CN101238100A - 吲哚化合物、滤光器以及光学记录材料 - Google Patents
吲哚化合物、滤光器以及光学记录材料 Download PDFInfo
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- CN101238100A CN101238100A CNA2006800292395A CN200680029239A CN101238100A CN 101238100 A CN101238100 A CN 101238100A CN A2006800292395 A CNA2006800292395 A CN A2006800292395A CN 200680029239 A CN200680029239 A CN 200680029239A CN 101238100 A CN101238100 A CN 101238100A
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- -1 Indole compound Chemical class 0.000 title claims abstract description 169
- 230000003287 optical effect Effects 0.000 title claims description 93
- 239000000463 material Substances 0.000 title claims description 37
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title abstract description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 60
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 230000003595 spectral effect Effects 0.000 claims description 41
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 12
- 125000001118 alkylidene group Chemical group 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 8
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- 125000004429 atom Chemical group 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 2
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- 239000000126 substance Substances 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
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- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 4
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 239000007864 aqueous solution Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 125000001400 nonyl 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])[H] 0.000 description 3
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- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
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- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
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- 238000009832 plasma treatment Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
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- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
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- AZLIIAMTCHKNJJ-UHFFFAOYSA-N potassium;trifluoromethanesulfonic acid Chemical compound [K].OS(=O)(=O)C(F)(F)F AZLIIAMTCHKNJJ-UHFFFAOYSA-N 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl 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])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
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- 238000010189 synthetic method Methods 0.000 description 1
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- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
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- 150000003624 transition metals Chemical class 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及下述通式(I)表示的吲哚化合物。式中,R1和R2分别独立地表示氢原子、碳原子数为1~30的烃基或下述通式(II)表示的取代基,R3和R4分别独立地表示碳原子数为1~10的烷基、碳原子数为1~10的烷氧基或碳原子数为6~30的芳基,R5、R6、R7和R8分别独立地表示氢原子、碳原子数为1~30的烃基、卤原子、羟基、硝基、氰基、NHR或NR’R”,R、R’和R”分别独立地表示碳原子数为1~10的烷基,R’和R”可以相互连接形成环,R5和R6、R6和R7、R7和R8也可以分别相互连接形成环。Anq-表示q价的阴离子,q表示1或2,p表示使电荷保持中性的系数。
Description
技术领域
本发明涉及新型吲哚化合物、滤光器以及光学记录材料。该吲哚化合物作为光学要素等是有用的。该吲哚化合物尤其是作为在图像显示装置用的滤光器中含有的紫外线吸收剂是有用的,另外,还可用于在具有可见以及近红外区域的波长且利用低能量的激光等可进行高密度的光学记录和再生的光学记录介质中使用的光学记录材料。
背景技术
光学记录介质通常具有记录容量大、记录或再生以非接触方式进行等优点,因而广泛普及。对于WORM、CD-R、DVD-R等可刻录型光盘,是在光学记录层的微小面积上使激光聚焦,改变光学记录层的性状来进行记录,利用记录部分和未记录部分的反射光量的不同进行再生。
现在,在上述光盘中,记录和再生所使用的半导体激光的波长在CD-R中为750~830nm,在DVD-R中为620~690nm,为了进一步实现容量的增加,人们正在研究使用短波长激光的光盘,例如用380~420nm的光作为记录光的光盘。
对于短波长激光用的光学记录介质,在光学记录层的形成中,使用各种化合物。例如,专利文献1中报道的偶氮化合物,专利文献2中报道的卟啉化合物,专利文献3中报道的三唑化合物的金属络合物。但是,这些化合物作为光学记录层的形成中使用的光学记录材料,其吸收波长特性未必符合要求。
另一方面,在液晶显示装置(LCD)、等离子显示器(PDP)、电致发光显示器(ELD)、阴极射线管显示装置(CRT)、荧光显示管、场致发射型显示器等图像显示装置用的滤光器中,吸收300~390nm波长的光的化合物被用作紫外线吸收剂。
