JPH0573743B2 - - Google Patents
Info
- Publication number
- JPH0573743B2 JPH0573743B2 JP17993488A JP17993488A JPH0573743B2 JP H0573743 B2 JPH0573743 B2 JP H0573743B2 JP 17993488 A JP17993488 A JP 17993488A JP 17993488 A JP17993488 A JP 17993488A JP H0573743 B2 JPH0573743 B2 JP H0573743B2
- Authority
- JP
- Japan
- Prior art keywords
- alcohol
- compounds
- substituted
- compound
- liquid crystal
- 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.)
- Expired - Fee Related
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 18
- -1 phenylpyridazine compound Chemical class 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 6
- 239000004990 Smectic liquid crystal Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XWSSUYOEOWLFEI-UHFFFAOYSA-N 3-phenylpyridazine Chemical group C1=CC=CC=C1C1=CC=CN=N1 XWSSUYOEOWLFEI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- UASUCXPJQAJBRB-NRFANRHFSA-N 3-hexyl-6-[4-[(6s)-6-methyloctoxy]phenyl]pyridazine Chemical compound N1=NC(CCCCCC)=CC=C1C1=CC=C(OCCCCC[C@@H](C)CC)C=C1 UASUCXPJQAJBRB-NRFANRHFSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- DMQYHXJZYZZOTR-AWEZNQCLSA-N [(6s)-6-methyloctyl] 4-methylbenzenesulfonate Chemical compound CC[C@H](C)CCCCCOS(=O)(=O)C1=CC=C(C)C=C1 DMQYHXJZYZZOTR-AWEZNQCLSA-N 0.000 description 1
- MNZMECMQTYGSOI-UHFFFAOYSA-N acetic acid;hydron;bromide Chemical compound Br.CC(O)=O MNZMECMQTYGSOI-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Description
（産業上の利用分野）
本発明は、液晶化合物とりわけ不斉炭素原子を
持つたアルキル基を酸素原子を介してフエニル基
に置換させているフエニルピリダジン化合物を提
供するものであつて、提供される化合物はその電
気光学的性質を利用した各種表示装置を作るのに
使用される。
（従来の技術）
フエニルピリダジン骨格を持つ液晶化合物につ
いては、ピリダジン環の３位にアルコキシ基を置
換し、６位に置換しているベンゼン環の４位にア
ルコキシ基を置換した化合物がスメクチツクＣ相
を持つ液晶材料として知られている。（Z.，
Chem.，vol.17，334（1977）），また、フエニルピ
リダジン骨格を持ち、ピリダジン環の３位に２−
メチルブチロキシ、又は１−メチルヘプチロキシ
を置換し、ベンゼン環の４位に直鎖アルキル又は
アルコキシ基を置換している化合物が２つ以上混
合されたときSc相を呈する組成物を与えること
が報告されているSc相をとる温度が50℃以上と
いうかなり高い温度である（特開昭60−22361）。
更には、同じくフエニルピリダジン骨格におい
て、ピリダジン環の３位に光学的に活性なアルコ
キシ基を置換し、ベンゼン環の４位にヘキシルオ
キシ、オクチルオキシ等を置換した化合物が中間
相を持たないということも知られている。（Mol.
Cryst.Liq.Cryst.，Vol.25，1986）
上述したように液晶化合物については、その化
学的構造と性能との間に存する関係は殆ど明確に
されていないと言つても過言ではないくらいに化
合物の性能を定めることは困難である。かかる状
況下にあつても新しい化合物を創作し性能を調
べ、より優れたものを見つけだしてゆくことが行
なわれている。
（本発明が解決しようとする問題点）
本発明は、それ自体で強誘電性カイラルスメク
チツク相を持つ新規な液晶化合物又はそれ自体で
は強誘電性カイラルスメクチツク相を持たないが
カイラルドーパントとして有用である新規な化合
物を提供するものである。
（問題点解決のための手段）
本発明によつて提供される化合物は次のように
して合成される。
(Industrial Application Field) The present invention provides a liquid crystal compound, particularly a phenylpyridazine compound in which an alkyl group having an asymmetric carbon atom is substituted with a phenyl group via an oxygen atom. These compounds are used to make various display devices that take advantage of their electro-optical properties. (Prior art) Regarding liquid crystal compounds having a phenylpyridazine skeleton, compounds in which an alkoxy group is substituted at the 3-position of the pyridazine ring and an alkoxy group is substituted at the 4-position of the benzene ring which is substituted at the 6-position are smectic C It is known as a liquid crystal material with phases. (Z.,
Chem., vol. 17, 334 (1977)), and also has a phenylpyridazine skeleton, with 2-
To provide a composition exhibiting an Sc phase when two or more compounds substituted with methylbutyloxy or 1-methylheptyloxy and substituted with a linear alkyl or alkoxy group at the 4-position of the benzene ring are mixed. It has been reported that the temperature at which the Sc phase takes place is quite high, over 50°C (Japanese Patent Application Laid-Open No. 60-22361).
