JPH0323895B2 - - Google Patents
Info
- Publication number
- JPH0323895B2 JPH0323895B2 JP12285188A JP12285188A JPH0323895B2 JP H0323895 B2 JPH0323895 B2 JP H0323895B2 JP 12285188 A JP12285188 A JP 12285188A JP 12285188 A JP12285188 A JP 12285188A JP H0323895 B2 JPH0323895 B2 JP H0323895B2
- Authority
- JP
- Japan
- Prior art keywords
- nitrobiphenyl
- amino
- shg
- optical
- single 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
Links
- BOFVBIYTBGDQGY-UHFFFAOYSA-N 4-(4-nitrophenyl)aniline Chemical group C1=CC(N)=CC=C1C1=CC=C([N+]([O-])=O)C=C1 BOFVBIYTBGDQGY-UHFFFAOYSA-N 0.000 claims description 14
- 239000011368 organic material Substances 0.000 claims description 6
- 239000013078 crystal Substances 0.000 description 25
- 230000003287 optical effect Effects 0.000 description 19
- 230000000694 effects Effects 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- BDLNCFCZHNKBGI-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenyl)benzene Chemical group C1=CC([N+](=O)[O-])=CC=C1C1=CC=C([N+]([O-])=O)C=C1 BDLNCFCZHNKBGI-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SCCCFNJTCDSLCY-UHFFFAOYSA-N 1-iodo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(I)C=C1 SCCCFNJTCDSLCY-UHFFFAOYSA-N 0.000 description 1
- BAJQRLZAPXASRD-UHFFFAOYSA-N 4-Nitrobiphenyl Chemical group C1=CC([N+](=O)[O-])=CC=C1C1=CC=CC=C1 BAJQRLZAPXASRD-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 229910013641 LiNbO 3 Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- GPFIZJURHXINSQ-UHFFFAOYSA-N acetic acid;nitric acid Chemical compound CC(O)=O.O[N+]([O-])=O GPFIZJURHXINSQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- XIFJZJPMHNUGRA-UHFFFAOYSA-N n-methyl-4-nitroaniline Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1 XIFJZJPMHNUGRA-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 230000008832 photodamage Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/35—Non-linear optics
- G02F1/355—Non-linear optics characterised by the materials used
- G02F1/361—Organic materials
Landscapes
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、非線形光学用有機材料、詳しくは、
４−アミノ−4′−ニトロビフエニルからなる非線
形光学用有機材料に関するものである。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to an organic material for nonlinear optics, specifically,
The present invention relates to an organic material for nonlinear optics consisting of 4-amino-4'-nitrobiphenyl.
非線形光学用材料は、レーザー発振装置等に光
波長変換素子や光シヤツター等として従来から広
く用いられている。
Nonlinear optical materials have been widely used as optical wavelength conversion elements, optical shutters, etc. in laser oscillation devices and the like.
近時、非線形光学用材料は、高速光スイツチン
グ素子、光論理ゲート及び光トランジスター等光
コンピユーター実現の為に必要不可欠な素材とし
て関係各方面の注目をあびており、新しい材料の
探究が活発に行われている。 In recent years, nonlinear optical materials have been attracting attention from various related fields as essential materials for realizing optical computers such as high-speed optical switching devices, optical logic gates, and optical transistors, and the search for new materials has been actively conducted. ing.
現在、非線形光学用材料としては、リン酸２水
素カリウム（KDP）、ニオブ酸リチウム
（LiNbO3）等の無機結晶が実用に供されており、
また、尿素、４−ニトロアニリン（PNA）、２−
メチル−４−ニトロアニリン（MNA）等を有機
結晶も知られている。 Currently, inorganic crystals such as potassium dihydrogen phosphate (KDP) and lithium niobate (LiNbO 3 ) are in practical use as materials for nonlinear optics.
Also, urea, 4-nitroaniline (PNA), 2-
Organic crystals such as methyl-4-nitroaniline (MNA) are also known.
アイイーイーイースペクトラム（IEEE
Spectram）June（1981年）第26〜28項の記載に
よれば、一般に有機結晶は、無機結晶に比べ、非
線形光学効果が大きく、第２次高調波発生
（SHG）及び第３高調波発生（THG）等の係数
が10〜100倍程度であり、光応答速度も1000倍程
度短いとされており、光損傷に対するしきい値も
大きいことが認められている。また、SHGは、
偶数次の非線形光学効果の特徴として対称中心を
持つ単結晶では発見しないことが知られている。 IEEE Spectrum (IEEE
According to Paragraphs 26 to 28 of Spectrum) June (1981), organic crystals generally have larger nonlinear optical effects than inorganic crystals, resulting in second harmonic generation (SHG) and third harmonic generation ( It is said that the coefficient of THG) etc. is about 10 to 100 times lower, the photoresponse speed is about 1000 times shorter, and the threshold for photodamage is also recognized to be large. In addition, SHG is
It is known that even-order nonlinear optical effects are not found in single crystals with a center of symmetry.
