JPH0449706B2 - - Google Patents
Info
- Publication number
- JPH0449706B2 JPH0449706B2 JP58098293A JP9829383A JPH0449706B2 JP H0449706 B2 JPH0449706 B2 JP H0449706B2 JP 58098293 A JP58098293 A JP 58098293A JP 9829383 A JP9829383 A JP 9829383A JP H0449706 B2 JPH0449706 B2 JP H0449706B2
- Authority
- JP
- Japan
- Prior art keywords
- sensitivity
- resist
- trioxaspiro
- molecular weight
- polymer
- 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
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 8
- 230000035945 sensitivity Effects 0.000 description 27
- 238000010894 electron beam technology Methods 0.000 description 11
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 230000005865 ionizing radiation Effects 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 229920002239 polyacrylonitrile Polymers 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 150000003413 spiro compounds Chemical class 0.000 description 2
- 238000001039 wet etching Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical group OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000005546 reactive sputtering Methods 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000000992 sputter etching Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
【発明の詳細な説明】
本発明は新規なレジスト材料に関するものであ
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel resist materials.
従来の微細加工は、例えば基板自体を加工する
場合には基板上に感光性樹脂（フオトレジスト）
を塗布し、露光・現象する事によりレジスト像を
形成し、レジスト膜に被覆されていない基板部分
をエツチングする方法が取られて来た。しかし、
光を使用する方法では、光による回折効果のため
に、解像性に限界があるために、1μｍ以下の微
細加工には適さない。そこで、最近、半導体集積
回路の高密度化の要請に伴ない、光の代わりに更
に波長の短かいＸ線、あるいは、電子線、γ線、
中性子線、イオンビーム等のエネルギーの放射線
を用いて、解像性の良いレジスト像を形成し、下
の基板を加工する微細加工方式に移りつつある。 In conventional microfabrication, for example, when processing the substrate itself, a photosensitive resin (photoresist) is used on the substrate.
A method has been adopted in which a resist image is formed by coating, exposing and developing the resist film, and then etching the parts of the substrate not covered by the resist film. but,
Methods using light have limited resolution due to the diffraction effect of light, and are therefore not suitable for microfabrication of 1 μm or less. Recently, with the demand for higher density semiconductor integrated circuits, X-rays with shorter wavelengths, electron beams, gamma rays,
A shift is being made to microfabrication methods that use energetic radiation such as neutron beams and ion beams to form resist images with good resolution and process the underlying substrate.
かかる微細加工方法において、レジスト像形成
に用いるレジスト材料は、解像性の良い事はもち
ろん、生産性の面から露光時間を短縮するため
に、電離放射線に対して高感度に反応するレジス
トを用いる事が望ましい。またエツチング方法と
して従来はウエツトエツチング法が用いられてい
たが、ウエツトエツチングでは、サイドエツチお
よびエツチヤントの不純物の影響がある等、欠点
があつた。そこで最近、ドライエツチング法が用
いられるようになつて来た。従つて、レジスト材
料には、プラズマガス、反応性スパツタリング、
イオンミリングに対しての耐性も要求されるよう
になつている。この目的のために、ドライエツチ
耐性を有するレジストが開発されて来たが、一般
に感度が低いのが現状である。例えば、ポリスチ
レン、ポリアクリロニトリル、ポリビニルナフタ
レン等が報告されているが、電子線に対する感度
は、約100μC／cm2と非常に低いものである。 In such a microfabrication method, the resist material used for resist image formation not only has good resolution, but also a resist that responds with high sensitivity to ionizing radiation in order to shorten the exposure time from the viewpoint of productivity. things are desirable. Furthermore, wet etching has conventionally been used as an etching method, but wet etching has disadvantages such as side etching and the influence of impurities in the etchant. Therefore, recently, a dry etching method has come into use. Therefore, resist materials include plasma gas, reactive sputtering,
Resistance to ion milling is also required. For this purpose, resists having dry etch resistance have been developed, but at present they generally have low sensitivity. For example, polystyrene, polyacrylonitrile, polyvinylnaphthalene, etc. have been reported, but their sensitivity to electron beams is very low at about 100 μC/cm 2 .