Furthermore, in the same phenylpyridazine skeleton, compounds in which an optically active alkoxy group is substituted at the 3-position of the pyridazine ring and hexyloxy, octyloxy, etc. are substituted at the 4-position of the benzene ring are said to have no intermediate phase. It is also known that (Mol.
Cryst.Liq.Cryst., Vol.25, 1986) As mentioned above, it is no exaggeration to say that the relationship between the chemical structure and performance of liquid crystal compounds is hardly clear. It is difficult to define the performance of compounds. Even under such circumstances, efforts are being made to create new compounds, investigate their performance, and discover even better ones. (Problems to be Solved by the Invention) The present invention provides novel liquid crystal compounds that have a ferroelectric chiral smectic phase by themselves, or which do not have a ferroelectric chiral smectic phase by themselves but have a chiral dopant. The present invention provides a novel compound that is useful as a compound. (Means for solving the problems) The compound provided by the present invention is synthesized as follows.
【化】[ka]
【化】[ka]
【化】
（R′はメチル、ベンジル、アニシル、ベンゾ
イル、アセチルなどのちに脱離可能な基であり、
R2は直鎖アルキル基をR*は不斉炭素を持つアル
キル基を示す）
フリーデルクラフト反応は塩化アルミニウム、
三弗化ホウソなどの触媒を使用して、ジクロルエ
タン、トリクロルエタン、クロロホルムなどの溶
媒中で実施される。次に、ペンタナール、ヘキサ
ナール、ペプタナール、オクタナール、ノナナー
ル、デカナールなどの脂肪族直鎖アルデヒドを反
応させる。反応はアルコール中、炭酸ソーダ又は
炭酸カリとアミン及び５−（２−ヒドロキシエチ
ル）−４−メチル−１，３−チアゾリルのオニウ
ム（例えばアルキルハライド、ベンジルハライド
など）を使用して行なう。得られた化合物にジア
ミンを反応させたのち脱水素し、R′の種類に応
じ適した方法で（例えば臭化水素−酢酸、加水素
分解、加水分解など）R′を脱離する。
かくして得られる式で示される化合物と分子
中に不斉炭素原子を有する光学活性な２−メチル
ブチルアルコール、３−メチルペンチルアルコー
ル、４−メチルヘキシルアルコール、５−メチル
ヘプチルアルコール、６−メチルオクチルアルコ
ール、７−メチルノニルアルコール、８−メチル
デカニルアルコール、９−メチルウンデカニルア
ルコール、１−メチルヘプチルアルコール、２−
メチルオクチルアルコールなどを相当するハライ
ドに変えるか、又は、トルエンスルホニルクロリ
ド、メタンスルホニルクロリドと反応させてスル
ホン酸エステルに変えるかして、ジメチルホルム
アミド、ジメチルスルホキシド、ベンゼン、トル
エン、ジクロロエタン、ジオキサン、テトラヒド
ロフランなど適宜溶媒中、アルカリ金属例えば水
素化ナトリウム、ナトリウムアミド、炭酸カリウ
ム、水酸化ナトリウム、水酸化カリウムなどを使
つて反応させる。
かくて本発明によつて提供される化合物が得
られる。得られた化合物は、それ自体でカイラル
スメクチツクＣ（SmC*）相を持つ、あるいは
SmC*相を持たないものでドーピング材料として
使用するとき別の液晶材料にSm*Ｃ相を取らせる
ことができる即ち、カイラルドーパントとしての
使用ができるので強誘電性カイラルスメクチツク
液晶材料として使用される。
（実施例）
以下実施例を記述して本発明を更に具体的に説
明する。
実施例 １
（Ｓ）−３−ヘキシル−６−（４−（６−メチル
オクチルオキシ）フエニル）ピリダジンの合
成：
ジメチルホルムアミドにナトリウムハイドライ
ド（60％）186mgを加え、次に４−（６−ヘキシル
−３−ピリダジニル）フエノール1.66ｇを加え
た。30分攪拌したのち（Ｓ）−６−メチルオクタ
ノールのトシレート1.93ｇをジメチルホルムアミ
ド２mlに溶かして滴下した。80℃で８時間反応さ
せた。反応終了後、反応混合物を氷水中へそそぎ
いれ、酢酸エチルで抽出した。有機層を水洗乾燥
したのち、減圧濃縮した。得られた反応生成物を
シリカゲルカラムクロマトグラフイー及び再結晶
により生成して題記化合物を得た。得量0.8ｇ
［ａ］25 D＋4.25（Ｃ，2.035クロロホルム）IRスペク
トルνヌジヨ哀[C] (R' is a group that can be left off later, such as methyl, benzyl, anisyl, benzoyl, acetyl, etc.)
