CN111381447A - 感光树脂组合物、层叠体和图案形成方法 - Google Patents
感光树脂组合物、层叠体和图案形成方法 Download PDFInfo
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- CN111381447A CN111381447A CN201911375720.5A CN201911375720A CN111381447A CN 111381447 A CN111381447 A CN 111381447A CN 201911375720 A CN201911375720 A CN 201911375720A CN 111381447 A CN111381447 A CN 111381447A
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G77/50—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
- C08G77/52—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages containing aromatic rings
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- 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/54—Nitrogen-containing linkages
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/14—Peroxides
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- 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
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Abstract
本发明涉及感光树脂组合物、层叠体和图案形成方法。涂布包含(A)含有机硅骨架的聚合物、(B)光致产酸剂和(C)过氧化物的感光树脂组合物形成感光树脂涂层,其在保持挠性的同时不易发生塑性变形。还提供了使用该组合物的图案形成方法。
Description
相关申请的交叉引用
本非临时申请在美国法典第35卷第119节(a)款下要求2018年12月28日于日本提交的第2018-247071号专利申请的优先权,所述专利申请的全部内容通过引用并入本文。
技术领域
本发明涉及感光树脂组合物、层叠体和图案形成方法。
背景技术
在现有技术中,用于半导体芯片的感光保护膜和用于多层印刷电路板的感光绝缘膜由感光聚酰亚胺组合物、感光环氧树脂组合物、感光有机硅组合物等形成。作为用于保护此类基材和电路的感光材料,专利文献1公开了具有改善的挠性的感光有机硅组合物。该感光有机硅组合物可在低温下固化并形成涂层,该涂层在耐湿粘附性和其他性能方面是完全可靠的,但对化学品例如具有高溶解力的光刻胶剥离剂、典型地为N-甲基-2-吡咯烷酮(NMP)的抵抗力较弱。
为了解决该问题,专利文献2提出了基于含硅亚苯基骨架的有机硅聚合物的感光有机硅组合物。该组合物提高了对光刻胶剥离剂等的耐化学性,但是仍然存在以下问题:即固化涂层在热循环测试(重复在-25℃下保持10分钟并在125℃下保持10分钟的测试的1000个循环)中从基材剥离或开裂。需要进一步改善此类树脂组合物的可靠性。
当将有机硅组合物用作半导体芯片上的保护膜或介电膜以及用作光学构件之类的部件时,要求它们不仅具有可靠性,而且还应具有在释放施加的力后恢复到原始形状的能力。为此,需要具有低百分比塑性变形的材料。然而,因为掺入到聚合物中的有机硅骨架呈螺旋结构,所以有机硅聚合物易于变形。添加填料或有机过氧化物固化剂成功地增加了强度,但是不能保持有机硅骨架的挠性。需要在保持挠性的同时具有低百分比塑性变形的材料。
引用列表
专利文献1:JP-A 2002-088158(USP 6590010,EP 1186624)
专利文献2:JP-A 2012-001668(USP 8715905,EP 2397508)
发明内容
本发明的一个目的是提供感光树脂组合物,使用该组合物获得的层叠体以及使用该组合物的图案形成方法,所述感光树脂组合物包含含有机硅骨架的聚合物,能够形成感光树脂涂层,所述感光树脂涂层在保持挠性的同时不易塑性变形。
发明人发现,当将具有夺氢能力的过氧化物与分子中不含乙烯基的含有机硅骨架的聚合物组合使用时,在含有机硅骨架的聚合物上的侧链烃之间形成交联,由此硅氧烷骨架被交联在一起,阻止它们的螺旋结构进一步延伸。因此,获得在保持有机硅挠性的同时不易塑性变形的感光树脂组合物。
在一方面,本发明提供感光树脂组合物,其包含:(A)含有机硅骨架的聚合物、(B)光致产酸剂、和(C)过氧化物。
在一个优选的实施方案中,含有机硅骨架的聚合物(A)包含具有式(a1)至(a4)和(b1)至(b4)的重复单元。
其中,R1至R4分别独立地为C1-C8一价烃基,m为1至600的整数,a1至a4和b1至b4为以下范围内的数:0≤a1<1、0≤a2<1,0≤a3<1、0≤a4<1、0≤b1<1、0≤b2<1、0≤b3<1、0≤b4<1、0<a1+a2+a3+a4<1、0<b1+b2+b3+b4<1、和a1+a2+a3+a4+b1+b2+b3+b4=1,X1为具有下式(X1)的二价基团,X2为具有下式(X2)的二价基团,X3为具有下式(X3)的二价基团,X4为具有下式(X4)的二价基团。
其中,Z1为单键、亚甲基、丙烷-2,2-二基、1,1,1,3,3,3-六氟丙烷-2,2-二基或芴-9,9-二基,R11和R12各自独立地为氢或甲基,R13和R14各自独立地为C1-C4烷基或C1-C4烷氧基,p1和p2各自独立地为0至7的整数,并且q1和q2各自独立地为0至2的整数。
其中,Z2为单键、亚甲基、丙烷-2,2-二基、1,1,1,3,3,3-六氟丙烷-2,2-二基或芴-9,9-二基,R21和R22各自独立地为氢或甲基,R23和R24各自独立地为C1-C4烷基或烷氧基,r1和r2各自独立地为0至7的整数,并且s1和s2各自独立地为0至2的整数。
其中,R31和R32各自独立地为氢或甲基,t1和t2各自独立地为0至7的整数。
其中,R41和R42各自独立地为氢或甲基,R43和R44各自独立地为C1-C8一价烃基,u1和u2各自独立地为0至7的整数,并且v为0至600的整数。
优选地,过氧化物(C)为选自过氧缩酮(peroxyketal)、氢过氧化物、二烷基过氧化物、二酰基过氧化物、过氧酯和过氧化二碳酸酯化合物的有机过氧化物。还优选地,过氧化物(C)的含量为0.1至50重量份,每100重量份的含有机硅骨架的聚合物(A)。
所述组合物可进一步包含(D)交联剂、(E)溶剂和/或(F)淬灭剂。
在另一方面,本发明提供层叠体,其包含具有沟槽和/或孔的基材和在其上由以上限定的感光树脂组合物形成的感光树脂涂层,所述沟槽和/或孔的开口宽度为10至100μm且深度为10至120μm。
在又一方面,本发明提供图案形成方法,其包括以下步骤:
(i)使用以上限定的感光树脂组合物在基材上形成感光树脂涂层,
(ii)将感光树脂涂层曝光于辐照,
(iii)将曝光树脂涂层在显影剂中显影,以及任选地
(iv)将由显影步骤(iii)所得到的图案化树脂涂层在100至250℃的温度下进行后固化。
典型地,基材具有开口宽度为10至100μm,深度为10至120μm的沟槽和/或孔。
发明的有益效果
感光树脂组合物容易形成涂层。感光树脂涂层具有改善的性能,所述性能包括耐光性、微加工性、可靠性(在粘附性和抗裂性方面)、分辨率和挠性等。
具体实施方式
本文中所使用的标记(Cn-Cm)表示每个基团含有n至m个碳原子的基团。
感光树脂组合物
本发明的一个实施方案是感光树脂组合物,其包含:(A)含有机硅骨架的聚合物、(B)光致产酸剂和(C)过氧化物。
(A)含有机硅骨架的聚合物
组分(A)为含有机硅骨架的聚合物。优选地,含有机硅骨架的聚合物(A)包含具有式(a1)至(a4)和(b1)至(b4)的重复单元。为简单起见,所述重复单元也分别称为重复单元(a1)至(a4)和(b1)至(b4)。
在式(a1)至(a4)中,R1至R4各自独立地为C1-C8一价烃基,m为1至600的整数。当m为至少2的整数时,基团R3可以相同或不同,并且基团R4可以相同或不同。在重复单元(a1)至(a4)中,在包括至少两个硅氧烷单元时,该硅氧烷单元可以全部相同,或者可以包括至少两个不同的硅氧烷单元。当包括至少2种不同的硅氧烷单元时(即,m为至少2的整数),该硅氧烷单元可以无规或交替地键合,或可以包括多个嵌段,所述多个嵌段的每个由相同的硅氧烷单元组成。
一价烃基可以是直链、支链或环状。实例包括烷基,例如甲基、乙基、丙基、己基、环己基及它们的结构异构体,以及芳基,例如苯基。其中,由于反应物的容易获得性,优选甲基和苯基。
在式(a1)至(a4)中,m为1至600的整数,优选为1至400的整数,更优选为1至200的整数。
在式(a1)和(b1)中,X1为具有式(X1)的二价基团。
在式(X1)中,Z1为单键、亚甲基、丙烷-2,2-二基、1,1,1,3,3,3-六氟丙烷-2,2-二基或芴-9,9-二基。R11和R12各自独立地为氢或甲基,R13和R14各自独立地为C1-C4烷基或C1-C4烷氧基,p1和p2各自独立地为0至7的整数,并且q1和q2各自独立地为0至2的整数。
烷基可以是直链、支链或环状,其实例包括甲基、乙基、丙基、丁基及它们的结构异构体。烷氧基可以是直链、支链或环状,其实例包括甲氧基、乙氧基、丙氧基、丁氧基和结构异构体。
在式(a2)和(b2)中,X2为具有式(X2)的二价基团。
在式(X2)中,Z2为单键、亚甲基、丙烷-2,2-二基、1,1,1,3,3,3-六氟丙烷-2,2-二基或芴-9,9-二基。R21和R22各自独立地为氢或甲基,R23和R24各自独立地为C1-C4烷基或C1-C4烷氧基,r1和r2各自独立地为0至7的整数,并且s1和s2各自独立地为0、1或2的整数。烷基或烷氧基的实例如上所例示。
在式(a3)和(b3)中,X3为具有式(X3)的二价基团。
在式(X3)中,R31和R32各自独立地为氢或甲基,t1和t2各自独立地为0至7的整数。
在式(a4)和(b4)中,X4为具有式(X4)的二价基团。
在式(X4)中,R41和R42各自独立地为氢或甲基。R43和R44各自独立地为C1-C8一价烃基,u1和u2各自独立地为0至7的整数。下标v为0至600,优选为0至400,更优选为0至200的整数。一价烃基的实例如以上对于R1至R4所例示。在式(X4)中,当v为至少2的整数时,具有下标v的硅氧烷单元可以无规或交替地键合,或可以包括多个嵌段,所述多个嵌段的每个由相同的硅氧烷单元组成。
含有机硅骨架的聚合物(A)在分子中具有诸如环氧基和羟基这样的交联基团或对交联反应敏感的反应性位点。
含有机硅骨架的聚合物(A)的重均分子量(Mw)优选为3,000至500,000,更优选为5,000至200,000。注意:在整个公开中,Mw通过凝胶渗透色谱法(GPC)相对于聚苯乙烯标样使用四氢呋喃作为洗脱剂而进行测量。
下标a1至a4和b1至b4为以下范围内的数:0≤a1<1、0≤a2<1、0≤a3<1、0≤a4<1、0≤b1<1、0≤b2<1、0≤b3<1、0≤b4<1、0<a1+a2+a3+a4<1、0<b1+b2+b3+b4<1、和a1+a2+a3+a4+b1+b2+b3+b4=1,
优选为以下范围:0≤a1≤0.8、0≤a2≤0.8、0≤a3≤0.8、0≤a4≤0.8、0≤b1≤0.95、0≤b2≤0.95、0≤b3≤0.95、0≤b4≤0.95、0.05≤a1+a2+a3+a4≤0.8、0.2≤b1+b2+b3+b4≤0.95、和a1+a2+a3+a4+b1+b2+b3+b4=1,
更优选为以下范围:0≤a1≤0.7、0≤a2≤0.7、0≤a3≤0.7、0≤a4≤0.7、0≤b1≤0.9、0≤b2≤0.9、0≤b3≤0.9、0≤b4≤0.9、0.1≤a1+a2+a3+a4≤0.7、0.3≤b1+b2+b3+b4≤0.9、和a1+a2+a3+a4+b1+b2+b3+b4=1。
在聚合物中,重复单元可以无规或嵌段键合(以形成嵌段共聚物)。在每个重复单元中,硅氧烷单元可以无规键合,或者可以包括多个嵌段,所述多个嵌段的每个由相同类型的硅氧烷单元组成。该聚合物的有机硅(硅氧烷单元)含量优选为30至80重量%。
含有机硅骨架的聚合物(A)在感光树脂组合物中发挥充分的成膜功能。由该组合物获得的感光树脂涂层具有改善的对基材等的粘附性、图案形成能力、抗裂性和耐热性。
含有机硅骨架的聚合物可以单独使用或以两种或以上混合使用来作为组分(A)。
含有机硅骨架的聚合物的制备
含有机硅骨架的聚合物可通过将以下所示的式(1)化合物、式(2)化合物和至少一种选自式(3)化合物、式(4)化合物、式(5)化合物和式(6)化合物的化合物在金属催化剂存在下进行加成聚合而制备。这些化合物也分别称为化合物(1)至(6)。
其中,R1至R4和m如以上所限定。
其中,R11至R14、R21至R24、R31、R32、R41至R44、Z1、Z2、p1、p2、q1、q2、r1、r2、s1、s2、t1、t2、u1、u2和v如上所限定。
在本文中使用的金属催化剂的实例包括铂族金属单质,例如铂(包括铂黑)、铑和钯;氯化铂,氯铂酸和氯铂酸盐,例如H2PtCl4·xH2O、H2PtCl6·xH2O、NaHPtCl6·xH2O、KHPtCl6·xH2O、Na2PtCl6·xH2O、K2PtCl4·xH2O、PtCl4·xH2O、PtCl2和Na2HPtCl4·xH2O,其中x为0至6的整数,更优选为0或6;如USP 3,220,972中所述的醇改性氯铂酸;如USP 3,159,601,USP 3,159,662和USP 3,775,452中所述的氯铂酸-烯烃配合物;在氧化铝、二氧化硅和碳的载体上包含铂族金属如铂黑和钯的负载型催化剂;铑-烯烃配合物;氯三(三苯基膦)合铑(熟知为威尔金森催化剂);以及氯化铂、氯铂酸和氯铂酸酯与含乙烯基的硅氧烷、特别是含乙烯基的环硅氧烷的配合物。
催化剂以催化量使用,基于化合物(1)至(6)的总重量,其优选为0.001至0.1重量%、更优选为0.01至0.1重量%的铂族金属。
在聚合反应中,根据需要,可使用溶剂。合适的溶剂为烃溶剂,例如甲苯和二甲苯。关于聚合条件,聚合温度优选在40至150℃、更优选60至120℃内选择,以使催化剂不会失活并且在短时间内完成聚合。尽管聚合时间随单体的类型和量而改变,但是为了防止水分进入聚合体系,聚合反应优选在约0.5至约100小时,更优选在约0.5至约30小时内完成。聚合反应完成后,将溶剂(如果有的话)蒸馏掉,得到所需的聚合物。
反应步骤没有特别限制。优选的步骤为首先加热选自化合物(3)至(6)的一种或多种化合物,向其中加入金属催化剂,然后在0.1至5小时内逐滴添加化合物(1)和(2)。
优选以使化合物(1)和(2)上的氢硅烷基的总量与化合物(3)至(6)上的烯基的总量的摩尔比为0.67/1至1.67/1、更优选为0.83/1至1.25/1的量来组合反应物。聚合物的Mw可使用分子量控制剂例如单烯丙基化合物(例如,邻烯丙基苯酚)、单氢硅烷(例如,三乙基氢硅烷)或单氢硅氧烷来控制。
(B)光致产酸剂
作为组分(B)的光致产酸剂(PAG)通常为:在曝光、优选波长为190至500nm的光时分解而产生酸的化合物。由于本发明的感光树脂组合物与PAG高度相容,因此PAG可以选自广范围的此类化合物。
PAG(B)用作固化催化剂。合适的PAG包括鎓盐、重氮甲烷衍生物、乙二肟衍生物、β-酮砜衍生物、二砜衍生物、硝基苯甲基磺酸酯衍生物、磺酸酯衍生物、酰亚胺磺酸酯(imidoyl sulfonate)衍生物、肟磺酸酯衍生物、亚氨基磺酸酯衍生物和三嗪衍生物。
示例性的鎓盐包括具有式(B1)的硫鎓盐和具有式(B2)的碘鎓盐。
在式(B1)和(B2)中,R101至R105各自独立地为任选取代的C1-C12烷基,任选取代的C6-C12芳基或任选取代的C7-C12芳烷基。A-为非亲核抗衡离子。
烷基可以是直链、支链或环状,且包括例如甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、环丁基、正戊基、环戊基、环己基、降冰片基和金刚烷基。芳基包括苯基、萘基和联苯基。芳烷基包括苯甲基和苯乙基。这些基团上的合适取代基包括氧代,直链、支链或环状C1-C12烷氧基,直链、支链或环状C1-C12烷基,C6-C24芳基,C7-C25芳烷基,C6-C24芳氧基和C6-C24芳硫基。
R101至R105的优选实例包括任选取代的烷基,例如甲基、乙基、丙基、丁基、环己基、降冰片基、金刚烷基和2-氧代环己基;任选取代的芳基,例如苯基、萘基、联苯基、邻、间或对甲氧基苯基、乙氧基苯基、间或对叔丁氧基苯基、2-、3-或4-甲基苯基、乙基苯基、4-叔丁基苯基、4-丁基苯基、二甲基苯基、三联苯基、联苯基、氧苯基和联苯基苯硫基(biphenylylthiophenyl);以及任选取代的芳烷基,例如苯甲基和苯乙基。其中,更优选任选取代的芳基和任选取代的芳烷基。
由A-表示的非亲核抗衡离子的实例包括卤离子,例如氯根离子和溴根离子;氟烷磺酸根离子,例如三氟甲磺酸根、1,1,1三氟乙烷磺酸根和九氟丁烷磺酸根;芳基磺酸根离子,例如甲苯磺酸根、苯磺酸根、4-氟苯磺酸根和1,2,3,4,5-五氟苯磺酸根;烷磺酸根离子,例如甲磺酸根和丁磺酸根;氟烷磺酰亚胺离子,例如三氟甲磺酰亚胺;氟烷磺酰基甲基离子,例如三(三氟甲烷磺酰基)甲基;和硼酸根离子,例如四苯基硼酸根和四(五氟苯基)硼酸根。
示例性重氮甲烷衍生物包括具有式(B3)的化合物。
在式(B3)中,R111和R112各自独立地为C1-C12烷基或卤代烷基、任选取代的C6-C12芳基或C7-C12芳烷基。
烷基可以是直链、支链或环状,其实例为如上文对于R101至R105所举例说明的。卤代烷基的实例包括三氟甲基、1,1,1-三氟乙基、1,1,1-三氯乙基和九氟丁基。任选取代的芳基的实例包括苯基;烷氧基苯基,例如2-、3-或4-甲氧基苯基、2-、3-或4-乙氧基苯基、3-或4-叔丁氧基苯基;烷基苯基,例如2-、3-或4-甲基苯基、乙基苯基、4-叔丁基苯基、4-丁基苯基和二甲基苯基;以及卤代芳基,例如氟苯基、氯苯基和1,2,3,4,5-五氟苯基。芳烷基的实例包括苯甲基和苯乙基。
示例性乙二肟衍生物包括具有式(B4)的化合物。
在式(B4)中,R121至R124各自独立地为C1-C12烷基或卤代烷基,任选取代的C6-C12芳基或C7-C12芳烷基。R123和R124可键合在一起与它们所连接的碳原子形成环。在成环的情况下,R123与R124键合以形成C1-C12的直链或支链亚烷基。
烷基、卤代烷基、任选取代的芳基和芳烷基的实例如上对于R111和R112所例示。直链或支链亚烷基的实例包括亚甲基、亚乙基、亚丙基、亚丁基和亚己基。
鎓盐的实例包括二苯基碘鎓三氟甲磺酸盐、
(对叔丁氧基苯基)苯基碘鎓三氟甲磺酸盐、
二苯基碘鎓对甲苯磺酸盐、
(对叔丁氧基苯基)苯基碘鎓对甲苯磺酸盐、
三苯基硫鎓三氟甲磺酸盐、
(对叔丁氧基苯基)二苯基硫鎓三氟甲磺酸盐、
二(对叔丁氧基苯基)苯基硫鎓三氟甲磺酸盐、
三(对叔丁氧基苯基)硫鎓三氟甲磺酸盐、
三苯基硫鎓对甲苯磺酸盐、
(对叔丁氧基苯基)二苯基硫鎓对甲苯磺酸、
二(对叔丁氧基苯基)苯基硫鎓对甲苯磺酸盐、
三(对叔丁氧基苯基)硫鎓对甲苯磺酸盐、
三苯基硫鎓九氟丁烷磺酸盐、三苯基硫鎓丁烷磺酸盐、
三甲基硫鎓三氟甲烷磺酸盐、三甲基硫鎓对甲苯磺酸盐、
环己基甲基(2-氧代环己基)硫鎓三氟甲烷磺酸盐、
环己基甲基(2-氧代环己基)硫鎓对甲苯磺酸盐、
二甲基苯基硫鎓三氟甲烷磺酸盐、
二甲基苯基硫鎓对甲苯磺酸盐、
二环己基苯基硫鎓三氟甲烷磺酸盐、
二环己基苯基硫鎓对甲苯磺酸盐、
双(4-叔丁基苯基)碘鎓六氟磷酸盐、
二苯基(4-噻吩氧基苯基)硫鎓六氟锑酸盐、
[4-(4-联苯基硫基)苯基]-4-联苯基苯基硫鎓三(三氟甲烷磺酰基)甲基化物、
三苯基硫鎓四(氟苯基)硼酸盐、
三[4-(4-乙酰基苯基)硫代苯基]硫鎓四(氟苯基)硼酸盐、
三苯基硫鎓四(五氟苯基)硼酸盐、和
三[4-(4-乙酰基苯基)硫代苯基]硫鎓四(五氟苯基)硼酸盐。
重氮甲烷衍生物的实例包括
双(苯磺酰基)重氮甲烷、双(对甲苯磺酰基)重氮甲烷、
双(二甲苯磺酰基)重氮甲烷、双(环己磺酰基)重氮甲烷、
双(环戊基磺酰基)重氮甲烷、双(正丁基磺酰基)重氮甲烷、
双(异丁基磺酰基)重氮甲烷、双(仲丁基磺酰基)重氮甲烷、
双(正丙基磺酰基)重氮甲烷、双(异丙基磺酰基)重氮甲烷、
双(叔丁基磺酰基)重氮甲烷、双(正戊基磺酰基)重氮甲烷、
双(异戊基磺酰基)重氮甲烷、双(仲戊基磺酰基)重氮甲烷、
双(叔戊基磺酰基)重氮甲烷、
1-环己基磺酰基-1-(叔丁基磺酰基)重氮甲烷、
1-环己基磺酰基-1-(叔戊基磺酰基)重氮甲烷、和
1-叔戊基磺酰基-1-(叔丁基磺酰基)重氮甲烷。
乙二肟衍生物的实例包括
双-O-(对甲苯磺酰基)-α-二甲基乙二肟、
双-O-(对甲苯磺酰基)-α-二苯基乙二肟、
双-O-(对甲苯磺酰基)-α-二环己基乙二肟、
双-O-(对甲苯磺酰基)-2,3-戊二酮乙肟、
双-O-(对甲苯磺酰基)-2-甲基-3,4-戊二酮乙肟、
双-O-(正丁烷磺酰基)-α-二甲基乙二肟、
双-O-(正丁烷磺酰基)-α-二苯基乙二肟、
双-O-(正丁烷磺酰基)-α-二环己基乙二肟、
双-O-(正丁烷磺酰基)-2,3-戊二酮乙二肟、
双-O-(正丁烷磺酰基)-2-甲基-3,4-戊二酮乙二肟、
双-O-(甲烷磺酰基)-α-二甲基乙二肟、
双-O-(三氟甲烷磺酰基)-α-二甲基乙二肟、
双-O-(1,1,1-三氟乙烷磺酰基)-α-二甲基乙二肟、
双-O-(叔丁烷磺酰基)-α-二甲基乙二肟、
双-O-(全氟辛烷磺酰基)-α-二甲基乙二肟、
双-O-(环己烷磺酰基)-α-二甲基乙二肟、
双-O-(苯磺酰基)-α-二甲基乙二肟、
双-O-(对氟苯磺酰基)-α-二甲基乙二肟、
双-O-(对叔丁基苯磺酰基)-α-二甲基乙二肟、
双-O-(二甲苯磺酰基)-α-二甲基乙二肟、和
双-O-(樟脑磺酰基)-α-二甲基乙二肟。
β-酮砜衍生物的实例包括2-环己基羰基-2-(对甲苯磺酰基)丙烷、和2-异丙基羰基-2-(对甲苯磺酰基)丙烷。
二砜衍生物的实例包括二苯基二砜和二环己基二砜。
硝基苯甲基磺酸酯衍生物的实例包括2,6-二硝基苯甲基对甲苯磺酸酯和2,4-二硝基苯甲基对甲苯磺酸酯。
磺酸酯衍生物的实例包括1,2,3-三(甲烷磺酰氧基)苯、1,2,3-三(三氟甲烷磺酰氧基)苯和1,2,3-三(对甲苯磺酰氧基)苯。
酰亚胺磺酸酯衍生物的实例包括邻苯二甲酰亚氨基三氟甲磺酸酯(phthalimidoyl triflate)、邻苯二甲酰亚氨基甲苯磺酸酯(phthalimidoyl tosylate)、5-降冰片烯-2,3-二甲酰亚氨基三氟甲磺酸酯(dicarboxyimidoyl triflate)、5-降冰片烯-2,3-二甲酰亚氨基甲苯磺酸酯(dicarboxyimidoyl tosylate)、5-降冰片烯-2,3-二甲酰亚氨基正丁基磺酸酯(dicarboxyimidoyl n-butylsulfonate)、和n-三氟甲基磺酰氧基萘酰亚胺。
典型的肟磺酸酯衍生物为α-(苯锍氧基亚氨基)-4-甲基苯基乙腈。
亚氨基磺酸酯衍生物的实例包括(5-(4-甲基苯基)磺酰氧基亚氨基-5H-噻吩-2-亚基)-(2-甲基苯基)乙腈和(5-(4-(4-甲基苯基磺酰氧基)苯基磺酰氧基亚氨基)-5H-噻吩-2-亚基)-(2-甲基苯基)乙腈。
还可使用的有2-甲基-2-[(4-甲基苯基)磺酰基]-1-[(4-甲基硫代)苯基]-1-丙烷。
作为PAG,优选鎓盐,其中更优选硫鎓盐。
优选地,PAG(B)的用量相对于100重量份的组分(A)为0.05至20重量份、更优选为0.1至5重量份。当PAG的量至少为0.05份时,避免了产生的酸的量太少而不能发生交联反应的风险。当PAG的量为20份以下时,可以防止产酸剂本身增加其光吸收率,并且避免了透明度的任何损失。
(C)过氧化物
组分(C)为过氧化物,其用作聚合物侧链上的反应性基团以外的交联剂。优选的过氧化物为有机过氧化物。合适的有机过氧化物包括过氧缩酮,例如1,1-二(叔丁基过氧基)-3,3,5-三甲基环己烷、正丁基-4,4-二(叔丁基过氧基)丁酸酯、1,1-二(叔戊基过氧基)-3,3,5-三甲基环己烷,氢过氧化物,例如1,1,3,3-四甲基丁基氢过氧化物和叔丁基氢过氧化物,二烷基过氧化物,例如过氧化二枯基、过氧化二叔丁基和2,5-二甲基-2,5-二(叔丁基过氧基)-3-己炔,二酰基过氧化物,例如过氧化二异壬酰、过氧化二月桂酰和过氧化二苯甲酰,烷基过氧酯,例如过氧化新癸酸叔丁酯、过氧化新戊酸叔丁酯、过氧化2-乙基己酸叔丁酯、过氧化苯甲酸叔丁酯、过氧化新癸酸叔戊酯和过氧化乙酸叔戊酯,单过氧碳酸酯,例如叔丁基过氧化碳酸异丙酯和叔戊基过氧化碳酸2-乙基己酯,过氧化二碳酸酯,例如过氧化二碳酸二(2-乙基己酯)、1,6-双(4-叔丁基过氧基羰基氧基)己烷和过氧化二碳酸酯二(4-叔丁基环己酯)和过氧化苯甲酰。其中,优选具有较高分解温度的过氧缩酮、二烷基过氧化物和过氧酯,以易于处理和保存稳定性。在使用前,这些有机过氧化物可以用任何有机溶剂、烃、液体石蜡或惰性固体来稀释。
组分(C)的用量相对于100重量份的组分(A)优选为0.1至50重量份、更优选为1至20重量份。在该范围内的组分(C)的量确保耐热性和粘附性的改善。
(D)交联剂
优选地,感光树脂组合物还包含(D)交联剂。交联剂与组分(A)上的酚羟基或由R13、R14、R23或R24表示的烷氧基进行缩合反应,以由此促进图案形成并提高固化组合物的强度。
优选的交联剂为Mw为150至10,000、更优选为200至3,000的树脂。Mw为至少150的树脂是可光固化的,而Mw为高达10,000的树脂可能不会不利地影响固化组合物的耐热性。
优选地,交联剂选自在分子中具有平均至少两个羟甲基和/或烷氧基甲基的含氮化合物例如三聚氰胺、胍胺、甘脲和脲化合物;用甲醛或甲醛-醇改性的氨基缩合物;分子中具有平均至少两个羟甲基或烷氧基甲基的酚化合物;以及分子中具有平均至少两个环氧基的环氧化合物。
优选的三聚氰胺化合物具有式(D1)。
在式(D1)中,R201至R206各自独立地为羟甲基、C2-C5烷氧基甲基或氢,R201至R206中的至少一个为羟甲基或烷氧基甲基。烷氧基甲基的实例为甲氧基甲基和乙氧基甲基。
合适的具有式(D1)的三聚氰胺化合物包括三甲氧基甲基单羟甲基三聚氰胺、二甲氧基甲基单羟甲基三聚氰胺、三羟甲基三聚氰胺、六羟甲基三聚氰胺、六甲氧基甲基三聚氰胺、和六乙氧基甲基三聚氰胺。
具有式(D1)的三聚氰胺化合物可以根据公知技术用甲醛将三聚氰胺单体改性成羟甲基形式、且任选地用醇将其进一步改性成烷氧基形式来制备。本文中所用的醇优选选自低级醇、特别是1至4个碳原子的醇。
合适的胍胺化合物包括四羟甲基胍胺、四甲氧基甲基胍胺和四甲氧基乙基胍胺。
合适的甘脲化合物包括四羟甲基甘脲和四(甲氧基甲基)甘脲。
合适的脲化合物包括四羟甲基脲、四甲氧基甲基脲、四甲氧基乙基脲、四乙氧基甲基脲、和四丙氧基甲基脲。
用甲醛或甲醛-醇改性的氨基缩合物的实例包括用甲醛或甲醛-醇改性的三聚氰胺缩合物、和用甲醛或甲醛-醇改性的脲缩合物。
改性的三聚氰胺缩合物可通过例如使具有式(D1)的三聚氰胺或其低聚物(例如,二聚体或三聚体)与甲醛进行加成缩聚反应直至达到所需分子量来获得。加成缩聚可以通过任何现有技术公知方法进行。
用甲醛或甲醛-醇改性的脲缩合物的实例包括甲氧基甲基化脲缩合物、乙氧基甲基化脲缩合物、和丙氧基甲基化脲缩合物。
改性的脲缩合物可以例如以公知的方式用甲醛将具有所需分子量的脲缩合物改性成羟甲基形式、及任选地用醇将其进一步改性成烷氧基形式来制备。
分子中具有平均至少两个羟甲基或烷氧基甲基的酚化合物的实例包括(2-羟基-5-甲基)-1,3-苯二甲醇和2,2’,6,6’-四甲氧基甲基双酚A。
分子中具有平均至少两个环氧基的环氧化合物的实例包括双酚环氧树脂,例如双酚A环氧树脂和双酚F环氧树脂、酚醛清漆环氧树脂、例如苯酚酚醛清漆环氧树脂和甲酚酚醛清漆环氧树脂、三酚烷烃环氧树脂、联苯环氧树脂、二环戊二烯改性苯酚酚醛清漆环氧树脂、苯酚芳烷基环氧树脂、联苯芳烷基环氧树脂、含萘环的环氧树脂、缩水甘油酯环氧树脂、环脂族环氧树脂和杂环环氧树脂。
当使用时,组分(D)的添加量相对于100重量份的组分(A)优选为0.5至50重量份,更优选为1至30重量份。至少0.5份的组分(D)确保在曝光时充分固化。只要组分(D)的量为50份以下,组分(A)在树脂组合物中的比例就不会降低,使得固化组合物可以充分发挥其作用。交联剂可以单独使用或混合使用。
(E)溶剂
可以向感光树脂组合物中添加(E)溶剂。本文中使用的溶剂(E)没有特别限制,只要上述组分和其他添加剂可溶于其中。
优选的溶剂为有机溶剂,因为所述组分可有效地溶解。有机溶剂的说明性非限制性实例包括酮,如环己酮、环戊酮和甲基-2-正戊基酮;醇,如3-甲氧基丁醇、3-甲基-3-甲氧基丁醇、1-甲氧基-2-丙醇和1-乙氧基2-丙醇;醚,如丙二醇单甲醚(PGME)、乙二醇单甲醚、丙二醇单乙醚、乙二醇单乙醚、丙二醇二甲醚和二甘醇二甲醚;和酯,如丙二醇单甲醚乙酸酯(PGMEA)、丙二醇单乙醚乙酸酯、乳酸乙酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸叔丁酯、丙酸叔丁酯、丙二醇单叔丁醚乙酸酯和γ-丁内酯。这些溶剂可以单独使用或两种以上组合使用。
在这些溶剂中,优选PAG最易溶于其中的乳酸乙酯、环己酮、环戊酮、PGMEA、γ-丁内酯及其混合物。
当使用溶剂时,从树脂组合物的相容性和粘度的观点考虑,优选溶剂(E)的添加量相对于100重量份的组分(A)和(B)的总重量为50至2,000份,更优选为50至1,000份,尤其为50至100份。
(F)淬灭剂
感光树脂组合物可以进一步含有(F)淬灭剂。本文所使用的淬灭剂优选为当由PAG产生的酸在树脂涂层内扩散时能够抑制扩散速率的化合物。包含淬灭剂改善分辨率、抑制曝光后灵敏度的变化、并减少对基材和环境的依赖性,以及改善曝光宽容度和图案轮廓。
淬灭剂的实例包括伯、仲和叔脂族胺,混合胺,芳香族胺,杂环胺,具有羧基的含氮化合物,具有磺酰基的含氮化合物,具有羟基的含氮化合物,具有羟苯基的含氮化合物,醇性的含氮化合物,酰胺衍生物和酰亚胺衍生物。
合适的伯脂族胺的实例包括氨、甲胺、乙胺、正丙胺、异丙胺、正丁胺、异丁胺、仲丁胺、叔丁胺、戊胺、叔戊胺、环戊胺、己胺、环己胺、庚胺、辛胺、壬胺、癸胺、十二烷基胺、鲸蜡胺、亚甲基二胺、乙二胺和四亚乙基五胺。合适的仲脂族胺的实例包括二甲胺、二乙胺、二正丙胺、二异丙胺、二正丁胺、二异丁胺、二仲丁胺、二戊胺、二环戊胺、二己胺、二环己胺、二庚胺、二辛胺、二壬胺、二癸胺、双十二烷基胺、二鲸蜡胺、N,N-二甲基亚甲基二胺、N,N-二甲基乙二胺和N,N-二甲基四亚乙基五胺。合适的叔脂族胺的实例包括三甲胺、三乙胺、三正丙胺、三异丙胺、三正丁胺、三异丁胺、三仲丁胺、三戊胺、三环戊胺、三己胺、三环己胺、三庚胺、三辛胺、三壬胺、三癸胺、三月桂胺、三鲸蜡胺、N,N,N',N'-四甲基亚甲基二胺,N,N,N',N'-四甲基乙二胺和N,N,N',N'-四甲基四亚乙基五胺。
合适的混合胺的实例包括二甲基乙胺、甲基乙基丙胺、苄胺、苯乙胺和苄基二甲基胺。
合适的芳香族和杂环胺的实例包括苯胺衍生物(例如苯胺、N-甲基苯胺、N-乙基苯胺、N-丙基苯胺、N,N-二甲基苯胺、2-甲基苯胺、3-甲基苯胺、4-甲基苯胺、乙基苯胺、丙基苯胺、三甲基苯胺、2-硝基苯胺、3-硝基苯胺、4-硝基苯胺、2,4-二硝基苯胺、2,6-二硝基苯胺、3,5-二硝基苯胺和N,N-二甲基甲苯胺)、二苯基(对甲苯基)胺、甲基二苯胺、三苯胺、苯二胺、萘胺和二氨基萘;和吡咯衍生物(例如吡咯、2H-吡咯、1-甲基吡咯、2,4-二甲基吡咯、2,5-二甲基吡咯和N-甲基吡咯)、噁唑衍生物(例如噁唑和异噁唑)、噻唑衍生物(例如噻唑和异噻唑)、咪唑衍生物(例如咪唑、4-甲基咪唑和4-甲基-2-苯基咪唑)、吡唑衍生物、呋咱衍生物、吡咯啉衍生物(例如吡咯啉和2甲基-1-吡咯啉)、吡咯烷衍生物(例如吡咯烷、N-甲基吡咯烷、吡咯烷酮和N-甲基-2-吡咯烷酮)、咪唑啉衍生物、咪唑烷衍生物、吡啶衍生物(例如吡啶、甲基吡啶、乙基吡啶、丙基吡啶、丁基吡啶、4-(1-丁基戊基)吡啶、二甲基吡啶、三甲基吡啶、三乙基吡啶、苯基吡啶、3-甲基-2-苯基吡啶、4-叔丁基吡啶、二苯基吡啶、苄基吡啶、甲氧基吡啶、丁氧基吡啶、二甲氧基吡啶、1-甲基-2-吡啶、4-吡咯烷基吡啶、1-甲基-4-苯基吡啶、2-(1-乙基丙基)吡啶、氨基吡啶和二甲基氨基吡啶)、哒嗪衍生物、嘧啶衍生物、吡嗪衍生物、吡唑啉衍生物、吡唑烷衍生物、哌啶衍生物、哌嗪衍生物、吗啉衍生物、吲哚衍生物、异吲哚衍生物、1H-吲唑衍生物、二氢吲哚衍生物、喹啉衍生物(例如喹啉和3-氰基喹啉)、异喹啉衍生物、噌啉衍生物、喹唑啉衍生物、喹喔啉衍生物、酞嗪衍生物、嘌呤衍生物、蝶啶衍生物、咔唑衍生物、菲啶衍生物、吖啶衍生物、吩嗪衍生物、1,10-菲咯啉衍生物、腺嘌呤衍生物、腺苷衍生物、鸟嘌呤衍生物、鸟苷衍生物、尿嘧啶衍生物和尿苷衍生物。
合适的具有羧基的含氮化合物的例子包括氨基苯甲酸、吲哚羧酸和氨基酸衍生物(例如烟酸、丙氨酸、精氨酸、天冬氨酸、谷氨酸、甘氨酸、组氨酸、异亮氨酸、甘氨酰亮氨酸、亮氨酸、蛋氨酸、苯丙氨酸、苏氨酸、赖氨酸、3-氨基吡嗪-2-羧酸和甲氧基丙氨酸)。合适的具有磺酰基的含氮化合物的例子包括3-吡啶磺酸和对甲苯磺酸吡啶鎓。合适的具有羟基的含氮化合物、具有羟基苯基的含氮化合物和醇性的含氮化合物的实例包括2-羟基吡啶、氨基甲酚、2,4-喹啉二醇、3-吲哚甲醇水合物、单乙醇胺、二乙醇胺、三乙醇胺、N-乙基二乙醇胺、N,N-二乙基乙醇胺、三异丙醇胺、2,2'-亚氨基二乙醇、2-氨基乙醇、3-氨基-1-丙醇、4-氨基-1-丁醇、4-(2-羟乙基)吗啉、2-(2-羟乙基)吡啶、1-(2-羟乙基)哌嗪、1-[2-(2-羟乙氧基)乙基]哌嗪、哌啶乙醇、1-(2-羟乙基)吡咯烷、1-(2-羟乙基)-2-吡咯烷酮、3-哌啶基-1,2-丙二醇、3-吡咯烷基-1,2-丙二醇、8-羟基久洛尼定、奎宁环-3-醇、3-托品醇、1-甲基-2-吡咯烷乙醇、1-氮丙啶乙醇、N-(2-羟乙基)邻苯二甲酰亚胺和N-(2-羟乙基)异烟酰胺。
合适的酰胺衍生物的实例包括甲酰胺、N-甲基甲酰胺、N,N-二甲基甲酰胺、乙酰胺、N-甲基乙酰胺、N,N-二甲基乙酰胺、丙酰胺和苯甲酰胺。合适的酰亚胺衍生物包括邻苯二甲酰亚胺、琥珀酰亚胺和马来酰亚胺。
式(F1)的化合物也可用作淬灭剂。
(R301)w-N-(R302)3-w (F1)
式(F1)中,w为1、2或3。R301选自下式(F2)至(F4)的取代基,R302为氢或可包含醚键或羟基部分的C1-C20烷基。如果存在两个或三个R301,则两个R301可键合在一起而与其所连接的氮原子形成环。如果存在两个或三个R301,它们可以相同或不同。如果存在两个或2个以上的R302,它们可以相同或不同。
在式(F2)至(F4)中,R303、R305和R308各自独立地为直链或支链C1-C4烷二基。R304和R307各自独立地为氢,可包含至少一个羟基部分、醚键、酯键或内酯环的C1-C20烷基。R306为单键或直链或支链C1-C4烷二基。R309为可含有至少一个羟基部分、醚键、酯键或内酯环的C1-C20烷基。
式(F1)的化合物的实例包括
三[2-(甲氧基甲氧基)乙基]胺、三[2-(2-甲氧基乙氧基)乙基]胺、
三[2-(2-甲氧基乙氧基甲氧基)乙基]胺、三[2-(1-甲氧基乙氧基)乙基]胺、
三[2-(1-乙氧基乙氧基)乙基]胺、三[2-(1-乙氧基丙氧基)乙基]胺、
三[2-{2-(2-羟基乙氧基)乙氧基}乙基]胺、
4,7,13,16,21,24-六氧杂-1,10-二氮杂双环[8.8.8]二十六烷、
4,7,13,18-四氧杂-1,10-二氮杂双环[8.5.5]二十烷、
1,4,10,13-四氧杂-7,16-二氮杂双环十八烷、1-氮杂-12-冠-4,1-氮杂-15-冠-5、
1-氮杂-18-冠-6、三(2-甲酰氧基乙基)胺、三(2-乙酰氧基乙基)胺、
三(2-丙酰氧基乙基)胺、三(2-丁酰氧基乙基)胺、
三(2-异丁酰氧基乙基)胺、三(2-戊酰氧基乙基)胺、
三(2-新戊酰氧基乙基)胺、N,N-双(2-乙酰氧基乙基)-2-(乙酰氧基乙酰氧基)乙胺、
三(2-甲氧基羰基氧基乙基)胺、三(2-叔丁氧基羰基氧基乙基)胺、
三[2-(2-氧代丙氧基)乙基]胺、三[2-(甲氧羰基甲基)氧乙基]胺、
三[2-(叔丁氧基羰基甲氧基)乙基]胺、
三[2-(环己氧基羰基甲氧基)乙基]胺、三(2-甲氧基羰基乙基)胺、
三(2-乙氧基羰基乙基)胺、
N,N-双(2-羟乙基)-2-(甲氧基羰基)乙胺、
N,N-双(2-乙酰氧基乙基)-2-(甲氧基羰基)乙胺、
N,N-双(2-羟乙基)-2-(乙氧基羰基)乙胺、
N,N-双(2-乙酰氧基乙基)-2-(乙氧基羰基)乙胺、
N,N-双(2-羟乙基)-2-(2-甲氧基乙氧基羰基)乙胺、
N,N-双(2-乙酰氧基乙基)-2-(2-甲氧基乙氧基羰基)乙胺、
N,N-双(2-羟乙基)-2-(2-羟乙氧基羰基)乙胺、
N,N-双(2-乙酰氧基乙基)-2-(2-乙酰氧基乙氧基羰基)乙胺、
N,N-双(2-羟乙基)-2-[(甲氧基羰基)甲氧基羰基]乙胺、
N,N-双(2-乙酰氧基乙基)-2-[(甲氧基羰基)甲氧基羰基]乙胺、
N,N-双(2-羟乙基)-2-(2-氧代丙氧基羰基)乙胺、
N,N-双(2-乙酰氧基乙基)-2-(2-氧代丙氧基羰基)乙胺、
N,N-双(2-羟乙基)-2-(四氢糠氧基羰基)乙胺、
N,N-双(2-乙酰氧基乙基)-2-(四氢糠氧基羰基)乙胺、
N,N-双(2-羟乙基)-2-[(2-氧代四氢呋喃-3-基)氧基羰基]乙胺、
N,N-双(2-乙酰氧基乙基)-2-[(2-氧代四氢呋喃-3-基)氧基羰基]乙胺、
N,N-双(2-羟乙基)-2-(4-羟丁氧基羰基)乙胺、
N,N-双(2-甲酰氧基乙基)-2-(4-甲酰氧基丁氧基羰基)乙胺、
N,N-双(2-甲酰氧基乙基)-2-(2-甲酰氧基乙氧基羰基)乙胺、
N,N-双(2-甲氧基乙基)-2-(甲氧基羰基)乙胺、
N-(2-羟乙基)双[2-(甲氧基羰基)乙基]胺、
N-(2-乙酰氧基乙基)双[2-(甲氧基羰基)乙基]胺、
N-(2-羟乙基)双[2-(乙氧基羰基)乙基]胺、
N-(2-乙酰氧基乙基)双[2-(乙氧基羰基)乙基]胺、
N-(3-羟基-1-丙基)双[2-(甲氧基羰基)乙基]胺、
N-(3-乙酰氧基-1-丙基)双[2-(甲氧基羰基)乙基]胺、
N-(2-甲氧基乙基)双[2-(甲氧基羰基)乙基]胺、
N-丁基双[2-(甲氧基羰基)乙基]胺、
N-丁基双[2-(2-甲氧基乙氧基羰基)乙基]胺、
N-甲基双(2-乙酰氧基乙基)胺、
N-乙基双(2-乙酰氧基乙基)胺,N-甲基双(2-新戊酰氧基乙基)胺、
N-乙基双[2-(甲氧基羰基氧基)乙基]胺、
N-乙基双[2-(叔丁氧基羰基氧基)乙基]胺、三(甲氧基羰基甲基)胺、
三(乙氧基羰基甲基)胺、N-丁基双(甲氧基羰基甲基)胺、N-己基双(甲氧基羰基甲基)胺和β-(二乙基氨基)-δ-戊内酯。
组分(F)的配制量相对于100重量份的组分(A)可以为0至3重量份。当使用时,从灵敏度的观点考虑,组分(F)的添加相对于100重量份的组分(A)优选为0.01至2重量份,尤其为0.05至1重量份。组分(F)可以单独使用或混合使用。
其他添加剂
除了上述组分之外,感光树脂组合物还可包含其他添加剂,例如,通常用于改善涂布性能的表面活性剂、和硅烷偶联剂。
优选的表面活性剂为非离子表面活性剂,例如氟化学表面活性剂,如全氟烷基聚氧乙烯乙醇、氟化烷基酯、全氟烷基氧化胺和氟化有机硅氧烷化合物。这些表面活性剂是可商购的。示例性示例包括来自3M的FC-430、来自AGC Seimi Chemical Co.,Ltd.的S-141和S-145、来自Daikin Industries Ltd.的DS-401、DS-4031和DS-451、来自DIC Corp.的F-8151、和来自Shin-Etsu ChemicalCo.,Ltd的X-70-093。优选的表面活性剂为Fluorad FC-430和X-70-093。当使用时,表面活性剂的量相对于100重量份的组分(A)优选为0.01至5重量份。
包含硅烷偶联剂对于增强树脂组合物对被粘物的粘附力是有效的。合适的硅烷偶联剂包括环氧硅烷偶联剂和芳香族氨基硅烷偶联剂。硅烷偶联剂可以单独使用或混合使用。硅烷偶联剂的用量没有特别限制,只要不损害本发明的益处。当使用时,硅烷偶联剂的量优选为树脂组合物重量的0.01至5%。
本发明的感光树脂组合物以任何常规方式制备。例如,其可以通过搅拌和混合上述组分并任选使混合物通过过滤器以除去固体来制备。
感光树脂组合物有利地用作例如半导体器件的保护膜、互连保护膜、覆层膜、阻焊剂和TSV介电膜的膜形成材料,以及三维层叠板中基材之间的粘合剂。
图案形成方案
本发明的另一实施方案是使用上述感光树脂组合物的图案形成方法,该方法包括以下步骤:
(i)使用感光树脂组合物在基材上形成感光树脂涂层,
(ii)将感光树脂涂层曝光于辐照,和
(iii)将曝光树脂涂层在显影剂中显影。
在步骤(i)中,典型地将感光树脂组合物涂布在基材上以在其上形成感光树脂涂层。基材的实例包括硅晶片、TSV硅晶片、已经通过背面抛光而变薄的硅晶片、塑料基材、陶瓷基材、以及通过离子溅射或镀覆而在表面上全部或部分地具有Ni或Au的金属涂层的基材。还可使用具有开口宽度为10至100μm、深度为10至120μm的凹槽和/或孔的基材。
涂布技术可以是任何公知的技术,例如浸涂、旋涂或辊涂。可以针对特定目的适当地选择涂层重量,优选地以形成厚度为0.1至200μm,更优选为1至150μm的感光树脂涂层。
为了使基材上的涂层厚度更均匀,可以采用在涂布树脂组合物之前在基材上滴加溶剂的预湿润技术。滴加的溶剂的类型和量可根据特定目的来选择。例如,醇如异丙醇(IPA)、酮如环己酮、和二醇如PGME是优选的。也可以使用在感光树脂组合物中所使用的溶剂。
在这一点上,为了有效的光固化反应,如果需要可以将涂层预烘烤以挥发掉溶剂等。预烘烤可以例如在40至140℃下进行1分钟至大约1小时。
接下来,在步骤(ii)中,将感光树脂涂层曝光于辐照以限定曝光和未曝光区域。曝光辐照的波长优选为1至600nm,更优选为10至600nm,甚至更优选为190至500nm。该波长范围内的辐照的示例包括来自辐照发射装置的各种波长的辐照,特别是UV辐照,例如g线、h线或i线,以及深UV(248nm、193nm)。其中,优选波长为248至436nm的辐照。合适的曝光剂量为10至10,000mJ/cm2。
下一步可以是曝光后烘烤(PEB),其有效提高显影灵敏度。PEB优选在40至150℃下进行0.5至10分钟。树脂涂层的曝光区域在PEB期间被交联而形成不溶图案,该图案不溶于作为显影剂的有机溶剂。
曝光或PEB之后是步骤(iii):将曝光的树脂涂层在显影剂中显影以溶解掉树脂涂层的未曝光区域并形成树脂涂层的图案。优选的显影剂为有机溶剂,包括醇如IPA、酮如环己酮、和二醇如PGME。在感光树脂组合物中所使用的溶剂也是有用的。显影以常规方式进行,例如将曝光的涂层浸渍于显影剂中。显影后,根据需要进行清洗、漂洗和干燥。以此方式,获得具有期望图案的树脂涂层。
在步骤(iv)中,可将图案化的涂层在烘箱中或热板上在优选100至250℃、更优选150至220℃的温度下进行后固化。感光树脂组合物确保即使在约200℃的相对较低的温度下也可通过后固化获得具有改善的膜性能的树脂涂层。后固化对于提高树脂涂层的交联密度和除去任何残留的挥发性物质是有效的。所得涂层具有增强的对基材的粘合性、耐热性、机械强度、好的电性能和结合强度。为了获得上述特性,后固化温度优选为100至250℃。后固化时间优选为10分钟至10小时,更优选为10分钟至3小时。后固化的树脂涂层的厚度为1至200μm,优选5至50μm。
尽管已经描述了图案形成过程,但是有时没有必要形成图案。例如,当只需要简单地形成均匀的膜时,可以采用与上述相同的方法,只是在步骤(ii)中,将树脂涂层直接(即不用光掩模)曝光于合适波长的辐照。
基材粘结方法
感光树脂组合物可作为用于粘结两种基材的粘合剂(或基材粘合材料)。基材粘结方法可以是在足够的温度和压力条件下将其上形成有树脂组合物的涂层的第一基材接合到第二基材上以在基材之间形成粘结的方法。具有树脂涂层的第一基材和第二基材中的一者或两者可以已经例如通过切割而被切成芯片(chip)。优选的粘结条件包括50至200℃的温度和1至60分钟的时间。可以使用任何期望的粘结装置,例如,用于在减压和特定负载下粘结晶片的晶片粘结机,或用于进行芯片-晶片或芯片-芯片粘结的倒装芯片粘结机。可以将基材之间的粘合剂层后固化处理成具有增强的粘结强度的永久粘结。
可以在与上述步骤(iv)相同的条件下将如此接合或粘结的基材进行后固化,以由此增加树脂涂层的交联密度以增强基材粘结力。应当指出,交联反应是在粘结过程中通过热而发生的。由于该交联反应不伴有脱气的副反应,因此,在将感光树脂组合物用作基材粘合剂时,不会产生接合空隙。
层叠体
本发明的又一实施方案是为层叠体,其包括基材和在其上由感光树脂组合物形成的感光树脂涂层。基材为凹凸不平的基材,具有开口宽度为10至100μm且深度为10至120μm的凹槽和/或孔。由于感光树脂涂层由感光树脂组合物形成,因此即使基材为凹凸不平的,层叠体在基材和树脂涂层之间的粘附性也得到提高,并提供高的平整度。
实施例
本发明的实施例在下文以说明的方式而不是限制的方式给出。值得注意的是,重均分子量(Mw)通过凝胶渗透色谱(GPC)相对于单分散聚苯乙烯标样使用GPC色谱柱TSKGELSuper HZM-H(Tosoh Corp.)在分析条件下测量:流速0.6mL/min,四氢呋喃洗脱液,柱温40℃。在1H-NMR光谱分析时,使用Bruker Corp.的分析仪。所有的份均以重量(pbw)计。
合成例中使用的化合物(S-1)至(S-6)如下所示。
[1]有机硅树脂的合成
合成例1
树脂1的合成
向配备有搅拌器、温度计、氮气吹扫管线和回流冷凝器的3-L烧瓶中装入63.0g(0.15mol)的化合物(S-1)、119.2g(0.45mol)的化合物(S-2)、18.6g(0.10mol)的化合物(S-3)和2,000g的甲苯,并在70℃下加热。此后,加入1.0g的氯铂酸甲苯溶液(铂浓度为0.5wt%),并在1小时内滴加58.2g(0.30mol)的化合物(S-5)和553.4g(0.20mol)的化合物(S-6),其中y1=38。氢硅烷基总量与烯基总量的摩尔比为1/1。滴加结束时,将反应溶液在100℃下加热并熟化6小时。在真空中从反应溶液中蒸馏出甲苯,得到树脂1。在1H NMR光谱分析时,发现树脂1含有重复单元(a1)、(b1)、(a3)、(b3)、(a4)和(b4)。树脂1的Mw为38,000,有机硅含量为70.4wt.%。
合成例2
树脂2的合成
在配备有搅拌器、温度计、氮气吹扫管线和回流冷凝器的3-L烧瓶中装入106.0g(0.40mol)的化合物(S-2)、64.5g(0.15mol)的化合物(S-4)、9.3g(0.05mol)的化合物(S-3)和2,000g的甲苯,并在70℃下加热。此后,加入1.0g的氯铂酸甲苯溶液(铂浓度为0.5wt%),并在1小时内滴加9.7g(0.05mol)的化合物(S-5)和276.7g(0.45mol)的化合物(S-6),其中y1=8。氢硅烷基总量与烯基总量的摩尔比为1/1。滴加结束时,将反应溶液在100℃下加热并熟化6小时。在真空中从反应溶液中蒸馏出甲苯,得到树脂2。在1H NMR光谱分析时,发现树脂2含有重复单元(a2)、(b2)、(a3)、(b3)、(a4)和(b4)。树脂2的Mw为36,000,有机硅含量为61.3wt.%。
合成例3
树脂3的合成
在配备有搅拌器、温度计、氮气吹扫管线和回流冷凝器的3-L烧瓶中装入84.0g(0.20mol)的化合物(S-1)、53.0g(0.20mol)的化合物(S-2)、43.0g(0.10mol)的化合物(S-4)和2,000g的甲苯,并在70℃下加热。此后,加入1.0g的氯铂酸甲苯溶液(铂浓度为0.5wt%),并在1小时内滴加38.8g(0.20mol)的化合物(S-5)和184.5g(0.3mol)的化合物(S-6),其中y1=8。氢硅烷基总量与烯基总量的摩尔比为1/1。滴加结束时,将反应溶液在100℃下加热并熟化6小时。在真空中从反应溶液中蒸馏出甲苯,得到树脂3。在1H NMR光谱分析时,发现树脂3含有重复单元(a1)、(b1)、(a2)、(b2)、(a3)和(b3)。树脂3的Mw为32,000,有机硅含量为45.7wt.%。
合成例4
树脂4的合成
在配备有搅拌器、温度计、氮气吹扫管线和回流冷凝器的3-L烧瓶中装入42.0g(0.10mol)的化合物(S-1)、79.5g(0.30mol)的化合物(S-2)、64.5g(0.15mol)的化合物(S-4),9.3g(0.05mol)的化合物(S-3)和2,000g的甲苯,并在70℃下加热。此后,加入1.0g的氯铂酸甲苯溶液(铂浓度为0.5wt%),并在1小时内滴加38.8g(0.20mol)的化合物(S-5)和830.1g(0.30mol)的化合物(S-6),其中y1=38。氢硅烷基总量与烯基总量的摩尔比为1/1。滴加结束时,将反应溶液在100℃下加热并熟化6小时。在真空中从反应溶液中蒸馏出甲苯,得到树脂4。在1H NMR光谱分析时,发现树脂4含有重复单元(a1)、(b1)、(a2)、(b2)、(a3)、(b3)、(a4)和(b4)。树脂4的Mw为41,000,有机硅含量为78.8wt.%。
合成例5
树脂5的合成
在配备有搅拌器、温度计、氮气吹扫管线和回流冷凝器的3-L烧瓶中装入53.0g(0.20mol)的化合物(S-2)、129.0g(0.30mol)的化合物(S-4)和2,000g的甲苯,并在70℃下加热。此后,加入1.0g的氯铂酸甲苯溶液(铂浓度为0.5wt%),并在1小时内滴加38.8g(0.20mol)的化合物(S-5)和830.1g(0.30mol)的化合物(S-6),其中y1=38。氢硅烷基总量与烯基总量的摩尔比为1/1。滴加结束时,将反应溶液在100℃下加热并熟化6小时。在真空中从反应溶液中蒸馏出甲苯,得到树脂5。在1H NMR光谱分析时,发现树脂5含有重复单元(a2)、(b2)、(a3)和(b3)。树脂5的Mw为41,000,有机硅含量为78.9wt.%。
合成例6
树脂6的合成
在装备有搅拌器、温度计、氮气吹扫管线和回流冷凝器的3-L烧瓶中装入145.7g(0.55mol)的化合物(S-2)、215.0g(0.50mol)的化合物(S-4)、9.3g(0.05mol)的化合物(S-3)和2,000g的甲苯,并在70℃下加热。此后,加入1.0g的氯铂酸甲苯溶液(铂浓度为0.5wt%),并在1小时内滴加58.2g(0.30mol)的化合物(S-5)和430.5g(0.70mol)的化合物(S-6),其中y1=8。氢硅烷基总量与烯基总量的摩尔比为1/1。滴加结束时,将反应溶液在100℃下加热并熟化6小时。在真空中从反应溶液中蒸馏出甲苯,得到树脂6。在1H NMR光谱分析时,发现树脂6含有重复单元(a2)、(b2)、(a3)、(b3)、(a4)和(b4)。树脂6的Mw为39,000,有机硅含量为51.2wt.%。
合成例7
树脂7的合成
在配备有搅拌器、温度计、氮气吹扫管线和回流冷凝器的3-L烧瓶中装入79.5g(0.30mol)的化合物(S-2)、215.0g(0.50mol)的化合物(S-4)、55.8g(0.30mol)的化合物(S-3)和2,000g的甲苯,并在70℃下加热。此后,加入1.0g的氯铂酸甲苯溶液(铂浓度为0.5wt%),并在1小时内滴加58.2g(0.30mol)的化合物(S-5)和123.0g(0.20mol)的化合物(S-6),其中y1=8。氢硅烷基总量与烯基总量的摩尔比为1/1。滴加结束时,将反应溶液在100℃下加热并熟化6小时。在真空中从反应溶液中蒸馏出甲苯,得到树脂7。在1H NMR光谱分析时,发现树脂7含有重复单元(a2)、(b2)、(a3)、(b3)、(a4)和(b4)。树脂7的Mw为32,000,有机硅含量为33.6wt.%。
[2]感光树脂组合物的制备
实施例1至12和比较例1至4
表1
表1中,光致产酸剂PAG-1、过氧化物1至3、交联剂CL-1和淬灭剂AM-1如下所示。
CL-1
AM-1
[3]树脂涂层的评价
(1)塑性变形率评价
每种感光树脂组合物的固化涂层的塑性变形率评价如下。实施例1至12和比较例1至4的感光树脂组合物分别通过棒涂机涂布在13cm×15cm×0.7mm(厚)的钢板上,并在烘箱中在190℃下烘烤2小时,以形成50μm厚的树脂涂层。将树脂涂层切成条,以20mm的间隔标记。使用拉力测试仪(Shimadzu Corp.),进行拉条,使得每个5%变形可能需要1个小时。去除负荷后,检查20mm间隔标记之间的变化。百分变化小于1%,将样品评级为“优异”,百分变化1%至小于3%,评级为“好”,百分变化大于3%,评级为“NG”。
(2)可靠性(粘附性、抗裂性)评价
实施例1至12和比较例1至4的感光树脂组合物分别通过旋涂机涂布在晶片上,在电热板上在100℃下烘烤3分钟以除去溶剂,得到10μm厚的干膜。
使用光刻机MA8(SUSS MicroTec AG),将晶片上的树脂膜整个表面直接即不通过掩模而曝光于高压水银灯发出的365nm波长的光(整片曝光)。将膜进行PEB并在PGMEA中浸渍5分钟。然后将这些操作后保留的树脂膜在烘箱中在190℃下加热1小时,得到固化膜。
使用带有切割片的切割机(DAD685,DISCO Co.,主轴转速40,000rpm,切割速度20mm/sec),将每个带有膜的晶片切割成10mm见方的样品。通过热循环测试(在-25℃下保持10分钟并在125℃下保持10分钟的测试,测试重复1000次循环)检查每个实施例的十个样品。测试后,在光学显微镜下观察树脂膜是否从晶片上剥离以及树脂膜是否开裂。当所有样品均未剥离或开裂时,样品评级为“好”;当一个或多个样品剥离时,样品评级为“剥离的”;当一个或多个样品开裂时,样品评级为“开裂的”。
(3)耐热性评价
在加热测试之前,测量样品(在以上可靠性评价中制备)的重量。将样品在烘箱中在200℃下保持1,000小时,从烘箱中取出,并再次测量重量。当测试前后的重量变化小于0.5%时,将样品评级为“好”,当测试前后的重量变化等于或大于0.5%时,将样品评级为“差”。
结果示于表2。
表2
通过引用将日本专利申请第2018-247071号并入本文中。
尽管已对一些优选的实施例进行了描述,但根据上述教导可对其进行许多变形和改变。因此可理解,在不脱离所附权利要求的范围的情况下可在具体描述以外实施本发明。
Claims (11)
1.一种感光树脂组合物,其包含:(A)含有机硅骨架的聚合物、(B)光致产酸剂、和(C)过氧化物。
2.根据权利要求1所述的组合物,其中所述含有机硅骨架的聚合物(A)包含具有式(a1)至(a4)和(b1)至(b4)的重复单元:
其中,R1至R4各自独立地为C1-C8一价烃基,m为1至600的整数,
a1至a4和b1至b4为以下范围内的数:0≤a1<1,0≤a2<1,0≤a3<1,0≤a4<1,0≤b1<1,0≤b2<1,0≤b3<1,0≤b4<1,0<a1+a2+a3+a4<1,0<b1+b2+b3+b4<1,且a1+a2+a3+a4+b1+b2+b3+b4=1,
X1为具有下式(X1)的二价基团,X2为具有下式(X2)的二价基团,X3为具有下式(X3)的二价基团,X4为具有下式(X4)的二价基团:
其中,Z1为单键、亚甲基、丙烷-2,2-二基、1,1,1,3,3,3-六氟丙烷-2,2-二基或芴-9,9-二基,R11和R12各自独立地为氢或甲基,R13和R14各自独立地为C1-C4烷基或C1-C4烷氧基,p1和p2各自独立地为0至7的整数,且q1和q2各自独立地为0至2的整数,
其中,Z2为单键、亚甲基、丙烷-2,2-二基、1,1,1,3,3,3-六氟丙烷-2,2-二基或芴-9,9-二基,R21和R22各自独立地为氢或甲基,R23和R24各自独立地为C1-C4烷基或C1-C4烷氧基,r1和r2各自独立地为0至7的整数,且s1和s2各自独立地为0至2的整数,
其中,R31和R32各自独立地为氢或甲基,且t1和t2各自独立地为0至7的整数,
其中,R41和R42各自独立地为氢或甲基,R43和R44各自独立地为C1-C8一价烃基,u1和u2各自独立地为0至7的整数,且v为0至600的整数。
3.根据权利要求1所述的组合物,其中所述过氧化物(C)为选自过氧缩酮、氢过氧化物、二烷基过氧化物、二酰基过氧化物、过氧酯和过氧化二碳酸酯化合物的有机过氧化物。
4.权利要求1的组合物,其中过氧化物(C)的含量相对于100重量份的含有机硅骨架的聚合物(A)为0.1至50重量份。
5.根据权利要求1所述的组合物,进一步包含(D)交联剂。
6.根据权利要求1所述的感光树脂组合物,进一步包含(E)溶剂。
7.根据权利要求1所述的感光树脂组合物,进一步包含(F)淬灭剂。
8.一种层叠体,其包含:具有沟槽和/或孔的基材、和在其上由权利要求1的感光树脂组合物形成的感光树脂涂层,所述沟槽和/或孔的开口宽度为10至100μm且深度为10至120μm。
9.一种图案形成方法,包括以下步骤:
(i)使用权利要求1的感光树脂组合物在基材上形成感光树脂涂层;
(ii)将感光树脂涂层曝光于辐照;和
(iii)将被曝光的树脂涂层在显影剂中显影。
10.根据权利要求9所述的图案形成方法,还包括:(iv)将由显影步骤(iii)所得到的图案化树脂涂层在100至250℃的温度下进行后固化。
11.根据权利要求9所述的图案形成方法,其中所述基材具有开口宽度为10至100μm且深度为10至120μm的沟槽和/或孔。
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Application Number | Priority Date | Filing Date | Title |
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EP3674350A1 (en) | 2020-07-01 |
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CN111381447B (zh) | 2024-03-08 |
US20200209751A1 (en) | 2020-07-02 |
EP3674350B1 (en) | 2021-11-24 |
KR20200083262A (ko) | 2020-07-08 |
JP2020106728A (ja) | 2020-07-09 |
US12055853B2 (en) | 2024-08-06 |
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