JPS63295563A - N-substituted-phthalazine-7,7,8,8-tetracyanoquino-dimethane complex salts and production thereof - Google Patents
N-substituted-phthalazine-7,7,8,8-tetracyanoquino-dimethane complex salts and production thereofInfo
- Publication number
- JPS63295563A JPS63295563A JP3193987A JP3193987A JPS63295563A JP S63295563 A JPS63295563 A JP S63295563A JP 3193987 A JP3193987 A JP 3193987A JP 3193987 A JP3193987 A JP 3193987A JP S63295563 A JPS63295563 A JP S63295563A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- phthalazine
- substituted
- tetracyanoquinodimethane
- 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
- 150000003839 salts Chemical class 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 N-substituted- phthalazine Chemical class 0.000 claims abstract description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 230000007935 neutral effect Effects 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 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 7
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 33
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 8
- 239000013078 crystal Substances 0.000 abstract description 6
- 239000004065 semiconductor Substances 0.000 abstract description 4
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 239000004020 conductor Substances 0.000 abstract description 3
- 239000012776 electronic material Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 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 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- YISKQGXPHIESAR-UHFFFAOYSA-N 2-methyl-1h-phthalazine Chemical compound C1=CC=C2C=NN(C)CC2=C1 YISKQGXPHIESAR-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 239000003990 capacitor Substances 0.000 description 4
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 4
- 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
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 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
- CRUOBCRHFAKJHY-UHFFFAOYSA-N C1C2=CC=CC=C2C=NN1CC1=CC=CC=C1 Chemical compound C1C2=CC=CC=C2C=NN1CC1=CC=CC=C1 CRUOBCRHFAKJHY-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
- 238000001816 cooling Methods 0.000 description 1
- 239000011888 foil 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 239000002244 precipitate Substances 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
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
- H01G9/022—Electrolytes; Absorbents
- H01G9/025—Solid electrolytes
- H01G9/028—Organic semiconducting electrolytes, e.g. TCNQ
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (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−フタラジン
・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. This invention relates to phthalazine/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−フタラジン・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-phthalazine 7 as a novel organic semiconductor (new compound) represented by the following formula [1]
, 7,8.8-tetracyanoquinodimethane complex salts and a method for producing the same.
ただし、式［１］中、ＲはＣ１〜Ｃ６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 [1], R represents a C1-C6 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 the 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と祢す。For convenience of explanation, 7,7,8.8-tetracyanoquinodimethane will be referred to as TCNQ hereinafter.
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−フタラジン・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 shown by the above formula [1] can be converted to the compound shown by the following formula [2].
] It can be produced by reacting the N-substituted-phthalazine 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、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ＣＩＮＣＧ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。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 with carbon number CINCG such as pentyl and hexyl (including all isomers such as n-, 1so-, etc.)
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.
また、式［２］中のＲは式［１］と同様に６１〜０１％
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。Also, R in formula [2] is 61 to 01% as in formula [1].
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コの新規化合物で
あるＮ−置換−フタラジン・Ｔ ＣＮ Ｑ ３１塩類は
、式［２］のＮ−置換−フタラジン・第四アンモニウム
塩類を式［３コの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、そ
の製造方法について述べる。[Synthesis method] As described above, the novel compound N-substituted-phthalazine T CN Q 31 salts of formula [1] according to the present invention are N-substituted-phthalazine quaternary ammonium salts of formula [2] can be easily produced in a desirable yield by reacting TCNQ of formula [3]. The manufacturing method will be described below.
式［２］のＮ−置換−フタラジン・第四アンモニウム塩
類は既に公知の化合物であって、フタラジンからそれ自
体公知の手法を利用して容易に合成することができる。The N-substituted-phthalazine quaternary ammonium salt of formula [2] is a known compound and can be easily synthesized from phthalazine using a method known per se.
このＮ−置換−フタラジン・第四アンモニウム塩類の合
成例を第１表に示す。フタラジンを１とした場合の反応
モル比はに１〜３が好ましく、本例では１：１．５とし
た。Synthesis examples of this N-substituted-phthalazine quaternary ammonium salt are shown in Table 1. The reaction molar ratio when phthalazine is 1 is preferably 1 to 3, and in this example it was 1:1.5.