例如,在下述专利文献4中,报道了含有紫外线吸收剂、遮断200~410nm的光的有机EL显示元件用滤色器。但是,该有机EL显示元件用滤色器中使用的紫外线吸收剂作为滤光器用的紫外线吸收剂时,其吸收波长特性未必符合要求。
专利文献1:日本特开2004-209771号公报
专利文献2:日本特开2004-58365号公报
专利文献3:日本特开2004-174838号公报
专利文献4:日本特开2004-102223号公报
发明内容
因此,本发明的目的在于提供一种化合物,其具有特别适于图像显示装置用滤光器以及短波长激光用光学记录介质的光学记录材料中所使用的光学要素的光学特性。
本发明者经过反复研讨,结果发现具有亚氨基结构的特定吲哚化合物具有满足作为上述光学要素的吸收波长特性,从而完成了本发明。
本发明是基于上述发现而完成的,其提供下述通式(I)表示的吲哚化合物、含有该吲哚化合物而形成的滤光器、以及光学记录材料,其含有在基体上形成有光学记录层的光学记录介质的该光学记录层中所使用的该吲哚化合物而形成。
[化学式1]
(式中,R1和R2分别独立地表示氢原子、碳原子数为1~30的烃基或下述通式(II)表示的取代基,R3和R4分别独立地表示碳原子数为1~10的烷基、碳原子数为1~10的烷氧基或碳原子数为6~30的芳基,R5、R6、R7和R8分别独立地表示氢原子、碳原子数为1~30的烃基、卤原子、羟基、硝基、氰基、NHR或NR’R”,R、R’和R”分别独立地表示碳原子数为1~10的烷基,R’和R”可以相互连接形成环,R5和R6、R6和R7、R7和R8也可以分别相互连接形成环。Anq-表示q价的阴离子,q表示1或2,p表示使电荷保持中性的系数。)
[化学式2]
(式中,Ra~Ri各自独立地表示氢原子或碳原子数为1~6的烷基,该烷基中的亚甲基可以被-O-或-CO-取代,Z表示直接键合或可以具有取代基的碳原子数为1~8的亚烷基,该亚烷基中的亚甲基也可以被-O-、-S-、-CO-、-COO-、-OCO-、-SO2-、-NH-、-CONH-、-NHCO-、-N=CH-或-CH=CH-取代,M表示金属原子。)
具体实施方式
下面,根据优选的实施形态,详细说明本发明的吲哚化合物、含有该吲哚化合物而形成的滤光器以及光学记录材料。
首先,对本发明的吲哚化合物进行说明。
上述通式(I)表示的本发明的吲哚化合物中,作为R1、R2、R5、R6、R7和R8表示的碳原子数为1~30的烃基,可列举甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、异丁基、戊基、异戊基、叔戊基、己基、环己基、环己基甲基、2-环己基乙基、庚基、异庚基、叔庚基、正辛基、异辛基、叔辛基、2-乙基己基、壬基、异壬基、癸基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基等烷基;乙烯基、1-甲基乙烯基、2-甲基乙烯基、丙烯基、丁烯基、异丁烯基、戊烯基、己烯基、庚烯基、辛烯基、癸烯基、十五碳烯基、1-苯基丙烯-3-基等链烯基;苯基、萘基、2-甲基苯基、3-甲基苯基、4-甲基苯基、4-乙烯基苯基、3-异丙基苯基、4-异丙基苯基、4-丁基苯基、4-异丁基苯基、4-叔丁基苯基、4-己基苯基、4-环己基苯基、4-辛基苯基、4-(2-乙基己基)苯基、4-硬脂基苯基、2,3-二甲基苯基、2,4-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、2,4-二叔丁基苯基、环己基苯基等烷基芳基;苄基、苯乙基、2-苯基丙烷-2-基、二苯基甲基、三苯基甲基、苯乙烯基、肉桂基等芳基烷基等;这些基团被醚键和/或硫醚键中断后的基团,例如2-甲氧基乙基、3-甲氧基丙基、4-甲氧基丁基、2-丁氧基乙基、甲氧基乙氧基乙基、甲氧基乙氧基乙氧基乙基、3-甲氧基丁基、2-苯氧基乙基、3-苯氧基丙基、2-甲基硫代乙基、2-苯基硫代乙基等。此外,这些基团也可以被烷氧基、链烯基、硝基、氰基、卤原子等取代,当被选自烷氧基、链烯基和氰基中的1种以上的基团取代时,包含这些取代基在内的总的碳原子数最大为30。
