JPH02275862A - N-substituted-imidazole 7,7,8,8-tetracyanoquinodimethane complexes and its production - Google Patents
N-substituted-imidazole 7,7,8,8-tetracyanoquinodimethane complexes and its productionInfo
- Publication number
- JPH02275862A JPH02275862A JP9723189A JP9723189A JPH02275862A JP H02275862 A JPH02275862 A JP H02275862A JP 9723189 A JP9723189 A JP 9723189A JP 9723189 A JP9723189 A JP 9723189A JP H02275862 A JPH02275862 A JP H02275862A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- imidazole
- tetracyanoquinodimethane
- substituted
- complex
- 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
- -1 N-substituted-imidazole 7,7,8,8-tetracyanoquinodimethane complexes Chemical class 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 230000007935 neutral effect Effects 0.000 claims abstract description 4
- 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 6
- 150000003839 salts Chemical class 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 27
- 150000001875 compounds Chemical class 0.000 abstract description 16
- 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 abstract description 15
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract description 8
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 239000004065 semiconductor Substances 0.000 abstract description 4
- 239000007784 solid electrolyte Substances 0.000 abstract description 4
- 239000004020 conductor Substances 0.000 abstract description 3
- 239000012776 electronic material Substances 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 2
- 239000007789 gas Substances 0.000 abstract description 2
- 239000011261 inert gas Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method 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
- 238000006243 chemical reaction Methods 0.000 description 4
- 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
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical compound C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 description 1
- IWDFHWZHHOSSGR-UHFFFAOYSA-N 1-ethylimidazole Chemical compound CCN1C=CN=C1 IWDFHWZHHOSSGR-UHFFFAOYSA-N 0.000 description 1
- IYVYLVCVXXCYRI-UHFFFAOYSA-N 1-propylimidazole Chemical compound CCCN1C=CN=C1 IYVYLVCVXXCYRI-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([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
- 238000006467 substitution reaction Methods 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
- 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−イミダゾー
ル・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 [Industrial Application Field] 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 equipment or electronic materials. The present invention relates to imidazole/7.7.8.8-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−イミダゾール・
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-imidazole as a novel organic semiconductor (new compound) represented by the following formula [1]
7.7.8.8-Tetracyanoquinodimethane complex salts and a method for producing the same are provided.
ただし、式［１］中、ＲはＣ０〜Ｃ＋ａのアルキル基ま
たはベンジル基を示す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＠（０，５〜１．５）を意味する。However, in formula [1], R represents an alkyl group or a benzyl group of C0 to C+a, and 0m corresponds to the number of moles of neutral 7.7.8.8-tetracyanoquinodimethane contained in 1 mole of the complex salt. It means a positive @ (0,5 to 1.5).
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［１Ｆで示した化合物は、下記の式［２
］で表わされるＮ−置換−イミダゾール・第四アンモニ
ウム塩類を
下記の式［３］で表わされるＴＣＮＱと反応させること
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 [1F] is the compound represented by the following formula [2
] It can be produced by reacting the N-substituted-imidazole quaternary ammonium salt represented by the following formula [3] with TCNQ represented by the following formula [3].
上記の式［１］の化合物において１式中のＨ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〜Ｃ１］１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。また、式［１］中のＲと
してベンジル基を例示することができる０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。さらに１式［２］中のＲは式［１］と同様にＣ３
〜Ｃ＋ａのアルキル基またはベンジル基であり、Ｘはハ
ロゲンである。In the compound of formula [1] above, examples of the alkyl group of H in formula 1 include methyl, ethyl, propyl, butyl,
Examples include alkyl groups having 01 to C1]1 carbon atoms such as pentyl and hexyl (including all isomers such as n- and 1so-). Furthermore, m in formula [1], which can be exemplified by a benzyl group as R in formula [1], is preferably 0.5 to 1.5, more preferably about 1. Furthermore, R in Formula 1 [2] is C3 as in Formula [1].