非線形光学用材料として要求される非線形光学
効果のうち特に、SHGは、変換の効率が高い等
の理由から波長変換の為の基本技術とみなされて
いる。また、SHGが大きければ、２次の非線形
光学定数が大きいという観点から、非線形光学用
材料としてはSHGが大きいものが要求されてい
る。
Among the nonlinear optical effects required for nonlinear optical materials, SHG is regarded as a basic technology for wavelength conversion because of its high conversion efficiency. Furthermore, from the viewpoint that the larger the SHG, the larger the second-order nonlinear optical constant, materials for nonlinear optics are required to have a larger SHG.
また、有機結晶は、前述した通り、一般に非線
形光学効果の大きいものであるが、室温で安定で
あることが要求される。 Further, as mentioned above, organic crystals generally have a large nonlinear optical effect, but are required to be stable at room temperature.
従来、知られている有機結晶のうち、MNAは
対称中心を持たない結晶となる為SHG活性であ
り、その強度は尿素の22倍であるが、一方、大き
な単結晶が得られにくく実用的ではないという欠
点がある。 Among conventionally known organic crystals, MNA has SHG activity because it is a crystal without a center of symmetry, and its strength is 22 times that of urea, but on the other hand, it is difficult to obtain large single crystals, making it impractical. There is a drawback that there is no
また、尿素は、大きな単結晶が得られやすい
が、SHG活性は低く、また耐湿性に劣るという
欠点がある。 Further, although large single crystals are easily obtained from urea, it has the drawbacks of low SHG activity and poor moisture resistance.
上述した通り、対称中心を持たない単結晶であ
ることによつてSHG活性が大きく、しかも、室
温で安定な有機結晶は、現在最も要求されている
ところである。 As mentioned above, organic crystals that have a high SHG activity due to being a single crystal without a center of symmetry and are stable at room temperature are currently in greatest demand.
一方、非線形光学用材料として実用に当つて
は、出来るだけ大きな単結晶であることが望ま
れ、大きな単結晶に成長させやすい非線形光学用
有機材料の開発が強く要望されている。 On the other hand, for practical use as a material for nonlinear optics, a single crystal as large as possible is desired, and there is a strong demand for the development of an organic material for nonlinear optics that can be easily grown into a large single crystal.
本発明者は、対称中心を持たない単結晶である
ことによつてSHG活性が大きく、しかも、室温
で安定であり、また、必要により、大きな単結晶
に成長させやすい有機結晶を得るべく種々検討を
重ねた結果、本発明の到達したものである。
The present inventor conducted various studies in order to obtain an organic crystal that has a high SHG activity due to being a single crystal without a center of symmetry, is stable at room temperature, and is easy to grow into a large single crystal if necessary. As a result of repeated efforts, the present invention has been achieved.
即ち、本発明は、式
で表わされる４−アミノ−4′−ニトロビフエニル
からなる非線形光学用有機材料である。 That is, the present invention provides the formula This is an organic material for nonlinear optics consisting of 4-amino-4'-nitrobiphenyl represented by:
先ず、本発明において最も重要な点は、本発明
に係る４−アミノ−4′−ニトロビフエニルが、対
称中心を持たない単結晶であることによつて尿素
の数倍のSHG活性を示し、しかも室温で安定な
点である。
First, the most important point in the present invention is that the 4-amino-4'-nitrobiphenyl according to the present invention has a SHG activity several times that of urea because it is a single crystal without a center of symmetry, and moreover, it can be used at room temperature. This is a stable point.
本発明に係る４−アミノ−4′−ニトロビフエニ
ルは、粉末状態でNd：YAGレーザー（波長＝
1064μｍ、出力３ｍＪ／パルス）の照射による測
定で第２次高調波を発生（SHG）し、入射光の
１／２の波長（532μｍ）の緑色光を発現する。 The 4-amino-4'-nitrobiphenyl according to the present invention is produced by Nd:YAG laser (wavelength =
When measured by irradiation with an output of 1064 μm and an output of 3 mJ/pulse, it generates a second harmonic (SHG) and produces green light with a wavelength (532 μm) that is half the wavelength of the incident light.
