TW202014401A - 胺甲醯肟化合物及含有該化合物之聚合起始劑、以及聚合性組合物 - Google Patents
胺甲醯肟化合物及含有該化合物之聚合起始劑、以及聚合性組合物 Download PDFInfo
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- TW202014401A TW202014401A TW108127905A TW108127905A TW202014401A TW 202014401 A TW202014401 A TW 202014401A TW 108127905 A TW108127905 A TW 108127905A TW 108127905 A TW108127905 A TW 108127905A TW 202014401 A TW202014401 A TW 202014401A
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- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
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- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
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- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07F9/065—Phosphoranes containing the structure P=N-
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- C08F220/10—Esters
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Abstract
本發明之課題在於提供一種於溶劑中之溶解性高,且具有可令人滿意之感度(鹼產生能力)之化合物;以及含有該化合物作為聚合起始劑而成之聚合性組合物及其硬化物。本發明提供一種下述式(I)所表示之胺甲醯肟化合物。進而,本發明提供一種包含該化合物之聚合起始劑、含有該聚合起始劑及聚合性化合物之聚合性組合物、以及其硬化物及其製造方法。
Description
本發明係關於一種作為聚合性組合物中所使用之聚合起始劑等較有用之化合物、於聚合性化合物中含有該化合物而成之聚合性組合物、及該聚合性組合物之硬化物。
通常,感光性樹脂組合物等聚合性組合物係於感光性樹脂等聚合性化合物中添加光聚合起始劑而成者,由於可藉由能量線(光)照射使之聚合硬化、或顯影,故而被用於光硬化性油墨、感光性印刷版、各種光阻、光硬化性接著劑等中。
光聚合起始劑係以藉由能量線(光)照射產生之活性種之不同而分成光自由基產生劑、光酸產生劑、光鹼產生劑。光自由基產生劑存在硬化速度較快、硬化後不殘留活性種等優點,另一方面,存在由於產生由氧所引起之硬化阻礙,故而於薄膜之硬化中必須設置阻隔氧之層等之缺點。光酸產生劑存在不受由氧所引起之阻礙之優點,另一方面,存在因殘留活性種之酸故而使金屬基板腐蝕,或使硬化後之樹脂改性等缺點。光鹼產生劑不易產生上述由氧所引起之硬化阻礙及由殘留活性種所引起之腐蝕等問題,故而受到關注,但總體而言若與光酸產生劑比較,則存在低感度(低硬化性)之問題。光鹼產生劑例如係由專利文獻1~5等所揭示。
[先前技術文獻]
[專利文獻]
專利文獻1:US6551761(B1)
專利文獻2:US2011/233048(A1)
專利文獻3:國際公開WO2010/064632號
專利文獻4:US2015/064623(A1)
專利文獻5:日本專利特開2013-163670號
[發明所欲解決之問題]
然而,先前之光鹼產生劑就感度(鹼產生能力)及於溶劑中之溶解性之方面而言尚不充分。
因此,本發明之目的在於提供一種於溶劑中之溶解性較高,且具有可令人滿意之感度(鹼產生能力)之化合物;含有該化合物作為聚合起始劑而成之聚合性組合物及其硬化物。
[解決問題之技術手段]
本發明者進行努力研究,發現具有特定之結構之化合物作為聚合起始劑,具有較高之感度(鹼產生能力)。
本發明係藉由提供下述式(I)所表示之胺甲醯肟化合物,而達成上述目的者。
[化1]
式中,R1
及R2
分別獨立地表示氫原子、碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基,
R3
、R4
、R5
、R6
、R7
、R8
、R9
及R10
分別獨立地表示氫原子、氰基、硝基、-OR11
、-COOR11
、-CO-R11
、-SR11
、鹵素原子、碳原子數1~20之脂肪族烴基、碳原子數6~20之芳香族烴基、碳原子數2~20之含有雜環之基或下述式(II)所表示之基,
R11
表示碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基,
R1
、R2
、R3
、R4
、R5
、R6
、R7
、R8
、R9
、R10
及R11
所表示之基中之氫原子之1個或2個以上存在經鹵素原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯醚基、巰基、異氰酸酯基或碳原子數2~20之含有雜環之基取代之情形,
R3
、R4
、R5
、R6
、R7
、R8
、R9
及R10
中之一個以上為下述式(II)所表示之基。
[化2]
式中,R21
表示氫原子、氰基、鹵素原子、硝基、碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基,
X1
為-NR22
R23
、下述式(a)或下述式(b)所表示之基,
R22
及R23
分別獨立地為氫原子、碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基,或者
R22
與R23
相互連結而成為包含氮原子及碳原子之環、或包含氧原子、氮原子及碳原子之環,
R21
、R22
及R23
所表示之基中之氫原子之1個或2個以上存在經鹵素原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯醚基、巰基、異氰酸酯基或碳原子數2~20之含有雜環之基取代之情形,
n表示0或1,*表示鍵結鍵。
[化3]
式中,R31
、R32
、R33
、R34
、R35
、R36
、R37
、R38
、R39
及R40
分別獨立地為氫原子、碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基,或者
存在R31
與R32
、R33
與R34
、R35
與R36
、R37
與R38
及R39
與R40
相互連結而形成包含氮原子及碳原子之環、或包含氧原子、氮原子及碳原子之環之情形,
R31
、R32
、R33
、R34
、R35
、R36
、R37
、R38
、R39
及R40
所表示之基中之氫原子之1個或2個以上存在經鹵素原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯醚基、巰基、異氰酸酯基或碳原子數2~20之含有雜環之基取代之情形,
*表示鍵結鍵。
又,本發明提供一種包含至少1種上述式(I)所表示之胺甲醯肟化合物之潛在性鹼化合物。
又,本發明提供一種包含至少1種上述式(I)所表示之胺甲醯肟化合物之聚合起始劑。
又,本發明提供一種含有上述聚合起始劑(A)及聚合性化合物(B)之聚合性組合物、及由該聚合性組合物獲得之硬化物。
又,本發明提供一種硬化物之製造方法,其具有對上述聚合性組合物照射能量線之步驟。
[發明之效果]
本發明之胺甲醯肟化合物於用作聚合起始劑之情形時,與先前之光鹼產生劑相比可有效率地產生鹼,故而於低曝光量下亦可使聚合性化合物硬化。進而本發明之胺甲醯肟化合物於溶劑中之溶解性較高,容易操作。
又,本發明之聚合性組合物於低曝光量下顯示出較高之硬化性。
以下,對本發明對其較佳之實施形態詳細地進行說明。
本發明之胺甲醯肟化合物係上述式(I)所表示者。於式(I)所表示之胺甲醯肟化合物中存在由肟之雙鍵所引起之幾何異構物,但並未對該等加以區分。
即,於本說明書中,上述式(I)所表示之胺甲醯肟化合物、以及下述作為該化合物之較佳之形態之化合物及例示化合物係表示兩者之混合物或任一種者,並不限定於表示異構物之結構。以下,亦將式(I)所表示之胺甲醯肟化合物簡稱為「式(I)所表示之化合物」或「本發明之化合物」。
再者,於式(I)中之R1
~R11
、R21
~R23
及R31
~R40
所表示之基被包含碳原子之基切斷或取代之情形時,包含該等之碳原子數之數成為規定之碳原子數。
作為上述式(I)中之R1
~R11
及R21
~R23
及R31
~R40
所表示之碳原子數1~20之脂肪族烴基,未經取代者例如除甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、第三丁基、戊基、異戊基、第三戊基、己基、庚基、辛基、異辛基、2-乙基己基、第三辛基、壬基、異壬基、癸基、異癸基、十一烷基、十二烷基、十四烷基、十六烷基、十八烷基、二十烷基、環戊基、環己基、環己基甲基等烷基以外,可列舉將該等烷基之碳-碳單鍵之1個以上變更為碳-碳雙鍵或碳-碳三鍵而成之不飽和脂肪族烴基等。該等脂肪族烴基存在基中之亞甲基之1個或2個以上經-O-、-COO-、-OCO-、-CO-、-CS-、-S-、-SO-、-SO2
-、-NR-、-NR-CO-、-CO-NR-、-NR-COO-、-OCO-NR-或-SiRR'-取代之情形。其中,該等二價基係設為不相鄰者。
R及R'為氫原子或脂肪族烴基,作為R及R'所表示之脂肪族烴基,例如可列舉與作為R1
~R11
、R21
~R23
及R31
~R40
所表示之碳原子數1~20之脂肪族烴基所例示者同樣之基。
作為上述式(I)中之R1
~R11
、R21
~R23
及R31
~R40
所表示之碳原子數6~20之芳香族烴基,未經取代者例如可列舉:苯基、萘基、菲基、芘基及聯苯基(以下亦統稱為「苯基等」)、以及經脂肪族烴基取代之苯基等,該等芳香族烴基中之烷基部分或芳香族環與脂肪族烴基之鍵結部可經-O-、-COO-、-OCO-、-CO-、-CS-、-S-、-SO-、-SO2
-、-NR-、-NR-CO-、-CO-NR-、-NR-COO-、-OCO-NR-或-SiRR'-切斷。其中,該等切斷之二價基係設為不相鄰者。
作為取代上述苯基等之脂肪族烴基,可列舉與作為上述R1
~R11
、R21
~R23
及R31
~R40
所表示之碳原子數1~20之脂肪族烴基所例示者同樣之基。
於R1
~R11
、R21
~R23
及R31
~R40
所表示之碳原子數1~20之脂肪族烴基及R1
~R11
、R21
~R23
及R31
~R40
所表示之碳原子數6~20之芳香族烴基具有取代基之情形時,作為具有該取代基之上述脂肪族烴基及上述芳香族烴基,可列舉上述中所說明之未經取代物之氫原子經鹵素原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯醚基、巰基、異氰酸酯基或碳原子數2~20之含有雜環之基取代者。作為該碳原子數2~20之含有雜環之基,可列舉與下述R3
~R10
所表示之未經取代之碳原子數2~20之含有雜環之基之例同樣者。
作為存在R3
~R11
所表示之鹵素原子以及R1
~R11
、R21
~R23
及R31
~R40
所表示之基中之氫原子經取代之情形時之鹵素原子,可列舉氟、氯、溴、碘之各原子。
於本發明中,所謂「包含氮原子及碳原子之環」係指形成環之骨架之原子僅包含氮原子及碳原子之環。又,所謂「包含氧原子、氮原子及碳原子之環」係指形成環之骨架之原子僅包含氧原子、氮原子及碳原子之環。
作為R22
與R23
、R31
與R32
、R33
與R34
、R35
與R36
、R37
與R38
及R39
與R40
相互連結而形成之包含氮原子及碳原子之環,作為包含鍵結之氮原子之基,除吡咯環、吡咯啶環、咪唑環、咪唑啶環、咪唑啉環、吡唑環、吡唑啶環、哌啶環、哌𠯤環等(以下亦統稱為「吡咯環等」)以外,亦可列舉該等吡咯環等經脂肪族烴基取代之基。作為該脂肪族烴基,可列舉與作為上述R1
~R11
、R21
~R23
及R31
~R40
所表示之碳原子數1~20之脂肪族烴基所例示者同樣之基。
該等包含氮原子及碳原子之環中之氫原子之1個或2個以上可經鹵素原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯醚基、巰基、異氰酸酯基或碳原子數2~20之含有雜環之基取代。作為該碳原子數2~20之含有雜環之基,可列舉與下述R3
~R10
所表示之未經取代之碳原子數2~20之含有雜環之基之例同樣者。
作為R22
與R23
、R31
與R32
、R33
與R34
、R35
與R36
、R37
與R38
及R39
與R40
相互連結而形成之包含氧原子、氮原子及碳原子之環,作為包含鍵結之氮原子之基,除𠰌啉環、㗁唑環、㗁唑啉環、㗁二唑環等(以下亦統稱為「𠰌啉環等」)以外,亦可列舉該等𠰌啉環等經脂肪族烴基取代之基。作為該脂肪族烴基,可列舉與作為上述R1
~R11
、R21
~R23
及R31
~R40
所表示之碳原子數1~20之脂肪族烴基所例示者同樣之基。
該等包含氧原子、氮原子及碳原子之環等中之氫原子之1個或2個以上可經鹵素原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯醚基、巰基、異氰酸酯基或碳原子數2~20之含有雜環之基取代。
作為上述碳原子數2~20之含有雜環之基,可列舉與下述R3
~R10
所表示之未經取代之碳原子數2~20之含有雜環之基之例同樣者。
作為上述式(I)中之R3
~R10
所表示之碳原子數2~20之含有雜環之基,作為未經取代者,可列舉:四氫呋喃基、二氧戊環基、四氫吡喃基、𠰌啉基呋喃基、噻吩基、甲基噻吩基、己基噻吩基、苯并噻吩基、吡咯基、吡咯啶基、咪唑基、咪唑啶基、咪唑啉基、吡唑基、吡唑啶基、哌啶基及哌𠯤基、以及經脂肪族烴基取代之四氫呋喃基、二氧戊環基、四氫吡喃基、𠰌啉基呋喃基、噻吩基、甲基噻吩基、己基噻吩基、苯并噻吩基、吡咯基、吡咯啶基、咪唑基、咪唑啶基、吡唑基、吡唑啶基、哌啶基及哌𠯤基等(以下亦統稱為「四氫呋喃基等」)、及該等四氫呋喃基等經脂肪族烴基取代之基。作為該脂肪族烴基,可列舉與作為上述R1
~R11
、R21
~R23
及R31
~R40
所表示之碳原子數1~20之脂肪族烴基所例示者同樣之基。
該等含有雜環之基中之烷基部分及雜環與脂肪族烴基之鍵結部可經-O-、-COO-、-OCO-、-CO--CS-、-S-、-SO-、-SO2
-、-NR-、-NR-CO-、-CO-NR-、-NR-COO-、-OCO-NR-或-SiRR'-切斷。其中,該等切斷之二價基係設為不相鄰者。再者,於本說明書中,「碳原子數2~20之含有雜環之基」中之「2~20」規定「含有雜環之基」之碳原子數而不規定「雜環」之碳原子數。
於R3
~R10
所表示之碳原子數2~20之含有雜環之基具有取代基之情形時,作為具有該取代基之含有上述雜環之基,可列舉上述中所說明之含有未經取代之雜環之基之氫原子經鹵素原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯醚基、巰基、異氰酸酯基或碳原子數2~20之含有雜環之基取代者。
上述式(I)所表示之化合物之中,該式(I)中之X1
表示-NR22
R23
,且
R22
及R23
分別獨立地為碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基,或者
R22
為氫原子,R23
為碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基,或者
R22
與R23
相互連結而形成包含氮原子及碳原子之環、或包含氧原子、氮原子及碳原子之環之化合物於用作聚合起始劑之情形時,就感度優異之方面而言較佳。
尤其是上述式(I)中之X1
表示-NR22
R23
,且
R22
與R23
相互連結而形成包含氮原子及碳原子之環之化合物由於產生之鹼種之反應性較高,故而於用作聚合起始劑之情形時,及感度優異之方面而言較佳。尤佳為包含氮原子及碳原子之環為5員環或6員環,且環中所含之氮原子數為1或2之化合物。
又,上述式(I)中之X1
表示-NR22
R23
,且
R22
與R23
分別獨立地為碳原子數1~20之脂肪族烴基之化合物之溶解性優異,故而較佳。該烴基較佳為碳原子數1~10之烷基。
又,上述式(I)中之X1
表示-NR22
R23
,且
R22
為氫原子,R23
為碳原子數6~20之芳香族烴基之化合物之穩定性優異,故而較佳。該芳香族烴基之碳原子數較佳為碳原子數1~10。該芳香族烴基較佳為苯基。
上述式(I)中之R3
、R4
、R5
、R6
、R7
、R8
、R9
及R10
中之2個以上為上述式(II)所表示之基之化合物於用作聚合起始劑之情形時,就感度優異,所獲得之硬化物之殘膜率較高之方面而言較佳,尤佳為R3
、R4
、R5
、R6
、R7
、R8
、R9
及R10
中之2~3個為上述式(II)所表示之基之化合物。
其中,就化合物之穩定性較高之方面而言,較佳為上述式(I)中之R3
、R4
、R5
及R6
之至少1個為上述式(II)所表示之基,且R7
、R8
