JPH02215753A - N-substituted-2-thiophenealdehyde amidinohydrazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof - Google Patents
N-substituted-2-thiophenealdehyde amidinohydrazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereofInfo
- Publication number
- JPH02215753A JPH02215753A JP3584589A JP3584589A JPH02215753A JP H02215753 A JPH02215753 A JP H02215753A JP 3584589 A JP3584589 A JP 3584589A JP 3584589 A JP3584589 A JP 3584589A JP H02215753 A JPH02215753 A JP H02215753A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- thiophenealdehyde
- amidinohydrazone
- substituted
- tetracyanoquinodimethane
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 230000007935 neutral effect Effects 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 27
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract description 7
- 239000004065 semiconductor Substances 0.000 abstract description 4
- 239000004020 conductor Substances 0.000 abstract description 3
- 239000012776 electronic material Substances 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 2
- 239000011261 inert gas Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000003990 capacitor Substances 0.000 description 4
- PSZMRWZPIAGXQW-UHFFFAOYSA-N 2-(thiophen-2-ylmethylideneamino)guanidine Chemical compound NC(N)=NN=CC1=CC=CS1 PSZMRWZPIAGXQW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007784 solid electrolyte Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- -1 alkyl cellosolve Chemical compound 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (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、電子機器分野あるいは電子材料分野などにお
ける導電性材料として注目されている有機半導体に関す
るもので、特に新規物質としてのＮ−置換−２−チオフ
ェンアルデヒドアミジノヒドラゾン・７，７，８．８−
テトラシアノキノジメタン錯塩類およびその製造方法に
関するものである。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to an organic semiconductor that is attracting attention as a conductive material in the field of electronic equipment or electronic materials, and in particular, relates to an organic semiconductor that is attracting attention as a conductive material in the field of electronic devices or electronic materials. 2-thiophenealdehyde amidinohydrazone 7,7,8.8-
The present invention relates to tetracyanoquinodimethane complex salts and a method for producing the same.
［発明の概要］
更に詳しくは、下記の式［１］で表わされる新規有機半
導体（新規化合物）としてのＮ−置換一２−チオフェン
アルデヒドアミジノヒドラゾン・７．７，８．８−テト
ラシアノキノジメタン錯塩類およびその製造方法を提供
するものである。[Summary of the Invention] More specifically, N-substituted 1-2-thiophenealdehyde amidinohydrazone/7,7,8,8-tetracyanoquinodi as a novel organic semiconductor (new compound) represented by the following formula [1] The present invention provides methane complex salts and a method for producing the same.
■
下記の式［３］で表わされるＴＣＮＱとただし、式［１
］中、Ｒは０１〜Ｃ６のアルキル基を示す０ｍは１モル
の錯塩に含まれる中性７．７，８．８−テトラシアノキ
ノジメタンのモル数に対応する正の数（０，５〜１．５
）を意味する。■ TCNQ expressed by the following formula [3] and the formula [1]
], R represents an alkyl group of 01 to C6; 0m is a positive number (0,5 ~1.5
) means.
なお、説明の便宜上、７，７，８．８−テトラシアノキ
ノジメタンを以下、ＴＣＮＱと称す。In addition, for convenience of explanation, 7,7,8.8-tetracyanoquinodimethane is hereinafter referred to as TCNQ.
次に、上記の式［１１で示した化合物は、下記の式［２
］で表わされるＮ−置換−２−チオフェンアルデヒドア
ミジノヒドラゾン・第四アンモニウム塩類を
反応させることにより製造することができるものである
。Next, the compound represented by the above formula [11] is prepared by the following formula [2
] It can be produced by reacting N-substituted-2-thiophenealdehyde amidinohydrazone/quaternary ammonium salts.
上記の式［１〕の化合物において、式中のＲのアルキル
基の例としては、メチル、エチル、プロピル、ブチル、
ペンチル、ヘキシルのような炭素数が０１〜Ｃ８のアル
キル基（ｎ−，１ｓｏ−などの全ての異性体を含む、）
を例示することができる１式［１〕中のｍは０．５〜１
．５が好ましく、より好ましくは約１である。In the compound of formula [1] above, examples of the alkyl group for R in the formula include methyl, ethyl, propyl, butyl,
Alkyl groups having 01 to C8 carbon atoms such as pentyl and hexyl (including all isomers such as n- and 1so-)
m in formula [1] can be exemplified as 0.5 to 1
．． 5 is preferred, more preferably about 1.
また、式［２］中のＲは式［１］と同様にＣ１〜Ｃ・の
アルキル基であり、Ｘはハロゲンである。Further, R in formula [2] is a C1-C. alkyl group as in formula [1], and X is a halogen.
［合成方法］
上述したように、本発明に係る式［１］の新規化合物で
あるＮ−置換−２−チオフェンアルデヒドアミジノヒド
ラゾン・Ｔ ＣＮ Ｑｆｉ塩類は、式［２］のＮ−置換
−２−チオフェンアルデヒドアミジノヒドラゾン・第四
アンモニウム塩類を式［３］のＴＣＮＱに反応させるこ
とによって容易に好ましい収率で製造することができる
。以下に１代表例としてＮ−置換−２−チオフェンアル
デヒドアミジノヒドラゾンＴＣＮＱ錯塩の製造方法につ
いて述べる。[Synthesis method] As described above, the N-substituted-2-thiophenealdehyde amidinohydrazone T CN Qfi salts, which are the novel compounds of the formula [1] according to the present invention, are the N-substituted-2- It can be easily produced in a preferred yield by reacting a thiophene aldehyde amidinohydrazone/quaternary ammonium salt with TCNQ of formula [3]. A method for producing N-substituted-2-thiophenealdehyde amidinohydrazone TCNQ complex salt will be described below as a representative example.
式［２］のＮ−置換−２−チオフェンアルデヒドアミジ
ノヒドラゾン・第四アンモニウム塩類は既に公知の化合
物であって、２−チオフェンアルデヒドアミジノヒドラ
ゾンからそれ自体公知の手法を利用して容易に合成する
ことができる。このＮ−置換−２−チオフェンアルデヒ
ドアミジノヒドラゾン・第四アンモニウム塩類の合成例
を第１表に示す、２−チオフェンアルデヒドアミジノヒ
ドラゾンを１とした場合の反応モル比は１：１〜３が好
ましく、本例では１：１．５とした。The N-substituted-2-thiophenealdehyde amidinohydrazone/quaternary ammonium salt of formula [2] is an already known compound, and can be easily synthesized from 2-thiophenealdehyde amidinohydrazone using a method known per se. Can be done. Synthesis examples of this N-substituted-2-thiophenealdehyde amidinohydrazone/quaternary ammonium salts are shown in Table 1. When 2-thiophenealdehyde amidinohydrazone is 1, the reaction molar ratio is preferably 1:1 to 3. In this example, the ratio was set to 1:1.5.
第１表 Ｎ−置換−２−チオフェンアルデヒドアミジノ
ヒドラゾン・第四アンモニウム塩類の合成例
式［３］のＴＣＮＱおよびその種々の塩ならびにその製
造方法についても既に公知であって、例えばり、Ｒ，Ｍ
ａｌｂｙらの、Ｊ、Ａｍ、Ｃｈｅｍ、Ｓｏｃ、、８４．
３３７４ （１９６２）および昭和５８年特許出願公開
第１９１４１４号公報に明示されている。Table 1 Synthesis examples of N-substituted-2-thiophenealdehyde amidinohydrazone/quaternary ammonium salts TCNQ of formula [3] and various salts thereof and methods for producing the same are already known.
Alby et al., J. Am. Chem. Soc., 84.
No. 3374 (1962) and Patent Application Publication No. 191414 of 1988.
次に、式［２］の化合物と式［３］のＴＣＮＱとから式
［１］の化合物を製造する一態様について詳述すると、
例えば式［２］中の一例としてのＮ−メチル−２−チオ
フェンアルデヒドアミジノヒドラゾン・第四アンモニウ
ム塩類の熱アセトニトリル溶液と式［３］のＴＣＮＱの
熱アセトニトリル溶液を熱時混合した後に放冷し、析出
した結晶を濾過する。この際１反応溶液に大過剰のエー
テルを注加し、反応生成物を析出せしめても良い１反応
生成物は熱アセトニトリルで再結晶するか、または冷無
水エタノールで同エタノールの着色が無くなるまで洗浄
すれば、無機塩類を含有しない式［１］中の一例として
のＮ−メチル−２−チオフェンアルデヒドアミジノヒド
ラゾン・ＴＣＮＱＣＮ上高収率で得ることができる。Next, one embodiment of producing the compound of formula [1] from the compound of formula [2] and TCNQ of formula [3] will be described in detail,
For example, a hot acetonitrile solution of N-methyl-2-thiophenealdehyde amidinohydrazone/quaternary ammonium salt as an example of formula [2] and a hot acetonitrile solution of TCNQ of formula [3] are mixed while hot, and then allowed to cool, The precipitated crystals are filtered. At this time, a large excess of ether may be added to the reaction solution to precipitate the reaction product.1 The reaction product may be recrystallized with hot acetonitrile or washed with cold absolute ethanol until the coloring of the same ethanol disappears. Then, N-methyl-2-thiophenealdehyde amidinohydrazone TCNQCN as an example of formula [1] containing no inorganic salts can be obtained in high yield.