また、本発明に係る４−アミノ−4′−ニトロビ
フエニルは、mmオーダーの単結晶に成長させるこ
とが可能である。 Further, the 4-amino-4'-nitrobiphenyl according to the present invention can be grown into a single crystal on the order of mm.
次に、本発明に係る４−アミノ−4′−ニトロビ
フエニルの合成方法について述べる。 Next, a method for synthesizing 4-amino-4'-nitrobiphenyl according to the present invention will be described.
本発明に係る４−アミノ−4′−ニトロビフエニ
ルは４−ヨードニトロベンゼンを銅の存在下反応
させることにより得られる４，4′−ジニトロビフ
エニルをメタノール−ベンゼン等の混合溶媒中水
硫化ナトリウムで還元することにより得ることが
できる。 4-Amino-4'-nitrobiphenyl according to the present invention is obtained by reacting 4-iodonitrobenzene in the presence of copper and reducing 4,4'-dinitrobiphenyl with sodium bisulfide in a mixed solvent such as methanol-benzene. It can be obtained by
４，4′−ニトロビフエニルは、４−ニトロビフ
エニルを濃硝酸−濃硝酸、濃硝酸−酢酸等で反応
させても得ることができる。 4,4'-Nitrobiphenyl can also be obtained by reacting 4-nitrobiphenyl with concentrated nitric acid-concentrated nitric acid, concentrated nitric acid-acetic acid, etc.
４−アミノ−4′−ニトロビフエニルは、粉末状
態のままでも、又は、大きな単結晶にした場合で
も優れたSHG活性を発現するものである。 4-Amino-4'-nitrobiphenyl exhibits excellent SHG activity even when it is in powder form or when it is made into a large single crystal.
本発明に係る４−アミノ−4′−ニトロビフエニ
ルは、スローエバポレーシヨン法等により、大き
な単結晶に成長させることができる。大きな単結
晶に成長させるに際して用いられる溶媒として
は、アセトン、テトラヒドロフラン、クロロホル
ム等の溶解度の高い溶媒が用いられる。 The 4-amino-4'-nitrobiphenyl according to the present invention can be grown into a large single crystal by slow evaporation or the like. As the solvent used for growing a large single crystal, a solvent with high solubility such as acetone, tetrahydrofuran, chloroform, etc. is used.
次に本発明を実施例により詳細に説明する。 Next, the present invention will be explained in detail with reference to examples.
尚、実施例におけるSHG活性は、尿素を基準
としてその倍率で示した。 In addition, the SHG activity in the Examples is expressed as a magnification of urea.
＜４−アミノ−4′−ニトロビフエニルの合成＞
４−モードニトロベンゼン24.9ｇ（0.1ｍmol）
に砂を40ｇ加え220℃に加熱し撹拌する。そこへ
銅粉26ｇを1.5時間程度で加える。温度を保つた
まま2.5時間撹拌した後、反応物を加熱したエタ
ノール中に溶かし出し、濾過後ロ液を減圧下溶媒
を除去し固体を得る。この固体をシリカゲルのカ
ラムクロマトグラフイーにより分離精製後エタノ
ールで再結晶したところ、４，４−ジニトロビフ
エニルが3.90ｇ得られた。<Synthesis of 4-amino-4'-nitrobiphenyl> 24.9 g (0.1 mmol) of 4-mode nitrobenzene
Add 40g of sand, heat to 220℃ and stir. Add 26g of copper powder to it in about 1.5 hours. After stirring for 2.5 hours while maintaining the temperature, the reaction product was dissolved in heated ethanol, and after filtration, the solvent was removed from the filtrate under reduced pressure to obtain a solid. This solid was separated and purified by silica gel column chromatography and then recrystallized from ethanol to obtain 3.90 g of 4,4-dinitrobiphenyl.
このようにして得られた４，４−ジニトロビフ
エニル2.44ｇ（10ｍmol）と水硫化ナトリウム
（70％のもの）2.4ｇを、メタノール−ベンゼン
（１：２）の混合溶媒150mlに加え、20分間加熱還
流する。反応液の溶媒を減圧下除去し、得られた
固体をシリカゲルカラムで分離精製したところ４
−アミノ−4′−ニトロビフエニルが1.40ｇ得られ
た。 2.44 g (10 mmol) of the 4,4-dinitrobiphenyl thus obtained and 2.4 g of sodium bisulfide (70%) were added to 150 ml of a mixed solvent of methanol-benzene (1:2), and the mixture was heated for 20 minutes. Heat to reflux. The solvent of the reaction solution was removed under reduced pressure, and the resulting solid was separated and purified using a silica gel column.
