CN116283945A - 酰亚胺磺酸酯类光产酸剂、抗蚀剂组合物及其应用、电子组件 - Google Patents
酰亚胺磺酸酯类光产酸剂、抗蚀剂组合物及其应用、电子组件 Download PDFInfo
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- CN116283945A CN116283945A CN202310197773.2A CN202310197773A CN116283945A CN 116283945 A CN116283945 A CN 116283945A CN 202310197773 A CN202310197773 A CN 202310197773A CN 116283945 A CN116283945 A CN 116283945A
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
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- 239000003504 photosensitizing agent Substances 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- 238000004321 preservation Methods 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
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- IIVUJUOJERNGQX-UHFFFAOYSA-N pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1 IIVUJUOJERNGQX-UHFFFAOYSA-N 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
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- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
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- 229920001567 vinyl ester resin Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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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
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
本发明提供了一种酰亚胺磺酸酯光酸、抗蚀剂组合物及应用。该非离子光酸具有以下通式(1)、(2)所示结构结构。由于4H‑茚并噻吩和R3、R4基团的引入,相对于现有的磺酸酯光酸如NIT等,本申请提供的光酸吸光系数增加,吸收波长红移,在300‑450nm具有更高的感光度和灵敏性、更好的热稳定性和化学稳定性,且应用过程中与其它组分还具有较好的相容性。
Description
技术领域
本发明属于感光材料技术领域,具体涉及一种在300-450nm波长范围内高产酸的酰亚胺磺酸酯类光产酸剂、含有该光产酸剂的抗蚀剂组合物及其应用。
背景技术
光产酸剂是化学增幅型光致抗蚀剂的关键组成之一,其结构和性能对光刻图像有较大影响。非离子i线光产酸剂主要是磺酸酯类。其中,酰亚胺磺酸酯光产酸剂在半导体领域中用作光引发剂已被广泛知悉,如公开号为JP6059953B2、JP6205285B2、JP5715892B2、CN107810179A、CN107250114A等专利文献公开了不同的应用于半导体领域的酰亚胺磺酸酯类产品。这些技术中很少能将光敏感区涵盖i-g线,或在i-g线的产酸率较低。随着对高精细化图案的要求,对于光产酸剂,须具有溶解性高、产酸率高、热稳定性匹配和化学稳定性好等条件。
发明内容
本发明的目的在于提供一种感光度高,溶解性、热稳定性和化学稳定性更具优势的酰亚胺磺酸酯类光产酸剂,含有该光产酸剂的抗蚀剂组合物及其应用。
为了实现上述目的,根据本发明的一个方面,提供一种酰亚胺磺酸酯类光产酸剂,具有如下通式(1)、(2)所示结构:
其中,
R1表示C1-C20的直链状或支链状的烷基、C3-C20的环烷基、C1-C20的直链状或支链状的氟代烷基、C3-C20的氟代环烷基、C6-C18的取代或未取代的芳基、樟脑基、樟脑醌基或叠氮萘酮基团;
R2与R2’可相同,也可不同,各自独立地选自下列基团:氢,卤素,C1-C20的直链状或支链状的烷基,C3-C20的环烷基,C2-C20的直链状或支链状的链烯基,C2-C20的直链状或支链状的炔基,C1-C20的直链状或支链状的烷氧基,C1-C20的直链状或支链状的烷硫基,C1-C20的直链状或支链状的卤代烷基,C1-C20的直链状或支链状的羟基取代烷基,C2-C20的直链状或支链状的羟基烷氧基取代烷基,被C6-C10的芳基或芳氧基取代的C1-C20烷基,被1个以上的-O-、-S-、-O-CO-或-CO-O-中断的C2-C20的直链状或支链状的烷基或烷氧基,取代或未取代的C6-C10芳基,C6-C20的芳基硫基,含有N、O和/或S的C2-C20的杂环基团;或者R2、R2’彼此相连以形成环;
R3和R4选自下列基团:氢,氰基,羟基,卤素,C1-C20的直链状或支链状的烷基,链上的氢原子可以被卤原子或羟基,C2-C20的直链状或支链状的烯基、C2-C20的直链状或支链状的炔基、C1-C20的直链状或支链状的烷基,或C1-C20的直链状或支链状的烷基中的-CH2-被-O-、-S-、-CO-、-COO-或-OCO-取代;C3-C30的环烷基,其中的氢原子可以被卤素、C1-C20的直链或支链烷基、被1个以上的-O-、-S-、-OCO-或-COO-中断的C2-C20的直链状或支链状的烷基所取代;桥环烷基,所述桥环烷基中的氢原子可以被卤素、C1-C20的直链或支链烷基、被1个以上的-O-、-S-、-OCO-或-COO-中断的C2-C20的直链状或支链状的烷基所取代;C6-C30芳基,C6-C30芳基的苯基中至少一个氢原子被C1-C20的直链状或支链状的烷基、C1-C20的直链状或支链状的烷氧基、C6-C20的芳基取代的C1-C20烷氧基、C1-C20的直链状或支链状的烷硫基、C1-C20的酰基、C1-C20的酰氧基或C1-C20的氧酰基取代形成的取代基;含有N、O和/或S的C2-C20的杂环基团,其中的氢原子可以被卤原子或羟基、C2-C20的直链状或支链状的烯基、C2-C20的直链状或支链状的炔基、C1-C20的直链状或支链状的烷基取代,其中,C1-C20的直链状或支链状的烷基中的-CH2-被-O-、-S-、-CO-、/>-COO-或-OCO-取代;R3和R4可以连接成环。
作为优选实施方案,在上述通式(1)、(2)所示结构中,R1表示C1-C10的直链状或支链状的烷基、C3-C10的环烷基、C1-C8的直链状或支链状的氟代烷基、C3-C10的氟代环烷基、氟代苯基、被C1-C4的烷基或氟代烷基取代的苯基、樟脑基、樟脑醌基或叠氮萘酮基团。
进一步优选地,R1表示C1-C8的直链状或支链状的烷基、C1-C8的直链状或支链状的全氟代烷基、全氟代苯基、被C1-C4的烷基或全氟代烷基取代的苯基、樟脑基、樟脑醌基或叠氮萘酮基团。
作为优选实施方案,在上述通式(1)、(2)所示结构中,R2和R2’可相同,也可不同,各自独立地选自下列基团:氢,C1-C12的直链状或支链状的烷基,C3-C12的环烷基,C2-C12的直链状或支链状的链烯基,C2-C12的直链状或支链状的炔基,C1-C12的直链状或支链状的烷氧基,C1-C12的直链状或支链状的烷硫基,被1个以上的-O-、-S-、-O-CO-或-CO-O-中断的C2-C12的直链状或支链状的烷基或烷氧基,未取代或被C1-C4的烷基或烷氧基取代的C6-C10芳基,C6-C10芳基硫基,含有N、O和/或S的C4-C10的杂环基团例如噻吩基,N-吡咯基,吡啶基,吲哚基等;或者R2和R2’相连以形成五元环或六元环。
作为优选实施方案,在上述通式(1)、(2)所示结构中,
示例性地:当R2=R2’为烷基时,本发明上述通式(1)、(2)所示的光产酸剂可选自下列结构:
根据本发明的另一个方面,提供上述通式(1)、(2)所示酰亚胺磺酸酯类光产酸剂的制备方法,包括下列步骤:
1)4-X苯酐醇解形成酯化物(I);
2)上述酯化物与硼酸频那醇酯生成4-硼酸频那醇酯化合物(II);
3)6-X茚并噻吩/2-X茚并噻吩在碱性条件下与R2X/R2‘X反应制得4,4’-R2,R2‘茚并噻吩化合物,其中,R2与R2’相同或不同;
4)上述茚并噻吩化合物与酰卤R3X反应生成2-R3/3-R4、6/7-R3化合物;
5)步骤4)产物和步骤2)产物进行C-C偶联;
6)步骤5)产物水解并脱水成酐;
7)步骤6)产物与羟胺发生肟化反应,生成肟化合物;
8)步骤7)肟化合物与酰化试剂即R1-SO2X或(R1SO2)2O在碱性条件下于惰性溶剂中发生酯化反应,生成酰亚胺磺酸酯类光产酸剂,其中,X为卤素;
反应流程如下所示:
其中,X为卤素;Y为C1-C12的直链或支链的烷烃、环烷烃或C6-C12芳烃;R1、R2、R2’、R3及R4的定义如前文所述。
上述制备方法中使用的原料和试剂均为现有技术中的已知化合物,可通过商购获得或经已知工艺方便地制得。
步骤(4)中,步骤(3)的产物在碱性或酸性条件下与亚硝酸或亚硝酸烷基酯发生肟化反应,生成肟化合物。其中,所述的亚硝酸烷基酯可选自亚硝酸甲酯、亚硝酸乙酯、亚硝酸异丙酯、亚硝酸丁酯或亚硝酸异戊酯。肟化反应温度控制在-15-50℃之间,优选0-25℃。
步骤(5)中,肟化合物与酰化试剂即R1SO2X或(R1SO2)2O在碱性条件下于惰性溶剂中发生酯化反应,生成本发明所述的酰亚胺磺酸酯类化合物。酯化反应温度控制在-10-60℃之间,优选-5-5℃。
本发明的通式(1)(2)化合物属于非离子型光产酸剂,具有感光性基团和产酸性基团,磺酸酯基与肟结构直接相连,在活性能量射线照射下能够发生N-O键断裂而产生酸性较强的磺酸。该光产酸剂对波长300-450nm尤其是385nm和405nm(H线)的活性能量射线具有高灵敏度和较强吸收,在较低曝光量下即可较快地产酸。与此同时,它还具有良好的溶解性、热稳定性和化学稳定性。
有鉴于此,根据本发明的第三方面,提供一种酸产生方法,对上述光产酸剂即通式(1)、(2)化合物照射活性能量射线。非限制性地,活性能量射线可以是波长位于可见光区域的电磁波(可见光线)、波长位于紫外光区域的电磁波(紫外线)、波长位于红外光区域的电磁波(红外线)、以及X射线等波长位于非可见区域的电磁波等。但较为适宜地,所述活性能量射线为近紫外光区域、可见光区域的波长在300-450nm之间的活性能量射线,特别优选的是波长385nm和405nm(H线)的活性能量射线。
本发明的光产酸剂可用于光产酸剂的已知任意用途,例如抗蚀膜、液态抗蚀剂、负型抗蚀剂、正型抗蚀剂、MEMS用抗蚀剂、立体光刻和微立体光刻用材料等。其中,作为抗蚀剂组合物中的光产酸剂,可与具有酸解离性基团的树脂一并制备抗蚀剂应用于半导体光刻。
根据本发明的第四方面,提供一种抗蚀剂组合物,包括通式(1)和(2)所示的酰亚胺磺酸酯类光产酸剂。为便于表述组合物组分,下文中通式(1)和(2)所示酰亚胺磺酸酯类光产酸剂被理解为组合物中的组分(A);除非另有说明,光产酸剂(A)也表示相同的含义。
本发明的酰亚胺磺酸酯类光产酸剂应用于抗蚀剂组合物中,首先要能溶解于溶剂中。常用溶剂为有机溶剂,可选自:酯,如γ-丁内酯(GBL)、乙酸乙酯、乙酸丁酯、乳酸乙酯、丙酮酸甲酯等;酮,如丙酮、丁酮、环己酮、甲基异戊基酮和2-庚酮等;醚,如甲醚、乙醚、丙醚、丁醚、苯甲醚、乙基苄基醚、甲酚甲基醚、二苯醚、二苄基醚、丁基苯基醚等;多元醇及衍生物,如乙二醇、二甘醇、丙二醇、二丙二醇、乙二醇单乙酸酯、二甘醇单乙酸酯、丙二醇单乙酸酯、二丙二醇单乙酸酯、乙二醇单丙酸酯、二乙二醇单丙酸酯、丙二醇单丙酸酯、二丙二醇单丙酸酯、丙二醇单甲醚和丙二醇甲醚乙酸酯(PGMEA)等;芳族有机溶剂,如甲苯、二甲苯、乙苯、二乙苯、异丙苯、甲基异丙基苯和均三甲苯等;含氮极性溶剂,如N,N,N’,N’-四甲基脲、N-甲基-2-吡咯烷酮、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、六甲基磷酰胺、1,3-二甲基-2-咪唑啉酮和2-三甲基丙酰胺等。这些有机溶剂可单独使用或以两种以上的混合溶剂使用。
溶剂溶解抗蚀剂组合物中的各个组分,形成均匀的溶液,用于调节黏度和涂布性。上述溶剂优选丙二醇甲醚乙酸酯(PGMEA)、环己酮、和γ-丁内酯(GBL)中的一种或两种以上的混合。通常,优选以使组合物的固体成分浓度为5-30%(w/w)来进行溶剂量的选择。
本发明的抗蚀剂组合物可根据应用分为正型组合物和负型组合物。除酰亚胺磺酸酯类光产酸剂(1)和(2)外,正型组成物一般含有经由酸的作用而增大对碱显影液溶解性的树脂成分(B1)。在组合物图型形成过程中,经选择性曝光,曝光区域中的正型树脂中由保护基保护的酸不稳定基团,会在由光产酸剂产生的酸作用下脱保护,使其对碱显影液可溶。因此进行碱显影操作时,未曝光区域图型留存,形成正型图型。与正型组成物不同,除光产酸剂外,负型组合物使用在酸的作用下发生交联而不溶于有机系显影液的树脂-交联剂成分(B2)。曝光区域在由光产酸剂产生的酸催化下,树脂与交联剂反应形成不溶于有机系显影液的聚合物而留存,而未曝光区域被有机系显影液溶解、去除,最后形成负型图型。
本发明的正/负型抗蚀剂组合物中,酰亚胺磺酸酯类光产酸剂在活性能量射线照射下能够发生N-O键断裂而产生磺酸,经过PEB工艺,实现曝光区域和未曝光区域对显影液溶解性的差异。所述酰亚胺磺酸酯类光产酸剂产品可以单独一种使用,也可以两种以上混合使用。相对于组合物固体成分的质量,酰亚胺磺酸酯类光产酸剂的含量为0.01-5%,优选0.1-3%(w/w)。在该范围内时,既可良好地发挥对活性能量射线的感光度,又可良好地发挥对碱性显影液不溶部分的物性,提高显影效果。
本发明的正型抗蚀剂组合物中,树脂成分(B1)可以是由含碱可溶性酸性基团的乙烯基单体与视需要的含疏水基的乙烯基单体进行乙烯基聚合而获得,其中所述的碱可溶性酸性基团的氢原子的一部分或全部以作为保护基的酸解离性基团取代。所述的碱可溶性酸性基团可以是酚羟基、羧基或磺酸基,所述的酸解离性基团可在强酸存在下解离,所述强酸由光产酸剂(I)产生。
为便于描述,将所述的含碱可溶性酸性基团的乙烯基单体聚合形成的单元结构定义为酸基树脂,酸基树脂与含疏水基的乙烯基单体聚合形成的单元结构共同构成树脂成分(B1)。酸基树脂本身碱不可溶或碱难溶。
所述树脂成分(B1)中碱可溶性酸性基团可以是酚羟基、羧基或磺酸基。
其中,含酚羟基的树脂(B1-1)可选自酚醛清漆树脂、聚羟基苯乙烯-羟基苯乙烯的共聚物、羟基苯乙烯-苯乙烯的共聚物、羟基苯乙烯-苯乙烯-(甲基)丙烯酸衍生物的共聚物、苯酚-苯二甲醇缩合树脂、甲酚-苯二甲醇缩合树脂、含有酚羟基的聚酰亚胺、含有酚羟基的聚酰胺酸、苯酚-二环戊二烯缩合树脂等,优选酚醛清漆树脂、聚羟基苯乙烯-羟基苯乙烯的共聚物、羟基苯乙烯-苯乙烯的共聚物、羟基苯乙烯-苯乙烯-(甲基)丙烯酸衍生物的共聚物、苯酚-苯二甲醇缩合树脂、甲酚-苯二甲醇缩合树脂。含酚羟基的树脂可以单独一种使用,也可以两种以上混合使用。
所述酚醛清漆树脂是通过在酸催化剂下使具有酚羟基的芳香族化合物(以下简称为“酚”)与醛加成缩合而得到。所述酚类主要是烷基酚和芳香酚,可选自酚苯酚、邻甲酚、间甲酚、对甲酚、邻乙基苯酚、间乙基苯酚、对乙基苯酚、邻丁基苯酚、间丁基苯酚、对丁基苯酚、2,3-二甲苯酚、2,4-二甲苯酚、2,5-二甲苯酚、2,6-二甲苯酚、3,4-二甲苯酚、3,5-二甲苯酚、2,3,5-三甲基苯酚、3,4,5-三甲基苯酚、对苯酚、间苯二酚、对苯二酚、对苯二酚单甲醚、邻苯三酚、间苯三酚、羟基二苯基、双酚A、没食子酸、α-萘酚、β-萘酚等。所述醛类可选自甲醛、三聚甲醛、乙醛、糠醛、苯甲醛和硝基苯甲醛等。作为具体的酚醛清漆树脂,可选自苯酚-甲醛缩合酚醛清漆树脂、甲酚-甲醛缩合酚醛清漆树脂、苯酚-萘酚-甲醛缩合酚醛清漆树脂等。
所述含酚羟基的树脂分子量优选1000-50000左右。如上所述,可以根据需要向含酚羟基的树脂中引入交联基团,如结合在芳香族基团上的羧基、醇羟基和环状醚基反应。
所述羧基可源自:不饱和单羧酸,如(甲基)丙烯酸、丁烯酸及桂皮酸等;不饱和多元羧酸,如顺丁烯二酸、衣康酸、反丁烯二酸及柠康酸等;不饱和多元羧酸烷基(C1-C10)酯,如顺丁烯二酸单烷基酯、反丁烯二酸单烷基酯及柠康酸单烷基酯等;及它们的盐,如碱金属盐(钠盐及钾盐等)、碱土金属盐(钙盐及镁盐等)、胺盐及铵盐等。羧基基团优选源自(甲基)丙烯酸。
作为含羧基的树脂的优选实例,丙烯酸树脂是(甲基)丙烯酸与具有不饱和键的其他单体共聚而得到的树脂。与(甲基)丙烯酸共聚的单体可选自不同于(甲基)丙烯酸的不饱和羧酸、(甲基)丙烯酸酯、(甲基)丙烯酰胺、烯丙基化合物、乙烯基醚等。(甲基)丙烯酸酯可选自(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸戊酯、(甲基)丙烯酸叔辛酯等。在不具有环氧基的(甲基)丙烯酸酯中,优选具有脂环式骨架的(甲基)丙烯酸酯;在具有脂环式骨架的(甲基)丙烯酸酯中,脂环基团可以是单环或多环的,单环式脂环基可选自环戊基和环己基,多环式脂环基可选自降冰片基、异冰片基、三环壬基等。
所述磺酸基可源自:乙烯基磺酸、(甲基)烯丙基磺酸、苯乙烯磺酸、α-甲基苯乙烯磺酸、2-(甲基)丙烯酰胺基-2-甲基丙磺酸及其盐类,如碱金属(钠及钾等)盐、碱土金属(钙及镁等)盐、1-3级胺盐、铵盐及四级铵盐等。
含碱可溶性酸性基团树脂的亲水性-亲油性均衡(HLB)值根据碱可溶性树脂的树脂骨架而范围不同,一般为4-19,优选6-17。HLB值≥4,则进行显影时显影性更良好;HLB值≤19,则硬化物的耐水性更良好。
酸基树脂在树脂成分(B1)中的含量为1-100%(w/w),优选为10-70%(w/w)。在该范围内时,可以使抗蚀剂组合物获得具有更好的显影性。
所述含疏水基的乙烯基单体可选自(甲基)丙烯酸酯和芳香族烯烃单体等。
所述(甲基)丙烯酸酯可选自:(甲基)丙烯酸C1-C20烷基酯,如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸正己酯、(甲基)丙烯酸-2-乙基己酯等;含脂环基的(甲基)丙烯酸酯,如(甲基)丙烯酸二环戊基酯、(甲基)丙烯酸二环戊烯酯、(甲基)丙烯酸异冰片酯等。
所述芳香族烯烃单体可选自具有苯乙烯骨架的烷烃和芳烃,如苯乙烯、α-甲基苯乙烯、乙烯基甲苯、2,4-二甲基苯乙烯、乙基苯乙烯、异丙基苯乙烯、丁基苯乙烯、苯基苯乙烯、环己基苯乙烯、苄基苯乙烯和乙烯基萘等。
上述含疏水基的乙烯基单体聚合形成的单元结构在树脂成分(B1)中的含量优选为30-90%(w/w)。在该范围内时,可以使抗蚀剂组合物获得具有更好的显影性。
作为保护基的酸解离性基团可选自:被取代的甲基、1-被取代乙基、1-分支烷基、硅烷基、锗烷基、烷氧基羰基、酰基及环式酸解离性基团等。酸解离性基团可单独一种使用,也可组合两种以上使用。
所述被取代的甲基,可选自:甲氧基甲基、甲硫基甲基、乙氧基甲基、乙硫基甲基、甲氧基乙氧基甲基、苄氧基甲基、苄硫基甲基、苯甲酰甲基、溴苯甲酰甲基、甲氧基苯甲酰甲基、甲硫基苯甲酰甲基、α-甲基苯甲酰甲基、环丙基甲基、苄基、二苯基甲基、三苯基甲基、溴苄基、硝基苄基、甲氧基苄基、甲硫基苄基、乙氧基苄基、乙硫基苄基、胡椒基、甲氧基羰基甲基、乙氧基羰基甲基、正丙氧基羰基甲基、异丙氧基羰基甲基、正丁氧基羰基甲基、叔丁氧基羰基甲基等。
所述1-被取代的乙基,可选自:1-甲氧基乙基、1-甲硫基乙基、1,1-二甲氧基乙基、1-乙氧基乙基、1-乙硫基乙基、1,1-二乙氧基乙基、1-乙氧基丙基、1-丙氧基乙基、1-环己氧基乙基、1-苯氧基乙基、1-苯硫基乙基、1,1-二苯氧基乙基、1-苄氧基乙基、1-苄硫基乙基、1-环丙基乙基、1-苯基乙基、1,1-二苯基乙基、1-甲氧基羰基乙基、1-乙氧基羰基乙基、1-正丙氧基羰基乙基、1-异丙氧基羰基乙基、1-正丁氧基羰基乙基、1-叔丁氧基羰基乙基等。
所述1-分支烷基,可选自:异丙基、第二丁基、叔丁基、1,1-二甲基丙基、1-甲基丁基、1,1-二甲基丁基等。
所述硅烷基,可选自:三甲基硅烷基、乙基二甲基硅烷基、甲基二乙基硅烷基、三乙基硅烷基、异丙基二甲基硅烷基、甲基二异丙基硅烷基、三异丙基硅烷基、叔丁基二甲基硅烷基、甲基二叔丁基硅烷基、三叔丁基硅烷基、苯基二甲基硅烷基、甲基二苯基硅烷基、三苯基硅烷基等。
所述锗烷基,可选自:三甲基锗烷基、乙基二甲基锗烷基、甲基二乙基锗烷基、三乙基锗烷基、异丙基二甲基锗烷基、甲基二异丙基锗烷基、三异丙基锗烷基、叔丁基二甲基锗烷基、甲基二叔丁基锗烷基、三叔丁基锗烷基、苯基二甲基锗烷基、甲基二苯基锗烷基、三苯基锗烷基。
所述烷氧基羰基,可选自:甲氧基羰基、乙氧基羰基、异丙氧基羰基、叔丁氧基羰基等。
所述酰基,可选自:乙酰基、丙酰基、丁酰基、庚酰基、己酰基、戊酰基、特戊酰基、异戊酰基、月桂酰基、肉豆蔻酰基、软脂酰基、硬脂酰基、乙二酰基、丙二酰基、丁二酰基、戊二酰基、己二酰基、庚二酰基、辛二酰基、壬二酰基、癸二酰基、丙烯酰基、丙炔酰基、甲基丙烯酰基、丁烯酰基、油酰基、顺丁烯二酰基、反丁烯二酰基、中康酰基、莰二酰基、苯甲酰基、邻苯二甲酰基、间苯二甲酰基、对苯二甲酰基、萘甲酰基、甲苯甲酰基、氢阿托酰基、阿托酰基、桂皮酰基、呋喃甲酰基、噻吩甲酰基、烟酰基、异烟酰基、对甲苯磺酰基、甲磺酰基等。
所述环式酸解离性基团,可选自:环丙基、环戊基、环己基、环己烯基、4-甲氧基环己基、四氢吡喃基、四氢呋喃基、四氢噻喃基、四氢硫呋喃基、3-溴四氢吡喃基、4-甲氧基四氢吡喃基、4-甲氧基四氢噻喃基、3-四氢噻吩-1,1-二氧化物基等。
除上述基团外,作为保护基的酸解离性基团还可选自如下基团中的至少一种:
其中,
R8、R9、R10各自独立地表示C1-C6的直链状或支链状的烷基、C1-C10的直链状或支链状的氟化烷基,且R8、R9、R10中任何两个适于彼此键合成环;
R11、R12和R13各自独立地表示C1-C20的烃基,且R11、R12、R13中的任何两个适于彼此键合成环;
R14表示C1-C6的直链状或支链状的烷基、C3-C6的环烷基,且n为0或1。
具体的,在式(a)中,当R8、R9和R10为烷基时,示例性的可选自甲基、乙基、正丙基、异丙基、正丁基,异丁基、仲丁基、叔丁基、正戊基、异戊基、叔戊基、正己基、正庚基、正辛基、2-乙基正己基、正壬基基、正癸基等;当R8、R9和R10中的任何两个基团彼此键合形成环时,优选具有C5-C20的单环或聚环的脂族烃,示例性的可选自环戊烷、环己烷、环庚烷、环辛烷、金刚烷、降冰片烷、三环癸烷、四环癸烷等;通过结合R8、R9和R10中的任意两个基团形成的环可以具有取代基,例如羟基、氰基和氧原子(=O),以及具有C1-C4的直链或支链烷基。优选地,式(a)可以选择以下分子式(式a1-式a6)的基团;
具体的,在式(b)中,R11、R12和R13为具有C1-C20的脂肪族或/和芳香族的烃基。当R11、R12和R13为脂族烃基时,可以是直链结构和环状结构,直链结构可选自甲基、乙基、正丙基、异丙基、正丁基和异丁基、仲丁基、叔丁基、正戊基、异戊基、叔戊基、正己基、正庚基、正辛基、2-乙基-正己基、n-壬基、正癸基和正十一烷基等;环状结构可选自环丙基、环丁基、环戊基、环己基、环庚基、环壬基、环癸基、环十一烷基、环十二烷基,以及以下分子式的多环基团(式b1-式b8);
以及,在式(b)中,当R11、R12和R13是芳香族烃基时,可选自苯基、萘基、蒽基、联苯基、菲基和芴基。当R11、R12和R13同时含脂肪族和芳香族基团时,可选自苄基、苯乙基、3-苯基-正丙基、4-苯基-正丁基、α-萘基甲基、β-萘基甲基、2-(α-萘基)乙基和2-(β-萘基)乙基等。芳环可被取代或部分取代,取代基选自卤素原子、羟基、具有C1-C10的烷基或烷氧基,C2-C10的烷酰基和烷酰氧基。式(b)中,R11优选为氢原子,R12优选为甲基,R13优选为乙基、异丁基、环己基、2-乙基正己基或十八烷基;当R12和R13彼此键合形成环时,优选含有O、S或N原子的C4-C6杂环;当R11和R12彼此键合形成环时,优选C3-C12元饱和脂肪族烃环。
优选地,式(b)还可选自以下分子式(式b9-式b14)的基团:
具体的,所述式(c)可选自叔丁氧羰基和叔丁氧羰基甲基。
作为保护基的酸解离性基团,优选叔丁基、苄基、1-甲氧基乙基、1-乙氧基乙基、三甲基硅烷基、叔丁氧基羰基、叔丁氧基羰基甲基、四氢吡喃基、四氢呋喃基、四氢噻喃基及四氢硫呋喃基等。
通过调节酸解离性基团的含量可以调整抗蚀剂组合物的显影效果,为了进一步提高其显影效果,优选地,酸基树脂中酸解离性基团的导入率(酸解离性基团的数量相对于未经保护的酸性基团与酸解离性基团的总和的比例)为15-100%。
酸基树脂的平均分子量为1,000-150,000。酸基树脂的平均分子量包括但不限于上述范围,而将其限定在上述范围内有利于提高其耐水性,从而有利于提高其显影图案的显影效果。更优选地,酸基树脂的平均分子量为3,000-100,000。
本发明的负型抗蚀剂组合物中,树脂-交联剂成分(B2)主要是含酚羟基的树脂(B2-1)和交联剂(B2-2)。
含酚羟基的树脂(B2-1)可使用与前文所述B1-1相同。所述B2-1占组合物固体成分的30-90%(w/w),优选40-80%(w/w)。
交联剂(B2-2)作为在光产酸剂(A)产的酸的催化下,将含酚羟基的树脂(B2-1)交联聚合的化合物,可选自双酚A系环氧化合物、双酚F系环氧化合物、双酚S系环氧化合物、酚醛清漆树脂系环氧化合物、可溶酚醛树脂系环氧化合物、聚(羟基苯乙烯)系环氧化合物、氧杂环丁烷化合物、含羟甲基的三聚氰胺化合物、含羟甲基的苯并胍胺化合物、含羟甲基的脲化合物、含羟甲基的酚化合物、含烷氧基烷基的三聚氰胺化合物、含烷氧基烷基的苯并胍胺化合物、含烷氧基烷基的脲化合物、含烷氧基烷基的酚化合物、含羧甲基的三聚氰胺树脂、含羧甲基的苯并胍胺树脂、含羧甲基的脲树脂、含羧甲基的酚树脂、含羧甲基的三聚氰胺化合物、含羧甲基的苯并胍胺化合物、含羧甲基的脲化合物及含羧甲基的酚化合物等。这些交联剂中,优选含甲氧基甲基的三聚氰胺化合物(例如六甲氧基甲基三聚氰胺等)、含甲氧基甲基的甘脲化合物及含甲氧基甲基的脲化合物等。示例性地,含甲氧基甲基的三聚氰胺化合物以CYMEL300、CYMEL301、CYMEL303、CYMEL305等商品名而市售,含甲氧基甲基的甘脲化合物以CYMEL1174等商品名而市售,含甲氧基甲基的脲化合物以MX290等商品名而市售。
考虑到残膜率的降低和分辨率的问题,相对于含酚羟基的树脂(B2-1)中的所有酸性官能基,交联剂(B2-2)的含有量通常为10mol-50mol%,优选15mol-40mol%。
作为任选组分,上述正型或负型抗蚀剂组合物中还可包含芳香族羧酸化合物(C),即至少一个羧酸基团键合到芳香族基团上。示例性地,正型抗蚀剂组合物中,芳香族羧酸化合物可以促进组合物中树脂成分曝光后的脱保护反应。
芳香族羧酸化合物(C)可以选择低分子量芳香族羧酸化合物或高分子量芳香族羧酸化合物中的至少一种。
在芳香族羧酸化合物中,除了羧酸基团外,还可以具有1个以上的取代基,所述取代基可选自:卤素、羟基、巯基、硫化物基团、甲硅烷基、硅烷醇基团、硝基、亚硝基、磺酸酯基、亚膦酰基和膦酸酯基;烷基、烯基、环烷基、环烯基、芳基和芳烷基;含O、Si、N等杂原子的键如醚键、硫醚键、羰基键、硫代羰基键、酯键、酰胺键、氨基甲酸酯键和亚胺基键、碳酸酯键、磺酰基键、亚磺酰基键和偶氮键等。上述取代基可以是直链、支链或环状的。作为芳香族羧酸化合物上的取代基,优选C1-C12的烷基、芳基、烷氧基和卤素。
低分子量芳香族羧酸化合物可以是单羧酸化合物或多价羧酸化合物。示例性地,低分子量芳香族羧酸化合物可选自:苯甲酸;羟基苯甲酸,如水杨酸、间羟基苯甲酸和对羟基苯甲酸等;烷基苯甲酸,如邻甲基苯甲酸、间甲基苯甲酸和对甲基苯甲酸;卤代苯甲酸,如邻氯苯甲酸、间氯苯甲酸、对氯苯甲酸、邻溴苯甲酸、间溴苯甲酸和对溴苯甲酸;烷氧基苯甲酸,如邻甲氧基苯甲酸、间甲氧基苯甲酸、对甲氧基苯甲酸、邻乙氧基苯甲酸、间乙氧基苯甲酸和对乙氧基苯甲酸;胺基苯甲酸,如邻胺基苯甲酸、间胺基苯甲酸和对胺基苯甲酸;酰氧基苯甲酸,如邻乙酰氧基苯甲酸、间乙酰氧基苯甲酸和对乙酰氧基苯甲酸;萘甲酸,如1-萘甲酸和2-萘甲酸;羟基萘酸,如1-羟基-2-萘甲酸、1-羟基-3-萘甲酸、1-羟基-4-萘甲酸、1-羟基-5-萘甲酸、1-羟基-6-萘甲酸、1-羟基-7-萘甲酸、1-羟基-8萘甲酸、2-羟基-1-萘甲酸、2-羟基-3-萘甲酸、2-羟基-4-萘甲酸、2-羟基-5-萘甲酸、2-羟基-6-萘甲酸、2-羟基-7-萘甲酸和2-羟基-8-萘甲酸;胺基萘酸,如1-胺基-2-萘甲酸、1-胺基-3-萘甲酸、1-胺基-4-萘甲酸、1-胺基-5-萘甲酸、1-胺基-6萘甲酸、1-胺基-7-萘甲酸、1-胺基-8-萘甲酸、2-胺基-1-萘甲酸、2-胺基-3-萘甲酸、2-胺基-4-萘甲酸、2-胺基-5-萘甲酸、2-胺基-6-萘甲酸,2-胺基-7-萘甲酸和2-胺基-8-萘甲酸;烷氧基萘酸,如1-甲氧基-2-萘甲酸、1-甲氧基-3-萘甲酸、1-甲氧基-4-萘甲酸、1-甲氧基-5-萘甲酸、1-甲氧基-6萘甲酸、1-甲氧基-7-萘甲酸、1-甲氧基-8萘甲酸、2-甲氧基-1-萘甲酸、2-甲氧基-3-萘甲酸、2-甲氧基-4-萘甲酸、2-甲氧基-5-萘甲酸、2-甲氧基-6-萘甲酸、2-甲氧基-7-萘甲酸、2-甲氧基-8-萘甲酸、1-乙氧基-2-萘甲酸、1-乙氧基-3-萘甲酸、1-乙氧基-4-萘甲酸、1-乙氧基-5-萘甲酸、1-乙氧基-6-萘甲酸、1-乙氧基-7-萘甲酸、1-乙氧基-8-萘甲酸、2-乙氧基-1-萘甲酸、2-乙氧基-3-萘甲酸、2-乙氧基-4-萘甲酸、2-乙氧基-5-萘甲酸、2-乙氧基-6-萘甲酸、2-乙氧基-7-萘甲酸和2-乙氧基-8-萘甲酸等;苯二甲酸,如邻苯二甲酸、对苯二甲酸和间苯二甲酸;萘二甲酸,如1,2-萘二甲酸、1,3-萘二甲酸、1,4-萘二甲酸、1,5-萘二甲酸、1,6-萘二甲酸、1,7-萘二甲酸、1,8-萘二甲酸、2,3-萘二甲酸、2,6-萘二甲酸和2,7-萘二甲酸;联苯羧酸,如1,1′-联苯-4-羧酸、1,1′-联苯-3-羧酸和1,1′-联苯-2-羧酸;联苯二羧酸,如1,1′-联苯-4,4′-二羧酸、1,1′-联苯-3,3′-二羧酸、1,1′-联苯-2,2′-二羧酸、1,1′-联苯-3,4′-二羧酸、1,1′-联苯-2,4′-二羧酸和1,1′-联苯-2,3′-二羧酸;三价或更高价的芳香族多元羧酸,如均苯四酸、偏苯三酸和偏苯三酸;羟基苯二羧酸,如5-羟基间苯二甲酸、4-羟基间苯二甲酸和2-羟基间苯二甲酸;二羟基苯二羧酸,如2,5-二羟基对苯二甲酸、2,6-二羟基间苯二甲酸、4,6-二羟基间苯二甲酸、2,3-二羟基邻苯二甲酸、2,4-二羟基邻苯二甲酸和3,4-二羟基邻苯二甲酸等;吡啶羧酸,如吡啶-2-羧酸、吡啶-3-羧酸和吡啶-4-羧酸等;吡啶二羧酸,如吡啶-2,5-二羧酸、吡啶-3,5-二羧酸、吡啶-2,6-二羧酸和吡啶-2,4-二羧酸等;嘧啶羧酸,如嘧啶-2-羧酸、嘧啶-4-羧酸、嘧啶-5-羧酸和嘧啶-6-羧酸;以及嘧啶二羧酸,如2,6-嘧啶二羧酸和2,5-嘧啶二羧酸。这些低分子量的芳香族羧酸化合物可以单独使用或两种以上组合使用。
高分子量芳香族羧酸化合物可以是芳香族基团上结合有羧酸基团的芳香族高分子化合物。适宜地,其单体具有结合到芳香族基团上的羧酸基团和不饱和双键,并且不包括被保护基保护的酸不稳定性基团。所述高分子化合物可以是均聚物,也可以是共聚物。作为优选的与上述单体一并使用的共聚单体,可以使用上述制备丙烯酸树脂的单体,如(甲基)丙烯酸、不同于(甲基)丙烯酸的不饱和羧酸、(甲基)丙烯酸酯、(甲基)丙烯酰胺、烯丙基化合物、乙烯基醚、乙烯基酯和苯乙烯。
作为任选组分,上述正型或负型抗蚀剂组合物中还可包含架桥基化合物,所述架桥基化合物含有至少一个交联基团。所述交联基团可选自(但不限于)环氧基、氧杂环丁烷基中的至少一种。架桥基化合物包括可以是架桥基低分子化合物,也可以是架桥基高分子化合物,或者两者的组合。
架桥基低分子化合物可选自:双官能或更高官能的多官能环氧化合物、多官能氧杂环丁烷化合物中的至少一种。
多官能环氧化合物可选自:双官能环氧树脂,如双醛A型环氧树脂、双酚S型环氧树脂;缩水甘油酯型环氧树脂,如二聚酸缩水甘油酯、三缩水甘油酯;缩水甘油胺型环氧树脂,如四缩水甘油基氨基二苯甲烷、四缩水甘油基双氨基甲基环己烷;杂环环氧树脂,如三缩水甘油基异氰脲酸酯;多官能环氧树脂,如间苯三酚三缩水甘油基醚、四羟基苯基乙烷四缩水甘油基醚。脂环式环氧化合物还优选作为多官能环氧化合物,易于形成高度透明的膜。
多官能氧杂环丁烷化合物可选自3,3′-(氧双亚甲基)双(3-乙基氧杂环丁烷)、4,4-双[(3-乙基-3-氧杂环丁烷基)甲基]联苯和3,7-双(3-氧杂环丁烷基)-5-氧杂壬烷等中的至少一种。
架桥基高分子化合物可选自:含环氧基的树脂、含不饱和双键的树脂中的至少一种。含环氧基树脂可以通过含环氧基的单体或单体混合物聚合而成,可选自酚醛清漆环氧树脂,如苯酚酚醛清漆型环氧树脂,溴化苯酚酚醛清漆型环氧树脂等;脂环族环氧树脂,如二环戊二烯型酚醛树脂的环氧化产物;以及芳族环氧树脂,如萘型酚醛树脂的环氧化产物。
任选地,抗蚀剂组合物中还可包含该领域中的常规助剂,在此不再赘述。
应用本发明的抗蚀剂组合物时,首先可使用例如旋转涂布的方法将溶解或分散于有机溶剂而成的树脂溶液涂布于基板上,然后藉由加热使溶剂挥发,从而在基板上形成抗蚀膜,然后进行配线图案形状的光照射(即曝光),接着在进行曝光后的加热处理(PEB)后,进行碱性显影,形成配线图案。
涂布后的树脂溶液的干燥条件根据所使用的溶剂而不同,优选于50℃-150℃下、在1-30分钟的范围内实施,藉由干燥后的残留溶剂量(重量%)等来适当决定。
在基板上形成抗蚀膜之后,用光照射配线图案形状。光照射可使用低压汞灯、中压汞灯、高压汞灯、超高压汞灯、氙气灯、金属卤素灯、电子束辐照装置、X射线辐照装置、激光(如氩激光、染料激光、氮气激光、LED、氦气镉激光器)等,优选高压汞灯和LED灯。
曝光后加热处理(PEB)的温度通常为40℃-200℃,优选60℃-150℃。若小于40℃,则无法充分进行脱保护反应或交联反应,因此曝光部与未曝光部的溶解性的差异不足而无法形成图案;若高于200℃,则存在生产性降低的问题。上述加热时间,通常为0.5分钟-30分钟。
用碱显影液进行显影,碱显影方法包括使用碱显影剂。碱性显影剂可选自0.1-10%(w/w)的氢氧化四甲基铵、氢氧化钠、氢氧化钾、碳酸氢钠的水溶液,碱性显影剂还可包含水溶性有机溶剂,如甲醇、乙醇、异丙醇、四氢呋喃、N-甲基吡咯烷酮等。显影方法可选自浸渍法、喷淋法和喷雾法,优选喷雾法。显影剂的温度优选在25-40℃下使用,显影时间根据抗蚀膜的厚度适当确定,最后以获得对应于掩模的图案。
根据本发明的第五方面,提供上述抗蚀剂组合物的应用,包括将抗蚀剂组合物应用于电子组件的保护膜、层间绝缘材料、图型转移材料的制备中。
由于本发明的抗蚀剂组合物具有对波长300-450nm(尤其是365nm、385nm和405nm)的活性能量射线具有高灵敏度和较强吸收,在较低曝光量下即可较快地产酸,同时还具有较好的溶解性、热稳定性和化学稳定性。因而采用上述抗蚀剂组合物经过图形显影化方法形成保护膜、层间绝缘材料或图形转移材料时能够使相应的电子组件具有更好的综合性能。
具体地,上述应用可包括将抗蚀剂组合物用于形成层间绝缘膜,用于液晶显示装置的TFT、面板;也可作为保护膜用于滤色器、间隔柱;还可作为PS光刻胶、BCS光刻胶用于图型转移。
所述电子组件包括但不限于液晶显示装置、有机EL显示装置,Micro-LED、Mini-LED和量子点LED显示装置等电子组件。
根据本发明的第六方面,提供一种电子组件,包含由本发明的抗蚀剂组合物制备而成的保护膜、层间绝缘材料或图型转移材料。
基于非常优异的感光性能以及热稳定性、溶解性和化学稳定性,本发明的酰亚胺磺酸酯类光产酸剂还可以应用于其它感光领域。
具体实施方式
以下结合实施例来详细说明本发明,但不应将其理解为对本发明保护范围的限制。
制备实施例
实施例1
向四口烧瓶中加入251.15g 6-溴-茚并噻吩、32.24g四丁基溴化铵和1200.00gDMSO,开启搅拌并降温至-5-0℃,然后缓慢加入1066.67g液碱(30%w/w)并搅拌0.5h,将287.75g 1-溴丁烷滴加至体系中,滴加完毕后,升温至室温并保温6小时;倒入500.00g纯水和1200.00g二氯甲烷(DCM),搅拌0.5h。分离有机相,水相用250.00g的DCM萃取3次;合并有机相,用250.00g水清洗一次。加入7.55g活性炭,搅拌0.5h后过滤;收集滤液,蒸馏DCM,加入800.00g正己烷-5-0℃析晶,得到6-溴-4,4’-二丁基茚并噻吩347.10g。
将182.10g浓硫酸缓慢加入36.44g发烟硝酸中形成硝酸溶液。将200.00g付克产物和1000.00g DCM加入1000ml四口烧瓶中,开启搅拌溶解。降温在5-10℃,滴加硝酸溶液,约2h滴加完毕,取样中控原料剩余<0.5%时,停止反应,将反应液倒入750g冰水中,搅拌20min,静置分液,取下层有机相,分别用250.00g纯水洗涤3次,有机相常压蒸馏至无明显液体流出,加入200.00g丙酮,降温至5-15℃下,搅拌析晶,60℃鼓风干燥得到161.78g淡黄色固体。
向1000ml四口烧瓶中(带有分水器)加入100.02g 4-溴邻苯二甲酸酐、100.20g浓硫酸和500.00g正丁醇,搅拌升温至90℃,6h后HPLC中控产物峰≥95.00%,停止搅拌,降温至10-20℃。向四口烧瓶中加入纯水400g,搅拌5min,静置10min,分去水层。有机层加入纯水200g,搅拌5min,静置10min后分液。向有机层中加入二氯甲烷450.00g、纯水200.00g,搅拌5min,静置10min后分液。有机层继续水洗(每次200.00g)至PH=7。有机层加入无水硫酸钠1.52g,抽滤。有机层在1000ml四口烧瓶中,120℃减压蒸馏至无馏出,得到淡黄色油状液体129.76g。
向2000ml四口烧瓶中加入1000.05g甲苯、107.19g4-溴邻苯二甲酸正丁酯、83.80g频那醇二硼、1.38g Pd2(dba)3、91.22g乙酸钾、2.15g x-phos,搅拌升温至110℃,保温回流2小时HPLC中控4-溴邻苯二甲酸≤0.50%,停止反应。降温至30℃,加纯水110.00g,搅拌10min分液,有机相加入活性炭2.00g脱色,再分别用110.00g纯水水洗两次(每次用水100g,水洗温度20~30℃),减压去除甲苯,得到暗红色油状液体98.58g。
向2000ml四口烧瓶中(带有冷凝器)加入650.00g甲苯、80.86g 4-硼酸酯邻苯二甲酸正丁酯、77.02g 6-溴-2-硝基-4,4’-二丁基茚并噻吩、1.56g Pd(PPh3)2Cl2、130.33g碳酸铯,开启搅拌、油浴加热至110℃,保温回流,HPLC中控当4-硼酸酯邻苯二甲酸正丁酯≤2.00%和6-溴-2-硝基-4,4’-二丁基茚并噻吩≤0.50%时停止反应。移去油浴、降温至30℃,加水250.00g,搅拌10min,然后分离去除水相,加入活性炭3.0g进行脱色,然后再水洗两次(每次100.00g,水洗温度20-30℃)。减压蒸馏去除甲苯,过柱(二氯甲烷,200-300目硅胶),得到深色油状液体96.57g。
取上述油状液体60.58g溶于150.00g无水乙醇中,搅拌均匀配制成溶液A。取12.02g氢氧化钠溶于180.20g纯水中,搅拌均匀配制成溶液B。将A、B溶液分别加入1000ml四口烧瓶中,水浴搅拌升温至50℃,保温反应;HPLC中控二甲酸正丁酯无剩余时停止反应。60℃减压蒸馏至无产物馏出,加入60.00g水和280.00g二氯甲烷萃取分液。水相中滴加浓盐酸至pH值为1-2,在冰水浴中搅拌10分钟,抽滤、烘干得到46.27g固体。
向250ml四口烧瓶中加入45.00g上述产物、112.52g乙酸酐,开启搅拌、油浴升温至70℃,保温2h,HPLC中控体系不再发生变化,停止搅拌,降温至10-20℃。反应完的溶液于冰水浴中降温至≤5℃,冰水浴中静置析出产物24.29g。
向500ml四口烧瓶中(带有冷凝器)加入上述产物24.29g,100.71g甲醇、4.46g盐酸羟胺、5.30g醋酸铵,开启搅拌、油浴加热至80℃,保温回流6h停止反应。降温至20-40℃,加入活性炭2.0g脱色,加水25.00g、二氯甲烷80.00g,搅拌分液,再室温水洗两次(每次用水25.00g),蒸馏甲醇,低温结晶抽滤,得到红色固体,用二氯甲烷溶解,盐酸调PH=2,过滤得到10.27g黄色固体产物。
向500ml四口烧瓶中加入50.23g二氯甲烷、10.00肟化产物、1.69g吡啶,开启搅拌,冰水浴降温至0-5℃,滴加6.33g三氟甲基磺酸酐,温度控制在0-5℃,滴加结束后继续保温搅拌1.0h,HPLC中控酰亚胺峰≤1.00%。降温至20-40℃,加入活性炭1.00g脱色;室温水洗两次(每次用水15.00g),用盐酸调PH=2,再室温水洗两次(每次用水15.00g),用氨水调PH=8,水洗(每次用水15.00g)至PH=7,有机相过200-300目硅胶柱,然后60℃常压蒸馏至二氯甲烷无馏出,加入膜过滤正己烷40.05g,搅拌,放入0-5℃低温槽,搅拌0.5h,抽滤,10.00g正己烷漂洗、抽干,真空干燥得到成品7.66g黄色固体,即为上文结构式(5)所示的化合物。
通过1H NMR对产物结构进行表征,结果如下:1H NMR(400MHz,CDCl3)δ7.95-7.86(m,2H),7.62(dd,J=8.4,2.4Hz,1H),7.57-7.51(m,3H),7.38(t,J=1.4Hz,1H),2.05-1.91(m,4H),1.51-1.31(m,8H),0.88(t,J=7.5Hz,6H)。
实施例2-24
参照实施例1的方法,更换相应原料,合成如下表1中所示的其他光产酸剂化合物。
表1
比较例化合物比较例1
非离子光产酸剂(A*1)
性能评价
分别对实施例合成的光产酸剂化合物和比较例化合物进行性能评价,评价指标包括365nm、385nm、405nm和436nm的摩尔吸光系数、溶解性和化学稳定性。
(1)摩尔吸光系数
利用乙腈将化合物稀释成0.25mmol/L,使用紫外可见光谱光度计在200-600nm的范围测定1cm的比色皿长度的吸光度。由下述公式算出各波长下的摩尔吸光系数ε。
ε(L·mol-1·cm-1)=A/(0.00025mol/L*1cm)
式中,A表示各波长下的吸光度。
(2)溶解性
高溶解度不仅使光产酸剂化合物纯化容易,且可以使光产酸剂化合物能够在光阻及不同溶剂系统中扩大使用的浓度范围。分别取光酸样品1.0000g,25℃下逐渐加入溶剂,直至各试管内固体全部溶清,记录所用溶剂的质量,溶解度由下述公式表示。
在含光产酸剂的配方组合物中,含有多种助剂,以实现组合物的储存稳定性和满足后续工艺的条件。这要求光产酸剂不仅不能影响组合物中的助剂,自身也要在其中稳定存在,不会发生任何化学反应。以三乙胺为考察助剂,以10%光产酸剂(w/w)的添加量,与光产酸剂一起溶于PGMEA中,密封后在室温下储存168h,用HPLC法考察光产酸剂的储存稳定性。结果分级如下:
◎-HPLC含量≥95.00%;
○-HPLC含量85.00-95.00%;
×-HPLC含量<85.00%。
评价结果如表2中所示。
表2
表2的测试结果显示,本发明的光产酸剂在365-436nm处具有较高的摩尔吸光系数,吸光能力强,可充分利用光能,能够确保在抗蚀剂应用中具有较高的利用率,性能明显优于对比例1的现有产品,且在化学稳定性方面也具有明显优势。
产业可利用性
以下结合组合物实施例和对比例,对产业可利用性进行说明。
抗蚀剂组合物的实施例
将各原料均匀溶解在100%PGMEA(丙二醇甲醚乙酸酯)中,得到固体成分浓度为40%(w/w)的抗蚀剂组合物。其中,酰亚胺磺酸酯类光产酸剂(A)、树脂组分(B)、芳香族羧酸化合物(C)和碱(三乙胺)的组分类型及含量如表3中所示。
实施例25
其中树脂组分(B)采用B1类型的树脂,由式B11、式B12和式B13所示的重复单元构成,各重复单元右下的数值表示该重复单元在树脂中的含量(质量%)。B2树脂的重均分子量约为15000。
酰亚胺磺酸酯类光产酸剂(A)为实施例5的光产酸剂。
芳香族羧酸化合物(C)采用C1类型化合物,由摩尔比为1:1的双酚芴与2,3,3′,4′-联苯四羧酸二酐反应得到。
实施例26-33
与实施例25的区别分别在于:酰亚胺磺酸酯类光产酸剂(A)分别采用实施例3、5、7、8、11、13、14、17的光产酸剂。
其余组分类型和含量如表3中所示。
实施例34
与实施例25的区别在于:树脂组分(B)采用B2类型的树脂,由式B21、式B22、式B23和B24所示的重复单元构成,各重复单元右下的数值表示该重复单元在树脂中的含量(质量%)。B2树脂的重均分子量约为15000。
其余组分类型和含量如表3所示。
实施例35
与实施例25的区别在于:树脂组分(B)采用B3类型的树脂,由式B31和式B32所示的重复单元构成,各重复单元右下的数值表示该重复单元在树脂中的含量(质量%)。B3树脂的重均分子量约为15000。
其余组分类型和含量如表3所示。
实施例36-37
与实施例25的区别在于:光产酸剂的含量不同。
其余组分类型和含量如表3所示。
对比例2
与实施例25的区别在于:采用对比例光产酸剂A*1。
组分类型和含量如表3所示。
对比例3
与实施例25的区别在于,
(1)使用双酚芴与四氢邻苯二甲酸酐以1:1的摩尔比反应而得到的芳香族羧酸化合物C2。
(2)其余组分类型和含量如表3所示。
对比例4
与实施例25的区别在于,
(1)使用双酚芴与聚甲基丙烯酸以1:1的摩尔比反应而得到的芳香族羧酸化合物C3。
(2)加入1质量份的2-异丙基噻吨酮作为光敏剂。
(3)其余组分类型和含量如表3所示。
将实施例25-37、对比例2-4制备的抗蚀剂组合物通过以下方法评价灵敏度和解像性,结果记录在表3中。
(1)感度评价方法
在各硅片上,以能够形成图案的膜厚为4.5μm的膜厚涂布各实施例和对比例的抗蚀剂组合物,形成涂膜。将形成的涂膜在120℃下预烘烤90秒。预烘烤后,改变曝光量,用掩模对涂膜硅片进行曝光,然后在110℃下烘烤100秒,最后在23℃下2.38%的TMAH水溶液显影60秒。通过上述方法确定形成线宽2μm的图案所需的最小曝光。从获得的最小曝光值,根据以下标准评估灵敏度:○-100mJ/cm2以下,X-200mJ/cm2以上。
(2)解像性评价
使用用于形成2μm线宽图案的掩模,除了以100mJ/cm2的曝光量进行曝光以外,以与感度评价相同的方式进行涂膜、曝光和显影。SEM观察显影后的涂膜,并根据以下标准评价分辨率:○-可以形成2μm的图案,X-不能形成2μm的图案。
表3
由表3可知,本发明的光产酸剂A、具有酸不稳定基团的树脂组分B,具有与芳基结合的芳族羧酸化合物C以及碱(三乙胺)和溶剂(PGMEA),混合形成的抗蚀剂组合物可以形成感光度和分辨率优异的图案。从实施例25、对比例3和4可以看出,即使组合物包含具有羧基的化合物,当该化合物不具有与芳族基团键合的羧基时,组合物的分辨率也不能满足要求。
以上所述仅为本发明的优选实施例而已,并不用于限制本发明,对于本领域的技术人员来说,本发明可以有各种更改和变化。凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (13)
1.一种酰亚胺磺酸酯光酸,其特征在于,所述酰亚胺磺酸酯光酸具有以下结构:
其中,
R1选自C1-C20的直链或支链的烷基或氟代烷基、C3-C20的环烷基或氟代环烷基、C6-C18的取代或未取代的芳基、樟脑基、樟脑醌基或叠氮萘酮基团;
R2与R2’可相同,也可不同,各自独立地选自下列基团:氢,卤素,C1-C20的直链状或支链状的烷基,C3-C20的环烷基,C2-C20的直链状或支链状的链烯基和环烯基,C2-C20的直链状或支链状的炔基,C1-C20的直链状或支链状的烷氧基,C1-C20的直链状或支链状的烷硫基,C1-C20的直链状或支链状的卤代烷基,C1-C20的直链状或支链状的羟基取代烷基,C2-C20的直链状或支链状的羟基烷氧基取代烷基,被C6-C10的芳基或芳氧基取代的C1-C20烷基,被1个以上的-O-、-S-、-O-CO-或-CO-O-中断的C2-C20的直链状或支链状的烷基或烷氧基,取代或未取代的C6-C10芳基,C6-C20的芳基硫基,含有N、O和/或S的C2-C20的杂环基团;或者
R2,R2’彼此相连成环;
R3和R4各自独立地选自下列基团:氢;硝基;氰基;羟基;卤素;C1-C20的直链状或支链状的烷基,链上的氢原子可以被卤原子或羟基、C2-C20的直链状或支链状的烯基、C2-C20的直链状或支链状的炔基、C1-C20的直链状或支链状的烷基,或C1-C20的直链状或支链状的烷基中的-CH2-被-O-、-S-、-CO-、-COO-或-OCO-取代;C3-C30的环烷基,其中的氢原子可以被卤素、C1-C20的直链或支链烷基、被1个以上的-O-、-S-、-OCO-或-COO-中断的C2-C20的直链状或支链状的烷基所取代;桥环烷基,所述桥环烷基中的氢原子可以被卤素、C1-C20的直链或支链烷基、被1个以上的-O-、-S-、-OCO-或-COO-中断的C2-C20的直链状或支链状的烷基所取代;C6-C30芳基,C6-C30芳基的苯环上至少一个氢原子被C1-C20的直链状或支链状的烷基、C1-C20的直链状或支链状的烷氧基、C6-C20的芳基取代的C1-C20烷氧基、C1-C20的直链状或支链状的烷硫基、C1-C20的酰基、C1-C20的酰氧基或C1-C20的氧酰基取代;含有N、O和/或S的C2-C20的杂环基团,其中的氢原子可以被卤原子或羟基、C2-C20的直链状或支链状的烯基、C2-C20的直链状或支链状的炔基、C1-C20的直链状或支链状的烷基取代,其中,C1-C20的直链状或支链状的烷基中的-CH2-被-O-、-S-、-CO-、/>-COO-或-OCO-取代;R3和R4可以连接成环。
2.根据权利要求1所述的酰亚胺磺酸酯类光产酸剂,其特征在于:R1表示C1-C10的直链状或支链状的烷基、C3-C10的环烷基或氟代环烷基、C1-C8的直链状或支链状的氟代烷基、C3-C10的氟代苯基、被C1-C4的烷基或氟代烷基取代的苯基、樟脑基、樟脑醌基或叠氮萘酮基团。
3.根据权利要求1所述的酰亚胺磺酸酯类光产酸剂,其特征在于,R2与R2’可相同,也可不同,各自独立地选自下列基团:氢,C1-C12的直链状或支链状的烷基,C3-C12的环烷基,C2-C12的直链状或支链状的链烯基,C2-C12的直链状或支链状的炔基,C1-C12的直链状或支链状的烷氧基,C1-C12的直链状或支链状的烷硫基,被1个以上的-O-、-S-、-O-CO-或-CO-O-中断的C2-C12的直链状或支链状的烷基或烷氧基,未取代或被C1-C4的烷基或烷氧基取代的C6-C10芳基,C6-C10芳基硫基,含有N、O和/或S的C4-C10的杂环基团如噻吩基,N-吡咯基,吡啶基,吲哚基等;或者R2与R2’彼此相连以形成五元环或六元环。
4.根据权利要求1所述的酰亚胺磺酸酯类光产酸剂,其特征在于,R3和R4选自下列基团:氢,硝基,氰基,羟基,卤素,C1-C20的直链状或支链状的烷基,链上的氢原子可以被卤原子或羟基、C2-C20的直链状或支链状的烯基、C2-C20的直链状或支链状的炔基、C1-C20的直链状或支链状的烷基,或C1-C20的直链状或支链状的烷基中的-CH2-被-O-、-S-、-CO-、-COO-或-OCO-取代;C3-C30的环烷基,其中的氢原子可以被卤素、C1-C20的直链或支链烷基、被1个以上的-O-、-S-、-OCO-或-COO-中断的C2-C20的直链状或支链状的烷基所取代;桥环烷基,所述桥环烷基中的氢原子可以被卤素、C1-C20的直链或支链烷基、被1个以上的-O-、-S-、-OCO-或-COO-中断的C2-C20的直链状或支链状的烷基所取代;C6-C30芳基,C6-C30芳基的苯基中至少一个氢原子被C1-C20的直链状或支链状的烷基、C1-C20的直链状或支链状的烷氧基、C6-C20的芳基取代的C1-C20烷氧基、C1-C20的直链状或支链状的烷硫基、C1-C20的酰基、C1-C20的酰氧基或C1-C20的氧酰基取代;含有N、O和/或S的C2-C20的杂环基团,其中的氢原子可以被卤原子或羟基,C2-C20的直链状或支链状的烯基、C2-C20的直链状或支链状的炔基、C1-C20的直链状或支链状的烷基取代,其中,C1-C20的直链状或支链状的烷基中的-CH2-被-O-、-S-、-CO-、/>-COO-或-OCO-取代;R3和R4可以连接成环;R3和R4可相同,也可不同。
5.权利要求1-4中任一项所述的酰亚胺磺酸酯类光产酸剂的制备方法,通式(1)、(2)分别包括下列步骤:
1)4-X苯酐醇解形成酯化物(I);
2)上述酯化物与硼酸频那醇酯生成4-硼酸频那醇酯化合物(II);
3)6-X茚并噻吩/2-X茚并噻吩在碱性条件下与R2X/R2‘X反应制得4,4’-R2,R2‘茚并噻吩化合物,其中,R2与R2’相同或不同;
4)上述茚并噻吩化合物与酰卤R3X/R4X反应生成2-R3/3-R4、6/7-R3化合物;
5)步骤4)产物和步骤2)产物进行C-C偶联;
6)步骤5)产物水解并脱水成酐;
7)步骤6)产物与羟胺发生肟化反应,生成肟化合物;
8)步骤7)肟化合物与酰化试剂即R1-SO2X或(R1SO2)2O在碱性条件下于惰性溶剂中发生酯化反应,生成酰亚胺磺酸酯类光产酸剂,其中,X为卤素;
反应流程如下所示:
其中,X为卤素;Y为C1-C12的直链或支链的烷烃、环烷烃或C6-C12芳烃;R1、R2、R2’、R3及R4的定义如前文所述。
6.一种酸产生方法,其特征在于:对权利要求1-4中任一项所述的酰亚胺磺酸酯类光产酸剂照射活性能量射线,所述活性能量射线为近紫外光区域、可见光区域的波长在300-450nm之间的活性能量射线,特别优选的是波长365nm(i线)-436nm(g线)的活性能量射线。
7.权利要求1-4中任一项所述的酰亚胺磺酸酯类光产酸剂在抗蚀膜、液态抗蚀剂、负型抗蚀剂、正型抗蚀剂、MEMS用抗蚀剂、立体光刻和微立体光刻用材料中的应用。
8.一种抗蚀剂组合物,包括权利要求1-4中任一项所述的酰亚胺磺酸酯类光产酸剂,所述光产酸剂的含量为组合物中树脂成分的0.5-5%(w/w)。
9.根据权利要求8所述的抗蚀剂组合物,其特征在于:所述组合物是正型抗蚀剂组合物,还含有经由酸的作用而增大对碱显影液溶解性的树脂成分(B1);所述组合物为负型抗蚀剂组成物,还含有在酸的作用下发生交联而不溶于有机系显影液的树脂-交联剂成分(B2),即含酚羟基的树脂(B2-1)和交联剂(B2-2)。
10.根据权利要求8中所述的抗蚀剂组合物,其特征在于:组合物中还包含芳香族羧酸化合物(C),即至少一个羧酸基团键合到芳香族基团上。
11.根据权利要求8中所述的抗蚀剂组合物,其特征在于:组合物中还包含碱(D),所述碱的含量为组合物中树脂成分的0-1.0%(w/w)。
12.权利要求8-11中任一项所述的抗蚀剂组合物在电子组件的保护膜、层间绝缘材料、图型转移材料的制备中的应用。
13.一种电子组件,包含由权利要求8-11中任一项所述的抗蚀剂组合物制备而成的保护膜、层间绝缘材料或图型转移材料。
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