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
J, Am, Chem, Soc, 84.3 of elby et al.
No. 374 (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−フタラジ
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、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−フタラジン・ＴＣ
ＮＱ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, a hot acetonitrile solution of N-methyl-phthalazine/quaternary ammonium salt as an example of formula [2] and a hot acetonitrile solution of TCNQ of formula [3] are mixed while hot, 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 can be recrystallized with hot acetonitrile or washed with cold anhydrous ethanol until the coloring of the same ethanol disappears, resulting in a formula [
1] N-methyl-phthalazine TC as an example of
NQ complex salt 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９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］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５
０〜１２０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 9 gas or argon gas, using acetonitrile, dimethylformamide, This 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 of TCNQ of formula [3] used in the reaction may be 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, and is about 10 to 20 times the amount of the compound of formula [2], and about 5 times the amount of TCNQ of the formula [3].
An example of the usage amount is 0 to 120 times.
し実施例コ
更に、本発明に係る式［１］のＮ−置換−フタラジン・
ＴＣＮＱＣＮ類の具体的な合成方法の実施例について述
べる。Furthermore, in Examples, N-substituted-phthalazine of formula [1] according to the present invention
An example of a specific method for synthesizing TCNQCNs will be described.
実施例Ｉ
Ｎ−メチル−フタラジン・第四アンモニウム・ＴＣＮＱ
錯塩の合成について述べる。Example I N-methyl-phthalazine quaternary ammonium TCNQ
The synthesis of complex salts will be described.
Ｎ−メチル−フタラジン・第四アンモニウム・沃化水素
酸塩ｏ、ｏｔｏｏモルをアセトニトリル５０ｍ１に熱時
溶解し、こわにＴＣＮＱｏ、０１５モルをアセトニトリ
ル３００ｍ１に熱時溶解して注加し、混合した後に室温
で約５時間放冷する。場合によってはこの放冷後に大過
剰のエーテルを加えて完全に結晶を析出させ、析出した
黒色針状結晶を濾別する。この結晶を熱アセトニトリル
により再結晶を繰返し行ない、場合によっては引続きエ
タノールで同濾液が着色しなくなるまで洗浄した後、エ
ーテルで洗浄し、さらに乾燥させると、沃素イオンを全
く含有しない純粋なＮ−メチル−７タラジン・第四アン
モニウム・ＴＣＮＱ錯塩、融点２７４〜２７９℃の黒色
針状結晶を収率８５％の高収率で得ることができる。O, too moles of N-methyl-phthalazine quaternary ammonium hydroiodide were dissolved in 50 ml of acetonitrile, and then 0.15 mol of TCNQo was dissolved in 300 ml of acetonitrile and poured into the solution, and after mixing. Leave to cool at room temperature for about 5 hours. In some cases, after this cooling, a large excess of ether is added to completely precipitate the crystals, and the precipitated black needle crystals are filtered off. The crystals are repeatedly recrystallized using hot acetonitrile, and in some cases, the filtrate is washed with ethanol until the filtrate is no longer colored, then washed with ether, and further dried to obtain pure N-methyl containing no iodide ions. -7 Talazine/quaternary ammonium/TCNQ complex salt, black needle-shaped crystals having a melting point of 274 to 279°C can be obtained in a high yield of 85%.
実施例２〜６
Ｌ記実施例１ではＮ−メチル−フタラジン・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、ｎ−プロピル、ｎ−ブチル、
ｎ−ヘキシルおよびベンジルに置換された式［２］の化
合物（前掲第１表中２〜６）を用い、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−フタラジン・第四アンモニウム・ＴＣＮＱ
錯塩（実施例２）、Ｎ−プロピル−フタラジン・第四ア
ンモニウム・ＴＣＮＱ錯塩（実施例３）、Ｎ−ブチル−
フタラジン・第四アンモニウム・ＴＣＮＣＩ塩（実施例
４）、Ｎ−へキシル−フタラジン・第四アンモニウム・
ＴＣＮＱ錯塩（実施例５）、Ｎ−ベンジル−フタラジン
・第四アンモニラム・ＴＣＮＱ錯塩（実施例６）を得た
。Examples 2 to 6 In Example 1, the synthesis of N-methyl-phthalazine/quaternary ammonium/TCNQ complex salt was described.