、R9
及R10
之至少1個為上述式(II)所表示之基之化合物。尤其是上述式(I)中之R4
或R9
為上述式(II)所表示之基之化合物就化合物之穩定性較高,生產性優異之方面而言較佳,最佳為上述式(I)中之R4
及R9
為上述式(II)所表示之基之化合物。
於上述式(I)中之R3
、R4
、R5
、R6
、R7
、R8
、R9
及R10
中之2個以上為上述式(II)所表示之基之情形時,該2個以上之上述式(II)所表示之基中,所存在之2個以上之X1
可相同亦可不同。於上述情形時,所存在之2個以上之R21
可相同亦可不同。又,2個以上之上述式(II)所表示之基中之n可相同亦可不同。於上述式(I)中之R3
、R4
、R5
、R6
、R7
、R8
、R9
及R10
中之2個以上為上述式(II)所表示之基之情形時,就生產性之觀點而言,較佳為該等複數個式(II)所表示之基中之X1
彼此、R21
彼此及n彼此分別相同。
進而,上述式(I)中之R3
、R4
、R5
及R6
之中,1個為上述式(II)所表示之基,且其他3個分別獨立地為氫原子、未經取代或具有取代基之碳原子數1~6之脂肪族烴基或未經取代或具有取代基之碳原子數6~12之芳香族烴基之化合物就感度較高,並且容易製造之方面而言較佳,尤佳為R4
及R6
之中,1個為上述式(II)所表示之基,且其他以及R3
及R5
分別獨立地為氫原子、未經取代或具有取代基之碳原子數1~6之脂肪族烴基或未經取代或具有取代基之碳原子數6~12之芳香族烴基之化合物。
同樣地,上述式(I)中之R7
~R10
之中,1個為上述式(II)所表示之基,且其他為氫原子、未經取代或具有取代基之碳原子數1~6之脂肪族烴基或未經取代或具有取代基之碳原子數6~12之芳香族烴基之化合物就感度較高,並且容易製造之方面而言較佳。
上述式(I)中之R3
、R4
、R5
及R6
之中,1個為上述式(II)所表示之基,且R7
、R8
、R9
及R10
中之至少1個為氫原子、硝基或碳原子數6~12之芳香族烴基、較佳為硝基或碳原子數6~12之芳香族烴基之化合物、尤其是R7
、R8
、R9
及R10
中之1個為硝基或碳原子數6~12之芳香族烴基之化合物就感度較高,並且容易製造之方面而言較佳。該芳香族烴基可未經取代,亦可具有取代基,該芳香族烴基較佳為苯甲醯基。
上述式(I)中之R4
或R9
為硝基、三氟甲基或苯甲醯基之化合物就感度優異之方面而言較佳。
R1
及R2
所表示之基相互可相同亦可不同,就製造上較容易之方面而言,較佳為相同。
上述式(I)中之R1
及R2
為碳原子數2以上之脂肪族烴基之化合物就於溶劑中之溶解性優異之方面而言較佳,尤佳為碳原子數2~10之脂肪族烴基。
作為上述式(I)中之R1
及R2
,脂肪族烴基之中,就於溶劑中之溶解性、感度及透明性優異之方面而言,較佳為烷基。
上述式(I)中之R1
及R2
為碳原子數1~4之脂肪族烴基之化合物也是就於溶劑中之溶解性優異之方面而言較佳。作為該脂肪族烴基,就於溶劑中之溶解性、感度及透明性優異之方面而言,較佳為烷基。
就於溶劑中之溶解性優異之方面而言,較佳為R21
為碳原子數2以上之脂肪族烴基之化合物,就感度優異之方面而言,尤佳為碳原子數2~10之脂肪族烴基。
作為R21
,脂肪族烴基之中,就於溶劑中之溶解性、感度及透明性優異之方面而言,較佳為烷基。
式(II)中之n為0之化合物於用作聚合起始劑之情形時,對於熱之穩定性較高,故而較佳。
式(II)中之n為1之化合物於用作聚合起始劑之情形時,以低曝光量進行硬化,故而較佳。
作為上述式(I)所表示之化合物之具體例,可列舉以下之化合物No.1~No.54。但本發明並不受到以下之化合物之任何限制。
上述式(I)所表示之本發明之胺甲醯肟化合物並無特別限定,於n=0之情形時,可列舉依據下述反應式1,並藉由以下之方法製造之方法。
即,眾所周知,藉由使市售之茀化合物與醯氯於氯化鋁等路易斯酸之存在下進行反應而獲得酮化合物A,並藉由使酮化合物A與鹽酸羥胺於吡啶等鹼之存在下進行反應,而獲得肟化合物A。繼而,藉由使氯甲酸4-硝基苯酯與肟化合物A反應,繼而使該胺反應,而獲得由上述式(I)所表示且n=0之本發明之胺甲醯肟化合物A。
於n=1之情形時,依據下述反應式2,眾所周知,藉由使市售之茀化合物與醯氯於氯化鋁等路易斯酸之存在下進行反應而獲得酮化合物B,於酸性條件下使亞硝酸異丁酯與酮體B反應而獲得肟化合物B。繼而,藉由使氯甲酸4-硝基苯酯與肟化合物B反應,繼而使該胺反應,而獲得由上述式(I)所表示且n=1之本發明之胺甲醯肟化合物B。
再者,酮體亦可使用公知者。
又,上述反應式1及反應式2均表示X1
為-NR22
R23
之情形,藉由變更所使用之胺,亦可製造X1
為式(a)或式(b)所表示之基之化合物。
上述反應式1及反應式2均表示R4
為式(II)所表示之基之情形,於在茀中向另一位置導入式(II)所表示之基之情形時,可藉由在茀環形成時導入酮基之方法而獲得。
進而,例如,R3
、R4
、R5
、R6
、R7
、R8
、R9
及R10
中之2個以上為式(II)所表示之基之化合物可藉由使用羰基與R3
、R4
、R5
、R6
、R7
、R8
、R9
及R10
之2個以上鍵結之二酮體作為酮體,並利用與上述反應式1及2同樣之方法而製造。
肟化合物A亦可藉由日本專利4223071號報中所記載之方法製造。
本發明之化合物就感光性樹脂之硬化性優異之方面、對於能量線之感度較高之方面而言,可適宜地用作以下所說明之作為光鹼產生劑之聚合起始劑,此外還可用於化學增幅型抗蝕劑等。
於丙二醇-1-單甲醚-2-乙酸酯中之25℃下之溶解性為15%以上之化合物就於製作本發明之聚合性組合物時,可選擇較多之聚合性化合物之方面而言較佳。再者,溶解性可藉由下述實施例中所記載之方法進行測定。
其次,對本發明之潛在性鹼化合物、聚合起始劑及本發明之聚合性組合物進行說明。再者,關於未特別說明之方面,適當應用本發明之化合物之說明。
<潛在性鹼化合物>
上述式(I)所表示之胺甲醯肟化合物為潛在性鹼化合物。所謂潛在性鹼化合物係藉由紫外線等光照射或加熱而產生鹼之化合物,可用作聚合起始劑、鹼觸媒、pH值調整劑。就操作性優異之方面而言,更佳為藉由照射光而產生鹼之光潛在性鹼化合物。
<聚合起始劑(A)>
於本發明之聚合起始劑及本發明之聚合性組合物中,聚合起始劑(A)係包含至少1種上述式(I)所表示之胺甲醯肟化合物者。本發明之胺甲醯化合物由於藉由光之照射或加熱有效率地產生鹼及自由基,故而作為鹼產生劑及自由基聚合起始劑而較有用,尤其是作為鹼產生劑而較有用。
上述鹼產生劑及自由基聚合起始劑之中,由於操作性優異,故而作為光鹼產生劑及光自由基聚合起始劑而較有用,尤其是作為光鹼產生劑而較有用。
上述聚合起始劑中之上述式(I)所表示之化合物之含量較佳為1~100質量%,更佳為50~100質量%。
於本發明之聚合性組合物中,聚合起始劑(A)之含量相對於聚合性化合物(B)100質量份,較佳為1~20質量份、更佳為1~10質量份。藉由聚合起始劑(A)之含量為1質量份以上,容易防止由感度不足所引起之硬化不良,故而較佳,藉由設為20質量份以下,可抑制光照射時或加熱時之揮發物,故而較佳。
<聚合性化合物(B)>
作為本發明中所使用之聚合性化合物(B),可列舉:具有陰離子聚合性官能基之化合物、藉由鹼作為觸媒起作用之反應或鹼之加成反應而硬化之化合物、及自由基聚合性化合物,較佳為藉由照射紫外線等能量線進行聚合而硬化之感光性樹脂、或硬化溫度低溫化之硬化樹脂。上述所謂陰離子聚合性官能基係指可藉由利用紫外線等能量線由光鹼產生劑產生之鹼而進行聚合之官能基,例如可列舉:環氧基、環硫化物基、環狀單體(σ-戊內酯、ε-己內醯胺)、丙二酸酯等。作為鹼作為觸媒起作用之反應或鹼之加成反應,可列舉:由異氰酸酯與醇之胺基甲酸酯鍵形成反應、環氧樹脂與含有羥基之化合物之加成反應、環氧樹脂與含有羧酸基之化合物之加成反應、環氧樹脂與硫醇化合物之加成反應、(甲基)丙烯酸基之麥可加成反應、聚醯胺酸之脫水縮合反應、烷氧基矽烷之水解-縮聚反應等。
作為具有陰離子聚合性官能基之化合物,例如可列舉:環氧樹脂、氧雜環丁烷樹脂、環硫化物樹脂、環狀醯胺(內醯胺系化合物)、環狀酯(內酯系化合物)、環狀碳酸酯系化合物、丙二酸酯等。作為藉由鹼作為觸媒起作用之反應或鹼之加成反應而硬化之化合物,例如可列舉:聚醯胺樹脂(由脫水環化所引起之聚醯亞胺化反應)、環氧樹脂-羥基系(開環加成反應)、環氧樹脂-羧酸系(開環加成反應)、環氧樹脂-硫醇系(開環加成反應)、環氧樹脂-酸酐系(開環縮聚)、氰酸酯(環化反應)、氰酸酯-環氧樹脂系(環化反應)、氰酸酯(環化反應)、氰酸酯-順丁烯二醯亞胺系(交聯共聚合)、氧雜環丁烷-羥基系(開環加成反應)、氧雜環丁烷-羧酸系(開環加成反應)、氧雜環丁烷-硫醇系(開環加成反應)、氧雜環丁烷-酸酐系(開環縮聚)、環硫化物-羥基系(開環加成反應)、環硫化物-羧酸系(開環加成反應)、環硫化物-硫醇系(開環加成反應)、環硫化物-酸酐系(開環縮聚)丙烯酸-硫醇系(麥可加成反應)、甲基丙烯酸-硫醇系(麥可加成反應)、丙烯酸-胺系(麥可加成反應)、甲基丙烯酸-胺系(麥可加成反應)、羧酸-羥基系(聚酯化反應)、羧酸-胺系(聚醯胺化反應)、異氰酸酯-羥基系(聚胺基甲酸酯化反應)、烷氧基矽烷系(水解-縮聚)等。作為利用自由基而進行聚合之化合物,可列舉乙烯性不飽和化合物。就反應性較高之方面而言,較佳為使用進行自由基聚合之化合物。該等樹脂可單獨使用,亦可併用兩種以上。作為較佳之組合,就迅速進行反應或接著性良好之方面而言,可列舉環氧樹脂與酚樹脂之組合,就低溫硬化性優異之方面而言,可列舉環氧樹脂與硫醇化合物之組合,就反應性較高之方面而言,可列舉乙烯性不飽和化合物與硫醇化合物之組合。
