JPS61205290A - Novel di(9-anthryl)dimethylgermane compound and production thereof - Google Patents
Novel di(9-anthryl)dimethylgermane compound and production thereofInfo
- Publication number
- JPS61205290A JPS61205290A JP60044801A JP4480185A JPS61205290A JP S61205290 A JPS61205290 A JP S61205290A JP 60044801 A JP60044801 A JP 60044801A JP 4480185 A JP4480185 A JP 4480185A JP S61205290 A JPS61205290 A JP S61205290A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- anthryl
- dimethylgermane
- novel
- formula
- 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
- -1 di(9-anthryl)dimethylgermane compound Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- QGMXETIFYMAMGW-UHFFFAOYSA-N di(anthracen-9-yl)-dimethylgermane Chemical compound C1=CC=C2C([Ge](C)(C=3C4=CC=CC=C4C=C4C=CC=CC4=3)C)=C(C=CC=C3)C3=CC2=C1 QGMXETIFYMAMGW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims 5
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims 1
- OXTURSYJKMYFLT-UHFFFAOYSA-N dichlorogermane Chemical compound Cl[GeH2]Cl OXTURSYJKMYFLT-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 3
- GVQYFWLEJIPDDP-UHFFFAOYSA-N dichloromethylgermane Chemical compound ClC(Cl)[GeH3] GVQYFWLEJIPDDP-UHFFFAOYSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004896 high resolution mass spectrometry Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YRMRYBWOAURIMP-UHFFFAOYSA-N 9-(anthracen-9-ylmethyl)anthracene Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C4C=CC=CC4=3)=C(C=CC=C3)C3=CC2=C1 YRMRYBWOAURIMP-UHFFFAOYSA-N 0.000 description 2
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- YQECBLVSMFAWIZ-UHFFFAOYSA-N dichloro(dimethyl)germane Chemical compound C[Ge](C)(Cl)Cl YQECBLVSMFAWIZ-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002290 germanium Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Landscapes
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Abstract
Description
【発明の詳細な説明】
〔発明の利用分野〕
本発明は、新規ジ（９−アントリル）ジメチルゲルマン
系化合物のおよびそのｙＡ造方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Application of the Invention] The present invention relates to a novel di(9-anthryl)dimethylgermane compound and a method for producing yA thereof.
フォトクロミック材料は、光によって可逆的にその色調
が変化することから、光記録材料としての応用が期待さ
れ、広く研究されている６例えば。Photochromic materials, whose color tone changes reversibly with light, are expected to be used as optical recording materials and have been widely studied, for example.
無機化合物としてはＣａＦ、およびＮａＦなどの結晶が
、また有機化合物としてはスピロピランおよびその誘導
体がそれぞれ主に研究されている。有機材料は、無機材
料にくらべて安定な薄膜を容易に作製できる点ですぐれ
ている。Crystals such as CaF and NaF are mainly studied as inorganic compounds, and spiropyran and its derivatives are mainly studied as organic compounds. Organic materials are superior to inorganic materials in that stable thin films can be easily produced.
（発明、第８２巻、１９８５年、第１号２頁５０〜５５
）〔発明の目的〕
本発明の目的は、可逆的に光学特性を変化させることの
できる新規なジ（９−アントリル）ジメチルゲルマン系
化合物のおよびその製造方法を提供することにある。(Invention, Vol. 82, 1985, No. 1, pp. 2, 50-55
) [Object of the Invention] An object of the present invention is to provide a novel di(9-anthryl)dimethylgermane compound whose optical properties can be changed reversibly and a method for producing the same.
従来、ジ（９−アントリル）メタンは光照射によって、
［４＋４］付加体を与えることが知られていた。このジ
（９−アントリル）メタンのゲルマニウム類縁体を合成
し、その光反応性を調べた結果、以下に示す、新規なジ
（９−アントリル）ジメチルゲルマン系化合物の光学特
性が、可逆的に変化することを見出した。Conventionally, di(9-anthryl)methane was treated by light irradiation.
It was known to give a [4+4] adduct. As a result of synthesizing a germanium analog of this di(9-anthryl)methane and investigating its photoreactivity, the optical properties of the new di(9-anthryl) dimethylgermane compound shown below changed reversibly. I found out what to do.
本発明の新規ジ（９−アントリル）ジメチルゲルマン系
化合物は、以下の一般式（１）で示される。The novel di(9-anthryl)dimethylgermane compound of the present invention is represented by the following general formula (1).
ただし、一般式（１）中のＲは、水素またはアルキル基
を表す。However, R in general formula (1) represents hydrogen or an alkyl group.
本発明による、新規ジ（９−アントリル）ジメチルゲル
マン系化合物は、たとえば次のような反応により合成で
きる。The novel di(9-anthryl)dimethylgermane compound according to the present invention can be synthesized, for example, by the following reaction.
ジ（９−アントリル）ジメチルゲルマン（一般式（１）
において、Ｒ＝水素である化合物）は、９−ブロモアン
トラセンをし一ブチルリチウムでリチオ化したのち、ジ
クロロジメチルゲルマンと反応させることにより合成で
きる。Di(9-anthryl)dimethylgermane (general formula (1)
The compound in which R=hydrogen) can be synthesized by lithiation of 9-bromoanthracene with monobutyllithium, followed by reaction with dichlorodimethylgermane.
［発明の実施例〕 以下、本発明の合成例および実施例を示す。[Embodiments of the invention] Synthesis examples and examples of the present invention are shown below.
合成例
アルゴン雰囲気下、−７０℃の９−ブロモアントラセン
（２，５０ｇ）のテトラヒドロフラン溶液（１ｏｏｍｆ
）にｔ−ブチルリチウムのペンタン溶液（１，７４ｍｏ
Ｊ！／互）を滴下した。−７０℃まで冷した溶液中にジ
クロロジメチルゲルマン（８４５ｍｇ）の５ｍ１テトラ
ヒドロフラン溶液を滴下した。Synthesis Example Under an argon atmosphere, a solution of 9-bromoanthracene (2.50 g) in tetrahydrofuran (1 oomf.
) with a pentane solution of t-butyllithium (1,74 mo
J! / mutual) was added dropwise. A solution of dichlorodimethylgermane (845 mg) in 5 ml of tetrahydrofuran was added dropwise to the solution cooled to -70°C.
一７０℃で３０分間撹拌後、１時間かけて室温にもどし
た。溶媒を留去し、得られた残渣をペンゼンに溶かし、
塩をろ別後、シリカゲルカラムに通して分解物を除いた
。ベンゼンとエタノールの混合７８ｍから再結晶するこ
とにより、本発明のジ（９−アントリル）ジメチルゲル
マン（淡黄色）を得た。同定は水素核磁気共鳴スペクト
ル（”Ｈ−ＮＭＲ）および高分解能質量分析スペクトル
によった・
その結果を次に示す。After stirring at -70°C for 30 minutes, the mixture was returned to room temperature over 1 hour. The solvent was distilled off, the resulting residue was dissolved in penzene,
After filtering off the salt, it was passed through a silica gel column to remove decomposed products. Di(9-anthryl)dimethylgermane (pale yellow) of the present invention was obtained by recrystallizing from 78m of a mixture of benzene and ethanol. Identification was done by hydrogen nuclear magnetic resonance spectrum (H-NMR) and high-resolution mass spectrometry. The results are shown below.
収率＝６８％
融点＝１６６〜１６７℃
水素核磁気共鳴 （δＰＰＩＩ／ＣＣｌ４ ）１．３
９ （６Ｈ，シングレット）７．０〜７．５
（８Ｈ，マルチプレット）７．８〜８．０（４Ｈ，マル
チプレット）８．２〜８．４ （６Ｈ，マルチプレッ
ト）高分解能質量分析
Ｃ３，Ｈ，、”Ｇｅの計算値＝４５８．１０９０実測値
＝４５８゜１１２３
実施例
上記の合成例で合成した本発明新規化合物ジ（９−アン
トリル）ジメチルゲルマン（淡黄色）（０，１１ｍｍｏ
又）のベンゼン溶液（・７ｍ文）を内径８ｍｍのパイレ
ックス管に入れ、脱気した後、高圧水銀灯（４５０Ｗ）
を用いて１時間光照射した。反応物を薄層クロマトグラ
フ（シリカゲル）で精製し、１３．１３−ジメチル−５
ａ、 １３ｂ−ジヒドロ−５，１３ａ−オルト−ベンザ
ノー１３ト１３−ゲルマシクロペンタ（ｒｓｔ）ペンタ
フェン（ｐ！Ａ色）を得た。同定は水素核磁気共鳴およ
び高分解能質量分析によった。その結果を以下に示す。Yield = 68% Melting point = 166-167°C Hydrogen nuclear magnetic resonance (δPPII/CCl4) 1.3
9 (6H, singlet) 7.0-7.5
(8H, multiplet) 7.8-8.0 (4H, multiplet) 8.2-8.4 (6H, multiplet) High-resolution mass spectrometry C3,H,, "Calculated value of Ge = 458.1090 Actual value = 458°1123 Example New compound of the present invention synthesized in the above synthesis example Di(9-anthryl)dimethylgermane (light yellow) (0,11 mmo
Also, put the benzene solution (7 m long) into a Pyrex tube with an inner diameter of 8 mm, degas it, and then heat it with a high-pressure mercury lamp (450 W).
The sample was irradiated with light for 1 hour. The reaction product was purified by thin layer chromatography (silica gel) and 13.13-dimethyl-5
a, 13b-dihydro-5,13a-ortho-benzanol 13-germacyclopenta(rst)pentaphene (p!A color) was obtained. Identification was by hydrogen nuclear magnetic resonance and high-resolution mass spectrometry. The results are shown below.
収率＝７１％
融点＝１９４℃（分解）
水素核磁気共鳴 （δｐｐ腸／ＣＣ１，）０．９５
（３Ｈ，シングレット）１．４３ （３Ｈ，シ
ングレット）３．２６（ＩＨ，ダブレット、スピン−ス
ピン分裂＝１２．０．３．２．２．４．１．８Ｈｚ）３
．９０（ＬＨ，ダブレット、スピン−スピン分裂＝１２
．０）
４．２５（ＬＨ，ダブレット、スピン−スピン分裂＝２
．４Ｈｚ）
５．７５（ＩＨ，２つのダブレット、スピン−スピン分
裂＝９．６．３．２Ｈｚ ）
ｓ、１４（ＬＨ，２つのダブレット、スピン−スピン分
裂＝９．６． ＩＪＨｚ ）
６．６〜７．８（１３Ｈ，マルチプレット）高分解能質
量分析
ＣａｏＨ１４”Ｇａの計算値＝４５８．１０９０実測値
＝４５８．１１０３
実施例２
実施例１で合成した１３．１３−ジメチル−５ａ、１３
ｂ−ジヒドロ−５，１３ａ−０−ベンザノー１３１１−
１３−ゲルマシクロペンタ（ｒｓｔ）ペンタフェン（無
色）８Ｑｍｇのベンゼン溶液（１ｍｌりを封管中２００
’Ｃで１時間加熱したところ定量的にジ（９−アントリ
ル）ジメチルゲルマン（淡黄色）を再ントリル）ジメチ
ルゲルマン系化合物は、光照射により色調および構造の
異なる（４＋２３付加体を高収率で生成し、その（４＋
２）付加体は加熱により定量的に原料を再生する。した
がってこの色調の可逆的変化を利用して、本新規化合物
を書き換え可能型光ディスクの記録媒体に適用できる。Yield = 71% Melting point = 194°C (decomposition) Hydrogen nuclear magnetic resonance (δpp/CC1,) 0.95
(3H, singlet) 1.43 (3H, singlet) 3.26 (IH, doublet, spin-spin splitting = 12.0.3.2.2.4.1.8Hz) 3
．． 90 (LH, doublet, spin-spin splitting = 12
．． 0) 4.25 (LH, doublet, spin-spin splitting = 2
．． 4Hz) 5.75 (IH, two doublets, spin-spin splitting = 9.6.3.2Hz) s, 14 (LH, two doublets, spin-spin splitting = 9.6. IJHz) 6.6~ 7.8 (13H, multiplet) high resolution mass spectrometry Calculated value of CaoH14''Ga = 458.1090 Actual value = 458.1103 Example 2 13.13-dimethyl-5a, 13 synthesized in Example 1
b-dihydro-5,13a-0-benzanol 1311-
13-Gelmacyclopenta(rst)Pentafene (colorless) 8Qmg of benzene solution (1ml in a sealed tube at 200%
When heated for 1 hour at generate and its (4+
2) The adduct regenerates the raw material quantitatively by heating. Therefore, by utilizing this reversible change in color tone, the present novel compound can be applied to recording media for rewritable optical discs.
たとえば上記合成例の方法で合成した化合物を。For example, the compound synthesized by the method in the above synthesis example.
ベンゼンに溶解して得たベンゼン溶液（５〜１０重量％
）を基板上に塗布し、乾燥成膜する。これにレーザー光
等を照射すると乃部的な色調が変化し、照射部分と他の
部分との光線の反射率の差が生じる。この反射率の差の
生成と検出により、情報の記録と再生が可能である。次
に１色調の変化した部分をレーザー光等で加熱すれば色
調はもとに戻り、記録した情報の消去ができる。Benzene solution obtained by dissolving in benzene (5-10% by weight)
) is applied onto the substrate and dried to form a film. When this is irradiated with a laser beam or the like, the color tone of the part changes, and a difference in light reflectance occurs between the irradiated part and other parts. By generating and detecting this reflectance difference, information can be recorded and reproduced. Next, if the area where one color tone has changed is heated with a laser beam or the like, the color tone will return to its original state and the recorded information can be erased.
