JPH01155339A - Photosensitive resin composition - Google Patents
Photosensitive resin compositionInfo
- Publication number
- JPH01155339A JPH01155339A JP31400487A JP31400487A JPH01155339A JP H01155339 A JPH01155339 A JP H01155339A JP 31400487 A JP31400487 A JP 31400487A JP 31400487 A JP31400487 A JP 31400487A JP H01155339 A JPH01155339 A JP H01155339A
- Authority
- JP
- Japan
- Prior art keywords
- formulas
- resin composition
- photosensitive resin
- resist
- tables
- 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.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 21
- 229920005989 resin Polymers 0.000 claims abstract description 19
- 239000011347 resin Substances 0.000 claims abstract description 19
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 13
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 claims abstract description 11
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims abstract description 8
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004380 Cholic acid Substances 0.000 claims abstract description 4
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims abstract description 4
- 229960002471 cholic acid Drugs 0.000 claims abstract description 4
- 235000019416 cholic acid Nutrition 0.000 claims abstract description 4
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims abstract description 4
- 229960003964 deoxycholic acid Drugs 0.000 claims abstract description 4
- SMEROWZSTRWXGI-UHFFFAOYSA-N Lithocholsaeure Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 SMEROWZSTRWXGI-UHFFFAOYSA-N 0.000 claims abstract 3
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 claims abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 7
- 238000000034 method Methods 0.000 abstract description 39
- 230000035945 sensitivity Effects 0.000 abstract description 14
- 239000003513 alkali Substances 0.000 abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 abstract description 7
- 239000001301 oxygen Substances 0.000 abstract description 7
- 229920002050 silicone resin Polymers 0.000 abstract 3
- 238000001020 plasma etching Methods 0.000 description 8
- 238000004090 dissolution Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 229920005601 base polymer Polymers 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000011161 development Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- 208000023514 Barrett esophagus Diseases 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001077957 Spilanthes urens Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- -1 naphthoquinonediazide sulfone Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- VHLDQAOFSQCOFS-UHFFFAOYSA-M tetrakis(2-hydroxyethyl)azanium;hydroxide Chemical compound [OH-].OCC[N+](CCO)(CCO)CCO VHLDQAOFSQCOFS-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は感、光性樹脂組成物に係り、特に、ＫｒＦエキ
シマレーザ（ｚ４９ｎｍ）を用いた二層レジスト法に好
適な感光性樹脂組成物に関する０本組成物は牛導体素子
等の製造に必要な微細ノ（ターン形成に利用される。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a photosensitive resin composition, and in particular, a photosensitive resin composition suitable for a two-layer resist method using a KrF excimer laser (z49 nm). This composition is used for forming fine turns necessary for manufacturing conductor elements and the like.
〔従来の技術〕
ＬＳＩを製造するためのパターン形成法としては、従来
より、ｇ線（４５６ｎｍ ）あるいはｉｆｉ（５６５ｎ
ｍ）の光を使った縮少投影露光法が採用されて米た。し
かしながら、これらＵＶ光を用いたリングラフィ技術で
は、その解像度限界は、理論的には、４ＭｂＤＲＡＭ
の最少線幅に対応した［１８μｍと予想され１６ＭｂＤ
ＲＡＭの製造に必要な最少線幅０．５μｍを解像するこ
とは、従来のリングラフィ技術を用いては困難であると
考えられている。そこで、α５μｍ８解像するための新
しいレジスト材料、プロセス技術あるいはハードが近年
活発に研究されて来た。[Prior Art] As a pattern forming method for manufacturing LSI, G-line (456nm) or IFI (565nm) has conventionally been used.
The reduction projection exposure method using light of m) was adopted. However, in the phosphorography technology using these UV lights, the resolution limit is theoretically 4Mb DRAM.
corresponding to the minimum linewidth of [18 μm and 16 MbD]
It is considered difficult to resolve the minimum line width of 0.5 μm required for manufacturing RAM using conventional phosphorography technology. Therefore, new resist materials, process techniques, and hardware for resolution of α5 μm8 have been actively researched in recent years.
ハードの面では、最近、ＫｒＦエキシマレーザ（２４９
ｎｍ）光を用いた縮少投影無光技術がα５μｍ以下の線
幅を解像するための有力なリングラフィ技術として注目
されている。この技術はＵＶ光よりもさらに短波長の光
を用いて解像度を上げようとするものであるが、使用す
る光の波長が短波長になればなるほど特に、３００ｎｍ
以下では、レジスト材料に大きな問題が生じる。例え
ば、従来から実用に供されているノボラック系レジスト
（ノボラック樹脂とす７トキノンジアジドスルホン酸エ
ステルの組成物）は、ベースポリマおよび感光剤に芳香
環を含むため、２４９ｎｍでの光透過率が悪く、露光光
がレジスト底部まで到達しない。また、高解像性をもた
らす感光剤のブリーチング作用も起こらない０そのため
、これらのレジストではＫｒＦ エキシマレーザ照射
で良好なパターンは得られない。一方、２４９ｎｍにお
けるレジストの光透過性を良くするために、芳香環を含
まないＲＶＩＭＡ系レジストがエキシマレーザレジスト
として評価されているが、これらのレジストは、良好な
パターンは得られるものの、感度が悪く、また、芳香環
を含まないために、反応性イオンエッチフグ（ＲＩＥ）
に対する耐性が劣る。In terms of hardware, recently KrF excimer laser (249
Reduced projection lightless technology using (nm) light is attracting attention as a powerful phosphorography technology for resolving line widths of α5 μm or less. This technology attempts to increase the resolution by using light with a shorter wavelength than UV light, but the shorter the wavelength of the light used, the more
Below, a major problem arises with resist materials. For example, novolak resists (compositions of novolak resin and 7-toquinonediazide sulfonic acid ester) that have been used in practical use have poor light transmittance at 249 nm because the base polymer and photosensitizer contain aromatic rings. , the exposure light does not reach the bottom of the resist. Furthermore, the bleaching effect of the photosensitive agent that provides high resolution does not occur. Therefore, with these resists, good patterns cannot be obtained by KrF excimer laser irradiation. On the other hand, in order to improve the light transmittance of the resist at 249 nm, RVIMA-based resists that do not contain aromatic rings have been evaluated as excimer laser resists, but although these resists can produce good patterns, they have poor sensitivity. , Also, because it does not contain aromatic rings, reactive ion etching (RIE)
less resistant to
一方、プロセス面では、段差基板上でサブミクロンパタ
ーンを形成する方法として、多層レジスト法が提案され
ている。多層レジスト法には、３層レジスト法と２層レ
ジスト法があるｏ ５１−レジスト法は段差基板上に有
機平坦化膜を塗布し、その上に無機中間層、レジストと
重ね、レジストをパターニングした後、これをマスクと
して無機中間層をドライエツチングし、さらに無機中間
層をマスクとして有機平坦化ｇ８０＊ＲＩＥによりバタ
ーニングする方法である。On the other hand, in terms of process, a multilayer resist method has been proposed as a method for forming submicron patterns on a stepped substrate. Multilayer resist methods include three-layer resist method and two-layer resist method. 51-Resist method involves applying an organic flattening film on a stepped substrate, overlaying an inorganic intermediate layer and resist on top of it, and patterning the resist. Thereafter, using this as a mask, the inorganic intermediate layer is dry-etched, and further, using the inorganic intermediate layer as a mask, organic planarization is performed by organic planarization g80*RIE.
この方法は、基本的には従来からの技術が使用できるた
めに早くから検討が開始されたが、工程か非常に複雑で
あり、有機膜、無機膜、有機膜と物性の異なるものが三
層型なるために中間層にクラックやピンホールが発生し
やすいといったことが問題点になっている。この５層レ
ジスト法に対して２層レジスト法では、３層レジスト法
でのレジストと無機中間層の両方の性質を兼ね備えたレ
ジスト、すなわち酸素プラズマ耐性のあるレジストを用
いるためにクラックやピンホールの発生が抑えられ、又
、３層法から２層法になるので工程が簡略化される０
しかし５層レジスト法では上場レジストに従来のレジス
トが使用できるのに対して、２層レジスト法では新たに
酸素プラズマ耐性のあるレジストを開発しなければなら
ないという課題があった０このように、現在までに、Ｋ
ｒＦ エキシマレーザレジストとして、感度、解像度
、ＲＩＥ耐性に優れたレジスト材料は見い出されて奢ら
ず、さらに、２層しジＸ）法の上層レジストとして使用
できる酸素プラズマ耐性ｉこ優れたＫｒＦ エキシマ
レーザレジストも開発されていなかった０なお、ＫｒＥ
エキシマレーザによる市販レジストの評価に関する
文献としては、遠藤らの報告（ＩＥ気通信学会技術研究
報告、８６巻、１３９号、第１頁（１９８７））尋が挙
げられる。Research on this method was started early on because it basically allows the use of conventional technology, but the process is extremely complex and requires a three-layer structure with organic, inorganic, and organic films with different physical properties. Therefore, the problem is that cracks and pinholes are likely to occur in the intermediate layer. In contrast to this five-layer resist method, the two-layer resist method uses a resist that has the properties of both the resist of the three-layer resist method and the inorganic intermediate layer, that is, a resist that is resistant to oxygen plasma, which prevents cracks and pinholes. In addition, the process is simplified by changing from a three-layer method to a two-layer method.0 However, in the five-layer resist method, conventional resists can be used as listed resists, whereas in the two-layer resist method, new resists can be used. The challenge was to develop a resist that is resistant to oxygen plasma.
As an rF excimer laser resist, a resist material with excellent sensitivity, resolution, and RIE resistance has been discovered, and in addition, a KrF excimer laser resist with excellent oxygen plasma resistance can be used as an upper layer resist for the two-layer method. Furthermore, KrE
Literature regarding the evaluation of commercially available resists using excimer lasers includes a report by Endo et al. (IE Technical Research Report, Vol. 86, No. 139, p. 1 (1987)).
上記したように、従来のレジスト材料は、２層レジスト
法用のＫｒＦエキシマレーザレジストとしては、感度、
Ｍ像度、酸素プラズマ耐性のすべての特性を満足するも
のはなく、実用に供し得ないものであった０
本発明の目的は、上記した５つの基本特性を同時に満足
させることのできる２層しジスト法用ＫｒＦエキシマレ
ーザレジストを提供することにある。As mentioned above, conventional resist materials have low sensitivity and low sensitivity as KrF excimer laser resist for two-layer resist method.
There is no one that satisfies all the characteristics of M image resolution and oxygen plasma resistance, and cannot be put to practical use.The object of the present invention is to develop a two-layered structure that can simultaneously satisfy the five basic characteristics mentioned above. An object of the present invention is to provide a KrF excimer laser resist for use in a photolithography method.
上記目的を達成するために、発明者らは種々の材料を検
討した結果、アルカリ可溶性有機ケイ素樹脂と脂肪族ジ
アゾケトンとを主成分として含有する感光性樹脂組成物
が、２層しジスト法用ＫｒＦエキシマレーザレジストと
して優れていることを見い出し、本発明に至ったもので
ある０まず、発明者らは、現在実用に供されているレジ
スト材料がアルカリ現像方式のポジ形レジストであるこ
とを考慮゛し、現行プロセスを変吏することなく使用で
きるよう、２層しジスト法用ＫｒＦエキシマレーザレジ
ストとして、アルカリ現像型ポジ形レジストを検討する
ことにした。In order to achieve the above object, the inventors investigated various materials and found that a photosensitive resin composition containing an alkali-soluble organosilicon resin and an aliphatic diazoketone as main components was made into a two-layer KrF film for use in the cast method. The inventors discovered that it is excellent as an excimer laser resist, leading to the present invention. First, the inventors took into account that the resist materials currently in practical use are positive resists using an alkaline development method. However, in order to be able to use the current process without making any changes, we decided to consider an alkali-developed positive resist as a two-layer KrF excimer laser resist for the resist method.
２層レジスト法用Ｋｒ Ｆエキシマレーザレジストのベ
ースポリマに要求される主な特性は、■Ｏｘ ＲＩ Ｅ
耐性に優れること０■２４９ ｎｍ における光透過性
に優れるこ七の２つである０そこで、上記２つの特性８
Ｆ１時に満足できるアルカリ可溶性樹脂を探索した結果
、主鎖にケイ素原子を含み、側鎖のすべであるいは一部
かフェノール性水酸基を含有する１機基で、かつ、上記
有機基が、水酸基を含み、ベンゼン平面を昏直に切る面
に対して左右対称であるアルカリ可溶性有機ケイ素樹脂
が良いことを見い出した。このような樹脂としては、例
えば、下記−紋穴（５） 、 （６） 、 （７）で示
されるアルカリ可溶性有機ケイ素樹脂等が挙げられる。The main properties required for the base polymer of Kr F excimer laser resist for two-layer resist method are: ■Ox RI E
Excellent resistance 0 ■ Excellent light transmittance at 249 nm
As a result of searching for an alkali-soluble resin that is satisfactory for F1, it was found that the main chain contains a silicon atom, all or part of the side chain contains a phenolic hydroxyl group, and the organic group mentioned above contains a hydroxyl group. It was discovered that an alkali-soluble organosilicon resin that is symmetrical with respect to the plane that cuts the benzene plane perpendicularly is good. Examples of such resins include alkali-soluble organosilicon resins shown in the following (5), (6), and (7).
■ ＯＲｓ ＯＲＩ。■ ORs ORI.
（Ｒ１２０つべＣＨｚへ５ｉｎｓハ”） ｊ
（７）ここで、Ｒ４＋ Ｒａｎ Ｒｙ ＋ Ｒ
１１ｌ Ｒ１１ｔ Ｒ１１はＣｓ−Ｃｓのアルキル基＋
Ｒａｎ Ｒｈｏ ｌ Ｒｓｚはトリアルキルシリル基
で、ｄとｋは１あるいは２ Ｈ＆ ＋ ｅ Ｔ ｈ ＋
はセロを含まない正の整数ｒ ｂ＋ Ｃｓ ｆ＋ ｇｖ
’＊ｊはセロを含む正の整数で、ａ／（ａ＋ｂ＋ｃ
）。(5ins to R120 Hz) j
(7) Here, R4+ Ran Ry + R
11l R11t R11 is Cs-Cs alkyl group +
Ran Rho l Rsz is a trialkylsilyl group, and d and k are 1 or 2 H& + e Th +
is a positive integer that does not include cello r b+ Cs f+ gv
'*j is a positive integer including cello, a/(a+b+c
).
ｅ／（ｅ＋ｆ＋ｇ）、ｈ／（ｈ＋ｉ＋ｊ）は０．４以上
である０
これらの樹脂は、ケイ素原子が主鎖に含まれるため、０
２ＲＩＥ耐性に優れ、側鎖にフェノール性水酸基を有す
る有機基が存在するため、アルカリ可溶性となる０さら
に、何故かはわからないが、上記有機基が、水酸基を含
み、ベンゼン平面８画直に切る面に対して左右対称であ
ると２４９ ｎ ｍ における光透過性が向上した０こ
れらの樹脂は膜厚１μｍで約７０チの光透過性を示す〇
一方、ＫｒＦエキシマレーザレジスト用の感光性溶解阻
害剤Ｉこ要求される主な特性は、■２４９ ｎ ｍの光
吸収が大であること０■光反応の量子収率が大であるこ
七。■光反応生成物が２４９ｎｍに吸収を持たないこと
の他に、−船釣には、光反応前後でアルカリ溶解阻害効
果の差が大きいことやペースポリマとの相溶性が大であ
ること、あるいは適度の結晶性を有していることなども
１蟹な因子である。従米力１らＴＪＶ用に使われている
ナフトキノンジアジドスルホン散エステルは、分子内に
芳香Ｒを持っているために、要求特性■を満足せず、Ｋ
ｒＦエキシマレーザ用としては使用できない。そこで、
光反応生成物が２４９ｎｍ ｌこ光［収を持たないよう
、芳香環を含まない脂肪族ジアゾケトンを検討するこ七
にした。まず、要求特性■■■を満足する脂肪族ジアゾ
ケトン８穐々検討した結果、下記一般式（８）で示され
る化合物が上記特性を満足する脂肪族ジアゾケトンであ
ることを見い出した。e/(e+f+g), h/(h+i+j) is 0.4 or more.0 These resins contain silicon atoms in the main chain, so
2It has excellent RIE resistance and is alkali soluble due to the presence of an organic group having a phenolic hydroxyl group in the side chain.0 Furthermore, although I do not know why, the above organic group contains a hydroxyl group, and the surface cut perpendicularly to the benzene plane by 8 pixels On the other hand, when the resin is bilaterally symmetrical, the light transmittance at 249 nm is improved.0 These resins exhibit a light transmittance of about 70 nm at a film thickness of 1 μm.On the other hand, photosensitive dissolution inhibitors for KrF excimer laser resists The main properties required are: 1. High light absorption at 249 nm; 0. High quantum yield of photoreaction. ■In addition to the fact that the photoreaction product has no absorption at 249 nm, - for boat fishing, there is a large difference in the alkali dissolution inhibiting effect before and after the photoreaction, a large compatibility with the pace polymer, or a moderate Another important factor is that it has crystallinity. The naphthoquinonediazide sulfone powder ester used for TJV such as Jubeiriki 1 does not satisfy the required property (■) because it has an aromatic R in the molecule.
It cannot be used for rF excimer lasers. Therefore,
In order to ensure that the photoreaction product does not have a light yield of 249 nm, we decided to investigate aliphatic diazoketones that do not contain aromatic rings. First, as a result of a thorough investigation of eight aliphatic diazoketones that satisfy the required properties ■■■, it was discovered that the compound represented by the following general formula (8) is an aliphatic diazoketone that satisfies the above properties.
ここで、Ｒｓ ＋ Ｒ１ｌは芳香環を含まない一価の有
機基で、具体的には、ＲａはＣｔ−Ｃ１ｇのアルキル基
や
としではＣ１〜ＣＩＯのフルコキシ基である。しかしな
がら、これら化合物は、感光性溶解阻害剤として一般的
に要求される。大きな溶解阻害効果の差。Here, Rs + R11 is a monovalent organic group not containing an aromatic ring, and specifically, Ra is an alkyl group of Ct-C1g or a flukoxy group of C1 to CIO. However, these compounds are generally required as photosensitive dissolution inhibitors. Large difference in dissolution inhibition effect.
ベースポリマとの相溶性あるいは適度の結晶性といった
特性は不充分で、そのままの形で使用することは困難で
あった。そこで、Ｒｌｓとして、エステル結合で結合で
きる高分子賞の母体を探した結果、下記一般式（１）
（２） （３）で示されるコール酸、デオキシコール酸
、リトコール！！！誘導体が良いことを見い出した。
ＣＨ３
ｈ２υ
（５１ｓ
但し、Ｒ１はＨあるいはＣ１〜ＣＳＯのアルキル基、Ｒ
２はＨあるいは一般式（８）からＲｌｍを除いた基で、
ＯＲ２基のすべてがＯ）１基の鳩舎を除く。Characteristics such as compatibility with base polymers and appropriate crystallinity were insufficient, and it was difficult to use them as they were. Therefore, as Rls, we searched for a polymer base that can be bonded with an ester bond, and found that the following general formula (1)
(2) Cholic acid, deoxycholic acid, litochol shown in (3)! ! ! We found that derivatives are good.
CH3 h2υ (51s However, R1 is H or an alkyl group of C1 to CSO, R
2 is H or a group obtained by removing Rlm from the general formula (8),
All of the 2 ORs are O) except for 1 pigeon coop.
これら化合物は、ＫｒＦエキシマレーザレジ７、）用の
感光性溶解阻害剤としての要求特性をすべて満足するも
のであり、これら化合物は、単独あるいは混合物の形で
用いることができる。These compounds satisfy all the characteristics required as a photosensitive dissolution inhibitor for KrF excimer laser resistors (7), and these compounds can be used alone or in the form of a mixture.
以上示したｌｋｌレジスト法用ＫｒＦエキシマレーザレ
ジストに最適なアルカリ可溶性有機ケイ素樹脂と脂肪族
ジアゾケトンとの組成物は、感度、解像度＋ ０２ＲＩ
Ｅ耐性のすべてに優れた２ｗｉレジス）法Ｊ’ＲＫｒ
Ｆエキシマレーザレジストになる。The composition of the alkali-soluble organosilicon resin and aliphatic diazoketone that is most suitable for the KrF excimer laser resist for the LKL resist method shown above has sensitivity, resolution + 02RI.
2wi Regis method J'RKr with excellent E resistance
Becomes an F excimer laser resist.
ここで、本発明の組成物を、牛導体素子等のパターン形
成に使用する場合の一般的使用法を説明する。アルカリ
可溶性有機ケイ素樹脂６０〜９５重量部と脂肪族ジアゾ
ケトン４０〜５ ｉ：！ＨＩｔＳ七から成る感光性樹脂
組成物を、エチルセロソルブアセテート等の通常の有機
溶剤に溶解させた溶液を、２層レジスト法における下層
レジストの上にスピンコーティングし、適蟲な温度条件
でプリベークを行ない本発明の感光性樹脂組成物の膜を
得る。次いで所望のパターンにＫｒＦエキシマレーザ光
を照射し、アルカリ現像液、例えば、テトラ（２−ヒド
ロキシエチル）アンモニウムヒドロキシドの水溶液等用
いて被照射部を選択的にＢ１１１させ、ポジ形のレジス
トパターンを得る。さらに下層レジストを加工する場合
には、上記レジストパターンをマスクとして酸素プラズ
マにより下層レジストをドライエツチングすることによ
り、高アスペクト比のパターンを形成することができる
。Here, a general method of using the composition of the present invention for forming patterns of conductive elements and the like will be explained. 60-95 parts by weight of alkali-soluble organosilicon resin and 40-5 parts by weight of aliphatic diazoketone:! A solution of a photosensitive resin composition consisting of HItS7 dissolved in a common organic solvent such as ethyl cellosolve acetate is spin-coated onto the lower resist layer in the two-layer resist method, and prebaked under appropriate temperature conditions. A film of the photosensitive resin composition of the present invention is obtained. Next, the desired pattern is irradiated with KrF excimer laser light, and the irradiated area is selectively B111 using an alkaline developer, such as an aqueous solution of tetra(2-hydroxyethyl) ammonium hydroxide, to form a positive resist pattern. obtain. Furthermore, when processing the lower resist, a pattern with a high aspect ratio can be formed by dry etching the lower resist with oxygen plasma using the resist pattern as a mask.
本発明の感光性樹脂組成物において、アルカリ可溶性樹
脂にアルカリ可溶性有機ケイ素樹脂を用いるこ七で（ｈ
ＲＩ Ｅ耐性を用たせることができ、かつ、上記アル
カリ可溶性有機ケイ素樹脂が２４９ｎｍにおける光透過
性に優れることが、感度向上および解像度向上の一助に
なっているものと考えられる。また、本発明の感光性樹
脂組成物に用いた感光性溶解阻害剤は、２４？ｎｍ 光
により効率良く光反応し、反応生成物が２４９ｎｍ に
光吸収を持たないために、これがブリーチング作用とな
って、感度、解像度を向上させたものと考えられる。そ
して、上記二つの主成分を組み合わせることにより、２
層しジスト法用ＫｒＦエキシマレーザレジストとして必
要な、感度、解像度、（ｈＰ、ＩＥ耐性を同時に満足さ
せることができたと考えられる。In the photosensitive resin composition of the present invention, an alkali-soluble organosilicon resin is used as the alkali-soluble resin (h
It is thought that the fact that RIE resistance can be used and the alkali-soluble organosilicon resin has excellent light transmittance at 249 nm helps improve sensitivity and resolution. Moreover, the photosensitive dissolution inhibitor used in the photosensitive resin composition of the present invention is 24? Since the photoreaction occurs efficiently with 249 nm light and the reaction product has no light absorption at 249 nm, this is considered to be a bleaching effect that improves sensitivity and resolution. By combining the above two principal components, 2
It is considered that the sensitivity, resolution, (hP, and IE resistance) required for a KrF excimer laser resist for the layered resist method were simultaneously satisfied.
以下、本発明の実施例のうち、いくつかについて具体的
に説明するが、本発明はこれらに限定されるものではな
い。Hereinafter, some examples of the present invention will be described in detail, but the present invention is not limited thereto.
実施例１゜
（ａ） 感度
０ＦＰＲ−８００（東京応化１ｌｌｌ）８シリコンウエ
ハ上に２０μｍ厚にスピン塗布し、９０°Ｃで３０分。Example 1゜(a) Sensitivity 0FPR-800 (Tokyo Ohka 1llll) 8 Silicon wafer was spin-coated to a thickness of 20 μm and heated at 90° C. for 30 minutes.
２００°Ｃで３０分ベークした。次いで、ベースポリマ
ー 紋穴（７）の１例であるポリ（Ｐ−ヒドロキシベン
ジルシルセスキオキサン）８０重量部と感光性溶解阻害
剤−紋穴（りの１例である（ Ｒ４＝Ｍｅ 、 Ｒ１１
＝Ｍ＠ｅエステル化率１００チ）２０重量部を１−アセ
トキシ−２−エトキシエタンに溶解させ、上記ハードベ
ーク０ＦＰＲ−８００上にスピン塗布し、８５°Ｃで５
０分ベークして（１８μｍ厚のレジスト膜を形成した。Bake at 200°C for 30 minutes. Next, 80 parts by weight of poly(P-hydroxybenzylsilsesquioxane), which is an example of the base polymer Monna (7), and a photosensitive dissolution inhibitor, which is an example of Monna (7) (R4=Me, R11
= M@e esterification rate 100%) 20 parts by weight was dissolved in 1-acetoxy-2-ethoxyethane, spin coated on the above hard-baked 0FPR-800, and heated at 85°C for 5 minutes.
Bake for 0 minutes (to form a resist film with a thickness of 18 μm).
これに種々の異なる照射量のＫｒＦエキシマレーザ光を
露光し、α０５ｏ 規定のテトラ（２−とドロキシエ
チル）アンモニウムヒドロキシドの水溶液を用いて１分
間現像し、１分間水洗した後、残存レジスト膜の厚みを
測定した。そして、残存膜厚（規格化）８１に光量（ｍ
Ｊ／ｍ）に対してプロットし、残膜率ゼロとなる最少露
光量（この値を感度と定義する）を求めた所、約１００
ｍＪ／ｍであり、高感度なＫｒＦエキシマレーザポジ形
レジストであることが確認された。This was exposed to KrF excimer laser light with various irradiation doses, developed for 1 minute using an aqueous solution of α05o-specified tetra(2- and droxyethyl) ammonium hydroxide, and washed with water for 1 minute, and then the thickness of the remaining resist film was determined. was measured. Then, the light amount (m
J/m) and calculated the minimum exposure amount (this value is defined as sensitivity) at which the residual film rate is zero, it was approximately 100
mJ/m, confirming that it is a highly sensitive KrF excimer laser positive resist.
伽） 解像度
上記２層レジスト構造のシリコンウェハに、縮少露光装
置を使って、ＫｒＦエキシマレーザ光を照射し、実施例
１と同様に現像・リンスしたところ、１５μｍのＬ＆Ｓ
が解像できた。したがって、本発明の感光性樹脂組成物
は高解偉性のＫｒＦエキシマレーザポジ形レジストであ
ることが確認された。伽) Resolution A silicon wafer with the above two-layer resist structure was irradiated with KrF excimer laser light using a reduction exposure device, developed and rinsed in the same manner as in Example 1, and a 15 μm L&S was obtained.
was resolved. Therefore, it was confirmed that the photosensitive resin composition of the present invention is a KrF excimer laser positive resist with high resolution.
（ｃ） ０！ＲＩＥ耐性
上記上層レジストのパターンをマスクにして、平行平板
型（ｈＲＩＥ装置（０！圧＝２０ｍｔｏｒｒ ｅ ＲＦ
２００Ｗ（１４ＭＩｌｚ）、カソードバイアス電圧−ｔ
ｓａＶ）を用い、酸素グッズマエッチングしたところ、
α５μｍＬ＆ｓの上層レジストパターンが精度良（ハー
ドベーク０ＦＰＲ−ｓｏｎに転写された。また、その際
の上層レジストのエツチングレートは約４ｎｍ／ｍｉｎ
であり、本発明の感光性樹脂組成物が優れたＯ！ＲＩＥ
耐性を有することが確認された。(c) 0! RIE resistance Using the pattern of the above upper layer resist as a mask, a parallel plate type (hRIE device (0! pressure = 20 mtorr e RF
200W (14MIlz), cathode bias voltage -t
saV) was used to perform oxygen goods etching,
The upper layer resist pattern of α5μmL&s was transferred to the hard-baked 0FPR-son with good precision. Also, the etching rate of the upper layer resist at that time was approximately 4 nm/min.
The photosensitive resin composition of the present invention has an excellent O! R.I.E.
It was confirmed that it has resistance.
実施例２〜９
実施例１七同様にして、種々の条件で実験を行なった０
組成物の成分、配合割合、下層レジスト。Examples 2 to 9 Experiments were conducted under various conditions in the same manner as in Example 17.
Composition components, blending ratio, and lower layer resist.
現偉条件、感度、解像度＝ （ｈＲＩＥレートに関する
具体的な値を表１にまとめた。Current conditions, sensitivity, resolution = (Specific values regarding hRIE rate are summarized in Table 1.
これらの実施例からもわかるように、いずれの実施例に
よる組成物も、感度、解像度、０２ＲＩＥ耐性に優れて
おり、本発明の感光性樹脂組成物が２層しジスト法用Ｋ
ｒＦエキシマレーザポジ形レジストとして有用であるこ
とが確認された。As can be seen from these Examples, the compositions according to all Examples were excellent in sensitivity, resolution, and 02RIE resistance, and the photosensitive resin composition of the present invention was coated in two layers and was
It was confirmed that it is useful as an rF excimer laser positive resist.
以上述べたように、本発明の感光性樹脂組成物は、２層
レジスト法に用いられるＫｒＦエキシマレーザレジスト
として、充分な感度、解像性、０２ＲＩＥ耐性を有する
。さらに、本発明の感光性樹脂組成物は、現在の主流レ
ジストであるアルカリ現像型レジストと同様、アルカリ
現像方式であるために、従来と同様奢こ扱うことができ
る。このようｌこ、本発明の感光性樹脂組成物は、２層
しジスト法用ＫｒＦエキシマレーザレジストとして極め
て効果の大なるものである。As described above, the photosensitive resin composition of the present invention has sufficient sensitivity, resolution, and 02 RIE resistance as a KrF excimer laser resist used in a two-layer resist method. Furthermore, since the photosensitive resin composition of the present invention is developed using an alkali development method like the alkali development type resist that is the current mainstream resist, it can be treated with luxury as before. As described above, the photosensitive resin composition of the present invention is extremely effective as a two-layer KrF excimer laser resist for the resist method.
