JPH02282373A - N-substituted-1,2,3-benzotriazole 7,7,8,8-tetracyanoquinodimethane complex salts and production thereof - Google Patents
N-substituted-1,2,3-benzotriazole 7,7,8,8-tetracyanoquinodimethane complex salts and production thereofInfo
- Publication number
- JPH02282373A JPH02282373A JP10411889A JP10411889A JPH02282373A JP H02282373 A JPH02282373 A JP H02282373A JP 10411889 A JP10411889 A JP 10411889A JP 10411889 A JP10411889 A JP 10411889A JP H02282373 A JPH02282373 A JP H02282373A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- benzotriazole
- 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
- 150000003839 salts Chemical class 0.000 title claims abstract description 24
- -1 N-substituted-1,2,3-benzotriazole Chemical class 0.000 title claims abstract description 11
- 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 description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 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
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 239000012964 benzotriazole Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims 3
- 239000004065 semiconductor Substances 0.000 abstract description 4
- 239000012776 electronic material Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 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 15
- 150000001875 compounds Chemical class 0.000 description 15
- 125000001453 quaternary ammonium group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 238000006243 chemical 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
- 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
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000007784 solid electrolyte Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HXQHRUJXQJEGER-UHFFFAOYSA-N 1-methylbenzotriazole Chemical compound C1=CC=C2N(C)N=NC2=C1 HXQHRUJXQJEGER-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000004020 conductor 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
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OQVSPZZIBWDHOF-UHFFFAOYSA-N 1-benzylbenzotriazole Chemical compound N1=NC2=CC=CC=C2N1CC1=CC=CC=C1 OQVSPZZIBWDHOF-UHFFFAOYSA-N 0.000 description 1
- IDXCVQOKCGDSOR-UHFFFAOYSA-N 1-butylbenzotriazole Chemical compound C1=CC=C2N(CCCC)N=NC2=C1 IDXCVQOKCGDSOR-UHFFFAOYSA-N 0.000 description 1
- VGCWCUQMEWJQSU-UHFFFAOYSA-N 1-ethylbenzotriazole Chemical compound C1=CC=C2N(CC)N=NC2=C1 VGCWCUQMEWJQSU-UHFFFAOYSA-N 0.000 description 1
- KMHKYOIGRHFJBP-UHFFFAOYSA-N 1-propylbenzotriazole Chemical compound C1=CC=C2N(CCC)N=NC2=C1 KMHKYOIGRHFJBP-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 238000009835 boiling Methods 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
- 229910052799 carbon Inorganic materials 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
- 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
- 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
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−１，２，３
−ベンゾトリアゾール・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. 1, 2, 3
-Benzotriazole/7.7,8.8-tetracyanoquinodimethane complex salts and a method for producing the same.
［発明の概要コ
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１．２．３−ベン
ゾトリアゾール・７．７．８８−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 1,2,3-benzotriazole 7,7,88-tetracyanoquinodimethane as a novel organic semiconductor (new compound) represented by the following formula [1] The present invention provides complex salts and methods for producing the same.
ただし、式［１７中、ＲはＣ９〜ｃ１Ｂ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 formula [17, R represents a C9-c1B alkyl group 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.
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［１］で示した化合物は、下記の式［２
］で表わされるＮ−置換−１，２，３ベンゾトリアゾー
ル・第四アンモニウム塩類を下記の式［３ゴで表わされ
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 shown by the above formula [1] can be converted to the compound shown by the following formula [2].
It can be produced by reacting N-substituted-1,2,3 benzotriazole quaternary ammonium salts represented by the following formula [3] with TCNQ represented by the following formula.
上記の式［１］の化合物において、式中ＯＲ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Ｃ９〜ｃ１Ｂのア
ルキル基（ｎ−，１ｓｏ−などの全ての異性体を含む。In the compound of formula [1] above, examples of the alkyl group for OR in the formula include methyl, ethyl, propyl, butyl,
Alkyl groups having a carbon number of C9 to C1B, 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０．５〜１．５が好ましく、より好ましくは約１であ
る。さらに、式［２］中のＲは式［１］と同様に０１〜
Ｃ１８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。) can be exemplified. Moreover, a benzyl group can be exemplified as R in formula [1]. m in formula [1]
is preferably 0.5 to 1.5, more preferably about 1. Furthermore, R in formula [2] is 01 to 01 as in formula [1].