作为上述通式(I)中R3、R4、R、R’和R”表示的碳原子数为1~10的烷基,可列举甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、异丁基、戊基、异戊基、叔戊基、己基、环己基、庚基、异庚基、叔庚基、正辛基、异辛基、叔辛基、2-乙基己基、壬基、癸基等;作为碳原子数为1~10的烷氧基,可列举甲氧基、乙氧基、异丙氧基、丙氧基、丁氧基、戊氧基、异戊氧基、己氧基、庚氧基、辛氧基、2-乙基己氧基等;作为碳原子数为6~30的芳基,可列举苯基、萘基、2-甲基苯基、3-甲基苯基、4-甲基苯基、4-乙烯基苯基、3-异丙基苯基、4-异丙基苯基、4-丁基苯基、4-异丁基苯基、4-叔丁基苯基、4-己基苯基、4-环己基苯基、4-辛基苯基、4-(2-乙基己基)苯基、4-硬脂基苯基、2,3-二甲基苯基、2,4-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、2,4-二叔丁基苯基、2,5-二叔丁基苯基、2,6-二叔丁基苯基、2,4-二叔戊基苯基、2,5-二叔戊基苯基、2,5-二叔辛基苯基、2,4-二枯基苯基、环己基苯基、联苯基、2,4,5-三甲基苯基、苄基、苯乙基、2-苯基丙烷-2-基、二苯基甲基、三苯基甲基、苯乙烯基、肉桂基等。
作为上述通式(I)中R5、R6、R7和R8表示的卤原子,可列举出氟、氯、溴、碘。
作为上述通式(I)中R’和R”连接形成的环,可列举哌啶环、哌嗪环、吡咯环、吗啉环等;作为R5和R6、R6和R7、以及R7和R8连接形成的环,可列举环丁烯环、环戊烯环、环己烯环、苯环、吡啶环等。
作为上述通式(II)中Ra~R1表示的碳原子数为1~4的烷基,可列举甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、异丁基、甲氧基、乙氧基、丙氧基、异丙氧基、甲氧基甲基、乙氧基甲基、2-甲氧基乙基、乙酰基、1-羰基乙基、乙酰基甲基、1-羰基丙基、2-氧代丁基、2-乙酰基乙基、1-羰基异丙基等;作为Z表示的可以具有取代基的碳原子数为1~8的亚烷基,可列举亚甲基、亚乙基、亚丙基、甲基亚乙基、亚丁基、1-甲基亚丙基、2-甲基亚丙基、1,2-二甲基亚丙基、1,3-二甲基亚丙基、1-甲基亚丁基、2-甲基亚丁基、3-甲基亚丁基、4-甲基亚丁基、2,4-二甲基亚丁基、1,3-二甲基亚丁基、亚戊基、亚己基、亚庚基、亚辛基、乙烷-1,1-二基、丙烷-2,2-二基、亚乙烯基、亚丙烯基、亚甲基氧基、亚乙基氧基、氧代亚甲基、硫代亚甲基、羰基亚甲基、羰基氧代亚甲基、亚甲基羰基氧基、磺酰亚甲基、氨基亚甲基、乙酰基氨基、亚乙基羧酰胺基、乙酰亚胺基等;作为M表示的金属原子,可列举铁、钴、镍、铜、锌、铝、钛、锆、钒、铌、钽、铬、钼、钨、锇、锰、钌、镓、铟、硅、锗、锡、锑、铋、金、银、钯、铑、铂、铱、钇、镧、镨、钕、鉕、钆、镝、钬、镥、钪等。
在上述通式(I)中,作为Anq-表示的阴离子,例如一价阴离子,可列举氯离子、溴离子、碘离子、氟离子等卤离子;高氯酸根离子、氯酸根离子、硫氰酸根离子、六氟化磷阴离子、六氟化锑阴离子、四氟化硼阴离子等无机类阴离子;苯磺酸根离子、甲苯磺酸根离子、三氟甲磺酸根离子、二苯基胺-4-磺酸根离子、2-氨基-4-甲基-5-氯苯磺酸根离子、2-氨基-5-硝基苯磺酸根离子等有机磺酸根离子;辛基磷酸根离子、十二烷基磷酸根离子、十八烷基磷酸根离子、苯基磷酸根离子、壬基苯基磷酸根离子、2,2’-亚甲基二(4,6-二叔丁基苯基)膦酸根离子等有机磷酸根类阴离子,双三氟甲基磺酰亚胺阴离子、双全氟丁磺酰亚胺阴离子、全氟-4-乙基环己烷磺酸根阴离子、四(五氟苯基)硼酸根离子、三(氟烷基磺酰)碳阴离子等;作为二价阴离子,例如苯二磺酸根离子、萘二磺酸根离子等。另外,根据需要,也可以使用具有使激发态下的活性分子去激发(猝灭)的功能的猝灭剂阴离子或在环戊二烯基环上具有羧基或膦酸基、磺酸基等阴离子性基团的二茂铁、二茂钌等金属茂化合物阴离子等。
作为上述猝灭剂阴离子,例如可列举出下述通式(A)、(B)或下式(C)表示的阴离子,特开昭60-234892号公报、特开平5-43814号公报、特开平5-305770号公报、特开平6-239028号公报、特开平9-309886号公报、特开平9-323478号公报、特开平10-45767号公报、特开平11-208118号公报、特开2000-168237号公报、特开2002-201373号公报、特开2002-206061号公报、特开2005-297407号公报、特公平7-96334号公报、国际公开98/29257号公报等中记载的阴离子。
[化学式3]
(式中,X表示镍原子或铜原子,R9和R10各自独立地表示卤原子、碳原子数为1~8的烷基、碳原子数为6~30的芳基或-SO2-G基,G表示烷基、可以被卤原子取代的芳基、二烷基氨基、二芳基氨基、哌啶基或吗啉基,a和b各自表示0~4。另外,R11、R12、R13和R14各自独立地表示烷基、烷基苯基、烷氧基苯基或卤代苯基。)
