JPH01101308A - Silicon atom-containing ethylenic polymer, composition containing said polymer and method for use thereof - Google Patents
Silicon atom-containing ethylenic polymer, composition containing said polymer and method for use thereofInfo
- Publication number
- JPH01101308A JPH01101308A JP62258435A JP25843587A JPH01101308A JP H01101308 A JPH01101308 A JP H01101308A JP 62258435 A JP62258435 A JP 62258435A JP 25843587 A JP25843587 A JP 25843587A JP H01101308 A JPH01101308 A JP H01101308A
- Authority
- JP
- Japan
- Prior art keywords
- resist
- polymer
- layer
- pattern
- organic film
- 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
- 238000000034 method Methods 0.000 title claims abstract description 26
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 18
- 239000000203 mixture Substances 0.000 title claims abstract description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims description 21
- 229920000642 polymer Polymers 0.000 title abstract description 31
- 238000001312 dry etching Methods 0.000 claims abstract description 13
- 239000000758 substrate Substances 0.000 claims abstract description 11
- 229920000573 polyethylene Polymers 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims 3
- 230000035945 sensitivity Effects 0.000 abstract description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- FSAONUPVUVBQHL-UHFFFAOYSA-N 1,3-bis(4-azidophenyl)prop-2-en-1-one Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C=CC(=O)C1=CC=C(N=[N+]=[N-])C=C1 FSAONUPVUVBQHL-UHFFFAOYSA-N 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000010410 layer Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 238000010894 electron beam technology Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000000059 patterning Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005530 etching Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000000992 sputter etching Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000000609 electron-beam lithography Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000010884 ion-beam technique Methods 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- 241000282461 Canis lupus Species 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- QLDYTACVSNAPTO-UHFFFAOYSA-N [N-]=[N+]=NSN=[N+]=[N-] Chemical compound [N-]=[N+]=NSN=[N+]=[N-] QLDYTACVSNAPTO-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000001803 electron scattering Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- -1 polydimethylsiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000008096 xylene Substances 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
- G03F7/0758—Macromolecular compounds containing Si-O, Si-C or Si-N bonds with silicon- containing groups in the side chains
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明はケイ素原子含有エチレン系重合体およびこの重
合体を含むレジスト組成物およびその使用方法に関し、
特に半導体集積回路、磁気バブルメモリ等の微細パター
ン形成法に適したケイ素原子含有エチレン系重合体およ
びレジスト組成物およびパターン形成方法に関する。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a silicon atom-containing ethylene polymer, a resist composition containing this polymer, and a method for using the same.
In particular, the present invention relates to silicon atom-containing ethylene polymers, resist compositions, and pattern forming methods suitable for forming fine patterns in semiconductor integrated circuits, magnetic bubble memories, and the like.
［従来の技術］
集積回路、バブルメモリ素子などの製造において光学的
リソグラフィまたは電子ビームリソグラフィを用いて微
細なパターンを形成する際、光学的リソグラフィにおい
ては基板からの反射波の影響、電子ビームリソグラフィ
においては電子散乱の影響によりレジストが厚い場合は
解像度が低下することが知られている。現像により得ら
れたレジストパターンを精度よく基板に転写するために
、ドライエツチングが用いられるが、高解像度のレジス
トパターンを得るために、薄いレジスト層を使用すると
、ドライエツチングによりレジストもエツチングされ基
板を加工するための十分な耐性を示さないという不都合
さがある。また、段差部（おいては、この段差を平坦化
するために、レジスト層を厚く塗る必要が生じ、かかる
レジスト層に微細なパターンを形成することは著しく困
難であるといえる。[Prior Art] When forming fine patterns using optical lithography or electron beam lithography in the manufacture of integrated circuits, bubble memory devices, etc., in optical lithography, the influence of reflected waves from the substrate, and in electron beam lithography, It is known that the resolution decreases when the resist is thick due to the effects of electron scattering. Dry etching is used to accurately transfer the resist pattern obtained by development onto the substrate. However, if a thin resist layer is used to obtain a high-resolution resist pattern, the resist will also be etched by dry etching and the substrate will be etched. It has the disadvantage that it does not exhibit sufficient resistance for processing. Furthermore, in order to flatten the stepped portion, it is necessary to apply a thick resist layer, and it is extremely difficult to form a fine pattern on such a resist layer.
