JPH02118651A - Pattern forming material - Google Patents
Pattern forming materialInfo
- Publication number
- JPH02118651A JPH02118651A JP27345088A JP27345088A JPH02118651A JP H02118651 A JPH02118651 A JP H02118651A JP 27345088 A JP27345088 A JP 27345088A JP 27345088 A JP27345088 A JP 27345088A JP H02118651 A JPH02118651 A JP H02118651A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- pattern forming
- forming material
- compd
- acid
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims abstract description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 20
- 229920005989 resin Polymers 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 7
- -1 naphthoquinone diazide compound Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 9
- 239000003929 acidic solution Substances 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 241001175904 Labeo bata Species 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920002189 poly(glycerol 1-O-monomethacrylate) polymer Polymers 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 229910052739 hydrogen Chemical group 0.000 description 1
- 239000001257 hydrogen Chemical group 0.000 description 1
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical class [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229920002454 poly(glycidyl methacrylate) polymer Polymers 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は半導体素子を製造するときに用いられるパター
ン形成材料、具体的にはレジスト材料に係り、特に露光
エネルギー源としてたとえば２４８ｎｍのすなわちＫｒ
Ｆエキシマ・レーザー、遠紫外２ ／、 。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a pattern forming material, specifically a resist material, used when manufacturing semiconductor devices, and particularly relates to a pattern forming material, specifically a resist material, used in the manufacture of semiconductor devices.
F excimer laser, far ultraviolet 2/,.
ン形成する際のポジ型レジ 線光等を用いてバタ スト材料に関する。Positive resist when forming Bata using line light etc. Regarding strike materials.
従来の技術
エキシマ・レーザー（ＡｒＦ ； １９３ ｎｍ 、
ＫｒＦ；２４８ｎｍ 、ＸｅＣＡ； ３０８ｎｍなど）
、遠紫外線（１９ｏ〜３３０ ｎ ｍ付近）を露光源と
する時のレジスト（ＤＵＶレジスト）としては、ポジ型
では、ＡＺ２４０ｏ（シソプレー社） 、ＰＭＭＡ（ポ
リメチルメタクリレート）、ネガ型では、Ｐ ＧＭＡ
（ポリグリシジルメタクリレート）。Conventional technology excimer laser (ArF; 193 nm,
KrF; 248nm, XeCA; 308nm, etc.)
As a resist (DUV resist) when using far ultraviolet rays (near 19o~330 nm) as an exposure source, for positive type, AZ240o (Shisopray Co., Ltd.), PMMA (polymethyl methacrylate), for negative type, PGMA.
(Polyglycidyl methacrylate).
ＣＭＳ（クロロメチル化スチレン；東洋ソーダ）などが
提案されている。ＰＭＭＡ 、ＰＧＭＡはドライエツチ
ング耐性が悪い上に、非常に感度が悪い。又ＣＭＳも感
度が悪い。（ＰＭＭＡより１０倍程度良いが、それでも
２４８ｎｍのＫｒＦレーザで約１ｏＯｏ〜２０ｏＯｍ工
／ｃｎｌ必要（膜厚約Ｏ１・５μｍのとキ））。ＡＺ２
４００は、エーノチング耐性もあシ（ノボラック樹脂で
ある故）、感度も市販・開発されたＤＵＶレジストの中
では最も良いが（２４８ｎｍＫｒＦレーザーで約１ｏｏ
ｍＪ／Ｃ！ｌ（膜厚約１．０μｍのとき））、ＤＵＶ光
で露光したときに、露光後の透過率が小さく、レジスト
がＤＵＶ光を吸収する成分がもともと多量に含まれてい
ることがわかる。CMS (chloromethylated styrene; Toyo Soda) and the like have been proposed. PMMA and PGMA have poor dry etching resistance and very low sensitivity. Also, CMS has poor sensitivity. (Although it is about 10 times better than PMMA, it still requires about 100 to 2000 m/cnl using a 248 nm KrF laser (for a film thickness of about 01.5 μm)). AZ2
400 has the best etching resistance (because it is a novolac resin) and the best sensitivity among the commercially developed DUV resists (approximately 100 nm with a 248 nm KrF laser).
mJ/C! 1 (at a film thickness of approximately 1.0 μm)), when exposed to DUV light, the transmittance after exposure was small, indicating that the resist originally contained a large amount of components that absorb DUV light.