ところで、式［２］の化合物と式［３］のＴＣＮＱとの
反応において、同反応は例えば常圧下。By the way, in the reaction between the compound of formula [2] and TCNQ of formula [3], the reaction is carried out, for example, under normal pressure.
好ましくは窒素ガス、アルゴンガスのような不活性ガス
雰囲気中で、アセトニトリル、ジメチルホルムアミド、
テトラヒｙロフラン、アルキルセロソルブなと、あるい
はそれらの適当な混合物のような不活性有機溶媒の沸点
下で行なうと良い０反応に使用する式［３］のＴＣＮＱ
の使用量は、式［２］の混合物１モルに対して約１〜３
モルの如き使用量を例示することができる。また、不活
性有機溶媒の使用量も適宜選択することができ、式［２
］の化合物に対して約１０〜２０倍、式［３］のＴＣＮ
Ｑに対して約５０〜１２０倍の如き使用量を例示するこ
とができる。Preferably in an inert gas atmosphere such as nitrogen gas or argon gas, acetonitrile, dimethylformamide,
TCNQ of formula [3] used in the reaction, which is preferably carried out at the boiling point of an inert organic solvent such as tetrahydrofuran, alkyl cellosolve, or a suitable mixture thereof.
The amount used is about 1 to 3 per mole of the mixture of formula [2].
Examples include amounts used in moles. Furthermore, the amount of the inert organic solvent to be used can be selected as appropriate, and the formula [2
] about 10 to 20 times as much as TCN of formula [3]
For example, the usage amount may be about 50 to 120 times that of Q.
［実施例］
ＮＱ錯塩類の具体的な合成方法の実施例について述べる
。[Example] An example of a specific method for synthesizing NQ complex salts will be described.
実施例Ｉ
Ｎ−メチル−２−チオフェンアルデヒドアミジノヒドラ
ゾン・第四アンモニウム・ＴＣＮＱＣＮ上合成について
述べる。Example I The synthesis of N-methyl-2-thiophenealdehyde amidinohydrazone/quaternary ammonium/TCNQCN is described.
Ｎ−メチル−２−チオフェンアルデヒドアミジノヒドラ
ゾン・第四アンモニウム・沃化水素酸塩０．００２５モ
ルをアセトニトリル８０ｍ１に熱時溶解し、これにＴＣ
ＮＱｏ、００２５モルをアセトニトリル３５ｍ１に熱時
溶解して注加し、混合し、さらに３０分間還流した。そ
の後、約１０時間、５℃に放置する。析出した結晶を濾
過した後、アセトニトリル、メタノール、エーテルの順
で洗浄し、アセトニトリルにより２回再結晶を行なった
。これをさらに乾燥させると、Ｎ−メチル−２−チオフ
ェンアルデヒドアミジノヒドラゾン・第四アンモニウム
・ＴＣＮＣＩ塩、融点２１７〜２１９℃の針状結晶を収
率９１％の高収率で得ることができる。0.0025 mol of N-methyl-2-thiophenealdehyde amidinohydrazone quaternary ammonium hydroiodide was dissolved in 80 ml of acetonitrile under heating, and TC
0025 mol of NQo, dissolved in 35 ml of acetonitrile while hot, was added, mixed and refluxed for a further 30 minutes. Thereafter, it is left at 5° C. for about 10 hours. After filtering the precipitated crystals, they were washed with acetonitrile, methanol, and ether in this order, and recrystallized twice with acetonitrile. When this is further dried, needle-like crystals of N-methyl-2-thiophenealdehyde amidinohydrazone/quaternary ammonium/TCNCI salt with a melting point of 217 to 219°C can be obtained in a high yield of 91%.
実施例２〜３
上記実施例１ではＮ−メチル−２−チオフェンアルデヒ
ドアミジノヒドラゾン・第四アンモニウム・ＴＣＮＱ錯
塩の合成について述べたが、式［２］中の化合物Ｒがエ
チルに置換された化合物（前掲第１表中２）、Ｒがｎ−
プロピルに置換された化合物（前掲第１表中３）をそれ
ぞれ用い、実施例１と同様の手法・手順に準じて合成し
た結果、第２表に示すようにＮ−エチル−２−チオフェ
ンアルデヒドアミジノヒドラゾン・第四アンモニウム−
ＴＣＮＱ錯塩（実施例２）、Ｎ−ｎ−プロピル−２−チ
オフェンアルデヒドアミジノヒドラゾン・第四アンモニ
ウム・ＴＣＮＱＩ塩（実施例３）を得た。Examples 2 to 3 In Example 1 above, the synthesis of N-methyl-2-thiophenealdehyde amidinohydrazone/quaternary ammonium/TCNQ complex salt was described. 2) in Table 1 above, R is n-
As a result of synthesis according to the same method and procedure as in Example 1 using each of the propyl-substituted compounds (3 in Table 1 above), as shown in Table 2, N-ethyl-2-thiophenealdehyde amidino Hydrazone/quaternary ammonium
A TCNQ complex salt (Example 2) and an Nn-propyl-2-thiophenealdehyde amidinohydrazone/quaternary ammonium/TCNQI salt (Example 3) were obtained.