かかる不都合さを解決するために三層構造レジストがジ
エイ・エム・モラン（Ｊ、Ｈ，Ｍｏｒａｎ）らによって
シレーナル・オブ・バキューム・サイエンス・アンド・
テクノロジー（Ｊ、 Ｖａｃｕｕ＋ｎ ５ｃｉｅｎｃｅ
ａｎｄ Ｔｅｃｈｎｏｌｏｃ＋ｙ） 、第１６巻、１６
２０ページ（１９乃年）に提案されている。三層構造に
おいては、第一層（最下層）に厚い有機層を塗１５Ｌ、
たのち中間層としてシリコン酸化膜、シリコン窒化膜、
シリコン膜などのように０２を使用するドライエツチン
グにおいて蝕刻され難い無機物質材料を形成する。In order to solve these inconveniences, a three-layer resist was developed by J. H. Moran et al.
Technology (J, Vacuu+n 5science
and Technoloc+y), Volume 16, 16
It is proposed on page 20 (2019). In the three-layer structure, the first layer (bottom layer) is coated with a thick organic layer of 15L,
Later, silicon oxide film, silicon nitride film,
An inorganic material, such as a silicon film, which is difficult to be etched by dry etching using 02 is formed.
しかる後、中間層の上にレジストをスピン塗布し、電子
ビームや光によりレジストを露光、現像する。Thereafter, a resist is spin-coated onto the intermediate layer, and the resist is exposed and developed using an electron beam or light.
得へれたレジストパターンをマスクに中間層をドライエ
ツチングし、しかる後、この中間層をマスクに第一層の
厚い有機層を０２を用いた反応性スパッタエツチング法
によりエツチングする。この方法により薄い高解像度の
レジストパターンを厚い有機層のパターンに変換するこ
とができる。しかしながら、このような方法においては
第一層を形成した後、中間層を蒸着法、スパッタ法ある
いはプラズマＣｖＤ法により形成し、ざらにパターニン
グ用レジストを塗布するため工程が複雑で、かつ長くな
るという欠点がある。Using the obtained resist pattern as a mask, the intermediate layer is dry etched, and then, using this intermediate layer as a mask, the first thick organic layer is etched by a reactive sputter etching method using 02. This method allows converting thin high-resolution resist patterns into thick organic layer patterns. However, in this method, after forming the first layer, the intermediate layer is formed by vapor deposition, sputtering, or plasma CVD, and the patterning resist is roughly applied, making the process complicated and long. There are drawbacks.
パターニング用レジストがドライエツチングに対して強
ければ、パターニング用レジストをマスクに厚い有機層
をエツチングすることができるので、二層構造とするこ
とができ工程を簡略化することができる。If the patterning resist is resistant to dry etching, a thick organic layer can be etched using the patterning resist as a mask, resulting in a two-layer structure and simplifying the process.
［発明が解決しようとする問題点］
ポリジメチルシロキサンは酸素反応性イオンエツチング
（０２ＲＩＥ＞に対して耐性が著しく優れ、エツチング
レートはほぼ零であることは公知である（ジー エヌ
テーラ−、ティー エムウオルフ アンド ジエー エ
ム モラン、ジャーナル オブ バキューム サイエン
ス アンドテクノロジー、 １９（４）、 ８７２．１
９８１（Ｇ、Ｎ、ｒａｙｌｏｒ。[Problems to be Solved by the Invention] It is known that polydimethylsiloxane has extremely high resistance to oxygen-reactive ion etching (02RIE) and has an etching rate of almost zero (G.N.
Taylor, T. M. Wolf and G. M. Moran, Journal of Vacuum Science and Technology, 19(4), 872.1.
981 (G, N, Raylor.
Ｔ、）１． Ｗｏｌｆ ａｎｄ Ｊ、Ｈ１４ｏｒ
ａｎ、 Ｊ、Ｖａｃｕｕｍ Ｓｃｉ、 ａｎｄＴ
ｅｃｈ、、１９（４）、 ８７２．１９８１））が、こ
のポリマーハ常温で液状であるので、はこりが付着しや
すく、高解像度が得にくいなどの欠点がありレジスト材
料としては適さない。T,)1. Wolf and J, H14or
an, J., Vacuum Sci, and T.
ech, 19(4), 872.1981)), but since this polymer is liquid at room temperature, it has drawbacks such as easy adhesion of flakes and difficulty in obtaining high resolution, making it unsuitable as a resist material.
われわれはすでに上記パターニング用レジストとしてト
リアルキルシリルスチレンの単独重合体および共重合体
を提案した［特願昭５７−１２３８６６＠（特開昭５９
−１５４１９＠公報）、特願昭５７−１２３８６５＠（
特開昭５９−１５２４３号公報）］。しかしこれらの重
合体は遠紫外もしくは電子ビーム露光に対する感度は優
れているので遠紫外用もしくは電子ビーム露光用レジス
トとしては適しているが、近紫外および可視光の露光に
対しては架橋ぜず、フォト用レジストとして使用できな
かった。We have already proposed homopolymers and copolymers of trialkylsilylstyrene as the above-mentioned patterning resists [Japanese Patent Application No. 57-123866
-15419@publication), patent application No. 57-123865@(
JP-A-59-15243)]. However, these polymers have excellent sensitivity to far ultraviolet or electron beam exposure and are suitable as resists for far ultraviolet or electron beam exposure, but they do not crosslink when exposed to near ultraviolet or visible light. It could not be used as a photoresist.
また、われわれはすでに上記パターニングの光学露光用
レジストとしてシラン系重合体を提供した（特願昭６０
−００１６３６号、特願昭６０−００１６３７＠ ）。In addition, we have already provided a silane polymer as a resist for optical exposure for the above-mentioned patterning (patent application filed in 1983).
-001636, patent application No. 1983-001637@).
しかしここで提供したレジストはシリコン原子濃度が重
合体に対して約１０〜１３％（Ｗ／Ｗ）なので下層が厚
い場合、たとえば下層の膜厚が１，５期以上では上記パ
ターニング用の上層としてドライエツチング耐性は不十
分であった。However, the resist provided here has a silicon atom concentration of about 10 to 13% (W/W) relative to the polymer, so if the lower layer is thick, for example, if the thickness of the lower layer is 1.5 or more, it cannot be used as the upper layer for patterning. Dry etching resistance was insufficient.
本発明の目的は、電子線、Ｘ線、遠紫外線、イオンビー
ムあるいはこれらに加えて近紫外線に対しても非常に高
感度で微細パターンが形成でき、しかもドライエツチン
グに対してより強い耐性をもつ重合体、およびそれを含
む組成物、およびその使用方法を提供することにある。The object of the present invention is to be able to form fine patterns with extremely high sensitivity to electron beams, X-rays, deep ultraviolet rays, ion beams, or near ultraviolet rays in addition to these, and to have greater resistance to dry etching. An object of the present invention is to provide a polymer, a composition containing the same, and a method for using the same.
−
［問題点を解決するための手段］
本発明者らは、このような状況に鑑みて研究を続けた結
果、重合体の単量体ユニット中にシリコン原子を２個有
すると共にアリル基を有すると、画素による反応性スパ
ッタエツチングに対して極めて強く、厚い有機膜をエツ
チングする際のマスクになること、また、電子線、Ｘ線
、遠紫外線、イオンビームに対して非常に高感度である
こと、ざらにビスアジド化合物を添加すると近紫外線に
対しても非常に高感度となることを見出し、本発明をな
すに至った。- [Means for solving the problem] As a result of continuing research in view of the above situation, the present inventors found that the monomer unit of the polymer has two silicon atoms and an allyl group. This means that it is extremely resistant to reactive sputter etching caused by pixels, can be used as a mask when etching thick organic films, and is extremely sensitive to electron beams, X-rays, deep ultraviolet rays, and ion beams. They discovered that when a bisazide compound is added to zara, the sensitivity to near ultraviolet light becomes extremely high, and the present invention has been completed.
すなわら本発明は主鎖が下記の構造単位で構成されたこ
とを特徴とする分子量３０００〜１００００００のケイ
素原子含有エチレン系重合体、
Ｃｈ ＣＨ３
前記ケイ素原子含有エチレン系重合体とビスアジドより
なるレジスト組成物、および基板上に有機膜および所定
のレジストパターンを有するレジスト層を順に形成し、
このレジストパターンを有機膜に対するドライエツチン
グマスクとして用いる２層構造レジスト法によるパター
ン形成方法において、前記レジスト層が前記ケイ素原子
含有エチレン系重合体またはこの重合体とごスアジドよ
りなる組成物で形成されていることを特徴とするパター
ン形成方法である。That is, the present invention provides a silicon atom-containing ethylene polymer having a molecular weight of 3,000 to 1,000,000, whose main chain is composed of the following structural units, Ch CH3 and a resist comprising the silicon atom-containing ethylene polymer and bisazide. sequentially forming an organic film and a resist layer having a predetermined resist pattern on the composition and the substrate;
In a pattern forming method using a two-layer resist method in which this resist pattern is used as a dry etching mask for an organic film, the resist layer is formed of the silicon atom-containing ethylene polymer or a composition of this polymer and sulfur azide. This is a pattern forming method characterized by the following.
重合体は一般にネガ型レジストとして用いた場合、高分
子量であれば高感度となるが現像時の膨潤により解像度
を損う。通例、分子母百万を超えるものは、高い解像性
を期待できない。一方、分子量を小さくすることは解像
性を向上させるが、感度は分子量に比例して低下して実
用性を失うだけでなく、分子量玉子以下では均一で堅固
な影形成が難しくなるという問題がある。したがってケ
イ素原子含有エチレン系重合体の分子量は３０００〜１
００００００の範囲のものが適当である。Generally, when a polymer is used as a negative resist, if it has a high molecular weight, it will have high sensitivity, but the resolution will be impaired due to swelling during development. Generally, if the number of molecules exceeds one million, high resolution cannot be expected. On the other hand, reducing the molecular weight improves resolution, but not only does the sensitivity decrease in proportion to the molecular weight, making it impractical, but there is also the problem that it becomes difficult to form uniform and solid shadows when the molecular weight is lower than that of an egg. be. Therefore, the molecular weight of the silicon atom-containing ethylene polymer is 3000-1
A value in the range of 000000 is suitable.
本発明のケイ素原子含有エチレン系重合体は例えば次の
ようにして製造することができる。The silicon atom-containing ethylene polymer of the present invention can be produced, for example, as follows.
（以下余白）
ヘキサン中、 ２０℃
上式で示した様に、本発明の重合体はｎ−ブチルリチウ
ム（ｎ−ＢｕＬｉ）を用いたアニオン重合法によって、
多分散度の小さい、そして低分子量がら高分子量の任意
の分子量の重合体を製造することができる。(Blank below) In hexane at 20°C As shown in the above formula, the polymer of the present invention is produced by an anionic polymerization method using n-butyllithium (n-BuLi).
Polymers of any molecular weight can be produced with low polydispersity and from low to high molecular weights.
この重合体は一般の有機溶剤、例えばヘキサン、ベンゼ
ン、メチルエチルケトン、クロロホルム等に可溶で、メ
タノール、エタノールには不溶である。This polymer is soluble in common organic solvents such as hexane, benzene, methyl ethyl ketone, chloroform, etc., and insoluble in methanol and ethanol.
本発明におけるレジスト材料はそのままで電子線、Ｘ線
、遠紫外線に対して極めて高感度であるが、光架橋剤と
して知られているビスアジドを添加すると紫外線に対し
ても高感度なレジストとなる。本発明で用いられるビス
アジドとしては、４．４゛−ジアジドカルコン、２，６
−ジー（４゛−アジドベンザル）シクロヘキサノン、２
．６−ジー（４°−アジドベンザル）−４−メチルシク
ロヘキサノン、２．６−ジー（４°−アジドベンザル）
−４−ハイドロオキシシクロヘキサノンなどが挙げられ
る。光架橋剤の添加量は、過少または過大であると紫外
線に。The resist material in the present invention is extremely sensitive to electron beams, X-rays, and deep ultraviolet rays as it is, but when bisazide, which is known as a photocrosslinking agent, is added, the resist becomes highly sensitive to ultraviolet rays. The bisazides used in the present invention include 4.4゛-diazide chalcone, 2,6
-Z(4'-azidobenzal)cyclohexanone, 2
．． 6-di(4°-azidobenzal)-4-methylcyclohexanone, 2.6-di(4°-azidobenzal)
-4-hydroxycyclohexanone and the like. If the amount of photo-crosslinking agent added is too little or too much, it will cause UV rays.
対する感度が低下し、また過大に添加した組成物は０２
のドライエツチングに対する耐性を悪くするので、重合
体に対して０゜１〜３０重量％加えることが望ましい。The sensitivity to
It is desirable to add 0.1 to 30% by weight of the polymer since it deteriorates its resistance to dry etching.
分子量分布の均一性も解像性に影響を与えることが知ら
れており、多分散度が小ざいほど良好な解像を示す。こ
の点、アニオン重合法から製造される上記の方法は、分
子量分別せずに、直接多分散度の小さい、たとえば１，
２もしくはそれ以下の重合体が得られるので、そのレジ
スト材料は優れた解像性を有する。It is known that the uniformity of molecular weight distribution also affects resolution, and the smaller the polydispersity, the better the resolution. In this respect, the above-mentioned method of manufacturing from an anionic polymerization method directly produces products with low polydispersity, such as 1,
Since a polymer of 2 or less is obtained, the resist material has excellent resolution.
［実施例］ 次に本発明を実施例によって説明する。[Example] Next, the present invention will be explained by examples.
５００７！フラスコに１，３−ジクロロテトラメチルシ
ロキリン４０．６Ｃ７（０，２モル）とエチルエーテル
２００ｄを仕込み、アリルマグネシウムブロマイド（エ
ーテル中） ２９０ （０，２モル）を穏やかな還流状
態で滴下した。滴下終了後、固形物をガラスフィルタを
用いてろ過して除いた。エーテル留出後、残留物を蒸留
して目的化合物を得た。収量は９．７０（３２％）であ
った。5007! A flask was charged with 1,3-dichlorotetramethylsiloquiline 40.6C7 (0.2 mol) and ethyl ether 200d, and allylmagnesium bromide (in ether) 290 (0.2 mol) was added dropwise under mild reflux. After the dropping was completed, solid matter was removed by filtration using a glass filter. After distilling off the ether, the residue was distilled to obtain the target compound. Yield was 9.70 (32%).
原料製造例２１−アリル−３−ビニルナトラメ３００ｄ
フラスコにマグネシウム４．８０（０，２グラム原子）
およびテトラヒドロフラン（ＴＩ−ＩＦ＞３０ｄを仕込
み、少量の臭化エチルを加えて加熱した。Raw material production example 21-allyl-3-vinylnatrame 300d
Magnesium 4.80 (0,2 gram atom) in the flask
and tetrahydrofuran (TI-IF>30d), and a small amount of ethyl bromide was added and heated.
室温に戻した後、臭化ビニル２１．４ｇ（０，２モル）
のＴＨＦ５０ｍ溶液を１時間を要して加えた。さらに還
流状態で４時間反応を続けた後、室温まで冷却した。別
の３００ｄフラスコに原料製造例１で製造した１−アリ
ル−３−クロロテトラメチルシロキサン２２．８Ｑ （
０，１５モル）およびＴＨＦ５０ｄを仕込んだ。還流状
態にし、上記で製造したグリニヤール試薬を１時間を要
して滴下して加えた。ざらに１時間、還流状態で反応を
続けた後、室温まで冷却した。反応溶液を希■α溶液中
に投入し、エーテル５００ｍ１を加えて抽出を行った。After returning to room temperature, 21.4 g (0.2 mol) of vinyl bromide
A 50 m THF solution of was added over a period of 1 hour. The reaction was further continued under reflux for 4 hours, and then cooled to room temperature. In another 300d flask, 1-allyl-3-chlorotetramethylsiloxane 22.8Q (
0.15 mol) and THF50d were charged. The mixture was brought to reflux and the Grignard reagent prepared above was added dropwise over a period of 1 hour. The reaction was continued under reflux for approximately 1 hour, and then cooled to room temperature. The reaction solution was poured into a dilute α solution, and 500 ml of ether was added to perform extraction.
エーテル層を硫酸マグネシウムで乾燥後、エーテルを留
出し、残貿物を蒸留して目的化合物６Ｇｌ（２０％）を
得た。After drying the ether layer with magnesium sulfate, the ether was distilled off and the residue was distilled to obtain the target compound 6Gl (20%).
実施例１
原料製造例２で合成した単量体およびＴＨＥを水素化カ
ルシウムで予備乾燥した。以下に述べる重合反応はすべ
て高真空下で行った。Example 1 The monomer synthesized in Raw Material Production Example 2 and THE were preliminarily dried with calcium hydride. All polymerization reactions described below were performed under high vacuum.
原料製造例２で製造した単量体１１ｑを１０（７！枝付
きフラスコに仕込み、枝をラバーセプタムで封をし、フ
ラスコを高真空ラインに接続した。液体窒素浴で凍結し
てから、減圧にし、液体状態に戻した。この操作を４回
繰返して単量体中に含まれる空気を脱気した後、ｎ−ブ
チルリチウム（１，６Ｍ：ヘキサン中＞０．５ｄを加え
て単量体を完全脱水した。その後、同様の枝付きフラス
コへ蒸留した。Ｔ ＨＥ ５０ｄも同様に脱気、脱水を
行い重合フラスコへ蒸留した。室温にてラバーセプタム
からミクロシリンジを用いてｎ−ブチルリチウム（１，
６Ｍ ：ヘキサン中）８０μ！を加え、すぐにアセトン
−ドライアイス浴で冷却させて重合を行つた。２時間後
、メタノール１ｍｉをシリンジを用いて加え、重合を停
止した後、常圧に戻し、重合体溶液を５００ｄのメタノ
ール中に投入した。重合体は白色固体となって析出し、
ろ過して分離した。Monomer 11q produced in Raw Material Production Example 2 was charged into a flask with 10 (7! branches), the branches were sealed with a rubber septum, and the flask was connected to a high vacuum line. After freezing in a liquid nitrogen bath, the This operation was repeated four times to degas the air contained in the monomer, and then n-butyllithium (1,6M:>0.5d in hexane was added to dissolve the monomer. was completely dehydrated. Thereafter, it was distilled into a similar side flask. T HE 50d was similarly degassed and dehydrated and distilled into a polymerization flask. At room temperature, n-butyllithium ( 1,
6M: in hexane) 80μ! was added and immediately cooled in an acetone-dry ice bath to carry out polymerization. After 2 hours, 1 ml of methanol was added using a syringe to stop polymerization, the pressure was returned to normal pressure, and the polymer solution was poured into 500 ml of methanol. The polymer precipitates as a white solid,
It was separated by filtration.
ざらにベンゼン１００威に溶解させ、メタノール５００
ｄに投入した。この操作を３回繰返した後、減圧下５０
’Ｃで乾燥した。目的化合物の収量は１０，７ｑ（はぼ
１００％）であった。Dissolve coarsely in 100 parts of benzene and 500 parts of methanol.
I put it into d. After repeating this operation three times,
It was dried at 'C. The yield of the target compound was 10.7q (approximately 100%).
重１平均分子量（ＭＷ ） ＝３１，０００故平均分子
ｆｆｌ （Ｍｎ ） ＝３０，０００多分散度（Ｍｗ／
Ｍｎ）＝ １．０３
この重合体は一つの単位の中にシリコン原子を２個有し
ているためシリコン含有量は重合体全体に対して２８，
０％（−／Ｗ）となる。Average molecular weight (MW) = 31,000 Average molecular weight (Mn) = 30,000 Polydispersity (Mw/
Mn) = 1.03 This polymer has two silicon atoms in one unit, so the silicon content is 28,
It becomes 0% (-/W).
得られた重合体１０Ｃ１を５００ｍ１のメチルエチルケ
トンに溶かし、メタノール７０ｍ１を少しずつ加えた。The obtained polymer 10C1 was dissolved in 500 ml of methyl ethyl ketone, and 70 ml of methanol was added little by little.
ｊｑられた白濁液を一夜放置後、デカンテーションして
下層に沈んだポリマー溶液をベンゼン１００ｄに溶かし
、５０ｄのメタノール中に投入した。その結果、白色の
固体が得られ、ろ過して減圧下で乾燥し、フラクション
１とした。さらにデカンテーション後の上ｔＵみ液にメ
タノール３０ｄを加え上記と同様にして２回目の分子量
分別を行った。さらに同量のメタノールを加えて同様に
行い３回目の分子量分別を行った。The white cloudy liquid was left overnight, then decanted, and the polymer solution that had sunk to the bottom layer was dissolved in 100 d of benzene and poured into 50 d of methanol. As a result, a white solid was obtained, which was filtered and dried under reduced pressure to obtain fraction 1. Furthermore, 30 d of methanol was added to the upper tU liquid after decantation, and a second molecular weight fractionation was carried out in the same manner as above. Furthermore, the same amount of methanol was added and the same procedure was carried out for a third molecular weight fractionation.
実施例２
実施例１で製造した重合体０．４２０と２，６−ジー（
４°−アジドベンザル）−４−メチルシクロへキサノン
０．０２１ ＣＪをキシレン６、 （７に溶解し、十分
撹拌した後、０．２ｐｔｎのフィルタでろ過し、試料溶
液とした。この溶液をシリコン基板上にスピン塗布（３
００Ｏｒｐｍ） Ｌ、８０℃、３０分間乾燥を行った。Example 2 Polymer 0.420 produced in Example 1 and 2,6-G(
0.021 CJ of 4°-azidobenzal)-4-methylcyclohexanone was dissolved in xylene 6, (7), thoroughly stirred, and then filtered through a 0.2 ptn filter to obtain a sample solution. This solution was placed on a silicon substrate. Spin coating (3)
Drying was performed at 80° C. for 30 minutes.
紫外線露光装置（１４ＡＮＮ ４８００ ＤＳＷ （Ｇ
ＣＡ社製））を用いて、クロムマスクを介して露光を行
った。Ultraviolet exposure equipment (14ANN 4800 DSW (G
Exposure was performed using a chrome mask (manufactured by CA) through a chrome mask.
メチルイソブチルケトン（）ＩＩＢＫ）に１分間浸漬し
て現像を行った後、イソプロパツールにて１分間リンス
を行った。乾燥したのち、被照射部の膜厚を触針法によ
り測定した。初期膜厚は０．２５．ｃｓであった。微細
なパターンを解像しているが否かは種々の寸法のライン
アンドスペースのパターンを描画し、現像処理によって
得られたレジスト像を光学顕微鏡、走査型電子顕微鏡で
観察することによって調べた。After developing by immersing it in methyl isobutyl ketone (IIBK) for 1 minute, it was rinsed with isopropanol for 1 minute. After drying, the film thickness of the irradiated area was measured using a stylus method. The initial film thickness is 0.25. It was cs. Whether fine patterns were resolved or not was determined by drawing line-and-space patterns of various sizes and observing the resist images obtained by development using an optical microscope or a scanning electron microscope.
感度曲線からゲル化点（Ｄ５ ＞が約０．９４秒である
ことがわかった。紫外線露光でひろく用いられているフ
ォトレジストであるシプレー社ＭＰ−１３００、（１＃
Ｉ厚）の適正露光量は０．３８秒であった。From the sensitivity curve, it was found that the gel point (D5>) was approximately 0.94 seconds.
The appropriate exposure amount for the film (I thickness) was 0.38 seconds.
実施例３
シリコン基板上にノボラック樹脂を主成分とするレジス
ト材料（）ｆＰ−１３００（シプレー社製））を厚さ１
．５期塗布し、２５０℃において１時間焼きしめを行っ
た。しかる後、実施例２で調整した溶液をスピン塗布し
、８０℃にて３０分間乾燥を行って０．２５１ＩＩｎ厚
の均一な塗膜を得た。この基板を紫外線露光装置（４８
０００Ｓ誓（ＧＣＡ社製〉）を用いクロムマスクを介し
てｉｏ、ｏ秒置光した。）ｆｌＢＫ／ｎ−ＢｕＯＨ（５
０／１００Ｖ／Ｖ）に１分間浸漬して現像を行ったのち
、イソプロパツールにて１分間リンスを行った。この基
板を平行平板の反応性スパッタエツチング装置（アネル
バ社製ＤＥＮ−４５１＞を用い、０２２ｓｅｃｍ。Example 3 A resist material () fP-1300 (manufactured by Shipley) containing novolac resin as the main component was deposited on a silicon substrate to a thickness of 1
．． It was coated for 5 times and baked at 250°C for 1 hour. Thereafter, the solution prepared in Example 2 was spin-coated and dried at 80° C. for 30 minutes to obtain a uniform coating film with a thickness of 0.251 IIn. This substrate was exposed to ultraviolet exposure equipment (48
Using 000S (manufactured by GCA), light was exposed for io and o seconds through a chrome mask. ) flBK/n-BuOH (5
0/100V/V) for 1 minute to perform development, and then rinsed with isopropanol for 1 minute. This substrate was etched for 022 seconds using a parallel plate reactive sputter etching device (DEN-451 manufactured by Anelva).
３、ＯＰａ、 ０．１６Ｗ／ｃｍ２の条件で２５分間エ
ツチングを行った。走査型電子顕微鏡で観察した結果、
サブミクロンの上層のパターンが下層レジスト材料によ
り正確に転写され、より垂直なパターンが形成されてい
ることがわかった。Etching was performed for 25 minutes under the conditions of 3. OPa and 0.16 W/cm2. As a result of observation with a scanning electron microscope,
It was found that the submicron upper layer pattern was accurately transferred by the lower layer resist material, forming a more vertical pattern.
［発明の効果］
以上説明したように、本発明の重合体は１構造単位当り
シリコン原子を２個有しているため、高いシリコン濃度
、すなわち２８．０％四／Δ）となる。[Effects of the Invention] As explained above, since the polymer of the present invention has two silicon atoms per structural unit, it has a high silicon concentration, that is, 28.0% 4/Δ).
そのためレジスト組成物はドライエツチングに対して極
めて強く、２０００人程度０膜厚があれば、１．５ｐｔ
ｎ程度の厚い有機層をエツチングするためのマスクにな
り得る。したがって、パターン形成用のレジスト膜は薄
くてよい。また、下地に厚い有機層があると電子ビーム
露光においては近接効果が低減されるため、また光学露
光においては反射波の悪影響が低減されるために、高解
像度のパターンが容易に得られる。また他の露光法にお
いても高解像度のパターンが容易に得られる。Therefore, the resist composition is extremely resistant to dry etching, and if there is a zero film thickness of about 2,000
It can be used as a mask for etching an organic layer as thick as n. Therefore, the resist film for pattern formation may be thin. Furthermore, a thick organic layer on the base reduces the proximity effect in electron beam exposure, and reduces the adverse effects of reflected waves in optical exposure, making it easy to obtain a high-resolution pattern. Also, high-resolution patterns can be easily obtained using other exposure methods.
ざらに本発明の重合体をアニオン重合法により合成した
場合には分子量分布の多分散度が小さいものが得られ、
そのため前記重合体とビスアジドとの組成物をレジスト
として用いたとき、得られるパターンの解像度はより優
れたものとなる。In general, when the polymer of the present invention is synthesized by an anionic polymerization method, a polymer with a small polydispersity of molecular weight distribution can be obtained,
Therefore, when the composition of the polymer and bisazide is used as a resist, the resolution of the resulting pattern is even better.
Claims (4)
する分子量３０００〜１００００００のケイ素原子含有
エチレン系重合体。 ▲数式、化学式、表等があります▼(1) A silicon atom-containing ethylene polymer having a molecular weight of 3,000 to 1,000,000, whose main chain is composed of the following structural units. ▲Contains mathematical formulas, chemical formulas, tables, etc.▼
０〜１００００００のケイ素原子含有エチレン系重合体
と、 ▲数式、化学式、表等があります▼ ビスアジドよりなることを特徴とするレジスト組成物。(2) Molecular weight 300 with main chain composed of the following structural units
A resist composition characterized by comprising an ethylene polymer containing 0 to 1,000,000 silicon atoms, and ▲numerical formula, chemical formula, table, etc.▼ bisazide.
有するレジスト層を順に形成し、このレジストパターン
を有機膜に対するドライエッチングマスクとして用いる
２層構造レジスト法によるパターン形成方法において、
前記レジスト層が、主鎖が下記の構造単位で構成された
分子量３０００〜１００００００のケイ素原子含有エチ
レン系重合体で形成されていることを特徴とするパター
ン形成方法。 ▲数式、化学式、表等があります▼(3) A pattern forming method using a two-layer resist method in which an organic film and a resist layer having a predetermined resist pattern are sequentially formed on a substrate, and this resist pattern is used as a dry etching mask for the organic film,
A pattern forming method characterized in that the resist layer is formed of a silicon atom-containing ethylene polymer having a molecular weight of 3,000 to 1,000,000 and whose main chain is composed of the following structural units. ▲Contains mathematical formulas, chemical formulas, tables, etc.▼
有するレジスト層を順に形成し、このレジストパターン
を有機膜に対するドライエッチングマスクとして用いる
２層構造レジスト法によるパターン形成方法において、
前記レジスト層が、主鎖が下記の構造単位で構成された
分子量３０００〜１００００００のケイ素原子含有エチ
レン系重合体と、▲数式、化学式、表等があります▼ ビスアジドよりなる組成物で形成されていることを特徴
とするパターン形成方法。(4) A pattern forming method using a two-layer resist method, in which an organic film and a resist layer having a predetermined resist pattern are sequentially formed on a substrate, and this resist pattern is used as a dry etching mask for the organic film,
The resist layer is formed of a composition consisting of a silicon atom-containing ethylene polymer with a molecular weight of 3,000 to 1,000,000 whose main chain is composed of the following structural units, and a bisazide. A pattern forming method characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62258435A JPH0615582B2 (en) | 1987-10-15 | 1987-10-15 | Silicon atom-containing ethylene polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62258435A JPH0615582B2 (en) | 1987-10-15 | 1987-10-15 | Silicon atom-containing ethylene polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01101308A true JPH01101308A (en) | 1989-04-19 |
| JPH0615582B2 JPH0615582B2 (en) | 1994-03-02 |
Family
ID=17320165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62258435A Expired - Lifetime JPH0615582B2 (en) | 1987-10-15 | 1987-10-15 | Silicon atom-containing ethylene polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0615582B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007026010A3 (en) * | 2005-09-01 | 2007-06-14 | Freescale Semiconductor Inc | Semiconductor device including a coupled dielectric layer and metal layer, method of fabrication thereof, and material for coupling a dielectric layer and a metal layer in a semiconductor device |
| US7803719B2 (en) | 2006-02-24 | 2010-09-28 | Freescale Semiconductor, Inc. | Semiconductor device including a coupled dielectric layer and metal layer, method of fabrication thereof, and passivating coupling material comprising multiple organic components for use in a semiconductor device |
-
1987
- 1987-10-15 JP JP62258435A patent/JPH0615582B2/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007026010A3 (en) * | 2005-09-01 | 2007-06-14 | Freescale Semiconductor Inc | Semiconductor device including a coupled dielectric layer and metal layer, method of fabrication thereof, and material for coupling a dielectric layer and a metal layer in a semiconductor device |
| US7691756B2 (en) | 2005-09-01 | 2010-04-06 | Nxp B.V. | Semiconductor device including a coupled dielectric layer and metal layer, method of fabrication thereof, and material for coupling a dielectric layer and a metal layer in a semiconductor device |
| US7951729B2 (en) | 2005-09-01 | 2011-05-31 | Nxp B.V. | Semiconductor device including a coupled dielectric layer and metal layer, method of fabrication thereor, and material for coupling a dielectric layer and a metal layer in a semiconductor device |
| US7803719B2 (en) | 2006-02-24 | 2010-09-28 | Freescale Semiconductor, Inc. | Semiconductor device including a coupled dielectric layer and metal layer, method of fabrication thereof, and passivating coupling material comprising multiple organic components for use in a semiconductor device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0615582B2 (en) | 1994-03-02 |
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