Claims (1)
ンとを主成分として含有することを特徴とする感光性樹
脂組成物。 ２、上記脂肪族ジアゾケトンが、コール酸、デオキシコ
ール酸あるいはリトコール酸から誘導される脂肪族ジア
ゾケトンの少なくとも一種類を含有することを特徴とす
る特許請求の範囲第１項記載の感光性樹脂組成物。 ３、上記コール酸、デオキシコール酸およびリトコール
酸から誘導される脂肪族ジアゾケトンが、それぞれ、下
記一般式（１）、（２）、および（３）で示される誘導
体であることを特徴とする特許請求の範囲第２項記載の
感光性樹脂組成物。 ▲数式、化学式、表等があります▼（１） ▲数式、化学式、表等があります▼（２） ▲数式、化学式、表等があります▼（３） 但し、Ｒ＿１はＨあるいはＣ＿１〜Ｃ＿１＿０のアルキ
ル基、Ｒ＿２はＨあるいは下記一般式（４）で示あれる
ジアゾケトン基で、ＯＲ＿２基のすべてがＯＨ基の場合
を除く。 ▲数式、化学式、表等があります▼（４） ここで、Ｒ＿３は芳香環を含まない一価の有機基である
。 ４、上記アルカリ可溶性有機ケイ素樹脂が、主鎖にケイ
素原子を含み、側鎖のすべてあるいは一部がフェノール
性水酸基を含有する有機基で、かつ上記有機基が、水酸
基を含み、ベンゼン平面を垂直に切る面に対して左右対
称であることを特徴とする特許請求の範囲第３項記載の
感光性樹脂組成物。 ５、上記アルカリ可溶性有機ケイ素樹脂が、下記一般式
（５）、（６）、（７）で示されるアルカリ可溶性有機
ケイ素樹脂の内から選ばれたものであることを特徴とす
る特許請求の範囲第４項記載の感光性樹脂組成物。 ▲数式、化学式、表等があります▼（５） ▲数式、化学式、表等があります▼（６） ▲数式、化学式、表等があります▼（７） 但し、Ｒ＿４、Ｒ＿５、Ｒ＿７、Ｒ＿８、Ｒ＿９、Ｒ＿
１＿１はＣ＿１〜Ｃ＿６のアルキル基、Ｒ＿６、Ｒ＿１
＿０、Ｒ＿１＿２はトリアルキルシリル基で、ｄとｋは
、あるいは２、ａ、ｅ、ｈはゼロを含まない正の整数、
ｂ、ｃ、ｆ、ｇ、ｉ、ｊはゼロを含む正の整数で、ａ／
（ａ＋ｂ＋ｃ）、ｅ／（ｅ＋ｆ＋ｇ）、ｈ／（ｈ＋ｉ＋
ｊ）は０．４以上である。[Scope of Claims] 1. A photosensitive resin composition containing an alkali-soluble organosilicon resin and an aliphatic diazoketone as main components. 2. The photosensitive resin composition according to claim 1, wherein the aliphatic diazoketone contains at least one type of aliphatic diazoketone derived from cholic acid, deoxycholic acid, or lithocholic acid. . 3. A patent characterized in that the aliphatic diazoketones derived from cholic acid, deoxycholic acid, and lithocholic acid are derivatives represented by the following general formulas (1), (2), and (3), respectively. The photosensitive resin composition according to claim 2. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(3) However, R_1 is H or alkyl from C_1 to C_1_0 The group R_2 is H or a diazoketone group represented by the following general formula (4), except when all OR_2 groups are OH groups. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(4) Here, R_3 is a monovalent organic group that does not contain an aromatic ring. 4. The alkali-soluble organosilicon resin contains a silicon atom in the main chain, all or part of the side chain is an organic group containing a phenolic hydroxyl group, and the organic group contains a hydroxyl group, and the benzene plane is perpendicular to the benzene plane. 4. The photosensitive resin composition according to claim 3, which is symmetrical with respect to a cutting plane. 5. Claims characterized in that the alkali-soluble organosilicon resin is selected from alkali-soluble organosilicon resins represented by the following general formulas (5), (6), and (7). 5. The photosensitive resin composition according to item 4. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(5) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(6) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(7) However, R_4, R_5, R_7, R_8, R_9 , R_
1_1 is an alkyl group of C_1 to C_6, R_6, R_1
_0, R_1_2 are trialkylsilyl groups, d and k are or 2, a, e, h are positive integers not including zero,
b, c, f, g, i, j are positive integers including zero, a/
(a+b+c), e/(e+f+g), h/(h+i+
j) is 0.4 or more.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62314004A JPH07117752B2 (en) | 1987-12-14 | 1987-12-14 | Photosensitive resin composition |
| US07/247,882 US5158855A (en) | 1987-09-24 | 1988-09-22 | α-diazoacetoacetates and photosensitive resin compositions containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62314004A JPH07117752B2 (en) | 1987-12-14 | 1987-12-14 | Photosensitive resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01155339A true JPH01155339A (en) | 1989-06-19 |
| JPH07117752B2 JPH07117752B2 (en) | 1995-12-18 |
Family
ID=18048057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62314004A Expired - Lifetime JPH07117752B2 (en) | 1987-09-24 | 1987-12-14 | Photosensitive resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07117752B2 (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5350660A (en) * | 1990-01-30 | 1994-09-27 | Wako Pure Chemical Industries, Ltd. | Chemical amplified resist material containing photosensitive compound capable of generating an acid and specific polystyrene copolymer having functional groups that become alkali-soluble under an acid atmosphere |
| US5468589A (en) * | 1991-06-18 | 1995-11-21 | Wako Pure Chemical Industries, Ltd. | Resist material and pattern formation process |
| EP0704762A1 (en) | 1994-09-02 | 1996-04-03 | Wako Pure Chemical Industries Ltd | Resist material and pattern formation |
