JPH02282369A - N-substituted-benzimidazole 7,7,8,8-tetracyanoquinodimethane complex and its production - Google Patents
N-substituted-benzimidazole 7,7,8,8-tetracyanoquinodimethane complex and its productionInfo
- Publication number
- JPH02282369A JPH02282369A JP10411789A JP10411789A JPH02282369A JP H02282369 A JPH02282369 A JP H02282369A JP 10411789 A JP10411789 A JP 10411789A JP 10411789 A JP10411789 A JP 10411789A JP H02282369 A JPH02282369 A JP H02282369A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- benzimidazole
- tetracyanoquinodimethane
- substituted
- quaternary ammonium
- 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-benzimidazole Chemical class 0.000 title claims abstract description 13
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 title claims abstract 9
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 230000007935 neutral effect Effects 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 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
- 239000000463 material Substances 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 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 13
- 238000000034 method Methods 0.000 description 6
- FGYADSCZTQOAFK-UHFFFAOYSA-N 1-methylbenzimidazole Chemical compound C1=CC=C2N(C)C=NC2=C1 FGYADSCZTQOAFK-UHFFFAOYSA-N 0.000 description 5
- 125000001453 quaternary ammonium group Chemical group 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
- 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
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007784 solid electrolyte Substances 0.000 description 2
- MNEIJGDSFRHGMS-UHFFFAOYSA-N 1-(phenylmethyl)benzimidazole Chemical compound C1=NC2=CC=CC=C2N1CC1=CC=CC=C1 MNEIJGDSFRHGMS-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
- 238000004040 coloring Methods 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
- 239000007789 gas Substances 0.000 description 1
- 150000002367 halogens Chemical group 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
- 239000011261 inert gas Substances 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
- 239000003960 organic solvent Substances 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
- 238000010992 reflux 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
- 125000003944 tolyl group Chemical group 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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−ベンゾイミ
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 [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. The present invention relates to benzimidazole/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−ベンゾイミダゾ
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-benzimidazole 7.7.8.8-tetracyanoquinodimethane complex salts as a novel organic semiconductor (new compound) represented by the following formula [1] and The present invention provides a method for manufacturing the same.
ただし、式「１コ中、ＲはＣ，−Ｃ，、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。However, in the formula "1, R represents an alkyl group or a benzyl group of C, -C,. m is neutral 7.7°8,8-tetracyanoquinodimethane contained in 1 mol of the complex salt. It means a positive number (0.5 to 1.5) corresponding to the number of moles.
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６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−ベンゾイミダゾール・第四アンモニウム塩類を
である。For convenience of explanation, 7,7.8.8-tetracyanoquinodimethane, hereinafter referred to as TCNQ, is expressed by the above formula [
The compound shown in 11 is N represented by the following formula [2]
-Substituted-benzimidazole quaternary ammonium salts.
上記の式［１］の化合物において１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〜ＣＩ８のア
ルキル基（ｎ−，１ｓｏ−などの全ての異性体を含む。Examples of the alkyl group of R in formula 1 in the compound of formula [1] above include methyl, ethyl, propyl, butyl,
Alkyl groups having 01 to CI8 carbon atoms such as pentyl and hexyl (including all isomers such as n- and 1so-).
〕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。式［１］中のｍ
は０．５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り、Ｘはハロ
ゲンである。] can be exemplified. Moreover, a benzyl group can be exemplified as R in formula [1]. m in formula [1]
can be produced by reacting with TCNQ represented by the following formula [3], where 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−ベンゾイミダゾール・ＴＣＮＱＣＮ類は
、式［２コのＮ−置換−ベンゾイミダゾール・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−ベンゾイミダゾール、Ｔ
ＣＮＱ錯塩類の製造方法について述べる。[Synthesis method] As described above, the novel compounds of the formula [1] according to the present invention, N-substituted-benzimidazole TCNQCN, are synthesized from the N-substituted-benzimidazole quaternary ammonium salts of the formula [2]. It can be easily produced in a preferred yield by reacting with TCNQ of formula [3]. Below, as representative examples, N-substituted-benzimidazole, T
A method for producing CNQ complex salts will be described.
式「２」のＮ−置換−ベンシイミグゾール・第四アンモ
ニウム塩類は既に公知の化合物であって、ベンゾイミダ
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 benzimiguzole quaternary ammonium salt of formula "2" is a known compound and can be easily synthesized from benzimidazole using a method known per se.
式［３］のＴＣＮＱｊ３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，
Ｍｅｌｂｙ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−ベンゾイミダゾール・ＴＣＮＱ錯塩を
高収率で得ることができる。TCNQj3 of formula [3] and various salts thereof and methods for producing the same are already known, for example, R,
Melby et al., J. Am. Chem. Soc., 84.
3374 (1962) and Patent Application Publication No. 191414 of 1981. An example of formula [1] that does not contain inorganic salts if recrystallized with tolyl or washed with cold anhydrous ethanol until the coloring of the same ethanol disappears. N-methyl-benzimidazole/TCNQ complex salt can be obtained in high yield.
ところで、式［２］の化合物と式［３コのＴＣＮＱ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、ジメチルホて詳述すると、例えば式［２
］中の一例としてのＮ−メチル−ベンゾイミダゾール・
第四アンモニウム塩類の熱アセトニトリル溶液と式［３
１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。反応生成物は熱アセトニ応に使用する式［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［
３１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 TCNQ of formula [3], the reaction is carried out under normal pressure, preferably in an inert gas atmosphere such as nitrogen gas or argon gas, using acetonitrile or dimethyl chloride. Then, for example, the formula [2
] as an example of N-methyl-benzimidazole.
A hot acetonitrile solution of quaternary ammonium salts and the formula [3
A hot acetonitrile solution of TCNQ (1) is mixed while hot, then allowed to cool, and 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. The reaction product has the formula [3
] The amount of TCNQ used can be exemplified by about 1 to 3 mol per 1 mol of the mixture of formula [2]. Further, the amount of the inert organic solvent to be used can be selected as appropriate, and is about 10 to 20 times that of the compound of formula [2].
For example, the usage amount is about 50 to 120 times that of TCNQ of 31.
［実施例］
更に、本発明に係る式［１］のＮ−置換−ベンゾイミダ
ゾール・ＴＣＮＱＣＮ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-benzimidazole TCNQCN of formula [1] according to the present invention will be described.
実施例１
Ｎ−メチル−ベンゾイミダゾール・第四アンモニウム・
ＴＣＮＱｔＭ塩の合成について述べる。Example 1 N-methyl-benzimidazole quaternary ammonium
The synthesis of TCNQtM salt will be described.
Ｎ−メチル−ベンゾイミダゾール・第四アンモ上記実施
例１ではＮ−メチル−ベンゾイミダシル・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、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−ベンシイミグゾー
ル・第四アンモニウム・ＴＣＮＱ錯時溶解して注加し、
混合し、さらに３０分間還流した。その後、約１０時間
、５°Ｃ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−ベンゾイミダゾール・第四
アンモニウム・ＴＣＮＱ錯塩、融点２３１〜２３４℃の
針状結晶を収率８１％の高収率で得ることができる。N-Methyl-benzimidazole/quaternary ammo In Example 1 above, the synthesis of N-methyl-benzimidazole/quaternary ammonium/TCNQ complex salt was described, but the formula [2]
A compound in which R was substituted with ethyl, 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 were used, and Example 1 and As a result of synthesis according to the same method and procedure, as shown in Table 1, N-ethyl-benciimigsol/quaternary ammonium/TCNQ complex was dissolved and added,
Mix and reflux for an additional 30 minutes. It is then 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-benzimidazole/quaternary ammonium/TCNQ complex salt with a melting point of 231 to 234°C can be obtained in a high yield of 81%.
実施例２〜５
ル・第四アンモニウム・ＴＣＮＱ錯塩（実施例４〕、Ｎ
−ベンジル−ベンゾイミダゾール・第四アンモニウム・
Ｔ ＣＮ Ｑｉ塩（実施例５〕を得た。Examples 2 to 5 Quaternary ammonium TCNQ complex salt (Example 4), N
-Benzyl-benzimidazole/Quaternary ammonium/
T CN Qi salt (Example 5) was obtained.
［応用例］
上述のようにして得た式［１］のＮ−置換−ベンゾイミ
ダゾール・Ｔ ＣＮ Ｑ＠基塩類用途につｌ／Ｘで述べ
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] When describing the use of N-substituted-benzimidazole TCNQ@base salts of the formula [1] obtained as described above in terms of l/X, this TCNQCN type can be used, for example, by combining two sheets of aluminum foil. It can be used as a solid electrolyte in a solid electrolytic capacitor consisting of a capacitor element wound with a separator in between, or as a solid electrolyte in a solid electrolytic capacitor consisting of a capacitor element made of sintered tantalum powder.
Claims (2)
ミダゾール・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-benzimidazole/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.
ミダゾール・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−ベンゾイミダゾ
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−ベンゾイミダゾール・
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-benzimidazole quaternary ammonium salts represented by the following formula [2] ▲ mathematical formula, chemical formula,
There are tables, etc. ▼ [2] React with 7,7,8,8-tetracyanoquinodimethane represented by the following formula [3], ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [3] The following formula [1] N-substituted-benzimidazole 7,7,8,8-tetracyanoquinodimethane complex salts represented by ▲Mathematical formulas, chemical formulas, tables, etc. are available▼[1] N- Substituted-benzimidazole
A method for producing 7,7,8,8-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_1_8 or a benzyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10411789A JPH02282369A (en) | 1989-04-24 | 1989-04-24 | N-substituted-benzimidazole 7,7,8,8-tetracyanoquinodimethane complex and its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10411789A JPH02282369A (en) | 1989-04-24 | 1989-04-24 | N-substituted-benzimidazole 7,7,8,8-tetracyanoquinodimethane complex and its production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02282369A true JPH02282369A (en) | 1990-11-19 |
Family
ID=14372184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10411789A Pending JPH02282369A (en) | 1989-04-24 | 1989-04-24 | N-substituted-benzimidazole 7,7,8,8-tetracyanoquinodimethane complex and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02282369A (en) |
-
1989
- 1989-04-24 JP JP10411789A patent/JPH02282369A/en active Pending
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