JPH0414782B2 - - Google Patents
Info
- Publication number
- JPH0414782B2 JPH0414782B2 JP59109503A JP10950384A JPH0414782B2 JP H0414782 B2 JPH0414782 B2 JP H0414782B2 JP 59109503 A JP59109503 A JP 59109503A JP 10950384 A JP10950384 A JP 10950384A JP H0414782 B2 JPH0414782 B2 JP H0414782B2
- Authority
- JP
- Japan
- Prior art keywords
- pattern
- polymethylsilsesquioxane
- silylation
- hydroxyl groups
- present
- 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 - Lifetime
Links
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 238000006884 silylation reaction Methods 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- 229920000734 polysilsesquioxane polymer Polymers 0.000 claims description 5
- 238000006482 condensation reaction Methods 0.000 claims description 3
- -1 siloxanes Chemical class 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920002050 silicone resin Polymers 0.000 description 9
- 238000010894 electron beam technology Methods 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 238000001312 dry etching Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000000992 sputter etching Methods 0.000 description 1
- 238000010897 surface acoustic wave method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
Description
【発明の詳細な説明】
産業上の利用分野
本発明はパターン形成材料に関する。本発明
は、さらに詳しく述べると、半導体集積回路
（LSI等）、バブルメモリー素子などの製造におけ
る微細なパターンの形成に有用な、例えば電子
線、Ｘ線、イオンビーム等の高エネルギー輻射線
に感応しかつ熱的に安定であるパターン形成材料
に関する。DETAILED DESCRIPTION OF THE INVENTION FIELD OF INDUSTRIAL APPLICATION The present invention relates to pattern-forming materials. More specifically, the present invention is sensitive to high-energy radiation such as electron beams, The present invention relates to a pattern-forming material which is also thermally stable.
従来の技術
従来、半導体、強誘電体、強磁性体結晶等を用
いた各種のデバイス、例えばLSI、バブルメモリ
ー、弾性表面波フイルターなどの素子において、
極めて微細な回路構成がなされており、また、こ
れにはパターン幅1μm以下の微細加工技術が必要
であることは周知の通りである。微細加工技術に
は、大別して、リソグラフイー技術とエツチング
技術とがあり、どちらの技術もめざましい進歩を
みせている。例えば、リソグラフイー技術は、光
の回折、干渉等による解像性の低下を考慮して、
より波長の短い電子線、Ｘ線等を露光源とする技
術が実用化されている。一方、エツチング技術
は、リアクテイブイオンエツチング、スパツタエ
ツチング等のドライエツチング技術が最近用いら
れるようになつたので、より高精度でのエツチン
グが可能である。電子線等の高エネルギー線に感
応しかつ耐ドライエツチング性や解像性にすぐれ
たパターン形成材料（レジスト）としてラダー構
造をもつたシリコーン樹脂、特にポリシルセスキ
オキサンが考えられる。Conventional technology Conventionally, in various devices using semiconductors, ferroelectric materials, ferromagnetic crystals, etc., such as LSIs, bubble memories, surface acoustic wave filters, etc.,
It is well known that the circuit configuration is extremely fine, and that this requires microfabrication technology with a pattern width of 1 μm or less. Microfabrication technology can be broadly divided into lithography technology and etching technology, and both technologies are showing remarkable progress. For example, lithography technology takes into account the reduction in resolution due to light diffraction, interference, etc.
Techniques that use electron beams, X-rays, etc. with shorter wavelengths as exposure sources have been put into practical use. On the other hand, dry etching techniques such as reactive ion etching and sputter etching have recently come into use, making it possible to perform etching with higher precision. Silicone resins with a ladder structure, particularly polysilsesquioxane, are considered as pattern forming materials (resists) that are sensitive to high-energy rays such as electron beams and have excellent dry etching resistance and resolution.
ポリシルセスキオキサンは、一般に、３官能性
のシロキサンを縮合させて、容易に合成すること
ができる。例えば、ポリメチルシルセスキオキサ
ンは、次の反応式で示されるように、メチルトリ
クロロシランを加水分解し、これをされに縮合さ
せることによつて、合成することができる：
ところが、実際には、上式（）のポリメチル
シルセスキオキサンは得られず、その代りとし
て、次式により表わされるような、縮合反応に寄
与できずに未反応のまゝ分子内に残された水酸基
が分子の末端部もしくはそれ以外の部位に存在す
るポリメチルシルセスキオキサンが得られる。 Polysilsesquioxanes can generally be easily synthesized by condensing trifunctional siloxanes. For example, polymethylsilsesquioxane can be synthesized by hydrolyzing methyltrichlorosilane and condensing it with the following reaction scheme: However, in reality, the polymethylsilsesquioxane of the above formula () cannot be obtained; instead, polymethylsilsesquioxane of the above formula () cannot be obtained and remains unreacted in the molecule, as shown by the following formula, which cannot contribute to the condensation reaction. A polymethylsilsesquioxane in which the hydroxyl group is present at the terminal end of the molecule or at other sites is obtained.
このように未反応の水酸基が分子のラダー構造
内に存在しているシリコーン樹脂は熱硬化性樹脂
となることができる。したがつて、この樹脂は、
レジストプロセスで被加工層上に塗布して溶剤の
蒸発、すなわち、成膜のために加熱する場合、そ
の加熱によつて容易に硬化し、もはやパターン形
成材料として使用し得なくなる。溶剤の蒸発を低
温度で実施することも提案されているが、これで
は時間がかかりすぎて好ましくない。上記したタ
イプのシリコーン樹脂は、また、熱的に不安定で
あるために、長期間の保存に不向きである。 A silicone resin in which unreacted hydroxyl groups are present in the molecular ladder structure can become a thermosetting resin. Therefore, this resin is
When it is applied onto a layer to be processed in a resist process and heated to evaporate the solvent, that is, to form a film, it is easily hardened by the heating and can no longer be used as a pattern forming material. It has also been proposed to carry out the evaporation of the solvent at low temperatures, but this is undesirably time consuming. Silicone resins of the type described above are also thermally unstable and therefore unsuitable for long-term storage.
発明が解決しようとする問題点
以上の説明から理解されるように、３官能性シ
ロキサンの縮合によつて合成したラダー構造のシ
リコーン樹脂には未反応の水酸基が分子内に残さ
れ、これが原因となつて、レジストプロセスで、
その樹脂からなるレジスト液を被加工層上に塗布
した後、溶剤を乾燥したり被加工層との密着性を
高めたりするためにプリベークを行なうと、その
加熱によつて容易に樹脂のゲル化が発生し、もは
やレジストとして使用し得なくなる。本発明は、
このような従来のシリコーン樹脂の問題点を解決
し、100℃以下のペリベーク温度においても発生
することのある未反応水酸基の縮合反応を完全に
防止することができる改良された熱安定なパター
ン形成材料を提供しようとするものである。Problems to be Solved by the Invention As can be understood from the above explanation, unreacted hydroxyl groups remain in the molecule of silicone resins with a ladder structure synthesized by condensation of trifunctional siloxanes, and this may be the cause. In the resist process,
After applying a resist solution made of the resin onto the layer to be processed, prebaking is performed to dry the solvent and increase adhesion to the layer to be processed, and the heating easily causes the resin to gel. occurs, and it can no longer be used as a resist. The present invention
An improved thermally stable pattern-forming material that solves these problems with conventional silicone resins and completely prevents the condensation reaction of unreacted hydroxyl groups, which can occur even at peribaking temperatures below 100°C. This is what we are trying to provide.
問題点を解決するための手段
本発明者らは、上述の問題点を解決すべく研究
の結果、３官能性シロキサンの縮合によつてラダ
ー構造のシリコーン樹脂であるポリシルセスキオ
キサンを合成した後、その分子の末端部及び（又
は）それ以外の部位に残存する未反応水酸基を適
当なシリル化剤、例えばモノハロゲン化シラン、
例えばトリメチルクロロシランなどでシリル化す
ることによつて除去するのが最良であることを見
い出した。Means for Solving the Problems As a result of research to solve the above problems, the present inventors synthesized polysilsesquioxane, which is a silicone resin with a ladder structure, by condensation of trifunctional siloxane. After that, the unreacted hydroxyl groups remaining at the terminal end and/or other parts of the molecule are removed using a suitable silylating agent, such as monohalogenated silane,
We have found that it is best removed by silylation, such as with trimethylchlorosilane.
本発明において、３官能性シロキサンの縮合に
よつて得られるラダー構造のポリシルセスキオキ
サンは、一般に、次式により表わすことができ
る：
（上式において、
R1，R2，R3及びR4は互いに同一もしくは異な
つていてもよくかつそれぞれ置換もしくは非置換
のアルキル基、例えばメチル基、クロロメチル
基、エチル基など、又は置換もしくは非置換のア
リール基、例えばフエニル基、クロロフエニル
基、トリル基などを表わす。）重量平均分子量は、
好ましくは3000〜100000である。 In the present invention, the ladder-structured polysilsesquioxane obtained by condensation of trifunctional siloxane can generally be represented by the following formula: (In the above formula, R 1 , R 2 , R 3 and R 4 may be the same or different from each other, and each is a substituted or unsubstituted alkyl group, such as a methyl group, a chloromethyl group, an ethyl group, or a substituted or represents an unsubstituted aryl group, such as a phenyl group, chlorophenyl group, tolyl group, etc.) The weight average molecular weight is
Preferably it is 3000-100000.
本発明によれば、上記式（）により表わされ
かつ未反応水酸基を分子内に有するポリシルセス
キオキサンを例えば次式により表わされるシリル
化剤：
（式中のＸはハロゲンである）でシリル化する
ことの結果、前者に含まれる水酸基の水素と後者
のハロゲンとを化合させて、ハロゲン化水素の形
で脱離させることができる。 According to the present invention, a silylating agent represented by the following formula: As a result of silylation with (X in the formula is halogen), the hydrogen of the hydroxyl group contained in the former and the halogen of the latter can be combined and eliminated in the form of hydrogen halide.
実施例
以下に記載する実施例は、本発明をさらに説明
するためのものである。EXAMPLES The examples set forth below serve to further illustrate the invention.
例 １：
メチルトリクロロシランの加水分解及び縮合を
経て、前記式（）により表わされるポリメチル
シルセスキオキサンを合成した。このポリマーは
20000の分子量を有しかつ、未反応の水酸基を含
むので、80℃及び10分間のプリベークによつて硬
化してしまつた。Example 1: Polymethylsilsesquioxane represented by the above formula () was synthesized through hydrolysis and condensation of methyltrichlorosilane. This polymer is
Since it has a molecular weight of 20,000 and contains unreacted hydroxyl groups, it was cured by prebaking at 80°C for 10 minutes.
上述のポリメチルシルセスキオキサン10ｇをト
ルエン100c.c.に溶解し、ピリジン20c.c.を添加し、
そしてさらにトリメチルクロロシラン10ｇを滴下
してシリル化を実施した。反応を、60℃で２時間
にわたつて保持した。反応完了後、水50c.c.を加
え、そしてピリジン塩がすべて完全に水層に溶け
るまで水洗を繰り返した。水洗後、沈殿が生成し
なくなるまでアセトニトリルを添加した。得られ
たシリル化ポリメチルシルセスキオキサンは熱的
に安定であり、200℃及び１時間のペーキングに
よつても全く硬化することがなかつた。 Dissolve 10 g of the above polymethylsilsesquioxane in 100 c.c. of toluene, add 20 c.c. of pyridine,
Then, 10 g of trimethylchlorosilane was added dropwise to carry out silylation. The reaction was held at 60°C for 2 hours. After the reaction was completed, 50 c.c. of water was added and water washing was repeated until all the pyridine salt was completely dissolved in the aqueous layer. After washing with water, acetonitrile was added until no precipitate was formed. The obtained silylated polymethylsilsesquioxane was thermally stable and did not harden at all even after paking at 200°C for 1 hour.
本例で、シリル化反応は次の通りに進行したも
のと考えられる：
上記のようにしてシリル化したポリメチルシル
セスキオキサン（分子量20000，分散度1.5）のト
ルエン溶液を膜厚が0.5μmとなるようにシリコン
ウエハー上にスピンコートし、これを窒素気流中
で80℃で15分間にわたつて乾燥させた。乾燥後、
シリコンウエハーを電子線露光装置に入れ、加速
電圧20KVの電子線を照射してパターンを描画し
た。これを、MIBK現像液を用いて、１分間にわ
たつて浸漬現像した。0.5μmライン＆スペースの
パターンが得られた。感度7.0×10-6C／cm2。 In this example, the silylation reaction appears to have proceeded as follows: A toluene solution of polymethylsilsesquioxane (molecular weight 20,000, dispersity 1.5) silylated as described above was spin-coated onto a silicon wafer to a film thickness of 0.5 μm, and this was coated for 80 min in a nitrogen stream. Dry at ℃ for 15 minutes. After drying,
A silicon wafer was placed in an electron beam exposure device, and a pattern was drawn by irradiating it with an electron beam at an acceleration voltage of 20 KV. This was immersed and developed for 1 minute using MIBK developer. A 0.5 μm line and space pattern was obtained. Sensitivity 7.0×10 -6 C/cm 2 .
例 ２：
前記例１に記載の手法を繰り返した。但し、本
例の場合、未反応の水酸基を末端部に含む低分子
量（分子量4000）のポリメチルシルセスキオキサ
ンを使用した。得られたシリル化ポリメチルシル
セスキオキサンは前記例１と同様に150℃及び１
時間のベーキングによつても全く硬化することが
なかつた。ちなみに、シリル化前のそれは60℃及
び10分間のプリベークによつて硬化を開始した。Example 2: The procedure described in Example 1 above was repeated. However, in the case of this example, low molecular weight (molecular weight 4000) polymethylsilsesquioxane containing unreacted hydroxyl groups at the end was used. The obtained silylated polymethylsilsesquioxane was heated at 150°C and 1°C in the same manner as in Example 1 above.
It did not harden at all even after baking for hours. Incidentally, before silylation, curing was started by prebaking at 60°C for 10 minutes.
本例で、シリル化反応は次の通りに進行したも
のと考えられる：
上記のようにしてシリル化したポリメチルシル
セスキオキサン（分子量4000、分散度1.2）のト
ルエン溶液を膜厚が0.5μmとなるようにシリコン
ウエハー上にスピンコートし、これを窒素気流中
で80℃で15分間にわたつて乾燥させた。乾燥後、
シリコンウエハーを電子線露光装置に入れ、加速
電圧20KVの電子線を照射してパターンを描画し
た。これをMIBK現像液を用いて、１分間にわた
つて浸漬現像した。0.3μmライン＆スペースのパ
ターンが得られた。感度4.0×10-5C／cm2。 In this example, the silylation reaction appears to have proceeded as follows: A toluene solution of polymethylsilsesquioxane (molecular weight 4000, dispersity 1.2) silylated as described above was spin-coated onto a silicon wafer to a film thickness of 0.5 μm, and this was coated for 80 min in a nitrogen stream. Dry at ℃ for 15 minutes. After drying,
A silicon wafer was placed in an electron beam exposure device, and a pattern was drawn by irradiating it with an electron beam at an acceleration voltage of 20 KV. This was immersed and developed for 1 minute using MIBK developer. A 0.3μm line and space pattern was obtained. Sensitivity 4.0×10 -5 C/cm 2 .
発明の効果
本発明によれば、３官能性シロキサンの縮合に
よつて得られるシリコーン樹脂から残存水酸基を
除去することができるので、そのシリコーン樹脂
の高感度、高解像性及び高耐ドライエツチング性
を生かしつつ、熱的に安定なパターン形成を実施
することができる。さらに、本発明によれば、レ
ジストプロセスにおいて、温度及び時間を気にせ
ずにレジスト液をプリベークすることができる。
本発明によれば、未反応の水酸基を多く含むシリ
コーン樹脂もシリル化後に容易に使用することが
できる。Effects of the Invention According to the present invention, residual hydroxyl groups can be removed from the silicone resin obtained by condensation of trifunctional siloxane, resulting in high sensitivity, high resolution, and high dry etching resistance of the silicone resin. It is possible to form a thermally stable pattern while taking advantage of the Further, according to the present invention, the resist solution can be prebaked in the resist process without worrying about temperature and time.
According to the present invention, silicone resins containing many unreacted hydroxyl groups can also be easily used after silylation.
