JPH08291179A - Dioxaborinane compound and liquid crystal containing same - Google Patents
Dioxaborinane compound and liquid crystal containing sameInfo
- Publication number
- JPH08291179A JPH08291179A JP7101441A JP10144195A JPH08291179A JP H08291179 A JPH08291179 A JP H08291179A JP 7101441 A JP7101441 A JP 7101441A JP 10144195 A JP10144195 A JP 10144195A JP H08291179 A JPH08291179 A JP H08291179A
- Authority
- JP
- Japan
- Prior art keywords
- group
- liquid crystal
- compound
- dioxaborinane
- atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 153
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 76
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims abstract description 7
- YDRZSEWRKSUWCS-UHFFFAOYSA-N O1BCOCC1 Chemical compound O1BCOCC1 YDRZSEWRKSUWCS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims 1
- 101150035983 str1 gene Proteins 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 22
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 21
- 101150065749 Churc1 gene Proteins 0.000 description 21
- 102100038239 Protein Churchill Human genes 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical class CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 16
- -1 2-substituted-1,3-propanediol Chemical class 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- GRRSDGHTSMJICM-UHFFFAOYSA-N diethyl 2-propylpropanedioate Chemical compound CCOC(=O)C(CCC)C(=O)OCC GRRSDGHTSMJICM-UHFFFAOYSA-N 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 150000004820 halides Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 8
- 210000002858 crystal cell Anatomy 0.000 description 8
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- FZHZPYGRGQZBCV-UHFFFAOYSA-N 2-propylpropane-1,3-diol Chemical compound CCCC(CO)CO FZHZPYGRGQZBCV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910006404 SnO 2 Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- ZYXZSRASZWYYFY-UHFFFAOYSA-N 2-ethoxycarbonylpentanoic acid Chemical compound CCCC(C(O)=O)C(=O)OCC ZYXZSRASZWYYFY-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 101100289792 Squirrel monkey polyomavirus large T gene Proteins 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000004313 glare Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、液晶材料として有用な
新規なジオキサボリナン化合物、および該化合物を含有
する液晶組成物、さらに該液晶組成物を用いた液晶電気
光学素子に関する。TECHNICAL FIELD The present invention relates to a novel dioxaborinane compound useful as a liquid crystal material, a liquid crystal composition containing the compound, and a liquid crystal electro-optical element using the liquid crystal composition.
【０００２】[0002]
【従来の技術】液晶表示素子は、時計、電卓をはじめ、
測定器、自動車用計器、複写器、カメラ、ＯＡ機器用表
示装置、家電製品用表示装置等種々の用途に使用されて
おり、広い動作温度範囲、低動作電圧、高速応答性、化
学的安定性等の種々の性能要求がなされている。2. Description of the Related Art Liquid crystal display devices include clocks, calculators,
It is used in various applications such as measuring instruments, measuring instruments for automobiles, copying machines, cameras, display devices for office automation equipment, and display devices for home appliances, and has a wide operating temperature range, low operating voltage, high-speed response, and chemical stability. There are various performance requirements such as.
【０００３】しかし、現在のところ、これらの特性を単
独の材料で全て満たす材料はなく、複数の液晶、およ
び、非液晶の材料を混合して液晶組成物として要求性能
を満たしている。このため、各種特性の全てではなく、
一または二以上の特性に優れた液晶または非液晶の材料
開発が望まれている。However, at present, there is no material satisfying all of these characteristics by a single material, and a plurality of liquid crystal and non-liquid crystal materials are mixed to satisfy the required performance as a liquid crystal composition. Therefore, not all of the various characteristics,
It is desired to develop liquid crystal or non-liquid crystal materials having one or more excellent characteristics.
【０００４】液晶表示素子の中でも、液晶ドットマトリ
ックス表示素子は、電子式卓上計算機をはじめとして、
各種事務機器、電子計算機の端末表示装置等に使用され
始めており、より見やすく、また、より表示画素数の大
きい液晶表示素子が求められている。また最近は、より
高画質の表示が求められており、焼き付き現象のような
表示不良を発生させない技術も求められている。Among the liquid crystal display elements, the liquid crystal dot matrix display element includes an electronic desk calculator,
It has been used for various office equipments, terminal display devices of electronic computers, and the like, and there is a demand for a liquid crystal display element that is easier to see and has a larger number of display pixels. Further, recently, there is a demand for higher quality display, and there is also a demand for a technique that does not cause a display defect such as a burn-in phenomenon.
【０００５】[0005]
【発明が解決しようとする課題】ドットマトリックス表
示とは、図形あるいは文字等の情報を点の集合として表
示するものであり、表示画素数が多くなるためにマルチ
プレックス駆動が必要になる。ＴＮ（ツイストネマチッ
ク）セルにおいては、当初１／７または１／８デューテ
ィで駆動された１行表示のセルが一般的であったが、最
近では１／３２デューティ、１／６４デューティ、さら
にはより高デューティの要求が生じ、ＴＮセルのマルチ
プレックス駆動特性を改良することが重要な課題となっ
ている。また、焼き付き現象のような表示不良を発生さ
せにくい液晶材料を提供することも重要な課題となって
いる。The dot matrix display is for displaying information such as a figure or a character as a set of dots and requires multiplex driving because the number of display pixels increases. In a TN (twisted nematic) cell, a one-row display cell driven at a 1/7 or 1/8 duty was general at first, but recently, a 1/32 duty, a 1/64 duty, and more With the demand for high duty, improving the multiplex drive characteristics of TN cells has become an important issue. It is also an important issue to provide a liquid crystal material that does not easily cause a display defect such as a burn-in phenomenon.
【０００６】[0006]
【課題を解決するための手段】本発明は、上記の問題を
解決するためになされたものであり、液晶化合物として
有用な、新規なジオキサボリナン化合物を提供する。ま
た、該化合物を含有する液晶組成物、および液晶電気光
学素子を提供する。本発明の化合物は、マルチプレック
ス駆動特性を改良するとともに、焼き付きを防止する優
れた化合物である。The present invention has been made to solve the above problems, and provides a novel dioxaborinane compound useful as a liquid crystal compound. Further, a liquid crystal composition containing the compound and a liquid crystal electro-optical element are provided. INDUSTRIAL APPLICABILITY The compound of the present invention is an excellent compound that improves multiplex driving characteristics and prevents image sticking.
【０００７】すなわち、本発明は、一般式（１）で表さ
れるジオキサボリナン化合物を提供する。That is, the present invention provides a dioxaborinane compound represented by the general formula (1).
【０００８】[0008]
【化５】 R1-(A1-Z1)k-B-(Z2-A2)p-(Z3-A3)m-Z4-(CH2)n-CX1=CFX2 （１）Embedded image R 1 - (A 1 -Z 1 ) k -B- (Z 2 -A 2) p - (Z 3 -A 3) m -Z 4 - (CH 2) n -CX 1 = CFX 2 (1)
【０００９】ただし、一般式（１）において、Ｒ1 、Ａ
1 、Ａ2 、Ａ3 、Ｂ、Ｚ1 、Ｚ2 、Ｚ3 、Ｚ4 、Ｘ1 、
Ｘ2 、ｋ、ｐ、ｍ、およびｎは下記の意味を示す。 Ｒ1 ：炭素数１〜１０のアルキル基またはアルケニル基
を示し、これらの基中の炭素−炭素結合間あるいはその
基と環との間の炭素−炭素結合間に、酸素原子が挿入さ
れていてもよい。However, in the general formula (1), R 1 , A
1 , A 2 , A 3 , B, Z 1 , Z 2 , Z 3 , Z 4 , X 1 ,
X 2 , k, p, m, and n have the following meanings. R 1 represents an alkyl group or an alkenyl group having 1 to 10 carbon atoms, and an oxygen atom is inserted between carbon-carbon bonds in these groups or between carbon-carbon bonds between the group and the ring. Good.
【００１０】Ａ1 、Ａ2 、Ａ3 ：それぞれ互いに独立し
て、（ａ）１つまたはそれ以上の隣接しないCH2 部分が
エーテル性の酸素原子で置換されていてもよいトランス
−１，４−シクロヘキシレン基、（ｂ）１つまたは２つ
のCH部分が、窒素原子で置換されていてもよい１，４−
フェニレン基、または（ｃ）１，４−シクロヘキセニレ
ン基を示し、（ａ）および（ｂ）は、それぞれ、基中の
水素原子がCN基またはフッ素原子で置換されていてもよ
い。 Ｂ：式（２）で表される２価の１，４−ジオキサボリナ
ン基を示す。A 1 , A 2 , A 3 : each independently of each other, (a) trans-1,4 in which one or more non-adjacent CH 2 moieties may be substituted with an etheric oxygen atom. A cyclohexylene group, (b) one or two CH moieties optionally substituted with nitrogen atoms, 1,4-
A phenylene group or (c) 1,4-cyclohexenylene group is shown, and in (a) and (b), a hydrogen atom in the group may be substituted with a CN group or a fluorine atom. B: A divalent 1,4-dioxaborinane group represented by the formula (2) is shown.
【００１１】[0011]
【化６】 [Chemical 6]
【００１２】Ｚ1 、Ｚ2 、Ｚ3 、Ｚ4 ：それぞれ互いに
独立して、-CO-O-、-O-CO-、-CH2O-、-OCH2-、-C≡C-、
-CH=CH- 、-CH2CH2-、または単結合を示す。 Ｘ1 ：水素原子、フッ素原子、または塩素原子を示す。 Ｘ2 ：水素原子、フッ素原子、塩素原子、トリフルオロ
メチル基、トリフルオロメトキシ基、炭素数１〜５のア
ルキル基、またはアルコキシ基を示す。 ｋ、ｐ、ｍ：それぞれ互いに独立して、０または１を示
し、ｋ＋ｐ＋ｍ≧１である。 ｎ：０〜４の整数を示す。Z 1 , Z 2 , Z 3 , Z 4 : Independently of each other, --CO--O--, --O--CO--, --CH 2 O--, --OCH 2- , --C≡C--,
-CH = CH-, -CH 2 CH 2 -, or a single bond. X 1 : represents a hydrogen atom, a fluorine atom or a chlorine atom. X 2 : A hydrogen atom, a fluorine atom, a chlorine atom, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group. k, p, m: each independently represent 0 or 1, and k + p + m ≧ 1. n: Shows an integer of 0 to 4.
【００１３】以下において、一般式（１）で表されるジ
オキサボリナン化合物を化合物（１）と記す。他の化合
物においても同様に記載する。In the following, the dioxaborinane compound represented by the general formula (1) is referred to as compound (1). The same applies to other compounds.
【００１４】化合物（１）のＲ1 は、炭素数１〜１０の
アルキル基または炭素数１〜１０のアルケニル基を示
す。Ｒ1 がアルキル基またはアルケニル基である場合、
該基は、いずれも直鎖の場合が好ましい。また、Ｒ1 が
アルケニル基である場合、炭素−炭素二重結合部分は、
Ｂから２個目の炭素原子と３個目の炭素原子の部分に存
在するのが好ましい。さらに、Ｒ1 は、基中の炭素−炭
素結合間あるいはその基と環との間の炭素−炭素結合間
に、酸素原子が挿入されていてもよい。R 1 of the compound (1) represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 1 to 10 carbon atoms. When R 1 is an alkyl group or an alkenyl group,
It is preferable that all the groups are linear. When R 1 is an alkenyl group, the carbon-carbon double bond moiety is
It is preferably present in the portion of the second carbon atom and the third carbon atom from B. Further, R 1 may have an oxygen atom inserted between carbon-carbon bonds in the group or between carbon-carbon bonds between the group and the ring.