It is a C18 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−１，２，３−ベンゾトリアゾール・ＴＣ
ＮＱＣＮ類は、式［２］のＮ−置換−１，２，３−ベン
ゾトリアゾール・第四アンモニウム塩類を式［３］のＴ
ＣＮＱ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
−１゜２．３−ベンゾトリアゾール、ＴＣＮＱＣＮ類の
製造方法について述べる。[Synthesis method] As described above, the novel compound of formula [1] according to the present invention, N-substituted-1,2,3-benzotriazole TC
NQCNs are N-substituted-1,2,3-benzotriazole quaternary ammonium salts of formula [2] and T of formula [3].
It can be easily produced in a preferred yield by reacting with CNQ. Below, as a representative example, a method for producing N-substituted-1°2,3-benzotriazole and TCNQCN will be described.
式［２］のＮ−置換−１，２，３−ベンゾトリアゾール
・第四アンモニウム塩類は既に公知の化合物であって、
１．２．３−ベンゾトリア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-1,2,3-benzotriazole quaternary ammonium salts of formula [2] are already known compounds,
It can be easily synthesized from 1.2.3-benzotriazole 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）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。TCNQ of formula [3] and various salts thereof and methods for producing the same are already known, for example, R, M
Elby et al., J-Am, Chem, Soc, 84.3
No. 374 (1962) and Patent Application Publication No. 191414 of 1988.
次に、式［２］の化合物と式［３］ （７）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−１
，，２，３−ベンゾトリアゾール・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。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−１，２，３−ベンゾトリアゾール・ＴＣＮＱ
錯塩を高収率で得ることができる。Next, to explain in detail one aspect of producing the compound of formula [1] from the compound of formula [2] and formula [3] (7) TCNQ, for example, N-methyl- 1
,, A hot acetonitrile solution of a 2,3-benzotriazole quaternary ammonium salt and a hot acetonitrile solution of TCNQ of formula [3] are mixed while hot, and 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. If the reaction product is recrystallized with hot acetonitrile or washed with cold anhydrous ethanol until the coloring of the same ethanol disappears, N as an example of formula [1] containing no inorganic salts can be obtained.
-Methyl-1,2,3-benzotriazole・TCNQ
Complex 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、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。反応に使用する式［３］のＴＣＮＱの使用量は、式
［２コの混合物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］（７）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, for example, under normal pressure, preferably in an inert gas atmosphere such as nitrogen gas or argon gas, using acetonitrile, dimethylformamide, or tetrahydrofuran. The reaction is preferably carried out at the boiling point of an inert organic solvent such as alkyl cellosolve, or a suitable mixture thereof. The amount of TCNQ of formula [3] used in the reaction can be exemplified by 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 the compound of formula [3] (7) TCNQ. The usage amount can be exemplified.
［実施例］
更に、本発明に係る式［１］のＮ−置換−１゜２．３−
ベンゾトリアゾール・ＴＣＮＱＣＮ類の具体的な合成方
法の実施例について述べる。[Example] Furthermore, N-substituted-1゜2.3- of formula [1] according to the present invention
An example of a specific method for synthesizing benzotriazole/TCNQCN will be described.
実施例Ｉ
Ｎ−メチル−１，２，３−ベンゾトリアゾール・第四ア
ンモニウム・ＴＣＮＱ錯塩の合成について述べる。Example I The synthesis of N-methyl-1,2,3-benzotriazole/quaternary ammonium/TCNQ complex salt will be described.
Ｎ−メチル−１，２，３−ベンゾトリアゾール・第四ア
ンモニウム・沃化水素酸塩０．００４５モルをアセトニ
トリル２０ｍ１に熱時溶解し、これにＴＣＮＱｏ、００
６０モルをアセトニトリル６０ｍ１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−１，２゜３−ベンゾトリ
アゾール・第四アンモニウム・ＴＣＮＱ錯塩、融点２７
８〜２８２℃の針状結晶を収率６４％で得ることができ
る。0.0045 mol of N-methyl-1,2,3-benzotriazole quaternary ammonium hydroiodide was dissolved in 20 ml of acetonitrile while hot, and TCNQo, 00
A hot solution of 60 mol in 60 ml of acetonitrile was poured into the solution, mixed, and refluxed for an additional 30 minutes. After that, about 10
Leave at 5°C for an hour. 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, N-methyl-1,2゜3-benzotriazole/quaternary ammonium/TCNQ complex salt, melting point 27
Needle-shaped crystals having a temperature of 8 to 282°C can be obtained in a yield of 64%.