［応用例］
上述のようにして得た式［１］のＮ−置換−２−チオフ
ェンアルデヒドアミジノヒドラゾン・ＴＣＮＱＣＮ類の
用途について述べると、このＴＣＮＱＣＮ類は例えば２
枚のアルミニウム箔をセパレータを介して巻回したコン
デンサ素子からなる固体電解コンデンサの固体電解質と
して、あるいはタンタル粉末焼結体のコンデンサ素子か
らなる固体電解コンデンサの固体電解質として利用し得
るものである。[Application example] To describe the use of the N-substituted-2-thiophenealdehyde amidinohydrazone/TCNQCN of formula [1] obtained as described above, this TCNQCN can be used, for example, in 2
It can be used as the solid electrolyte of a solid electrolytic capacitor consisting of a capacitor element formed by winding sheets of aluminum foil with a separator in between, or as the solid electrolyte of a solid electrolytic capacitor consisting of a capacitor element of tantalum powder sintered body.
Claims (2)
フェンアルデヒドアミジノヒドラゾン・７，７，８，８
−テトラシアノキノジメタン錯塩類。 ▲数式、化学式、表等があります▼［１］ 式［１］中、ＲはＣ＿１〜Ｃ＿６のアルキル基を示す。 ｍは１モルの錯塩に含まれる中性７，７，８，８−テト
ラシアノキノジメタンのモル数に対応する正の数（０．
５〜１．５）を意味する。(1) N-substituted-2-thiophenealdehyde amidinohydrazone 7,7,8,8 represented by the following formula [1]
- Tetracyanoquinodimethane complex salts. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [1] In formula [1], R represents an alkyl group of C_1 to C_6. m is a positive number (0.
5 to 1.5).
フェンアルデヒドアミジノヒドラゾン・第四アンモニウ
ム塩類を ▲数式、化学式、表等があります▼［２］ 下記の式［３］で表わされる７，７，８，８−テトラシ
アノキノジメタンと反応させ、 ▲数式、化学式、表等があります▼［３］ 下記の式［１］で表わされるＮ−置換−２−チオフェン
アルデヒドアミジノヒドラゾン・７，７，８，８−テト
ラシアノキノジメタン錯塩類を▲数式、化学式、表等が
あります▼［１］ 得ることを特徴としたＮ−置換−２−チオフェンアルデ
ヒドアミジノヒドラゾン・７，７，８，８−テトラシア
ノキノジメタン錯塩類の製造方法。 式［２］中、Ｘはハロゲンを示す。 式［１］中、ｍは１モルの錯塩に含まれる中性７，７，
８，８−テトラシアノキノジメタンのモル数に対応する
正の数（０．５〜１．５）を意味する。 式［１］および式［２］中、ＲはＣ＿１〜Ｃ＿６のアル
キル基を示す。(2) N-substituted-2-thiophenealdehyde amidinohydrazone/quaternary ammonium salts represented by the following formula [2] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [2] Represented by the following formula [3] By reacting with 7,7,8,8-tetracyanoquinodimethane, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [3] N-substituted-2-thiophenealdehyde amidinohydrazone represented by the following formula [1] 7,7,8,8-tetracyanoquinodimethane complex salts ▲Mathematical formulas, chemical formulas, tables, etc.▼[1] N-substituted-2-thiophenealdehyde amidinohydrazone 7,7, A method for producing 8,8-tetracyanoquinodimethane complex salts. In formula [2], X represents halogen. In formula [1], m is neutral 7,7, contained in 1 mol of complex salt.
It means a positive number (0.5 to 1.5) corresponding to the number of moles of 8,8-tetracyanoquinodimethane. In formula [1] and formula [2], R represents an alkyl group of C_1 to C_6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3584589A JPH02215753A (en) | 1989-02-15 | 1989-02-15 | N-substituted-2-thiophenealdehyde amidinohydrazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3584589A JPH02215753A (en) | 1989-02-15 | 1989-02-15 | N-substituted-2-thiophenealdehyde amidinohydrazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02215753A true JPH02215753A (en) | 1990-08-28 |
Family
ID=12453327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3584589A Pending JPH02215753A (en) | 1989-02-15 | 1989-02-15 | N-substituted-2-thiophenealdehyde amidinohydrazone-7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02215753A (en) |
-
1989
- 1989-02-15 JP JP3584589A patent/JPH02215753A/en active Pending
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