【００１５】また、化合物（１）のＡ1 〜Ａ3 は、いず
れも非置換のトランス−１，４−シクロヘキシレン基、
非置換の１，４−フェニレン基、または１，４−シクロ
ヘキセニレン基が好ましく、特に、非置換のトランス−
１，４−シクロヘキシレン基、または非置換の１，４−
フェニレン基が好ましい。特に、Ａ2 は１，４−フェニ
レン基が好ましい。Further, A 1 to A 3 of the compound (1) are each an unsubstituted trans-1,4-cyclohexylene group,
An unsubstituted 1,4-phenylene group or a 1,4-cyclohexenylene group is preferable, and particularly, an unsubstituted trans-
1,4-cyclohexylene group or unsubstituted 1,4-
A phenylene group is preferred. Particularly, A 2 is preferably a 1,4-phenylene group.
【００１６】化合物（１）のｋは０である場合が好まし
く、ｐは１である場合が好ましい。さらに、ｐが１であ
る場合には、Ｚ2 は単結合が好ましい。また、ｎは０〜
２の整数が好ましい。化合物（１）は、環構造部分を２
個または３個有する化合物が好ましい。It is preferable that k of the compound (1) is 0, and p is 1. Further, when p is 1, Z 2 is preferably a single bond. Also, n is 0
An integer of 2 is preferred. The compound (1) has two ring structure parts.
Compounds with one or three are preferred.
【００１７】化合物（１）において、環構造部分を２個
有する化合物としては、下式の化合物が挙げられる。た
だし、下式において、Ｒ1 、Ａ1 、Ａ2 、Ｂ、Ｚ1 、Ｚ
2 、Ｚ4 、Ｘ1 、Ｘ2 、およびｎは前記と同じ意味を示
す。In the compound (1), examples of the compound having two ring structure moieties include the compounds of the following formulas. However, in the following formula, R 1 , A 1 , A 2 , B, Z 1 , Z
2 , Z 4 , X 1 , X 2 , and n have the same meanings as described above.
【００１８】[0018]
【化７】R1-B-(Z2-A2)-Z4-(CH2)n-CX1=CFX2（２Ａ） R1-(A1-Z1)-B-Z4-(CH2)n-CX1=CFX2（２Ｂ）Embedded image R 1 -B- (Z 2 -A 2 ) -Z 4 - (CH 2) n -CX 1 = CFX 2 (2A) R 1 - (A 1 -Z 1) -BZ 4 - (CH 2 ) n -CX 1 = CFX 2 (2B)
【００１９】化合物（２Ａ）および化合物（２Ｂ）の具
体例としては、実施例中に記載したものが挙げられる。
これらのうち、本発明においては、化合物（１）におけ
るｋおよびｍが０であり、ｐが１である場合の化合物
（２Ａ）が好ましい。さらに、化合物（２Ａ）は、Ｚ2
が単結合、Ａ2 が１，４−フェニレン基、である場合の
化合物（２Ａ’）が液晶としての物性等の点から好まし
い。Specific examples of the compound (2A) and the compound (2B) include those described in Examples.
Of these, in the present invention, compound (2A) in which k and m in compound (1) are 0 and p is 1 is preferable. Further, the compound (2A) is Z 2
Is a single bond and A 2 is a 1,4-phenylene group, the compound (2A ′) is preferable from the viewpoint of physical properties as a liquid crystal.
【００２０】[0020]
【化８】R1-B-Ph-Z4-(CH2)n-CX1=CFX2 （２Ａ’）Embedded image R 1 -B-Ph-Z 4 - (CH 2) n -CX 1 = CFX 2 (2A ')
【００２１】化合物（２Ａ’）において、Ｒ1 、Ｂ、Ｚ
4 、Ｘ1 、Ｘ2 、およびｎは前記と同じ意味を示す。ま
た、Ｐｈは、１，４−フェニレン基を示す。化合物（２
Ａ’）のＲ1 は、低級のアルキル基が好ましく、Ｘ1 は
水素原子またはフッ素原子が好ましく、Ｘ2 はフッ素原
子、塩素原子、またはトリフルオロメトキシ基が好まし
い。また、ｎは０〜２の整数が好ましい。化合物（２
Ａ’）の具体例としては実施例中に記載したものが挙げ
られる。In the compound (2A '), R 1 , B, Z
4 , X 1 , X 2 , and n have the same meanings as described above. Further, Ph represents a 1,4-phenylene group. Compound (2
R 1 of A ′) is preferably a lower alkyl group, X 1 is preferably a hydrogen atom or a fluorine atom, and X 2 is preferably a fluorine atom, a chlorine atom or a trifluoromethoxy group. Further, n is preferably an integer of 0-2. Compound (2
Specific examples of A ′) include those described in the examples.
【００２２】また、化合物（１）のうち、環構造を３個
有する化合物としては、化合物（３Ａ）、または化合物
（３Ｂ）が挙げられる。Among the compounds (1), examples of the compound having three ring structures include the compound (3A) and the compound (3B).
【００２３】[0023]
【化９】 R1-B-(Z2-A2)-(Z3-A3)-Z4-(CH2)n-CX1=CFX2（３Ａ） R1-(A1-Z1)-B-(Z2-A2)-Z4-(CH2)n-CX1=CFX2（３Ｂ）Embedded image R 1 -B- (Z 2 -A 2 ) - (Z 3 -A 3) -Z 4 - (CH 2) n -CX 1 = CFX 2 (3A) R 1 - (A 1 -Z 1) -B- (Z 2 -A 2 ) -Z 4 - (CH 2) n -CX 1 = CFX 2 (3B)
【００２４】ただし、化合物（３Ａ）および化合物（３
Ｂ）において、Ｒ1 、Ａ1 、Ａ2 、Ａ3 、Ｂ、Ｚ1 、Ｚ
2 、Ｚ3 、Ｚ4 、Ｘ1 、Ｘ2 、およびｎは前記と同じ意
味を示す。これらのうち、化合物（１）におけるｋが０
であり、ｐおよびｍが１である場合の化合物（３Ａ）が
好ましい。さらに化合物（３Ａ）は、Ｚ2 が単結合、Ａ
2 が１，４−フェニレン基、である場合の化合物（３
Ａ’）が液晶としての物性等の点から好ましい。However, the compound (3A) and the compound (3
In B), R 1 , A 1 , A 2 , A 3 , B, Z 1 , Z
2 , Z 3 , Z 4 , X 1 , X 2 , and n have the same meanings as described above. Among these, k in compound (1) is 0
And the compound (3A) when p and m are 1 is preferable. Furthermore, in the compound (3A), Z 2 is a single bond, A
A compound (3 in which 2 is a 1,4-phenylene group,
A ') is preferable from the viewpoint of physical properties as a liquid crystal.
【００２５】[0025]
【化１０】 R1-B-Ph-(Z3-A3)-Z4-(CH2)n-CX1=CFX2（３Ａ’）Embedded image R 1 -B-Ph- (Z 3 -A 3) -Z 4 - (CH 2) n -CX 1 = CFX 2 (3A ')
【００２６】化合物（３Ａ’）において、Ｒ1 、Ａ3 、
Ｂ、Ｚ3 、Ｚ4 、Ｘ1 、Ｘ2 、Ｐｈ、およびｎは前記と
同じ意味を示す。化合物（３Ａ’）のＲ1 は、低級のア
ルキル基が好ましく、Ｘ1 は水素原子またはフッ素原
子、Ｘ2 はフッ素原子、塩素原子、またはトリフルオロ
メトキシ基が好ましい。また、ｎは０〜２の整数が好ま
しい。化合物（３Ａ’）の具体例は、実施例中に記載し
たものが挙げられる。化合物（３Ａ’）は、比較的大き
なＴc （相転移温度）を有しているので、この化合物を
液晶組成物に添加した場合には、液晶組成物の透明点
（Ｎ−Ｉ）を引き上げる効果がある。すなわち、駆動温
度幅を拡張するための有効な材料である。In the compound (3A '), R 1 , A 3 ,
B, Z 3 , Z 4 , X 1 , X 2 , Ph, and n have the same meanings as described above. R 1 of the compound (3A ′) is preferably a lower alkyl group, X 1 is preferably a hydrogen atom or a fluorine atom, and X 2 is preferably a fluorine atom, a chlorine atom or a trifluoromethoxy group. Further, n is preferably an integer of 0-2. Specific examples of the compound (3A ′) include those described in the examples. Since the compound (3A ′) has a relatively large T c (phase transition temperature), when this compound is added to the liquid crystal composition, the clearing point (N−I) of the liquid crystal composition is raised. effective. That is, it is an effective material for expanding the driving temperature range.
【００２７】さらに、化合物（３Ａ’）は、Ｚ3 および
Ｚ4 が単結合であり、Ａ3 が非置換のトランス−１，４
−シクロヘキシレン基であり、ｎが０であり、Ｘ2 がフ
ッ素原子である化合物（３Ａ”）が液晶としての物性等
の点から特に好ましい。ただし、化合物（３Ａ”）にお
いて、Ｒ1 、Ｂ、Ｘ1 、Ｐｈ、およびｎは前記と同じ意
味を示し、Ｃｙはトランス−１，４−シクロヘキシレン
基を示す。Further, in the compound (3A ′), Z 3 and Z 4 are single bonds and A 3 is unsubstituted trans-1,4.
A compound (3A ″) which is a cyclohexylene group, n is 0, and X 2 is a fluorine atom is particularly preferable from the viewpoint of physical properties as a liquid crystal, etc. However, in the compound (3A ″), R 1 , B , X 1 , Ph, and n have the same meanings as described above, and Cy represents a trans-1,4-cyclohexylene group.
【００２８】[0028]
【化１１】R1-B-Ph-Cy-CX1=CF2（３Ａ”）[Chemical Formula 11] R 1 -B-Ph-Cy-CX 1 = CF 2 (3A ″)
【００２９】[0029]
【化１２】 [Chemical 12]
【００３０】化合物（３Ａ”）において、Ｒ1 は、低級
のアルキル基が好ましく、Ｘ1 は水素原子またはフッ素
原子が好ましい。In the compound (3A ″), R 1 is preferably a lower alkyl group, and X 1 is preferably a hydrogen atom or a fluorine atom.
【００３１】また、一般式（１）で表される化合物のう
ち、環構造を４個有する化合物、すなわちｋ、ｐ、およ
びｍが、いずれも１である場合の化合物の具体例として
は、実施例中の化合物が挙げられるがこれらに限定され
ない。Further, among the compounds represented by the general formula (1), compounds having four ring structures, that is, compounds in which k, p, and m are all 1 are Examples include, but are not limited to, the compounds.
【００３２】本発明のジオキサボリナン化合物は、以下
の方法に従って合成するのが好ましい。なお、下式にお
いて、Ｒ1 、Ａ1 、Ａ2 、Ａ3 、Ｂ、Ｚ1 、Ｚ2 、Ｚ
3 、Ｚ4 、Ｘ1 、Ｘ2 、ｋ、ｐ、ｍ、およびｎは前記と
同じ意味を示し、好ましい態様も同じである。また、Ｒ
2 およびＲ3 は、それぞれ、独立して１価の炭化水素基
を示し、炭素数１〜６程度の低級アルキル基が好まし
く、特にエチル基が好ましい。The dioxaborinane compound of the present invention is preferably synthesized according to the following method. In the following formula, R 1 , A 1 , A 2 , A 3 , B, Z 1 , Z 2 , Z
3 , Z 4 , X 1 , X 2 , k, p, m, and n have the same meanings as described above, and the preferred embodiments are also the same. Also, R
2 and R 3 each independently represent a monovalent hydrocarbon group, preferably a lower alkyl group having about 1 to 6 carbon atoms, and particularly preferably an ethyl group.