作為上述環氧樹脂,例如可列舉:對苯二酚、間苯二酚、兒茶酚、間苯三酚等單核多酚化合物之聚縮水甘油醚化合物;二羥基萘、聯苯酚、亞甲基雙酚(雙酚F)、亞甲基雙(鄰甲酚)、亞乙基雙酚、亞異丙基雙酚(雙酚A)、4,4'-二羥基二苯甲酮、亞異丙基雙(鄰甲酚)、四溴雙酚A、1,3-雙(4-羥基異丙苯基苯)、1,4-雙(4-羥基異丙苯基苯)、1,1,3-三(4-羥基苯基)丁烷、1,1,2,2-四(4-羥基苯基)乙烷、硫代雙酚、磺基雙酚、氧基雙酚、苯酚酚醛清漆、鄰甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、間苯二酚酚醛清漆、萜酚等多核多酚化合物之聚縮水甘油醚化合物;乙二醇、丙二醇、丁二醇、己二醇、聚二醇、硫代雙乙醇、甘油、三羥甲基丙烷、季戊四醇、山梨醇、雙酚A-環氧乙烷加成物等多元醇類之聚縮水甘油醚;順丁烯二酸、反丁烯二酸、伊康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、偏苯三甲酸、1,3,5-苯三甲酸、均苯四甲酸、四氫鄰苯二甲酸、六氫鄰苯二甲酸、內亞甲基四氫鄰苯二甲酸等脂肪族、芳香族或脂環族多元酸之縮水甘油酯類、及甲基丙烯酸縮水甘油酯之均聚物或共聚物;N,N-二縮水甘油基苯胺、雙(4-(N-甲基-N-縮水甘油基胺基)苯基)甲烷、二縮水甘油基鄰甲苯胺等具有縮水甘油基胺基之環氧化合物;乙烯基環己烯二環氧化物、二環戊烷二烯二環氧化物、3,4-環氧環己烷羧酸-3,4-環氧環己基甲酯、6-甲基環己烷羧酸-3,4-環氧-6-甲基環己基甲酯、己二酸雙(3,4-環氧-6-甲基環己基甲基)酯等環狀烯烴化合物之環氧化物;環氧化聚丁二烯、環氧化丙烯腈-丁二烯共聚物、環氧化苯乙烯-丁二烯共聚物等環氧化共軛二烯聚合物、異氰尿酸三縮水甘油酯等雜環化合物。又,該等環氧樹脂可為由末端異氰酸酯之預聚物進行內部交聯所得者或利用多價活性氫化合物(多酚、聚胺、含羰基之化合物、多磷酸酯等)進行高分子量化所得者。
上述環氧樹脂之中,就硬化性優異之觀點而言,較佳為具有縮水甘油基者,更佳為具有2官能以上之縮水甘油基者。
作為上述酚樹脂,較佳為1分子中具有2個以上之羥基之酚樹脂,通常可使用公知者。作為酚樹脂,例如可列舉:雙酚A型酚樹脂、雙酚E型酚樹脂、雙酚F型酚樹脂、雙酚S型酚樹脂、苯酚酚醛清漆樹脂、雙酚A酚醛清漆型酚樹脂、縮水甘油酯型酚樹脂、芳烷基酚醛清漆型酚樹脂、聯苯芳烷基型酚樹脂、甲酚酚醛清漆型酚樹脂、多官能酚樹脂、萘酚樹脂、萘酚酚醛清漆樹脂、多官能萘酚樹脂、蒽型酚樹脂、萘骨架改性酚醛清漆型酚樹脂、苯酚芳烷基型酚樹脂、萘酚芳烷基型酚樹脂、二環戊二烯型酚樹脂、聯苯型酚樹脂、脂環式酚樹脂、多元醇型酚樹脂、含磷之酚樹脂、含聚合性不飽和烴基之酚樹脂及含羥基之聚矽氧樹脂類,但並無特別限制。該等酚樹脂可單獨使用一種或組合兩種以上而使用。
上述硫醇化合物並無特別限制,包含所有硫醇化合物,較佳為1分子中具有2個以上之硫醇基者。
作為硫醇化合物之較佳之具體例,可列舉:雙(2-巰基乙基)硫醚、2,5-二巰基甲基-1,4-二噻烷、1,3-雙(巰基甲基)苯、1,4-雙(巰基甲基)苯、4-巰基甲基-1,8-二巰基-3,6-二硫雜辛烷、4,8-二巰基甲基-1,11-二巰基-3,6,9-三硫雜十一烷、4,7-二巰基甲基-1,11-二巰基-3,6,9-三硫雜十一烷、5,7-二巰基甲基-1,11-二巰基-3,6,9-三硫雜十一烷、1,2,6,7-四巰基-4-硫雜庚烷、季戊四硫醇、1,1,3,3-四(巰基甲硫基)丙烷、季戊四醇四巰基丙酸酯、季戊四醇四巰基乙酸酯、三羥甲基丙烷三巰基乙酸酯、及三羥甲基丙烷三巰基丙酸酯,更佳為1,2,6,7-四巰基-4-硫雜庚烷、季戊四硫醇、雙(2-巰基乙基)硫醚、2,5-雙(2-巰基甲基)-1,4-二噻烷、4-巰基甲基-1,8-二巰基-3,6-二硫雜辛烷、1,3-雙(巰基甲基)苯、季戊四醇四巰基丙酸酯、及季戊四醇四巰基乙酸酯。
尤佳之化合物為1,2,6,7-四巰基-4-硫雜庚烷、季戊四硫醇、雙(2-巰基乙基)硫醚、2,5-二巰基甲基-1,4-二噻烷、及4-巰基甲基-1,8-二巰基-3,6-二硫雜辛烷。
硫醇化合物可單獨使用一種或組合兩種以上而使用。
作為上述聚醯胺樹脂,可列舉以作為酸二酐之乙烯四羧酸二酐、1,2,3,4-苯四羧酸二酐、1,2,3,4-環己烷四羧酸二酐、2,2',3,3'-二苯甲酮四羧酸二酐、2,2,3,3-聯苯四羧酸二酐、1,4,5,8-萘四羧酸二酐、作為二胺之(鄰、間或對)苯二胺、(3,3'-或4,4'-)二胺基二苯醚、二胺基二苯甲酮、(3,3'-或4,4'-)二胺基二苯甲烷等為原料之樹脂。
作為上述聚胺基甲酸酯樹脂,可列舉以作為二異氰酸酯之甲苯二異氰酸酯、六亞甲基二異氰酸酯、二苯甲烷二異氰酸酯、異佛爾酮二異氰酸酯等多官能異氰酸酯、及聚醚多元醇、聚酯多元醇、聚碳酸酯多元醇等多元醇(多官能醇)為原料之樹脂等。
又,作為上述尼龍樹脂,可列舉以ε-己內醯胺、月桂基內醯胺等環狀單體為原料之樹脂等。
又,作為上述聚酯樹脂,可列舉以δ-戊內酯、β-丙內酯等環狀單體為原料之樹脂等。
作為上述乙烯性不飽和化合物,例如可列舉:乙烯、丙烯、丁烯、異丁烯、氯乙烯、偏二氯乙烯、偏二氟乙烯、四氟乙烯等不飽和脂肪族烴;(甲基)丙烯酸、α-氯丙烯酸、伊康酸、順丁烯二酸、檸康酸、反丁烯二酸、雙環庚烯二甲酸、丁烯酸、異丁烯酸、乙烯基乙酸、烯丙基乙酸、桂皮酸、山梨酸、甲基反丁烯二酸、琥珀酸單[2-(甲基)丙烯醯氧基乙基]酯、鄰苯二甲酸單[2-(甲基)丙烯醯氧基乙基]酯、ω-羧基聚己內酯單(甲基)丙烯酸酯等於兩末端具有羧基與羥基之聚合物之單(甲基)丙烯酸酯;(甲基)丙烯酸羥基乙酯-順丁烯二酸酯、(甲基)丙烯酸羥丙基酯-順丁烯二酸酯、二環戊二烯-順丁烯二酸酯或具有1個羧基與2個以上之(甲基)丙烯醯基之多官能(甲基)丙烯酸酯等不飽和多元酸;(甲基)丙烯酸-2-羥基乙酯、(甲基)丙烯酸-2-羥丙酯、(甲基)丙烯酸縮水甘油酯、下述丙烯基化合物No.1~No.4、(甲基)丙烯酸甲酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸甲氧基乙酯、(甲基)丙烯酸二甲酯胺基甲酯、(甲基)丙烯酸二甲酯胺基乙酯、(甲基)丙烯酸胺基丙酯、(甲基)丙烯酸二甲酯胺基丙酯、(甲基)丙烯酸乙氧基乙酯、(甲基)丙烯酸聚(乙氧基)乙酯、(甲基)丙烯酸丁氧基乙氧基乙酯、(甲基)丙烯酸乙酯己酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸四氫呋喃酯、(甲基)丙烯酸乙烯酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸苄酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、三羥甲基乙烷三(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、三環癸烷二羥甲基二(甲基)丙烯酸酯、異氰尿酸三[(甲基)丙烯醯基乙基]酯、聚酯(甲基)丙烯酸酯低聚物等不飽和一元酸及多元醇或多酚之酯;(甲基)丙烯酸鋅、(甲基)丙烯酸鎂等不飽和多元酸之金屬鹽;順丁烯二酸酐、伊康酸酐、檸康酸酐、甲基四氫鄰苯二甲酸酐、四氫鄰苯二甲酸酐、三烷基四氫鄰苯二甲酸酐、5-(2,5-二氧雜四氫呋喃基)-3-甲基-3-環己烯-1,2-二羧酸二酐、三烷基四氫鄰苯二甲酸酐-順丁烯二酸酐加成物、十二烯基琥珀酸酐、甲基雙環庚烯二甲酸酐等不飽和多元酸之酸酐;(甲基)丙烯醯胺、亞甲基雙-(甲基)丙烯醯胺、二伸乙基三胺三(甲基)丙烯醯胺、苯二甲基雙(甲基)丙烯醯胺、α-氯丙烯醯胺、N-2-羥基乙基(甲基)丙烯醯胺等不飽和一元酸及多元胺之醯胺;丙烯醛等不飽和醛;(甲基)丙烯腈、α-氯丙烯腈、二氰亞乙烯、氰化烯丙基等不飽和腈;苯乙烯、4-甲基苯乙烯、4-乙基苯乙烯、4-甲氧基苯乙烯、4-羥基苯乙烯、4-氯苯乙烯、二乙烯苯、乙烯基甲苯、乙烯苯甲酸、乙烯基苯酚、乙烯基磺酸、4-乙烯苯磺酸、乙烯基苄基甲醚、乙烯基苄基縮水甘油醚等不飽和芳香族化合物;甲基乙烯基酮等不飽和酮;乙烯基胺、烯丙基胺、N-乙烯基吡咯啶酮、乙烯基哌啶等不飽和胺化合物;烯丙醇、巴豆醇等乙烯醇;乙烯基甲醚、乙烯基乙醚、正丁基乙烯醚、異丁基乙烯醚、烯丙基縮水甘油醚等乙烯醚;順丁烯二醯亞胺、N-苯基順丁烯二醯亞胺、N-環己基順丁烯二醯亞胺等不飽和醯亞胺類;茚、1-甲基茚等茚類;1,3-丁二烯、異戊二烯、氯丁二烯等脂肪族共軛二烯類;聚苯乙烯、聚(甲基)丙烯酸甲酯、聚(甲基)丙烯酸正丁酯、聚矽氧烷等於聚合物分子鏈之末端具有單(甲基)丙烯醯基之巨單體類;乙烯氯、偏二氯乙烯、琥珀酸二乙烯酯、鄰苯二甲酸二烯丙酯、磷酸三烯丙酯、異氰尿酸三烯丙酯、乙烯基硫醚、乙烯基咪唑、乙烯基㗁唑啉、乙烯基咔唑、乙烯基吡咯啶酮、乙烯基吡啶、含羥基之乙烯基單體及聚異氰酸酯化合物之乙烯基胺基甲酸酯化合物、含羥基之乙烯基單體及聚環氧化合物之乙烯基環氧化合物。
乙烯性不飽和化合物可單獨使用或混合兩種以上而使用。
作為上述乙烯性不飽和化合物,可使用市售品,例如可列舉:Kayarad DPHA、DPEA-12、PEG400DA、THE-330、RP-1040、NPGDA、PET30、R-684(以上、日本化藥製造);ARONIX M-215、M-350(以上、東亞合成製造);NK ESTER A-DPH、A-TMPT、A-DCP、A-HD-N、TMPT、DCP、NPG及HD-N(以上、新中村化學工業製造);SPC-1000、SPC-3000(以上、昭和電工製造)等。
聚合性組合物(B)之含量只要為視其使用目的而適合之量即可,為了防止硬化不良,聚合性組合物中之固形物成分(溶劑以外之全部成分)之中,較佳為以成為50質量份以上之方式含有,更佳為60質量份以上,尤佳為70質量份以上。
<添加劑>
於本發明之聚合性組合物中,作為任意成分,可使用無機化合物、色材、潛在性環氧硬化劑、鏈轉移劑、增感劑、溶劑等添加劑。
作為上述無機化合物,例如可列舉:氧化鎳、氧化鐵、氧化銥、氧化鈦、氧化鋅、氧化鎂、氧化鈣、氧化鉀、二氧化矽、氧化鋁等金屬氧化物;層狀黏土礦物、米洛麗藍、碳酸鈣、碳酸鎂、鈷系、錳系、玻璃粉末(尤其是玻璃料)、雲母、滑石、高嶺土、亞鐵氰化物、各種金屬硫酸鹽、硫化物、硒化物、鋁矽酸鹽、鈣矽酸鹽、氫氧化鋁、鉑、金、銀、銅等。該等無機化合物例如可用作填充劑、抗反射劑、導電材、穩定劑、阻燃劑、機械強度提昇劑、特殊波長吸收劑、斥油墨劑等。
作為上述色材,可列舉:顏料、染料、天然色素等。該等色材可單獨使用或混合兩種以上而使用。
作為上述顏料,例如可使用亞硝基化合物;硝基化合物;偶氮化合物;二偶氮化合物;𠮿化合物;喹啉化合物;蒽醌化合物;香豆素化合物;酞菁化合物;異吲哚啉酮化合物;異吲哚啉化合物;喹吖酮化合物;蒽締蒽酮化合物;紫環酮化合物;苝化合物;二酮基吡咯并吡咯化合物;硫靛藍化合物;二㗁𠯤化合物;三苯甲烷化合物;喹酞酮化合物;萘四羧酸;偶氮染料、花青染料之金屬錯合物化合物;色澱顏料;藉由爐法、導槽法或熱法而獲得之碳黑、或乙炔黑、科琴黑或燈黑等碳黑;利用環氧樹脂調整或被覆上述碳黑而成者、預先於溶劑中利用樹脂對上述碳黑進行分散處理而成者、吸附有20~200 mg/g之樹脂者、對上述碳黑進行酸性或鹼性表面處理而成者、平均粒徑為8 nm以上且DBP(Dibutyl phthalate,鄰苯二甲酸二丁酯)吸油量為90 ml/100 g以下之碳黑、根據950℃下之揮發分中之CO及CO2
算出之總氧量為表面積每100 m2
為9 mg以上之碳黑;石墨、石墨化碳黑、活性碳、碳纖維、奈米碳管、螺旋碳纖維、碳奈米角、碳氣凝膠、富勒烯;苯胺黑、顏料黑7、鈦黑;氧化鉻綠、米洛麗藍、鈷綠、鈷青、錳系、亞鐵氰化物、磷酸鹽群青、鐵藍、群青、天藍、鉻綠、翡翠綠、硫酸鉛、黃丹、鋅黃、鐵丹(紅色氧化鐵(III))、鎘紅、合成鐵黑、棕土等有機或無機顏料。該等顏料可單獨使用、或混合複數種而使用。
作為上述顏料,亦可使用市售之顏料,例如可列舉:顏料紅1、2、3、9、10、14、17、22、23、31、38、41、48、49、88、90、97、112、119、122、123、144、149、166、168、169、170、171、177、179、180、184、185、192、200、202、209、215、216、217、220、223、224、226、227、228、240、254;顏料橙13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65、71;顏料黃1、3、12、13、14、16、17、20、24、55、60、73、81、83、86、93、95、97、98、100、109、110、113、114、117、120、125、126、127、129、137、138、139、147、148、150、151、152、153、154、166、168、175、180、185;顏料綠7、10、36;顏料藍15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62、64;顏料紫1、19、23、27、29、30、32、37、40、50等。
作為上述染料,可列舉:偶氮染料、蒽醌染料、靛藍染料、三芳基甲烷染料、𠮿染料、茜素染料、吖啶染料茋染料、噻唑染料、萘酚染料、喹啉染料、硝基染料、吲達胺染料、㗁𠯤染料、酞菁染料、花青染料等染料等,該等可混合複數種而使用。
作為上述潛在性環氧硬化劑,例如可列舉:雙氰胺、改性聚胺、醯肼類、4,4'-二胺基二苯基碸、三氟化硼胺錯鹽、咪唑類、胍胺類、咪唑類、脲類及三聚氰胺等。
作為上述鏈轉移劑或增感劑,通可使用常含硫原子之化合物。例如可列舉:硫代乙醇酸、硫代蘋果酸、硫代水楊酸、2-巰基丙酸、3-巰基丙酸、3-巰基丁酸、N-(2-巰基丙醯基)甘胺酸、2-巰基菸鹼酸、3-[N-(2-巰基乙基)胺甲醯基]丙酸、3-[N-(2-巰基乙基)胺基]丙酸、N-(3-巰基丙醯基)丙胺酸、2-巰基乙磺酸、3-巰基丙磺酸、4-巰基丁磺酸、十二烷基(4-甲硫基)苯醚、2-巰基乙醇、3-巰基-1,2-丙二醇、1-巰基-2-丙醇、3-巰基-2-丁醇、巰基苯酚、2-巰基乙基胺、2-巰基咪唑、2-巰基苯并咪唑、2-巰基-3-吡啶醇、2-巰基苯并噻唑、巰基乙酸、三羥甲基丙烷三(3-巰基丙酸酯)、季戊四醇四(3-巰基丙酸酯)等巰基化合物、使該巰基化合物氧化而獲得之二硫醚化合物、碘乙酸、碘丙酸、2-碘乙醇、2-碘乙磺酸、3-碘丙磺酸等碘化烷基化合物、三羥甲基丙烷三(3-巰基異丁酸酯)、丁二醇雙(3-巰基異丁酸酯)、己二硫醇、癸二硫醇、1,4-二甲基巰基苯、丁二醇雙硫代丙酸酯、丁二醇雙巰基乙酸酯、乙二醇雙巰基乙酸酯、三羥甲基丙烷三巰基乙酸酯、丁二醇雙硫代丙酸酯、三羥甲基丙烷三硫代丙酸酯、三羥甲基丙烷三巰基乙酸酯、季戊四醇四硫代丙酸酯、季戊四醇四巰基乙酸酯、三硫代丙酸三羥基乙酯、二乙基-9-氧硫𠮿、二異丙基-9-氧硫𠮿、下述化合物No.C1、三巰基丙酸三(2-羥基乙基)異氰尿酸酯等脂肪族多官能硫醇化合物、昭和電工公司製造之Karenz MT BD1、PE1、NR1等。
作為上述溶劑,通常可使用可使上述各成分(聚合起始劑(A)及聚合性化合物(B)等)溶解或分散之溶劑例如甲基乙基酮、甲基戊基酮、二乙基酮、丙酮、甲基異丙基酮、甲基異丁基酮、環己酮、2-庚酮等酮類;乙醚、二㗁烷、四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、二丙二醇二甲醚等醚系溶劑;乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸異丙酯、乙酸正丁酯、乙酸環己酯、乳酸乙酯、琥珀酸二甲酯、TEXANOL等酯系溶劑;乙二醇單甲醚、乙二醇單乙醚等溶纖劑系溶劑;甲醇、乙醇、異或正丙醇、異或正丁醇、戊醇等醇系溶劑;乙二醇乙酸單甲酯、乙二醇乙酸單乙酯、丙二醇-1-單甲醚-2-乙酸酯、二丙二醇單甲醚乙酸酯、乙酸3-甲氧基丁酯、丙酸乙氧基乙酯等醚酯系溶劑;苯、甲苯、二甲苯等BTX系溶劑;己烷、庚烷、辛烷、環己烷等脂肪族烴系溶劑;松節油、D-檸檬烯、蒎烯等萜烯系烴油;礦油精、Swazol#310(Cosmo Matsuyama Oil股份有限公司)、Solvesso#100(Exxon Chemical股份有限公司)等烷烴系溶劑;四氯化碳、氯仿、三氯乙烯、二氯甲烷、1,2-二氯乙烷等鹵化脂肪族烴系溶劑;氯苯等鹵化芳香族烴系溶劑;卡必醇系溶劑;苯胺;三乙基胺;吡啶;乙酸;乙腈;二硫化碳;N,N-二甲基甲醯胺;N,N-二甲基乙醯胺;N-甲基吡咯啶酮;二甲基亞碸;水等,該等溶劑可使用一種或製成兩種以上之混合溶劑而使用。
該等之中,就鹼性顯影性、圖案化性、製膜性、溶解性之方面而言,可較佳地使用酮類或醚酯系溶劑,尤其是丙二醇-1-單甲醚-2-乙酸酯(以下,稱為「PGMEA」)或環己酮。