第２図に２４８ｎｍレーザーで照射した場合の紫外分光
曲線を示す。このため、ＡＺ２４００を用いてＤＵＶ光
でパターン形成したときには、光がレジスト中で吸収さ
れるため、コントラストの良好なレジストパターンは形
成できない（たとえば、Ｈ，Ｉｔｏ ら、シンポジウム
オン ＶＬｓＩテクノロジー（Ｓｙｍｐｏ、 ｏｎ
Ｖ Ｌ Ｓ Ｉ Ｔｅｃｈ、）（１９８２） 、 Ｋ、
Ｊ、 ０ｒｖｅｋら、エスピーアイイー（ＳＰＩＥ）
（１９８６）、Ｖ、ＰｏＡら、エスピーアイイー（ＳＰ
ＩＥ）（１９８６））。FIG. 2 shows an ultraviolet spectral curve when irradiated with a 248 nm laser. For this reason, when patterning is performed using DUV light using AZ2400, a resist pattern with good contrast cannot be formed because the light is absorbed in the resist (for example, H. Ito et al., Symposium on VLsI Technology (Sympo, on
VLSI Tech, ) (1982), K.
J, 0rvek et al., SPIE
(1986), V., PoA et al., S.P.
IE) (1986)).
第３図を用いて従来のＡＺ２４００を用いたレジストパ
ターン形成方法を示す。基板１上にＡＺ２４ｏＯを回転
塗布し、厚さ１．５μｍのレジスト膜を得る（第３図ａ
）。つぎに２４８ｎｍのＫｒＦエキシマ・レーザー光４
により選択的にレジスト３を露光４する（第３図ｂ）。FIG. 3 shows a conventional resist pattern forming method using AZ2400. AZ24oO is spin-coated on the substrate 1 to obtain a resist film with a thickness of 1.5 μm (see Fig. 3a).
). Next, 248 nm KrF excimer laser beam 4
Then, the resist 3 is selectively exposed 4 (FIG. 3b).
そして、最後に通常のアルカリ現像処理を施してレジス
トパターン３ａが得られた（第３図Ｃ）。Finally, a normal alkaline development process was performed to obtain a resist pattern 3a (FIG. 3C).
発明が解決しようとする課題
ところが、前述のように従来のＡＺ２４００は下部まで
光が到達しないために、レジストパターン３ａはその形
状が劣化し、たものとなっている。Problems to be Solved by the Invention However, as described above, in the conventional AZ2400, the light does not reach the lower part, so the shape of the resist pattern 3a is deteriorated and becomes stale.
このように光の表面吸収が大きいＡＺ２４００のような
従来のレジストでは、露光をたとえばＫｒＦ２４８ｎｍ
エキシマ・レーザー光のような短波長光源を用いた場合
微細なパターンを形状良く得ることは不可能である。In conventional resists such as AZ2400, which have a large surface absorption of light, the exposure is performed using, for example, KrF248nm.
When using a short wavelength light source such as excimer laser light, it is impossible to obtain a fine pattern with good shape.
すなわち、本発明の目的は従来のレジストにおいてレジ
スト表面での光（特に２４８ｎｍエキシマ・レーザー光
）吸収により発生したレジストパターンの解像度、コン
トラストの劣化が発生していたのを防止することにある
。That is, an object of the present invention is to prevent deterioration of the resolution and contrast of a resist pattern caused by absorption of light (particularly 248 nm excimer laser light) on the resist surface in conventional resists.
課題を解決するだめの手段
本発明は従来のエキシマ・レーザー光等の遠紫外線に対
するパターン形成材料の問題を解決するために、パター
ン形成材料中の樹脂をピリジン又はピリジニウム基を含
む樹脂を用い、さらに光によシ酸を発生する化合物とこ
れらを溶解させる溶媒を用いるものである。Means for Solving the Problem In order to solve the problem of conventional pattern forming materials that are resistant to far ultraviolet rays such as excimer laser light, the present invention uses pyridine or a resin containing a pyridinium group as the resin in the pattern forming material, and further This method uses compounds that generate silicic acid when exposed to light and a solvent that dissolves them.
作 用
本発明に係る、ピリジン又はピリジニウム基を含む樹脂
は、塩基性でしかも遠紫外域に吸収の少ない樹脂である
。Function The resin containing pyridine or pyridinium groups according to the present invention is basic and has little absorption in the far ultraviolet region.
しかるに、この樹轟酸を発生する化合物を添加すれば、
その露光部は酸性となり樹脂のアルカリ性（塩基性）と
中和することになる。従って、この場合には酸性溶液に
よる現像によシネガ型のパターンが得られる。However, if you add a compound that generates this tree acid,
The exposed area becomes acidic and neutralizes the alkalinity (basicity) of the resin. Therefore, in this case, a cinema-type pattern can be obtained by development with an acidic solution.
又、この樹脂にアジド化合物を添加すれば、その露光部
は、アジドと樹脂の反応や結合又は結合状態が生じるこ
とから、もはや酸性溶液には溶解しなくなる。従って、
やはり、この場合にも酸性溶液による現像によりネガ型
のパターイが得られる。Furthermore, if an azide compound is added to this resin, the exposed area will no longer dissolve in the acidic solution due to the reaction, bonding, or bonding state between the azide and the resin. Therefore,
Also in this case, a negative type pattern can be obtained by development with an acidic solution.
いずれの場合においても、本発明に係る樹脂はその２４
ａｎｍ付近の透過性が非常に高いことか６１、
ら、高アスペクト比のレジストパターンが得うレる。In any case, the resin according to the present invention is
A resist pattern with a high aspect ratio can be obtained because of the very high transmittance in the vicinity of 61 nm.
なお、本発明において光により酸を発生する化合物とし
ては、ナフトキノンジアジド化合物、オニウム塩、アジ
ン系化合物などが挙げられるが、もちろんこれらに限ら
ない。In the present invention, compounds that generate acid when exposed to light include naphthoquinone diazide compounds, onium salts, azine compounds, etc., but are not limited to these, of course.
本発明のパターン形成材料を２４８ｎｍのＫｒＦエキシ
マ・レーザー露光に用いることによシ、形状の良い超微
細レジストパターンを形成することができる。By using the pattern forming material of the present invention in 248 nm KrF excimer laser exposure, ultrafine resist patterns with good shapes can be formed.
実施例 以下の組成から成るパターン形成材料を調整した。Example A pattern forming material having the following composition was prepared.
４ＣＨ−ＣＨ２−）−（ｎは整数） ５０９（□Ｎ
２１３ｇ
ｔ
この本発明のパターン形成材料を用いたレジストパター
ン形成方法を第１図で説明する。半導体等の基板１」二
に本発明のパターン形成材料２を回転塗布し、厚さ１．
５μｍのレジスト膜を得る（第１ 図ａ ）。つぎに２
４８ｎｍのＫｒＦエキシマ・レーザー光４によシ、マス
ク５を介して選択的にレジスト２をパルス露光する（第
１図ｂ）。このとき露光部２０は酸が発生し、レジスト
膜中の樹脂のアルカリ成分と中和され、酸性溶液に対し
て不溶となる。そして、最後に通常の酸性溶液にて現像
処理を施し未露光部のみを除去してレジストパターン２
ａが得られた（第１図Ｃ）。なお、このときレジストパ
ターン２ａはマスク設計通りに精度よくコントラストの
良いネガ型の微細パターン（ｏ、３μｍ）であった。な
お、このパターン形成材料はピリジン樹脂であることか
ら工１．チング耐性は良好であった。4CH-CH2-)-(n is an integer) 509(□N
213g t A resist pattern forming method using the pattern forming material of the present invention will be explained with reference to FIG. The pattern forming material 2 of the present invention is spin-coated onto a substrate 1''2 such as a semiconductor to a thickness of 1''.
A resist film of 5 μm is obtained (Fig. 1a). Next 2
The resist 2 is selectively exposed in pulses to a 48 nm KrF excimer laser beam 4 through a mask 5 (FIG. 1b). At this time, acid is generated in the exposed area 20, which is neutralized with the alkaline component of the resin in the resist film, and becomes insoluble in the acidic solution. Finally, a development process is performed using a normal acidic solution to remove only the unexposed areas and resist pattern 2 is applied.
A was obtained (Fig. 1C). At this time, the resist pattern 2a was a negative type fine pattern (o, 3 μm) with high precision and good contrast as designed by the mask. Note that since this pattern forming material is pyridine resin, Step 1. The corrosion resistance was good.
なお、本発明に係る樹脂として以下の如き例が挙げられ
るが、もちろんこれらに限定されることはない。The resin according to the present invention includes the following examples, but is not limited thereto.
（ｍ 、 ｎは整数、Ｒはアルキル基又は水素）本発明
の光による酸を発生する化合物の例として以下が挙げら
れるがこれらに本発明は限定されない。(m, n are integers, R is an alkyl group or hydrogen) Examples of compounds that generate acid by light according to the present invention include the following, but the present invention is not limited thereto.
ｆ Ｃｔ″′ １０へ−ジ 以下の如き例が挙げられるがこれらに限定されない。f Ct″′ Go to 10 Examples include, but are not limited to, the following:
Ｎ ３−ＧＥ＞−ＣＨ２−（）−Ｎ ３なお、本発明に
係る溶媒としては、感光体、樹脂、又、光により酸を発
生させる化合物を溶解させるものであればいずれでも良
いが、例えば、エチルセルソルブアセテート、シクロヘ
キサノン。N 3-GE>-CH2-()-N 3 The solvent according to the present invention may be any solvent as long as it can dissolve the photoreceptor, resin, or a compound that generates an acid when exposed to light. , ethylcellosolve acetate, cyclohexanone.
ジエチレングリコールジメチルエーテル、メチルセルン
ルブアセテート、キシレン、又は、これらのいずれかの
混合物などが挙げられる。もちろん、これらに限定され
ることはない。Examples include diethylene glycol dimethyl ether, methyl selenium acetate, xylene, and mixtures of any of these. Of course, it is not limited to these.
又、本発明に係るアジド化合物としては例えば発明の効
果
本発明によれば、特にＤＵＶ光やエキシマ・レーザー光
による露光・現像に際してのレジメ１−パターン形成が
高コントラスト、高解像、高精度で行うことができ、結
果として半導体素子の微細化。In addition, the azide compound according to the present invention can be used, for example, to achieve the effects of the invention.According to the present invention, especially during exposure and development with DUV light or excimer laser light, Regime 1-pattern formation can be achieved with high contrast, high resolution, and high precision. As a result, miniaturization of semiconductor devices can be achieved.
歩留まり向上につながり、工業的価値が高い。It leads to improved yield and has high industrial value.
第１図は本発明の一実施例のパターン形成材料を用いた
パターン形成方法の工程断面図、第２図は従来のレジス
ｌ−（Ａ、Ｚ ２４００ ）の露光前後のＤＵＶ領域で
の紫外分光曲線図、第３図は従来のパターン形成方法の
工程断面図である。
１・・・・・基板、２・・・・・本発明のパターン形成
材料、４・・・・・・エキシマ・レーサー光、５・・・
・・マスク、３ａ１１ ヘ一／
・・・・・バタFig. 1 is a process cross-sectional view of a pattern forming method using a pattern forming material according to an embodiment of the present invention, and Fig. 2 is an ultraviolet spectroscopy in the DUV region of a conventional resist l-(A, Z 2400) before and after exposure. The curve diagram and FIG. 3 are process cross-sectional views of a conventional pattern forming method. 1...Substrate, 2...Pattern forming material of the present invention, 4...Excimer laser light, 5...
・・Mask, 3a11 Heichi/ ・・・・Bata
Claims (3)
り酸を発生する化合物とこれらを溶解させる溶媒より成
ることを特徴とするパターン形成材料。(1) A pattern forming material comprising a resin containing pyridine or a pyridinium group, a compound that generates an acid when exposed to light, and a solvent for dissolving these.
アジド化合物、オニウム塩、アジン系化合物であること
を特徴とする特許請求の範囲第１項に記載のパターン形
成材料。(2) The pattern forming material according to claim 1, wherein the compound that generates an acid when exposed to light is a naphthoquinone diazide compound, an onium salt, or an azine compound.
化合物とこれらを溶解させる溶媒より成ることを特徴と
するパターン形成材料。(3) A pattern forming material comprising a resin containing pyridine or a pyridinium group, an azide compound, and a solvent for dissolving these.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27345088A JPH02118651A (en) | 1988-10-28 | 1988-10-28 | Pattern forming material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27345088A JPH02118651A (en) | 1988-10-28 | 1988-10-28 | Pattern forming material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02118651A true JPH02118651A (en) | 1990-05-02 |
Family
ID=17528083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27345088A Pending JPH02118651A (en) | 1988-10-28 | 1988-10-28 | Pattern forming material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02118651A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0480758A (en) * | 1990-07-23 | 1992-03-13 | Fuji Photo Film Co Ltd | Photosensitive composition |
| JPH05127369A (en) * | 1991-10-31 | 1993-05-25 | Nec Corp | Resist material |
| JPH05232706A (en) * | 1992-02-25 | 1993-09-10 | Japan Synthetic Rubber Co Ltd | Radiation sensitive resin compound |
| JPH05249662A (en) * | 1991-10-17 | 1993-09-28 | Shipley Co Inc | Radiation-sensitive composition, and its production |
| JPH11223951A (en) * | 1998-11-27 | 1999-08-17 | Jsr Corp | Positive type radiation sensitive resin composition |
| US6994946B2 (en) | 2003-05-27 | 2006-02-07 | Shin-Etsu Chemical Co., Ltd. | Silicon-containing polymer, resist composition and patterning process |
| WO2013141222A1 (en) * | 2012-03-19 | 2013-09-26 | Jsr株式会社 | Resist pattern forming method and photoresist composition |
| US10629349B2 (en) | 2010-05-16 | 2020-04-21 | Gooper Hermeteic Ltd. | Flexible magnetic sealing apparatus |
-
1988
- 1988-10-28 JP JP27345088A patent/JPH02118651A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0480758A (en) * | 1990-07-23 | 1992-03-13 | Fuji Photo Film Co Ltd | Photosensitive composition |
| JPH05249662A (en) * | 1991-10-17 | 1993-09-28 | Shipley Co Inc | Radiation-sensitive composition, and its production |
| JPH05127369A (en) * | 1991-10-31 | 1993-05-25 | Nec Corp | Resist material |
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| US10629349B2 (en) | 2010-05-16 | 2020-04-21 | Gooper Hermeteic Ltd. | Flexible magnetic sealing apparatus |
| US11270823B2 (en) | 2010-05-16 | 2022-03-08 | Gooper Hermetic Ltd | Flexible magnetic sealing apparatus |
| US11600418B2 (en) | 2010-05-16 | 2023-03-07 | Gooper Hermetic, Ltd. | Flexible magnetic sealing apparatus |
| WO2013141222A1 (en) * | 2012-03-19 | 2013-09-26 | Jsr株式会社 | Resist pattern forming method and photoresist composition |
| JPWO2013141222A1 (en) * | 2012-03-19 | 2015-08-03 | Jsr株式会社 | Resist pattern forming method and photoresist composition |
| US9594303B2 (en) | 2012-03-19 | 2017-03-14 | Jsr Corporation | Resist pattern-forming method and photoresist composition |
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