JPS59198447A - Radiation-sensitive image forming material and image forming method - Google Patents
Radiation-sensitive image forming material and image forming methodInfo
- Publication number
- JPS59198447A JPS59198447A JP58072125A JP7212583A JPS59198447A JP S59198447 A JPS59198447 A JP S59198447A JP 58072125 A JP58072125 A JP 58072125A JP 7212583 A JP7212583 A JP 7212583A JP S59198447 A JPS59198447 A JP S59198447A
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- Japan
- Prior art keywords
- image forming
- poly
- radiation
- general formula
- ketone
- Prior art date
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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
- G03F7/0384—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the main chain of the photopolymer
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Preparing Plates And Mask In Photomechanical Process (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Abstract
Description
【発明の詳細な説明】
この発明は輻射線を用いて画像を形成する所趙リソグラ
フィーに関する新規な材料およびこの拐料を用いて画像
を形成する方法に係わるものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel material for lithography that uses radiation to form images, and a method for forming images using this material.
リソグラフィー技術は微細加工、印刷、写真、半導体、
染色等、広範囲にわたる技術分野において応用されて臂
る。本発明の新規羽料およびその画像形成方法はそれら
各分野に使用可能であるが、半導体素子や集積回路など
の固体デバイスを製造するプロセスに利用し、ポジ型レ
ジストとして特に有用である。最近集積回路の高密度化
、高速化、小型化の要求に応じて、より−RUの′f!
、細パターンの形成が必要となシ、可視光から紫外光を
用しする通常のフォトリソグラフィーに代る新しい技術
の開発が急務となっている。そこで光よシ更に波長の短
い遠紫外光、X−線、電子線等を用いるリソグラフィー
技術が研究されている。この中心となるレジスト材料に
対する要求性能として感度、解像力、エッチ〉グ耐性、
現像許容度、安定性等、広範な要求があるが、従来開発
された材料およびプロセスはこれら全ての性能を充分に
満足するものではなく、性能向上が強く望まれていた。Lithography technology includes microfabrication, printing, photography, semiconductors,
It is applied in a wide range of technical fields such as dyeing. The novel feather material of the present invention and its image forming method can be used in each of these fields, but it is particularly useful as a positive resist for use in the process of manufacturing solid-state devices such as semiconductor elements and integrated circuits. Recently, in response to the demand for higher density, faster speed, and smaller size of integrated circuits, -RU'f!
Since it is necessary to form fine patterns, there is an urgent need to develop a new technique to replace the conventional photolithography that uses visible light to ultraviolet light. Therefore, lithography techniques using far ultraviolet light, X-rays, electron beams, etc., which have shorter wavelengths than light, are being researched. The core performance requirements for resist materials include sensitivity, resolution, etch resistance,
Although there are a wide range of requirements such as development tolerance and stability, conventionally developed materials and processes do not fully satisfy all of these requirements, and there has been a strong desire for improved performance.
例えばポリメタクリル酸メチルのようなポジ型レジスト
では解像力は良好であるが、感度やエツチング耐性が劣
シ、実用上問題があった。またポリメタクリル酸グリシ
ジルのようなネガ型レジストは高感度であり、良好なス
ループットを示すが、解像力や耐ドライエツチング性が
劣シ、改善が強く要望されている。特にポジ型レジスト
では一般的に感度が劣シ、新規拐料の開発が望まれてい
た。For example, positive resists such as polymethyl methacrylate have good resolution, but have poor sensitivity and etching resistance, which poses practical problems. Further, negative resists such as polyglycidyl methacrylate have high sensitivity and exhibit good throughput, but have poor resolution and dry etching resistance, and improvements are strongly desired. In particular, positive resists generally have poor sensitivity, and the development of new resists has been desired.
本発明者等は鋭意研究を重ねた結果、特異な繰シ返し単
位を含有するポリマーおよびそれを用いるプロセスが前
記輻射線に対し優れた特性を示すことが判明し1本発明
に到達した。As a result of extensive research, the inventors of the present invention found that a polymer containing a unique repeating unit and a process using the same exhibit excellent properties against the radiation, and thus arrived at the present invention.
即ち、本発明の要旨は一般式(I)
−C(R+)=OCR2)−(r)
表わす。)で示され条線シ返し単位を含有するポリマー
を有効成分とすることを特徴とする輻射線感応性画像形
成材料およびこの新規材料を用いて薄膜を形成し、遠紫
外光、X線、電子線等の像照射後、有機溶媒で現像する
ことを特徴とする画像形成方法であシ、特にその現像用
溶媒として一般式(II)
Rs ’ −R4(II)
1
示される溶媒を主成分として用いる画像形成方法であυ
、更に尚膜を形成するプロセスにおいてベンゼン、トル
エン、キシレンかう選択すした少くとも一種を主成分と
する溶媒を用いて溶液とし、との溶液から製膜する画像
形成方法に存する。That is, the gist of the present invention is represented by the general formula (I) -C(R+)=OCR2)-(r). ) and a radiation-sensitive image-forming material characterized by containing a polymer containing a striated fiber unit as an active ingredient. It is an image forming method characterized by developing with an organic solvent after irradiation with an image such as a line, and in particular, as the developing solvent, a solvent represented by the general formula (II) Rs'-R4(II) 1 is used as a main component. The image forming method used is
Further, in the process of forming a film, a solvent containing at least one selected from benzene, toluene, and xylene as a main component is used to form a solution, and a film is formed from the solution.
以下本発明を駅間するに、本発明に用込る輻射線感応性
画像形式材料としては、前記一般式(1)で示される繰
シ返し単位を含有するポリマーを有効成分とする。The present invention will be described below. The radiation-sensitive image-forming material used in the present invention contains a polymer containing a repeating unit represented by the general formula (1) as an active ingredient.
かかるポリマーとしては前記一般式(I)で表わされる
繰シ返し単位一種のみから々る高分子、即ちポリ(認−
ブチン)、ポリ(−!−ペンチン)、ポリ(2−ヘキシ
ン)、ポリ(2−ヘプチン)。Such polymers include polymers containing only one type of repeating unit represented by the general formula (I), that is, poly(accredited).
butyne), poly(-!-pentyne), poly(2-hexyne), poly(2-heptyne).
ポリ(−2−オクチン)、ポリ(2−)二ン)、ポリ(
2−デシン)、ポリ(2−ウンデシン)、ポリ(2−ド
ブシン)、ポリ(2−トリプシン)、ポリ(3,3−ジ
メチル−/−ブテン)、ポリ(3−ヘキシン)、ポリ(
3−ヘプチン)、ポリ(3−オクチン)、ポリ(3−)
二ン)、ポリ(3−デシン)、ポリ(3−ウンデシン)
、ポリ(3−ドブシン)、ポリ(3−トリプシン)、ポ
リ(3−テトラデシン)、ポリ(グーオクテポリ(Z−
テトラデシン)、ポリ(グーペンタデシン)等、或いは
上記ホモポリマーを形成する各種モノマー〃・ら選ばれ
た一2種以上のモノマーからの共重合体を誉けることが
できる。これらのポリマーけ■および■族遷移金鵜触媒
例えば塩化モリブデン(MOCI−、)系によ、?!換
アセチレンを公知の方法に準じて重合することにより合
成できる〔本発明者等の中の一部のものによる発明(l
F!j開昭5と−3,2乙0ど号、特頻昭j2−/62
3り1号 )〕。poly(-2-octyne), poly(2-)dine), poly(
2-decyne), poly(2-undecyne), poly(2-dobsyne), poly(2-trypsin), poly(3,3-dimethyl-/-butene), poly(3-hexyne), poly(
3-heptyne), poly(3-octyne), poly(3-)
poly(3-decyne), poly(3-undecyne), poly(3-undecyne)
, poly(3-dobcin), poly(3-trypsin), poly(3-tetradecine), poly(guoctepoly(Z-
Copolymers of one or more monomers selected from monomers such as (tetradecine), poly(goupentadecine), etc., or various monomers forming the above-mentioned homopolymers can be used. These polymers can be used as catalysts such as molybdenum chloride (MOCI-) systems. ! It can be synthesized by polymerizing substituted acetylene according to a known method [Invention by some of the present inventors (l
F! J Kaisho 5 and -3, 2 otsu 0 number, special number Showa j 2-/62
3ri No. 1)].
本発明においては、一般に上述のポリマー、好ましくは
、数平均分子−M7万以上(GPO法、スチレン換算)
のポリマー更に必要に応じて公知の1J1i々の添加剤
等をベンゼン、トルエン、キシレンから選択された/a
!以上を主成分とする溶媒に溶解して塗布液を調整し、
シリコンウェハー、ガラス、プリント基板等の基板上に
、種々の方法例えはスピンナーによp回転塗布し、必袂
なi犀の薄膜を形成する。か力・る画像形成拐料上に目
的に応じ、遠紫外光、X−線、電子線等から選択された
輻射線を像状に一定量照射する。In the present invention, the above-mentioned polymer is generally used, preferably a number average molecular weight of 70,000 or more (GPO method, styrene equivalent).
The polymer further contains known additives selected from benzene, toluene, and xylene as necessary.
! Prepare a coating solution by dissolving the above in a solvent containing the main components,
On a substrate such as a silicon wafer, glass, or printed circuit board, a thin film of the desired iridescent material is formed by spin coating using various methods, such as a spinner. A fixed amount of radiation selected from deep ultraviolet light, X-rays, electron beams, etc. is irradiated onto the image-forming material in an imagewise manner depending on the purpose.
次いで前記一般式(It)で示される溶媒を主成分とす
る現像液を用いて常法によシ現像するととができる。Then, it can be developed in a conventional manner using a developer containing a solvent represented by the general formula (It) as a main component.
力・かる現像液としては前記一般式(n)で表わされる
溶媒即ちアセトン、メチルエチルケトン、メチル−n−
プロピルケトン、メチル−イソ−プロピルケトン、メチ
ル−n−ブチルケトン、・ ・ −一」乙
=九」L:=チチ臀中寸ヰ〒メチル−イソ−ブチルケト
ン、ケ
メチルー5ec−プチルヂトン、メチル−t−ブチルケ
トン、メチルグーメチルペンチルケトン、メチル−n−
へキシルケトン、ジエチルケトン、エチル−n−プロピ
ルケトン、玉輿^−二」−;j7− ゛序エチルーn−
ブチルケトン、エチル−1B○−ブチルケトン、エチル
−n−へキシルケトン、ジ−n−プロピルケトン、ジー
1日O−プロピルケトン
チルケトン、iso−プロピル−rl−ブチルケトン、
ISOプロピル−ISO−ブチルケトン、n二プロピル
−n−ペンチルケトン、n−プロピル−n−へキシルケ
トン、ジ−n−ブチルケトン。Examples of the developing solution include solvents represented by the general formula (n), such as acetone, methyl ethyl ketone, methyl-n-
Propyl ketone, methyl-iso-propyl ketone, methyl-n-butyl ketone, ・ -1" Otsu = 9" L: = Chichi medium size ヰ〒 Methyl-iso-butyl ketone, Kemethyl-5ec-butylditone, Methyl-t-butylketone , methyl goo methyl pentyl ketone, methyl-n-
Hexyl ketone, diethyl ketone, ethyl-n-propyl ketone, Tamakoshi^-2'-;j7-
Butyl ketone, ethyl-1B○-butyl ketone, ethyl-n-hexyl ketone, di-n-propyl ketone, di-1 day O-propyl ketone, iso-propyl-rl-butyl ketone,
ISO propyl-ISO-butyl ketone, n-dipropyl-n-pentyl ketone, n-propyl-n-hexyl ketone, di-n-butyl ketone.
ジーisoーブチルケトン、n−ブチル−n−ヘキシル
ケトン、ジ−n−ペンチルケトン、シクロヘキサノン、
シクロペンタノン、シクロヘプタノン等を単独、或いは
これらから選択されたλ種以上を混合したものを挙げる
ことができる。Di-isobutyl ketone, n-butyl-n-hexyl ketone, di-n-pentyl ketone, cyclohexanone,
Examples include cyclopentanone, cycloheptanone, etc. alone, or a mixture of λ or more selected from these.
また、これらの溶媒を主成分として、更に酢酸エチルの
ようなエステル類, n − BitOHの様なアルコ
ール類、n−プロピルセロソルブのようなセロソルブ類
、エチルセロソルブアセテートのようなセロソルブエス
テル類等を混合したものを用いることもできる。しかし
好ましくけアセトン、メチルエチルケトン、メチル−i
so −ブチルクートン等を皐げることができる。Furthermore, with these solvents as the main components, esters such as ethyl acetate, alcohols such as n-BitOH, cellosolves such as n-propyl cellosolve, cellosolve esters such as ethyl cellosolve acetate, etc. are mixed. It is also possible to use a But preferably acetone, methyl ethyl ketone, methyl
So-butyl cutone etc. can be heated.
このようにして形成した画像Fi解像力が良く、ミクロ
ンρユらサブミクロンのファインパターンが再現できた
。The image Fi thus formed had good resolution, and fine patterns of micron and submicron dimensions could be reproduced.
また感度についても通常用いられているポジ型ポリマー
であるポリメタクリル酸メチルに比べて約−倍以上の高
感度を示し、極めて高性能を示すことが見出された。It has also been found that the sensitivity is about twice as high as that of polymethyl methacrylate, which is a commonly used positive type polymer, and exhibits extremely high performance.
次に本発明およびその効果を実施例によりa明するが、
本発明はこれらによシ、なんら限定されるものではない
。Next, the present invention and its effects will be explained with examples.
The present invention is not limited to these in any way.
実施例/
MOCJ!I系触媒によ多重合したポリ(2−オクテン
)(Mn=7,/PX/θ’,Mw/Mn=/,/)り
、り2をキシレン/θoglに溶解した液を調整し、シ
リコンウェハー上にグ,θθ0r.p,mの回転数でス
ピンコーティングをし、o.りμmの薄膜を形成した。Example/MOCJ! Poly(2-octene) (Mn=7, /PX/θ', Mw/Mn=/,/) multipolymerized with I-based catalyst is prepared by dissolving Ri2 in xylene/θogl. on the wafer, θθ0r. Spin coating was performed at rotational speeds of p and m, and o. A thin film with a thickness of μm was formed.
表面粗さ計によジ表面状態を観察した結果極めて均一な
塗膜を形成できた。Observation of the surface condition using a surface roughness meter revealed that an extremely uniform coating film could be formed.
Si,N4を基板材料に、金をX線吸収体として作製し
たマスクを用いて、AJ K線をX線源としてグθθm
J/7の照射を行った。照射後,メチルエチルケトン中
に、20℃において7分間浸漬し現像した。走査型電顕
によって観察した結果、線幅と間隔がθ.!μmのファ
インパターンが再現できた。Using a mask made of Si, N4 as the substrate material and gold as the X-ray absorber, we used AJ K-rays as the X-ray source and
J/7 irradiation was performed. After irradiation, it was immersed in methyl ethyl ketone at 20° C. for 7 minutes and developed. As a result of observation using a scanning electron microscope, the line width and spacing are θ. ! A fine pattern of μm could be reproduced.
なお、比較のためにポリメチルメタクリレ−)(PMM
A)を用いて同様に実施したところcf” 0 0 m
:J/64の照射が必要であった。For comparison, polymethyl methacrylate (PMM)
When the same procedure was carried out using A), cf” 0 0 m
:J/64 irradiation was required.
実施例コ
実施例/で調整した溶液を、シリコンウェハー上にグ、
θ00r、p1mの回転数でスピンコーティングし、O
8りμm17)薄膜を形成した。20℃において30分
プレベークした彼、解、像カテストパターンを形成した
ガラスマスクを密着させた。The solution prepared in Example/Example/ is plated on a silicon wafer.
Spin coating at a rotation speed of θ00r, p1m, and O
A thin film of 8μm17) was formed. After prebaking at 20° C. for 30 minutes, a glass mask with an image test pattern formed thereon was attached.
次にj0θW Xe −Hgランプを光源として遠紫外
線を、30秒間照射した。照射後、メチルエチルケトン
中′に、2θ℃、7分間浸漬し現像した。Next, deep ultraviolet rays were irradiated for 30 seconds using a j0θW Xe-Hg lamp as a light source. After irradiation, the film was developed by immersing it in methyl ethyl ketone at 2θ°C for 7 minutes.
走査型電子顕微蜆によって観察した結果0.どμmのシ
ャープな像が形成できた。The result of observation using a scanning electron microscope was 0. A sharp image of several μm could be formed.
実施例3
実施例−のポリ(2−オクチン)の代りにポリ(2−デ
シン) (Mn = 6.0! X 10’ 、 Mw
/Mn−/、り)を用いて同様に遠紫外線を3θ秒間照
射した。同条件で現像した結果シャープな微小レジスト
パターンが形成できた。Example 3 Poly(2-decyne) (Mn = 6.0!
/Mn-/, Ri) was similarly irradiated with deep ultraviolet rays for 3θ seconds. As a result of developing under the same conditions, a sharp microscopic resist pattern was formed.
実施例グ
実M例−2のキシレンの代シにトルエンを溶媒に用すて
同様にリソグラフィ一工程を行った結果、実施例コとほ
ぼ同等な微細パターンが再現できた。As a result of carrying out the same lithography step using toluene as a solvent instead of xylene in Example M Example-2, a fine pattern almost the same as that of Example M could be reproduced.
実施例!
実施例2のメチル・エチル・ケトンの代シにアセトンを
現像液として用い同様に行った結果、実施例2とほぼ同
等なレジスト像が再現できた。Example! As a result of carrying out the same procedure using acetone as a developer instead of methyl ethyl ketone in Example 2, a resist image almost equivalent to that of Example 2 could be reproduced.
実施例6
実施例コのメチル・エチル・ケトンの代シにメチルイソ
ブチルケトンを現像液として用い。Example 6 Methyl isobutyl ketone was used as a developer instead of methyl, ethyl, and ketone in Example 6.
同様に行った結果、実施例−とほぼ同等なレジスト像が
得られた。As a result of carrying out the same procedure, a resist image almost equivalent to that of Example-1 was obtained.
実施例2
実施例コのメチル・エチル・ケトンの代シにシクロヘキ
サノンを現像液として用い、同様に行った結果、実施例
コとはソ同等なレジスト像が得られた。Example 2 The same procedure was carried out using cyclohexanone as a developer instead of methyl ethyl ketone in Example 2, and a resist image equivalent to that of Example 2 was obtained.
実施例と
実施例コのポリ(コーオクチン)の代りにポリ(3,3
−ジメチル−/−ブチン)(Mn−λ、//X/θ’
、 Mw /Mn = /、7 )を用すて同様に遠紫
外線を60秒間照射した。同様な条件で処理した結果、
シャープな微小レジストパターンが形成できた。Poly(3,3
-dimethyl-/-butyne) (Mn-λ, //X/θ'
, Mw /Mn = /, 7) and was similarly irradiated with deep ultraviolet rays for 60 seconds. As a result of processing under similar conditions,
A sharp micro resist pattern was formed.
Claims (1)
、R2pj O,からC10のアルチル、2ii; k
表わす)で示される繰シ返り単位を有するポリマーを有
効成分とする輻射線感応性ii!iI像形成材料(2)
一般式(I) (式中、R1は水素ス−けC3からCsのアルキル基、
R2けC8からCい。のアルキル基を表わす)で示され
る繰り返し単位を有するポリマーを有効成分とする輻射
線感応性画像材料から薄膜を形成し、これに輻射線によ
る像照射後、有機溶媒で現像することを得′も徴とする
画像形成方法 (3)有機溶媒は、一般式(■:) R,O−R,(II) 1 (式中、凡およびR4けC6からC6のアルギル基を表
わすか又は脂株式基を形成していてもよい)で示窟れる
溶媒を主成分とするものである特許請求の範囲第1項記
載の画像形成方法 (4)薄Fkは輻射線感応性画像材料拐料をキシレン、
トルエンおよびベンゼンの中から選はれた少くとも/お
8類の#媒に溶Z、・・した溶液から実力にされたもの
である特i′]−員)j求の釘iB ()にJ第−狽記
載の画像形成方法[Claims] (1) General formula (I) (wherein R8 is hydrogen or a C8 alkyl group from C275 to C8, R2pj O, to C10 alkyl, 2ii; k
Radiation sensitivity ii! containing a polymer having a repeating unit as shown in the following formula as an active ingredient! iI image forming material (2)
General formula (I) (wherein, R1 is a hydrogen alkyl group from C3 to Cs,
R2, C8 to C. It is also possible to form a thin film from a radiation-sensitive imaging material containing a polymer having a repeating unit represented by (representing an alkyl group) as an active ingredient, and then develop the film with an organic solvent after irradiating the image with radiation. (3) The organic solvent has the general formula (■:) R, O-R, (II) 1 (wherein and R4 represents an argyl group from C6 to C6 or The image forming method (4) thin Fk according to claim 1 is a method in which the main component is a solvent that can be used to form a radiation-sensitive image material, such as xylene, xylene, etc.
It is made from a solution of Z,... in at least a class #8 solvent selected from toluene and benzene. Image forming method described in J.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58072125A JPS59198447A (en) | 1983-04-26 | 1983-04-26 | Radiation-sensitive image forming material and image forming method |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58072125A JPS59198447A (en) | 1983-04-26 | 1983-04-26 | Radiation-sensitive image forming material and image forming method |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59198447A true JPS59198447A (en) | 1984-11-10 |
JPH0354334B2 JPH0354334B2 (en) | 1991-08-19 |
Family
ID=13480287
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP58072125A Granted JPS59198447A (en) | 1983-04-26 | 1983-04-26 | Radiation-sensitive image forming material and image forming method |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59198447A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08262738A (en) * | 1995-03-27 | 1996-10-11 | Agency Of Ind Science & Technol | Fine pattern forming method |
-
1983
- 1983-04-26 JP JP58072125A patent/JPS59198447A/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08262738A (en) * | 1995-03-27 | 1996-10-11 | Agency Of Ind Science & Technol | Fine pattern forming method |
Also Published As
Publication number | Publication date |
---|---|
JPH0354334B2 (en) | 1991-08-19 |
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