(R 2 is a straight-chain alkyl group, R * is an alkyl group with an asymmetric carbon) The Friedel-Crafts reaction uses aluminum chloride,
It is carried out in a solvent such as dichloroethane, trichloroethane, chloroform, etc. using a catalyst such as borax trifluoride. Next, aliphatic linear aldehydes such as pentanal, hexanal, peptanal, octanal, nonanal, and decanal are reacted. The reaction is carried out using sodium carbonate or potassium carbonate and an amine and 5-(2-hydroxyethyl)-4-methyl-1,3-thiazolyl onium (eg, alkyl halide, benzyl halide, etc.) in alcohol. After reacting the obtained compound with a diamine, it is dehydrogenated, and R' is eliminated by an appropriate method depending on the type of R' (for example, hydrogen bromide-acetic acid, hydrolysis, hydrolysis, etc.). The thus obtained compound represented by the formula and optically active 2-methylbutyl alcohol, 3-methylpentyl alcohol, 4-methylhexyl alcohol, 5-methylheptyl alcohol, and 6-methyloctyl alcohol having an asymmetric carbon atom in the molecule , 7-methylnonyl alcohol, 8-methyldecanyl alcohol, 9-methylundecanyl alcohol, 1-methylheptyl alcohol, 2-
Dimethylformamide, dimethylsulfoxide, benzene, toluene, dichloroethane, dioxane, tetrahydrofuran, etc. can be obtained by converting methyloctyl alcohol etc. into the corresponding halide, or by reacting with toluenesulfonyl chloride or methanesulfonyl chloride to convert it into a sulfonic acid ester. The reaction is carried out using an alkali metal such as sodium hydride, sodium amide, potassium carbonate, sodium hydroxide, potassium hydroxide, etc. in an appropriate solvent. The compounds provided by the present invention are thus obtained. The resulting compound itself has a chiral smectic C (SmC * ) phase, or
SmC does not have a * phase and when used as a doping material, it can be used as a ferroelectric chiral smectic liquid crystal material because it can be used as a chiral dopant in another liquid crystal material. be done. (Examples) The present invention will be explained in more detail by describing examples below. Example 1 Synthesis of (S)-3-hexyl-6-(4-(6-methyloctyloxy)phenyl)pyridazine: 186 mg of sodium hydride (60%) was added to dimethylformamide, then 4-(6-hexyl 1.66 g of -3-pyridazinyl)phenol was added. After stirring for 30 minutes, 1.93 g of (S)-6-methyloctanol tosylate dissolved in 2 ml of dimethylformamide was added dropwise. The reaction was carried out at 80°C for 8 hours. After the reaction was completed, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water, dried, and then concentrated under reduced pressure. The resulting reaction product was purified by silica gel column chromatography and recrystallization to obtain the title compound. Yield: 0.8 g [a] 25 D +4.25 (C, 2.035 chloroform) IR spectrum
Claims (1)
R2は直鎖状アルキル基を示す）[Claims] 1 Formula [Chemical formula] (In the formula, R * is an alkyl group having an asymmetric carbon atom,
R 2 represents a linear alkyl group)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17993488A JPH0232064A (en) | 1988-07-19 | 1988-07-19 | Liquid crystal compound |
| EP19890307243 EP0352054B1 (en) | 1988-07-19 | 1989-07-18 | Liquid crystal compound |
| DE1989604832 DE68904832T2 (en) | 1988-07-19 | 1989-07-18 | LIQUID CRYSTAL CONNECTION. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17993488A JPH0232064A (en) | 1988-07-19 | 1988-07-19 | Liquid crystal compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0232064A JPH0232064A (en) | 1990-02-01 |
| JPH0573743B2 true JPH0573743B2 (en) | 1993-10-15 |
Family
ID=16074490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17993488A Granted JPH0232064A (en) | 1988-07-19 | 1988-07-19 | Liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0232064A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005093437A1 (en) | 2004-03-26 | 2008-02-14 | 日本電気株式会社 | Electrical characteristic measuring method and electrical characteristic measuring apparatus |
-
1988
- 1988-07-19 JP JP17993488A patent/JPH0232064A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0232064A (en) | 1990-02-01 |
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