1.40 g of -amino-4'-nitrobiphenyl was obtained.
元素分析値（C12H10N2O2として）
計算値：C67.28、H4.71、N13.08
実測値：C67.40、H4.82、N12.95
＜微結晶粉末のSHG活性＞
実施例
４−アミノ−4′−ニトロビフエニルを錠剤型成
形器を用いてペレツト状に押し固め、これに、
Nd：YAGレーザー光（波長＝1.064μｍ、出力＝
３ｍＪ／パルス）を照射すると、SHGに起因す
る532μｍの緑色散乱光が発生した。その強度を
光電変換素子により測定すると尿素の３倍程度で
あつた。Elemental analysis value (as C 12 H 10 N 2 O 2 ) Calculated value: C67.28, H4.71, N13.08 Actual value: C67.40, H4.82, N12.95 <SHG activity of microcrystalline powder> Example 4-Amino-4'-nitrobiphenyl was pressed into a pellet using a tablet molding machine, and then
Nd:YAG laser light (wavelength = 1.064μm, output =
3 mJ/pulse), green scattered light of 532 μm caused by SHG was generated. When its intensity was measured using a photoelectric conversion element, it was about three times that of urea.
＜微結晶粉末の単結晶化＞
参考例
４−アミノ−4′−ニトロビフエニル200mgをエ
タノールに溶解し、飽和溶液を作る。これを室温
で静置して溶媒を徐々に蒸発させることにより、
数日間で１mm×１mm×２mm程度の単結晶を得た。
この結晶は室温で長期に渡り安定であり、Nd：
YAGレーザー光照射により、1/2波長（532nｍ）
の位相整合したレーザー光が得られた。<Single crystallization of microcrystalline powder> Reference example Dissolve 200 mg of 4-amino-4'-nitrobiphenyl in ethanol to make a saturated solution. By leaving this at room temperature and gradually evaporating the solvent,
A single crystal of approximately 1 mm x 1 mm x 2 mm was obtained in several days.
This crystal is stable for a long time at room temperature, and Nd:
1/2 wavelength (532nm) by YAG laser light irradiation
Phase-matched laser light was obtained.
本発明に係る４−アミノ−4′−ニトロビフエニ
ルからなる非線形光学溶有機材料は、前出実施例
に示した通り、SHGが尿素の数倍と大きく、し
かも室温で安定であり、また、前出参考例に示し
た通り、大きな単結晶に成長させやすいものであ
り、従つて、光波長変換素子、光シヤツター、高
速光スイツチング素子及び光論理ゲート並びに光
トランジスター等の素材用の材料として好適であ
る。
As shown in the above example, the nonlinear optically soluble organic material made of 4-amino-4'-nitrobiphenyl according to the present invention has an SHG several times higher than that of urea, and is stable at room temperature. As shown in the reference example, it is easy to grow into a large single crystal, and is therefore suitable as a material for optical wavelength conversion elements, optical shutters, high-speed optical switching elements, optical logic gates, optical transistors, etc. .
Claims (1)
らなる非線形光学用有機材料。[Claims] 1 formula An organic material for nonlinear optics consisting of 4-amino-4'-nitrobiphenyl represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12285188A JPH0192727A (en) | 1985-09-10 | 1988-05-19 | Nonlinear optical organic material |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19970585A JPS6259934A (en) | 1985-09-10 | 1985-09-10 | Nonlinear optical organic material |
| JP12285188A JPH0192727A (en) | 1985-09-10 | 1988-05-19 | Nonlinear optical organic material |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19970585A Division JPS6259934A (en) | 1985-09-10 | 1985-09-10 | Nonlinear optical organic material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0192727A JPH0192727A (en) | 1989-04-12 |
| JPH0323895B2 true JPH0323895B2 (en) | 1991-03-29 |
Family
ID=26459894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12285188A Granted JPH0192727A (en) | 1985-09-10 | 1988-05-19 | Nonlinear optical organic material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0192727A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100227254B1 (en) * | 1997-07-18 | 1999-11-01 | 노관호 | Magnetic induction device |
| JP2004063988A (en) | 2002-07-31 | 2004-02-26 | Canon Inc | Illumination optical system, aligner having the system, and method of manufacturing device |
-
1988
- 1988-05-19 JP JP12285188A patent/JPH0192727A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0192727A (en) | 1989-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |