TWI683185B - 可光圖案化組成物以及使用該可光圖案化組成物製造電晶體元件的方法 - Google Patents
可光圖案化組成物以及使用該可光圖案化組成物製造電晶體元件的方法 Download PDFInfo
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- TWI683185B TWI683185B TW104134932A TW104134932A TWI683185B TW I683185 B TWI683185 B TW I683185B TW 104134932 A TW104134932 A TW 104134932A TW 104134932 A TW104134932 A TW 104134932A TW I683185 B TWI683185 B TW I683185B
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Abstract
本教示內容關於用於形成負型可光圖案化介電質材料的組成物,其中該組成物-在其他組分當中尤其-包括一有機填充劑與一或多個光活性化合物,且其中該有機填充劑的存在能使此類光活性化合物被有效移除(在固化之後或在顯影步驟期間或之後),該光活性化合物-假使允許殘留在該光圖案化介電質材料中-將導致其介電特性的不利效應。
Description
本發明係有關於可光圖案化組成物以及使用該可光圖案化組成物製造電晶體元件的方法。
以各種有機和無機(譬如,金屬氧化物)半導體為基底的薄膜電晶體(TFTs)已被開發。為確保良好的元件性能,用於毗鄰半導體組件的多層(譬如,閘極介電質層、被動層、與蝕刻-停止層)的可相容材料是同等地關鍵。當該等層的功能需要具有不同特性的材料時,一般期望該等材料可直接光圖案化而不使用光阻劑,以簡化整體製作過程,尤其是,減少光蝕刻步驟的數量。
大部分最先進的可光圖案化材料是以可曝光固化聚合物及/或可曝光聚合化合物合併光敏部分,例如碳-碳雙鍵、環氧化物、酚醛清漆(Novolak)/重氮醌、或曝光製酸基團為基底。經常,該等系統需要一或多個光起始劑、光敏劑、及/或曝光製酸劑,以有效地進行光化學反應。假使該等可光圖案化材料是用作光阻劑,則光起始劑、光敏
劑、或曝光製酸劑的存在通常不是問題,在該情況,此等在成像步驟之後被剝離,不併入最終元件的一部分。然而,作為電晶體元件的閘極介電質(或毗鄰半導體層的其他層),該等系統並不是良好的材料候選者,因為該光起始劑、光敏劑、或曝光製酸劑傾向促使界面電荷捕獲,其可能導致電晶體特性劣化,例如臨界電壓偏移、磁滯、及增加電流洩漏。
據此,在本領域中對於可用於提供實質上不含任何光起始劑、光敏劑、或曝光製酸劑之可光圖案化介電質,但同時可經溶液-加工並有效地固化的可光圖案化組成物係有所需求。
鑑於前述,本教示內容關於用於形成負型可光圖案化介電質材料的組成物,其中該組成物-在其他組分當中尤其-包括一有機填充劑與一或多個光活性化合物,其中該有機填充劑的存在能使此類光活性化合物被有效移除(在固化之後或在顯影步驟期間或之後),該光活性化合物-假使允許殘留在該光圖案化介電質材料中-將導致其介電特性的不利效應。
一般來說,本發明組成物包括一或多個基質-形成化合物、一或多個光活性化合物、一有機填充劑、以及一有機溶劑或溶劑混合物,其中該有機填充劑對基質-形成化合物的重量比例介於約3:1以及約1:4之間,其中該光活性
化合物適用於引起、促進、及/或敏化一光化學反應,其中該基質-形成化合物形成不溶於有機溶劑或溶劑混合物的一經交聯基質,以及其中該有機填充劑在此類光化學反應為惰性且在此類光化學反應之前與之後皆可溶解或混摻於該有機溶劑或溶劑混合物。在各種具體例中,該基質-形成化合物可以約5-30wt%存在於該組成物中,該光活性化合物可以約8-40wt%存在於該組成物中,該有機填充劑可以約5-30wt%存在於該組成物中,以及該有機溶劑或溶劑混合物可以約50-85wt%存在於該組成物中。該光活性化合物可在以介於約200nm與約500nm之間的波長照光後光活化,尤其在曝光至G(435.8nm)、H(404.7nm)或I(365.4nm)線照光後光活化。
在一些具體例中,該有機填充劑在有機溶劑或溶劑混合物中具有約25mg/ml的最小溶解度。該有機溶劑或溶劑混合物可包含酯類溶劑、醇類溶劑、酮類溶劑、或此等的組合。該有機溶劑或溶劑混合物可包含一或多個乳酸乙酯(EL)、3-乙氧基丙酸乙酯(EEP)、丙二醇甲醚乙酸酯(PGMEA)、與甲基n-戊酮(MAK)。該有機填充劑可為具有介於約200g/mol與約2500g/mol之間的分子量、及/或約200℃與約700℃之間的沸點的一化合物。在若干具體例中,該有機填充劑可為雙-甲氧基化或雙-乙氧基化聚(烷二醇)、或此等的氟化衍生物。舉例來說,該有機填充劑可為具有200g/mol、250g/mol、300g/mol、400g/mol、或500g/mol的數量平均分子量(Mn)的聚乙二醇二甲醚。在一些具體例中,
該有機填充劑可為一端具有一環狀環且另一端具有一親脂鏈的一化合物,其中該親脂鏈具有至少8個碳原子。舉例來說,該有機填充劑可選自(±)-α-生育酚、DL-α-生育酚乙酸酯、乙酸視網酯、以及棕櫚酸視網酯。
在一些具體例中,該基質-形成化合物包含以一可曝光交聯基團官能化的寡聚物或聚合物,該可曝光交聯基團為包含下列的官能基:雙鍵、三鍵、雜環型加成-可聚合基團、或能夠原位形成雙鍵或三鍵或雜環型加成-可聚合基的前驅物。舉例來說,該可曝光交聯基團可包括乙烯基部分、烯丙基部分、乙炔基部分、二烯基部分、丙烯酸酯部分、桂皮酸酯部分、香豆素基部分、苯并環丁烷部分、環氧基或環氧乙烷部分、氧雜環丁烷部分、或硫雜環丙烷部分。該可曝光交聯基團可作為懸接基團連結至選自下列的介電質聚合物:聚(乙烯酚)、聚(乙酸乙烯酯)、聚(乙烯醇)、聚(丙烯酸酯)、聚(甲基丙烯酸酯)、聚(甲基丙烯酸甲酯)、聚苯乙烯、聚(乙烯胺)、聚馬來醯亞胺、聚醯亞胺、聚碸、矽氧烷聚合物、酚甲醛(酚醛清漆)樹脂、苯并噁唑聚合物、聚(噁二唑)、馬來酸酐聚合物、以及此等的共聚物。在該等具體例中,該光活性化合物可包括曝光製酸劑、光敏劑或兩者。
在一些具體例中,該基質-形成化合物包含一或多個可曝光聚合化合物單體或寡聚物。舉例來說,該一或多個可曝光聚合單體或寡聚物可選自下列:(i)單官能及/或多官能丙烯酸酯單體與寡聚物、(ii)單官能及/或多官能環氧
基或環硫基單體與寡聚物、(iii)單體型苯乙烯與寡聚型丙烯酸酯、(iv)硫醇-烯單體與寡聚物、(v)丙烯酸酯-及/或環氧基-官能化多面體狀寡聚型矽倍半氧烷、(vi)單官能及/或多官能馬來醯亞胺單體與寡聚物、以及(vii)此等的混合物。在該等具體例中,該光活性化合物可包括光起始劑以及任擇的光敏劑。該組成物更可包括共起始劑。
本教示內容亦提供一種用於形成在一電晶體元件中一光圖案化介電質組件(photopatterned dielectric component)的方法。該方法大致上包括在一基材上沉積一可光圖案化組成物,以提供一薄膜,該可光圖案化組成物包含一或多個基質-形成化合物、一或多個光活性化合物、一有機填充劑、以及一有機溶劑或溶劑混合物;以成像式照光使該薄膜曝光,藉此致使薄膜曝光區域的該一或多個基質-形成化合物形成不溶於有機溶劑或溶劑混合物的一經聚合或經交聯基質;以一顯影劑移除該薄膜的未曝光區域,以提供一光圖案化介電質組件;以及以該有機溶劑或溶劑混合物沖洗該光圖案化介電質組件,俾使在該光圖案化介電質組件中的光活性化合物少於該可光圖案化組成物中的光活性化合物重量百分比(wt%)的約5%。該方法亦可包括照光前的軟烘烤步驟。該軟烘烤步驟可在低溫(譬如,介於約100-150℃之間)進行一段短時間(譬如,介於約30秒與5分鐘之間)。該方法亦可包括照光後的硬烘烤步驟。該硬烘烤步驟可在高溫(譬如,介於約250-350℃之間)進行約10分鐘至1小時。
本教示內容更關於一種具有成像組分的電晶體,其中該成像組分具有少於0.5wt%光活性化合物且製備自包含至少10wt%光活性化合物的負型光阻劑。
本教示內容的上述及其他特徵與優點將由下列圖式、說明、實施例與申請專利範圍更完全地理解。
應理解到的是,下述圖式僅用於例示目的。該圖式不一定按照比例,其重點一般放在例示本教示內容的原理。該圖式並不意圖以任何方式限制本教示內容的範疇。
圖1比對製自下列之薄膜在200mJ曝光固化之前和之後不久、以及在PGMEA後固化的30s或60s沖洗之後的吸收光譜:(a)根據本教示內容的組成物,其包括以丙二醇甲醚乙酸酯配製的環氧基官能化光聚合物、曝光製酸劑、光敏劑、及有機填充劑(PEG,Mn~250),以及(b)不含有機填充物的比較調配物。
圖2比對製自下列之薄膜在600mJ曝光固化之前和之後不久、以及在PGMEA後固化的30s或60s沖洗之後的吸收光譜:(a)根據本教示內容的組成物,其包括以丙二醇甲醚乙酸酯配製的環氧基官能化光聚合物、曝光製酸劑、光敏劑、及有機填充劑(PEG,Mn~250),以及(b)不含有機填充物的比較調配物。
圖3比對製自下列之薄膜所獲得的吸收光譜:(a)根據本教示內容的組成物(明確地說,以添加有機填充劑改質的可市購光阻劑調配物)以及(b)未改質之可市購光阻劑
調配物。
圖4比對具有根據本教示內容已移除光活性化合物(經由後固化沖洗步驟,虛線)之光圖案化介電質組件的代表性電晶體元件的傳輸特性相較於具有殘留光活性化合物之光圖案化介電質組件的比較元件的傳輸特性(無後固化沖洗步驟,實線)。
在通篇申請書中,當組成物被描述成具有、包括、或包含特定的組分時,或當方法被描述成具有、包括、或包含特定的方法步驟時,可設想到的是本教示內容的組成物亦基本上由列舉的組分構成、或由列舉的組分構成,以及本教示內容的方法亦基本上由列舉的方法步驟構成、或由列舉的方法步驟構成。
在本申請書中,當一單元或組分被說明為包括在及/或選自於所列舉之單元或組分的清單時,應理解到的是該單元或組分可為所列舉單元或組分的任一者,或可選自於由二或多個所列舉單元或組分構成的群組。再者,應理解到的是本案所述組成物、裝置、或方法的單元及/或特徵可以各種不同方式組合,而不脫離本案所明示或隱含之本教示內容的精神和範疇。
應理解到的是步驟的順序或執行若干動作的順序為無關緊要,只要本教示內容保持可操作即可。而且,可同時進行二或多個步驟或動作。
使用術語「包括(include)」、「包括(includes)」、「包括(including)」、「具有(have)」、「具有(has)」、或「具有(having)」一般應理解為開放式與非限制性,除非另有明確陳述。
本案使用單數包括複數(反之亦然),除非另有明確陳述。此外,當術語「約(about)」是使用在數量值之前時,本教示內容亦包括特定數量值本身,除非另有明確陳述。如本案所使用,術語「約」係指標稱值的±10%變動,除非另有指示或推論。
本教示內容關於用於形成負型可光圖案化介電質材料的組成物,其中該組成物在其他組分當中尤其包括一有機填充劑與一或多個光活性化合物,且其中該有機填充劑的存在能使此類光活性化合物被有效移除(在固化之後或在顯影步驟期間或之後),該光活性化合物-假使允許殘留在該光圖案化介電質材料中-將導致其介電特性的不利效應。舉例來說,本發明組成物可用於製備電晶體元件中的光圖案化組分。相較於母組成物,此類光圖案化組分可具有高的交聯程度(且因此高的機械強度與熱及/或耐化學性程度)但顯著降低的光活性化合物位準。因此,相較於具有殘留相當份量之光活性化合物的類似光圖案化介電質材料的電晶體元件,根據本教示內容的電晶體元件可具有更好的元件性能與改良的穩定性。
更尤其,本發明組成物大致上包括溶在有機溶劑或溶劑混合物中的一或多個基質-形成化合物、一或多個光活性化合物、以及一有機填充劑。取決於基質-形成化合物
的光化學,光活性化合物可適於引發、促進及/或敏化一光化學反應,其中該光化學反應使得該基質-形成化合物形成不溶於母溶劑或溶劑混合物之一經聚合或經交聯基質。該有機填充劑在該光化學反應中為惰性(即,非反應物),以及在該光化學反應之前與之後,該有機填充劑在有機溶劑或溶劑混合物的溶解度(或混摻性)係實質上相同。有機填充劑對基質-形成化合物的重量比例可介於約3:1至約1:4之間。較佳地,有機填充劑對基質-形成化合物的重量比例可介於約1:1至約1:4之間。更佳地,有機填充劑對基質-形成化合物的重量比例可介於約1:2至約1:4之間。
在一些具體例中,該基質-形成化合物可選自各種可曝光聚合單體與寡聚物,該等單體與寡聚物-在光起始劑(以及任擇地共起始劑及/或光敏劑)存在時-在照光後可聚合成不溶性聚合型基質。在一些具體例中,該基質-形成化合物可選自以一或多個可曝光交聯基團官能化的各種寡聚物或聚合物,該等寡聚物或聚合物-在光敏劑及/或曝光製酸劑存在時-在照光後可曝光交聯成不溶性基質。如前所述,在最終光圖案化材料中不希望存在光起始劑、曝光製酸劑、及/或光敏劑(及其曝光產物)的應用中,本發明組成物的有機填充劑可有助於此等的後固化提取,藉由使此等在曝光固化基質中保持流動而容許在顯影步驟期間將此等移除。據此,最終光圖案化材料可被製成實質上不含(譬如,<1重量%)光起始劑、曝光製酸劑、光敏劑、以及此等的曝光產物。本教示內容亦關於用於製造具有製自本
案所述組成物之組分的電晶體元件的方法,以及具有實質上不含光起始劑、曝光製酸劑、光敏劑、和此等的曝光產物之光圖案化組分的電晶體元件。
有機填充劑
一般來說,該有機填充劑為惰性化合物,該有機填充劑在本發明組成物使用的有機溶劑或溶劑混合物中具有相對高的溶解度或可與本發明組成物使用的有機溶劑或溶劑混合物混摻。舉例來說,在該基質-形成化合物以100mg/mL存在於組成物的具體例中,該有機填充劑可具有25mg/mL的最小溶解度。在用來聚合或交聯該基質-形成化合物的反應條件下,該有機填充劑不與存在於根據本教示內容之組合物的任何給定具體例的基質-形成化合物、光活性化合物、及/或有機溶劑之任一者反應。一般來說,該有機填充劑為化學穩定的化合物,不吸收UV-vis光譜內的光,且不具有容易與存在於基質-形成化合物中的(多個)可曝光聚合基團及/或可曝光交聯基團反應的官能基(譬如胺基團、硫醇基團、(甲基)丙烯酸酯基團等等)。
該有機填充劑可具有介於約200g/mol及約2500g/mol之間的分子量。在某些具體例中,有機填充劑的分子量可不少於組成物中最高分子量光活性化合物的分子量超過50%。舉例來說,假使該組成物僅包括光敏劑作為光活性化合物且光敏劑具有400g/mol的分子量,該有機填充劑可為具有200g/mol或更高的分子量的化合物。較佳地,該有機填充劑的分子量為至少300g/mol,更佳地,至少500
g/mol,以及甚至更佳地,至少750g/mol;但不大於2500g/mol,較佳地,不大於2000g/mol,更佳地,不大於1500g/mol,以及甚至更佳地,不大於1000g/mol。
此外,該有機填充劑通常具有高於150℃的沸點。這是因為在該組成物沉積於基材之後但在照光之前,經常進行一軟烘烤步驟,以減少該膜的溶劑濃度,其有助於避免起泡、使暗蝕減至最少、以及改良薄膜至基材的黏著性。軟烘烤步驟經常在約100℃進行。較佳地,該有機填充劑的沸點係介於約200℃與約700℃之間。
在較佳的具體例中,該有機填充劑在常見光阻劑溶劑中為可混摻或具有至少25mg/mL的溶解度,該光阻溶劑包括酯類溶劑,例如:乳酸乙酯(EL)、3-乙氧基丙酸乙酯(EEP)、丙二醇甲醚乙酸酯(PGMEA);以及酮類溶劑,例如2-庚酮(或甲基n-戊酮,MAK)。如本案所使用,「可混摻(miscible)」意指有機填充劑與有機溶劑或溶劑混合物並不展現相分離。在更佳的具體例中,有機填充劑在包含酯類溶劑的有機溶劑或溶劑混合物中為可混摻或具有至少25mg/mL的溶解度。在更佳的具體例中,有機填充劑在包含丙二醇甲醚乙酸酯的有機溶劑或溶劑混合物中為可混摻或具有至少25mg/mL的溶解度。
該有機填充劑一般可以約5-30wt%存在於組成物中,且具有對基質-形成化合物之介於約3:1與約1:4之間的重量比例。在有機填充劑於室溫為液體的具體例中,該有機填充劑可藉由下列之至少一者與有機溶劑區分:1)基
質-形成化合物在有機填充劑中具有少於50mg/mL的溶解度及/或光活性化合物在有機填充劑中具有少於5mg/mL的溶解度,2)有機溶劑(通常具有介於約140℃-180℃之間的沸點)比起有機填充劑(通常介於約200℃與約700℃之間)具有顯著較低的沸點,以及3)比起有機填充劑,有機溶劑以更高許多的wt%存在於起始組成物中(就有機溶劑而言,約50-85wt%,對比於就有機填充劑而言,約5-30wt%)。再者,有機填充劑適於存在於薄膜內,直到顯影步驟,而有機溶劑在曝光步驟之前係大部分被驅除(譬如經由軟烘烤步驟),僅有少量的有機溶劑適於在曝光固化期間殘留於薄膜內。
在一些具體例中,尤其是在該基質-形成化合物包含(甲基)丙烯酸酯-基底單體、寡聚物、及/或聚合物的具體例中,該有機填充劑可選自甲氧基化或乙氧基化聚(環氧烷)及此等的氟化衍生物。特定的例子包括聚乙二醇二甲醚、以及六丙烯氧化物的寡聚物。在較佳的具體例中,該基質-形成化合物為具有200g/mol、250g/mol、300g/mol、400g/mol、或500g/mol的數量平均分子量(Mn)的聚乙二醇二甲醚。
在一些具體例中,有機填充劑可為一端具有一環狀環且另一端具有一親脂長鏈的一化合物。舉例來說,該親脂鏈可具有至少8個碳原子。例子包括(±)-α-生育酚、DL-α-生育酚乙酸酯、乙酸視網酯、以及棕櫚酸視網酯。
基質-形成化合物
本發明組成物可包括一或多個基質-形成化合物。
在各種具體例中,該基質-形成化合物可以約5-30wt%存在於組成物中。在一些具體例中,該基質-形成化合物可為以可曝光交聯基團官能化的寡聚物或聚合物。舉例來說,該可曝光交聯基團可為包括下列的官能基:雙鍵、三鍵、雜環型加成-可聚合基團、或能夠原位形成雙鍵或三鍵或雜環型加成-可聚合基團的官能基。在某些具體例中,該可曝光交聯基團可包含乙烯基部分、烯丙基部分、乙炔基部分、二烯基部分、丙烯酸酯部分、桂皮酸酯部分、香豆素基部分、苯并環丁烷部分、環氧基或環氧乙烷部分(譬如環氧基環己基乙基、縮水甘油基、縮水甘油醚基、丙基縮水甘油醚基)、氧雜環丁烷部分、或硫雜環丙烷部分。
該等可曝光交聯基團可作為懸接基團連結至各種聚合物骨架。適宜的聚合物骨架包括各種介電質聚合物,其例子包括-但不限於-聚(乙烯酚)、聚(乙酸乙烯酯)、聚(乙烯醇)、聚(丙烯酸酯)、聚(甲基丙烯酸酯)、聚(甲基丙烯酸甲酯)、聚苯乙烯、聚(乙烯胺)、聚馬來醯亞胺,聚醯亞胺、聚碸、矽氧烷聚合物、酚甲醛(酚醛清漆)樹脂、苯并噁唑聚合物、聚(噁二唑)、馬來酸酐聚合物、以及此等的共聚物。
據此,在一些具體例中,該基質-形成化合物可
為乙烯基(共)聚合物(譬如聚(乙烯酚)、聚(乙酸乙烯酯)、聚(乙烯醇)、聚(丙烯酸酯)、聚(甲基丙烯酸酯)、聚(甲基丙烯酸甲酯)、聚苯乙烯、聚(亞乙胺)),該乙烯基(共)聚合物帶有以含有烯類不飽和鍵的部分官能化的懸接基團(譬如乙烯基部分、烯丙基部分、二烯基部分、丙烯酸酯部分、桂皮酸酯部分、香豆素基部分、苯并環丁烷部分)。此等聚合物的一些例子係被載述於美國專利號2,670,287、2,716,102、4,569,901、7,981,989、8,338,555、8,802,783、8,878,169及8,937,301中。在特定一些具體例中,該基質-形成化合物可以是均聚物,或具有選自下面之一重複單元之共聚物:桂皮酸乙烯酯、甲基丙烯酸缩水甘油酯、烯丙基縮水甘油醚、丙烯酸乙酯、醋酸乙烯肉桂酯(vinyl cinnamylide acetate)、甲基丙烯酸硫缩水甘油酯(thioglycidylmethacrylate)、烯丙基硫縮水甘油醚(allylthioglycidylether),以及N-苯甲基丙烯醯胺。
在一些具體例中,該基質-形成化合物可為聚醯亞胺、聚馬來醯亞胺、聚碸、矽氧烷聚合物、酚甲醛(酚醛
清漆)樹脂、苯并噁唑聚合物、聚(噁二唑)、馬來酸酐聚合物、或此等的共聚物,其帶有以含有烯類不飽和鍵的部分官能化的懸接基團(譬如乙烯基部分、烯丙基部分、二烯基部分、丙烯酸酯部分、桂皮酸酯部分、香豆素基部分、苯并環丁烷部分)、環氧基或環氧乙烷部分(譬如環氧環己基乙基、縮水甘油基、縮水甘油醚基、丙基縮水甘油醚基)、氧雜環丁烷部分、或硫雜環丙烷部分。該等聚合物的一些例子係說明於U.S.Pat.Nos.4,180,404與9,035,287;以及U.S.Pat.Pub.No.2015/0021597。
在該基質-形成化合物為以固有光活性基團官能化的介電質聚合物(譬如,例如可照光激發而經歷環加成作用的桂皮酸酯基團)的具體例中,本發明組成物可包括光敏劑作為唯一光活性化合物。然而,取決於光化學,亦可添加諸如曝光製酸劑之光起始劑、自由基起始劑。在該基質-形成化合物為以可曝光聚合基團官能化的介電質聚合物的具體例中,本發明組成物可包括至少一光起始劑(譬如曝光製酸劑)與任擇地光敏劑。參見,譬如Nakamura,Kenichiro;Photopolymers:Photoresist Materials,Processes,and Applications;CRC Press;1st ed.(2014)。
在其他具體例中,該基質-形成化合物可包括一或多個可曝光聚合單體及/或寡聚物。適宜的可曝光聚合單體與寡聚物包括,但不限於,(i)單官能及/或多官能丙烯酸酯單體與寡聚物、(ii)單官能及/或多官能環氧基或環硫基單體與寡聚物、(iii)單體型苯乙烯與寡聚型丙烯酸酯、(iv)硫
醇-烯單體與寡聚物、(v)丙烯酸酯及/或環氧基官能化多面體寡聚矽倍半氧烷、(vi)單官能及/或多官能馬來醯亞胺單體與寡聚物、以及(vii)此等的混合物。
單官能及/或多官能丙烯酸酯單體與寡聚物的例子包括丙烯酸異戊酯、丙烯酸硬脂酯、丙烯酸月桂酯、丙烯酸辛酯、丙烯酸癸酯、苯乙烯基丙烯酸異戊酯(isoamylstyl acrylate)、丙烯酸異硬脂酯、2-乙基己基-二甘醇丙烯酸酯、2-羥丁基丙烯酸酯、2-丙烯醯氧乙基六氫鄰苯二甲酸、丙烯酸丁氧基乙酯、乙氧基二乙二醇丙烯酸酯、甲氧基二乙二醇丙烯酸酯、甲氧基聚乙二醇丙烯酸酯、甲氧基丙二醇丙烯酸酯、苯氧基丙烯酸乙酯、丙烯酸四氫糠酯、丙烯酸異冰片酯、丙烯酸2-羥基乙酯、丙烯酸2-羥基丙酯、2-羥基-3-苯氧基丙基丙烯酸酯、乙烯醚丙烯酸酯、2-丙烯醯氧基乙基琥珀酸、2-丙烯醯氧乙基鄰苯二甲酸、2-丙烯醯氧基乙基-2-羥乙基-鄰苯二甲酸、經內酯改質的撓性丙烯酸酯、以及三級丁基環己基丙烯酸酯、三乙二醇二丙烯酸酯、四乙二醇二丙烯酸酯、聚乙二醇二丙烯酸酯、二丙二醇二丙烯酸酯、三丙二醇二丙烯酸酯、聚丙二醇二丙烯酸酯、1,4-丁二醇二丙烯酸酯、1,6-己二醇二丙烯酸酯、1,9-壬二醇二丙烯酸酯、新戊二醇二丙烯酸酯、二羥甲基-三環癸烷二丙烯酸酯、雙酚A EO(環氧乙烷)加成物二丙烯酸酯、雙酚A PO(環氧乙烷)加成物二丙烯酸酯、羥基新戊酸基新戊二醇二丙烯酸酯、丙氧基化新戊二醇二丙烯酸酯、烷氧基化二羥甲基三環癸烷二丙烯酸酯以及聚四亞甲基二醇二丙烯酸酯、三
羥甲基丙烷三丙烯酸酯、經EO改質的三羥甲基丙烷三丙烯酸酯、三(丙二醇)三丙烯酸酯、經己內酯改質的三羥甲基丙烷三丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、季戊四醇乙氧基四丙烯酸酯、二季戊四醇六丙烯酸酯、雙三羥甲基丙烷四丙烯酸酯、甘油丙氧基三丙烯酸酯、以及經己內醯胺改質的二季戊四醇六丙烯酸酯。
其他適宜的單官能丙烯酸酯包括丙烯酸己內酯、環三羥甲基丙烷縮甲醛丙烯酸酯、乙氧基化壬基酚丙烯酸酯、丙烯酸異癸酯、丙烯酸異辛酯、丙烯酸辛癸酯、烷氧基化酚丙烯酸酯、十三烷基丙烯酸酯以及烷氧基化環己酮二甲醇二丙烯酸酯。
其他適宜的雙官能丙烯酸酯包括烷氧基化環己酮二甲醇二丙烯酸酯、烷氧基化己二醇二丙烯酸酯、二噁烷二醇二丙烯酸酯、二噁烷二醇二丙烯酸酯、環己酮二甲醇二丙烯酸酯、二乙二醇二丙烯酸酯與新戊二醇二丙烯酸酯。
其他適宜的三官能丙烯酸酯包括丙氧基化甘油三丙烯酸酯與丙氧基化三羥甲基丙烷三丙烯酸酯。
其他更高官能的丙烯酸酯包括二-三羥甲基丙烷四丙烯酸酯、二季戊四醇五丙烯酸酯、乙氧基化季戊四醇四丙烯酸酯、甲氧基化二醇丙烯酸酯與丙烯酸酯類。
又,可使用對應於上述丙烯酸酯的甲基丙烯酸酯,例如甲氧基三乙二醇甲基丙烯酸酯、甲基丙烯酸羥乙酯、苯氧基乙基甲基丙烯酸酯、環己基甲基丙烯酸酯、以及四
乙二醇二甲基丙烯酸酯。
單體型苯乙烯和寡聚型丙烯酸酯系統的例子包括,但不限於,N,N-二甲基胺基甲基甲基丙烯酸酯(DMAEMA)、2-羥乙基丙烯酸酯(HEA)、2-乙基己基丙烯酸酯(EHA)、以及苯乙烯;三級丁基丙烯酸酯、三級丁基甲基丙烯酸酯、雙-三級丁基衣康酸酯、三級丁基羥基甲基丙烯酸酯、環己基甲基(甲基)丙烯酸酯、環己基乙基(甲基)丙烯酸酯、苯乙基(甲基)丙烯酸酯、苄基(甲基)丙烯酸酯、異冰片基(甲基)丙烯酸酯以及四氫糠基(甲基)丙烯酸酯、以及羥基苯乙烯與α-甲基羥基苯乙烯。
硫醇-烯反應涉及藉由自由基或離子機制之S-H鍵跨雙鍵或三鍵的加成反應。因此,硫醇-烯單體一般包括
聚硫醇與具有烯類不飽和鍵的第二化合物的混合物。聚硫醇的例子包括二-、三-與四-硫醇,例如己二硫醇、癸二硫醇、1,4-丁二醇雙硫代丙酸酯、1,4-丁二醇雙硫代甘醇酸酯、乙二醇雙硫代甘醇酸酯、4-巰基甲基-3,6-二硫雜-1,8-辛二硫醇;三羥甲基丙烷參(3-巰基丙酸酯);季戊四醇肆(3-巰基乙酸酯);三羥甲基丙烷參(3-巰基乙酸酯);季戊四醇肆(3-巰基丙酸酯);乙氧基化季戊四醇肆(3-巰基丙酸酯)、乙二醇3-巰基丙酸酯、聚丙二醇(3-巰基丙酸酯)、乙氧基化三甲基丙烷三(3-巰基丙酸酯)、乙氧基化乙二醇二巰基乙酸酯、三羥甲基丙烷三巰基乙酸酯、甘醇二(3-巰基丙酸酯)、1,4-雙(3-巰基丁醯氧基)丁烷、季戊四醇肆(3-巰基丁酸酯)、三[2-(3-巰基丙醯氧基)乙基]異氰脲酸酯、1,3,5-參(3-巰基丁醯基乙基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮、與(巰基丙基)甲基矽氧烷-二甲基矽氧烷共聚物。
多面體狀寡聚型倍半矽氧烷為具有(RSiO1.5)n基本組成的籠形結構倍半矽氧烷,其中R基團連接到籠形頂點的矽原子。就本發明可曝光固化組成物而言,適宜的多面體寡聚型倍半矽氧烷可具有以下顯示的T8、T10、或T12結構(n分別=8、10、或12):
其中各個R-獨立地-可為環氧基團、丙烯酸酯基團、或甲
基丙烯酸酯基團。
單官能及/或多官能馬來醯亞胺單體與寡聚物的例子包括N-官能化馬來醯亞胺和雙馬來醯亞胺。例示的N-官能化馬來醯亞胺和雙馬來醯亞胺可以下式表示:
分別地,與
其中R可為芳族、雜芳族、或脂族基團。單官能及/或多官能馬來醯亞胺單體與寡聚物可被曝光聚合(任擇地與其他單體,例如乙烯基單體)成聚醯亞胺,例如該等說明於U.S.專利號4,310,641、4,578,328、與8,415,812,以及國際公開案號WO2014/081894者。
對於該基質-形成化合物包括一或多個可曝光聚合單體及/或寡聚物的上述實施例而言,本發明組成物一般包括至少一個光起始劑作為光活性化合物。取決於實際光化學與反應條件,可能需要共起始劑。舉例來說,假使光聚合反應是在空氣中進行(而非氮氣氛),可能需要作用為除氧劑的共起始劑。此外,光敏劑可用於激發(多個)光起始劑。
光起始劑、曝光製酸劑、與光敏劑
當一化合物在照光後產生一反應性物種時,發生光化學反應。在最簡單的情況,假使該化合物(在此情況為基質-形成化合物)不吸收入射波長,或照光後不形成反應性
中間物,則可添加一第二化合物(在此情況為「光活性化合物」),該第二化合物強烈吸收該入射波長以及經歷光化學轉變成一或多個反應性物種或傳遞能量(或電子)至該基質-形成化合物。該基質-形成化合物隨後與該反應性物種交互作用或該基質-形成化合物進行化學反應並變成經交聯或經聚合,以提供所欲的產物(在此情況為不溶性基質)。在更複雜的系統中,可能需要不同光活性化合物的組合以及該反應混合物亦可包括不同的基質-形成化合物的組合。在特別的具體例中,取決於該(多個)基質-形成化合物,本發明組成物可包括一或多個光起始劑、曝光製酸劑及/或光敏劑。因為術語光起始劑、曝光製酸劑、以及光敏劑為功能標籤,並且一特定化合物可在不同反應條件下對於不同反應混合物執行不同功能,就相同化合物而言,在一個反應中作用為光起始劑,但在不同反應中作為光敏劑是有可能的。
在該基質-形成化合物為可曝光聚合單體或寡聚物的具體例中,需要包含至少一個光起始劑的光起始劑系統,以引發光聚合反應。在照光後,該光起始劑分解成反應性物種,其活化單體及/或寡聚物上的特定官能基團的聚合反應。在某些具體例中,一或多個光敏劑(譬如,相比於該光起始劑,吸收更長許多之波長區域的發色團)係結合光起始劑使用。該光敏劑可藉由透過傳遞能量激發光起始劑來協助縮短固化時間及/或減少所需的照光劑量。
不同光起始劑系統是本領域習知的以及可基於生成的活性物種大致上分成三個群組。明確地說,光起始
劑為可將所吸收的電磁能量(即在可見光、紫外線、遠紫外線、電子束以及X射線的曝光後)轉換成起始反應性物種形式,明確地說,自由基、陽離子或陰離子活性位點的化學能的化合物。通常,光起始劑係藉由具有介於約200奈米與約500奈米之間的波長的入射光活化。在某些具體例中,光起始劑係藉由具有約250奈米與約450奈米之間的波長的光活化。
自由基光起始劑通常用於乙烯基單體與寡聚物的光聚合反應,雖然此等亦可用於帶有烯類不飽和基團之寡聚物或聚合物的曝光交聯作用。一些自由基光起始劑為單組分系統,其中兩個自由基係藉由裂解生成,其餘以雙組分系統作用,其中自由基係經由從予體化合物(共起始劑,其亦可作為自由基聚合反應的氧抑制作用的除氧劑)提取氫原子生成。所得的自由基隨後與其他單體、寡聚物、或聚合物分子反應形成額外的自由基,而同時建立或交聯所得的聚合物。整體結果為連鎖反應,藉其連續的自由基物種與單體及寡聚物反應形成聚合物,該反應在兩個自由基物種反應時中止。聚合物的交聯以相同的反應順序發生,以及當聚合物的反應性部分遇到一些其他鏈端基團時反應中止。安息香醚、苯乙酮、苯甲醯基肟、以及醯基膦氧化物為裂解型(第I型)光起始劑的一些例子。二苯甲酮、呫吨酮(xanthones)、以及醌為提取型(第II型)光起始劑的例子。共起始劑的例子包括三級脂族胺,例如二乙醇胺與三乙胺;芳族胺,例如二烷基苯胺;以及胺丙烯酸酯,例如乙基-4-
二甲基胺基苯甲酸酯。硫醇與矽烷亦可用作共起始劑。
自由基光起始劑的特定例子包括安息香醚,例如安息香甲醚、安息香異丙醚、安息香異丁醚、安息香乙醚等等;二苯乙二酮縮酮,例如二苯乙二酮二甲基縮酮等等;α-二烷氧基-苯乙酮/α-羥基-烷基苯酮/α-胺基-烷基苯酮,例如2,2-二甲氧基-2-苯乙酮[Irgacure 651(IR651),購自巴斯夫(BASF)]、2-羥基-2-甲基-1-苯基丙-1-酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙-1-酮、4-(2-羥基乙氧基)苯基-(2-羥基-2-丙基)酮、2,2-二甲氧基苯乙酮、2,2-二乙氧基苯乙酮、2-苄基-2-二甲基胺基-1-(4-嗎啉基苯基)-丁-1-酮、2,2'-二甲氧基-1,2-二苯基乙-1-酮、4-疊氮基-苯乙酮,4-疊氮基-亞苄基苯乙酮等等;苯甲醯基肟,例如2-(o-苯甲醯基肟)-1-[4-(苯硫基)苯基]-1,2-辛二酮、1-(o-乙醯基肟)-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]乙酮等等;醯基膦氧化物,例如三苯基膦氧化物(TPO,購自巴斯夫)、二(2,4,6-三甲基-苯甲醯基)苯基膦氧化物[Irgacure 819,(IR819),購自巴斯夫];烷基苯酮,例如1-羥基環己基苯酮[Irgacure 184,(IR184),購自巴斯夫]、2-甲基-(4-甲基噻吩基)-2-嗎啉基-1-丙-1-酮[Irgacure 907(IR907),購自巴斯夫]等等;以二苯甲酮為基底的光起始劑,例如二苯甲酮、4,4'-二(二甲基胺基)二苯甲酮、4,4'-二(二乙基胺基)二苯甲酮、3,3'-二甲基-4-甲氧基二苯甲酮、4,4’-二氯二苯甲酮等等;噻吨酮,例如1-氯-4-丙氧基-9H-噻吨-9-酮、2,4’-二乙基噻吨-9-酮、2-氯噻吨-9-酮、異丙基-9H-噻吨-9-酮、10-甲基吩噻嗪、噻吨-9-
酮等等;以及醌,例如2-tert-丁基蒽醌、1-氯蒽醌、2-乙基蒽醌、2-戊基蒽醌等等。額外的自由基起始劑包括香豆素與酮基香豆素衍生物、吡喃鎓(pyrylium)與硫代吡喃鎓鹽、以及一些1,2-二酮。可連同第II型光起始劑用作共起始劑的脂族胺例子包括三級胺,例如N-甲基二乙醇胺、三乙醇胺、2-(二甲基胺基)丙烯酸乙酯等等。
陽離子型光起始劑可用於以電子給予取代基(譬如,甲氧基乙烯、4-甲氧基苯乙烯、苯乙烯)及雜環型單體(環醚、環酯、環醯胺、以及環胺)引發烯烴的陽離子型聚合作用。在陽離子型聚合作用中,陽離子型光起始劑將電荷轉移至一單體,該單體隨後變為反應性。此反應性單體繼續與其他單體以相似方式反應,以經由鏈增長形成聚合物。生成光酸的陽離子型光起始劑(譬如,曝光製酸劑)可用於催化聚合物上酸敏化之有機官能基的去保護作用。舉例來說,離子型與非離子型曝光製酸劑皆可與含有環氧化物、氧雜環丁烷、以及乙烯醚的聚合物使用,以引發光酸催化的開環反應,其隨後可引起交聯反應。陽離子型光起始劑的例子包括鎓鹽與三氯甲基-s-三嗪。
在一些具體例中,陽離子型光起始劑可為路易士酸(Lewis acid)的鎓鹽或布氏酸(Bronsted acid)的鎓鹽。鎓鹽包括碘鎓鹽、鋶鹽、鏻鹽銨鹽、以及重氮鹽。特定的例子可包括二芳基碘鎓鹽,例如二苯基碘鎓四氟硼酸鹽、二苯基碘鎓四氟磷酸鹽、二苯基碘鎓四氟砷酸鹽、二苯基碘鎓三氟甲磺酸鹽、二苯基碘鎓三氟乙酸鹽、二苯基碘鎓-p-甲
苯磺酸鹽、4-甲氧基苯基苯基碘鎓四氟硼酸鹽、4-甲氧基苯基苯基碘鎓六氟膦酸鹽、4-甲氧基苯基苯基碘鎓六氟砷酸鹽、4-甲氧苯基苯基碘鎓三氟甲磺酸鹽、4-甲氧基苯基苯基碘鎓三氟乙酸鹽、4-甲氧基苯基苯基碘鎓-p-甲苯磺酸鹽、雙(4-tert-丁基苯基)碘鎓四氟硼酸鹽、雙(4-tert-丁基苯基)碘鎓六氟砷酸鹽、雙(4-tert-丁基苯基)碘鎓三氟甲磺酸鹽、雙(4-tert-丁基苯基)碘鎓三氟乙酸鹽、雙(4-tert-丁基苯基)碘鎓-p-甲苯磺酸等等;以及三芳基鋶鹽,例如三苯基鋶四氟硼酸鹽、三苯基鋶六氟磷酸鹽、三苯基鋶六氟砷酸鹽、三苯基甲磺酸鹽、三苯基鋶三氟乙酸鹽、三苯基鋶-p-甲苯磺酸鹽、4-甲氧基苯基二苯基鋶四氟硼酸鹽、4-甲氧基苯基二苯基鋶六氟磷酸鹽、4-甲氧基苯基二苯基鋶六氟砷酸鹽、4-甲氧苯基二苯基鋶甲磺酸鹽、4-甲氧基苯基二苯基鋶三氟乙酸鹽、4-甲氧苯基二苯基鋶-p-甲苯磺酸鹽、4-苯基硫代苯基二苯基四氟硼酸鹽、4-苯基硫代苯基二苯基六氟膦酸鹽、4-苯基硫代苯基二苯基六氟砷酸鹽、4-苯基硫代苯基二苯基三氟甲磺酸鹽、4-苯基硫代苯基二苯基三氟乙酸鹽、4-苯基硫代苯基二苯基-p-甲苯磺酸鹽等等。鎓鹽陽離子型光起始劑可用作曝光製酸劑。
三氯甲基-s-三嗪的例子包括參(2,4,6-三氯甲基)-s-三嗪、2-苯基-雙(4,6-三氯甲基)-s-三嗪、2-(3-氯苯基)-雙(4,6-三氯甲基)-s-三嗪、2-(2-氯苯基)-雙(4,6-三氯甲基)-s-三嗪、2-(4-甲氧基苯基)-雙(4,6-三氯甲基)-s-三嗪、2-(3-甲氧基苯基)-雙(4,6-三氯甲基)-s-三嗪、2-(2-甲氧基苯基)-雙
(4,6-三氯甲基)-s-三嗪、2-(4-甲硫基苯基)-雙(4,6-三氯甲基)-s-三嗪、2-(3-甲硫基苯基)雙(4,6-三氯甲基-s-三嗪、2-(2-甲硫基苯基)-雙(4,6-三氯甲基)-s-三嗪、2-(4-甲氧基萘基)-雙(4,6-三氯甲基)-s-三嗪、2-(3-甲氧基萘基)雙(4,6-三氯甲基)-s-三嗪、2-(2-甲氧基萘基)-雙(4,6-三氯甲基)-s-三嗪、2-(3,4,5-三甲氧基-β-苯乙烯基)-雙(4,6-三氯甲基)-s-三嗪、2-(4-甲硫基-β-苯乙烯基)-雙(4,6-三氯甲基)-s-三嗪、2-(3-甲硫基-β-苯乙烯基)-雙(4,6-三氯甲基)-s-三嗪、以及2-(2-甲硫基-β-苯乙烯基)-雙(4,6-三氯甲基)-s-三嗪。
雖然許多陽離子型光起始劑可用於產生光酸,某些非離子型化合物亦可用作曝光製酸劑。離子型與非離子型曝光製酸劑兩者經常用於引致聚合物的曝光交聯作用。非離子型曝光製酸劑的例子包括三氟甲磺酸生成劑九氟丁磺酸生成劑、以及(非氟化)磺酸生成劑,例如重氮磺醯基化合物、磺醯氧基醯亞胺、硝基苄磺酸酯、與醯亞胺磺酸酯,特定的例子包括肟酯,例如2-[2-(4-甲基苯基磺醯基亞胺基)]-2,3-二氫噻吩-3-亞基]-2-(2-甲基苯基)乙腈(商品名“IRGACURE PAG 121”,購自巴斯夫)、[2-(丙基磺醯基亞胺基)-2,3-二氫噻吩-3-亞基]-2-(2-甲基苯基)乙腈(商品名“IRGACURE PAG 103”,購自巴斯夫)、[2-(n-辛磺醯基亞胺基)-2,3-二氫噻吩-3-亞基]-2-(2-甲基苯基)乙腈(商品名“IRGACURE PAG 108”,購自巴斯夫)、α-(n-辛烷磺醯基亞胺基)-4-甲氧基苄基氰化物(商品名“CGI 725”,藉由購自巴斯夫製備)、萘二甲醯亞胺三氟甲磺酸酯、2-[2,2,3,3,4,4,4-
七氟-1-(九氟丁磺醯基亞胺基)-丁基]-芴(商品名“CGI 1906”,藉由自巴斯夫市購製備)、2-[2,2,3,3,4,4,5,5-八氟-1-(九氟丁磺醯基亞胺基)-戊基]芴(商品名“CGI 1907”,藉由購自巴斯夫製備)。
陰離子型光起始劑與曝光製鹼劑可用於引發陰離子型聚合作用或醛、酮、以及某些烯類不飽和單體(譬如,乙烯、1,3-二烯、苯乙烯、甲基(丙烯酸酯)、氰基丙烯酸酯、(甲基)丙烯腈、甲基(丙烯醯胺))的交聯。陰離子型光起始劑亦可用於引發單體或寡聚物的陰離子型開環聚合作用或寡聚物或聚合物的交聯作用,該寡聚物或聚合物係選自於下列:環氧化物、矽氧烷、環酯、環醯胺、以及N-羧基-α-胺基酐。陰離子型光起始劑的例子包括在照光後可產生陰離子電荷親核劑的各種化合物(譬如,CN-、I-、Br-、N3 -、NO2 -、Cl-、F-、SCN-、OH-、與OR-)。特定的例子包括肟酯、胺基甲酸酯、9-芴基胺基甲酸酯、二茂鐵環化合物(ferrocenophanes)、四有機基硼酸銨鹽、以脒為基底的N-苄基化結構、芳族甲醯胺、鈷-胺複合物、胺-醯亞胺、胺酮、磷腈鹼、和染料隱色腈(leuconitriles)。
在一些具體例中,光活性化合物包含光敏劑。在一些具體例中,光活性化合物包含光起始劑與光敏劑。該光敏劑吸收一照光波長且隨後將能量或電子轉移至基質-形成化合物或光起始劑。舉例來說,可將光敏劑加至慣常於193nm吸收的可曝光交聯聚合物,以使該聚合物對400nm光敏化。光敏劑的一些例子包括α-醯氧基酯、醯基氧化膦、
安息香、二苯甲酮、噻吨酮、蒽、苝、稠四苯、乙醯苯酮、吩噻酮、1,2-苯并蒽、吩噻嗪、菲、苯并菲、蔻(coronenes)、苯并芘、螢蒽、紅螢烯、芘、陰丹士林(indanthrenes)、蒽醌、吖啶酮、香豆素和酮基香豆素、以及此等的衍生物。可使用光敏劑的組合。特定的例子包括4,4-雙(二乙基胺基)二苯甲酮、苯并[a]蒽-7,12-二酮、異丙基-9H-噻吨-9-酮、2-氯噻吨-9-酮、與1-氯-4-丙氧基-9H-噻吨-9-酮。
在各種具體例中,光起始劑、曝光製酸劑、及光敏劑在曝光至介於約200nm與約500nm之間的波長時可具光活性。在較佳具體例中,光起始劑、曝光製酸劑、及光敏劑在曝光至光譜的G(435.8nm)、H(404.7nm)、或I(365.4nm)線時可具光活性。
該光活性化合物-整體地-可以約8-40wt%存在於本發明組成物中。個別地,各別光活性化合物對基質-形成化合物的重量比例可至多約30%。本領域習知用於製備可曝光交聯介電質的典型調配物通常具有合計少於10wt%光起始劑、曝光製酸劑、以及光敏劑,因為習知此等的存在(以及該等光產物的存在)對於所得介電質的介電特性造成各種不利效應。相較於本領域習知的可曝光交聯介電質,本發明組成物可包括更大量的光活性化合物(舉例來說,高達40wt%),前提是由於該組成物中存在有機填充劑,所以該等光活性化合物(以及其光產物)在顯影步驟期間可有效地被移除。
溶劑
在照光之前,根據本教示內容的基質-形成化合物一般可溶於常見的有機溶劑,但在經歷聚合作用或交聯作用後可變為顯著不溶於相同溶劑。溶解度的變化可藉由將光固化膜浸於用於鑄膜的母溶劑、測量膜厚度的損失來監控。如本文所使用,當一材料於一溶劑中至少一小時之後,該材料經歷小於5%厚度損失時,該材料被認為不溶於該溶劑。
更明確地說,本案揭示的基質-形成化合物與光活性化合物(在照光與光反應前)可在各種常見有機溶劑中具有滿意的溶解性,藉此使組成物適宜用於液相方法。可用於配製本發明聚合物之有機溶劑的例子包括,但不限於,芳族烴溶劑,諸如苯、環己苯、甲苯、二甲苯、與對稱三甲苯;脂肪烴,例如己烷、環戊烷、環己烷、n-壬烷、n-癸烷、n-十一烷、n-十二烷;醇類溶劑,例如甲醇、乙醇、丙醇、異丙醇、1-丁醇、2-乙氧基甲醇、3-甲氧基丙醇、環戊醇、環己醇、與庚醇;酮類溶劑,例如丙酮、乙醯丙酮、甲基乙酮、甲基異丁酮、2-丁酮、2-戊酮、3-戊酮、2-庚酮、3-庚酮、環戊酮、以及環己酮;酯類溶劑,例如乙酸乙酯、乙酸丙酯、乙酸丁酯、乙酸異丁酯、乙酸戊酯、乙酸環己酯、乙酸庚酯、丙酸乙酯、丙酸丙酯、丙酸丁酯、異丁酸甲酯、丙二醇單甲醚乙酸酯(PGMEA)、乳酸甲酯、乳酸乙酯乳酸和γ-丁內酯;醚類溶劑,例如二異丙醚、二丁醚、乙基丙醚、二乙醚、雙(2-甲氧基乙基)醚、二噁烷、苯甲醚、苯乙醚、以及藜蘆醚;以及醯胺類溶劑,例如N-甲基吡咯
烷酮、二甲基甲醯胺、二甲基乙醯胺。較佳的溶劑為酯類溶劑,尤其是,丙二醇單甲醚乙酸酯。該等溶劑的任一者可單獨或組合使用。
添加劑
除了有機填充劑、(多個)基質-形成化合物、(多個)光活性化合物、以及(多個)有機溶劑之外,本發明組成物亦可任擇地包括一或多個添加劑。如上所述,共起始劑可為該等添加劑之一。在一些具體例中,小分子交聯劑可被包括於本發明的組成物中。在一些具體例中,可包括淬滅劑,以中和過量的曝光製酸劑。在一些具體例中,抗氧化劑(除氧劑)可被包括於本發明的組成物中,以加強其儲存穩定性。適宜的抗氧化劑包括酚、亞磷酸酯、與硫醚。尤其,酚類抗氧化劑的例子包括2-t-丁基-p-甲酚、2,6-二-t-丁基-p-甲酚、2,6-二-t-丁基-4-乙酚、2,2'-亞甲基雙-(4-甲基-6-t-丁酚、2,2'-亞甲基雙-(4-乙基-6-t-丁酚、三乙二醇雙[3-(3-(t-丁基-5-甲基-4-羥基苯基)丙酸酯]、1,6-己二醇雙-[3-(3,5-二-t-丁基-5-甲基-4-羥基苯基)丙酸酯]、季戊四醇肆[3-(3,5-二-t-丁基-5-甲基-4-羥基苯基)丙酸酯]、十八烷基-3-(3,5-二-t-丁基-5-甲基-4-羥基苯基)丙酸酯或1,3,5-三甲基-2,4,6-參(3,5-二-t-丁基-4-羥基苄基)苯;亞磷酸鹽類抗氧化劑的例子包括三苯基亞磷酸鹽或參(2,4-二-t-丁基苯基)亞磷酸鹽;硫醚類抗氧化劑的例子包括雙(4-羥基-3-甲基苯基)硫醚、雙(4-羥基苯基)硫醚、4,4'-硫代雙(6-t-丁基-m-甲酚、4,4'-硫代雙(6-t-丁基-o-甲酚或2,2'-硫代雙(4-t-辛酚)。
其他添加劑可包括一或多個表面活性劑、增塑劑、黏著促進劑、流變改質劑、流平劑、潤濕劑、消泡劑、穩定劑(譬如,自由基穩定劑)等等。
本案說明的組成物可經溶液-加工為具有介於約250nm至約50μm之間的厚度的膜,其中該膜之後可經由光化(譬如,UV)照光交聯成機械上堅固和在周圍環境穩定的材料,該材料適宜用作各種電子、光學與光電子元件的永久層。舉例來說,本發明材料可提供具有介於約100nm至約50μm、250nm至約25μm、250nm至約1μm、與約400nm至約800nm之間的厚度的可光圖案化膜。本發明材料可以微米範圍的解析度光圖案化,且可具有約0.2至約10的對比度(γn)。
根據本教示內容的可光圖案化材料在薄膜電晶體中可(單獨或和至少一個其他介電質材料)用作介電層、作為被動材料(舉例來說,以封裝電晶體中的源極與汲極)、或作為蝕刻-停止材料(舉例來說,以在金屬層上方界定源極和汲極的成像(蝕刻)步驟期間,保護底層金屬氧化物半導體層)。
當用作介電質材料時,本發明材料可展現廣大範圍的所欲特性與特點,包括,但不限於,低漏電流密度、高擊穿電壓、低磁滯性、大電容值、均勻的膜厚度、溶液-加工能力、在低溫及/或大氣壓力的製造能力、熱穩定性、空氣與濕度穩定性、抵抗苛性試劑、及/或與多樣化的閘極材料及/或半導體的相容性。當用作被動或界面材料時,本
材料可展現所欲的特性與特點,包括,但不限於,高分解溫度、高光學透明度、低收縮率、低吸濕性、低透氧率、均勻的膜厚度、溶液-加工能力、在低溫及/或大氣壓力的製造能力、與相鄰材料的良好黏著性。當用作蝕刻-停止材料時,本發明材料可展現廣大範圍的所欲特性與特點,包括,但不限於,對常見濕式蝕刻劑的耐化性、光圖案化能力(無需光阻劑,從而減少製作步驟)、高分解溫度、高光學透明度、低收縮率、低吸濕性、低透氧率、均勻的膜厚度、溶液-加工能力、在低溫及/或大氣壓力的製造能力、與相鄰材料(金屬氧化物、金屬或金屬合金、以及有機材料)的良好黏著性。
如本案所使用,「可溶液-加工(solution-processable)」或「經溶液-加工(solution-processed)」意指一組成物經由各種液相方法加工的能力。可溶液-加工的組成物可經由本領域習知的各種液相沉積方法沉積在一基材上,例如導電材料(譬如,電晶體中的源極、汲極、或閘極)或半導體材料(譬如,電晶體中的帶電荷層)。在各種具體例中,液相方法可選自旋轉塗佈、槽式塗佈、印刷(譬如,噴墨印刷、絲網印刷、凹版移印、膠版印刷、凹版印刷、柔性版印刷、平版印刷、大量印刷等等)、噴塗、電噴塗、滴鑄、浸塗、與刮刀塗覆。旋轉塗佈涉及施加過量的塗覆液至基材上,隨後藉由離心力高速旋轉基材,以使流體擴散。製自此技術的所得膜厚度可取決於旋塗速率、溶液的濃度、以及使用的溶劑。舉例來說,印刷可以凹版印
刷機、柔性版印刷機、凹版移印、絲網印刷或噴墨印表機進行。藉由該等印刷方法加工的所得膜厚度可取決於溶液濃度、溶劑選擇、與重複印刷次數。諸如溫度、壓力、與濕度之周圍環境條件亦可影響所得膜厚度。取決於使用的特定印刷技術,印刷品質可受到不同參數影響,包括,但不限於,調配物/組成物的流變特性,例如張力能量與黏度。
根據本教示內容的膜可直接地光圖案化(無使用光阻劑)。據此,一成像層可藉由沉積根據本教示內容的組成物形成,以提供未交聯的膜,使該未交聯的膜以成像圖案光化照光,俾使在曝光區域之可光圖案化組成物中的組分變成交聯;並移除未曝光區域(其仍未交聯且可溶)。更明確地說,該方法可包括沉積本案說明的組成物,以形成具所欲厚度的膜,使該膜經由光罩(具有所欲成像圖案的一光罩)曝光(譬如,以光譜的G(435.8nm)、H(404.7nm)、或I(365.4nm)線),以提供不溶(譬如經交聯)區域以及可溶(譬如未交聯)區域,以及剝離該可溶區域。根據本教示內容的膜為負型,並可藉由有機或水性顯影劑顯影。接續著形成經交聯基質-在顯影步驟期間或之後-該經交聯的膜可以有機溶劑沖洗(尤其是,酯類溶劑,例如PGMEA),以提取有機填充劑與光活性化合物。有機填充劑與光活性化合物的移除可藉由膜厚度損失證實。光活性化合物的移除更可藉由吸收光譜證實。在沖洗步驟之後,該光活性化合物可以少於0.1wt%存在於該膜(相對於在可光圖案化組成物中
的光活性化合物的重量百分比,其為5-30wt%)。
據此,本教示內容亦關於具有成像組分的電晶體,其中該成像組分具有少於0.1wt%光活性化合物且製備自包含至少5wt%光活性化合物之負型光阻劑。該電晶體可為場效應電晶體(FET),尤其是,有機場效應電晶體或金屬氧化物場效應電晶體,其包括薄膜有機物(小分子或聚合型)或金屬氧化物半導體。典型的薄膜電晶體(TFT)包括多個層並且可以各種方式構形。舉例來說,TFT通常包括基材、閘極介電質、半導體、連接至該半導體的源極與汲極、以及鄰近閘極介電質的閘極。當施加電位至閘極上時,電荷載子聚集於半導體的介電質界面。結果為,在源級與汲極之間形成導電通道,假使施加電位至汲極時,電流將流動。
本案說明的電晶體可以陣列排列,其可用作主動矩陣液晶顯示器(AMLCDs)的開關元件或周圍驅動器以及用作主動矩陣有機發光二極管(AMOLEDs)的像素驅動器。
提供下列實施例是為了進一步例示並有助於理解本教示內容,並不意圖以任何方式限制本發明。
實施例1
曝光交聯膜係製備自根據本教示內容的調配物,該調配物包括以丙二醇甲醚乙酸酯(PGMEA))配製的環氧基-官能化光聚合物(聚(甲基丙烯酸縮水甘油酯),PGMA,Mn~20,000,得自Aldrich)、非離子型曝光製酸劑(N-羥基萘二甲醯亞胺三氟甲磺酸鹽,NIT)、光敏劑(雙香豆素化合物,CDIAC)、以及有機填充劑(聚乙二醇二甲醚,PEG,Mn
~250)。比較調配物係以不含有機填充劑製備。
將具有介於約400nm與約600nm之間厚度的膜旋塗於玻璃基板上,隨後使用高壓汞燈經由G&H線濾波器於200mJ或600mJ曝光固化。該經曝光固化的膜先以PGMEA浸泡30s,隨後再浸泡30s(合計60s)。
圖1顯示製自(a)調配物1與(b)比較調配物A之膜樣本在200mJ曝光固化之前和之後不久、以及在PGMEA後固化的30s或60s沖洗之後的吸收光譜。圖2顯示製自(a)調配物1與(b)比較調配物A之膜樣本在600mJ曝光固化之前和之後不久、以及在PGMEA後固化的30s或60s沖洗之後的吸收光譜。
圖1與2皆顯示,在固化之前和之後不久,對應於曝光製酸劑與光敏劑的吸收峰值可在大約340nm與大約440nm觀察到。在圖1(a)與2(a)中,該等兩個峰值在以PGMEA沖洗之後消失,確認在調配物中加入有機填充劑能夠有效地從曝光固化膜中移除曝光製酸劑與光敏劑。相較之下,圖1(b)與2(b)顯示當調配物中並不包括有機填充劑時,
儘管PGMEA的沖洗份量相同,曝光製酸劑與光敏劑仍存在於曝光固化膜中。
本教示內容的一致性係於下列實驗中確認,其中有機填充劑係加至市購光阻劑中。明確地說,將100wt.%(150mg/mL)PEG加至商用SU-8 2000.5光阻劑調配物(Microchem,Newton,MA)。將具有約400nm與約600nm之間厚度的膜旋塗於玻璃基材上,隨後使用UV泛曝光系統10s,於90℃烘烤5min,隨後以PGMEA沖洗30s,隨後再沖洗30s(合計60s)。
圖3顯示此等的吸收光譜。可從圖3(a)看到,就製自PEG-改質調配物的曝光交聯膜而言,有可能藉由以PGMEA沖洗該膜移除光活性化合物的殘餘物。明確地說,由於三芳基鋶鹽的吸收(250-350nm)在沖洗後顯著減少。相較之下,以及如圖3(b)顯示,就製自未改質調配物的曝光交聯膜而言,沖洗後並無觀察到在250-350nm的吸收有變化。
實施例2
製造了具有製自根據本教示內容的調配物(調配物2)之光圖案化介電質的電晶體元件。
更明確地說,調配物2是由以丙二醇甲醚乙酸酯(PGMEA)調配的環氧基環己基乙基多面體狀寡聚型倍半矽氧烷(ECPOSS,Hybrid Plastic EP0408,籠型含量50%)、非離子型曝光製酸劑(N-羥基萘二甲醯亞胺三氟甲磺酸,NIT)、光敏劑(雙香豆素化合物,CDIAC)、與有機填充劑((±)-α-生育酚,VE)來製備。
上閘極下接點的有機薄膜電晶體係於以聚合型平坦層預處理的玻璃基材上(EagleTM 2000,得自康寧公司(Corning Inc.,Corning,NY))製造。Ag電極係經由陰影遮罩沉積至50nm厚度,隨後以表面改質劑層處理。主動式半導體層係藉由將苝二醯亞胺小分子OSC旋塗於Ag接點上方,接著在110℃烘烤步驟5min來形成。該閘極介電質係藉由以800rpm旋塗調配物2達90s來製備。預烘烤係於90℃執行30s,以蒸乾溶劑,藉此提供厚度約400-600nm的膜。曝光交聯作用係藉由GH線曝光(200mJ/cm2),接著在120℃後烘烤步驟10分鐘來實現。後烘烤沖洗步驟係以PGMEA對若干元件進行30s。最終,藉由Ag的熱沉積形成閘極。
圖4比較受測元件的傳輸特性。明確地說,實線顯示以無沖洗步驟完成的代表性元件的傳輸特性。如圖所示,觀察到該等元件的逆時針磁滯現象。相較之下,在進行後烘烤沖洗步驟的元件中,因為光活性化合物CDIAC與NIT藉助有機填充劑VE(虛線)被有效地移除,所以並無觀察到磁滯現象且該元件顯示更好的操作穩定性,相較於以無沖洗步驟完成的元件(其中殘留光活性化合物)。
本說明書所引用的全部出版品-包括但不限於專利與專利申請案一係以參考方式併入本案,如同個別出版品像是完整載列一樣被明確地且獨立地指示以參考方式併入本案。
本教示內容涵蓋其他特定形式的具體例,並不逸離本發明的精神或基本特徵。前述具體例因此在所有方面被認為是例示性而非限制本案所述的本教示內容。本發明的範疇於是由隨附專利申請範圍指示,而非由前述說明指示,落於專利申請範圍等效性之意義與範圍以內的所有改變係意圖涵括在其中。
Claims (30)
- 一種用於形成在一電晶體元件中一光圖案化介電質組件的方法,該方法包含:在一基材上沉積一可光圖案化組成物,以提供一薄膜,該可光圖案化組成物包含一或多個基質-形成化合物、一或多個光活性化合物、一有機填充劑、以及一有機溶劑或溶劑混合物;以成像式照光使該薄膜曝光於一成像圖案,藉此致使在該薄膜之曝光區域的該一或多個基質-形成化合物形成不溶於該有機溶劑或溶劑混合物的一經聚合或經交聯基質,而使在該薄膜之未曝光區域的該一或多個基質-形成化合物保持未交聯;以一顯影劑移除該薄膜的未曝光區域,以提供一光圖案化介電質組件;以及以該有機溶劑或溶劑混合物沖洗該光圖案化介電質組件,以移除該光活性化合物,其中在該沖洗步驟之後,殘留在該光圖案化介電質組件中的光活性化合物總重量係少於該可光圖案化組成物中的光活性化合物總重量的約5%;其中該有機填充劑在該有機溶劑或溶劑混合物中的最小溶解度係約25mg/mL。
- 如請求項1的方法,其中該光活性化合物適於引發、促進、及/或敏化一光化學反應,其中該基質-形成化合物 形成該經聚合或經交聯基質,而且其中該有機填充劑在此類光化學反應中為惰性且在此類光化學反應之前與之後皆可溶解或混摻於該有機溶劑或溶劑混合物。
- 如請求項1的方法,其中該有機溶劑或溶劑混合物包含酯類溶劑、醇類溶劑、酮類溶劑、或此等的組合。
- 如請求項3的方法,其中該有機溶劑或溶劑混合物包含一或多個乳酸乙酯(EL)、3-乙氧基丙酸乙酯(EEP)、丙二醇甲醚乙酸酯(PGMEA)、與甲基n-戊酮(MAK)。
- 如請求項1的方法,其中該有機填充劑具有介於約200g/mol與約2500g/mol之間的分子量。
- 如請求項1的方法,其中該有機填充劑具有介於約200℃與約700℃之間的沸點。
- 如請求項1的方法,其中該有機填充劑選自於由下列所構成的群組:雙-甲氧基化聚(烷二醇)、雙-乙氧基化聚(烷二醇)以及此等的氟化衍生物。
- 如請求項1的方法,其中該有機填充劑為聚乙二醇二甲醚,其具有200g/mol、250g/mol、300g/mol、400g/mol、或500g/mol的數量平均分子量(Mn)。
- 如請求項1的方法,其中該有機填充劑為一端具有一環狀環且另一端具有一親脂鏈的一化合物,其中該親脂鏈具有至少8個碳原子。
- 如請求項1的方法,其中在該可光圖案化組成物中,該基質-形成化合物係以約5-30wt%存在,該光活性化合物係以約8-40wt%存在,該有機填充劑係以約5-30wt%存 在,以及該有機溶劑或溶劑混合物係以約50-85wt%存在,且其中該有機填充劑對該基質-形成化合物的重量比例介於約3:1與約1:4之間。
- 如請求項1的方法,其中該基質-形成化合物包含以一可曝光交聯基團官能化的寡聚物或聚合物,該可曝光交聯基團為包含下列的一官能基:雙鍵、三鍵、雜環型加成-可聚合基團、或能夠原位形成雙鍵或三鍵或雜環型加成-可聚合基的前驅物。
- 如請求項11的方法,其中該可曝光交聯基團包含乙烯基部分、烯丙基部分、乙炔基部分、二烯基部分、丙烯酸酯部分、桂皮酸酯部分、香豆素基部分、苯并環丁烷部分、環氧基或環氧乙烷部分、氧雜環丁烷部分、或硫雜環丙烷部分。
- 如請求項11的方法,其中該基質-形成化合物包含選自於由下列所構成群組的介電質聚合物:聚(乙烯酚)、聚(乙酸乙烯酯)、聚(乙烯醇)、聚(丙烯酸酯)、聚(甲基丙烯酸酯)、聚(甲基丙烯酸甲酯)、聚苯乙烯、聚(乙烯胺)、聚馬來醯亞胺、聚醯亞胺、聚碸、矽氧烷聚合物、酚甲醛(酚醛清漆)樹脂、苯并噁唑聚合物、聚(噁二唑)、馬來酸酐聚合物、以及此等的共聚物,且其中該可曝光交聯基團是作為懸接基團連結。
- 如請求項11的方法,其中該光活性化合物包含一曝光製酸劑、一光敏劑、或兩者。
- 如請求項1的方法,其中該基質-形成化合物包含一或多 個可曝光聚合單體或寡聚物。
- 如請求項15的組成物,其中該一或多個可曝光聚合單體或寡聚物選自於由下列所構成的群組:(i)單官能及/或多官能丙烯酸酯單體與寡聚物、(ii)單官能及/或多官能環氧基或環硫基單體與寡聚物、(iii)單體型苯乙烯與寡聚型丙烯酸酯、(iv)硫醇-烯單體與寡聚物、(v)丙烯酸酯-及/或環氧基-官能化多面體狀寡聚型矽倍半氧烷、(vi)單官能及/或多官能馬來醯亞胺單體與寡聚物、以及(vii)此等的混合物。
- 如請求項15的方法,其中該光活性化合物包含一光起始劑與選擇性地一光敏劑。
- 如請求項17的方法,其中該組成物更包含一共起始劑。
- 如請求項1至18中任一項的方法,其中該光活性化合物在以介於約200nm與約500nm之間的波長照光後光活化。
- 如請求項19的方法,其中該光活性化合物在曝光至G(435.8nm)、H(404.7nm)或I(365.4nm)線照光後被光活化。
- 如請求項1的方法,該方法包含在該曝光步驟之前以介於約100℃與約150℃之間的溫度且於一段介於約30秒與5分鐘之間的時間內軟烘烤該薄膜,其中在此類軟烘烤步驟之後,該薄膜保有相對於該可光圖案化組成物之超過90重量%的有機填充劑但少於20重量%的有機溶劑或溶劑混合物。
- 如請求項1的方法,其中在沖洗步驟後,殘留在該光圖案化介電質組件中的光活性化合物總重量係少於該可光圖案化組成物中的光活性化合物總重量的約2%。
- 如請求項1的方法,其中在沖洗步驟後,殘留在該光圖案化介電質組件中的光活性化合物總重量係少於該可光圖案化組成物中的光活性化合物總重量的約1%。
- 一種薄膜電晶體元件,該薄膜電晶體元件係由請求項1至17及20至23中任一項之方法所製得,且包含一經圖案化介電質組件,其中該經圖案化介電質組件包含少於0.5wt%光活性化合物,且其中該經圖案化介電質組件係製備自包含至少10wt%光活性化合物的一可光圖案化組成物。
- 一種用於形成一負型可光圖案化介電質材料的組成物,該組成物包含:以約5-30wt%存在之一或多個基質-形成化合物;以約8-40wt%存在之一或多個光活性化合物;以約5-30wt%存在之一有機填充劑;以及以約50-85wt%存在之一有機溶劑或溶劑混合物;其中該有機填充劑對該基質-形成化合物的重量比例介於約3:1與約1:4之間;其中該光活性化合物適於引起、促進、及/或敏化一光化學反應,其中該基質-形成化合物形成不溶於該有機溶劑或溶劑混合物的一經交聯基質;而且其中該有機填充劑在此類光化學反應中為惰性且在此類光化學 反應之前與之後皆可溶解或混摻於該有機溶劑或溶劑混合物。
- 如請求項25的組成物,其中該有機填充劑具有(i)介於約200g/mol與約2500g/mol之間的分子量以及(ii)介於約200℃與約700℃之間的沸點。
- 如請求項25的組成物,其中該有機填充劑選自於由下列所構成的群組:雙-甲氧基化聚(烷二醇)、雙-乙氧基化聚(烷二醇)以及此等的氟化衍生物。
- 如請求項25的組成物,其中該有機填充劑為聚乙二醇二甲醚,其具有200g/mol、250g/mol、300g/mol、400g/mol、或500g/mol的數量平均分子量(Mn)。
- 如請求項25的組成物,其中該有機填充劑為一端具有一環狀環且另一端具有一親脂鏈的一化合物,其中該親脂鏈具有至少8個碳原子。
- 如請求項25的組成物,其中該光活性化合物係以約10-40wt%存在。
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