本発明の目的は、Ｘ線、電子線、γ線等の電離
放射線に対して、高感度を有する新規なレジスト
材料を提供するものである。 An object of the present invention is to provide a novel resist material that has high sensitivity to ionizing radiation such as X-rays, electron beams, and γ-rays.
本発明によれば、一般式
（但しｎは以上５以下の整数を表わす）
で表わされるトリオキサスピロ化合物を構成要素
として含む重量平均分子量10000〜1000000の重合
体からなるレジスト材料が得られる。 According to the invention, the general formula (However, n represents an integer greater than or equal to 5 and less than or equal to 5.) A resist material made of a polymer having a weight average molecular weight of 10,000 to 1,000,000 and containing the trioxaspiro compound represented by the following as a constituent element is obtained.
すなわち、本発明において、上式で表わす事の
できるトリオキサスピロ化合物は、電離放射線に
対して感度が高いために、上記物質を構成要素と
して含む化合物は、電離放射線に対して高感度を
有する。すなわち、本発明においてトリオキサス
ピロ化合物をアクリロニトリル等に共重合させた
ものは、母体のアクリロニトリルに対して、第１
図に示すように、感度が上昇する。感度が上昇す
る事は、それに逆比例して、必要とする露光量が
少なくて良い事を意味するから、電子線露光・Ｘ
線露光でしばしば問題となる露光時間を短縮せし
める事ができる。 That is, in the present invention, since the trioxaspiro compound that can be represented by the above formula has high sensitivity to ionizing radiation, a compound containing the above substance as a constituent has high sensitivity to ionizing radiation. That is, in the present invention, the trioxaspiro compound copolymerized with acrylonitrile etc. has a first
As shown in the figure, the sensitivity increases. Increasing sensitivity means that the required exposure amount is inversely proportional to that, so electron beam exposure/X
Exposure time, which is often a problem with line exposure, can be shortened.
感度が上昇するのは、トリオキサスピロ基が電
離放射線に対して高感度に開裂し架橋反応を起こ
すためだと考えられる。従つて、ｎの数は感度の
上昇という点かられば本質的な問題ではないが１
〜５の範囲が最もよい。また、電子線、Ｘ線等の
電離放射線に対する感度は、分子量の増大につれ
て上昇するが、分子量が1000以下であると感度が
不足し、一方1000000であると現像中に生じる膨
潤のために、解像度が低下し、更には溶解塗布性
にも問題を生じるので、共重合体の分子量は1000
〜1000000が好ましい。中でも重量平均分子量
10000〜1000000が最もよい。分散は、解像度に影
響を与えるので、解像度の観点から分散は３以下
が好ましい。使用者は、要求する感度、解像度を
考え、最も好適な共重合率、分子量を選ぶ事がで
きる。 The increase in sensitivity is thought to be because the trioxaspiro group cleaves with high sensitivity to ionizing radiation and causes a crosslinking reaction. Therefore, the number of n is not an essential problem from the point of view of increasing sensitivity, but 1
A range of 5 to 5 is best. Sensitivity to ionizing radiation such as electron beams and The molecular weight of the copolymer should be 1000 to reduce the molecular weight of the copolymer.
~1000000 is preferred. Among them, weight average molecular weight
10000-1000000 is best. Dispersion affects resolution, so from the viewpoint of resolution, the dispersion is preferably 3 or less. The user can select the most suitable copolymerization rate and molecular weight considering the required sensitivity and resolution.
以下、本発明を実施例によつて説明する。 Hereinafter, the present invention will be explained with reference to Examples.
実施例 １
トリオキサスピロ化合物（ｎ＝５）／スチレ
ン／アクリロニトリルをモル比１／１／１で仕込
み、重合開始剤アゾビスイソブチロニトリルを重
合成分の３モル％加えて70℃で20時間塊状重合を
行なつた。重合物はアセトン−メタノール系で２
回沈澱精製を行なつた。（収率38％）
得られた生成物は、トリオキサスピロ化合物
（ｎ＝５）／スチレン／アクリロニトリル＝13／
52／35で重量平均分子量30000、分散度2.96であ
つた。この得られたポリマーをベンゾニトリルに
溶かし、16％溶液とし、0.2μｍのフイルターで
過してレジスト液とした。これをスピナーを用い
てシリコンウエハー上に塗布（1700回転／分）
し、80℃で30分加熱乾燥して厚さ0.6μｍの均一な
塗布膜を得た。このレジスト膜に種々の露光量で
電子線照射（20KeV）をして、パターン描画を
行つた後、メチルエチルケトン／イソプロピルア
ルコール＝２／１で90秒の現像を行いイソプロパ
ノールで30秒のリンスを行つてレジストパターン
を得た。このレジストの感度曲線は、第２図ａに
示す。比較のため分子量を100000に規格化して示
してある。ポリスチレンの感度曲線およびポリア
クリロニトリルの感度曲線は、第２図ｄ，ｅに示
した。共重合体の感度はゲル化点で2.6×10-5C／
cm2でポリスチレン／アクリロニトリル共重合体に
比べて約２倍上昇している事がわかる。得られた
レジスト像は、1μｍ以下の細線も良好に形成さ
れていた。Example 1 Trioxaspiro compound (n=5)/styrene/acrylonitrile were charged at a molar ratio of 1/1/1, and the polymerization initiator azobisisobutyronitrile was added in an amount of 3 mol% based on the polymerization component, and the mixture was heated at 70°C for 20 hours. Bulk polymerization was carried out. The polymer is an acetone-methanol system with 2
Sedimentation purification was performed. (Yield 38%) The obtained product was a trioxaspiro compound (n=5)/styrene/acrylonitrile=13/
52/35, weight average molecular weight was 30,000, and dispersity was 2.96. The obtained polymer was dissolved in benzonitrile to form a 16% solution, and the solution was passed through a 0.2 μm filter to obtain a resist solution. Apply this onto a silicon wafer using a spinner (1700 revolutions/min)
Then, it was heated and dried at 80° C. for 30 minutes to obtain a uniform coating film with a thickness of 0.6 μm. This resist film was irradiated with electron beams (20 KeV) at various exposure doses to draw a pattern, then developed with methyl ethyl ketone/isopropyl alcohol = 2/1 for 90 seconds, and rinsed with isopropanol for 30 seconds. A resist pattern was obtained. The sensitivity curve of this resist is shown in Figure 2a. For comparison, the molecular weight is normalized to 100,000. The sensitivity curves of polystyrene and polyacrylonitrile are shown in Figures 2d and e. The sensitivity of the copolymer is 2.6×10 -5 C/ at the gel point.
cm 2 is about twice as high as that of polystyrene/acrylonitrile copolymer. In the obtained resist image, even fine lines of 1 μm or less were well formed.
実施例 ２
実施例１と同じ方法で仕込み量のみを変えて合
成したところ、NMR分析の結果、トリオキサス
ピロ化合物（ｎ＝５）／スチレン／アクリロニト
リル＝23／34／43、平均重量分子量35000、分散
3.6である共重合体を合成した。このポリマーを
実施例１と同様にベンゾニトリルに溶かし、レジ
スト液とした。基板に塗布し、加速電圧20KeV
の電子線に対する感度を第２図ｂに示した。ゲル
化点での露光量は、1.9×10-5C／cm2であり同分子
量のポリスチレン／アクリロニトリル共重合体に
対して感度は約３倍増加した。Example 2 Synthesis was performed in the same manner as in Example 1 with only the amount of charge being changed, and as a result of NMR analysis, trioxaspiro compound (n = 5)/styrene/acrylonitrile = 23/34/43, average weight molecular weight 35000, dispersion
A copolymer of 3.6 was synthesized. This polymer was dissolved in benzonitrile in the same manner as in Example 1 to obtain a resist solution. Applied to the substrate, accelerating voltage 20KeV
The sensitivity to electron beams is shown in Figure 2b. The exposure amount at the gelation point was 1.9×10 −5 C/cm 2 , and the sensitivity increased about three times compared to a polystyrene/acrylonitrile copolymer of the same molecular weight.
実施例 ３
トリオキサスピロ化合物（ｎ＝５）／アクリロ
ニトリルをモル比１／１で仕込み、重合開始剤ア
ゾビスイソブチロニトリルを重合成分の３モル％
加えて70℃で22時間塊状重合を行なつた。重合物
はＮ、Ｎ−ジメチルホルムアミドーメタノール系
で２回沈澱精製を行なつた。（収率38％）
得られたポリマーは、トリオキサスピロ化合物
（ｎ＝５）／アクリロニトリル＝43／57、平均重
量分子量50000、分散度2.09であつた。この得ら
れたポリマーをベンゾニトリルに溶かし、基板上
に塗布した後、80℃で30分加熱乾燥して厚さ0.6μ
ｍの均一な塗布膜を得た。このレジストに種々の
露光量で電子線照射（加速電圧20KeV）してパ
ターン描画した後、Ｎ、Ｎ−ジメチルホルムアミ
ドで90秒現像し、ひき続いて、イソプロパノール
で30秒リンスを行つてレジストパターンを得た。
レジストの感度曲線は、第２図のＣに示した。こ
の共重合対の感度は、ゲル化点で9.6×10-6C／cm2
であり、同分子量のポリアクリロニトリルに対し
て約12倍上昇していた。得られたレジスト像は
0.5μｍ厚で0.6μｍのラインアンドスペースが形成
できていた。Example 3 Trioxaspiro compound (n=5)/acrylonitrile was charged at a molar ratio of 1/1, and the polymerization initiator azobisisobutyronitrile was added at 3 mol% of the polymerization component.
In addition, bulk polymerization was carried out at 70°C for 22 hours. The polymer was purified twice by precipitation using an N,N-dimethylformamide-methanol system. (Yield: 38%) The obtained polymer had a trioxaspiro compound (n=5)/acrylonitrile ratio of 43/57, an average weight molecular weight of 50,000, and a dispersity of 2.09. The resulting polymer was dissolved in benzonitrile, applied onto a substrate, and then heated and dried at 80°C for 30 minutes to a thickness of 0.6 μm.
A uniform coating film of m was obtained. After drawing a pattern on this resist by electron beam irradiation (acceleration voltage 20 KeV) at various exposure doses, it was developed with N,N-dimethylformamide for 90 seconds, and then rinsed with isopropanol for 30 seconds to draw the resist pattern. Obtained.
The sensitivity curve of the resist is shown in FIG. 2C. The sensitivity of this copolymerization pair is 9.6×10 -6 C/cm 2 at the gel point.
This was approximately 12 times higher than that of polyacrylonitrile of the same molecular weight. The obtained resist image is
Lines and spaces of 0.6 μm were formed with a thickness of 0.5 μm.
実施例 ４
実施例３で用いたレジストをＸ線（AlKa線）
に適用評価した所、ゲル化点で196ｍＪ／cm2とポ
リアクリロニトリルに対して約20倍高密度化され
ていた。Example 4 The resist used in Example 3 was exposed to X-rays (AlKa rays)
When applied and evaluated, the gel point was 196 mJ/cm 2 , which was about 20 times higher density than polyacrylonitrile.
実施例 ５
実施例３と同様の方法でトリオキサスピロ化合
物（ｎ＝３）／アクリロニトリル＝40／60、平均
重量分子量60000、分散2.1を合成した。加速電圧
20KeVの電子線に対する感度を測つた所、ゲル
化点で９×10-6C／cm2とｎ＝５の場合と同程度の
高感度化がなされていた。Example 5 A trioxaspiro compound (n=3)/acrylonitrile=40/60, average weight molecular weight 60,000, dispersion 2.1 was synthesized in the same manner as in Example 3. acceleration voltage
When the sensitivity to a 20 KeV electron beam was measured, it was found to be 9×10 -6 C/cm 2 at the gel point, which is the same level of sensitivity as when n=5.
実施例 ６
トリオキサスピロ化合物（ｎ＝５）／α−クロ
ロアクリロニトリルをモル比１／１で仕込んで
Ｎ、Ｎ−ジメチルホルムアミド溶液とした。ベン
ゾイルパーオキサイド−ジメチル−Ｐ−トルイジ
ン系のレドツクス重合開始剤を重合成分の２モル
％使用して30℃で８時間反応させた。重合物は
Ｎ、Ｎ−ジメチルホルムアミド−メタノール系で
２回沈澱精製を行なつた。（収率15％）
得られた重合物は、α−クロルアクリロニトリ
ル／トリオキサスピロ化合物（ｎ＝５）＝55／45、
重量平均分子量10000、分散10000、分散度1.9で
あつた。加速電圧20KeV電子線に対するこの重
合体の感度を測定したところ、ゲル化点で1.2×
10-5C／cm2とポリアクリロニトリルに対して46倍
感度がすぐれていた。Example 6 Trioxaspiro compound (n=5)/α-chloroacrylonitrile were charged at a molar ratio of 1/1 to prepare an N,N-dimethylformamide solution. A redox polymerization initiator based on benzoyl peroxide-dimethyl-P-toluidine was used in an amount of 2 mol % based on the polymerization components, and the reaction was carried out at 30° C. for 8 hours. The polymer was purified twice by precipitation using an N,N-dimethylformamide-methanol system. (Yield 15%) The obtained polymer was α-chloroacrylonitrile/trioxaspiro compound (n=5)=55/45,
The weight average molecular weight was 10,000, the dispersion was 10,000, and the degree of dispersion was 1.9. The sensitivity of this polymer to an accelerating voltage of 20 KeV electron beam was measured and was found to be 1.2× at the gel point.
It was 46 times more sensitive than polyacrylonitrile at 10 -5 C/cm 2 .
このように、本発明のレジスト材料は、高感度
で微細レジスト像形成が可能であるので、半導体
集積回路等の高密度を要するプロセスに優れた方
法を提供する。 As described above, the resist material of the present invention enables formation of a fine resist image with high sensitivity, and thus provides an excellent method for processes that require high density, such as semiconductor integrated circuits.
第１図は、本発明において使用される有機高分
子材料において、スピロ化合物の割合と感度の向
上との相関を示す図、第２図は本発明において使
用される高分子材料ａ，ｂ，ｃと従来の材料ｄ，
ｅの電子線に対する感度を示す図である。
Figure 1 is a diagram showing the correlation between the proportion of spiro compounds and improvement in sensitivity in the organic polymer materials used in the present invention, and Figure 2 is a diagram showing the correlation between the proportion of spiro compounds and the improvement in sensitivity in the organic polymer materials used in the present invention. and conventional material d,
FIG. 3 is a diagram showing the sensitivity of e to an electron beam.
Claims (1)
として含む重量平均分子量10000〜1000000の重合
体からなるレジスト材料。[Claims] 1. General formula (However, n represents an integer of 1 or more and 5 or less.) A resist material made of a polymer having a weight average molecular weight of 10,000 to 1,000,000 and containing a trioxaspiro compound represented by the following as a structural unit.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58098293A JPS59223422A (en) | 1983-06-02 | 1983-06-02 | Resist material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58098293A JPS59223422A (en) | 1983-06-02 | 1983-06-02 | Resist material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59223422A JPS59223422A (en) | 1984-12-15 |
| JPH0449706B2 true JPH0449706B2 (en) | 1992-08-12 |
Family
ID=14215873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58098293A Granted JPS59223422A (en) | 1983-06-02 | 1983-06-02 | Resist material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59223422A (en) |
-
1983
- 1983-06-02 JP JP58098293A patent/JPS59223422A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59223422A (en) | 1984-12-15 |
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