Claims (1)
後に未反応のまゝ残された分子内水酸基をシリル
化で除去することによつて得たポリシルセスキオ
キサンからなる、パターン形成材料。 ２ 前記シリル化剤がモノハロゲン化シランであ
る、特許請求の範囲第１項に記載のパターン形成
材料。[Scope of Claims] 1 Consisting of a polysilsesquioxane obtained by condensing trifunctional siloxanes and removing by silylation the intramolecular hydroxyl groups left unreacted after the condensation reaction. Pattern-forming material. 2. The pattern forming material according to claim 1, wherein the silylation agent is a monohalogenated silane.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59109503A JPS60254132A (en) | 1984-05-31 | 1984-05-31 | Pattern forming material |
| DE8585303811T DE3574418D1 (en) | 1984-05-30 | 1985-05-30 | Pattern-forming material and its production and use |
| KR1019850003764A KR900002364B1 (en) | 1984-05-30 | 1985-05-30 | Pattern forming material |
| EP85303811A EP0163538B1 (en) | 1984-05-30 | 1985-05-30 | Pattern-forming material and its production and use |
| US06/835,741 US4657843A (en) | 1984-05-30 | 1986-03-03 | Use of polysilsesquioxane without hydroxyl group for forming mask |
| US07/027,089 US4863833A (en) | 1984-05-30 | 1987-03-16 | Pattern-forming material and its production and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59109503A JPS60254132A (en) | 1984-05-31 | 1984-05-31 | Pattern forming material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60254132A JPS60254132A (en) | 1985-12-14 |
| JPH0414782B2 true JPH0414782B2 (en) | 1992-03-13 |
Family
ID=14511912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59109503A Granted JPS60254132A (en) | 1984-05-30 | 1984-05-31 | Pattern forming material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60254132A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986005284A1 (en) * | 1985-03-07 | 1986-09-12 | Hughes Aircraft Company | Polysiloxane resist for ion beam and electron beam lithography |
| JPS63193956A (en) * | 1987-02-06 | 1988-08-11 | Nippon Zeon Co Ltd | Resin solution composition |
| JPH0660282B2 (en) * | 1989-04-12 | 1994-08-10 | 信越化学工業株式会社 | Heat resistant silicone gel composition |
| JPH0443361A (en) * | 1990-06-11 | 1992-02-13 | Fujitsu Ltd | Organic silicon polymer resist and production thereof |
| US8053159B2 (en) | 2003-11-18 | 2011-11-08 | Honeywell International Inc. | Antireflective coatings for via fill and photolithography applications and methods of preparation thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5388099A (en) * | 1977-01-14 | 1978-08-03 | Japan Synthetic Rubber Co Ltd | Methylpolysiloxane |
| JPS5550645A (en) * | 1978-10-06 | 1980-04-12 | Hitachi Ltd | Semiconductor device |
| JPS56827A (en) * | 1979-06-15 | 1981-01-07 | Japan Synthetic Rubber Co Ltd | Production of block copolymer |
| JPS5649540A (en) * | 1979-06-21 | 1981-05-06 | Fujitsu Ltd | Semiconductor device |
| JPS5760330A (en) * | 1980-09-27 | 1982-04-12 | Fujitsu Ltd | Resin composition |
| JPS5958031A (en) * | 1982-09-28 | 1984-04-03 | Fujitsu Ltd | Silicone resin and manufacture of the same |
-
1984
- 1984-05-31 JP JP59109503A patent/JPS60254132A/en active Granted
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5388099A (en) * | 1977-01-14 | 1978-08-03 | Japan Synthetic Rubber Co Ltd | Methylpolysiloxane |
| JPS5550645A (en) * | 1978-10-06 | 1980-04-12 | Hitachi Ltd | Semiconductor device |
| JPS56827A (en) * | 1979-06-15 | 1981-01-07 | Japan Synthetic Rubber Co Ltd | Production of block copolymer |
| JPS5649540A (en) * | 1979-06-21 | 1981-05-06 | Fujitsu Ltd | Semiconductor device |
| JPS5760330A (en) * | 1980-09-27 | 1982-04-12 | Fujitsu Ltd | Resin composition |
| JPS5958031A (en) * | 1982-09-28 | 1984-04-03 | Fujitsu Ltd | Silicone resin and manufacture of the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60254132A (en) | 1985-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |