JPH0192727A - Nonlinear optical organic material - Google Patents
Nonlinear optical organic materialInfo
- Publication number
- JPH0192727A JPH0192727A JP12285188A JP12285188A JPH0192727A JP H0192727 A JPH0192727 A JP H0192727A JP 12285188 A JP12285188 A JP 12285188A JP 12285188 A JP12285188 A JP 12285188A JP H0192727 A JPH0192727 A JP H0192727A
- Authority
- JP
- Japan
- Prior art keywords
- optical
- single crystal
- wavelength
- nitrobiphenyl
- amino
- 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
- 239000011368 organic material Substances 0.000 title claims description 7
- 230000003287 optical effect Effects 0.000 title abstract description 26
- 239000000126 substance Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 abstract description 29
- 239000000463 material Substances 0.000 abstract description 14
- 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 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 9
- 239000004202 carbamide Substances 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 239000000843 powder Substances 0.000 abstract description 3
- 238000005259 measurement Methods 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 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
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent 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
- 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
- 239000012046 mixed solvent Substances 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
- 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
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 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 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000008188 pellet Substances 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
- 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
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- IERBVBGUKBHALB-UHFFFAOYSA-K tripotassium;phosphate;dihydrate Chemical compound O.O.[K+].[K+].[K+].[O-]P([O-])([O-])=O IERBVBGUKBHALB-UHFFFAOYSA-K 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)
Abstract
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′−二トロビフェ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 [Field of Industrial Application] The present invention relates to an organic material for nonlinear optics, and more particularly, to an organic material for nonlinear optics comprising 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、高速光スイッチング素子、
光論理ゲ、−ト及び光トランジスター等光コンビニータ
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
。Recently, nonlinear optical materials have been used for high-speed optical switching devices,
It is attracting attention from various related fields as an indispensable material for realizing optical combiners such as optical logic gates and optical transistors, and new materials are being actively explored.
現在、非線形光学用材料としては、リン酸２水累カリウ
ム（Ｋ Ｄ Ｐ）、ニオブ酸リチウム（ＬｉＮｂＯｓ）
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、ｒ Ｐ Ｎ Ａ、）、２−メチル−４
−二トロアニリン（Ｍ Ｎ Ａ）等の有機結晶も知られ
ている。Currently, nonlinear optical materials include potassium dihydrate phosphate (KDP) and lithium niobate (LiNbOs).
Inorganic crystals such as urea, 4-
Nitroaniline, rPNA,), 2-methyl-4
Organic crystals such as -nitroaniline (MNA) are also known.
アイイーイーイースペクトラム（ＩＥＥＥＳｐｅｃｔｒ
ａｍ） Ｊｕｎｅ（１９８１年）第２６〜３３頁の記載
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次高調波発生（Ｔ ＨＧ）等の係数が１０〜１００倍
程倍程卜り、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
am) June (1981), pp. 26 to 33, organic crystals generally have larger nonlinear optical effects than inorganic crystals, and are highly effective in second harmonic generation (SHG) and third harmonic generation. It is said that the coefficients such as (THG) are about 10 to 100 times higher, the photoresponse speed is about 1000 times shorter, and the threshold for photodamage is also recognized to be higher. Furthermore, it is known that SHG is not found in single crystals that have a center of symmetry as a feature of even-order nonlinear optical effects.
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, a material for nonlinear optics is 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、太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. It has the disadvantage of not being accurate.
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。In addition, urea is easy to obtain large single crystals, but SHG
It has the drawbacks of low 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
よって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たっては、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, in 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
って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慕、本発明に到達し
たものである。The present inventor has discovered that the SHG activity is large due to the fact that it is a single crystal without a center of symmetry, and is stable at room temperature.
In addition, the present invention was developed after various studies to obtain an organic crystal that can be easily grown into a large single crystal if necessary.
で表わされる４−アミノ−４′−二トロビフェニルから
なる非線形光学用有機材料である。This is an organic material for nonlinear optics consisting of 4-amino-4'-nitrobiphenyl represented by:
先ず、本発明にふいて最も重要な点は、本発明に係る４
−アミノ−４′−二トロビフェニルが、対称中心を持た
ない単結晶であることによって尿素の数倍の５）（Ｇ活
性を示し、しかも室温で安定な点である。First, the most important point regarding the present invention is the 4 points related to the present invention.
Since -amino-4'-nitrobiphenyl is a single crystal with no center of symmetry, it exhibits G activity several times that of urea, and is stable at room temperature.
本発明に係る４−アミノ−４′−二トロビフェニルは、
粉末状態でＮｄ：ＹＡＧレーザ−（波長＝１．０６４μ
ｍ１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）Ｌ、入射光の１／２の波長（５３
２μｍ）の緑色光を発現する。4-Amino-4'-nitrobiphenyl according to the present invention is
Nd:YAG laser (wavelength = 1.064μ) in powder state
2nd harmonic is generated (SHG) by measurement by irradiation with m1 output 3 mJ/pulse), and 1/2 wavelength of the incident light (53
2 μm).
また、本発明に係る４−アミノ−４′−二トロビフェニ
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′−二トロビフェニ
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′−二トロビフェニルは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′−ジニトロビフェニルをメタノー
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。The 4-amino-4'-nitrobiphenyl according to the present invention is 4
It can be obtained by reducing 4,4'-dinitrobiphenyl obtained by reacting -iodonitrobenzene in the presence of copper with sodium hydrosulfide in a mixed solvent such as methanol-benzene.
