JPH0424365B2 - - Google Patents
Info
- Publication number
- JPH0424365B2 JPH0424365B2 JP23328687A JP23328687A JPH0424365B2 JP H0424365 B2 JPH0424365 B2 JP H0424365B2 JP 23328687 A JP23328687 A JP 23328687A JP 23328687 A JP23328687 A JP 23328687A JP H0424365 B2 JPH0424365 B2 JP H0424365B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- general formula
- polysilane
- molecular weight
- 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.)
- Expired
Links
- 229920000548 poly(silane) polymer Polymers 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- -1 Dimethyl (substituted phenyl) Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 3
- RQJRLVCBMAKXFG-UHFFFAOYSA-N phenyl(silyl)silane Chemical class [SiH3][SiH2]C1=CC=CC=C1 RQJRLVCBMAKXFG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- PZPGRFITIJYNEJ-UHFFFAOYSA-N disilane Chemical compound [SiH3][SiH3] PZPGRFITIJYNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 150000001342 alkaline earth metals Chemical class 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011232 storage material Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
Description
(産業上の利用分野)
本発明は、一般式()
(式中、Rは水酸基、アミノ基、ビニル基、低
級アルキル基、低級アルコキシ基またはハロゲン
を表わす)
で示される繰り返し単位よりなるジメチル(置換
フエニル)シリルメチルポリシラン(以下、ポリ
シラン()と称する)に関する発明、および原
料である一般式()
(式中、R′は前記Rと同一もしくは保護基を
有する水酸基またはアミノ基を表わす) で示さ
れる1,1−ジクロロ−1,2,2−トリメチル
−2−置換フエニルジシラン(以下、ジシラン
()と称する)をアルカリ金属またはアルカリ
土類金属の存在下に縮合反応させることからなる
ポリシラン()の製造法に関する。
本発明のポリシラン()は,フオトレジスト
材料、有機半導体、光情報記憶材料などの電子材
料またはプレセラミツクスとしての機能を有する
有用な化合物であり、文献未載の新規化合物であ
る。
(従来の技術)
従来、ポリシラン類としては、一般式()
(式中、Xはアルキル基またはアリール基を、
nは正の整数を表わす)
で示される鎖状または環状のポリシランを製造
する方法〔ザ・ジャーナル・オブ・アメリカン・
ケミカル・ソサイテイ(The Journal of
American Chemical Society)、第71巻、第963
頁(1949年)、ケミストリー・レターズ
(Chemistry Letters)、第551頁(1976年)、ジャ
ーナル・オブ・ポリマー・サイエンス:ポリマ
ー・レターズ・エデイシヨン(Journal of
polymer Science:Polymer Letters Edition)、
第21巻、第819頁(1983年)、あるいは一般式
()
(式中、Xは前記と同一の意味を、Yはアルキ
ル基またはアリール基を、およびmは正の整数
を表わす)
で示されるジメチルポリシランとアリールアルキ
ルポリシランの共重合体を製造する方法〔アメリ
カ特許第4260780号(1981年)、ジャーナル・オ
ブ・ポリマー・サイエンス:ポリマー・ケミスト
リー・エデイシヨン(Journal of Polymer
Science:Polymer Chemistry Edition)、第22
巻、第159頁(1984年)〕が開示されている。
(発明が解決すべき問題点)
従来のポリシラン類は、前述の一般式()お
よび一般式()で示されるように、ケイ素−ケ
イ素結合よりなる主鎖に、置換基としてアルキル
基およびアリール基を導入したポリシランのみで
あり、本発明の如き置換基としてジメチル(置換
フエニル)シリル基を導入したポリシランは見い
出されていない。
(問題を解決するための手段)
本発明者らは、ケイ素−ケイ素結合よりなる主
鎖に置換基としてジメチル(置換フエニル)シリ
ルメチル基を導入したポリシランの製造法とし
て、
一般式()
(式中、R′は前記と同一の意味を表わす)で
示されるジシラン()を原料とし、このジシラ
ン()とアルカリ金属またはアルカリ土類金属
とを反応させることにより、一般式()
(式中、Rは前記と同一の意味を表わす)で示
される繰り返し単位よりなるポリシラン()が
得られることを見い出し本発明を完成したもので
ある。
本発明のポリシラン()の製造法は、ジシラ
ン()とアルカリ金属またはアルカリ土類金属
とを非プロトン溶媒例えばn−ペンタン、n−ヘ
キサン、ベンゼン、トルエン、テトラヒドロフラ
ンなどの溶媒中で反応させる。本発明で用いるジ
シラン()の置換フエニル基の置換基としては
水酸基、アミノ基、ビニル基、低級アルキル基、
低級アルコキシ基、ハロゲンであり、このうち水
酸基、アミノ基は保護基により保護してもよく、
保護基としてはトリアルキルシリル基が好適であ
り、このほか水酸基の保護基としてベンジル基、
テトラヒドロピラニル基が適している。
本反応において、ジシラン()1当量に対し
てアルカリ金属またはアルカリ土類金属は最少2
当量必要であり、通常は2〜3当量用いる。反応
温度は0℃以上、反応溶媒の沸点以下で行う。反
応時間は使用する反応溶媒や反応温度により決ま
るが、通常は1〜50時間を要する。反応終了後、
ポリシラン類の通常の精製法、例えばベンゼン−
アルコール系で再沈殿を繰り返す等の手段により
精製する。
(効果)
本発明は、ジシラン()をアルカリ金属また
はアルカリ土類金属とともに縮合反応を行うこと
により、ケイ素−ケイ素結合よりなる主鎖に、置
換基としてジメチル(置換フエニル)シリル基を
導入したポリシラン()を見い出したものであ
り、本発明で得られるポリシラン()は、重量
平均分子量(W)5000〜500000、分散度(M
W/Mn)2.0〜30.0であり、フオトレジスト材
料、有機半導体、光情報記憶材料などの電子材料
またはプレセラミツクスとしての機能を有する。
(実施例)
以下、実施例により本発明を説明する。
実施例 1
冷却管、滴下ロート、温度計および攪拌機を備
えた1四つ口フラスコをアルゴン置換した後
に、トルエン300gおよびナトリウム23g(1モル)
を仕込み、攪拌しながら1,1−ジクロロ−1,
2,2−トリメチル−2−(4−メトキシフエニ
ル)ジシラン131.6g(0.5モル)のトルエン溶液
を、反応温度を50℃に保ちながら1時間を要して
滴下した。滴下終了後、引続き50℃で20時間反応
する。反応終了後室温まで冷却し、副生したナト
リウム塩を濾別したのち、濾液を濃縮してトルエ
ンを留去する。濃縮残にべンゼン300mlを加え、
攪拌しながらエタノール1を加えてポリシラン
を晶析させる。減圧下に付着した溶媒を完全に除
去し、白色粉末のジメチル(4−メトキシフエニ
ル)シリルメチルポリシラン52.9gを得た。収率
55%。
H1−核磁気共鳴スペクトル(60MHz,CDC
3)
δppm=−0.5〜1.0(ブロード,Si−CH3 ,
9H)
3.5〜4.0(ブロード,ph−OCH3 ,3H)
6.0〜7.5(ブロード,Si−ph−,4H)
ゲルパーミエーシヨンクロマトグラフイー
測定条件:カラム 日立化成GL−R400M
溶離剤 テトラヒドロフラン
流 速 1.0ml/min
重量平均分子量(M W) 81000
分散度(M W/Mn) 4.5
実施例 2〜8
第1表記載のジシラン()を原料とし、実施
例1と同様に操作して第1表記載のポリシラン
()を得た。収率および物性を第1表にまとめ
て記載する。
(Industrial Application Field) The present invention is based on the general formula () (In the formula, R represents a hydroxyl group, an amino group, a vinyl group, a lower alkyl group, a lower alkoxy group, or a halogen.) Dimethyl (substituted phenyl)silylmethylpolysilane (hereinafter referred to as polysilane ()) consisting of a repeating unit represented by Inventions related to, and the general formula () which is the raw material 1,1-dichloro-1,2,2-trimethyl-2-substituted phenyldisilane (hereinafter referred to as disilane () It relates to a method for producing polysilane (), which comprises subjecting polysilane (2) to a condensation reaction in the presence of an alkali metal or alkaline earth metal. The polysilane () of the present invention is a useful compound having a function as an electronic material such as a photoresist material, an organic semiconductor, an optical information storage material, or a preceramic, and is a new compound that has not been described in any literature. (Prior art) Conventionally, polysilanes have the general formula () (wherein, X is an alkyl group or an aryl group,
(n represents a positive integer) [The Journal of American
Chemical Society (The Journal of
American Chemical Society), Volume 71, No. 963
(1949), Chemistry Letters, p. 551 (1976), Journal of Polymer Science: Polymer Letters Edition.
Polymer Science: Polymer Letters Edition)
Volume 21, page 819 (1983), or General Formula () (In the formula, X has the same meaning as above, Y represents an alkyl group or an aryl group, and m represents a positive integer.) Method for producing a copolymer of dimethylpolysilane and arylalkylpolysilane [American Patent No. 4260780 (1981), Journal of Polymer Science: Polymer Chemistry Edition
Science: Polymer Chemistry Edition), No. 22
Vol., p. 159 (1984)]. (Problems to be Solved by the Invention) Conventional polysilanes have alkyl groups and aryl groups as substituents in the main chain consisting of silicon-silicon bonds, as shown in the above-mentioned general formulas () and (). However, no polysilane has been found that has a dimethyl (substituted phenyl)silyl group introduced as a substituent as in the present invention. (Means for Solving the Problem) The present inventors have developed a method for producing polysilane in which a dimethyl (substituted phenyl)silylmethyl group is introduced as a substituent into the main chain consisting of a silicon-silicon bond, using the general formula () (In the formula, R' represents the same meaning as above) Using disilane () as a raw material, by reacting this disilane () with an alkali metal or an alkaline earth metal, the general formula () The present invention was completed by discovering that a polysilane (2) consisting of a repeating unit represented by the formula (wherein R represents the same meaning as above) can be obtained. The method for producing polysilane () of the present invention involves reacting disilane () with an alkali metal or alkaline earth metal in an aprotic solvent such as n-pentane, n-hexane, benzene, toluene, or tetrahydrofuran. Substituents for the substituted phenyl group of disilane () used in the present invention include a hydroxyl group, an amino group, a vinyl group, a lower alkyl group,
A lower alkoxy group, a halogen, among which a hydroxyl group and an amino group may be protected with a protecting group,
As a protective group, a trialkylsilyl group is suitable, and in addition, as a protective group for a hydroxyl group, a benzyl group,
A tetrahydropyranyl group is suitable. In this reaction, a minimum of 2 alkali metals or alkaline earth metals are used per 1 equivalent of disilane ().
An equivalent amount is required, and usually 2 to 3 equivalents are used. The reaction temperature is 0°C or higher and lower than the boiling point of the reaction solvent. The reaction time is determined by the reaction solvent and reaction temperature used, but usually takes 1 to 50 hours. After the reaction is complete,
Conventional purification methods for polysilanes, such as benzene-
It is purified by means such as repeated reprecipitation with an alcohol system. (Effects) The present invention is a polysilane in which a dimethyl (substituted phenyl)silyl group is introduced as a substituent into the main chain consisting of a silicon-silicon bond by carrying out a condensation reaction of disilane () with an alkali metal or an alkaline earth metal. (), and the polysilane () obtained by the present invention has a weight average molecular weight ( W ) of 5000 to 500000 and a degree of dispersion ( M
W / M n) 2.0 to 30.0, and has functions as electronic materials such as photoresist materials, organic semiconductors, optical information storage materials, or preceramics. (Example) The present invention will be explained below with reference to Examples. Example 1 A four-necked flask equipped with a condenser, a dropping funnel, a thermometer, and a stirrer was purged with argon, and then 300 g of toluene and 23 g (1 mol) of sodium were added.
of 1,1-dichloro-1, while stirring.