於本發明之聚合性組合物中,溶劑之含量並無特別限制,只要為各成分均勻地分散或溶解,又,本發明之聚合性組合物呈現適於各用途之液狀或糊狀之量即可,通常,本發明之聚合性組合物中之固形物成分(溶劑以外之全部成分)之量較佳為於成為10~90質量%之範圍內含有溶劑。
又,本發明之聚合性組合物藉由使用有機聚合物,亦可改善硬化物之特性。作為該有機聚合物,例如可列舉:聚苯乙烯、聚甲基丙烯酸甲酯、甲基丙烯酸甲酯-丙烯酸乙酯共聚物、聚(甲基)丙烯酸、苯乙烯-(甲基)丙烯酸共聚物、(甲基)丙烯酸-甲基丙烯酸甲酯共聚物、乙烯-氯乙烯共聚物、乙烯-乙烯系共聚物、聚氯乙烯樹脂、ABS(Acrylonitrile-Butadiene-Styrene,丙烯腈-丁二烯-苯乙烯)樹脂、尼龍6、尼龍66、尼龍12、胺基甲酸酯樹脂、聚碳酸酯聚乙烯丁醛、纖維素酯、聚丙烯醯胺、飽和聚酯、酚樹脂、苯氧基樹脂等。
於使用上述有機聚合物之情形時,其使用量相對於聚合性化合物(B)為100質量份,較佳為10~500質量份。
於本發明之聚合性組合物中可進而併用界面活性劑、矽烷偶合劑、三聚氰胺化合物等。
作為上述界面活性劑,可使用全氟烷基磷酸酯、全氟烷基羧酸鹽等氟系界面活性劑;高級脂肪酸鹼鹽、烷基磺酸鹽、烷基硫酸鹽等陰離子系界面活性劑;高級胺鹵酸鹽、四級銨鹽等陽離子系界面活性劑;聚乙二醇烷基醚、聚乙二醇脂肪酸酯、山梨醇酐脂肪酸酯、脂肪酸單甘油酯等非離子界面活性劑;兩性界面活性劑;聚矽氧系界面活性劑等界面活性劑,該等亦可組合而使用。
作為上述矽烷偶合劑,例如可使用信越化學公司製造之矽烷偶合劑,其中,可適宜地使用KBE-9007、KBM-502、KBE-403等具有異氰酸酯基、甲基丙烯醯基或環氧基之矽烷偶合劑。
作為上述三聚氰胺化合物,可列舉:(聚)羥甲基三聚氰胺、(聚)羥甲基甘脲、(聚)羥甲基苯并胍胺、(聚)羥甲基脲等氮化合物中之活性羥甲基(CH2
OH基)之全部或一部分(至少2個)經烷基醚化之化合物等。
此處,作為構成烷基醚之烷基,可列舉:甲基、乙基或丁基,相互可相同亦可不同。又,未經烷基醚化之羥甲基可於一分子內進行自縮合,亦可於二分子間進行縮合,其結果形成低聚物成分。
具體而言,可使用六甲氧基甲基三聚氰胺、六丁氧基甲基三聚氰胺、四甲氧基甲基甘脲、四丁氧基甲基甘脲等。
該等之中,就於溶劑中之溶解性、不易自聚合性組合物析出結晶之方面而言,較佳為六甲氧基甲基三聚氰胺、六丁氧基甲基三聚氰胺等經烷基醚化之三聚氰胺。
於本發明之聚合性組合物中,聚合起始劑(A)及聚合性化合物(B)以外之任意成分(其中,無機化合物、色材、及溶劑除外)之使用量係視其使用目的而適當加以選擇,並無特別限制,較佳為相對於聚合性化合物(B)100質量份設為合計50質量份以下。
本發明之聚合性組合物可照射能量線而製成硬化物。該硬化物形成為與用途相應之適當之形狀。例如於形成膜狀之硬化物之情形時,本發明之聚合性組合物可藉由旋轉塗佈機、輥式塗佈機、棒式塗佈機、模嘴塗佈機、簾幕式塗佈機、各種印刷、浸漬等公知之方法,應用於鈉玻璃、石英玻璃、半導體基板、金屬、紙、塑膠等支持基體上。又,亦可於暫時施加於膜等支持基體上後,轉印於其他支持基體上,其應用方法並無限制。
作為使本發明之聚合性組合物硬化時所使用之能量線之光源,可利用超高壓水銀燈、高壓水銀燈、中壓水銀燈、低壓水銀燈、水銀蒸汽電弧燈、氙弧燈、碳弧燈、金屬鹵化物燈、螢光燈、鎢燈、準分子燈、殺菌燈、發光二極體、由CRT(Cathode-Ray Tube,陰極射線管)光源等獲得之具有2000埃~7000埃之波長之電磁波能量或電子束、X射線、輻射等高能量線,較佳為使用發出波長300~450 nm之光之超高壓水銀燈、水銀蒸汽電弧燈、碳弧燈、氙弧燈等。
進而,藉由曝光之光源使用雷射光,不使用遮罩,利用電腦等之數位資訊直接形成圖像之雷射直接繪圖法不僅可實現生產性,亦可實現解像性或位置精度等之提高,故而較有用,作為其雷射光,適宜地使用340~430 nm之波長之光,亦可使用準分子雷射、氮雷射、氬離子雷射、氦鎘雷射、氦氖雷射、氪離子雷射、各種半導體雷射及YAG(Yttrium Aluminum Garnet,釔鋁石榴石)雷射等發出可見至紅外區域之光者。於使用該等雷射光之情形時,較佳為添加吸收可見至紅外之該區域之增感色素。
又,本發明之聚合性組合物之硬化通常必須於上述能量線之照射後進行加熱,就硬化率之方面而言,較佳為40~150℃左右之加熱。
本發明之聚合性組合物可用於光硬化性塗料或清漆;光硬化性接著劑;金屬用塗佈劑;印刷基板;彩色電視、PC(Personal Computer,個人電腦)監視器、攜帶型資訊終端、數位相機等彩色顯示之液晶顯示元件中之彩色濾光片;CCD(Charge Coupled Device,電荷耦合元件)影像感測器之彩色濾光片;電漿顯示面板用之電極材料;粉末塗層;印刷油墨;印刷版;接著劑;牙科用組合物;凝膠塗層;電子工程用之光阻;電鍍抗蝕劑;蝕刻阻劑;乾膜;焊料抗蝕劑;用以製造各種顯示用途用之彩色濾光片或用以於電漿顯示面板、電發光顯示裝置、及LCD(Liquid Crystal Display,液晶顯示器)之製造步驟中形成該等之構造之抗蝕劑;用以封入電氣及電子零件之組合物;阻焊劑;磁記錄材料;微小機械零件;波導;光開關;鍍覆用遮罩;蝕刻遮罩;彩色試驗系統;玻璃纖維纜線塗層;網版印刷用模板;用以利用立體光刻製造三維物體之材料;全像術記錄用材料;圖像記錄材料;微細電子電路;脫色材料;用於圖像記錄材料之脫色材料;使用微膠囊之圖像記錄材料用之脫色材料;印刷配線板用光阻材料;UV(Ultra Violet,紫外線)及可見雷射直接圖像系統用之光阻材料;於印刷電路基板之依序積層中之介電體層形成中所使用之光阻材料或保護膜等各種用途,其用途並無特別限制。
本發明之聚合性組合物亦可基於形成液晶顯示面板用間隔件之目的及形成垂直配向型液晶顯示元件用突起之目的而使用。尤其是作為用以同時形成垂直配向型液晶顯示元件用之突起與間隔件之感光性樹脂組合物而較有用。
上述液晶顯示面板用間隔件係藉由如下步驟而較佳地形成:(I)於基板上形成本發明之聚合性組合物之塗膜之步驟;(2)介隔具有特定之圖案形狀之遮罩對該塗膜照射能量線(光)之步驟;(3)曝光後之烘烤步驟;(4)將曝光後之覆膜顯影之步驟;(5)對顯影後之該覆膜進行加熱之步驟。
添加有色材之本發明之聚合性組合物可適宜地用作構成彩色濾光片之RGB(Red Green Blue,紅綠藍)等各像素之抗蝕劑、或形成各像素之間隔壁之黑矩陣用抗蝕劑。進而,於添加撥油墨劑之黑矩陣用抗蝕劑之情形時,可較佳地用於齒廓角(profile angle)為50°以上之噴墨方式彩色濾光片用間隔壁。作為該撥油墨劑,可適宜地使用氟系界面活性劑及含有氟系界面活性劑之組合物。
於用於上述噴墨方式彩色濾光片用間隔壁之情形時,藉由如下方法製造光學元件,該方法係由本發明之聚合性組合物形成之間隔壁在被轉印體上進行劃分,並藉由噴墨法向所劃分之被轉印體上之凹部賦予液滴而形成圖像區域。此時,較佳為上述液滴含有著色劑,而將上述圖像區域著色,於該情形時,藉由上述製造方法製作之光學元件成為於基板上至少具有包含複數個著色區域之像素群、及將該像素群之各著色區域分隔開之間隔壁者。
本發明之聚合性組合物亦可用作保護膜或絕緣膜用組合物。於該情形時,可含有紫外線吸收劑、烷基化改性三聚氰胺及/或丙烯酸改性三聚氰胺、分子中含有醇性羥基之1或2官能之(甲基)丙烯酸酯單體及/或二氧化矽溶膠。
上述絕緣膜可用於在可剝離之支持基材上設置有絕緣樹脂層之積層體中之該絕緣樹脂層,該積層體係可利用鹼性水溶液進行顯影者,絕緣樹脂層之膜厚較佳為10~100 μm。
本發明之聚合性組合物藉由含有無機化合物,可用作感光性漿料組合物。該感光性漿料組合物可用以形成電漿顯示器面板之間隔壁圖案、介電體圖案、電極圖案及黑矩陣圖案等焙燒物圖案。
[實施例]
以下,列舉實施例及比較例更詳細地說明本發明,但本發明並不限定於該等實施例等。再者,以下所獲得之化合物之性狀係於大氣壓下、25℃下者。
[製造例1]肟化合物1之合成
向100 mL四口燒瓶中添加氯化鋁2.40 g、及二氯乙烷(EDC)34.56 g,並於冰浴上於-5℃下進行攪拌。向其中滴下添加使9,9'-二己基茀5.02 g及辛醯氯2.44 g溶解於二氯乙烷20 g中而成之溶液。升溫至室溫後攪拌3小時,再次利用冰浴冷卻,並滴加5質量%氫氧化鈉水溶液20 g。進行油水分離,利用水將有機層水洗3次。利用蒸發器將有機層減壓濃縮,而以產量6.91 g獲得下述酮化合物1。
向100 mL四口燒瓶中依序添加酮化合物1 3.00 g、鹽酸羥胺0.50 g、二甲基甲醯胺(DMF)9.30 g、及吡啶0.62 g,並於油浴上於80℃下加熱攪拌5小時。冷卻至室溫後,添加至離子水50 g中。添加乙酸乙酯進行油水分離,利用水將有機層水洗3次。利用蒸發器將有機層減壓濃縮,而以產量3.10 g獲得下述肟化合物1。
[製造例2]肟化合物2之合成
向100 mL四口燒瓶中依序添加酮化合物1 2.00 g、DMF6.39 g、及35質量%鹽酸0.45 g,並於冰浴上於5℃下進行攪拌。向其中滴下添加亞硝酸異丁酯0.50 g。於升溫至室溫後,攪拌6小時。其後添加至離子水50 g中。添加乙酸乙酯進行油水分離,利用水將有機層水洗3次。利用蒸發器將有機層減壓濃縮,而以產量2.13 g獲得下述肟化合物2。
[製造例3]肟化合物3之合成
向100 mL四口燒瓶中依序添加下述酮化合物2 3.63 g、鹽酸羥胺1.67 g、DMF11.78 g、及吡啶1.90 g,並於油浴上於80℃下加熱攪拌5小時。於冷卻至室溫後,添加至離子水50 g中。添加乙酸乙酯進行油水分離,利用水將有機層水洗3次。利用蒸發器將有機層減壓濃縮。向殘渣中添加甲醇進行晶析,而以產量3.13 g獲得下述肟化合物3。
[製造例4]肟化合物4之合成
向100 ml四口燒瓶中添加1-(9,9-二甲基-7-(2-甲基苯甲醯基)-9H-茀-2-基)辛烷-1-酮1.0 eq.,並溶解於二甲基甲醯胺(理論產量之400重量%)中。向溶液中添加羥基氯化銨1.2 eq.及吡啶1.2 eq.。於55℃下將反應混合物加熱攪拌9小時,添加離子交換水,並利用乙酸乙酯進行萃取。依序利用5質量%鹽酸、離子交換水、飽和碳酸氫鈉水溶液將有機層洗淨2次,利用離子交換水洗淨3次,利用硫酸鎂使之乾燥,而進行濃縮。藉由矽膠管柱層析法(溶離劑=乙酸乙酯:己烷=1:6)對殘渣進行精製,而以產率70%獲得肟化合物4。
[製造例4]肟化合物5之合成
向100 ml四口燒瓶中添加3-環戊基-1-(9,9-二甲基-7-硝基-9H-茀-2-基)丙烷-1-酮1.0 eq.,使之溶解於二甲基甲醯胺(理論產量之400重量%)中。向溶液中添加羥基氯化銨1.2 eq.及吡啶1.2 eq.。將反應混合物於55℃下加熱攪拌7小時,添加離子交換水,並利用乙酸乙酯進行萃取。利用離子交換水將有機層洗淨3次,利用硫酸鎂使之乾燥,而進行濃縮。向其中添加甲醇(理論產量之1700重量%)進行晶析,而以淡褐色粉狀化合物之形式以產率65%獲得肟化合物5。
[實施例1-1]化合物No.1之合成
向100 mL四口燒瓶中添加肟化合物1 1.00 g、及乙腈6.00 g,於室溫下進行攪拌。歷時10分鐘向其中添加使1,1'-羰基二咪唑0.41 g分散於乙腈5 g中所得之溶液。攪拌3小時後,去除析出之結晶,而將濾液濃縮。進而進行減壓乾燥3小時,以產率59%獲得白色粉狀化合物。對所獲得之固體之TG-DTA(Thermogravimetric-Differential Thermal Analysis,熱重-示差熱分析)(熔點/℃)、1
H-NMR(Nuclear Magnetic Resonance,核磁共振)進行分析,確認為作為目標物之化合物No.1。將分析結果示於[表1]及[表2]。
[實施例1-2]化合物No.2之合成
向100 mL四口燒瓶中添加肟化合物2 2.13 g、及乙腈29.00 g,於室溫下進行攪拌。歷時10分鐘向其中添加使1,1'-羰基二咪唑0.86 g分散於乙腈5 g中所得之溶液。攪拌1小時後,去除析出之結晶,而將濾液濃縮。進而進行減壓乾燥4小時,以產率51%獲得白色粉狀化合物。對所獲得之固體之TG-DTA(熔點/℃)、1
H-NMR進行分析,確認為作為目標物之化合物No.2。將分析結果示於[表1]及[表2]。
[實施例1-3]化合物No.3之合成
向100 mL四口燒瓶中添加肟化合物3 1.18 g、1,1'-羰基二咪唑1.17 g及四氫呋喃(THF)1.04 g,於室溫下攪拌2小時。向其中滴下添加哌啶0.61 g,並於油浴上於60℃下攪拌6小時。冷卻至室溫後,利用蒸發器進行減壓溶劑餾去,向殘渣中添加氯仿,利用離子交換水進行5次水洗。將有機層減壓濃縮,並添加甲醇進行晶析,而以產率74%獲得淡黃色粉狀物。對所獲得之固體之TG-DTA(熔點/℃)、1
H-NMR進行分析,確認為作為目標物之化合物No.3。將分析結果示於[表1]及[表2]。
[實施例1-4]化合物No.50之合成
向100 ml四口燒瓶中添加肟化合物4 1.0 eq.、二氯乙烷(理論產量之600重量%)、及三乙基胺2.0 eq.,並於冰浴上於5℃下進行攪拌。向其中滴下添加使氯甲酸4-硝基苯酯1.5 eq.溶解於二氯乙烷中所得者。滴加結束後,於室溫下攪拌1小時。再次於冰浴上冷卻至5℃後,滴下添加苯胺1.5 eq.。於室溫下攪拌1小時,進行減壓溶劑餾去。向其中添加乙酸乙酯與離子交換水,進行油水分離。進而利用1質量%氫氧化鈉水溶液將有機層洗淨2次,利用離子交換水洗淨2次,利用硫酸鎂使之乾燥,而進行濃縮。藉由矽膠管柱層析法(溶離劑=乙酸乙酯:甲苯=1:30)對殘渣進行精製,而以淡黃色透明固體之形式以產率56%獲得化合物No.50。對所獲得之化合物之TG-DTA(熔點)、1
H-NMR進行分析。將結果示於[表2A]及[表2B]。化合物No.50之合成反應式如下所述。
[實施例1-5]化合物No.51之合成
向100 ml四口燒瓶中添加肟化合物4 1.0 eq.、二氯乙烷(理論產量之600重量%)、及三乙基胺2.0 eq.,並於冰浴上於5℃下進行攪拌。向其中滴下添加使氯甲酸4-硝基苯酯1.5 eq.溶解於二氯乙烷中所得者。滴加結束後,於室溫下攪拌1小時。再次於冰浴上冷卻至5℃後,滴下添加哌啶1.5 eq.。於室溫下攪拌1小時,進行減壓溶劑餾去。向其中添加乙酸乙酯與離子交換水,進行油水分離。進而將有機層利用1質量%氫氧化鈉水溶液洗淨2次,利用離子交換水洗淨3次,利用硫酸鎂使之乾燥,而進行濃縮。藉由矽膠管柱層析法(溶離劑=乙酸乙酯:甲苯=1:10)對殘渣進行精製,而以淡黃色透明液體之形式以產率67%獲得化合物No.51。對所獲得之化合物之TG-DTA(熔點)、1
H-NMR進行分析。將結果示於[表2B]。化合物No.51之合成反應式如下所述。
[實施例1-6]化合物No.52之合成
向100 ml四口燒瓶中添加肟化合物5 1.0 eq.、二氯乙烷(理論產量之600重量%)、及三乙基胺2.0 eq.,並於冰浴上於5℃下進行攪拌。向其中滴下添加使氯甲酸4-硝基苯酯1.5 eq.溶解於二氯乙烷中所得者。滴加結束後,於室溫下攪拌1小時。再次於冰浴上冷卻至5℃後,滴下添加二丁基胺1.5 eq.。於室溫下攪拌1小時,進行減壓溶劑餾去。向其中添加乙酸乙酯與離子交換水,進行油水分離。進而將有機層利用1質量%氫氧化鈉水溶液洗淨2次,利用離子交換水洗淨3次,利用硫酸鎂使之乾燥,而進行濃縮。向其中添加甲醇(理論產量之600重量%)進行晶析,而以淡棕色固體之形式以產率78%獲得化合物No.52。對所獲得之化合物之TG-DTA(熔點)、1
H-NMR進行分析。將結果示於[表2A]及[表2B]。化合物No.52之合成反應式如下所述。
[實施例1-7]化合物No.53之合成
向100 ml四口燒瓶中添加肟化合物5 1.0 eq.、二氯乙烷(理論產量之600重量%)、及三乙基胺2.0 eq.,並於冰浴上於5℃下進行攪拌。向其中滴下添加使氯甲酸4-硝基苯酯1.5 eq.溶解於二氯乙烷中所得者。滴加結束後,於室溫下攪拌1小時。再次於冰浴上冷卻至5℃後,滴下添加3,5-二甲基哌啶1.5 eq.。於室溫下攪拌1小時,進行減壓溶劑餾去。向其中添加乙酸乙酯與離子交換水,進行油水分離。進而將有機層利用離子交換水洗淨3次,利用硫酸鎂使之乾燥,而進行濃縮。向其中添加乙醇(理論產量之7000重量%)進行晶析,而以淡黃色固體之形式以產率79%獲得化合物No.53。對所獲得之化合物之TG-DTA(熔點)、1
H-NMR進行分析。將結果示於[表2A]及[表2B]。化合物No.53之合成反應式如下所述。
[實施例1-8]化合物No.54之合成
向100 ml四口燒瓶中添加肟化合物4 1.0 eq.、及乙腈(理論產量之200重量%),於室溫下進行攪拌。向其中添加1,1'-羰基二咪唑1.1 eq.,於室溫下攪拌30分鐘,進行減壓溶劑餾去。藉由矽膠管柱層析法(溶離劑=乙酸乙酯:己烷=60:40)進行精製,而以淡黃色固體之形式以產率44%獲得化合物No.54。對所獲得之化合物之TG-DTA(熔點)、1
H-NMR進行分析。將結果示於[表2A]及[表2B]。化合物No.54之合成反應式如下所述。
[評價1]溶劑溶解性試驗
量取上述化合物No.1~No.3及比較化合物No.1 1.0 g,向其中於室溫(25℃)下添加下述[表3]所示之各溶劑,測定完全溶解時之溶劑之添加量,並藉由下述計算式算出化合物之溶解性。將結果示於[表3]。
化合物於各溶劑中之溶解性(%)=1.0 g/(1.0 g+溶劑之添加量g)×100
根據[表3]明確,本發明之化合物與比較化合物相比,對於各溶劑之溶解度較高。
[實施例2-1~2-3及比較例2-1]聚合性組合物之製備
進行[表4]中所記載之調配,獲得作為聚合性組合物之實施例2-1~2-3及比較例2-1之聚合性組合物。[表4]中之各成分之符號表示下述成分。
A-1 化合物No.1
A-2 化合物No.2
A-3 化合物No.3
A'-1 比較化合物No.1
B-1 EPPN-201
(苯酚酚醛清漆型環氧樹脂、環氧當量193 g/eq.、日本化藥公司製造)
B-2 TRR-5010G
(甲酚酚醛清漆型酚樹脂、羥基當量120 g/eq.、Mw=8,000、旭有機材工業公司製造)
C-1 FZ-2122
(聚醚改性聚矽氧烷、Dow Corning Toray公司製造)
D-1 環戊酮(溶劑)
[評價2]聚合性組合物及硬化物之評價
對上述中所獲得之實施例2-1~2-3及比較例2-1之聚合性組合物,以下述順序進行線寬感度、硬化物之殘膜率之評價。將結果一併記載於[表5]。
[評價樣品之製作方法及評價方法]
將實施例2-1~2-3及比較例2-1之聚合性組合物(各組合物之塗佈量約2.0 cc)分別利用旋轉塗佈機(500 rpm×2秒→1800 rpm×15秒→傾斜×5秒)於玻璃基材上形成塗膜,於加熱板上進行預烘烤(90℃×120秒)。
其後,使用TOPCON曝光機對紫外光進行分割曝光(60、120 mJ/cm2
、間隙:20 μm、照度:20.0 mW/cm2
)。
曝光後,於加熱板上進行後烘烤(120℃×5分鐘)後,利用PGMEA(溫度:23℃)進行顯影:200 rpm×10秒→IPA(異丙醇)洗淨(200 rpm×10秒→乾燥:500 rpm×5秒)。
對所獲得之樣品,測定各曝光量下之遮罩開口20 μm之圖案之線寬、殘膜率。
如[表5]所示,本發明之聚合性組合物與比較聚合性組合物相比,顯示出較大之線寬(高感度)、較高之殘膜率(硬化性較高)。由此明確本發明之化合物作為聚合起始劑而較優異。
[評價3]光分解性試驗(實施例3-1~3-3、比較例3-1)
將上述化合物No.1~No.3及比較化合物No.1製備為1.0×10-4
mol濃度之乙腈溶液,並放入至附蓋之石英池中。分別對該等樣品於100 mJ/cm2
、500 mJ/cm2
及1000 mJ/cm2
(365 nm下之累計光量)之條件下照射將超高壓水銀燈作為光源之光,並調查分解性。分解性之評價係使用HPLC(High Pressure Liquid Chromatograph,高效液相層析儀)測定源自該化合物之光未照射時之峰面積與光照射後之峰面積,並根據下述計算式計算分解率。將所獲得之分解率記載於下述[表6]中。
分解率(%)=[(光未照射時之HPLC面積)-(光照射後之HPLC面積)]/(光未照射時之HPLC面積)×100
根據[表6]之結果明確,本發明之化合物與比較化合物相比分解率較高,感度優異。
Claims (17)
- 一種胺甲醯肟化合物,其係由下述式(I)所表示: 式中,R1 及R2 分別獨立地表示氫原子、碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基, R3 、R4 、R5 、R6 、R7 、R8 、R9 及R10 分別獨立地表示氫原子、氰基、硝基、-OR11 、-COOR11 、-CO-R11 、-SR11 、鹵素原子、碳原子數1~20之脂肪族烴基、碳原子數6~20之芳香族烴基、碳原子數2~20之含有雜環之基或下述式(II)所表示之基, R11 表示碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基, R1 、R2 、R3 、R4 、R5 、R6 、R7 、R8 、R9 、R10 及R11 所表示之基中之氫原子之1個或2個以上存在經鹵素原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯醚基、巰基、異氰酸酯基或碳原子數2~20之含有雜環之基取代之情形, R3 、R4 、R5 、R6 、R7 、R8 、R9 及R10 中之1個以上為下述式(II)所表示之基; 式中,R21 表示氫原子、氰基、鹵素原子、硝基、碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基, X1 為-NR22 R23 、下述式(a)或下述式(b)所表示之基, R22 及R23 分別獨立地為氫原子、碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基,或者 R22 與R23 相互連結而成為包含氮原子及碳原子之環、或包含氧原子、氮原子及碳原子之環, R21 、R22 及R23 所表示之基中之氫原子之1個或2個以上存在經鹵素原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯醚基、巰基、異氰酸酯基或碳原子數2~20之含有雜環之基取代之情形, n表示0或1,*表示鍵結鍵; 式中,R31 、R32 、R33 、R34 、R35 、R36 、R37 、R38 、R39 及R40 分別獨立地為氫原子、碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基,或者 存在R31 與R32 、R33 與R34 、R35 與R36 、R37 與R38 及R39 與R40 相互連結而形成包含氮原子及碳原子之環、或包含氧原子、氮原子及碳原子之環之情形, R31 、R32 、R33 、R34 、R35 、R36 、R37 、R38 、R39 及R40 所表示之基中之氫原子之1個或2個以上存在經鹵素原子、硝基、氰基、羥基、胺基、羧基、甲基丙烯醯基、丙烯醯基、環氧基、乙烯基、乙烯醚基、巰基、異氰酸酯基或碳原子數2~20之含有雜環之基取代之情形, *表示鍵結鍵。
- 如請求項1之胺甲醯肟化合物,其中上述式(I)中之X1 表示-NR22 R23 ,且 R22 及R23 分別獨立地為碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基,或者 R22 為氫原子,R23 為碳原子數1~20之脂肪族烴基或碳原子數6~20之芳香族烴基,或者 R22 與R23 相互連結而形成包含氮原子及碳原子之環、或包含氧原子、氮原子及碳原子之環。
- 如請求項1之胺甲醯肟化合物,其中上述式(I)中之X1 表示-NR22 R23 ,且 R22 與R23 相互連結而形成包含氮原子及碳原子之環。
- 如請求項1之胺甲醯肟化合物,其中上述式(I)中之X1 表示-NR22 R23 ,且 R22 與R23 分別獨立地為碳原子數1~20之脂肪族烴基。
- 如請求項1之胺甲醯肟化合物,其中上述式(I)中之X1 表示-NR22 R23 ,且 R22 為氫原子,R23 為碳原子數6~20之芳香族烴基。
- 如請求項1之胺甲醯肟化合物,其中上述式(I)中之R3 、R4 、R5 、R6 、R7 、R8 、R9 及R10 中之2個以上為上述式(II)所表示之基。
- 如請求項1之胺甲醯肟化合物,其中上述式(I)中之R3 、R4 、R5 及R6 中之1個為上述式(II)所表示之基,且R7 、R8 、R9 及R10 中之至少1個為氫原子、硝基或碳原子數6~12之芳香族烴基。
- 如請求項1之胺甲醯肟化合物,其中上述式(I)中之R3 、R4 、R5 及R6 中之1個為上述式(II)所表示之基,且R7 、R8 、R9 及R10 中之至少1個為硝基或碳原子數6~12之芳香族烴基。
- 如請求項8之胺甲醯肟化合物,其中上述式(I)中之R3 、R4 、R5 及R6 中之1個為上述式(II)所表示之基,且R7 、R8 、R9 及R10 中之1個為硝基或碳原子數6~12之芳香族烴基。
- 如請求項8之胺甲醯肟化合物,其中上述式(I)中之R9 為硝基或碳原子數6~12之芳香族烴基。
- 如請求項6之胺甲醯肟化合物,其中上述式(I)中之R4 為上述式(II)所表示之基。
- 一種潛在性鹼化合物,其包含如請求項1之胺甲醯肟化合物。
- 一種聚合起始劑,其包含至少1種之如請求項1之胺甲醯肟化合物。
- 一種聚合性組合物,其含有如請求項13之聚合起始劑(A)及聚合性化合物(B)。
- 如請求項14之聚合性組合物,其中上述聚合性化合物(B)為環氧樹脂或乙烯性不飽和化合物、或包含環氧樹脂與酚樹脂之混合物、包含環氧樹脂與硫醇化合物之混合物、或包含乙烯性不飽和化合物與硫醇化合物之混合物。
- 一種硬化物,其係如請求項14之聚合性組合物。
- 一種硬化物之製造方法,其具有對如請求項14之聚合性組合物照射能量線之步驟。
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