【００３３】[0033]
【化１３】 [Chemical 13]
【００３４】すなわち、まず２−置換マロン酸ジエチル
（４）を還元して、２−置換−１，３−プロパンジオー
ル（５）を合成する。一方、有機ハロゲン化物（６）と
金属マグネシウムから合成したグリニャール試薬を、ホ
ウ酸トリメチルと反応させて酸で処理し、ボロン酸
（７）を合成する。つぎに、上記で合成した２−置換−
１，３−プロパンジオール（５）とボロン酸（７）とを
反応させることにより、本発明のジオキサボリナン化合
物（１）を合成できる。That is, first, 2-substituted diethyl malonate (4) is reduced to synthesize 2-substituted-1,3-propanediol (5). On the other hand, a Grignard reagent synthesized from an organic halide (6) and metallic magnesium is reacted with trimethyl borate and treated with an acid to synthesize a boronic acid (7). Next, the 2-substituted-synthesized above
The dioxaborinane compound (1) of the present invention can be synthesized by reacting 1,3-propanediol (5) with a boronic acid (7).
【００３５】２−置換マロン酸ジエチル（４）は、Org.
Synth.,I,250(1961),R.Adamsに記載されるアルキルハラ
イドとマロン酸ジエチルとの反応で容易に合成できる。
上記の２−置換マロン酸ジエチル（４）は、いずれも公
知の化合物である。2-Substituted diethyl malonate (4) was prepared from Org.
It can be easily synthesized by a reaction between an alkyl halide described in Synth., I, 250 (1961), R. Adams and diethyl malonate.
The above-mentioned 2-substituted diethyl malonates (4) are all known compounds.
【００３６】２−置換マロン酸ジエチル（４）を還元す
る反応は、水素化リチウムアルミニウムを用いて実施す
るのが好ましい。該反応において、水素化リチウムアル
ミニウムの量は、２−置換マロン酸ジエチル（４）の１
当量に対して、１．０〜１．５当量程度が好ましい。ま
た還元反応においては、溶媒を存在させるのが好まし
い。溶媒としては、エーテル類が好ましく、特に、無水
テトラヒドロフラン（以下、無水ＴＨＦと記す。）が好
ましい。溶媒の量は、２−置換マロン酸ジエチル（４）
の１重量部に対して、１〜５重量部程度が好ましい。ま
た、還元反応の温度は、通常の場合、１０〜４０℃程度
が好ましく、特に、２０〜３０℃程度が好ましく、反応
時間は、１〜１０時間程度が好ましく、特に５〜６時間
が好ましい。そして、２−置換マロン酸ジエチル（４）
の還元反応によって、対応する２−置換−１，３−プロ
パンジオール（５）が生成する。The reaction for reducing the 2-substituted diethyl malonate (4) is preferably carried out using lithium aluminum hydride. In the reaction, the amount of lithium aluminum hydride was 1% of 2-substituted diethyl malonate (4).
About 1.0 to 1.5 equivalents are preferable with respect to equivalents. In addition, in the reduction reaction, it is preferable that a solvent is present. As the solvent, ethers are preferable, and anhydrous tetrahydrofuran (hereinafter referred to as anhydrous THF) is particularly preferable. The amount of solvent was 2-substituted diethyl malonate (4)
1 to 5 parts by weight is preferable. In addition, the temperature of the reduction reaction is usually preferably 10 to 40 ° C., particularly preferably 20 to 30 ° C., and the reaction time is preferably 1 to 10 hours, particularly 5 to 6 hours. And 2-substituted diethyl malonate (4)
The corresponding 2-substituted-1,3-propanediol (5) is produced by the reduction reaction of.
【００３７】一方、有機ハロゲン化物（６）と金属マグ
ネシウムとの反応において、金属マグネシウムの量は、
有機ハロゲン化物（６）の１当量に対して、１〜１．５
当量程度が好ましい。また、該反応は、無水ＴＨＦの中
で実施するのが好ましい。無水ＴＨＦの量は、有機ハロ
ゲン化物（６）の１重量部に対して、２〜６重量部程度
が好ましい。有機ハロゲン化物（６）と金属マグネシウ
ムとの反応温度は、通常の場合、２０〜３０℃程度が好
ましく、反応時間は、２〜３時間程度が好ましい。On the other hand, in the reaction of the organic halide (6) with metallic magnesium, the amount of metallic magnesium is
1 to 1.5 for 1 equivalent of the organic halide (6)
An equivalent amount is preferable. Also, the reaction is preferably carried out in anhydrous THF. The amount of anhydrous THF is preferably about 2 to 6 parts by weight with respect to 1 part by weight of the organic halide (6). Usually, the reaction temperature of the organic halide (6) and metallic magnesium is preferably about 20 to 30 ° C., and the reaction time is preferably about 2 to 3 hours.
【００３８】さらにグリニャール化合物は、ホウ酸トリ
メチルと反応させ、つぎに酸で処理し、ボロン酸（７）
を合成する。ホウ酸トリメチルの量は、グリニャール化
合物の１当量に対して、１〜１．５当量程度が好まし
い。また、グリニャール化合物は、ホウ酸トリメチルと
の反応温度は、通常の場合、−２０〜−１０℃程度が好
ましく、反応時間は、１〜２時間程度が好ましい。そし
て、反応液を室温で希釈塩酸で分解し、ボロン酸（７）
とする。Further, the Grignard compound was reacted with trimethyl borate and then treated with an acid to form a boronic acid (7).
To synthesize. The amount of trimethyl borate is preferably about 1 to 1.5 equivalents relative to 1 equivalent of the Grignard compound. In addition, the reaction temperature of the Grignard compound with trimethyl borate is usually preferably about -20 to -10 ° C, and the reaction time is preferably about 1 to 2 hours. Then, the reaction solution was decomposed with diluted hydrochloric acid at room temperature to give a boronic acid (7).
And
【００３９】最後に、上記で合成した２−置換−１，３
−プロパンジオール（５）とボロン酸（７）とを反応さ
せることにより、本発明のジオキサボリナン化合物を合
成する。２−置換−１，３−プロパンジオール（５）と
ボロン酸（７）との反応は、脱水縮合反応である。該反
応は、共沸脱水可能な不活性有機溶媒中で実施するのが
好ましい。共沸脱水可能な不活性有機溶媒としては、ベ
ンゼン、トルエン等が挙げられ、トルエンが好ましい。
該脱水縮合反応におけるボロン酸（７）の量は、２−置
換−１，３−プロパンジオール（５）の１当量に対し
て、０．５〜２当量程度が好ましい。また、共沸脱水可
能な不活性有機溶媒の量は、２−置換−１，３−プロパ
ンジオール（５）の１重量部に対して、５〜１５重量部
程度が好ましい。また、反応温度は、通常の場合、６０
〜１３０℃程度が好ましく、反応時間は、１〜２時間程
度が好ましい。Finally, the 2-substituted-1,3 synthesized above.
-The dioxaborinane compound of the present invention is synthesized by reacting propanediol (5) with boronic acid (7). The reaction between 2-substituted-1,3-propanediol (5) and boronic acid (7) is a dehydration condensation reaction. The reaction is preferably carried out in an azeotropically dehydratable inert organic solvent. Examples of the azeotropically dehydratable inert organic solvent include benzene and toluene, and toluene is preferable.
The amount of boronic acid (7) in the dehydration condensation reaction is preferably about 0.5 to 2 equivalents relative to 1 equivalent of 2-substituted-1,3-propanediol (5). The amount of the azeotropically dehydratable inert organic solvent is preferably about 5 to 15 parts by weight with respect to 1 part by weight of the 2-substituted-1,3-propanediol (5). The reaction temperature is usually 60.
The reaction time is preferably about 1 to 2 hours.
【００４０】本発明のジオキサボリナン化合物は、特に
液晶化合物として有用な化合物である。液晶化合物とし
て用いる場合には、本発明のジオキサボリナン化合物の
少なくとも１種あるいは２種以上を、他の化合物ととも
に液晶組成物として用いるのが好ましい。該液晶組成物
は、所望の液晶温度範囲を有する液晶組成物として使用
するものである。The dioxaborinane compound of the present invention is particularly useful as a liquid crystal compound. When used as a liquid crystal compound, it is preferable to use at least one kind or two or more kinds of the dioxaborinane compound of the present invention together with other compounds as a liquid crystal composition. The liquid crystal composition is used as a liquid crystal composition having a desired liquid crystal temperature range.
【００４１】液晶組成物とする場合の他の化合物として
は、通常の場合、液晶材料およびそれと類似の構造を有
する化合物を主成分として、必要に応じて含ませる添加
成分等が挙げられる。例えば、低粘性成分、誘電異方性
を向上させる成分、他の高温で液晶性を示す成分、コレ
ステリック性を付与する成分、２色性を示す成分、導電
性を付与する成分、その他各種添加剤等が挙げられる。
該他の化合物は、用途、要求性能等により異なり、特に
限定されない。As the other compound in the case of the liquid crystal composition, in the usual case, an additive component which contains a liquid crystal material and a compound having a similar structure to the main component as necessary, and the like can be mentioned. For example, a low-viscosity component, a component that improves dielectric anisotropy, another component that exhibits liquid crystallinity at high temperature, a component that imparts cholesteric properties, a component that exhibits dichroism, a component that imparts electrical conductivity, and various other additives. Etc.
The other compound differs depending on the use, required performance, etc. and is not particularly limited.
【００４２】液晶組成物とする場合、本発明のジオキサ
ボリナン化合物は、液晶組成物の１００重量部中に０．
１〜５０重量％、好ましくは３〜３０重量％を含ませる
のが好ましい。液晶組成物中に、本発明のジオキサボリ
ナン化合物を含ませることにより、液晶表示素子のマル
チプレックス駆動特性を向上させ、焼き付き現象を抑制
することができる。また、本発明のジオキサボリナン化
合物は、化学的にも安定な材料であるため、他の液晶化
合物等とともに用いた場合にも、不都合が生じない利点
がある。In the case of forming a liquid crystal composition, the dioxaborinane compound of the present invention is added in an amount of 0.
It is preferable to contain 1 to 50% by weight, preferably 3 to 30% by weight. By including the dioxaborinane compound of the present invention in the liquid crystal composition, the multiplex drive characteristics of the liquid crystal display device can be improved and the burn-in phenomenon can be suppressed. Further, since the dioxaborinane compound of the present invention is a chemically stable material, it has an advantage that no inconvenience occurs even when it is used together with other liquid crystal compounds and the like.
【００４３】液晶組成物に含ませる他の化合物として
は、以下の例が挙げられる。なお、下式においてＲ2 お
よびＲ3 は、同一であっても異なっていてもよく、それ
ぞれ、アルキル基、アルコキシ基、ハロゲン原子、シア
ノ基等の基を示し、Ｐｈは１，４−フェニレン基を示
し、Ｃｙはトランス−１，４−シクロヘキシレン基を示
す。また、１，４−フェニレン基およびトランス−１，
４−シクロヘキシレン基は、末端部分の水素原子が、ハ
ロゲン原子、シアノ基、メチル基等へ置換されていても
よく、また、１，４−フェニレン基およびトランス−
１，４−シクロヘキシレン基は他の６員環または５員環
に置換されていてもよい。該他の６員環または５員環と
しては、ピリミジン環、ジオキサン環等が挙げられる。
また、環と環の間の結合は、他の２価の有機結合基とな
っていてもよい。これらの置換は、液晶組成物としての
要求性能に合わせて適宜変更すればよい。Examples of the other compounds contained in the liquid crystal composition include the following. In the formula below, R 2 and R 3 may be the same or different and each represents a group such as an alkyl group, an alkoxy group, a halogen atom or a cyano group, and Ph is a 1,4-phenylene group. And Cy represents a trans-1,4-cyclohexylene group. In addition, 1,4-phenylene group and trans-1,
In the 4-cyclohexylene group, the hydrogen atom at the terminal part may be substituted with a halogen atom, a cyano group, a methyl group or the like, and a 1,4-phenylene group and trans-
The 1,4-cyclohexylene group may be substituted with another 6-membered ring or 5-membered ring. Examples of the other 6-membered ring or 5-membered ring include a pyrimidine ring and a dioxane ring.