[化学式4]
在本发明的吲哚化合物中,上述通式(I)中R1是碳原子数为1~30的烃基、特别是碳原子数为1~8的烷基或碳原子数为6~13的芳基的吲哚化合物;R2是氢原子或碳原子数为1~30的烃基、特别是氢原子、碳原子数为1~8的烷基或碳原子数为6~13的芳基的吲哚化合物;R3是碳原子数为1~10的烷基、特别是碳原子数为1~4的烷基的吲哚化合物;R4是碳原子数为1~10的烷基、特别是碳原子数为1~4的烷基的吲哚化合物,由于它们在成本和光学特性方面优异,因而优选。
因此,作为本发明的吲哚化合物的具体例子,可以列举下述化合物No.1~24。
[化学式5]
[化学式6]
[化学式7]
对上述通式(I)表示的本发明的吲哚化合物的制造方法不特殊限制,可以通过利用了公知的一般反应的方法来得到,作为制造方法,例如在为了得到具有一价阴离子的吲哚化合物时,可列举按下述[化学式6]所示的路径进行合成的方法。
[化学式8]
(式中,R1、R2、R3、R4、R5、R6、R7、R8、X、Y1和Y2与上述通式(I)相同,Hal表示卤原子,D-表示阴离子。)
本发明的吲哚化合物可用作为通过吸收特定波长、特别是320~420nm波长的光而发挥功能的光学要素。作为光学要素的例子,可列举出滤光器中含有的紫外线吸收剂、光盘等光学记录介质的光学记录层的形成中所使用的光学记录剂等。
另外,本发明的吲哚化合物除了用作光学要素外,还可以用作医药品、农药、香料、染料等的合成中间体、或各种功能性材料等。
下面,对本发明的滤光器进行说明。
本发明的滤光器含有本发明的吲哚化合物。本发明的吲哚化合物在340~390nm有最大吸收波长,由于能够吸收410nm以下的紫外线以及一部分可见光并遮断,因此,含有本发明的吲哚化合物的本发明的滤光器适宜作为实现显示图像高品质化的图像显示装置用的滤光器。本发明的滤光器除了用于图像显示装置外,还可以用于分析装置、半导体装置的制造、天文观测、光通信、眼镜透镜等各种用途中。
本发明的滤光器通常配置在显示器的前表面。例如,本发明的滤光器可以直接贴付于显示器的表面,当在显示器之前设有前面板时,可以贴付于前面板的表侧(外侧)或里侧(显示器侧)。
作为本发明的滤光器的代表性结构,可列举在透明支撑体上根据需要设置了下涂层、反射防止层、硬涂层、润滑层等各层的结构。作为使本发明的吲哚化合物、或本发明的吲哚化合物以外的色素化合物、各种稳定剂等任选成分含有在本发明的滤光器中的方法,例如可列举出(1)在透明支撑体或任意各层中含有的方法、(2)在透明支撑体或任意各层上涂布的方法、(3)在选自透明支撑体及任意各层中的任意相邻两层之间的粘合剂层中混入的方法、(4)在各层之外另外设置含有本发明的吲哚化合物等光吸收剂等的光吸收层的方法等。
在本发明的滤光器中,本发明的吲哚化合物的使用量是:每单位面积的滤光器中,通常为1~1000mg/m2,优选为5~100mg/m2,当使用量不足1mg/m2时,无法充分发挥光吸收效果;当使用超过1000mg/m2时,滤色器的色调过强,有可能使显示品质等下降,此外,亮度也有可能下降。
关于本发明的吲哚化合物,为了使其在滤光器的单位面积中的使用量处于上述范围,通常如下地来使用。例如,当制造在粘合剂层中含有本发明的吲哚化合物的滤光器时,相对于丙烯酸系粘合剂等粘合剂100质量份,优选添加0.001~0.05质量份的本发明的吲哚化合物以及40~500质量份的甲基乙基酮等溶剂来制作清漆,将该清漆在经过易粘附处理的PET膜等透明支撑体上涂布后,使其固化,得到具有厚0.1~10微米的粘合剂层(固化膜)的滤光器。
无论采用上述(1)~(4)中的任一方法作为使本发明的吲哚化合物以及任选成分含有在本发明的滤光器中的方法,各成分的配合比例只要遵照上述配合比例即可。
作为上述透明支撑体的材料,例如可列举出玻璃等无机材料;二乙酰纤维素、三乙酰纤维素(TAC)、丙酰纤维素、丁酰纤维素、乙酰丙酰纤维素、硝酸纤维素等纤维素酯;聚酰胺;聚碳酸酯;聚对苯二甲酸乙二酯、聚萘二甲酸乙二酯、聚对苯二甲酸丁二酯、聚-1,4-环己烷二甲醇对苯二甲酸酯、聚乙二醇-1,2-二苯氧基乙烷-4,4’-二羧酸酯、聚对苯二甲酸丁二酯等聚酯;聚苯乙烯;聚乙烯、聚丙烯、聚甲基戊烯等聚烯烃;聚甲基丙烯酸甲酯等丙烯酸系树脂;聚碳酸酯;聚砜;聚醚砜;聚醚酮;聚醚酰亚胺;聚氧乙烯、降冰片烯树脂等高分子材料。透明支撑体的透射率优选为80%以上,进一步优选为86%以上。雾度优选为2%以下,进一步优选为1%以下。折射率优选为1.45~1.70。