], where the compound R is ethyl, n-propyl, n-butyl,
The compounds of formula [2] substituted with n-hexyl and benzyl (2 to 6 in Table 1 above) were synthesized according to the same method and procedure as in Example 1, as shown in Table 2. N-ethyl-phthalazine/quaternary ammonium/TCNQ
Complex salt (Example 2), N-propyl-phthalazine/quaternary ammonium/TCNQ complex salt (Example 3), N-butyl-
Phthalazine/quaternary ammonium/TCNCI salt (Example 4), N-hexyl-phthalazine/quaternary ammonium/
A TCNQ complex salt (Example 5) and an N-benzyl-phthalazine/quaternary ammonium/TCNQ complex salt (Example 6) were obtained.
第２表にＮ−アルキル−フタラジン・第四アンモニウム
・沃化水素酸塩のモル数とアセトニトリルの量、ＴＣＮ
Ｑのモル数とアセトニトリルの量、収率および融点につ
いて、実施例２〜６に実施例１を追加して記す、
［応用例］
上述のようにして得た式［１］のＮ−置換−フタラジン
・ＴＣＮＱＣＮ類の用途について述べると、このＴＣＮ
ＱＣＮ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。Table 2 shows the number of moles of N-alkyl-phthalazine/quaternary ammonium/hydriodide and the amount of acetonitrile, TCN
Regarding the number of moles of Q, the amount of acetonitrile, the yield, and the melting point, Example 1 is added to Examples 2 to 6. [Application example] N-substituted - of formula [1] obtained as described above Regarding the uses of phthalazine/TCNQCN, this TCN
QCNs can be used, for example, as the solid electrolyte of a solid electrolytic capacitor consisting of a capacitor element made of two sheets of aluminum foil wrapped around a separator, or as the solid electrolyte of a solid electrolytic capacitor consisting of a capacitor element of tantalum powder sintered body. It is something.
Claims (2)
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-phthalazine/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_6 or a benzyl group. m is the neutral 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 7,8,8-tetracyanoquinodimethane.
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−フタラジン・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−フタラジン・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、ＲはＣ＿１〜Ｃ＿６のアルキル基またはベ
ンジル基を示し、Ｘはハロゲンを示す。 式［１］中、ＲはＣ＿１〜Ｃ＿６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。(2) N-substituted-phthalazine 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-phthalazine 7 represented by the following formula [1]
,7,8,8-tetracyanoquinodimethane complex salts ▲Mathematical formulas, chemical formulas, tables, etc.▼[1] N-substituted-phthalazine 7,7,
A method for producing 8,8-tetracyanoquinodimethane complex salts. In formula [2], R represents a C_1 to C_6 alkyl group or a benzyl group, and X represents a halogen. In formula [1], R represents a C_1 to C_6 alkyl group or a benzyl group. m is the neutral 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 7,8,8-tetracyanoquinodimethane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3193987A JPS63295563A (en) | 1987-02-13 | 1987-02-13 | N-substituted-phthalazine-7,7,8,8-tetracyanoquino-dimethane complex salts and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3193987A JPS63295563A (en) | 1987-02-13 | 1987-02-13 | N-substituted-phthalazine-7,7,8,8-tetracyanoquino-dimethane complex salts and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63295563A true JPS63295563A (en) | 1988-12-01 |
Family
ID=12344939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3193987A Pending JPS63295563A (en) | 1987-02-13 | 1987-02-13 | N-substituted-phthalazine-7,7,8,8-tetracyanoquino-dimethane complex salts and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63295563A (en) |
-
1987
- 1987-02-13 JP JP3193987A patent/JPS63295563A/en active Pending
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