The bond between the rings may be another divalent organic bonding group. These substitutions may be appropriately changed according to the required performance of the liquid crystal composition.
【００４４】[0044]
【化１４】Ｒ２−Ｃｙ−Ｃｙ−Ｒ３ Ｒ２−Ｃｙ−Ｐｈ−Ｒ３ Ｒ２−Ｐｈ−Ｐｈ−Ｒ３ Ｒ２−Ｃｙ−ＣＯＯ−Ｐｈ−Ｒ３ Ｒ２−Ｐｈ−ＣＯＯ−Ｐｈ−Ｒ３ Ｒ２−Ｃｙ−ＣＨ＝ＣＨ−Ｐｈ−Ｒ３ Ｒ２−Ｐｈ−ＣＨ＝ＣＨ−Ｐｈ−Ｒ３ Ｒ２−Ｃｙ−ＣＨ２ＣＨ２−Ｐｈ−Ｒ３ Ｒ２−Ｐｈ−ＣＨ２ＣＨ２−Ｐｈ−Ｒ３ Ｒ２−Ｐｈ−Ｎ＝Ｎ−Ｐｈ−Ｒ３ Ｒ２−Ｐｈ−ＮＯＮ−Ｐｈ−Ｒ３ Ｒ２−Ｃｙ−ＣＯＳ−Ｐｈ−Ｒ３ Embedded image R 2 -Cy-Cy-R 3 R 2 -Cy-Ph-R 3 R 2 -Ph-Ph-R 3 R 2 -Cy-COO-Ph-R 3 R 2 -Ph-COO-Ph -R 3 R 2 -Cy-CH = CH-Ph-R 3 R 2 -Ph-CH = CH-Ph-R 3 R 2 -Cy-CH 2 CH 2 -Ph-R 3 R 2 -Ph-CH 2 CH 2 -Ph-R 3 R 2 -Ph-N = N-Ph-R 3 R 2 -Ph-NON-Ph-R 3 R 2 -Cy-COS-Ph-R 3
【００４５】[0045]
【化１５】Ｒ２−Ｃｙ−Ｐｈ−Ｐｈ−Ｒ３ Ｒ２−Ｃｙ−Ｐｈ−Ｐｈ−Ｃｙ−Ｒ３ Ｒ２−Ｐｈ−Ｐｈ−Ｐｈ−Ｒ３ Ｒ２−Ｃｙ−ＣＯＯ−Ｐｈ−Ｐｈ−Ｒ３ Ｒ２−Ｃｙ−Ｐｈ−ＣＯＯ−Ｐｈ−Ｒ３ Ｒ２−Ｃｙ−ＣＯＯ−Ｐｈ−ＣＯＯ−Ｐｈ−Ｒ３ Ｒ２−Ｐｈ−ＣＯＯ−Ｐｈ−ＣＯＯ−Ｐｈ−Ｒ３ Ｒ２−Ｐｈ−ＣＯＯ−Ｐｈ−ＯＣＯ−Ｐｈ−Ｒ３ Embedded image R 2 -Cy-Ph-Ph-R 3 R 2 -Cy-Ph-Ph-Cy-R 3 R 2 -Ph-Ph-Ph-R 3 R 2 -Cy-COO-Ph-Ph- R 3 R 2 -Cy-Ph- COO-Ph-R 3 R 2 -Cy-COO-Ph-COO-Ph-R 3 R 2 -Ph-COO-Ph-COO-Ph-R 3 R 2 -Ph- COO-Ph-OCO-Ph-R 3
【００４６】ジオキサボリナン化合物を含む液晶組成物
は、注入等の方法で空の液晶セルに挿入され、さらに電
極付の基板間に挟持されて液晶電気光学素子とされる。
該液晶電気光学素子は、ＴＮ方式、ゲスト・ホスト方
式、動的散乱方式、フェーズチェンジ方式、ＤＡＰ方
式、二周波駆動方式、強誘電性液晶表示方式等種々のモ
ードで使用できる。The liquid crystal composition containing the dioxaborinane compound is inserted into an empty liquid crystal cell by a method such as injection, and then sandwiched between substrates with electrodes to form a liquid crystal electro-optical element.
The liquid crystal electro-optical element can be used in various modes such as a TN system, a guest-host system, a dynamic scattering system, a phase change system, a DAP system, a dual frequency drive system and a ferroelectric liquid crystal display system.
【００４７】液晶セルとしては、ＴＮ型液晶電気光学素
子がある。なお、ここで液晶電気光学素子と表現してい
るのは、表示用途以外の用途、例えば、調光窓、光シャ
ッター、偏光変換素子等にも使用できることを意味して
いる。As the liquid crystal cell, there is a TN type liquid crystal electro-optical element. The expression "liquid crystal electro-optical element" here means that it can be used for applications other than display applications, for example, light control windows, optical shutters, polarization conversion elements, and the like.
【００４８】液晶セルは、通常の場合、プラスチック、
ガラス等の基板上に、必要に応じてSiO2、Al2O3 等のア
ンダーコート層やカラーフィルター層を形成し、In2O3-
SnO2（ＩＴＯ）、SnO2等の電極を設け、パターニングし
た後、必要に応じてポリイミド、ポリアミド、SiO2、Al
2O3 等のオーバーコート層を形成し、配向処理し、これ
にシール材を印刷し、電極面が相対向するように配して
周辺をシールし、シール材を硬化して空の液晶セルを形
成する。The liquid crystal cell is usually made of plastic,
If necessary, an undercoat layer such as SiO 2 or Al 2 O 3 or a color filter layer may be formed on a substrate such as glass, and In 2 O 3-
After providing electrodes such as SnO 2 (ITO) and SnO 2 and patterning, if necessary, polyimide, polyamide, SiO 2 , Al
Form an overcoat layer of 2 O 3 etc., orient it, print a sealing material on it, and arrange it so that the electrode surfaces face each other to seal the periphery, and cure the sealing material to create an empty liquid crystal cell. To form.
【００４９】この空の液晶セルに、ジオキサボリナン化
合物を含む組成物を注入し、注入口を封止剤で封止して
液晶セルを構成する。さらに液晶セルに、偏光板、カラ
ー偏光板、光源、カラーフィルター、半透過反射板、反
射板、導光板、紫外線カットフィルター等を積層、文
字、図形等を印刷、ノングレア加工する等の処理を必要
に応じての実施して液晶電気光学素子が形成される。A composition containing a dioxaborinane compound is injected into this empty liquid crystal cell, and the injection port is sealed with a sealant to form a liquid crystal cell. Furthermore, processing such as laminating a polarizing plate, a color polarizing plate, a light source, a color filter, a semi-transmissive reflection plate, a reflection plate, a light guide plate, an ultraviolet ray cut filter, etc. on the liquid crystal cell, printing characters, figures, etc., non-glare processing etc. is required Then, the liquid crystal electro-optical element is formed.
【００５０】なお、上述の説明は、液晶電気光学素子の
基本的な構成および製法であり、例えば２層電極を用い
た基板、２層の液晶層を形成した２層液晶セル、ＴＦ
Ｔ、ＭＩＭ等の能動素子を形成したアクティブマトリク
ス基板を用いたアクティブマトリクス素子等、種々の構
成の液晶電気光学素子が採用される。The above description is of the basic structure and manufacturing method of the liquid crystal electro-optical element. For example, a substrate using a two-layer electrode, a two-layer liquid crystal cell in which two liquid crystal layers are formed, and a TF.
Liquid crystal electro-optical elements having various configurations such as an active matrix element using an active matrix substrate on which active elements such as T and MIM are formed are adopted.
【００５１】また、その他の液晶電気光学素子として
は、高ツイスト角のスーパーツイストネマチック（ＳＴ
Ｎ）型液晶電気光学素子や、多色性色素を用いたゲスト
−ホスト（ＧＨ）型液晶電気光学素子、強誘電性液晶電
気光学素子等も挙げられる。また、書き込みを熱によっ
て行う型の素子にも用いることもできる。As another liquid crystal electro-optical element, a super twist nematic (ST) having a high twist angle is used.
An N) type liquid crystal electro-optical element, a guest-host (GH) type liquid crystal electro-optical element using a polychromatic dye, a ferroelectric liquid crystal electro-optical element, and the like are also included. It can also be used for an element of the type in which writing is performed by heat.
【００５２】[0052]
【実施例】以下に、本発明を実施例を挙げて具体的に説
明するが、これらによって、本発明は限定されない。EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto.
【００５３】［合成例１］ジオキサボリナン化合物の合
成 撹拌器、温度計、滴下漏斗および還流冷却器を備えた20
00ccの４ツ口フラスコを窒素置換し、水素化リチウムア
ルミニウム49.7g(1.31モル）と無水ＴＨＦ650cc を仕込
み、激しく撹拌して懸濁させた液中に2-プロピルマロン
酸エチル（１１）154.49g(0.764 モル) を無水ＴＨＦ15
0cc に溶解した溶液を、室温にて滴下した。[Synthesis Example 1] Synthesis of dioxaborinane compound 20 equipped with a stirrer, thermometer, dropping funnel and reflux condenser
A 00 cc 4-necked flask was replaced with nitrogen, charged with lithium aluminum hydride (49.7 g, 1.31 mol) and anhydrous THF (650 cc), and stirred vigorously with stirring to suspend ethyl 2-propylmalonate (11) 154.49 g ( 0.764 mol) in anhydrous THF15
The solution dissolved in 0 cc was added dropwise at room temperature.
【００５４】室温で一晩撹拌後、氷水で冷却しながら水
酸化ナトリウム3gを水190cc 、テトラヒドロフラン600c
c に溶解した溶液を滴下して過剰の水素化リチウムアル
ミニウムを分解した。生成した白色の固形物をろ別し、
母液を濃縮後、残留物を減圧下で蒸留して２−プロピル
−１，３−プロパンジオール（１２）43.9g （収率50
％）を得た。After stirring overnight at room temperature, while cooling with ice water, sodium hydroxide 3 g was added to water 190 cc and tetrahydrofuran 600 c.
A solution dissolved in c was added dropwise to decompose excess lithium aluminum hydride. The white solid substance produced is filtered off,
After concentrating the mother liquor, the residue was distilled under reduced pressure to yield 43.9 g of 2-propyl-1,3-propanediol (12) (yield 50
%) Was obtained.
【００５５】式（１３）で表される化合物から、式（１
４）で表されるグリニャール試薬を合成した。つぎに、
撹拌器、温度計、滴下漏斗および還流冷却器を備えた20
0ccの四ツ口フラスコを窒素置換し、ホウ酸トリメチル
（１５）8.90g(0.086 モル)と無水ＴＨＦ13ccを仕込
み、撹拌して溶液とし、ドライアイス槽にて内温を−20
℃に保った。式（１４）で表されるグリニャール試薬39
ミリモルを含むテトラヒドロフラン溶液30ccを撹拌しな
がら滴下し、無水ＴＨＦ50ccを追加し、−20℃で２時間
撹拌した後、５％希塩酸22ccを滴下しながら、温度を室
温にまで上げ反応を終了した。目的物を水層よりトルエ
ンで溶媒抽出し、有機層を分取して減圧下溶媒留去し
た。折出した固形物を水とトルエンで洗浄し、４−
［４’−（２，２’−ジフルオロビニル）シクロヘキシ
ル］フェニルボロン酸（１６）の3.56g （収率34％）を
得た。From the compound represented by the formula (13), the compound represented by the formula (1)
The Grignard reagent represented by 4) was synthesized. Next,
20 with stirrer, thermometer, dropping funnel and reflux condenser
The 0 cc four-necked flask was replaced with nitrogen, and trimethyl borate (15) 8.90 g (0.086 mol) and anhydrous THF 13 cc were charged, and the solution was stirred to prepare an internal temperature of -20 in a dry ice bath.
It was kept at ℃. Grignard reagent represented by the formula (14) 39
30 ml of a tetrahydrofuran solution containing millimole was added dropwise with stirring, 50 cc of anhydrous THF was added, the mixture was stirred at -20 ° C for 2 hours, and then 22 cc of 5% dilute hydrochloric acid was added dropwise to raise the temperature to room temperature to complete the reaction. The target product was subjected to solvent extraction from the aqueous layer with toluene, the organic layer was separated, and the solvent was evaporated under reduced pressure. The separated solid matter was washed with water and toluene, and 4-
3.56 g (yield 34%) of [4 ′-(2,2′-difluorovinyl) cyclohexyl] phenylboronic acid (16) was obtained.
【００５６】つぎに還流冷却器付き共沸脱水器を備えた
50ccのナスフラスコに、先に合成した２−プロピル−
１，３−プロパンジオール（１２）0.0063モルと４−
［４’−（２，２’−ジフルオロビニル）シクロヘキシ
ル］フェニルボロン酸（１６）0.0052モルをトルエン20
ccと共に加え還流温度で共沸脱水を行った。１時間で反
応を完了し、不溶解分を濾別して、トルエンを減圧下留
去し、メタノール、トルエンから再結晶し、ヘキサンを
展開溶媒としたシリカゲルカラムでカラム精製を行い、
イソプロピルアルコールで再結晶して式（１７）で表さ
れる化合物の1.01g（収率55％）を得た（融点＝96.9
℃）。Next, an azeotropic dehydrator equipped with a reflux condenser was provided.
In a 50 cc eggplant flask, add 2-propyl-
0.003 mol of 1,3-propanediol (12) and 4-
0.0052 mol of [4 '-(2,2'-difluorovinyl) cyclohexyl] phenylboronic acid (16) was added to toluene 20
It was added together with cc to carry out azeotropic dehydration at the reflux temperature. The reaction was completed in 1 hour, the insoluble matter was filtered off, the toluene was distilled off under reduced pressure, recrystallized from methanol and toluene, and column purification was performed with a silica gel column using hexane as a developing solvent.
Recrystallization from isopropyl alcohol gave 1.01 g (yield 55%) of the compound represented by the formula (17) (melting point = 96.9).
° C).
【００５７】[0057]
【化１６】 Embedded image
【００５８】式（１７）で表される化合物のＩＲスペク
トルを図１に表す。The IR spectrum of the compound represented by the formula (17) is shown in FIG.
【００５９】［合成例２］一般式（２Ａ’）で表される
化合物に属する合成例[Synthesis example 2] Synthesis example belonging to the compound represented by formula (2A ')
【００６０】[0060]
【化１７】R1-B-Ph-Z4-(CH2)n-CX1=CFX2 （２Ａ’）Embedded image R 1 -B-Ph-Z 4 - (CH 2) n -CX 1 = CFX 2 (2A ')
【００６１】合成例１の化合物（１１）の代わりに、合
成例２と同様の２−プロピル部分の異なる２−置換マロ
ン酸ジエチル（１９）を用い、化合物（１３）の代わり
に、式（２０）で表される化合物をそれぞれ用いて、合
成例１と同様に反応を実施し、下式で表される化合物を
合成した。ただし、以下の化合物において、Ｒ1 、Ａ
1 、Ａ2 、Ａ3 、Ｂ、Ｚ1 、Ｚ2 、Ｚ3 、Ｚ4 、Ｘ1 、
Ｘ2 、ｋ、ｐ、ｍ、ｎ、Ｐｈ、およびＣｙは、前記と同
じ意味を示す。Instead of the compound (11) of Synthesis Example 1, a 2-substituted diethyl malonate (19) having a different 2-propyl moiety as in Synthesis Example 2 was used, and instead of the compound (13), a compound of the formula (20) was used. ) Was used to carry out a reaction in the same manner as in Synthesis Example 1 to synthesize a compound represented by the following formula. However, in the following compounds, R 1 , A
1 , A 2 , A 3 , B, Z 1 , Z 2 , Z 3 , Z 4 , X 1 ,
X 2 , k, p, m, n, Ph, and Cy have the same meanings as described above.
【００６２】[0062]
【化１８】R1-CH(COOC2H5)2 （１９） Cl-Ph-Z4-(CH2)n-CX1=CFX2（２０）Embedded image R 1 -CH (COOC 2 H 5 ) 2 (19) Cl-Ph-Z 4 - (CH 2) n -CX 1 = CFX 2 (20)
【００６３】[0063]
【化１９】 (2A'-1) n-C3H7-B-Ph-CH2CH2-CF=CF2 MS m/e 312(M+) (2A'-2) n-C5H11-B-Ph-CH2CH2-CH=CFCl (2A'-3) n-C2H5OCH2-B-Ph-CH2CH2-CF=CF2 MS m/e 328(M+) (2A'-4) n-C6H13OCH2-B-Ph-CH2CH2-CF=CFC2H (2A'-5) CH2=CHCH2-B-Ph-CH2CH2-CF=CF2 (2A'-6) n-C2H5-B-Ph-COO-CH2CH2-CCl=CF2 (2A'-7) n-C5H11-B-Ph-COO-CH2CH2-CF=CF2 (2A'-8) n-C8H17-B-Ph-COO-CH2CH2-CF=CF2 (2A'-9) n-C3H7OCH2-B-Ph-COO-CH2CH2-CF=CF2 (2A'-10) n-C6H13OCH2-B-Ph-COO-CH2CH2-CF=CF2 (2A'-11) CH2=CHCH2-B-Ph-COO-CH2CH2-CF=CF2 (2A'-12) n-C3H7-CH=CHCH2-B-Ph-CH2O-CF=CF2 Embedded image (2A′-1) nC 3 H 7 -B-Ph-CH 2 CH 2 -CF = CF 2 MS m / e 312 (M + ) (2A'-2) nC 5 H 11 -B- Ph-CH 2 CH 2 -CH = CFCl (2A'-3) nC 2 H 5 OCH 2 -B-Ph-CH 2 CH 2 -CF = CF 2 MS m / e 328 (M + ) (2A'-4 ) nC 6 H 13 OCH 2 -B-Ph-CH 2 CH 2 -CF = CFC 2 H (2A'-5) CH 2 = CHCH 2 -B-Ph-CH 2 CH 2 -CF = CF 2 (2A ' -6) nC 2 H 5 -B-Ph-COO-CH 2 CH 2 -CCl = CF 2 (2A'-7) nC 5 H 11 -B-Ph-COO-CH 2 CH 2 -CF = CF 2 ( 2A'-8) nC 8 H 17 -B-Ph-COO-CH 2 CH 2 -CF = CF 2 (2A'-9) nC 3 H 7 OCH 2 -B-Ph-COO-CH 2 CH 2 -CF = CF 2 (2A'-10) nC 6 H 13 OCH 2 -B-Ph-COO-CH 2 CH 2 -CF = CF 2 (2A'-11) CH 2 = CHCH 2 -B-Ph-COO-CH 2 CH 2 -CF = CF 2 (2A'-12) nC 3 H 7 -CH = CHCH 2 -B-Ph-CH 2 O-CF = CF 2
【００６４】［合成例３］合成例２以外の化合物（２
Ａ）で表される化合物に属する合成例[Synthesis Example 3] Compounds (2
Synthesis example belonging to the compound represented by A)
【００６５】[0065]
【化２０】R1-B-(Z2-A2)-Z4-(CH2)n-CX1=CFX2 （２Ａ）Embedded image R 1 -B- (Z 2 -A 2 ) -Z 4 - (CH 2) n -CX 1 = CFX 2 (2A)
【００６６】合成例１の２−プロピルマロン酸ジエチル
（１１）の代わりに、合成例２と同様の２−プロピル部
分の異なる化合物（１９）を用い、化合物（１３）の代
わりに、化合物（２１）で表される化合物をそれぞれ用
いて、合成例１と同様に反応を実施し、下式で表される
化合物を合成した。Instead of diethyl 2-propylmalonate (11) in Synthesis Example 1, the same compound (19) having a different 2-propyl moiety as in Synthesis Example 2 was used, and instead of compound (13), compound (21) was used. ) Was used to carry out a reaction in the same manner as in Synthesis Example 1 to synthesize a compound represented by the following formula.
【００６７】[0067]
【化２１】R1-CH(COOC2H5)2 （１９） Cl-(Z2-Ph)-Z4-(CH2)n-CX1=CFX2 （２１）Embedded image R 1 -CH (COOC 2 H 5 ) 2 (19) Cl- (Z 2 -Ph) -Z 4 - (CH 2) n -CX 1 = CFX 2 (21)
【００６８】[0068]
【化２２】 (2A-1) n-C3H7OCH2-B-OCH2-Ph-CH2CH2-CCl=CF2 (2A-2) n-C6H13OCH2-B-OCH2-Ph-CH2CH2-CF=CF2 (2A-3) CH2=CHCH2-B-OCH2-Ph-CH2CH2-CF=CF2 (2A-4) n-C3H7-CH=CHCH2-B-OCH2-Ph-CH2CH2-CF=CFOCF3 (2A-5) C3H7OCH2-B-OCH2-Ph-CH2CH2-CF=CF2 (2A-6) CH2=CHCH2-B-OCH2-Ph-CH2CH2-CF=CFOCF3 (2A-7) n-C6H13OCH2-B-COO-Ph-CH2CH2-CF=CF2 (2A-8) n-C3H7-CH=CHCH2-B-OCH2-Ph-COO-CH2CH2-CCl=CF2 (2A-9) C3H7OCH2-B-OCH2-Ph-COO-CH2CH2-CF=CF2 (2A-10) CH2=CHCH2-B-OCH2-Ph-COO-CH2CH2-CF=CF2 (2A-11) n-C2H5-B-OCH2-Ph-COO-CH2CH2-CF=CF2 (2A-12) n-C5H11-B-OCH2-Ph-COO-CH2CH2-CF=CFOCF3 (2A-13) n-C8H17-B-OCH2-Ph-COO-CH2CH2-CF=CF2 (2A-14) n-C3H7-CH=CHCH2-B-OCO-Ph-CH=CH-CH2CH2-CF=CF2 (2A-15) n-C8H17-B-COO-Ph-COO-CH2CH2-CF=CF2 (2A-16) CH2=CHCH2-B-OCO-Ph-CH2O-CF=CF2 (2A-17) C3H7OCH2-B-OCO-Ph-C ≡C-CF=CF2 (2A-18) CH2=CHCH2-B-OCO-Ph-C≡Ｃ−ＣＨ２−ＣＦ＝ＣＦ２ (2A-1) nC 3 H 7 OCH 2 -B-OCH 2 -Ph-CH 2 CH 2 -CCl = CF 2 (2A-2) nC 6 H 13 OCH 2 -B-OCH 2 -Ph -CH 2 CH 2 -CF = CF 2 (2A-3) CH 2 = CHCH 2 -B-OCH 2 -Ph-CH 2 CH 2 -CF = CF 2 (2A-4) nC 3 H 7 -CH = CHCH 2 -B-OCH 2 -Ph-CH 2 CH 2 -CF = CFOCF 3 (2A-5) C 3 H 7 OCH 2 -B-OCH 2 -Ph-CH 2 CH 2 -CF = CF 2 (2A-6 ) CH 2 = CHCH 2 -B-OCH 2 -Ph-CH 2 CH 2 -CF = CFOCF 3 (2A-7) nC 6 H 13 OCH 2 -B-COO-Ph-CH 2 CH 2 -CF = CF 2 (2A-8) nC 3 H 7 -CH = CHCH 2 -B-OCH 2 -Ph-COO-CH 2 CH 2 -CCl = CF 2 (2A-9) C 3 H 7 OCH 2 -B-OCH 2- Ph-COO-CH 2 CH 2 -CF = CF 2 (2A-10) CH 2 = CHCH 2 -B-OCH 2 -Ph-COO-CH 2 CH 2 -CF = CF 2 (2A-11) nC 2 H 5 -B-OCH 2 -Ph-COO-CH 2 CH 2 -CF = CF 2 (2A-12) nC 5 H 11 -B-OCH 2 -Ph-COO-CH 2 CH 2 -CF = CFOCF 3 (2A -13) nC 8 H 17 -B-OCH 2 -Ph-COO-CH 2 CH 2 -CF = CF 2 (2A-14) nC 3 H 7 -CH = CHCH 2 -B-OCO-Ph-CH = CH -CH 2 CH 2 -CF = CF 2 (2A-15) nC 8 H 17 -B-COO-Ph-COO-CH 2 CH 2 -CF = CF 2 (2A-16) CH 2 = CHCH 2 -B- OCO-Ph-CH 2 O-CF = CF 2 (2A-17) C 3 H 7 OCH 2 -B-OCO-Ph-C ≡ C-CF = CF 2 (2A-18) CH 2 = CHCH 2 -B -OCO-Ph-C≡C-CH 2 -CF = CF 2
【００６９】化合物（２１）のＰｈがＣｙである化合物
を用いて、同様に反応を実施し、下式の化合物を得た。A similar reaction was carried out using a compound of Compound (21) in which Ph was Cy to obtain a compound of the following formula.
【００７０】[0070]
【化２３】 （２Ａ−１９） ｎ−Ｃ２Ｈ５−ＣＨ＝ＣＨＣＨ２−Ｂ
−Ｃｙ−ＣＨ２ＣＨ２−ＣＦ＝ＣＦ２ Embedded image (2A-19) nC 2 H 5 —CH═CHCH 2 —B
-Cy-CH 2 CH 2 -CF = CF 2
【００７１】［合成例４］一般式（３Ａ”）で表される
化合物に属する合成例[Synthesis example 4] Synthesis example belonging to the compound represented by formula (3A ")
【００７２】[0072]
【化２４】R1-B-Ph-Cy-CX1=CF2（３Ａ”）Embedded image R 1 -B-Ph-Cy-CX 1 = CF 2 (3A ″)
【００７３】合成例１の化合物（１１）の代わりに、合
成例２と同様の２−プロピル部分の異なる化合物（１
９）を用い、化合物（１３）の代わりに、化合物（２
２）をそれぞれ用いて、合成例１と同様に反応を実施
し、下式で表される化合物を合成した。Instead of the compound (11) of Synthesis Example 1, the same compound (1) having a different 2-propyl moiety as in Synthesis Example 2 was used.
9) was used instead of the compound (13).
2) was used to carry out a reaction in the same manner as in Synthesis Example 1 to synthesize a compound represented by the following formula.
【００７４】[0074]
【化２５】R6-CH(COOC2H5)2 （１９） Cl-Ph-Cy-CX1=CF2 （２２）Embedded image R 6 —CH (COOC 2 H 5 ) 2 (19) Cl-Ph-Cy-CX 1 = CF 2 (22)
【００７５】[0075]
【化２６】 (3A"-1) n-C2H5-B-Ph-Cy-CH=CF2 MS m/e 334(M+) (3A"-2) n-C5H11-B-Ph-Cy-CH=CF2 MS m/e 376(M+) (3A"-3) n-C8H17-B-Ph-Cy-CH=CF2 (3A"-4) n-C3H7OCH2-B-Ph-Cy-CH=CF2 (3A"-5) n-C5H11OCH2-B-Ph-Cy-CH=CF2 (3A"-6) CH2=CHCH2-B-Ph-Cy-CH=CF2 (3A"-7) n-C3H7-CH=CHCH2-B-Ph-Cy-CH=CF2 (3A"-8) n-C2H5-B-Ph-Cy-CF=CF2 (3A"-9) n-C5H11-B-Ph-Cy-CF=CF2 (3A"-10)n-C8H17-B-Ph-Cy-CF=CF2 (3A"-11)n-C3H7OCH2-B-Ph-Cy-CH=CF2 Embedded image (3A "-1) nC 2 H 5 -B-Ph-Cy-CH = CF 2 MS m / e 334 (M + ) (3A" -2) nC 5 H 11 -B-Ph-Cy -CH = CF 2 MS m / e 376 (M + ) (3A "-3) nC 8 H 17 -B-Ph-Cy-CH = CF 2 (3A" -4) nC 3 H 7 OCH 2 -B- Ph-Cy-CH = CF 2 (3A "-5) nC 5 H 11 OCH 2 -B-Ph-Cy-CH = CF 2 (3A" -6) CH 2 = CHCH 2 -B-Ph-Cy-CH = CF 2 (3A "-7) nC 3 H 7 -CH = CHCH 2 -B-Ph-Cy-CH = CF 2 (3A" -8) nC 2 H 5 -B-Ph-Cy-CF = CF 2 (3A "-9) nC 5 H 11 -B-Ph-Cy-CF = CF 2 (3A" -10) nC 8 H 17 -B-Ph-Cy-CF = CF 2 (3A "-11) nC 3 H 7 OCH 2 -B-Ph-Cy-CH = CF 2
【００７６】［合成例５］化合物（３Ａ”）以外の化合
物（３Ａ’）に属する合成例[Synthesis example 5] Synthesis example belonging to compound (3A ') other than compound (3A ")
【００７７】[0077]
【化２７】 R1-B-Ph-Z3-A3-Z4-(CH2)n-CX1=CFX2（３Ａ’）Embedded image R 1 -B-Ph-Z 3 -A 3 -Z 4 - (CH 2) n -CX 1 = CFX 2 (3A ')
【００７８】合成例１の化合物（１１）の代わりに、合
成例２と同様の２−プロピル部分の異なる化合物（１
９）を用い、化合物（１３）の代わりに、化合物（２
３）をそれぞれ用いて、合成例１と同様に反応を実施
し、下式で表される化合物を合成した。Instead of the compound (11) of Synthesis Example 1, the same compound (1) having a different 2-propyl moiety as in Synthesis Example 2 was used.
9) was used instead of the compound (13).
Using 3) respectively, a reaction was carried out in the same manner as in Synthesis Example 1 to synthesize a compound represented by the following formula.
【００７９】[0079]
【化２８】R1-CH(COOC2H5)2 （１９） Cl-Ph-Z3-A3-Z4-(CH2)n-CX1=CFX2（２３）Embedded image R 1 -CH (COOC 2 H 5 ) 2 (19) Cl-Ph-Z 3 -A 3 -Z 4 - (CH 2) n -CX 1 = CFX 2 (23)
【００８０】[0080]
【化２９】(3A'-1)n-C5H11OCH2-B-Ph-Cy-CF=CFOCF3 (3A'-2)CH2=CHCH2-B-Ph-Cy-CF=CFC2H5 Embedded image (3A'-1) nC 5 H 11 OCH 2 -B-Ph-Cy-CF = CFOCF 3 (3A'-2) CH 2 = CHCH 2 -B-Ph-Cy-CF = CFC 2 H Five
【００８１】［合成例６］化合物（３Ａ”）および化合
物（３Ａ’）以外の一般式（３Ａ）で表される化合物に
属する合成例[Synthesis Example 6] Synthesis examples belonging to compounds represented by the general formula (3A) other than the compound (3A ″) and the compound (3A ′)
【００８２】[0082]
【化３０】 R1-B-(Z2-A2)-(Z3-A3)-Z4-(CH2)n-CX1=CFX2 （３Ａ）Embedded image R 1 -B- (Z 2 -A 2 ) - (Z 3 -A 3) -Z 4 - (CH 2) n -CX 1 = CFX 2 (3A)
【００８３】合成例１の２−プロピルマロン酸ジエチル
（１１）の代わりに、合成例２と同様の２−プロピル部
分の異なる２−置換マロン酸ジエチル（１９）を用い、
式（１３）で表される化合物の代わりに、式（２４）で
表される化合物をそれぞれ用いて、合成例１と同様に反
応を実施し、下式で表される化合物を合成した。Instead of diethyl 2-propylmalonate (11) in Synthesis Example 1, 2-substituted diethyl malonate (19) having a different 2-propyl moiety as in Synthesis Example 2 was used.
Instead of the compound represented by the formula (13), a compound represented by the formula (24) was used, and a reaction was carried out in the same manner as in Synthesis Example 1 to synthesize a compound represented by the following formula.
【００８４】[0084]
【化３１】R1-CH(COOC2H5)2 （１９） Cl-(Z2-A2)-(Z3-A3)-Z4-(CH2)n-CX1=CFX2 （２４）Embedded image R 1 -CH (COOC 2 H 5 ) 2 (19) Cl- (Z 2 -A 2) - (Z 3 -A 3) -Z 4 - (CH 2) n -CX 1 = CFX 2 (24)
【００８５】[0085]
【化３２】 (3A-1)n-C3H7-B-OCH2-Ph-COO-Cy-CH2CH2-CF=CF2 (3A-2)n-C8H17-B-OCH2-Ph-COO-Cy-COO-CH2CH2-CF=CF2 (3A-3)n-C3H7OCH2-B-OCH2-Ph-CH2CH2-Cy-CH2CH2-CH=CFOCF3 (3A-4)n-C6H13OCH2-B-OCH2-Ph-CH2CH2-Cy-COO-CH2CH2-CF=CFCl (3A-5)CH2=CHCH2-B-OCO-Ph-Ph-COO-CH2CH2-CF=CF2 (3A-1) nC 3 H 7 -B-OCH 2 -Ph-COO-Cy-CH 2 CH 2 -CF = CF 2 (3A-2) nC 8 H 17 -B-OCH 2 -Ph -COO-Cy-COO-CH 2 CH 2 -CF = CF 2 (3A-3) nC 3 H 7 OCH 2 -B-OCH 2 -Ph-CH 2 CH 2 -Cy-CH 2 CH 2 -CH = CFOCF 3 (3A-4) nC 6 H 13 OCH 2 -B-OCH 2 -Ph-CH 2 CH 2 -Cy-COO-CH 2 CH 2 -CF = CFCl (3A-5) CH 2 = CHCH 2 -B- OCO-Ph-Ph-COO-CH 2 CH 2 -CF = CF 2
【００８６】［合成例６］一般式（３Ｂ）で表される化
合物に属する合成例[Synthesis example 6] Synthesis example belonging to the compound represented by formula (3B)
【００８７】[0087]
【化３３】 R-(A1-Z1)-B-(Z2-A2)-Z4-(CH2)n-CX1=CFX2（３Ｂ）Embedded image R- (A 1 -Z 1) -B- (Z 2 -A 2) -Z 4 - (CH 2) n -CX 1 = CFX 2 (3B)
【００８８】実施例１の２−プロピルマロン酸ジエチル
（１１）の代わりに、２−プロピル部分の異なる２−置
換マロン酸ジエチル（２５）を用い、式（１３）で表さ
れる化合物の代わりに、式（２６）で表される化合物を
それぞれ用いて、合成例１と同様に反応を実施し、下式
で表される化合物を合成した。Instead of diethyl 2-propylmalonate (11) of Example 1, 2-substituted diethyl malonate (25) having a different 2-propyl moiety was used, and instead of the compound represented by formula (13). Using each of the compounds represented by formula (26), a reaction was carried out in the same manner as in Synthesis Example 1 to synthesize a compound represented by the following formula.