また、本新規化合物は光照射による色調変化と同時に構
造も変化するので、？８媒への溶解度が光照射前後で変
化する。これを利用して本新規化合物を光レジストに用
いることができる。たとえば上記と同様の方法により作
成した本新規化合物薄暎りにマスクをのせ光照射すると
、マスクされた部分とされていない部分とで溶媒への溶
解度の差が生じる。この薄膜を溶媒で処理することによ
りレジストパターンを形成できる。In addition, the structure of this new compound changes at the same time as the color tone changes due to light irradiation. The solubility in 8 medium changes before and after light irradiation. Taking advantage of this, the new compound can be used in photoresists. For example, when a mask is placed on a thin strip of the novel compound prepared by the same method as described above and irradiated with light, a difference in solubility in the solvent occurs between the masked portion and the unmasked portion. A resist pattern can be formed by treating this thin film with a solvent.
Claims (1)
示す、）で表される化合物よりなることを特徴とす新規
ジ（９−アントリル）ジメチルゲルマン系化合物。 ２、ジ（９−アントリル）ジメチルゲルマンであること
を特徴とする特許請求の範囲第１項記載の新規ジ（９−
アントリル）ジメチルゲルマン系化合物。 ３、一般式（２）で表される化合物と、ジクロロゲルマ
ン（３）とを反応させて、一般式（１）で示される化合
物を得ることを特徴とする新規ジ（９−アントリル）ジ
メチルゲルマン系化合物の製造方法。 ▲数式、化学式、表等があります▼（２）＋ＭｅＧｅＣ
１＿２（３）→ ▲数式、化学式、表等があります▼（１）＋２ＬｉＣｌ
（３） ただし一般式（１）と（２）の中のＲはたとえば水素な
どの置換基である。 ４、一般式（２）で表される化合物が、 ▲数式、化学式、表等があります▼ であり、一般式（ I ）で示される化合物が ▲数式、化学式、表等があります▼ であることを特徴とする特許請求の範囲第３項記載の新
規ジ（９−アントリル）ジメチルゲルマン系化合物の製
造方法。[Claims] 1. General formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(1) (However, R in general formula (1) represents an alkyl group or hydrogen) A novel di(9-anthryl)dimethylgermane compound characterized by comprising a compound. 2, di(9-anthryl)dimethylgermane as claimed in claim 1.
anthryl) dimethyl germane compound. 3. A novel di(9-anthryl)dimethylgermane characterized in that a compound represented by the general formula (2) is reacted with dichlorogermane (3) to obtain a compound represented by the general formula (1). A method for producing a series compound. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(2)+MeGeC
1_2(3)→ ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1)+2LiCl
(3) However, R in general formulas (1) and (2) is a substituent such as hydrogen. 4. The compound represented by general formula (2) is ▲There is a mathematical formula, chemical formula, table, etc.▼, and the compound represented by general formula (I) is ▲There is a mathematical formula, chemical formula, table, etc.▼ A method for producing a novel di(9-anthryl)dimethylgermane compound according to claim 3, characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60044801A JPS61205290A (en) | 1985-03-08 | 1985-03-08 | Novel di(9-anthryl)dimethylgermane compound and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60044801A JPS61205290A (en) | 1985-03-08 | 1985-03-08 | Novel di(9-anthryl)dimethylgermane compound and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61205290A true JPS61205290A (en) | 1986-09-11 |
| JPH058715B2 JPH058715B2 (en) | 1993-02-02 |
Family
ID=12701526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60044801A Granted JPS61205290A (en) | 1985-03-08 | 1985-03-08 | Novel di(9-anthryl)dimethylgermane compound and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61205290A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005317275A (en) * | 2004-04-27 | 2005-11-10 | Fuji Photo Film Co Ltd | Organic electroluminescent element |
| DE112020005305T5 (en) | 2019-12-17 | 2022-09-15 | Murata Manufacturing Co., Ltd. | ELECTRONIC SWITCH |
-
1985
- 1985-03-08 JP JP60044801A patent/JPS61205290A/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005317275A (en) * | 2004-04-27 | 2005-11-10 | Fuji Photo Film Co Ltd | Organic electroluminescent element |
| JP4708727B2 (en) * | 2004-04-27 | 2011-06-22 | 富士フイルム株式会社 | Organic electroluminescence device |
| DE112020005305T5 (en) | 2019-12-17 | 2022-09-15 | Murata Manufacturing Co., Ltd. | ELECTRONIC SWITCH |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH058715B2 (en) | 1993-02-02 |
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