| EP0780732A2 (en) | 1995-12-21 | 1997-06-25 | Wako Pure Chemical Industries Ltd | Polymer composition and resist material |
| KR100313150B1 (en) * | 1997-12-31 | 2001-12-28 | 박종섭 | Lithocholylacidyl(meth)acrylate monomer and copolymer resin having the monomer and photoresist using the resin |
| JP2002055452A (en) * | 2000-08-09 | 2002-02-20 | Tokyo Ohka Kogyo Co Ltd | Positive resist composition and base material with resist layer of the same |
| KR100583092B1 (en) * | 2000-06-15 | 2006-05-24 | 주식회사 하이닉스반도체 | Additive for photoresist composition suitable to resist flow process |
| CN100346230C (en) * | 2001-05-17 | 2007-10-31 | 东京応化工业株式会社 | Material for preservative formation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6480944A (en) * | 1987-09-24 | 1989-03-27 | Hitachi Ltd | Photosensitive resin composition |
-
1987
- 1987-12-14 JP JP62314004A patent/JPH07117752B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6480944A (en) * | 1987-09-24 | 1989-03-27 | Hitachi Ltd | Photosensitive resin composition |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5350660A (en) * | 1990-01-30 | 1994-09-27 | Wako Pure Chemical Industries, Ltd. | Chemical amplified resist material containing photosensitive compound capable of generating an acid and specific polystyrene copolymer having functional groups that become alkali-soluble under an acid atmosphere |
| US5468589A (en) * | 1991-06-18 | 1995-11-21 | Wako Pure Chemical Industries, Ltd. | Resist material and pattern formation process |
| US5670299A (en) * | 1991-06-18 | 1997-09-23 | Wako Pure Chemical Industries, Ltd. | Pattern formation process |
| EP0704762A1 (en) | 1994-09-02 | 1996-04-03 | Wako Pure Chemical Industries Ltd | Resist material and pattern formation |
| EP0780732A2 (en) | 1995-12-21 | 1997-06-25 | Wako Pure Chemical Industries Ltd | Polymer composition and resist material |
| KR100313150B1 (en) * | 1997-12-31 | 2001-12-28 | 박종섭 | Lithocholylacidyl(meth)acrylate monomer and copolymer resin having the monomer and photoresist using the resin |
| KR100583092B1 (en) * | 2000-06-15 | 2006-05-24 | 주식회사 하이닉스반도체 | Additive for photoresist composition suitable to resist flow process |
| JP2002055452A (en) * | 2000-08-09 | 2002-02-20 | Tokyo Ohka Kogyo Co Ltd | Positive resist composition and base material with resist layer of the same |
| CN100346230C (en) * | 2001-05-17 | 2007-10-31 | 东京応化工业株式会社 | Material for preservative formation |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07117752B2 (en) | 1995-12-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2919142B2 (en) | Photosensitive composition and pattern forming method using the same | |
| KR20100092470A (en) | Photoresist compositions and method for multiple exposures with multiple layer resist systems | |
| JPH01155339A (en) | Photosensitive resin composition | |
| JPH01300250A (en) | Photoresist composition | |
| JPH01300248A (en) | Photoresist composition | |
| JPH04130324A (en) | Positive type resist composition | |
| JPH07117750B2 (en) | Photosensitive resin composition | |
| TWI818966B (en) | Photosensitive resin composition and method for manufacturing thereof, resist film, method for forming pattern, and method for manufacturing electronic device | |
| EP3769156B1 (en) | Negative-working ultra thick film photoresist | |
| JPH0623840B2 (en) | Highly sensitive polyamide ester photoresist composition | |
| WO1999045442A1 (en) | Alkaline aqueous solution and method for forming pattern of photosensitive resin composition using the same | |
| TW201726605A (en) | Resist pattern forming method and developer for lithography | |
| JPH04211254A (en) | Radioactive ray sensitive resin composition | |
| JPH0343615B2 (en) | ||
| JPH0343614B2 (en) | ||
| JPS60107644A (en) | Developable water negative resist composition | |
| TWI793267B (en) | Active ray-sensitive or radioactive ray-sensitive resin composition, resist film, pattern-forming method, method for manufacturing electronic device | |
| JPH0261640A (en) | Photosensitive composition | |
| JPS63195650A (en) | Photosensitive resin composition | |
| JPH11149159A (en) | Pattern forming method and semiconductor device manufacturing method | |
| JP2542042B2 (en) | Photosensitive composition | |
| JPH0313947A (en) | Resist pattern forming method | |
| JPH04136856A (en) | Photosensitive resin composition | |
| JPH02187765A (en) | Material for photo-decolorable layer for enhancing contrast and pattern forming method with same | |
| JPH0299954A (en) | Photoresist composition |