【００８９】[0089]
【化３４】R-(A1-Z1)-CH(COOC2H5)2（２５） Cl-(Z2-A2)-Z4-(CH2)n-CX1=CFX2 （２６）Embedded image R- (A 1 -Z 1) -CH (COOC 2 H 5) 2 (25) Cl- (Z 2 -A 2) -Z 4 - (CH 2) n -CX 1 = CFX 2 ( 26)
【００９０】[0090]
【化３５】化合物（２５）のＡ1 がＣｙである場合に生
成する化合物。 (3B-1)n-C5H11-Cy-B-Ph-CH2O-CH=CF2 (3B-2)CH3-Cy-B-Ph-CH2O-CF=CF2 (3B-3)CH2=CHCH2-Cy-CH2O-B-Ph-CH2O-CF=CF2 (3B-4)CH3-Cy-B1-Cy-CH2CH2-CH=CFOCF3 (3B-5)n-C5H11-Cy-B-Cy-CH2CH2-CF=CFCl (3B-6)CH2=CHCH2-Cy-CH2O-B-Cy-CH2CH2-CF=CF2 (3B-7)C5H11-Cy-B-CH2CH2-Cy-CH2CH2-CF=CF2 (3B-8)CH2=CHCH2-Cy-CH2O-B-CH2CH2-Cy-CH2CH2-CF=CFCl (3B-9)C5H11-Cy-B-CH=CH-Cy-CH2CH2-CF=CF2 (3B-10)CH2=CHCH2-Cy-CH2O-B-C≡C-Cy-CH2CH2-CF=CFClEmbedded image A compound formed when A 1 of the compound (25) is Cy. (3B-1) nC 5 H 11 -Cy-B-Ph-CH 2 O-CH = CF 2 (3B-2) CH 3 -Cy-B-Ph-CH 2 O-CF = CF 2 (3B-3 ) CH 2 = CHCH 2 -Cy-CH 2 OB-Ph-CH 2 O-CF = CF 2 (3B-4) CH 3 -Cy-B 1 -Cy-CH 2 CH 2 -CH = CFOCF 3 (3B- 5) nC 5 H 11 -Cy-B-Cy-CH 2 CH 2 -CF = CFCl (3B-6) CH 2 = CHCH 2 -Cy-CH 2 OB-Cy-CH 2 CH 2 -CF = CF 2 ( 3B-7) C 5 H 11 -Cy-B-CH 2 CH 2 -Cy-CH 2 CH 2 -CF = CF 2 (3B-8) CH 2 = CHCH 2 -Cy-CH 2 OB-CH 2 CH 2 -Cy-CH 2 CH 2 -CF = CFCl (3B-9) C 5 H 11 -Cy-B-CH = CH-Cy-CH 2 CH 2 -CF = CF 2 (3B-10) CH 2 = CHCH 2 -Cy-CH 2 OBC ≡ C-Cy-CH 2 CH 2 -CF = CFCl
【００９１】[0091]
【化３６】化合物（２５）のＡ1 がＰｈである場合に生
成する化合物。 (3B-11)n-C2H5OCH2-Ph-B-Ph-CH2O-CF=CFCF3 (3B-12)n-C5H11OCH2-Ph-B-Ph-CH2O-CF=CFC2H5 (3B-13)n-C2H5OCH2-Ph-B-Cy-CH2CH2-CF=CF2 (3B-14)n-C5H11OCH2-Ph-B-Cy-CH2CH2-CF=CFC2H5 (3B-15)C5H11OCH2-Ph-B-CH2CH2-Cy-CH2CH2-CH=CF2 (3B-16)C5H11OCH2-Ph-B-C ≡C-Cy-CH2CH2-CH=CFOCF3 Embedded image The compound formed when A 1 of the compound (25) is Ph. (3B-11) nC 2 H 5 OCH 2 -Ph-B-Ph-CH 2 O-CF = CFCF 3 (3B-12) nC 5 H 11 OCH 2 -Ph-B-Ph-CH 2 O-CF = CFC 2 H 5 (3B-13) nC 2 H 5 OCH 2 -Ph-B-Cy-CH 2 CH 2 -CF = CF 2 (3B-14) nC 5 H 11 OCH 2 -Ph-B-Cy-CH 2 CH 2 -CF = CFC 2 H 5 (3B-15) C 5 H 11 OCH 2 -Ph-B-CH 2 CH 2 -Cy-CH 2 CH 2 -CH = CF 2 (3B-16) C 5 H 11 OCH 2 -Ph-BC ≡ C-Cy-CH 2 CH 2 -CH = CFOCF 3
【００９２】［合成例７］環構造を４個有するジオキサ
ボリナン化合物の合成[Synthesis Example 7] Synthesis of dioxaborinane compound having four ring structures
【００９３】[0093]
【化３７】R-(A1-Z1)-B-(Z2-A2)-(Z3-A3)-Z4-(CH2)n-CX
1=CFX2（３Ｂ）Embedded image R- (A 1 -Z 1) -B- (Z 2 -A 2) - (Z 3 -A 3) -Z 4 - (CH 2) n -CX
1 = CFX 2 (3B)
【００９４】合成例１の化合物（１１）の代わりに、２
−プロピル部分の異なる化合物（２５）を用い、式（１
３）で表される化合物の代わりに、化合物（２４）で表
される化合物をそれぞれ用いて、合成例１と同様に反応
を実施し、下式で表される化合物を合成した。Instead of the compound (11) of Synthesis Example 1, 2
A compound of the formula (1
A compound represented by the following formula was synthesized by carrying out a reaction in the same manner as in Synthesis Example 1 using the compound represented by the compound (24) instead of the compound represented by 3).
【００９５】[0095]
【化３８】R-(A1-Z1)-CH(COOC2H5)2（２５） Cl-(Z2-A2)-(Z3-A3)-Z4-(CH2)n-CX1=CFX2 （２４）Embedded image R- (A 1 -Z 1) -CH (COOC 2 H 5) 2 (25) Cl- (Z 2 -A 2) - (Z 3 -A 3) -Z 4 - (CH 2) n -CX 1 = CFX 2 (24)
【００９６】[0096]
【化３９】 (4-1) n-C5H11-Cy-B-Ph-Cy-CH=CF2 MS m/e 458(M+) (4-2) n-C2H5OCH2-Ph-B-Ph-Cy-CH=CF2 (4-3) n-C5H11OCH2-Ph-B-Ph-Cy-CH=CF2 (4-4) n-C2H5-Cy-B-Ph-Cy-CH=CF2 (4-5) CH2=CHCH2-Cy-CH2O-B-Ph-Cy-CH=CF2 (4-1) nC 5 H 11 -Cy-B-Ph-Cy-CH = CF 2 MS m / e 458 (M + ) (4-2) nC 2 H 5 OCH 2 -Ph-B -Ph-Cy-CH = CF 2 (4-3) nC 5 H 11 OCH 2 -Ph-B-Ph-Cy-CH = CF 2 (4-4) nC 2 H 5 -Cy-B-Ph-Cy -CH = CF 2 (4-5) CH 2 = CHCH 2 -Cy-CH 2 OB-Ph-Cy-CH = CF 2
【００９７】［ジオキサボリナン化合物の物性評価方
法］ＴＮセルのマルチプレックス駆動特性は、通常の場
合、駆動電圧、電圧マージン、応答速度等で表される
が、表示コントラストに直接影響する特性としては電圧
マージン（Ｍ）が最も重要である。[Method for evaluating physical properties of dioxaborinane compound] The multiplex drive characteristic of a TN cell is usually represented by a drive voltage, a voltage margin, a response speed, and the like. (M) is the most important.
【００９８】電圧マージン（Ｍ）とは駆動電圧の変動が
どの程度許容できるかを表す値であり、選択波形で充分
点灯するための最低電圧（ＶON）と半選択波形でクロス
トークが生じ始める最高電圧（ＶOFF ）との差の駆動電
圧に対する割合として次式のように定義される。The voltage margin (M) is a value indicating how much the fluctuation of the driving voltage is allowable, and crosstalk begins to occur between the minimum voltage (V ON ) for sufficiently lighting the selected waveform and the half-selected waveform. It is defined as the ratio of the difference from the maximum voltage (V OFF ) to the drive voltage as in the following equation.
【００９９】 Ｍ ＝（ＶOFF −ＶON）／ＶD × 100％ (a) ＶD ＝（ＶON＋ＶOFF ）／２
（ｂ）M = (V OFF −V ON ) / V D × 100% (a) V D = (V ON + V OFF ) / 2
(B)
【０１００】上式 (a)、 (b)において、ＶON、ＶOFF は
印加波形、視野角、温度あるいは点灯状態とクロストー
ク状態の定義等により意味が変わるため、本発明におい
ては常法に従い次のように定義した値を用いた。まず、
ＴＮセルは従来から知られているように印加電圧の実効
値に応じて作動するので、使用波形のデューティ比ある
いはバイアスが変化したとしてもＴＮセル間の相対比較
をする場合には、１種類の波形による比較で充分であ
る。In the above equations (a) and (b), V ON and V OFF have different meanings depending on the applied waveform, viewing angle, temperature, or the definition of the lighting state and the crosstalk state. The values defined as follows were used. First,
Since the TN cells operate according to the effective value of the applied voltage as is conventionally known, even if the duty ratio or the bias of the used waveform changes, one type of TN cell is used for relative comparison between the TN cells. Comparison by waveform is sufficient.
【０１０１】そこで、 １／３デューティ１／３バイアス
波形を用いた場合の電圧マージンにより比較した。視野
角（θ）はＴＮセルの法線方向より、低視角明視方向へ
１０°から４０°の範囲を想定する。また、温度は２５
℃とし、θ＝１０°における電圧印加による輝度変化
が、その飽和値の50％に達する電圧でＶON、θ＝４０°
において26％でクロストーク発生と考えＶOFF と定義し
た。電圧マージン（Ｍ）が大きい程、走査線数を増やす
ことができる。すなわち、デューティ比を大きくするこ
とができ、また、表示コントラストも優れたものにな
る。Therefore, comparison was made with the voltage margin when the 1/3 duty 1/3 bias waveform is used. The viewing angle (θ) is assumed to be in the range of 10 ° to 40 ° in the low viewing angle clear viewing direction from the normal direction of the TN cell. Also, the temperature is 25
C, and the luminance change due to voltage application at θ = 10 ° is V ON at a voltage reaching 50% of its saturation value, θ = 40 °
In 26%, crosstalk occurred and was defined as V OFF . The larger the voltage margin (M), the larger the number of scanning lines can be. That is, the duty ratio can be increased, and the display contrast becomes excellent.
【０１０２】［評価例１］メルク社製液晶組成物ZLI-15
65の透明点（Ｎ−Ｉ）は85.8℃であり、このZLI-1565
を、酸化ケイ素でコートし、ラビング処理した酸化イン
ジウム透明電極を組み合わせて作った厚さ 8μｍのセル
に注入し、１／３デューティ１／３バイアス波形で25℃
にて駆動した場合、ＶD は4.64Ｖ、Ｍは39.2％であっ
た。この組成物90重量％に本発明の実施例１の化合物を
10重量％添加したところ、組成物の透明点（Ｎ−Ｉ）は
89.5℃となりＶD は4.59Ｖ、電圧マージン（Ｍ）は41.6
％となった。すなわち、透明点および電圧マージンのい
ずれおいても、液晶物性が向上した。[Evaluation Example 1] Liquid crystal composition ZLI-15 manufactured by Merck & Co., Inc.
The clearing point (NI) of 65 is 85.8 ° C, and this ZLI-1565
Was injected into a cell with a thickness of 8 μm, which was made by combining indium oxide transparent electrodes coated with silicon oxide and rubbed, and was injected at 25 ° C with a 1/3 duty 1/3 bias waveform.
When driven in, V D is 4.64V, M was 39.2%. 90% by weight of this composition was added with the compound of Example 1 of the present invention.
When 10% by weight was added, the clearing point (N-I) of the composition was
89.5 ℃, V D is 4.59V, voltage margin (M) is 41.6
It became%. That is, the physical properties of the liquid crystal were improved at both the clearing point and the voltage margin.
