TWI813539B - 含有特定交聯劑之保護膜形成組成物及使用其之圖型形成方法 - Google Patents
含有特定交聯劑之保護膜形成組成物及使用其之圖型形成方法 Download PDFInfo
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- TWI813539B TWI813539B TW106114125A TW106114125A TWI813539B TW I813539 B TWI813539 B TW I813539B TW 106114125 A TW106114125 A TW 106114125A TW 106114125 A TW106114125 A TW 106114125A TW I813539 B TWI813539 B TW I813539B
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- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- GPHXJBZAVNFMKX-UHFFFAOYSA-M triethyl(phenyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)C1=CC=CC=C1 GPHXJBZAVNFMKX-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
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- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/094—Multilayer resist systems, e.g. planarising layers
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
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Abstract
提供一種對鹼性過氧化氫水溶液形成保護膜之組成物。
提供一種含有1分子中具有2個以上之由縮水甘油基、末端環氧基、環氧基環戊基、環氧基環己基、氧雜環丁基、乙烯基醚基、異氰酸酯基及封閉型異氰酸酯基所成群組中選出的至少1種基的交聯劑、側鏈或末端具有以下述式(1)所表示之基且重量平均分子量為800以上的化合物、及有機溶劑的對鹼性過氧化氫水溶液形成保護膜之組成物。
(式中,X1表示與前述交聯劑反應之取代基,R0表示直接鍵結或碳原子數1或2的伸烷基,X2表示碳原子數1或2的烷基、碳原子數1或2的烷氧基、或氟基,a表示0~2的整數,b表示1~3的整數,c表示0~4的整數,b與c符合1≦(b+c)≦5之關係式。)
Description
本發明係關於在微影術製程中,用以形成對鹼性過氧化氫水溶液耐性優異的保護膜的組成物。進而係關於使用前述保護膜來形成圖型之方法。
已知在基板與於其上形成的阻劑膜間設置阻劑下層膜,形成期望形狀的阻劑圖型之微影術製程。然而,以往阻劑下層膜,例如專利文獻1所記載的由含有胺基塑料系交聯劑的組成物形成的阻劑下層膜,對鹼性過氧化氫水溶液之耐性差。因此,無法將如此之阻劑下層膜用作為使用鹼性過氧化氫水溶液的蝕刻製程中之遮罩。
在下述專利文獻2記載有含有具有被保護的羧基的化合物、具有可與羧基反應的基的化合物、及溶劑的微影術用下層膜形成組成物、或含有具有可與羧基反應
的基與被保護的羧基的化合物、及溶劑的微影術用下層膜形成組成物,該組成物作為必須成分不含胺基塑料系交聯劑。但是在專利文獻2並未記載或暗示由該組成物形成的阻劑下層膜對鹼性過氧化氫水溶液之耐性。
在下述專利文獻3,記載使用對鹼性過氧化氫水溶液具有耐性的阻劑下層膜的圖型形成方法。而用以形成該阻劑下層膜的組成物含有重量平均分子量1000~100,000之具有環氧基的聚合物、及溶劑。
[專利文獻1]專利第4145972號公報
[專利文獻2]國際公開第2005/013601號
[專利文獻3]國際公開第2015/030060號
近年日益要求比以往對鹼性過氧化氫水溶液之耐性更好的保護膜。本發明係以提供用以形成對鹼性過氧化氫水溶液具有耐性的保護膜的新穎的組成物、及使用該保護膜的圖型形成方法為目的。
本發明之發明者發現不包含胺基塑料系交聯
劑的特定交聯劑與含有與該特定交聯劑反應之取代基的重量平均分子量為800以上的化合物的組合,可解決上述課題。即、本發明之第一態樣為含有1分子中具有2個以上之由縮水甘油基、末端環氧基、環氧基環戊基、環氧基環己基、氧雜環丁基、乙烯基醚基、異氰酸酯基及封閉型異氰酸酯基所成群組中選出的至少1種基的交聯劑、側鏈或末端具有以下述式(1)所表示之基且重量平均分子量為800以上的化合物、及有機溶劑的對鹼性過氧化氫水溶液形成保護膜之組成物。
(式中,X1表示與前述交聯劑反應之取代基,R0表示直接鍵結或碳原子數1或2的伸烷基,X2表示碳原子數1或2的烷基、碳原子數1或2的烷氧基、或氟基,a表示0~2的整數,b表示1~3的整數,b表示2或3時,-R0-X1所表示之基可互為相異,c表示0~4的整數,c表示2、3或4時,X2所表示之基可互為相異,b與c符合1≦(b+c)≦5之關係式。)
前述保護膜形成組成物亦可為取代側鏈或末端具有以前述式(1)所表示之基且重量平均分子量為800以上的化合物而含有側鏈或末端具有以下述式(2)所表示
之基且重量平均分子量為800以上的化合物者。
(式中,R1表示直接鍵結或碳原子數1~8之直鏈狀或分支鏈狀的伸烷基,X1表示與前述交聯劑反應之取代基。)
與前述交聯劑反應之取代基X1表示與交聯劑直接反應的基或含有與交聯劑直接反應的基的基。又,與交聯劑直接反應的基可包含具有保護基的基且藉由該保護基離去而與交聯劑反應的基。
與前述交聯劑反應之取代基X1為例如下述式(3)、式(4)、式(5)、式(6)、式(7)、式(8)、式(9)、式(10)或式(11)所表示之基。
(式中,R2表示碳原子數1~8之直鏈狀、分支鏈狀或
環狀的烷基,R3表示氫原子或碳原子數1~8之直鏈狀、分支鏈狀或者環狀的烴基,e表示0或1。)
與前述交聯劑反應之取代基X1較佳為前述式(3)、式(5)或式(6)所表示之基。
前述交聯劑的添加量為例如,以前述重量平均分子量為800以上的化合物中之與前述交聯劑反應之取代基X1總量為100莫耳%時,可使該取代基X120莫耳%~150莫耳%密封的量。又,前述交聯劑較佳為1分子中具有2個以上的縮水甘油基、末端環氧基或環氧基環己基。
前述封閉型異氰酸酯基為例如下述式(11)或式(12)所表示之基。
(式中,R4及R5各自獨立,表示碳原子數1~5的烷基,R6表示碳原子數1~5的烷基,d表示1~3的整數,d表示2或3時,R6所表示之碳原子數1~5的烷基可互為相異。)
本發明之保護膜形成組成物可再含有交聯觸媒。又,本發明之保護膜形成組成物可再含有界面活性劑。
本發明之第二態樣為在表面亦可形成無機膜的半導體基板上,使用本發明之第一態樣的對鹼性過氧化氫水溶液形成保護膜之組成物,形成保護膜,在前述保護膜上形成阻劑圖型,以前述阻劑圖型作為遮罩將前述保護膜乾蝕刻,使前述無機膜或前述半導體基板之表面露出,以乾蝕刻後的前述保護膜作為遮罩,使用鹼性過氧化氫水溶液,將前述無機膜或前述半導體基板進行溼蝕刻及洗淨的圖型形成方法。
前述鹼性過氧化氫水溶液含有例如氨、氫氧化鈉、氫氧化鉀、氰化鈉、氰化鉀、三乙醇胺或尿素。前述鹼性過氧化氫水溶液含有氨時,該鹼性過氧化氫水溶液,例如為25質量%~30質量%的氨水溶液(A)、30質量%~36質量%的過氧化氫水溶液(B)及水(C)之混合物,相對於前述氨水溶液(A)的前述過氧化氫水溶液(B)之體積比:(B)/(A),例如為0.1~20.0、及相對前述氨水溶液(A)的前述水(C)之體積比:(C)/(A),例如為1.0~50.0。
本發明之保護膜形成組成物所形成的保護膜,對鹼性過氧化氫水溶液具有耐性。尤其,由使用1分子中具有2個以上之縮水甘油基、末端環氧基、或環氧基環己基的交聯劑的保護膜形成組成物所形成的保護膜,對鹼性過氧化氫水溶液具有優異的耐性。因此,由本發明之保護膜形成組成物所形成的保護膜,可用作為使用鹼性過
氧化氫水溶液的蝕刻製程及洗淨製程中之遮罩。
本發明之保護膜形成組成物所含有的成分,在以下詳細說明。
本發明之保護膜形成組成物包含側鏈或末端具有以前述式(1)所表示之基或前述式(2)所表示之基,且重量平均分子量為800以上的化合物。前述化合物的重量平均分子量為由膠體滲透層析法(GPC),使用聚苯乙烯作為標準試料所得到的值。前述重量平均分子量的上限值,例如為500,000。前述重量平均分子量為800以上的化合物不限於聚合物,可為由單聚物、二聚物、三聚物及寡聚物所構成群組中選出的1種、或2種以上之混合物。該聚合物可為共聚物(Copolymer)、同聚物(Homopolymer)任一。
前述式(1)所表示之基,可舉例如下述式(1-1)~式(1-111)所表示之基。
前述式(2)所表示之基,可舉例如下述式(2-1)~式(2-28)所表示之基。
前述重量平均分子量為800以上的化合物可再具有在193nm之波長具有吸收的吸光部位或在248nm之波長具有吸收的吸光部位。在193nm之波長具有吸收的吸光部,可舉例如苯環、萘環、三嗪環、異氰脲環,在248nm之波長具有吸收的吸光部,可舉例如萘環、蒽環、三嗪環。
本發明之保護膜形成組成物含有1分子中具有2個以上之縮水甘油基、末端環氧基、環氧基環戊基、環氧基環己基、氧雜環丁基、乙烯基醚基、異氰酸酯基及封閉型異
氰酸酯基所成群組中選出的至少1種基的交聯劑。該交聯劑,可1分子中具有2個以上上述基之中1種,亦可1分子中具有各1個(合計2個)上述基之中之2種。
1分子中具有2個以上之縮水甘油基、末端環氧基、環氧基環戊基及環氧基環己基所成群組中選出的至少1種基的化合物,可舉例如參(2,3-環氧基丙基)異氰脲酸酯、1,4-丁二醇二縮水甘油基醚、甘油三縮水甘油基醚、二乙二醇二縮水甘油基醚、1,2-環己烷二羧酸二縮水甘油基酯、1,2-環氧基-4-(環氧基乙基)環己烷、4,4’-伸甲基雙[N,N-雙(環氧乙基甲基)苯胺]、三羥甲基丙烷三縮水甘油基醚、雙酚-A-二縮水甘油基醚、日產化學工業(股)製的TEPIC〔註冊商標〕-L、TEPIC-SS、TEPIC-PASB26L、TEPIC-PAS B22、TEPIC-VL、TEPIC-UC、(股)Daicel製的EPFD AT501、同CT301、Celloxide〔註冊商標〕2021、同2081、同8000、Epolead〔註冊商標〕GT-401、同PB3600、同PB4700、EHPE3150、EHPE3150CE、三菱化學(股)製的152、154、157S70、168V70、604、630、801N、801PN,802、806、807、811、813、816A,816C,819、825、827、828、828EL、828US、828XA、834X90、871、872、1001、1002、1003、1004、1007、1009、1010、1031S、1032H60、1256、4004P、4005P、4007P、4010P、4250、4275、5046B80、YL980、YL983U、YL6810、YL6121L、YX4000、YX4000H、YX8000、YX8034、YX8800、日本
化藥(股)製的NC-3000、NC-3000-L、NC-3000-H、NC-3000-FH-75M、NC-3100、CER-3000-L、NC-2000-L、XD-1000、NC-7000L、NC-7300L、EPPN-501H、EPPN-501HY、EPPN-502H、EOCN-1020、EOCN-102S、EOCN-103S、EOCN-104S、CER-1020、EPPN201、BREN-S、BREN-105、GAN、GOT、RE-3035-L、RE-310S、Nagase ChemteX(股)製的Denacol〔註冊商標〕EX-211、同EX-212、同EX-252、同EX-810、同EX-811、同EX-850、同EX-851、同EX-821、同EX-830、同EX-832、同EX-841、同EX-861、同EX-911、同EX-941、同EX-920、同EX-931、同EX-313、同EX-314、同EX-321、同EX-411、同EX-421、同EX-512、同EX-612、同EX-614、BASF JAPAN(股)製的CY175、CY177、CY179、CY182、CY184、CY192、DIC(股)製的EPICLON840、同804-S、同850、同850-S、同850-CRP、同850-LC、同860、同1050、同1055、同3050、同4050、同7050、同AM-020-P、同AM-040-P、同HM-091、同HM-101、同830、同830-S、同EXA-830LVP、同835、同EXA-835LV、同1051-75M、同7070-40K、同HM-091-40AX、同152、同153、同153-60T、同153-60M、同1121N-80M、同1123P-75M、同N-660、同N-665、同N-670、同N-673、同N-680、同N-695、同N-655-EXP-S、同N-662-EXP-S、同N-665-EXP、同N-672-EXP、同N-670-EXP-S、同N-685-EXP-S、同N-673-80M、同N-680-75M、同N-690-
75M、同N-740、同N-770、同N-775、同N-865、同HP-4032、同HP-4032D、同HP-4700、同HP-4710、同HP-4770、同HP-5000、同HP-7200、同HP-7200H、同HP-820、同5500、同5800、四國化成(股)製的MA-DGIC、DAG-G、TG-G、新日鐵住金化學(股)製的EpoTohto〔註冊商標〕YD-127、同YD-128、同YDF-170、同YD-8125、同YDF-8170C、同ZX-1059、同YD-825GS、同YD-825GSH、同YDF-870GS、同YDPN-138、同YDCN-700、同YDC-1312、同YSLV-80XY、同YSLV-120TE、同ST-3000、同ST-4000D、同YD-171、同YH-434、同YH-434L、同FX-289BEK75、同FX-305EK70、同ERF-001M30。
此外,1分子中具有2個以上之縮水甘油基、末端環氧基、環氧基環戊基及環氧基環己基所成群組中選出的至少1種基的化合物,亦可使用聚合物。作為前述聚合物,若為1分子中具有2個以上之縮水甘油基、末端環氧基、環氧基環戊基及環氧基環己基所成群組中選出的至少1種基的聚合物,則不特別限制而可使用。如此之聚合物可藉由使用具有環氧基的加成聚合性單體的加成聚合來製造,或可藉由具有羥基的高分子化合物與表氯醇、對甲苯磺酸縮水甘油酯等之具有環氧基的化合物的反應來製造。可舉例如聚縮水甘油基丙烯酸酯、縮水甘油基甲基丙烯酸酯及乙基甲基丙烯酸酯的共聚物、縮水甘油基甲基丙烯酸酯與苯乙烯與2-羥基乙基甲基丙烯酸酯的共聚物等之
加成聚合聚合物、環氧基酚醛清漆等之縮聚合聚合物。該聚合物的重量平均分子量,例如為1000~200,000。
1分子中具有2個以上之氧雜環丁基的化合物,可舉例如7-氧雜雙環[4.1.0]庚烷-3-羧酸(7-氧雜雙環[4.1.0]庚烷)-3-基甲基酯、東亞合成(股)製的ARON OXETANE〔註冊商標〕OXT-121、同OXT-221。
此外,1分子中具有2個以上之氧雜環丁基的化合物,亦可使用聚合物。作為前述聚合物,若為1分子中具有2個以上之氧雜環丁基的聚合物,則不特別限制而可使用。如此之聚合物,可藉由使用具有氧雜環丁基的加成聚合性單體的加成聚合來製造。該聚合物的重量平均分子量,例如為1000~200,000。
1分子中具有2個以上之乙烯基醚基的化合物,可舉例如1,3,5-參(4-乙烯基氧基丁基)偏苯三酸酯、雙(4-乙烯基氧基丁基)間苯二甲酸酯。
此外,1分子中具有2個以上之乙烯基醚基的化合物,亦可使用聚合物。作為前述聚合物,若為1分子中具有2個以上之乙烯基醚基的聚合物,則不特別限制而可使用。如此之聚合物,可藉由使用具有乙烯基醚基的加成聚合性單體的加成聚合來製造。該聚合物的重量平均分子量,例如為1000~200,000。
1分子中具有2個以上之異氰酸酯基的化合物,可舉例如DIC(股)製的BURNOCK〔註冊商標〕D-750、同D-800、同DN-920、同DN-950、同DN-955、同
DN-980、同DN-981、三井化學(股)製TAKENATE〔註冊商標〕500、同600、同D-110N、同D-120N、同D-140N、同D-165N、同D-170N、同D-177N。
此外,1分子中具有2個以上之異氰酸酯基的化合物,亦可使用聚合物。作為前述聚合物,若為1分子中具有2個以上之異氰酸酯基的聚合物,則不特別限制而可使用。如此之聚合物可藉由使用具有異氰酸酯基的加成聚合性單體的加成聚合來製造。該聚合物的重量平均分子量,例如為1000~200,000。
1分子中具有2個以上之封閉型異氰酸酯基的化合物,可舉例如三井化學(股)製TAKENATE〔註冊商標〕B-815N、同B-830、同B-842N、同B-870N、同B-874N、同B-882N、同B-7005、同B-7030、同B-7075、同B-5010、Evonik公司製VESTAGON〔註冊商標〕B1065、同B1400、同B1530、Evonik公司製VESTANAT〔註冊商標〕B1358/100、同B1370、同EP-DS1076、同EP-DS1205。
此外,1分子中具有2個以上之封閉型異氰酸酯基的化合物,亦可使用聚合物。作為前述聚合物,若為1分子中具有2個以上之封閉型異氰酸酯基的聚合物,則不特別限制而可使用。如此之聚合物,可藉由使用具有封閉型異氰酸酯基的加成聚合性單體的加成聚合來製造。該聚合物的重量平均分子量,例如為1000~200,000。
前述交聯劑的添加量為例如,以前述重量平
均分子量為800以上的化合物中之與前述交聯劑反應之取代基X1總量為100莫耳%時,可使該取代基X120莫耳%~150莫耳%、較佳為40莫耳%~140莫耳%、更佳為60莫耳%~120莫耳%密封的量。本發明之保護膜形成組成物中的前述交聯劑的含量過少時及過多時,有變得難以得到形成之保護膜對阻劑溶劑或鹼性過氧化氫水溶液之耐性之情形。
本發明之保護膜形成組成物,作為任意成分,為了促進交聯反應,可含有交聯觸媒。作為該交聯觸媒,除酸性化合物、鹼性化合物外,可使用因熱而產生酸或鹼之化合物。作為酸性化合物,可使用磺酸化合物或羧酸化合物,作為因熱而產生酸之化合物,可使用熱酸產生劑。
磺酸化合物或羧酸化合物,可舉例如p-甲苯磺酸、三氟甲磺酸、吡啶鎓-p-甲苯磺酸酯、水楊酸、樟腦磺酸、5-磺基水楊酸、4-氯苯磺酸、4-羥基苯磺酸、吡啶鎓-4-羥基苯磺酸、苯二磺酸、1-萘磺酸、4-硝基苯磺酸、檸檬酸、安息香酸、羥基安息香酸。
作為熱酸產生劑,例如K-PURE〔註冊商標〕CXC-1612、同CXC-1614、同TAG-2172、同TAG-2179、同TAG-2678、同TAG2689(以上、King Industries公司製)、及SI-45、SI-60、SI-80、SI-100、SI-110、SI-150(以上、三新化學工業(股)製)。
此等交聯觸媒可1種或2種以上組合使用。又,作為鹼性化合物,可使用胺化合物或氫氧化銨化合物,作為因熱而產生鹼的化合物,可使用尿素。
胺化合物,可舉例如三乙醇胺、三丁醇胺、三甲基胺、三乙基胺、三正丙基胺、三異丙基胺、三正丁基胺、三-tert-丁基胺、三正辛基胺、三異丙醇胺、苯基二乙醇胺、硬脂醯基二乙醇胺、及二氮雜雙環辛烷等之第3級胺、吡啶及4-二甲基胺基吡啶等之芳香族胺。又,苄基胺及正丁基胺等之第1級胺、二乙基胺及二正丁基胺等之第2級胺亦可列舉作為胺化合物。此等之胺化合物可單獨或二種以上組合使用。
作為氫氧化銨化合物,例如氫氧化四甲基銨、氫氧化四乙基銨、氫氧化四丙基銨、氫氧化四丁基銨、氫氧化苄基三甲基銨、氫氧化苄基三乙基銨、氫氧化十六基三甲基銨、氫氧化苯基三甲基銨、氫氧化苯基三乙基銨。
又,作為因熱而產生鹼的化合物,可使用例如具有醯胺基、胺基甲酸酯基或氮丙啶基般熱不安定性基,且藉由加熱生成胺的化合物。其他,尿素、苄基三甲基銨氯化物、苄基三乙基銨氯化物、苄基二甲基苯基銨氯化物、苄基十二基二甲基銨氯化物、苄基三丁基銨氯化物、膽鹼氯化物亦可列舉作為因熱而產生鹼的化合物。
前述保護膜形成組成物含有交聯觸媒時,其含量相對該保護膜形成組成物所含有的重量平均分子量為800以上的化合物的含量,例如為0.2質量%~20質量%。
本發明之保護膜形成組成物,作為任意成分,為了使對半導體基板之塗佈性提升,可含有界面活性劑。作為前述界面活性劑,可舉例如聚氧化乙烯月桂基醚、聚氧化乙烯硬脂醯基醚、聚氧化乙烯十六基醚、聚氧化乙烯油烯基醚等之聚氧化乙烯烷基醚類、聚氧化乙烯辛基苯基醚、聚氧化乙烯壬基苯基醚等之聚氧化乙烯烷基芳基醚類、聚氧化乙烯.聚氧化丙烯嵌段共聚物類、山梨糖單月桂酸酯、山梨糖醇酐單棕櫚酸酯、山梨糖醇酐單硬脂酸酯、山梨糖醇酐單油酸酯、山梨糖醇酐三油酸酯、山梨糖醇酐三硬脂酸酯等之山梨糖醇酐脂肪酸酯類、聚氧化乙烯山梨糖單月桂酸酯、聚氧化乙烯山梨糖醇酐單棕櫚酸酯、聚氧化乙烯山梨糖醇酐單硬脂酸酯、聚氧化乙烯山梨糖醇酐三油酸酯、聚氧化乙烯山梨糖醇酐三硬脂酸酯等之聚氧化乙烯山梨糖醇酐脂肪酸酯類等之非離子系界面活性劑、EFTOP〔註冊商標〕EF301、同EF303、同EF352(三菱材料電子化學品(股)製)、MEGAFAC〔註冊商標〕F171、同F173、同R-30、同R-30N、同R-40、同R-40-LM(DIC(股)製)、FluoradFC430、同FC431(住友3M(股)製)、Asahiguard〔註冊商標〕AG710、Surflon〔註冊商標〕S-382、同SC101、同SC102、同SC103、同SC104、同SC105、同SC106(旭硝子(股)製)等之氟系界面活性劑、有機矽氧烷聚合物KP341(信越化學工業(股)製)。此等之界面活性劑可
單獨或二種以上組合使用。前述保護膜形成組成物含有界面活性劑時,其含量相對該保護膜形成組成物所含有的重量平均分子量為800以上的化合物的含量,例如為0.01質量%~10質量%。
本發明之保護膜形成組成物可藉由使上述各成分溶於有機溶劑來調製,且以均勻溶液狀態使用。作為前述有機溶劑,例如乙二醇單甲基醚、乙二醇單乙基醚、甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、二乙二醇單甲基醚、二乙二醇單乙基醚、丙二醇、丙二醇單乙基醚、丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、丙二醇丙基醚乙酸酯、甲苯、二甲苯、甲基乙基酮、甲基異丁基酮、環戊酮、環己酮、環庚酮、4-甲基-2-戊醇、2-羥基異酪酸甲基酯、2-羥基異酪酸乙基酯、乙氧基乙酸乙基酯、乙酸2-羥基乙基酯、3-甲氧基丙酸甲基酯、3-甲氧基丙酸乙基酯、3-乙氧基丙酸乙基酯、3-乙氧基丙酸甲基酯、丙酮酸甲基酯、丙酮酸乙基酯、乙酸乙基酯、乙酸丁基酯、乳酸乙基酯、乳酸丁基酯、2-庚酮、甲氧基環戊烷、苯甲醚、γ-丁內酯、N-甲基吡咯烷酮、N,N-二甲基甲醯胺、及N,N-二甲基乙醯胺。此等之溶劑可單獨或2種以上組合使用。
調製的保護膜形成組成物以使用孔徑為例如0.2μm或0.1μm的過濾器及/或0.01μm的過濾器,進行過濾後使用為佳。
使用本發明之保護膜形成組成物的圖型形成方法,說明如以下。
作為塗佈本發明之保護膜形成組成物的半導體基板,可舉例如矽晶圓、鍺晶圓、及砷化鎵、磷化銦、氮化鎵、氮化銦、氮化鋁等之化合物半導體晶圓。
使用表面形成有無機膜的半導體基板時,該無機膜藉由例如ALD(原子層堆積)法、CVD(化學氣相堆積)法、反應性濺鍍法、離子披覆法、真空蒸鍍法、旋轉塗佈法(Spin-on-glass:SOG)形成。作為前述無機膜,例如聚矽膜、氧化矽膜、氮化矽膜、BPSG(Boro-Phospho Silicate Glass)膜、氮化鈦膜、氮化氧化鈦膜、鎢膜、氮化鎵膜、及砷化鎵膜。
在如此之半導體基板上以旋轉器、塗佈機等之適當的塗佈方法塗佈本發明之保護膜形成組成物。之後,藉由使用加熱板等之加熱手段進行烘烤,形成保護膜。作為烘烤條件,由烘烤溫度100℃~400℃、烘烤時間0.3分鐘~60分鐘中適宜選擇。較佳為烘烤溫度120℃~350℃、烘烤時間0.5分鐘~30分鐘、更佳為烘烤溫度150℃~300℃、烘烤時間0.8分鐘~10分鐘。形成之保護膜的膜厚方面,例如0.001μm~10μm、較佳為0.002μm~1μm、更佳為0.005μm~0.5μm。烘烤時的溫度比上述範圍低時,則交聯變得不足,有難以得到形成之保護膜的對阻劑溶劑或鹼性過氧化氫水溶液之耐性之情形。另一方面,烘烤時的溫度比上述範圍高時,有保護膜因熱而分解之情形。