４．４’−二トロビフェニルは、４−ニトロビフェニル
を濃硝酸−濃硫酸、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 sulfuric acid, concentrated nitric acid-acetic acid, etc.
４−アミノ−４′、−ニトロビフェニルは、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Ｓ
ＨＧ活性を発現するものである。4-Amino-4',-nitrobiphenyl has excellent S
It expresses HG activity.
本発明に係る４−アミノ−４′−二トロビフェニルは、
スローエバポレーション法等により、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〔実施例］
次に本発明を実施例により詳細に説明する。4-Amino-4'-nitrobiphenyl according to the present invention is
It can be grown into a large single crystal by slow evaporation or the like. Examples of solvents used for growing large single crystals include acetone, tetrahydrofuran, and chlorophor.Examples 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 based on urea.
く４−アミノ−４′−二トロビフェニルの合成〉４−ヨ
ードニトロベンゼン２４．９ ｇ （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。温度を保った
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、濾過後口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
フィ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−ジニトロビフェニルが３．９０ ｇ得られた
。Synthesis of 4-amino-4'-nitrobiphenyl> 4-iodonitrobenzene 24.9 g (0.1 mmol)
Add 40g of sand, heat to 220°C and stir. Add 26g of copper powder to it over about 1.5 hours. After stirring for 2.5 hours while maintaining the temperature, the reaction product was dissolved in heated ethanol, filtered, and the solvent was removed from the mouth liquid 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−ジニトロビフェニル２
．４４ ｇ （１０ｍ ｍｏｌ）と水硫化ナトリウム（
７０％のもの＞２．４ ｇを、メタノール−ベンゼン（
１： ２）の混合溶媒１５０ｍ１に加え、２０分間加熱
還流する。4,4-dinitrobiphenyl 2 thus obtained
．． 44 g (10 mmol) and sodium bisulfide (
>2.4 g of 70% methanol-benzene (
Add to 150 ml of a mixed solvent of 1:2) and heat under reflux for 20 minutes.
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′−二ト
ロビフェニルが１．４０ｇ得られた。The solvent of the reaction solution was removed under reduced pressure, and the resulting solid was separated and purified using a silica gel column, yielding 1.40 g of 4-amino-4'-nitrobiphenyl.
元素分析値（ＣＩ２ Ｈｌ。Ｎ２Ｏ２として）計算値：
Ｃ６７，２８、Ｈ４，７１、Ｎ１３．０８実測値：Ｃ６
７，４０、Ｈ４，８２、Ｎ１２．９５〈微結晶粉末のＳ
ＨＧ活性〉
実施例
４−アミノ−４′−二トロビフェニルを錠剤型成形器を
用いてペレット状に押し固め、これに、Ｎｄ：ＹＡＧｔ
ｚ−デー光（波長＝１．０６４μｍ、出力＝３＋ｎＪ／
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倍程度であった０
〈微結晶粉末の単結晶化〉
参考例
４−アミノ−４′−二トロビフェニル２００ｍｇをエタ
ノールに溶解し、飽和溶液を作る。これを室数日間で１
市×１ＩＩＩＩｉＸ２１１Ｉ１１程度の単結晶を得た。Elemental analysis value (CI2 Hl. as N2O2) Calculated value:
C67,28, H4,71, N13.08 Actual value: C6
7,40, H4,82, N12.95〈S of microcrystalline powder
HG activity> Example 4-Amino-4'-nitrobiphenyl was pressed into a pellet using a tablet molding machine, and Nd:YAGt
Z-day light (wavelength = 1.064μm, output = 3+nJ/
When irradiated with a pulse), 532 μm green scattered light caused by SHG was generated. When its intensity was measured using a photoelectric conversion element, it was about three times that of urea. . 1 in a few days
A single crystal of approximately 1×1IIIiX211I11 was obtained.
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。This crystal is stable for a long time at room temperature and is
By laser light irradiation, phase-matched laser light of 1/2 wavelength (532 nm) was obtained.
本発明に係る４−アミノ−４′−二トロビフェニルから
なる非線形光学用有機材料は、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、従って、光波長変換素子、光
シヤツター、高速光スイッ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 previous example, the organic material for nonlinear optics made of 4-amino-4'-nitrobiphenyl according to the present invention has SHG several times larger than that of urea, and is stable at room temperature. As shown in the reference example above, it is easy to grow into large single crystals, 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. be.
Claims (1)
非線形光学用有機材料。[Claims] 1. An organic material for nonlinear optics consisting of 4-amino-4'-nitropiphenyl represented by the formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼.
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 true JPH0192727A (en) | 1989-04-12 |
| JPH0323895B2 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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100227254B1 (en) * | 1997-07-18 | 1999-11-01 | 노관호 | Magnetic induction device |
| US6876437B2 (en) | 2002-07-31 | 2005-04-05 | Canon Kabushiki Kaisha | Illumination optical system, exposure method and apparatus using the same |
-
1988
- 1988-05-19 JP JP12285188A patent/JPH0192727A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100227254B1 (en) * | 1997-07-18 | 1999-11-01 | 노관호 | Magnetic induction device |
| US6876437B2 (en) | 2002-07-31 | 2005-04-05 | Canon Kabushiki Kaisha | Illumination optical system, exposure method and apparatus using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0323895B2 (en) | 1991-03-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |