JPS62280845A - Photosensitive agent - Google Patents
Photosensitive agentInfo
- Publication number
- JPS62280845A JPS62280845A JP12659086A JP12659086A JPS62280845A JP S62280845 A JPS62280845 A JP S62280845A JP 12659086 A JP12659086 A JP 12659086A JP 12659086 A JP12659086 A JP 12659086A JP S62280845 A JPS62280845 A JP S62280845A
- Authority
- JP
- Japan
- Prior art keywords
- isomers
- matrix resin
- vacuum
- agent
- ortho
- 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
- 229920005989 resin Polymers 0.000 claims abstract description 20
- 239000011347 resin Substances 0.000 claims abstract description 20
- 230000005865 ionizing radiation Effects 0.000 claims abstract description 10
- 238000004090 dissolution Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract 6
- 239000003504 photosensitizing agent Substances 0.000 claims description 20
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 13
- 239000011159 matrix material Substances 0.000 abstract description 10
- 238000010884 ion-beam technique Methods 0.000 abstract description 9
- NZSCUDBGUBVDLO-UHFFFAOYSA-N 3h-indene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CCC2=C1 NZSCUDBGUBVDLO-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000010894 electron beam technology Methods 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 230000018109 developmental process Effects 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 229940100630 metacresol Drugs 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 235000012431 wafers Nutrition 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000005546 reactive sputtering Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000001039 wet etching Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
Abstract
Description
【発明の詳細な説明】 発明の詳細な説明 （産業上の利用分野） 本発明は、ポジレジスト材料に用いる感光剤に関する。[Detailed description of the invention] Detailed description of the invention (Industrial application field) The present invention relates to a photosensitizer used in positive resist materials.
（従来の技術）
従来、集積回路素子は、感光性樹脂（フォトレジスト）
を塗布後、マスクを通して紫外、可視光を露光し、適当
な現像液で現像して、微細パターンを形成し、基板のウ
ェットエツチングを行い、更に、不純物ドーピング等の
処置を経て、製造されている。しかし近年、集積回路素
子が、高集積化されるにつれて、更に、微細パターンを
形成することが強く望まれる情勢となっている。(Prior art) Conventionally, integrated circuit elements are made of photosensitive resin (photoresist).
After coating, it is exposed to ultraviolet and visible light through a mask, developed with an appropriate developer to form a fine pattern, wet etched the substrate, and then undergoes treatments such as impurity doping. . However, in recent years, as integrated circuit elements have become more highly integrated, there has been a strong desire to form even finer patterns.
そのため、紫外、可視光の代りに波長の短い軟Ｘ線、電
子線、遠紫外線及びイオンビーム等を用いて、高精度パ
ターンを形成する技術が展開され始めている。また、ウ
ェットエツチングは、エツチング溶液中に含まれる不純
物による基板への不純物の侵入やエツチング溶液のパタ
ーン下方への侵食（サイドエツチング）等の問題点をも
つため、プラズマ反応性スパッタリング等を用いて、基
板材料を気化侵食するドライエツチング加工に移りつつ
ある。Therefore, techniques for forming highly accurate patterns using soft X-rays, electron beams, deep ultraviolet rays, ion beams, etc. with short wavelengths instead of ultraviolet and visible light are beginning to be developed. In addition, wet etching has problems such as impurities contained in the etching solution entering the substrate and etching solution eroding downwards of the pattern (side etching), so plasma reactive sputtering etc. are used. Dry etching processing, which evaporates and erodes the substrate material, is moving on.
このような情勢から、軟Ｘ線、電子線、遠紫外線および
イオンビーム等の電離放射線用のレジスト材料は、１μ
ｍ以下の高い転写精度を有し、耐ドライエツチ性が高く
、更には、上記電離放射線に対して高感度である必要が
ある。Under these circumstances, resist materials for ionizing radiation such as soft X-rays, electron beams, far ultraviolet rays, and ion beams are
It is necessary to have high transfer accuracy of m or less, high dry etch resistance, and high sensitivity to the above-mentioned ionizing radiation.
現在、高解像度であり、耐ドライエツチ性が良いという
観点からアルカリ水溶液可溶性の樹脂と照射によりアル
カリ水溶液に対する溶解性が変わるジアゾオルソナフト
キノン化合物誘導体の組み合わせによるレジストが最も
広く用いられている。Currently, from the viewpoints of high resolution and good dry etch resistance, the most widely used resist is a combination of a resin soluble in an alkaline aqueous solution and a diazoorthonaphthoquinone compound derivative whose solubility in the alkaline aqueous solution changes upon irradiation.
（発明が解決しようとする問題点）
しかし、従来用いられてきたジアゾオルソキノン化合物
誘導体は、感度が低く、しかも、アルカリ水溶液に対す
る溶解阻止能が小さいために現像液に得られる残存膜厚
が薄くなるという問題点ならびにアルカリ可溶である樹
脂との相溶性が悪いために成膜性が劣るとい゛う問題点
があった。(Problems to be Solved by the Invention) However, the diazoorthoquinone compound derivatives that have been used conventionally have low sensitivity and low dissolution inhibition ability in alkaline aqueous solutions, resulting in a thin residual film thickness in the developer. In addition, there were problems in that film-forming properties were poor due to poor compatibility with alkali-soluble resins.
本発明の目的は、上述の問題点を解決するためになされ
たもので、高真空下での電離放射線照射において用いら
れるポジレジス）・において、感光剤として、感度およ
び現像後に得られる残存膜厚率が従来の感光剤よりも優
れているばかりでなくアルカリ可溶の樹脂との相溶性が
優れている感光剤を提供することにある。The purpose of the present invention has been made to solve the above-mentioned problems. The object of the present invention is to provide a photosensitizer that not only has better compatibility than conventional photosensitizers but also has excellent compatibility with alkali-soluble resins.
（問題点を解決するための手段）
本発明の感光剤は、１−オキソ−２−ジアゾ−ナフトキ
ノンアリルスルフォネートの置換基が、オルト、メタお
よびパラ異性体の少くともいづれか２つの混合物である
ことを特徴とする感光剤である。(Means for Solving the Problems) In the photosensitizer of the present invention, the substituent of 1-oxo-2-diazo-naphthoquinone allylsulfonate is a mixture of at least two of ortho, meta and para isomers. It is a photosensitizer characterized by the following.
（作用）
一般に、電子線、Ｘ線およびイオンビーム等の電離放射
線の照射は高真空下において行われる。感光剤のかかる
高エネルギーに対する吸収は、通常の光に対する吸収と
は全く異なるばかりでなく、照射により生成した活性種
の反応は、空気中と真空中では大きく異なる。従って、
感光剤の性能は、従来の光露光と電子線、Ｘ線およびイ
オンビーム等の電離放射線による露光では全く異なるの
で、電子線、Ｘ線およびイオンビーム等の電離放射線に
よる露光に適する感光剤は、通常の光露光による感光剤
とは別の観点から選ばねばならない。(Function) Generally, irradiation with ionizing radiation such as electron beams, X-rays, and ion beams is performed under high vacuum. The absorption of such high energy by a photosensitizer is not only completely different from the absorption of ordinary light, but also the reaction of active species generated by irradiation is significantly different in air and vacuum. Therefore,
The performance of photosensitizers is completely different between conventional light exposure and exposure to ionizing radiation such as electron beams, X-rays and ion beams, so photosensitizers suitable for exposure to ionizing radiation such as electron beams, X-rays and ion beams are: The sensitizer must be selected from a different point of view than the sensitizer used by ordinary light exposure.
ところが、従来は、光露光用の感光剤をそのまま電子線
、Ｘ線およびイオンビーム等の電離放射露光用の感光剤
として転用してきた。However, conventionally, photosensitizers for light exposure have been directly used as photosensitizers for exposure to ionizing radiation such as electron beams, X-rays, and ion beams.
発明者は、種々のジアゾオルソナフトキノン化合物誘導
体を検討した結果、１，２．ジアゾナフトキノンアリル
スルフォネートの置換基が各々オルト、２′りおよびパ
ラ異性体で感度およびマトリクス樹脂中での溶解阻止能
が異なる事を見い出した。更に、各々の異性体を混合し
て用いることにより著しくアルカリ可溶であるマトリク
ス樹脂との相溶性が改善されることを見い出し本発明に
至った。As a result of studying various diazoorthonaphthoquinone compound derivatives, the inventors discovered 1, 2. It has been found that the substituents of diazonaphthoquinone allyl sulfonate have different sensitivity and ability to inhibit dissolution in a matrix resin depending on the ortho, 2', and para isomers. Furthermore, the present inventors have discovered that by using a mixture of each isomer, the compatibility with the alkali-soluble matrix resin is significantly improved.
ジアゾオルソナフトキノン化合物誘導体の反応を検討し
たところ、空気中では、照射により３−インデンカルボ
ン酸誘導体に変化する。従って、現像過程での溶解度の
変化は、無変化の感光剤と３−インデンカルボン酸誘導
体のアルカリ水溶液対する溶解性の変化により得られる
。一方、真空中では、照射により感光剤は、３−インデ
ンカルボン酸誘導体に変化せずに、アルカリ可溶のマト
リクス樹脂と反応して、カルボン酸エステルを形成する
。従って、現像過程でのアルカリ水溶液に対する溶解性
の差は、マトリクス樹脂中での無変化の感光剤と形成さ
れたカルボン酸エステルとの溶解性の差に依存している
。When we investigated the reaction of diazoorthonaphthoquinone compound derivatives, we found that in air, they change to 3-indenecarboxylic acid derivatives upon irradiation. Therefore, the change in solubility during the development process is obtained by changing the solubility of the unchanged photosensitizer and the 3-indenecarboxylic acid derivative in the alkaline aqueous solution. On the other hand, in a vacuum, the photosensitizer reacts with an alkali-soluble matrix resin to form a carboxylic acid ester without changing into a 3-indenecarboxylic acid derivative upon irradiation. Therefore, the difference in solubility in an alkaline aqueous solution during the development process depends on the difference in solubility between the unchanged photosensitizer and the formed carboxylic acid ester in the matrix resin.
従って、パターン形成に必要な溶解阻止能力は、空気中
での光露光と真空中での電子線、Ｘ線およびイオンビー
ム等の電離放射線露光の場合では、全く異なる。本発明
者は、このような観点から、ジアゾオルソナフトキノン
化合物の誘導体を検討した結果、特に、置換基がフェニ
ル誘導体の場合感度はパラ異性体が比較的優れているが
溶解度が悪くまた樹脂との相溶性も悪いことがわかった
。また、オルト異性体は、溶解阻止能は比較的優れてい
るが、感度はあまりよくないことが明らかになった。従
って、各々異性体は異なる利点を有している。発明者は
、これ等の特性を最大限に引き出す事を試みた結果、オ
ルト、メタおよびパラの異性体を混合することにより感
度、溶解阻止能並びにマトリクス樹脂との相溶性を損な
う事無く真空中での電子線、Ｘ線およびイオンビーム等
の電離放射線露光に適した感光剤を達成する事ができる
ことがわかった。Therefore, the ability to inhibit dissolution required for pattern formation is completely different between light exposure in air and exposure to ionizing radiation such as electron beams, X-rays, and ion beams in vacuum. From this perspective, the present inventor investigated derivatives of diazoorthonaphthoquinone compounds and found that, in particular, when the substituent is a phenyl derivative, the para isomer has relatively good sensitivity, but has poor solubility and poor compatibility with resins. It was also found that the compatibility was poor. It has also been revealed that the orthoisomer has relatively good dissolution inhibiting ability, but its sensitivity is not very good. Therefore, each isomer has different advantages. As a result of trying to maximize these characteristics, the inventors discovered that by mixing ortho, meta, and para isomers, they can be used in vacuum without impairing sensitivity, dissolution inhibition ability, or compatibility with matrix resin. It has been found that it is possible to achieve photosensitizers suitable for exposure to ionizing radiation such as electron beams, X-rays and ion beams.
かかる感光剤は、アルカリ可溶であるマトリクス樹脂に
１０−４０重量％混入して、有機溶剤に溶かすことによ
りレジスト溶液として用いる事が出来る。Such a photosensitizer can be used as a resist solution by mixing 10-40% by weight into an alkali-soluble matrix resin and dissolving it in an organic solvent.
（実施例１）
トリル、１，２−ジアゾナフトキノン−５−スルフォン
酸エステル（オルト異性体２０重量％、メタ異性体３０
重量％、パラ５０重量％）０．６ｇとメタ、クレゾール
ノボラック樹脂２ｇをジメチルフォルムアミド１０ｇに
溶かし、０．５ ｐｍのフィルターを通してレジストに
溶液した。このレジスト溶液を用いて、２■のシリコン
ウェハーに３０００回転／分でスピンコーテングして８
０°Ｃ２３０分のベーキングをして６０００Ａの膜厚の
レジスト薄膜を得た。このレジスト膜に１０＝ｔｏｒｒ
の真空下で電子線を照射して潜像を形成して、０．２Ｎ
のＮａＯＨで６０秒現像する事により０．５ｐｍのライ
ンアンドスペースのレジストパターンを得た。感度は、
４８ｐＣ／ａｍ２、現像後の残膜率は７５％であった。(Example 1) Tolyl, 1,2-diazonaphthoquinone-5-sulfonic acid ester (20% by weight of ortho isomer, 30% by weight of meta isomer)
0.6 g (wt%, para 50 wt%) and 2 g of meta-cresol novolak resin were dissolved in 10 g of dimethylformamide, and the solution was passed through a 0.5 pm filter and applied to the resist. Using this resist solution, spin coating was performed on 2 cm silicon wafers at 3000 revolutions/min.
Baking was performed at 0°C for 230 minutes to obtain a resist thin film with a thickness of 6000A. 10=torr for this resist film
A latent image is formed by irradiating an electron beam under a vacuum of 0.2N.
By developing with NaOH for 60 seconds, a 0.5 pm line and space resist pattern was obtained. The sensitivity is
The remaining film rate after development was 48 pC/am2 and 75%.
（比較例１）
パラ−トリル−１，２−ジアゾナフトキノン−５−スル
フォン酸エステル０．６ｇとメタークレゾールノボラッ
ク樹脂２ｇをジメチルフォルムアミド１０ｇに溶かし、
０．５１１ｍのフィルターを通してレジスト溶液にした
。このレジスト溶液を用いて、２■のシリコンウェハー
に３０００回転／分でスピンコーテングして８０°Ｃ１
３０分のベーキングをして６０００人の膜厚のレジスト
薄膜を得た。このレジスト膜に１０＝ｔｏｒｒの真空下
で電子線を照射して潜像を形成して、０．２ＮのＮａＯ
Ｈで６０秒現像する事により０．５ｐｍのラインアンド
スペースのレジストパターンを得た。感度は、４８μＣ
／ｃｍ２、現像後の残膜率は６０％であり、純粋なパラ
置換体は、実施例１の混合物に比べて、現像後の残膜率
において劣っていた。また、マトリクス樹脂との相溶性
も悪く形成された膜性は良くなかった。(Comparative Example 1) 0.6 g of para-tolyl-1,2-diazonaphthoquinone-5-sulfonic acid ester and 2 g of meta-cresol novolak resin were dissolved in 10 g of dimethylformamide,
A resist solution was obtained through a 0.511 m filter. Using this resist solution, spin coating was carried out on two silicon wafers at 3000 revolutions/min at 80°C.
After baking for 30 minutes, a resist thin film with a thickness of 6,000 wafers was obtained. This resist film was irradiated with an electron beam under a vacuum of 10 torr to form a latent image, and a 0.2N NaO
By developing with H for 60 seconds, a 0.5 pm line and space resist pattern was obtained. Sensitivity is 48μC
/cm2, and the residual film rate after development was 60%, and the pure para-substituted product was inferior to the mixture of Example 1 in the residual film rate after development. Furthermore, the compatibility with the matrix resin was poor, and the properties of the formed film were poor.
（比較例２）
メタ−トリル−１，２−ジアゾナフトキノン−５−スル
フォン酸エステル０．６ｇとメタ−クレゾールノボラッ
ク樹脂２ｇをジメチルフォルムアミド１０ｇに溶かし、
０．５ｐｍのフィルターを通してレジスト溶液にした。(Comparative Example 2) 0.6 g of meta-tolyl-1,2-diazonaphthoquinone-5-sulfonic acid ester and 2 g of meta-cresol novolac resin were dissolved in 10 g of dimethylformamide,
A resist solution was obtained through a 0.5 pm filter.
このレジスト溶液を用いて、２［Ｆ］のシルコンウエノ
１−に３０００回転／分でスピンコーテングして８０°
Ｃ５３０分のベーキングをして６０００人の膜厚のレジ
スト薄膜を得た。このレジスト膜に１０−６ｔｏｒｒの
真空下で電子線を照射して潜像を形成して、０．２Ｎの
ＮａＯＨで６０秒現像する事により０．５μｍのライン
アンドスペースのレジストパターンを得た。感度は、５
５ｐＣ／ａｍ”、現像後の残膜率は６５％であった。Using this resist solution, spin coating was carried out on 2 [F] silicone Ueno 1- at 3000 revolutions/min at 80°.
Baking was performed for C530 minutes to obtain a resist thin film with a thickness of 6000 mm. This resist film was irradiated with an electron beam under a vacuum of 10 -6 torr to form a latent image, and developed with 0.2N NaOH for 60 seconds to obtain a 0.5 μm line-and-space resist pattern. Sensitivity is 5
5 pC/am'', and the residual film rate after development was 65%.
（比較例３）
オルト−トリル、１，２−ジアゾナフトキノン−５−ス
ルフォン酸エステル０．６ｇとメタ−クレゾールノボラ
ック樹脂２ｇをジメチルフォルムアミド１０ｇに溶かし
、０．５ ｐｍのフィルターを通してレジスト溶液にし
た。(Comparative Example 3) 0.6 g of ortho-tolyl, 1,2-diazonaphthoquinone-5-sulfonic acid ester and 2 g of meta-cresol novolak resin were dissolved in 10 g of dimethylformamide and passed through a 0.5 pm filter to form a resist solution. .
このレジスト溶液を用いて、２［Ｆ］のシリコンウェハ
ーに３０００回転ノ分でスピンコーテングして８０°Ｃ
７３０分のベーキングをして６０００Ａの膜厚のレジス
ト薄膜を得た。このレジスト膜に１０＝ｔｏｒｒの真空
下で電子線を照射して潜像を形成して、０．２ＮのＮａ
ＯＨで６０秒現像する事により０．５１１ｍのラインア
ンドスペースのレジストパターンを得た。感度は、６０
ｐＣ／ｃｍ２、現像後の残膜率は６５％であり、５−位
の置換体は、４位の置換体に比べて感度および現像後の
残膜率とも劣っていた。Using this resist solution, spin coating was performed on a silicon wafer at 2[F] at 3000 rotations and heated to 80°C.
Baking was performed for 730 minutes to obtain a resist thin film with a thickness of 6000 Å. This resist film was irradiated with an electron beam under a vacuum of 10 torr to form a latent image, and 0.2N Na
By developing with OH for 60 seconds, a 0.511 m line and space resist pattern was obtained. Sensitivity is 60
pC/cm2, and the residual film rate after development was 65%, and the product substituted at the 5-position was inferior to the product substituted at the 4-position in both sensitivity and film residual rate after development.
比較例２，３でわかるように異性体の混合物よりなる感
光剤は、純粋な感光剤に比べて、特に感度の観点で改良
されていた。As can be seen from Comparative Examples 2 and 3, the photosensitizer made of a mixture of isomers was improved compared to the pure photosensitizer, especially in terms of sensitivity.
実施例ではオルト、メタ、パラの異性体３種類をすべて
混合したが、いづれか２種類のみを混合してもよい。In the examples, all three types of isomers, ortho, meta, and para, were mixed, but only two of them may be mixed.
（発明の効果）(Effect of the invention)
Claims (1)
、現像過程を経る事により微細パターンを形成するパタ
ーン形成法に用いるレジストの感光剤で且つ、アルカリ
可溶な樹脂と溶解阻止能を有する感光剤との混合物から
なるポジレジストに用いる感光剤で、１−オキソ−２−
ジアゾ−ナフトキノンアリルスルフォネートの置換基が
、オルト、メタおよびパラ異性体の少くともいづれか２
つの混合物であることを特徴とする感光剤。A photosensitive agent for resists used in pattern forming methods in which a latent image is formed by irradiating ionizing radiation in a vacuum and a fine pattern is formed through a development process, and it also has the ability to inhibit dissolution of an alkali-soluble resin. A photosensitizer used in positive resist consisting of a mixture with a photosensitizer, 1-oxo-2-
The substituents of diazo-naphthoquinone allyl sulfonate are at least two of ortho, meta and para isomers.
A photosensitizer characterized by being a mixture of two.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12659086A JPS62280845A (en) | 1986-05-30 | 1986-05-30 | Photosensitive agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12659086A JPS62280845A (en) | 1986-05-30 | 1986-05-30 | Photosensitive agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62280845A true JPS62280845A (en) | 1987-12-05 |
| JPH0533791B2 JPH0533791B2 (en) | 1993-05-20 |
Family
ID=14938946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12659086A Granted JPS62280845A (en) | 1986-05-30 | 1986-05-30 | Photosensitive agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62280845A (en) |
-
1986
- 1986-05-30 JP JP12659086A patent/JPS62280845A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0533791B2 (en) | 1993-05-20 |
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