A toluene solution of 131.6 g (0.5 mol) of 2,2-trimethyl-2-(4-methoxyphenyl)disilane was added dropwise over 1 hour while maintaining the reaction temperature at 50°C. After the dropwise addition was completed, the reaction was continued at 50°C for 20 hours. After the reaction is completed, the mixture is cooled to room temperature, the by-produced sodium salt is filtered off, and the filtrate is concentrated to remove toluene. Add 300ml of benzene to the concentrated residue,
Add 1 part of ethanol while stirring to crystallize polysilane. The adhering solvent was completely removed under reduced pressure to obtain 52.9 g of dimethyl(4-methoxyphenyl)silylmethylpolysilane as a white powder. yield
55%. H 1 - Nuclear magnetic resonance spectrum (60MHz, CDC
3 ) δppm=-0.5~1.0 (broad, Si- CH3 ,
9H) 3.5 to 4.0 (broad, ph- OCH 3 , 3H) 6.0 to 7.5 (broad, Si-ph-, 4H) Gel permeation chromatography Measurement conditions: Column Hitachi Chemical GL-R400M Eluent Tetrahydrofuran Flow rate 1.0 ml/min Weight average molecular weight ( M W ) 81000 Dispersity ( M W / M n) 4.5 Examples 2 to 8 Disilane ( The described polysilane () was obtained. The yield and physical properties are summarized in Table 1.
【表】
溶離剤 テトラヒドロフラン
流速 1.0ml〓〓
[Table] Eluent Tetrahydrofuran
Flow rate 1.0ml〓〓
Claims (1)
級アルキル基、低級アルコキシ基またはハロゲン
を表わす) で示される繰り返し単位よりなり、重量平均分子
量5000〜500000であるジメチル(置換フエニル)
シリルメチルポリシラン。 2 一般式() (式中、R′は水酸基、アミノ基、ビニル基、
低級アルキル基、低級アルコキシ基、ハロゲンも
しくは保護基を有する水酸基またはアミノ基を表
わす) で示される1,1−ジクロロ−1,2,2−トリ
メチル−2−置換フエニルジシランを、アルカリ
金属またはアルカリ土類金属の存在下に縮合反応
させることを特徴とする一般式() (式中、Rは前記と同一の意味を表わす)で示
される繰返し単位よりなり、重量平均分子量5000
〜500000であるジメチル(置換フエニル)シリル
メチルポリシランの製造法。[Claims] 1 General formula () (In the formula, R represents a hydroxyl group, an amino group, a vinyl group, a lower alkyl group, a lower alkoxy group, or a halogen) Dimethyl (substituted phenyl) having a weight average molecular weight of 5000 to 500000
Silylmethylpolysilane. 2 General formula () (In the formula, R′ is a hydroxyl group, an amino group, a vinyl group,
1,1-dichloro-1,2,2-trimethyl-2-substituted phenyldisilane (representing a lower alkyl group, a lower alkoxy group, a halogen or a hydroxyl group or an amino group having a protective group) is combined with an alkali metal or alkaline earth General formula () characterized by a condensation reaction in the presence of a metal (In the formula, R represents the same meaning as above), and has a weight average molecular weight of 5000
A method for producing dimethyl (substituted phenyl)silylmethyl polysilane with a molecular weight of ~500,000.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP23328687A JPS6475529A (en) | 1987-09-17 | 1987-09-17 | Dimethyl(substituted phenyl)silylmethylpolysilane and production thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP23328687A JPS6475529A (en) | 1987-09-17 | 1987-09-17 | Dimethyl(substituted phenyl)silylmethylpolysilane and production thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6475529A JPS6475529A (en) | 1989-03-22 |
JPH0424365B2 true JPH0424365B2 (en) | 1992-04-24 |
Family
ID=16952720
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP23328687A Granted JPS6475529A (en) | 1987-09-17 | 1987-09-17 | Dimethyl(substituted phenyl)silylmethylpolysilane and production thereof |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6475529A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4000836B2 (en) * | 2001-11-28 | 2007-10-31 | セイコーエプソン株式会社 | Method for forming a film pattern |
-
1987
- 1987-09-17 JP JP23328687A patent/JPS6475529A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6475529A (en) | 1989-03-22 |
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