JPH01261370A - N-substituted-4,4'-bipyridyl-7,7,8,8-tetracyanoquinodimethnae complex salts and production thereof - Google Patents
N-substituted-4,4'-bipyridyl-7,7,8,8-tetracyanoquinodimethnae complex salts and production thereofInfo
- Publication number
- JPH01261370A JPH01261370A JP8934788A JP8934788A JPH01261370A JP H01261370 A JPH01261370 A JP H01261370A JP 8934788 A JP8934788 A JP 8934788A JP 8934788 A JP8934788 A JP 8934788A JP H01261370 A JPH01261370 A JP H01261370A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- bipyridyl
- substituted
- tetracyanoquinodimethane
- compound
- 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 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 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
- -1 N-substituted-4,4'-bipyridyl 7,7,8,8-tetracyanoquinodimethane Chemical compound 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 15
- 239000003990 capacitor Substances 0.000 abstract description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 239000004065 semiconductor Substances 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 239000007784 solid electrolyte Substances 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 2
- 239000004020 conductor Substances 0.000 abstract description 2
- 239000012776 electronic material Substances 0.000 abstract description 2
- 239000011261 inert gas Substances 0.000 abstract description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 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
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 239000000203 mixture 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
- 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 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 description 1
- FAKGLPCKEIKMMC-UHFFFAOYSA-N 4-(1-methyl-2h-pyridin-4-yl)pyridine Chemical group C1=CN(C)CC=C1C1=CC=NC=C1 FAKGLPCKEIKMMC-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-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
- 238000001816 cooling Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000000706 filtrate Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pyridine Compounds (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−４，４′
−ビピリジル・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, etc. -4,4'
- Bipyridyl 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−４，４−ビピリ
ジル・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-4,4-bipyridyl-7,7,8.8-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.
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
。represents a benzyl 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−４，４′−ビピリジル・第四
アンモニウム塩類を
に
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 N-substituted-4,4'-bipyridyl quaternary ammonium salts 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０１〜Ｃ６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 having 01 to C6 carbon atoms such as pentyl and hexyl (including all isomers such as n- and 1so-).
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０１〜Ｃ６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。Further, R in formula [2] is an 01 to C6 alkyl group or a benzyl 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−４，４′−ビピリジル・ＴＣＮＱＣＮ類
は、式［２コのＮ−置換−４，４′−ビピリジル・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、そ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-4,4'-bipyridyl TCNQCN, have the formula [2 N-substituted-4,4'- -Bipyridyl quaternary ammonium salts can be easily produced in a preferred yield by reacting TCNQ of formula [3]. The manufacturing method will be described below.
式［２コのＮ−置換−４，４′−ビピリジル・第四アン
モニウム塩類は既に公知の化合物であって、４．４−ビ
ピリジ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。このＮ−置換−４，４′−ビピリジ
ル・第四アンモニウム塩類の合成例をｙ、１表に示す。N-substituted-4,4'-bipyridyl quaternary ammonium salts of the formula [2] are already known compounds, and can be easily synthesized from 4,4-bipyridyl using methods known per se. can. Synthesis examples of this N-substituted-4,4'-bipyridyl quaternary ammonium salt are shown in Table 1.
４．４２−ビピリジルを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。When 4.42-bipyridyl is 1, the reaction molar ratio is 1
:1-3 is preferable, and in this example, it was set to 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、Ｃｈ−ｅｍ、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。TCNQ of formula [3] and various salts thereof and methods for producing the same are already known, for example, R, M
J, Am, Ch-em, 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−４，４−
ビピリジル・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′ＩＩｉ道する
。この際、反応溶液に大過剰のエーテルを１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−４，
４′−ビピリジル・ＴＣＮＱ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, N-methyl-4,4- as an example in formula [2]
A hot acetonitrile solution of bipyridyl quaternary ammonium salts and a hot acetonitrile solution of TCNQ of formula [3] are mixed at a hot temperature and then allowed to cool, and the precipitated crystals are separated. 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, it becomes N-methyl-4, an example of formula [1], which does not contain inorganic salts.
4'-bipyridyl/TCNQ 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ど、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 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 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.
［実施例］
更に１本発明に係る式［１］のＮ−置換−４，４−ビピ
リジル・Ｔ ＣＮ Ｑ ｉＮ塩類の具体的な合成方法の
実施例について述べる。[Example] Furthermore, an example of a specific method for synthesizing the N-substituted-4,4-bipyridyl T CN Q iN salt of formula [1] according to the present invention will be described.
実施例−１
Ｎ−メチル−４，４−ビピリジル・第四アンモニウム・
ＴＣＮＱ錯塩の合成について述べる。Example-1 N-methyl-4,4-bipyridyl quaternary ammonium
The synthesis of TCNQ complex salt will be described.
Ｎ−メチル−４，４′−ビピリジル・第四アンモニウム
・沃化水素酸塩０．０１００モルをアセトニトリル５０
ｍ１に熱時溶解し、これにＴＣＮＱＯ，０１５モルをア
セトニトリル３００ｍ１に熱時溶解して庄加し、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、ニーデルで洗浄し、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−４，４′−
ビピリジル・第四アンモニウム・ＴＣＮＱ錯塩、融点２
６８．０〜２７０゜０℃の黒色針状結晶を収率８３％の
高収率で得ることができる。Add 0.0100 mol of N-methyl-4,4'-bipyridyl quaternary ammonium hydroiodide to 50 mol of acetonitrile.
To this, 0.15 mol of TCNQO, dissolved in 300 ml of acetonitrile while hot, is added. After mixing, the mixture is left 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, they are washed with ethanol until the filtrate is no longer colored, washed with a needle, and further dried to obtain pure N-methyl containing no iodide ions. -4,4'-
Bipyridyl quaternary ammonium TCNQ complex salt, melting point 2
Black needle-shaped crystals having a temperature of 68.0 to 270°0C can be obtained in a high yield of 83%.
実施例２〜４
上記実施例１ではＮ−メチル−４，４′−ビピリジル・
第四アンモニウム・Ｔ ＣＮ Ｑ Ｉｔ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２〜４）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−４，４′−ビピリジル・第四アンモニウム・ＴＣＮ
Ｑ錯塩（実施例２）、Ｎ−プロピル−４，４−ビピリジ
ル・第四アンモニウム・ＴＣＮＱ錯塩（実施例３）、Ｎ
−ベンジル−４，４−ビピリジル・第四アンモニウム・
ＴＣＮＱ錯塩（実施例４〉を得た。Examples 2 to 4 In Example 1 above, N-methyl-4,4'-bipyridyl.
The synthesis of quaternary ammonium T CN Q It salt has been described, but compounds of formula [2] in which compound R in formula [2] is substituted with ethyl, n-propyl, and benzyl (2 to 2 in Table 1 above) 4) according to the same method and procedure as in Example 1, as shown in Table 2, N-ethyl-4,4'-bipyridyl quaternary ammonium TCN
Q complex salt (Example 2), N-propyl-4,4-bipyridyl quaternary ammonium TCNQ complex salt (Example 3), N
-benzyl-4,4-bipyridyl quaternary ammonium
A TCNQ complex salt (Example 4) was obtained.
第２表にＮ−アルキル−４，４−ビピリジル・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
、ＴＣＮＱのモル数とアセトニトリルの量、収率右よび
融点について、実施例２〜４に実施例１を追加して記す
。Table 2 shows the number of moles of N-alkyl-4,4-bipyridyl quaternary ammonium hydroiodide and the amount of acetonitrile, the number of moles of TCNQ and the amount of acetonitrile, the yield and the melting point of Example 2. Example 1 will be added to 4 to 4.
［応用例］
上述のようにして得た式［１］のＮ−置換−４，４′−
ビピリジル・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-substituted -4,4'- of formula [1] obtained as described above
Regarding the uses of bipyridyl/TCNQCN,
These TCNQCNs 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 wound 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. It's something you get.
Claims (2)
−ビピリジル・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＿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-4,4' represented by the following formula [1]
-Bipyridyl 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_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.
−ビピリジル・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−４，４′−ビピ
リジル・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−４，４′−ビピリジル
・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、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-4,4' represented by the following formula [2]
-Bipyridyl quaternary ammonium salts are reacted with 7,7,8,8-tetracyanoquinodimethane represented by the following formula [3], ▲Mathematical formula, chemical formula, table, etc.▼[2] There are chemical formulas, tables, etc. ▼ [3] N-substituted-4,4'-bipyridyl 7,7,8,8-tetracyanoquinodimethane complex salts represented by the following formula [1] ▲ Mathematical formula, chemical formula , tables, etc. ▼ [1] A method for producing N-substituted-4,4'-bipyridyl 7,7,8,8-tetracyanoquinodimethane complex salts, characterized by obtaining them. 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 |
|---|---|---|---|
| JP8934788A JPH01261370A (en) | 1988-04-12 | 1988-04-12 | N-substituted-4,4'-bipyridyl-7,7,8,8-tetracyanoquinodimethnae complex salts and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8934788A JPH01261370A (en) | 1988-04-12 | 1988-04-12 | N-substituted-4,4'-bipyridyl-7,7,8,8-tetracyanoquinodimethnae complex salts and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01261370A true JPH01261370A (en) | 1989-10-18 |
Family
ID=13968176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8934788A Pending JPH01261370A (en) | 1988-04-12 | 1988-04-12 | N-substituted-4,4'-bipyridyl-7,7,8,8-tetracyanoquinodimethnae complex salts and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01261370A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8992806B2 (en) | 2003-11-18 | 2015-03-31 | Honeywell International Inc. | Antireflective coatings for via fill and photolithography applications and methods of preparation thereof |
-
1988
- 1988-04-12 JP JP8934788A patent/JPH01261370A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8992806B2 (en) | 2003-11-18 | 2015-03-31 | Honeywell International Inc. | Antireflective coatings for via fill and photolithography applications and methods of preparation thereof |
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