接著在前述保護膜上形成阻劑圖型。阻劑圖
型的形成,可藉由一般的方法、即,使光阻溶液塗佈在前述保護膜上,並進行預烤、曝光、簡稱PEB之曝光後烘烤(必要時)、顯影、及洗滌來進行。前述阻劑圖型的形成使用的光阻溶液,若為對曝光所使用的光感光者,則不特別限制,可使用正型光阻。可舉例如由具有因酸而分解使鹼溶解速度上昇的基的黏合劑與光產酸劑所構成的化學增幅型光阻、由因酸而分解使光阻的鹼溶解速度上昇之低分子化合物與鹼可溶性黏合劑與光產酸劑所構成的化學增幅型光阻、由具有因酸而分解使鹼溶解速度上昇的基的黏合劑與因酸而分解使光阻的鹼溶解速度上昇之低分子化合物與光產酸劑所構成的化學增幅型光阻、利用曝光部與未曝光部之鹼溶解速度差的DNQ-酚醛清漆型的非化學增幅型光阻。可舉例如住友化學(股)製,商品名:PAR710、東京應化工業(股)製,商品名:TDUR-P3435LP、THMR-iP1800及信越化學工業(股)製,商品名:SEPR430。取代正型光阻亦可使用負型光阻。
前述曝光係透過用以形成指定圖型的遮罩(光罩)進行,可使用例如i線、KrF準分子雷射、ArF準分子雷射、EUV(極端紫外線)或EB(電子線)。前述顯影可使用鹼顯影液,且由顯影溫度5℃~50℃、顯影時間10秒~300秒適宜選擇。前述鹼顯影液方面,可舉例如氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物的水溶液、氫氧化四甲基銨、氫氧化四乙基銨、膽鹼等之氫氧化四級銨的水溶液、乙醇胺、丙基胺、乙烯二胺等之胺水溶液等之鹼性水
溶液。進一步,亦可於此等之顯影液加入界面活性劑等。亦可使用取代鹼顯影液,以乙酸丁基酯等之有機溶劑進行顯影,使光阻的鹼溶解速度未提升部分顯影之方法。
接著以形成的阻劑圖型作為遮罩,將前述保護膜進行乾蝕刻。此時,在使用的半導體基板表面形成前述無機膜時,使該無機膜的表面露出,於使用的半導體基板表面未形成前述無機膜時,使該半導體基板的表面露出。
進一步,藉由以乾蝕刻後的保護膜(於該保護膜上殘存阻劑圖型時,該阻劑圖型亦)作為遮罩,使用鹼性過氧化氫水溶液,進行溼蝕刻,形成期望的圖型。作為溼蝕刻的藥液,可舉例如將顯示鹼性的物質,例如氨、氫氧化鈉、氫氧化鉀、氰化鈉、氰化鉀、三乙醇胺等之有機胺與過氧化氫水混合,使pH成為鹼性的鹼性過氧化氫水。此外,可使pH成為鹼性者,例如使尿素與過氧化氫水混合,經加熱引發尿素之熱分解而產生氨,最後pH成為鹼性者,亦可用作為溼蝕刻的藥液。鹼性過氧化氫水溶液的使用溫度以25℃~90℃為佳、40℃~80℃更佳。溼蝕刻時間以0.5分鐘~30分鐘為佳、1分鐘~20分鐘更佳。
以下為下述合成例所得到的聚合物的重量平
均分子量的測定使用之裝置等。
裝置:東曹(股)製HLC-8220GPC
GPC管柱:Shodex〔註冊商標〕KF-803L、同KF-802、同KF-801
管柱溫度:40℃
流量:0.2mL/分鐘
溶離液:THF
標準試料:聚苯乙烯(東曹(股))
以下將本發明以實施例更具體說明。但,本發明不限於下述實施例之記載。又,作為鹼性過氧化氫水溶液,雖使用以下的表1或表3所示之組成的藥液,但本發明適用的鹼性過氧化氫水溶液不限於該組成。
<合成例1>
丙二醇中,於溶解有p-乙烯基酚單體的固形分濃度10質量%的溶液(LANCASTER公司製)100g加入丙二醇40.60g,在該溶液溶解甲基丙烯酸甲酯(純正化學(股)製)25g後,在反應液中流通氮30分鐘。反應液邊維持70℃,邊添加溶於丙二醇40g的偶氮二異丁腈(純正化學(股)製)1.32g,在氮環境下進行攪拌。使反應物於蒸餾水1公升中再沈澱而得到的沈澱物過濾,進行乾燥,得到具有下述式(1A)所表示之構造單位的聚合物的粉體。進行得到的聚合物的GPC分析,以標準聚苯乙烯換算重量平均分子量約為5000。又,得到的聚合物的構造為p-乙烯基酚
與甲基丙烯酸甲酯以莫耳比計25:75之比例共聚合者。
<合成例2>
將混合有參-(2,3-環氧基丙基)-異氰脲酸酯(日產化學工業(股)製、製品名:TEPIC-SS)10g、3,7-二羥基-2-萘甲酸酯(東京化成工業(股)製)20.50g、乙基三苯基鏻溴化物(ACROSS公司製)0.90g、及丙二醇單甲基醚73.27g的溶液加溫至120℃,並在氮環境下進行24小時反應,得到含有下述式(1B)所表示之化合物的溶液。進行含有得到的化合物的溶液的GPC分析,以標準聚苯乙烯換算重量平均分子量約為1000。
<合成例3>
將混合有參-(2,3-環氧基丙基)-異氰脲酸酯(日產化學工業(股)製、製品名:TEPIC-SS)10g、2,5-二羥基安息香酸(東京化成工業(股)製)15.63g、乙基三苯基鏻溴化物(ACROSS公司製)0.902g、及丙二醇單甲基醚61.90g的溶液加溫至120℃,並在氮環境下進行24小時反應,得到含有下述式(1C)所表示之化合物的溶液。進行含有得到的化合物的溶液的GPC分析,以標準聚苯乙烯換算重量平均分子量約為1000。
<實施例1>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-8000)0.50g中,加入丙二醇單甲基醚11.52g、丙二醇單甲基醚乙酸酯7.68g、及封閉型異氰酸酯樹脂(Evonik JAPAN(股)製,商品名:VESTANAT〔註冊商標〕B1358/100)0.30g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。進行前述聚對羥基苯乙烯之GPC分析,以標準
聚苯乙烯換算重量平均分子量約為11,000。
<實施例2>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-8000)0.50g中,加入丙二醇單甲基醚11.52g、丙二醇單甲基醚乙酸酯7.68g、及1,3,5-參(4-乙烯基氧基丁基)偏苯三酸酯0.30g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例3>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-8000)0.49g中,加入丙二醇單甲基醚11.52g、丙二醇單甲基醚乙酸酯7.68g、丁烷四羧酸四(3,4-環氧基環己基甲基)修飾ε-己內酯((股)Daicel製,商品名:Epolead〔註冊商標〕GT-401)0.29g、及吡啶鎓p-甲苯磺酸酯0.01g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例4>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-8000)0.60g中,加入丙二醇單甲基醚11.52g、丙二醇單甲基醚乙酸酯7.68g、參(4,5-環氧基戊基)異氰脲酸酯(日產化學工業(股)製,商品名:TEPIC〔註冊商標〕-VL)0.18g、及吡啶鎓p-甲苯磺酸酯0.02g,作成溶液。藉
由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例5>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-8000)0.33g中,加入丙二醇單甲基醚11.52g、丙二醇單甲基醚乙酸酯7.68g、及1,3,5-參(4-乙烯基氧基丁基)偏苯三酸酯0.47g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例6>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-8000)0.43g中,加入丙二醇單甲基醚11.52g、丙二醇單甲基醚乙酸酯7.68g、及新日鐵住金化學(股)製EpoTohto〔註冊商標〕YH-434L0.37g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例7>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-8000)0.45g中,加入丙二醇單甲基醚11.52g、丙二醇單甲基醚乙酸酯7.68g、及四國化成(股)製TG-G 0.35g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例8>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-8000)0.40g中,加入丙二醇單甲基醚5.76g、丙二醇單甲基醚乙酸酯13.44g、及新日鐵住金化學(股)製EpoTohto〔註冊商標〕YH-434L 0.40g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例9>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-8000)0.36g中,加入丙二醇單甲基醚5.76g、丙二醇單甲基醚乙酸酯13.44g、及新日鐵住金化學(股)製EpoTohto〔註冊商標〕YH-434L 0.44g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例10>
於含有合成例1所得之聚合物0.64g的丙二醇單甲基醚溶液3.20g中,加入丙二醇單甲基醚3.20g、丙二醇單甲基醚乙酸酯13.44g、及新日鐵住金化學(股)製EpoTohto〔註冊商標〕YH-434L 0.16g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例11>
於含有合成例1所得之聚合物0.62g的丙二醇單甲基醚溶液3.08g中,加入丙二醇單甲基醚3.30g、丙二醇單甲基醚乙酸酯13.44g、及新日鐵住金化學(股)製EpoTohto〔註冊商標〕YH-434L 0.18g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例12>
於含有合成例1所得之聚合物0.64g的丙二醇單甲基醚溶液3.20g中,加入丙二醇單甲基醚3.20g、丙二醇單甲基醚乙酸酯13.44g、及四國化成(股)製TG-G 0.16g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例13>
於含有合成例2所得之化合物0.44g的丙二醇單甲基醚溶液2.22g中,加入丙二醇單甲基醚3.99g、丙二醇單甲基醚乙酸酯13.44g、及新日鐵住金化學(股)製EpoTohto〔註冊商標〕YH-434L 0.36g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例14>
於含有合成例2所得之化合物0.62g的丙二醇單甲基醚溶液3.08g中,加入丙二醇單甲基醚3.30g、丙二醇單甲基醚乙酸酯13.44g、及四國化成(股)製TG-G 0.18g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例15>
於含有合成例2所得之化合物0.50g的丙二醇單甲基醚溶液2.50g中,加入丙二醇單甲基醚3.76g、丙二醇單甲基醚乙酸酯13.44g、及四國化成(股)製TG-G 0.30g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例16>
於含有合成例2所得之化合物0.47g的丙二醇單甲基醚溶液2.35g中,加入丙二醇單甲基醚3.88g、丙二醇單甲基醚乙酸酯13.44g、及四國化成(股)製TG-G 0.33g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例17>
於含有合成例2所得之化合物0.44g的丙二醇單甲基醚溶液2.22g中,加入丙二醇單甲基醚3.98g、丙二醇單
甲基醚乙酸酯13.44g、及四國化成(股)製TG-G 0.36g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<實施例18>
於含有合成例3所得之化合物0.47g的丙二醇單甲基醚溶液2.33g中,加入丙二醇單甲基醚3.90g、丙二醇單甲基醚乙酸酯13.44g、及四國化成(股)製TG-G 0.33g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製保護膜形成組成物。
<比較例1>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-8000)0.60g中,加入丙二醇單甲基醚11.52g、丙二醇單甲基醚乙酸酯7.68g、1,3,4,6-肆(甲氧基甲基)甘脲0.18g、及吡啶鎓p-甲苯磺酸酯0.02g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製膜形成組成物。本比較例的膜形成組成物不含1分子中具有2個以上之由縮水甘油基、末端環氧基、環氧基環戊基、環氧基環己基、氧雜環丁基、乙烯基醚基、異氰酸酯基及封閉型異氰酸酯基所成群組中選出的至少1種基的交聯劑。
<比較例2>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-
8000)0.49g中,加入丙二醇單甲基醚11.52g、丙二醇單甲基醚乙酸酯7.68g、1,3,4,6-肆(甲氧基甲基)甘脲0.29g、及吡啶鎓p-甲苯磺酸酯0.01g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製膜形成組成物。本比較例的膜形成組成物不含1分子中具有2個以上之由縮水甘油基、末端環氧基、環氧基環戊基、環氧基環己基、氧雜環丁基、乙烯基醚基、異氰酸酯基及封閉型異氰酸酯基所成群組中選出的至少1種基的交聯劑。
<比較例3>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-8000)0.60g中,加入丙二醇單甲基醚11.52g、丙二醇單甲基醚乙酸酯7.68g、3,3’,5,5’-肆(甲氧基甲基)-[1,1’-聯苯基]-4,4’-二醇(本州化學工業(股)製,商品名:TMOM-BP)0.18g、及吡啶鎓p-甲苯磺酸酯0.02g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製膜形成組成物。本比較例的膜形成組成物不含1分子中具有2個以上之由縮水甘油基、末端環氧基、環氧基環戊基、環氧基環己基、氧雜環丁基、乙烯基醚基、異氰酸酯基及封閉型異氰酸酯基所成群組中選出的至少1種基的交聯劑。
<比較例4>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-
8000)0.49g中,加入丙二醇單甲基醚11.52g、丙二醇單甲基醚乙酸酯7.68g、3,3’,5,5’-肆(甲氧基甲基)-[1,1’-聯苯基]-4,4’-二醇(本州化學工業(股)製,商品名:TMOM-BP)0.29g、及吡啶鎓p-甲苯磺酸酯0.01g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製膜形成組成物。本比較例的膜形成組成物不含1分子中具有2個以上之由縮水甘油基、末端環氧基、環氧基環戊基、環氧基環己基、氧雜環丁基、乙烯基醚基、異氰酸酯基及封閉型異氰酸酯基所成群組中選出的至少1種基的交聯劑。
<比較例5>
於聚對羥基苯乙烯(日本曹達(股)製,商品名:VP-8000)0.34g中,加入丙二醇單甲基醚11.52g、丙二醇單甲基醚乙酸酯7.68g、1,3,4,6-肆(甲氧基甲基)甘脲0.45g、及吡啶鎓p-甲苯磺酸酯0.01g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製膜形成組成物。本比較例的膜形成組成物不含1分子中具有2個以上之由縮水甘油基、末端環氧基、環氧基環戊基、環氧基環己基、氧雜環丁基、乙烯基醚基、異氰酸酯基及封閉型異氰酸酯基所成群組中選出的至少1種基的交聯劑。
<比較例6>
於含有合成例1所得之聚合物0.57g的丙二醇單甲基
醚溶液2.84g中,加入丙二醇單甲基醚3.49g、丙二醇單甲基醚乙酸酯13.44g、1,3,4,6-肆(甲氧基甲基)甘脲0.22g、及吡啶鎓p-甲苯磺酸酯0.02g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製膜形成組成物。本比較例的膜形成組成物不含1分子中具有2個以上之由縮水甘油基、末端環氧基、環氧基環戊基、環氧基環己基、氧雜環丁基、乙烯基醚基、異氰酸酯基及封閉型異氰酸酯基所成群組中選出的至少1種基的交聯劑。
<比較例7>
於含有合成例2所得之化合物0.56g的丙二醇單甲基醚溶液2.81g中,加入丙二醇單甲基醚3.51g、丙二醇單甲基醚乙酸酯13.44g、1,3,4,6-肆(甲氧基甲基)甘脲0.22g、及吡啶鎓p-甲苯磺酸酯0.02g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製膜形成組成物。本比較例的膜形成組成物不含1分子中具有2個以上之由縮水甘油基、末端環氧基、環氧基環戊基、環氧基環己基、氧雜環丁基、乙烯基醚基、異氰酸酯基及封閉型異氰酸酯基所成群組中選出的至少1種基的交聯劑。
<比較例8>
於含有合成例2所得之化合物0.44g的丙二醇單甲基
醚溶液2.20g中,加入丙二醇單甲基醚4.00g、丙二醇單甲基醚乙酸酯13.44g、1,3,4,6-肆(甲氧基甲基)甘脲0.35g、及吡啶鎓p-甲苯磺酸酯0.01g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製膜形成組成物。本比較例的膜形成組成物不含1分子中具有2個以上之由縮水甘油基、末端環氧基、環氧基環戊基、環氧基環己基、氧雜環丁基、乙烯基醚基、異氰酸酯基及封閉型異氰酸酯基所成群組中選出的至少1種基的交聯劑。
<比較例9>
於含有合成例3所得之化合物0.41g的丙二醇單甲基醚溶液2.03g中,加入丙二醇單甲基醚4.14g、丙二醇單甲基醚乙酸酯13.44g、1,3,4,6-肆(甲氧基甲基)甘脲0.38g、及吡啶鎓p-甲苯磺酸酯0.01g,作成溶液。藉由使該溶液以孔徑0.02μm的聚乙烯製微過濾器進行過濾,調製膜形成組成物。本比較例的膜形成組成物不含1分子中具有2個以上之由縮水甘油基、末端環氧基、環氧基環戊基、環氧基環己基、氧雜環丁基、乙烯基醚基、異氰酸酯基及封閉型異氰酸酯基所成群組中選出的至少1種基的交聯劑。
(於矽基板上形成塗膜)
藉由於矽基板上,使實施例1~實施例7所調製的保
護膜形成組成物及比較例1~比較例5所調製的膜形成組成物以旋轉塗佈進行塗佈,在220℃進行60秒烘烤,以製作100nm膜厚的塗膜。
(於成膜在矽基板上的氮化鈦膜上形成塗膜)
在形成於矽基板表面的50nm厚度的氮化鈦膜上,使實施例8~實施例18所調製的保護膜形成組成物及比較例5~比較例9所調製的膜形成組成物以旋轉塗佈進行塗佈,並在260℃進行60秒烘烤以製作100nm膜厚的塗膜。
(對光阻溶劑之溶出試驗)
將使用實施例1~實施例7所調製的保護膜形成組成物,並在220℃進行60秒烘烤,於矽基板上製作的塗膜、及使用實施例8~實施例18所調製的保護膜形成組成物,並在260℃進行60秒烘烤,於氮化鈦膜上製作的塗膜,浸漬於光阻塗佈時使用的溶劑之OK73 Thinner(東京應化工業(股)製、丙二醇單甲基醚及丙二醇單甲基醚乙酸酯的混合物)1分鐘,確認在浸漬前後的塗膜的膜厚變化在5%以下。結果顯示實施例1~實施例18所調製的塗膜,可於上層層合阻劑。
(對阻劑顯影液之溶出試驗)
將藉由使用實施例1~實施例7所調製的保護膜形成
組成物,在220℃進行60秒烘烤,於矽基板上製作的塗膜、及使用實施例8~實施例18所調製的保護膜形成組成物,在260℃進行60秒烘烤,於氮化鈦膜上製作的塗膜,浸漬於光阻顯影時所使用的顯影液之NMD-3(東京應化工業(股)製)1分鐘,確認在浸漬前後的塗膜的膜厚變化在5%以下。
(在矽基板上的塗膜對鹼性過氧化氫水溶液之耐性試驗)
將使用實施例1~實施例7所調製的保護膜形成組成物及比較例1~比較例5所調製的膜形成組成物所製作的塗膜,於下述表1所示組成的鹼性過氧化氫水溶液,以同表所示之溫度下、規定的時間(4分鐘、8分鐘、12分鐘)浸漬,之後以目視觀察經水洗、乾燥後的塗膜狀態。結果如下述表2所示。表2中的“□”為即使經4分鐘處理後塗膜未見到剝離的狀態,“○”為即使經8分鐘處理後塗膜未見到剝離的狀態,“◎”為即使經12分鐘處理後塗膜未見到剝離的狀態,“×”為經4分鐘處理後在塗膜的一部份或全部,觀察到剝離的狀態。
由上述表2之結果,顯示使用實施例1~實施例7所調製的保護膜形成組成物製作的塗膜,對鹼性過氧化氫水溶液,具有充分的耐性。即可知此等之塗膜可成為對鹼性過氧化氫水溶液的保護膜。尤其,使用實施例3~實施例7所調製的保護膜形成組成物所製作的塗膜,對鹼性過氧化氫水溶液,具有優異的耐性。另一方面,使用比較例1~比較例5所調製的膜形成組成物所製作的塗膜,顯示不具有對鹼性過氧化氫水溶液之耐性,此等之塗膜顯然無法成為對鹼性過氧化氫水溶液之保護膜。
(在氮化鈦膜上之塗膜的對鹼性過氧化氫水溶液之耐性試驗)
將使用實施例8~實施例18所調製的保護膜形成組成物及比較例5~比較例9所調製的膜形成組成物所製作的塗膜,於下述表3所示組成的鹼性過氧化氫水溶液,以同表所示之溫度及規定的時間(1分鐘、1.5分鐘、2分鐘)浸漬,之後以目視觀察經水洗、乾燥後的塗膜的狀態。結果如下述表4所示。表4中的“□”為即使經1分鐘處理後塗膜未見到剝離的狀態,“○”為即使經1.5分鐘處理後塗膜未見到剝離的狀態,“◎”為即使經2分鐘處理後塗膜未見到剝離的狀態,“×”為經1分鐘處理後在塗膜的一部份或全部,觀察到剝離的狀態。
由上述表4之結果,顯示使用實施例8~實施例18所調製的保護膜形成組成物所製作的塗膜,對鹼性過氧化氫水溶液具有充分的耐性。即可知此等之塗膜可成為對鹼性過氧化氫水溶液的保護膜。尤其,使用實施例13及實施例16所調製的保護膜形成組成物所製作的塗膜,對鹼性過氧化氫水溶液,具有優異的耐性。另一方面,使用比較例5~比較例9所調製的膜形成組成物所製作的塗膜,顯示不具有對鹼性過氧化氫水溶液之耐性,此
等之塗膜顯然無法成為對鹼性過氧化氫水溶液之保護膜。
(交聯劑之重量平均分子量為800以上的化合物中的與該交聯劑反應之取代基的密封量)
在使用實施例1~實施例18所調製的保護膜形成組成物所製作的塗膜中,交聯劑密封重量平均分子量為800以上的化合物中的與該交聯劑反應的取代基(以下稱取代基。)之量,化學構造係已知的交聯劑依據下述式(A),化學構造係未知的交聯劑依據下述式(B)計算的結果如下述表5。
式(A):100×(相對重量平均分子量為800以上的化合物的交聯劑的添加量「質量%」)/
[{100/(重量平均分子量為800以上的化合物的1單位構造的分子量)×(重量平均分子量為800以上的化合物的1單位構造的取代基數)}/(交聯劑1分子的交聯點數)×(交聯劑的分子量)]
式(B):100×(相對重量平均分子量為800以上的化合物的交聯劑的添加量「質量%」)/
[{100/(重量平均分子量為800以上的化合物的1單位構造的分子量)×(重量平均分子量為800以上的化合物的1單位構造的取代基數)}×(交聯劑的每1個交聯點的該交聯劑的分子量)]
Claims (8)
- 一種對鹼性過氧化氫水溶液形成保護膜之組成物,其特徵係含有1分子中具有2個以上之縮水甘油基、末端環氧基、或環氧基環己基的交聯劑、側鏈或末端具有鍵結於碳原子之以下述式(1)所表示之基且不含環氧基之重量平均分子量為800以上的化合物、及有機溶劑,
- 如請求項2記載之對鹼性過氧化氫水溶液形成保護膜之組成物,其中,與前述交聯劑反應之取代基X1為前述式(3)、式(5)或式(6)所表示之基。
- 如請求項1或2記載之對鹼性過氧化氫水溶液形成保護膜之組成物,其中,前述交聯劑的添加量為,以前述重量平均分子量為800以上的化合物中之與前述交聯劑反應之取代基X1總量為100莫耳%時,可使該取代基X1 20莫耳%~150莫耳%密封的量。
- 如請求項1或2記載之對鹼性過氧化氫水溶液形成保護膜之組成物,其再含有交聯觸媒。
- 如請求項1或2記載之對鹼性過氧化氫水溶液形成保護膜之組成物,其再含有界面活性劑。
- 一種圖型形成方法,其特徵係在表面亦可形成無機膜的半導體基板上,使用如請求項1~請求項8中任一項記載之對鹼性過氧化氫水溶液形成保護膜之組成物形成保護膜,在前述保護膜上形成阻劑圖型,以前述阻劑圖型作為遮罩將前述保護膜乾蝕刻,使前述無機膜或前述半導體基板之表面露出,以乾蝕刻後的前述保護膜作為遮罩,使用鹼性過氧化氫水溶液,將前述無機膜或前述半導體基板溼蝕刻及洗淨。
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