【０１０３】［評価例２］前記の合成例３〜７で合成し
た化合物のうち、化合物(2A'-1) 、化合物(2A'-3) 、化
合物(3A"-2) 、化合物(4-1) を用いて、評価例１と同様
に評価した。透明点の温度は上昇し、ＶD の電圧は下
降、電圧マージンのパーセンテージは上昇した。Evaluation Example 2 Of the compounds synthesized in the above Synthesis Examples 3 to 7, compound (2A'-1), compound (2A'-3), compound (3A "-2), compound (4- 1) was used and evaluated in the same manner as in Evaluation Example 1. The temperature of the clearing point increased, the voltage of V D decreased, and the percentage of the voltage margin increased.
【０１０４】［焼き付きの評価方法］焼き付きの評価
は、デューティー駆動で１時間通電し、その後画面表示
を切り替えたとき、前の画面表示が焼き付きとして発生
しているか、いないかを目視で判定した。[Evaluation Method of Burn-in] In the burn-in evaluation, when the screen was switched on for 1 hour by duty driving and then the screen display was switched, it was visually judged whether or not the previous screen display occurred as burn-in.
【０１０５】［評価例３〜６］表１に示す化合物を同表
に示す割合（重量％）で配合した液晶組成物を調製し
た。各液晶組成物を電極付き基板間に挟持し、焼き付き
の有無を評価した結果を表１に表す。[Evaluation Examples 3 to 6] Liquid crystal compositions were prepared by mixing the compounds shown in Table 1 in the proportions (% by weight) shown in the table. Table 1 shows the results of evaluation of the presence or absence of image sticking by sandwiching each liquid crystal composition between the substrates with electrodes.
【０１０６】［参考例］本発明のジオキサボリナン化合
物を含まない液晶組成物を用いて、同様に焼き付きの有
無を評価した。結果を表１に示す。Reference Example Using the liquid crystal composition containing no dioxaborinane compound of the present invention, the presence or absence of burn-in was evaluated in the same manner. The results are shown in Table 1.
【０１０７】[0107]
【表１】 [Table 1]
【０１０８】［評価例７〜１０］評価例３のジオキサボ
リナン化合物の代わりに、合成例３〜７で合成した化合
物(2A'-1) 、化合物(2A'-3) 、化合物(3A"-2) 、化合物
(4-1) を１０重量％配合して同様の焼き付きの評価を実
施した結果、焼き付きの発生は認められなかった。[Evaluation Examples 7 to 10] Compounds (2A'-1), Compounds (2A'-3) and Compounds (3A "-2) synthesized in Synthesis Examples 3 to 7 were used in place of the dioxaborinane compound of Evaluation Example 3. ) ,Compound
When 10% by weight of (4-1) was blended and the same image sticking was evaluated, the occurrence of image sticking was not recognized.
【０１０９】[0109]
【発明の効果】本発明は一般式（１）で表される新規な
ジオキサボリナン化合物を提供する。該化合物は、液晶
化合物として有用であり、該化合物を含有する液晶組成
物を電極付きの基板間に挟持して液晶電気光学素子とし
た場合には、液晶表示素子としてのマルチプレックス駆
動特性を向上させることができる。また、該化合物は、
化学的にも安定であるため、焼き付き現象を生じない利
点もある。The present invention provides a novel dioxaborinane compound represented by the general formula (1). The compound is useful as a liquid crystal compound, and when a liquid crystal composition containing the compound is sandwiched between substrates with electrodes to form a liquid crystal electro-optical element, the multiplex drive characteristic as a liquid crystal display element is improved. Can be made. Further, the compound is
Since it is chemically stable, it also has an advantage that the image sticking phenomenon does not occur.
【図１】本発明の合成例１の化合物(n-C3H7-B-Ph-Cy-CH
=CF2) のＩＲスペクトル。縦軸は透過率（Ｔ：単位
％）、横軸は波数（ｃｍ-1）である。FIG. 1 is a compound of Synthesis Example 1 of the present invention (nC 3 H 7 -B-Ph-Cy-CH
IR spectrum of = CF 2 ). The vertical axis represents transmittance (T: unit%), and the horizontal axis represents wave number (cm -1 ).
Claims (6)
化合物。 【化１】 R1-(A1-Z1)k-B-(Z2-A2)p-(Z3-A3)m-Z4-(CH2)n-CX1=CFX2 （１） ただし、一般式（１）において、Ｒ1 、Ａ1 、Ａ2 、Ａ
3 、Ｂ、Ｚ1 、Ｚ2 、Ｚ3 、Ｚ4 、Ｘ1 、Ｘ2 、ｋ、
ｐ、ｍ、およびｎは下記の意味を示す。 Ｒ1 ：炭素数１〜１０のアルキル基またはアルケニル基
を示し、これらの基中の炭素−炭素結合間あるいはその
基と環との間の炭素−炭素結合間に、酸素原子が挿入さ
れていてもよい。 Ａ1 、Ａ2 、Ａ3 ：それぞれ互いに独立して、（ａ）１
つまたはそれ以上の隣接しないCH2 部分がエーテル性の
酸素原子で置換されていてもよいトランス−１，４−シ
クロヘキシレン基、（ｂ）１つまたは２つのCH部分が、
窒素原子で置換されていてもよい１，４−フェニレン
基、または（ｃ）１，４−シクロヘキセニレン基を示
し、（ａ）および（ｂ）は、それぞれ、基中の水素原子
がCN基またはフッ素原子で置換されていてもよい。 Ｂ：式（２）で表される２価の１，４−ジオキサボリナ
ン基を示す。 【化２】 Ｚ1 、Ｚ2 、Ｚ3 、Ｚ4 ：それぞれ互いに独立して、-C
O-O-、-O-CO-、-CH2O-、-OCH2-、-C≡C-、-CH=CH- 、-C
H2CH2-、または単結合を示す。 Ｘ1 ：水素原子、フッ素原子、または塩素原子を示す。 Ｘ2 ：水素原子、フッ素原子、塩素原子、トリフルオロ
メチル基、トリフルオロメトキシ基、炭素数１〜５のア
ルキル基、またはアルコキシ基を示す。 ｋ、ｐ、ｍ：それぞれ互いに独立して、０または１を示
し、ｋ＋ｐ＋ｍ≧１である。 ｎ：０〜４の整数を示す。1. A dioxaborinane compound represented by the general formula (1). ## STR1 ## R 1 - (A 1 -Z 1 ) k -B- (Z 2 -A 2) p - (Z 3 -A 3) m -Z 4 - (CH 2) n -CX 1 = CFX 2 (1) However, in the general formula (1), R 1 , A 1 , A 2 , A
3 , B, Z 1 , Z 2 , Z 3 , Z 4 , X 1 , X 2 , k,
p, m, and n have the following meanings. R 1 represents an alkyl group or an alkenyl group having 1 to 10 carbon atoms, and an oxygen atom is inserted between carbon-carbon bonds in these groups or between carbon-carbon bonds between the group and the ring. Good. A 1 , A 2 , A 3 : each independently of the other (a) 1
A trans-1,4-cyclohexylene group in which one or more non-adjacent CH 2 moieties may be substituted with an etheric oxygen atom, (b) one or two CH moieties,
1,4-phenylene group optionally substituted with a nitrogen atom, or (c) is a 1,4-cyclohexenylene group, wherein (a) and (b) are each a hydrogen atom in the group is a CN group. Alternatively, it may be substituted with a fluorine atom. B: A divalent 1,4-dioxaborinane group represented by the formula (2) is shown. Embedded image Z 1 , Z 2 , Z 3 , Z 4 : each independently of the other, -C
OO-, -O-CO-, -CH 2 O-, -OCH 2- , -C≡C-, -CH = CH-, -C
H 2 CH 2 — or represents a single bond. X 1 : represents a hydrogen atom, a fluorine atom or a chlorine atom. X 2 : A hydrogen atom, a fluorine atom, a chlorine atom, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group. k, p, m: each independently represent 0 or 1, and k + p + m ≧ 1. n: Shows an integer of 0 to 4.
１，４−フェニレン基である請求項１のジオキサボリナ
ン化合物。2. The dioxaborinane compound according to claim 1, wherein k is 0, p is 1, Z 2 is a single bond, and A 2 is a 1,4-phenylene group.
ナン化合物。 【化３】R1-B-Ph-Cy-CX1=CF2 （３Ａ”） ただし、一般式（３Ａ”）において、Ｒ1 、Ｂ、Ｐｈ、
Ｃｙ、およびＸ1 は下記の意味を示す。 Ｒ1 ：炭素数１〜１０のアルキル基またはアルケニル基
を示し、これらの基中の炭素−炭素結合間あるいはその
基と環との間の炭素−炭素結合間に、酸素原子が挿入さ
れていてもよい。 Ｂ：式（２）で表される２価の１，４−ジオキサボリナ
ン基を示す。 【化４】 Ｐｈ：１，４−フェニレン基を示す。 Ｃｙ：トランス−１，４−シクロヘキシレン基を示す。 Ｘ1 ：水素原子、フッ素原子、または塩素原子を示す。3. A dioxaborinane compound represented by the general formula (3A ″): embedded image R 1 —B-Ph-Cy—CX 1 ═CF 2 (3A ″) where, in the general formula (3A ″), R 1 , B, Ph,
Cy and X 1 have the following meanings. R 1 represents an alkyl group or an alkenyl group having 1 to 10 carbon atoms, and an oxygen atom is inserted between carbon-carbon bonds in these groups or between carbon-carbon bonds between the group and the ring. Good. B: A divalent 1,4-dioxaborinane group represented by the formula (2) is shown. [Chemical 4] Ph: 1,4-phenylene group is shown. Cy: Indicates a trans-1,4-cyclohexylene group. X 1 : represents a hydrogen atom, a fluorine atom or a chlorine atom.
ン化合物の１種以上を含有する液晶組成物。4. A liquid crystal composition containing at least one dioxaborinane compound according to claim 1.
ン化合物の１種以上を、液晶組成物の１００重量部に対
して０．１〜５０．０重量部含有する液晶組成物。5. A liquid crystal composition containing 0.1 to 50.0 parts by weight of one or more dioxaborinane compounds according to claim 1 to 100 parts by weight of the liquid crystal composition.
の基板間に挟持してなることを特徴とする液晶電気光学
素子。6. A liquid crystal electro-optical element comprising the liquid crystal composition according to claim 4 or 5 sandwiched between substrates with electrodes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10144195A JP3593178B2 (en) | 1995-04-25 | 1995-04-25 | Dioxaborinane compound and liquid crystal composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10144195A JP3593178B2 (en) | 1995-04-25 | 1995-04-25 | Dioxaborinane compound and liquid crystal composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08291179A true JPH08291179A (en) | 1996-11-05 |
| JP3593178B2 JP3593178B2 (en) | 2004-11-24 |
Family
ID=14300785
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10144195A Expired - Fee Related JP3593178B2 (en) | 1995-04-25 | 1995-04-25 | Dioxaborinane compound and liquid crystal composition containing the same |
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| Country | Link |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005298466A (en) * | 2003-05-14 | 2005-10-27 | Chisso Corp | Compound having perfluoropropenyl, liquid crystal composition and liquid crystal display element |
| US20140160384A1 (en) * | 2012-09-10 | 2014-06-12 | Wenlei Li | Smectic a-phase liquid crystal material |
-
1995
- 1995-04-25 JP JP10144195A patent/JP3593178B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005298466A (en) * | 2003-05-14 | 2005-10-27 | Chisso Corp | Compound having perfluoropropenyl, liquid crystal composition and liquid crystal display element |
| US20140160384A1 (en) * | 2012-09-10 | 2014-06-12 | Wenlei Li | Smectic a-phase liquid crystal material |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3593178B2 (en) | 2004-11-24 |
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