実施例２〜５
上記実施例１ではＮ−メチル−１，２，３−ベンゾトリ
アゾール・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−１，２，３−ベンゾトリアゾール・第四アンモニ
ウム・ＴＣＮＱ錯塩（実施例２）、Ｎ−ｎ−プロピル−
１，２，３−ベンゾトリアゾール・第四アンモニウム・
ＴＣＮＱ錯塩（実施例３）、Ｎ −ｎ−ブチル−１，２
，３−ベンゾトリアゾール・第四アンモニウム・ＴＣＮ
Ｑ錯塩（実施例４）、Ｎ−ベンジル−１，２，３−ベン
ゾトリアゾール・第四アンモニウム・ＴＣＮＱ錯塩（実
施例５）
を得た。Examples 2 to 5 In Example 1 above, the synthesis of N-methyl-1,2,3-benzotriazole/quaternary ammonium/TCNQ complex salt was described, but compound R in formula [2] was substituted with ethyl. Compound, R is substituted with n-propyl, R
The same method as in Example 1 was carried out using a compound in which R was substituted with n-butyl and a compound in which R was substituted with benzyl.
As a result of synthesis according to the procedure, as shown in Table 1, N-ethyl-1,2,3-benzotriazole/quaternary ammonium/TCNQ complex salt (Example 2), N-n-propyl-
1,2,3-benzotriazole・Quaternary ammonium・
TCNQ complex salt (Example 3), N-n-butyl-1,2
,3-benzotriazole/quaternary ammonium/TCN
Q complex salt (Example 4) and N-benzyl-1,2,3-benzotriazole/quaternary ammonium/TCNQ complex salt (Example 5) were obtained.
［応用例］
上述のようにして得た式［１］のＮ−置換１．２．３−
ベンゾトリアゾール・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] N-substitution 1.2.3- of formula [1] obtained as described above
Regarding the uses of benzotriazole/TCNQCN, for example, TCNQCN can be used as a solid electrolyte in a solid electrolytic capacitor consisting of a capacitor element formed by wrapping two sheets of aluminum foil with a separator in between, or as a solid electrolyte in a capacitor element made of tantalum powder sintered body. It can be used as a solid electrolyte for a solid electrolytic capacitor consisting of:
Claims (2)
３−ベンゾトリアゾール・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-1,2, represented by the following formula [1]
3-benzotriazole/7,7,8,8-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_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.
３−ベンゾトリアゾール・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−１，２，３−ベ
ンゾトリアゾール・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−１，２，３−ベンゾト
リアゾール・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-1,2, represented by the following formula [2]
3-benzotriazole quaternary ammonium salts are reacted with 7,7,8,8-tetracyanoquinodimethane represented by the following formula [3]. There are mathematical formulas, chemical formulas, tables, etc. ▼ [3] N-substituted-1,2,3-benzotriazole 7,7,8,8-tetracyanoquinodimethane complex salts represented by the following formula [1] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [1] Method for producing N-substituted-1,2,3-benzotriazole/7,7,8,8-tetracyanoquinodimethane complex salts characterized by obtaining . 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 |
|---|---|---|---|
| JP10411889A JPH02282373A (en) | 1989-04-24 | 1989-04-24 | N-substituted-1,2,3-benzotriazole 7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10411889A JPH02282373A (en) | 1989-04-24 | 1989-04-24 | N-substituted-1,2,3-benzotriazole 7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02282373A true JPH02282373A (en) | 1990-11-19 |
Family
ID=14372212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10411889A Pending JPH02282373A (en) | 1989-04-24 | 1989-04-24 | N-substituted-1,2,3-benzotriazole 7,7,8,8-tetracyanoquinodimethane complex salts and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02282373A (en) |
-
1989
- 1989-04-24 JP JP10411889A patent/JPH02282373A/en active Pending
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