JP5623529B2 - 光パターン形成性誘電体材料及び調合物並びに使用方法 - Google Patents
光パターン形成性誘電体材料及び調合物並びに使用方法 Download PDFInfo
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- JP5623529B2 JP5623529B2 JP2012526023A JP2012526023A JP5623529B2 JP 5623529 B2 JP5623529 B2 JP 5623529B2 JP 2012526023 A JP2012526023 A JP 2012526023A JP 2012526023 A JP2012526023 A JP 2012526023A JP 5623529 B2 JP5623529 B2 JP 5623529B2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/307—Other macromolecular compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition
- H01L21/02208—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si
- H01L21/02214—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen
- H01L21/02216—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen the compound being a molecule comprising at least one silicon-oxygen bond and the compound having hydrogen or an organic group attached to the silicon or oxygen, e.g. a siloxane
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
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Description
ここで上記3又は4種の単量体のうちの2種が、構造(1)及び(2)であり、R1が、直鎖アルキル、分枝アルキル、シクロアルキル、芳香族、アレーン及びエステル部分からなる群から選択され、R2が、ビニル、置換ビニル、アセチレン、置換アセチレン及びニトリル部分(moiety)からなる群から選択され、R3が、直鎖アルキレン、分枝アルキレン及びシクロアルキレン部分からなる群から選択され、R4が、直鎖アルコキシ、分枝アルコキシ、シクロアルコキシ、アセトキシ、ヒドロキシル、シリルオキシ及びシラノール部分からなる群から選択され、m、n、o、及びpが、繰返し単位のモルパーセント(mol%)を表し、m+n+o+pは、約40mol%以上であり、3種の単量体のみが存在する場合には、o又はpのどちらかがゼロである、シルセスキオキサン重合体を含む、組成物である。
ポリ[(メチルシルセスキオキサン−コ−ビニルシルセスキオキサン−コ−テトラエトキシシラン)]の合成
熱電対温度計、マグネチックスターラ、窒素導入口を備えた冷却器、及び温度制御型加熱マントルを備えた250ミリリットル(ml)の3つ口丸底フラスコに、トリエトキシメチルシラン(42.12グラム、0.24モル)、トリエトキシビニルシラン(6.25g、0.03モル)、テトラエトキシシラン(5.71グラム、0.03モル)、54.7グラムのメチルイソブチルケトン、及び21mlの1.75%シュウ酸水溶液の混合物を仕込んだ。混合物を窒素下、撹拌しながら加熱した。反応混合物は、最初は不均一であったが、10分間の還流の後、均一になり、還流温度は80℃であった。還流を、総計で7時間続けた。混合物を室温まで冷やし、50mlの酢酸エチルで希釈した。この混合物を50mlずつの脱イオン水で6回抽出した(最後の水抽出物はpH試験紙で中性であった)。有機層を蒸発させて、高真空で室温にて24時間、真空排気した後、22.50グラムの固い泡状物が得られた。アセチル酢酸クロムの存在下、アセトン中の13C NMRにより、ビニル炭素対メチル炭素の比は2:8であった。
ポリ[(メチルシルセスキオキサン−コ−ビニルシルセスキオキサン−コ−ビス−シルセスキオキシルエタン−コ−テトラエトキシシラン)]の合成
熱電対温度計、マグネチックスターラ、窒素導入口を備えた冷却器、及び温度制御型加熱マントルを備えた250mlの3つ口丸底フラスコに、トリエトキシメチルシラン(49.92グラム、0.28モル)、トリエトキシビニルシラン(3.81g、0.02モル)、テトラエトキシシラン(8.33グラム、0.04モル)、ビス−トリメトキシシリルエタン(5.41グラム、0.02モル)、67.5グラムのメチルイソブチルケトン、及び25.2mlの1.75%シュウ酸水溶液の混合物を仕込んだ。混合物を窒素下、撹拌しながら加熱した。反応混合物は、最初は不均一であったが、10分間の還流の後、均一になり、還流温度は79.3℃であった。還流を、総計で7時間続けた。混合物を室温まで冷やし、150mlの酢酸エチルで希釈した。この混合物を150mlずつの脱イオン水で2回抽出し、中程度のサイズのガラスフリットを通して濾過して、微量の不溶物を除去した。濾過した溶液をさらに150mlずつの脱イオン水で4回洗った(最後の水抽出物はpH試験紙で中性であった)。有機層を蒸発させて、高真空で室温にて24時間、真空排気した後、27.2グラムの固い泡状物が得られた。単量体(1)、(2)、(3)及び(4)のモル比は14:1:1:2であった。
ポリ[(メチルシルセスキオキサン−コ−ビニルシルセスキオキサン−コ−ビス−シルセスキオキシルエタン−コ−テトラエトキシシラン)]の合成
熱電対温度計、マグネチックスターラ、窒素導入口を備えた冷却器、及び温度制御型加熱マントルを備えた250mlの3つ口丸底フラスコに、トリエトキシメチルシラン(46.36グラム、0.26モル)、トリエトキシビニルシラン(7.61g、0.04モル)、テトラエトキシシラン(8.33グラム、0.04モル)、ビス−トリメトキシシリルエタン(5.41グラム、0.02モル)、67.5グラムのメチルイソブチルケトン、及び25.2mlの1.75%シュウ酸水溶液の混合物を仕込んだ。混合物を窒素下、撹拌しながら加熱した。反応混合物は、最初は不均一であったが、10分間の還流の後、均一になり、還流温度は79.4℃であった。還流を、総計で7時間続けた。混合物を室温まで冷やし、150mlの酢酸エチルで希釈した。この混合物を150mlずつの脱イオン水で6回抽出した(最後の水抽出物はpH試験紙で中性であった)。有機層を蒸発させて、高真空で室温にて24時間、真空排気した後、30.07グラムの固い泡状物が得られた。単量体(1)、(2)、(3)及び(4)のモル比は13:2:2:1であった。
ポリ[(メチルシルセスキオキサン−コ−ビニルシルセスキオキサン−コ−ビス−シルセスキオキシルエタン)]の合成
メチルトリエトキシシラン(53.49グラム、0.3モル)、ビニルトリエトキシシラン(20.76グラム、0.109モル)、ビス(トリエトキシシラン)エタン(7.38グラム、0.026モル)、及びテトラオルトシリケート(11.36グラム、0.055モル)を、3つ口の500ミリリットル丸底フラスコの中で4−メチル−2−ペンタノン(77.78ml)と共に混合した。1.75wt%シュウ酸溶液(25.2グラム)を60℃で上記の溶液に加えると発熱反応が生じた。反応混合物の温度を70℃に下げ、その後、反応混合物を78.8℃で6時間撹拌した。重合体を抽出するために、酢酸エチル(150ml)を反応混合物に室温で加え、溶液を蒸留水で洗った(7−8回)。減圧下で溶媒を蒸発させて、重合体(27グラム)を得た。
ナノインデンテーション測定
硬化した材料のヤング率をナノインデンテーションによって測定した。対照のポリ(メチルシルセスキオキサン−コ−ビス−シルセスキオキシルエタン)及び2種のポリ(メチルシルセスキオキサン−コ−ビニルシルセスキオキサン−コ−ビス−シルセスキオキシルエタン−コ−テトラエトキシシラン)を、シリコンウェハ上にスピン塗布し、次いで、110℃で1分間、塗布後ベークし、248nm光で露光し、110℃で1分間、露光後ベークし、次いで400℃でUV−熱硬化させた。ポリ(メチルシルセスキオキサン−コ−ビス−シルセスキオキシルエタン)の単量体のモル比率は、15:1であり、測定されたヤング率は5.4GPaであった。第1のポリ(メチルシルセスキオキサン−コ−ビニルシルセスキオキサン−コ−ビス−シルセスキオキシルエタン−コ−テトラエトキシシラン)の単量体のモル比率は、13.5:1.5:1であり、測定されたヤング率は9.9GPaであった。第2のポリ(メチルシルセスキオキサン−コ−ビニルシルセスキオキサン−コ−ビス−シルセスキオキシルエタン−コ−テトラエトキシシラン)の単量体のモル比は、13:2:1であり、測定されたヤング率は10.89GPaであった。
光パターン形成
PGMEA中、20wt%溶液のメチルシルセスキオキサン−コ−ビニルシルセスキオキサン−コ−TEOS及び2wt%のトリフェニルスルホニウムノナフレート、及び0.4部の有機塩基で、パターン形成性の低k組成物を調合した。得られた低k調合物を0.2μmフィルタを通して濾過した。低k組成物を8インチのシリコンウェハ上にスピンコーティングし、110℃で60秒間露光前ベークし、ASML(0.63NA、5/8環状)DUVステッパ上で248nmDUV光でパターン状に露光し、110℃で60秒間、露光後ベークした。これに続いて、0.26NのTMAH現像剤を用いて30秒間のパドル現像ステップを行い、0.190μmのライン及びスペースの構造部を解像した。
105、155:光パターン形成性誘電体層
110、160:マスク
120、170:像
125、175A:非露光領域
130、175B:露光領域
135、180:パターン形成された誘電体層
140、185:開口部
145、190:導電体材料層
150、195:ダマシン配線
Claims (17)
- 組成物であって、
下記構造式(1)、(2)、(3)、(4)の3又は4種の単量体を含むシルセスキオキサン重合体であって、
R1が、直鎖アルキル、分枝アルキル、シクロアルキル、芳香族、アレーン及びエステル部分からなる群から選択され、
R2が、ビニル、置換ビニル、アセチレン、置換アセチレン及びニトリル部分からなる群から選択され、
R3が、直鎖アルキレン、分枝アルキレン及びシクロアルキレン部分からなる群から選択され、
R4が、直鎖アルコキシ、分枝アルコキシ、シクロアルコキシ、アセトキシ、ヒドロキシル、シリルオキシ及びシラノール部分からなる群から選択され、
m、n、o、及びpが、繰返し単位のモルパーセント(mol%)を表し、m+n+o+pは、40mol%以上であり、3種の単量体のみが存在する場合には、o又はpのどちらかがゼロである、前記シルセスキオキサン重合体と、
下記構造(5)の添加剤シルセスキオキサン重合体(以下、添加剤という)であって、
sが、10〜1000の整数である、前記添加剤と
を含む、前記組成物。 - 前記シルセスキオキサン重合体が、塩基水性液に可溶である、請求項1に記載の組成物。
- 前記シルセスキオキサン重合体が、1500〜20,000ダルトンの分子量を有する、請求項1に記載の組成物。
- 前記シルセスキオキサン重合体が、本質的に、前記構造式(1)、(2)及び(3)の単量体からなり、
R1がメチル部分であり、かつmが70mol%〜80mol%であり、
R2がビニル部分であり、かつnが3mol%〜13mol%であり、
R3がエチレン部分であり、かつoが0.5mol%〜6mol%である、
請求項1〜3のいずれか一項に記載の組成物。 - 前記シルセスキオキサン重合体が、本質的に、前記構造式(1)、(2)及び(4)の単量体からなり、
R1がメチル部分であり、かつmが70mol%〜80mol%であり、
R2がビニル部分であり、かつnが3mol%〜13mol%であり、
R4がヒドロキシル部分であり、かつpが2mol%〜10mol%である、
請求項1〜3のいずれか一項に記載の組成物。 - 前記シルセスキオキサン重合体が、本質的に、前記構造式(1)、(2)、(3)及び(4)の単量体からなり、
R1がメチル部分であり、かつmが70mol%〜80mol%であり、
R2がビニル部分であり、かつnが3mol%〜13mol%であり、
R3がエチレン部分であり、かつoが0.5mol%〜6mol%であり、
R4がヒドロキシル部分であり、かつpが2mol%〜10mol%である、
請求項1〜3のいずれか一項に記載の組成物。 - 光酸発生剤、キャスティング溶媒をさらに含む、請求項1〜6のいずれか1項に記載の組成物。
- 1つ又は複数の架橋剤、1つ又は複数の有機塩基、又はそれらの組合せをさらに含む、請求項7に記載の組成物。
- 前記光酸発生剤が、トリフェニルスルホニウムノナフレート、コ(トリフルオロ−メチルスルホニルオキシ)−ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボキシイミド(MDT)、N−ヒドロキシ−ナフタルイミド(DDSN)、オニウム塩、芳香族ジアゾニウム塩、スルホニウム塩、ジアリールヨードニウム塩、及びN−ヒドロキシアミド、イミドのスルホン酸エステル、又はそれらの組合せから選択される、請求項7又は8に記載の組成物。
- 前記キャスティング溶媒が、プロピオン酸エトキシエチル(EEP)、EEPとγ−ブチロラクトンとの組合せ、プロピレングリコールモノメチルエーテルアセテート(PGMEA)、プロピレングリコールモノメチルエーテルアルコール、プロピレングリコールモノプロピルアルコール、プロピレングリコールモノプロピルアセテート、乳酸エチル、又はそれらの組合せから選択される、請求項7〜9のいずれか一項に記載の組成物。
- 前記架橋剤が、メチルフェニルテトラメトキシメチルグリコウリル(メチルフェニルPOWDERLINK)、テトラメトキシメチルグリコウリル、メチルプロピルテトラメトキシメチルグリコウリル、及び2,6−ビス(ヒドロキシメチル)−p−クレゾールから選択される、請求項8に記載の組成物。
- 前記有機塩基が、水酸化テトラアルキルアンモニウム、水酸化セチルトリメチルアンモニウム、1,8−ジアミノナフタレン、及びそれらの組合せから選択される、請求項8又は11に記載の組成物。
- 前記組成物が光活性調合物である、請求項7〜12のいずれか一項に記載の組成物。
- (a)基板上に、請求項13に記載の光活性調合物の層を形成するステップと、
(b)前記層をパターン状に紫外線露光して、露光層を生成するステップと、
(c)前記露光層をベークして、ベーク層を生成するステップと、
(d)前記ベーク層を現像して、前記ベーク層の前記紫外線露光されていない部分を除去し、現像層内に第1のトレンチを形成するステップと、
(e)前記現像層を硬化して、前記第1のトレンチを含むパターン形成された硬化層を形成するステップと、
(f)前記パターン形成された硬化層内の前記第1のトレンチを導電性材料で充填するステップと
を含む、方法。 - 前記ステップ(e)と(f)との間に、
前記パターン形成された硬化層上に、請求項13に記載の光活性調合物の追加層を形成するステップであって、前記光活性調合物中の前記シルセスキオキサン重合体が、シルセスキオキサン三元共重合体又はシルセスキオキサン四元共重合体である、前記形成するステップと、
前記追加層をパターン状に紫外線露光して、追加露光層を生成するステップと、
前記追加露光層をベークして、追加ベーク層を生成するステップと、
前記追加ベーク層を現像して、前記追加ベーク層の紫外線露光されていない部分を除去し、追加現像層内に第2のトレンチを形成するステップと、
前記追加現像層を硬化して、前記第2のトレンチを含むパターン形成された追加硬化層を形成するステップであって、前記第1のトレンチが前記第2のトレンチの底部において露出され、前記基板が前記第1のトレンチの底部において露出される、前記追加硬化層を形成するステップと
を含み、
前記ステップ(f)が、前記第1のトレンチと前記第2のトレンチとを前記導電性材料で同時に充填することを含む、請求項14に記載の方法。 - 前記硬化することが、紫外線と、少なくとも400℃の温度までの加熱との両方に同時に曝露することを含む、請求項14又は15に記載の方法。
- 請求項14〜16のいずれか一項に記載の方法によって製造された構造体。
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