005-03-29 | Benzene derivative, liquid crystal composition and liquid crystal display |
DE602005027060T DE602005027060D1 (de) | 2004-04-01 | 2005-03-29 | Benzolderivat, flüssigkristallzusammensetzung und flüssigkristallanzeige |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004-108969 | 2004-04-01 | ||
JP2004108969 | 2004-04-01 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2005095311A1 WO2005095311A1 (ja) | 2005-10-13 |
WO2005095311A9 true WO2005095311A9 (ja) | 2008-03-13 |
Family
ID=35063676
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2005/005837 WO2005095311A1 (ja) | 2004-04-01 | 2005-03-29 | ベンゼン誘導体、液晶組成物および液晶表示素子 |
Country Status (6)
Country | Link |
---|---|
US (1) | US7838087B2 (ja) |
EP (1) | EP1731493B1 (ja) |
JP (2) | JP5145711B2 (ja) |
DE (1) | DE602005027060D1 (ja) |
TW (1) | TWI329099B (ja) |
WO (1) | WO2005095311A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1958945B1 (en) * | 2005-12-08 | 2014-11-12 | JNC Corporation | Compound having hydrocoumarin skeleton, liquid crystal composition and liquid crystal display element |
EP1935962A1 (en) * | 2006-12-19 | 2008-06-25 | Merck Patent GmbH | Liquid-crystalline medium |
GB201301786D0 (en) * | 2012-02-15 | 2013-03-20 | Merck Patent Gmbh | Liquid-crystalline medium |
JP6052033B2 (ja) | 2012-04-24 | 2016-12-27 | Jnc株式会社 | 負の誘電率異方性を示す液晶性化合物、液晶組成物および液晶表示素子 |
JP6413790B2 (ja) | 2014-02-05 | 2018-10-31 | Jnc株式会社 | カルボニル誘導体、これらの化合物を含有する液晶組成物および液晶表示素子 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4338348B4 (de) | 1992-11-19 | 2006-05-11 | Merck Patent Gmbh | 2,6-Disubstituierte Benzotrifluoride |
JP3702426B2 (ja) * | 1994-08-03 | 2005-10-05 | 関東化学株式会社 | トリフルオロメチルベンゼン誘導体および液晶組成物 |
DE19982965B3 (de) * | 1998-12-25 | 2012-08-30 | Jnc Corporation | Flüssigkristalline Verbindung mit einem negativen Wert der dielektrischen Anisotropie |
JP4595293B2 (ja) * | 2002-06-07 | 2010-12-08 | チッソ株式会社 | プロピオン酸エステル誘導体、該誘導体を含有する液晶組成物及び該液晶組成物を含有する液晶表示素子 |
JP2005298734A (ja) * | 2004-04-14 | 2005-10-27 | Chisso Corp | 液晶組成物および液晶表示素子 |
JP2005298733A (ja) * | 2004-04-14 | 2005-10-27 | Chisso Corp | 液晶組成物および液晶表示素子 |
JP4857552B2 (ja) * | 2004-12-06 | 2012-01-18 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
-
2005
- 2005-03-29 EP EP05727795A patent/EP1731493B1/en not_active Expired - Fee Related
- 2005-03-29 DE DE602005027060T patent/DE602005027060D1/de active Active
- 2005-03-29 JP JP2006511662A patent/JP5145711B2/ja not_active Expired - Fee Related
- 2005-03-29 US US10/593,874 patent/US7838087B2/en not_active Expired - Fee Related
- 2005-03-29 WO PCT/JP2005/005837 patent/WO2005095311A1/ja active Application Filing
- 2005-03-30 TW TW094109948A patent/TWI329099B/zh not_active IP Right Cessation
