JPWO2016158406A1 - 薄膜トランジスタ用感光性樹脂組成物、硬化膜、薄膜トランジスタ、液晶表示装置または有機電界発光表示装置、硬化膜の製造方法、薄膜トランジスタの製造方法および液晶表示装置または有機電界発光表示装置の製造方法 - Google Patents
薄膜トランジスタ用感光性樹脂組成物、硬化膜、薄膜トランジスタ、液晶表示装置または有機電界発光表示装置、硬化膜の製造方法、薄膜トランジスタの製造方法および液晶表示装置または有機電界発光表示装置の製造方法 Download PDFInfo
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- JPWO2016158406A1 JPWO2016158406A1 JP2016516110A JP2016516110A JPWO2016158406A1 JP WO2016158406 A1 JPWO2016158406 A1 JP WO2016158406A1 JP 2016516110 A JP2016516110 A JP 2016516110A JP 2016516110 A JP2016516110 A JP 2016516110A JP WO2016158406 A1 JPWO2016158406 A1 JP WO2016158406A1
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- Prior art keywords
- thin film
- photosensitive resin
- film transistor
- organic solvent
- resin composition
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- 238000005401 electroluminescence Methods 0.000 title description 5
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
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- 125000001931 aliphatic group Chemical group 0.000 description 4
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Images
Classifications
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
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- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
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- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/133345—Insulating layers
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- 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
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- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
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Abstract
Description
(1)溶解度パラメーターが8.0以上11.0以下[単位は(cal/cm3)1/2]
(2)炭素原子、水素原子、おおよび酸素原子で構成される有機化合物
まず、前記有機溶剤の第一要件である、(1)溶解度パラメーターが8.0以上11.0以下の有機溶剤について説明する。ここでいう溶解度パラメーターは、複数の物質の相溶性および親和性の指標として用いられるものであり、下記(式1)に表される式で定義される。
ただし、ΔEV[106N・m・mol−1]は蒸発熱、V0[m3・mol―1]は1molあたりの体積である。溶解度パラメーターの値は、低極性のものほど小さく、高極性のものほど大きくなり、例えばn−ヘキサン(7.3)、エタノール(12.7)、水(23.4)である。二つの物質の溶解度パラメーターの差は、その二つの物質が相溶するために必要なエネルギーと密接な関係が有り、溶解度パラメーターの差が小さいほど二つの物質が相溶するために必要なエネルギーは小さなものとなる。すなわち、二つの物質が存在した場合、一般に、溶解度パラメーターの差が小さいほど、親和性が高く、相溶性が高いものとなる。
(3)大気圧における沸点が100℃以上180℃以下
大気圧における沸点が100℃以上の有機溶剤を選択することで、溶剤揮発性が高すぎることに起因する塗布不良を防ぐことができ、180℃以下の有機溶剤を選定することで、硬化後の絶縁層に残存する有機溶剤をさらに低減することができる。
のではない。なお、実施例中の薄膜トランジスタ用感光性樹脂組成物、硬化膜、および薄膜トランジスタの評価は以下の方法により行った。
(1)硬化膜からのアウトガス分析
各参考例に即したワニスを8インチシリコンウェハー上にスピンコート法により塗布し、120℃のホットプレート上で2分間プリベークした。2.38%TMAH水溶液で60秒現像し、純水でリンスした。その後、窒素雰囲気下380℃のオーブン中で60分間キュアして膜厚1.0μmの硬化膜を得た。
本実施例で用いた薄膜トランジスタを図3に示し、以下順に製造方法を説明する。厚さ0.7mmのガラス基板11上に、マグネトロンDCスパッタ法にて厚さ100nmとなるようにアルミニウム膜を成膜した。次に、ポジ型レジスト溶液を塗布した後、90℃のホットプレートで乾燥してレジスト膜を形成した。次に、露光、現像してレジスト膜をパターニングした後、リン硝酸エッチング液を用いてレジストパターンのない領域のみアルミニウムを選択的に除去した。次に、レジスト膜を剥離液(モノエタノールアミン/ジメチルスルホキシド=7/3)を用いて除去した後、純水で洗浄し、100℃のホットプレートで30分間乾燥した。このようにして、ゲート電極12を形成した。次に、各参考例に即した薄膜トランジスタ用感光性樹脂組成物をスピンコート塗布し、100℃のホットプレートで乾燥し、厚さ1000nmのプリベーク膜を作製した。得られたプリベーク膜を2.38%TMAH水溶液で現像し、次いで水でリンスした。次いで窒素雰囲気下380℃のオーブン中で60分間キュアした。このようにして厚さ500nmの硬化膜を得て、それをゲート絶縁層13とした。
東京エレクトロン(株)製塗布・現像装置“CLEAN TRACK ACT−12”を用いて、各参考例に即したろ過直後の薄膜トランジスタ用感光性樹脂組成物を12インチSiウエハ上に塗布し、100℃で3分間、ホットプレートで乾燥させ、膜厚1000nmの感光性樹脂膜を得た。得られた感光性樹脂膜について、(株)トプコン製ウエハ表面検査装置“WM−10”にて0.27μm以上の大きさの異物数を計測した。計測面積はウエハの中心から半径8cmの円の内側の約201cm2とし、塗膜1cm2あたりの異物数を求めた。
ろ過後−40℃で90日間保管した薄膜トランジスタ用感光性樹脂組成物を用いて、前記(3)に記載の方法で感光性樹脂膜を作製し、異物評価を実施した。
2,2−ビス(3−アミノ−4−ヒドロキシフェニル)ヘキサフルオロプロパン(以降BAHFと呼ぶ)18.3g(0.05モル)をアセトン100mL、プロピレンオキシド17.4g(0.3モル)に溶解させ、−15℃に冷却した。ここに3−ニトロベンゾイルクロリド20.4g(0.11モル)をアセトン100mLに溶解させた溶液を滴下した。滴下終了後、−15℃で4時間反応させ、その後室温に戻した。析出した白色固体をろ別し、50℃で真空乾燥した。
乾燥窒素気流下、BAHF29.3g(0.08モル)、1,3−ビス(3−アミノプロピル)テトラメチルジシロキサン1.24g(0.005モル)、末端封止剤として、3−アミノフェノール3.27g(0.03モル)をN−メチル−2−ピロリドン(NMP)150gに溶解した。ここに3,3’,4,4’−ジフェニルエーテルテトラカルボン酸二無水物(以降ODPAと呼ぶ)31.0g(0.1モル)をNMP50gとともに加えて、20℃で1時間撹拌し、次いで50℃で4時間撹拌した。その後、キシレンを15g添加し、水をキシレンとともに共沸しながら、150℃で5時間撹拌した。撹拌終了後、溶液を水3Lに投入して白色沈殿を集めた。この沈殿をろ過で集めて、水で3回洗浄した後、80℃の真空乾燥機で24時間乾燥し、目的のポリイミドであるアルカリ可溶性樹脂(A−1)を得た。
乾燥窒素気流下、ODPA31.0g(0.10モル)をNMP500gに溶解させた。ここに合成例1で得られたヒドロキシル基含有ジアミン化合物45.35g(0.075モル)と1,3−ビス(3−アミノプロピル)テトラメチルジシロキサン1.24g(0.005モル)をNMP50gとともに加えて、20℃で1時間反応させ、次いで50℃で2時間反応させた。次に末端封止剤として4−アミノフェノール4.36g(0.04モル)をNMP5gとともに加え、50℃で2時間反応させた。その後、N,N−ジメチルホルムアミドジメチルアセタール28.6g(0.24モル)をNMP50gで希釈した溶液を10分かけて滴下した。滴下後、50℃で3時間撹拌した。撹拌終了後、溶液を室温まで冷却した後、溶液を水3Lに投入して白色沈殿を得た。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で24時間乾燥し、目的のポリイミド前駆体であるアルカリ可溶性樹脂(A−2)を得た。
乾燥窒素気流下、BAHF18.3g(0.05モル)をNMP50g、グリシジルメチルエーテル26.4g(0.3モル)に溶解させ、溶液の温度を−15℃まで冷却した。ここにジフェニルエーテルジカルボン酸ジクロリド(日本農薬(株)製)7.4g(0.025モル)、イソフタル酸クロリド(東京化成(株)製)5.1g(0.025モル)をγ−ブチロラクトン(GBL)25gに溶解させた溶液を内部の温度が0℃を越えないように滴下した。滴下終了後、−15℃で6時間撹拌を続けた。反応終了後、メタノールを10質量%含んだ水3Lに溶液を投入して白色の沈殿を集めた。この沈殿を濾過で集めて、水で3回洗浄した後、80℃の真空乾燥機で24時間乾燥し、目的のポリベンゾオキサゾール前駆体であるアルカリ可溶性樹脂(A−3)を得た。
乾燥窒素気流下、TrisP−PA(商品名、本州化学工業(株)製)21.22g(0.05モル)と5−ナフトキノンジアジドスルホニル酸クロリド36.27g(0.135モル)を1,4−ジオキサン450gに溶解させ、室温にした。ここに、1,4−ジオキサン50gと混合したトリエチルアミン15.18gを、系内が35℃以上にならないように滴下した。滴下後30℃で2時間撹拌した。トリエチルアミン塩を濾過し、ろ液を水に投入した。その後、析出した沈殿をろ過で集めた。この沈殿を真空乾燥機で乾燥させ、下記式で表されるキノンジアジド化合物(B−1)を得た。
乾燥窒素気流下、TrisP−PA(商品名、本州化学工業(株)製)21.22g(0.05モル)と4−ナフトキノンジアジドスルホニル酸クロリド36.27g(0.135モル)を1,4−ジオキサン450gに溶解させ、室温にした。ここに、1,4−ジオキサン50gと混合したトリエチルアミン15.18gを、系内が35℃以上にならないように滴下した。滴下後30℃で2時間撹拌した。トリエチルアミン塩を濾過し、ろ液を水に投入した。その後、析出した沈殿をろ過で集めた。この沈殿を真空乾燥機で乾燥させ、下記式で表されるキノンジアジド化合物(B−2)を得た。
前記合成例2で得られたアルカリ可溶性樹脂(A−1)10.0g、(B−1)1.0gを有機溶剤としてプロピレングリコールモノメチルエーテル(以下PGMEと呼ぶ)40.0gに溶解した後、0.2μmのポリテトラフルオロエチレン製のフィルター(住友電気工業(株)製)で濾過して薄膜トランジスタ用感光性樹脂組成物(ワニス)Aを得た。
製造例1と同様の方法で、化合物の種類と量は表1記載の通りでワニスB〜Sを得た。なお、製造例で用いた有機溶剤に関して、分子構造中の窒素原子および酸素原子の有無、溶解度パラメーター、大気圧における沸点について表2に示す。
製造例1〜19のワニスを用い、上述の(1)硬化膜からのアウトガス分析で記載の方法に従って硬化膜の作製ならびにアウトガス分析を実施し、また、上述の(2)薄膜トランジスタの特性評価で記載の方法に従って薄膜トランジスタを作製し、その特性評価を実施した。結果を表3に示す。
2:バッファー層
3:ソース領域
4:ドレイン領域
5:半導体層
6:ゲート絶縁層
7:ゲート電極
8:層間絶縁層
9:ソース電極
10:ドレイン電極
11:基板
12:ゲート電極
13:ゲート絶縁層
14:半導体層
15:不純物添加半導体層
16:ソース電極
17:ドレイン電極
18:層間絶縁層
Claims (19)
- (A)アミド基および/またはイミド基を有するアルカリ可溶性樹脂、(B)感光性化合物、ならびに(C)有機溶剤を含有する薄膜トランジスタ用感光性樹脂組成物であり、前記(C)有機溶剤中、窒素原子を有する有機溶剤の含有量が有機溶剤全量に対して1質量%以下である、薄膜トランジスタ用感光性樹脂組成物。
- 前記(C)有機溶剤中、下記(1)および(2)を満足する有機溶剤の含有量が有機溶剤全量に対して80質量%以上である、請求項1に記載の薄膜トランジスタ用感光性樹脂組成物。
(1)溶解度パラメーターが8.0以上11.0以下[単位は(cal/cm3)1/2]
(2)炭素原子、水素原子、および酸素原子で構成される有機化合物 - 前記(C)有機溶剤中、窒素原子を有する有機溶剤の含有量が有機溶剤全量に対して0.01質量%以上1質量%以下である、請求項1または2に記載の薄膜トランジスタ用感光性樹脂組成物。
- 前記(C)有機溶剤中、窒素原子を有する有機溶剤の含有量が有機溶剤全量に対して0.01質量%以上0.5質量%以下である、請求項1または2に記載の薄膜トランジスタ用感光性樹脂組成物。
- 前記(1)および(2)を満足する(C)有機溶剤が、さらに下記(3)を満足する、請求項2〜4のいずれかに記載の薄膜トランジスタ用感光性樹脂組成物。
(3)大気圧における沸点が100℃以上180℃以下 - 前記(A)アミド基および/またはイミド基を有するアルカリ可溶性樹脂が、ポリイミド、ポリイミド前駆体、およびポリベンゾオキサゾール前駆体の中から選ばれる少なくとも1種のアルカリ可溶性樹脂またはそれらの共重合体である、請求項1〜5のいずれかに記載の薄膜トランジスタ用感光性樹脂組成物。
- 前記(B)感光性化合物が、キノンジアジド化合物である、請求項1〜6のいずれかに記載の薄膜トランジスタ用感光性樹脂組成物。
- 前記キノンジアジド化合物が、4−ナフトキノンジアジドスルホニルエステル化合物を含む、請求項7に記載の薄膜トランジスタ用感光性樹脂組成物。
- 前記(B)感光性化合物の含有量が、前記(A)アミド基および/またはイミド基を有するアルカリ可溶性樹脂が、ポリイミド、ポリイミド前駆体、およびポリベンゾオキサゾール前駆体の中から選ばれる少なくとも1種のアルカリ可溶性樹脂100質量部に対して0.1質量部以上20質量部以下である、請求項1〜8のいずれかに記載の薄膜トランジスタ用感光性樹脂組成物。
- さらに(D)密着改良剤を含有する、請求項1〜9のいずれかに記載の薄膜トランジスタ用感光性樹脂組成物。
- 前記(D)密着改良剤が、窒素原子を有するシランカップリング剤を含有する、請求項10に記載の薄膜トランジスタ用感光性樹脂組成物。
- 請求項1〜11のいずれかに記載の薄膜トランジスタ用感光性樹脂組成物を硬化した硬化膜。
- 請求項12に記載の硬化膜を、ゲート絶縁層および層間絶縁層の少なくとも一方に有する、薄膜トランジスタ。
- 請求項12に記載の硬化膜を層間絶縁層に有し、窒化ケイ素、酸化ケイ素、酸窒化ケイ素の少なくともいずれかをゲート絶縁層に有する、トップゲート型である薄膜トランジスタ。
- 請求項13または14に記載の薄膜トランジスタを備える、液晶表示装置または有機電界発光表示装置。
- 請求項1〜11のいずれかに記載の薄膜トランジスタ用感光性樹脂組成物を基板に塗布し感光性樹脂膜を形成する工程、前記感光性樹脂膜を乾燥する工程、前記感光性樹脂膜を露光する工程、露光された感光性樹脂膜を現像する工程、および加熱硬化する工程を含む、硬化膜の製造方法。
- 前記加熱硬化する工程が、300℃以上450℃以下で行われる、請求項16に記載の硬化膜の製造方法。
- 請求項16または17に記載の製造方法により得られる硬化膜を用いる、薄膜トランジスタの製造方法。
- 請求項18に記載の製造方法により得られる薄膜トランジスタを用いる、液晶表示装置または有機電界発光表示装置の製造方法。
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