~C+a is an alkyl group or a benzyl group, 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−イミダゾール・ＴＣＮＱＣＮ類は、式［
２］のＮ−置換−イミダゾール・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、代表例
としてＮ−置換−イミダゾール、Ｔ ＣＮ Ｑ錯塩類の
製造方法について述べる。[Synthesis method] As described above, the N-substituted-imidazole TCNQCN, which is a novel compound of formula [1] according to the present invention, has the formula [
It can be easily produced in a preferable yield by reacting the N-substituted-imidazole quaternary ammonium salt of formula [2] with TCNQ of formula [3]. A method for producing N-substituted imidazole and T CN Q complex salts will be described below as a representative example.
式［２］のＮ−置換−イミダゾール・第四アンモニウム
塩類は既に公知の化合物であって、イミダゾールからそ
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。The N-substituted-imidazole quaternary ammonium salt of formula [2] is a known compound and can be easily synthesized from imidazole using a method known per se.
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
ｅｌｂｙらのＪ、Ａｍ、Ｃｈｅｍ、Ｓｏｃ、、８４．３
３７４ （１９６２）ｉ５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。TCNQ of formula [3] and various salts thereof and methods for producing the same are already known, for example, R, M
J, Am, Chem, Soc, 84.3 of elby et al.
No. 374 (1962) i5 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１
例えば式［２］中の一例としてめＮ−メチル−イミダゾ
ール・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、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０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−メチルーイミグゾール・Ｔ
ＣＮＱ錯塩を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, as an example of formula [2], a hot acetonitrile solution of N-methyl-imidazole quaternary ammonium salt and a hot acetonitrile solution of TCNQ of formula [3] are mixed at a hot temperature, then allowed to cool, and the precipitated crystals are filtered. do. At this time, a large excess of ether may be added to the reaction solution to precipitate the reaction product.The reaction product may be recrystallized with hot acetonitrile or washed with cold absolute ethanol until the ethanol color disappears. Then, N-methyl-imigusol T as an example in formula [1] that does not contain inorganic salts
CNQ complex salt can be obtained in high yield.
ところで１式［２］の化合物と式［３］のＴＣＮ−〇と
の反応において、同反応は例えば常圧下、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、テトラヒドロ
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ＴＣＮＱ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。By the way, in the reaction between the compound of formula [2] and TCN-○ of formula [3], the reaction is carried out, for example, under normal pressure, preferably in an inert gas atmosphere such as nitrogen gas or argon gas.
The amount of TCNQ of formula [3] used in the reaction is preferably carried out at the boiling point of an inert organic solvent such as acetonitrile, dimethylformamide, tetrahydrofuran, alkyl cellosolve, or a suitable mixture thereof.
An example of the amount used is about 1 to 3 moles per mole of the mixture of formula [2]. Further, the amount of the inert organic solvent to be used can be appropriately selected, such as about 10 to 20 times the amount of the compound of formula [2] and about 50 to 120 times the amount of TCNQ of formula [3]. can be exemplified.
［実施例］
更に、本発明に係る式［１］のＮ−置換−イミダゾール
・ＴＣＮＱＩ塩類の具体的な合成方法の実施例について
述べる。[Example] Further, an example of a specific method for synthesizing the N-substituted-imidazole/TCNQI salt of formula [1] according to the present invention will be described.
実施例１
Ｎ−メチル−イミダゾール・第四アンモニウム・ＴＣＮ
Ｑ錯塩の合成について述べる。Example 1 N-methyl-imidazole/quaternary ammonium/TCN
The synthesis of Q complex salt will be described.
Ｎ−メチル−イミダゾール・第四アンモニウム・沃化水
素酸塩０．００４７モルをアセトニトリル２０ｍ１に熱
時溶解し、これにＴＣＮＱｏ。0.0047 mol of N-methyl-imidazole quaternary ammonium hydroiodide was dissolved in 20 ml of acetonitrile under hot conditions, and TCNQo was added to the solution.
００４７モルをアセトニトリル６５ｍ１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−イミダゾール・第四
アンモニウム・ＴＣＮＱ錯塩、融点２３６〜２３８℃の
針状結晶を収率７９％の高収率で得ることができる。0047 mol was dissolved in 65 ml of acetonitrile while hot and added, mixed and refluxed for an additional 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-imidazole/quaternary ammonium/TCNQ complex salt with a melting point of 236 to 238°C can be obtained in a high yield of 79%.
実施例２〜５
上記実施例１ではＮ−メチル−イミダゾール・第四アン
モニウム・Ｔ ＣＮ Ｑ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、Ｒ
がｎ−プロピルに置換された化合物、Ｒがｎ−ブチルに
置換された化合物、Ｒがベンジルに置換された化合物を
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１表に示すようにＮ−エチル−イミダゾ
ール・第四アンモニウム・ＴＣＮＱ錯塩（実施例２）、
Ｎ−ｎ−プロピル−イミダゾール・第四アンモニウム・
ＴＣＮＱ錯塩（実施例３）、Ｎ−ｎ−プチルーイミダゾ
ール・第四アンモニウム・ＴＣＮＱ錯塩（実施例４）、
Ｎ−ベンジル−イミダゾール・第四アンモニウム・Ｔ
ＣＮ Ｑ ｆａ塩（実施例５）を得た。Examples 2 to 5 In Example 1 above, the synthesis of N-methyl-imidazole/quaternary ammonium/TCNQ complex salt was described.
A compound in which compound R in formula [2] is substituted with ethyl, R
As a result of synthesis according to the same method and procedure as in Example 1 using a compound in which R was substituted with n-propyl, a compound in which R was substituted with n-butyl, and a compound in which R was substituted with benzyl, As shown in Table 1, N-ethyl-imidazole/quaternary ammonium/TCNQ complex salt (Example 2),
N-n-propyl-imidazole/quaternary ammonium/
TCNQ complex salt (Example 3), N-n-butyroimidazole/quaternary ammonium/TCNQ complex salt (Example 4),
N-benzyl-imidazole/quaternary ammonium/T
CN Q fa salt (Example 5) was obtained.
［応用例］上述のようにして得た式［１］のＮ−置換−
イミダゾール・ＴＣＮＱＣＮ類の用途について述べると
、このＴ ＣＮ Ｑｉｌ塩類は例えば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] N-substitution of formula [1] obtained as described above
Regarding the uses of imidazole/TCNQCN, these TCN Qil salts can be used, for example, as a solid electrolyte in a solid electrolytic capacitor consisting of a capacitor element formed by winding two sheets of aluminum foil with a separator in between, or as a solid electrolyte in a tantalum powder sintered capacitor. It can be used as a solid electrolyte for solid electrolytic capacitors consisting of elements.
Claims (2)
ール・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＿１＿８のアルキル基また
はベンジル基を示す。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-imidazole/7,7,8,8-tetracyanoquinodimethane complex salts represented by the following formula [1]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [1] In formula [1], R represents an alkyl group of C_1 to C_1_8 or a benzyl group. m means a positive number (0.5 to 1.5) corresponding to the number of moles of neutral 7,7,8,8-tetracyanoquinodimethane contained in 1 mole of complex salt.
ール・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−イミダゾール・
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−イミダゾール・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＿１＿８の
アルキル基またはベンジル基を示す。(2) N-substituted-imidazole quaternary ammonium salts represented by the following formula [2] ▲ There are numerical formulas, chemical formulas, tables, etc. ▼ [2] 7, 7, 8 represented by the following formula [3] , 8-tetracyanoquinodimethane, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [3] N-substituted-imidazole represented by the following formula [1]
7,7,8,8-tetracyanoquinodimethane complex salts ▲Mathematical formulas, chemical formulas, tables, etc.▼[1] N-substituted-imidazole 7,7 characterized by obtaining 7,7,8,8-tetracyanoquinodimethane complex salts
, 8,8-tetracyanoquinodimethane complex salt production method. 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_1_8 or a benzyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9723189A JPH02275862A (en) | 1989-04-17 | 1989-04-17 | N-substituted-imidazole 7,7,8,8-tetracyanoquinodimethane complexes and its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9723189A JPH02275862A (en) | 1989-04-17 | 1989-04-17 | N-substituted-imidazole 7,7,8,8-tetracyanoquinodimethane complexes and its production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02275862A true JPH02275862A (en) | 1990-11-09 |
Family
ID=14186851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9723189A Pending JPH02275862A (en) | 1989-04-17 | 1989-04-17 | N-substituted-imidazole 7,7,8,8-tetracyanoquinodimethane complexes and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02275862A (en) |
-
1989
- 1989-04-17 JP JP9723189A patent/JPH02275862A/en active Pending
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