-
2011
- 2011-03-30 JP JP2011076033A patent/JP5488514B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
DE602005027060D1 (de) | 2011-05-05 |
WO2005095311A1 (ja) | 2005-10-13 |
JP5145711B2 (ja) | 2013-02-20 |
JP5488514B2 (ja) | 2014-05-14 |
TW200604142A (en) | 2006-02-01 |
EP1731493B1 (en) | 2011-03-23 |
TWI329099B (en) | 2010-08-21 |
JPWO2005095311A1 (ja) | 2008-02-21 |
EP1731493A4 (en) | 2009-01-21 |
JP2011173894A (ja) | 2011-09-08 |
US20070200092A1 (en) | 2007-08-30 |
US7838087B2 (en) | 2010-11-23 |
EP1731493A1 (en) | 2006-12-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI412577B (zh) | 液晶性化合物、液晶組成物以及液晶顯示元件 | |
TWI475096B (zh) | 具有側向氟元素之4環液晶性化合物、液晶組成物以及液晶顯示元件 | |
TWI460259B (zh) | 具有側向氟的4、5環液晶性化合物、液晶組成物以及液晶顯示元件 | |
TWI320054B (en) | Liquid-crystalline compounds | |
JP5163019B2 (ja) | アルケニルを有するシクロヘキセン誘導体、液晶組成物および液晶表示素子 | |
JP6098415B2 (ja) | 2、2−ジフルオロビニルオキシ基または1、2、2−トリフルオロビニルオキシ基を有する化合物、液晶組成物および液晶表示素子 | |
US20090230356A1 (en) | Compound having alkyl on benzene ring, liquid crystal composition having the compound, and liquid crystal display device having the liquid crystal composition | |
JP5163018B2 (ja) | クロロフルオロベンゼン系液晶性化合物、液晶組成物および液晶表示素子 | |
TWI589679B (zh) | 液晶化合物、液晶組成物及液晶顯示元件 | |
KR20080022526A (ko) | 클로로플루오로벤젠계 액정성 화합물, 액정 조성물 및 액정표시 소자 | |
KR20100068380A (ko) | 액정성 화합물, 액정 조성물 및 액정 표시 소자 | |
TWI437081B (zh) | 介電常數各向異性為負之液晶化合物、液晶組成物以及液晶顯示元件 | |
JP6460089B2 (ja) | 1,1,3,3−テトラフルオロアリルオキシ基を有する液晶性化合物、液晶組成物、および液晶表示素子 | |
KR20110003484A (ko) | 레터럴 불소를 갖는 3 고리 액정성 화합물, 액정 조성물 및 액정 표시 소자 | |
TWI468381B (zh) | 十氫化萘化合物、含有此化合物的液晶組成物及含有此液晶組成物的液晶顯示元件 | |
TW201113354A (en) | Liquid crystal compound, liquid crystal composition and liquid crystal display device | |
JP2005035986A (ja) | クロマン化合物、この化合物を含有する液晶組成物およびこの液晶組成物を含有する液晶表示素子 | |
JP4940626B2 (ja) | ベンゼン環にアルキル基を有する化合物、この化合物を含有する液晶組成物およびこの液晶組成物を含有する液晶表示素子 | |
WO2009157313A1 (ja) | 誘電率異方性が負の液晶性化合物、液晶組成物および液晶表示素子 | |
JP5044919B2 (ja) | ベンゼン環にアルキル基を有する化合物、この化合物を含有する液晶組成物およびこの液晶組成物を含有する液晶表示素子 | |
JP2005314385A (ja) | ベンゼン誘導体、液晶組成物および液晶表示素子 | |
JP5315590B2 (ja) | 液晶化合物、液晶組成物および液晶表示素子 | |
JP5488514B2 (ja) | ベンゼン誘導体、液晶組成物および液晶表示素子 | |
JP6439450B2 (ja) | フッ素を含有するアルケニル末端基を有する液晶性化合物、液晶組成物および液晶表示素子 | |
JP6115303B2 (ja) | 隣接基としてカルボニル基を有するフェノール化合物およびその用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2006511662 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2005727795 Country of ref document: EP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 10593874 Country of ref document: US Ref document number: 2007200092 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 2005727795 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 10593874 Country of ref document: US |