在这些透明支撑体中,可以添加红外线吸收剂、无机微粒等,还可以对透明支撑体实施各种表面处理。
作为上述无机微粒,可列举例如层状粘土矿物、二氧化硅、二氧化钛、硫酸钡、碳酸钙等。
作为上述各种表面处理,可列举例如试剂处理、机械处理、电晕放电处理、火焰处理、紫外线照射处理、高频处理、辉光放电处理、活性等离子体处理、激光处理、混酸处理、臭氧氧化处理等。
作为上述下涂层,当设有含有光吸收剂的光吸收层时,是在透明支撑体和光吸收层之间使用的层。上述下涂层可作为含有玻璃化转变温度为-60~60℃的聚合物的层、光吸收层侧的表面为粗面的层、或含有与光吸收层的聚合物具有亲和性的聚合物的层而形成。另外,下涂层可以设在未设有光吸收层的透明支撑体的表面,用于改善透明支撑体和在其上设置的层(例如反射防止层、硬涂层)之间的粘接力,也可以用于改善使滤光器和图像显示装置粘接的粘接剂与滤光器的亲和性。下涂层的厚度优选为2nm~20μm,进一步优选为5nm~5μm,更优选为20nm~2μm,更进一步优选为50nm~1μm,最优选为80nm~300nm。含有玻璃化转变温度为-60~60℃的聚合物的下涂层,通过聚合物的粘合性,从而将透明支撑体和滤色器层粘接。玻璃化转变温度为-60~60℃的聚合物,例如可以通过氯乙烯、偏二氯乙烯、乙酸乙烯酯、丁二烯、氯丁橡胶、苯乙烯、氯丁二烯、丙烯酸酯、甲基丙烯酸酯、丙烯腈或甲基乙烯基醚的聚合或它们的共聚来得到。玻璃化转变温度优选为50℃以下,进一步优选为40℃以下,更优选为30℃以下,更进一步优选为25℃以下,最优选为20℃以下。下涂层在25℃时的弹性模量优选为1~1000MPa,更优选为5~800MPa,最优选为10~500MPa。光吸收层侧的表面为粗面的下涂层通过在粗面上形成光吸收层,从而将透明支撑体和光吸收层粘接。光吸收层侧的表面为粗面的下涂层可以通过聚合物乳胶的涂布来容易地形成。乳胶的平均粒径优选为0.02~3μm,更优选为0.05~1μm。作为与光吸收层的粘合剂聚合物具有亲和性的聚合物,可列举出丙烯酸树脂、纤维素衍生物、明胶、酪蛋白、淀粉、聚乙烯醇、可溶性尼龙以及高分子乳胶等。另外,还可以在本发明的滤光器中设置二层以上的下涂层。在下涂层中可以添加使透明支撑体溶胀的溶剂、消光剂、表面活性剂、防静电剂、涂布助剂、硬膜剂等。
在上述反射防止层中,低折射率层是必需的。低折射率层的折射率比上述透明支撑体的折射率低。低折射率层的折射率优选为1.20~1.55,更优选为1.30~1.50。低折射率层的厚度优选为50~400nm,更优选为50~200nm。低折射率层可以作为由折射率低的含氟聚合物形成的层(特开昭57-34526号、特开平3-130103号、特开平6-115023号、特开平8-313702号、特开平7-168004号各公报中记载)、通过溶胶凝胶法得到的层(特开平5-208811号、特开平6-299091号、特开平7-168003号各公报中记载)、或含有微粒的层(特公昭60-59250号、特开平5-13021号、特开平6-56478号、特开平7-92306号、特开平9-288201号各公报中记载)而形成。在含有微粒的层中,作为微粒间或微粒内的微孔,可以在低折射率层中形成空隙。含有微粒的层优选具有3~50体积%的空隙率,更优选具有5~35体积%的空隙率。
为了防止宽波长范围的反射,在上述反射防止层上,除了低折射率层外,优选还层叠折射率高的层(中、高折射率层)。高折射率层的折射率优选为1.65~2.40,更优选为1.70~2.20。中折射率层的折射率调整到低折射率层的折射率与高折射率层的折射率之间的中间值。中折射率层的折射率优选为1.50~1.90,更优选为1.55~1.70。中、高折射率层的厚度优选为5nm~100μm,更优选为10nm~10μm,最优选为30nm~1μm。中·高折射率层的雾度优选为5%以下,更优选为3%以下,最优选为1%以下。中、高折射率层可以用具有较高折射率的聚合物粘合剂来形成。作为折射率高的聚合物,可列举出聚苯乙烯、苯乙烯共聚物、聚碳酸酯、三聚氰胺树脂、酚醛树脂、环氧树脂、环状(脂环式或芳香族)异氰酸酯和多元醇反应得到的聚氨酯等。其他具有环状(芳香族、杂环式、脂环式)基的聚合物、以氟以外的卤原子为取代基的聚合物的折射率也很高。还可以使用通过导入双键使自由基固化成为可能的单体的聚合反应而形成的聚合物。
为了得到更高的折射率,也可以在上述聚合物粘合剂中分散无机微粒。无机微粒的折射率优选为1.80~2.80。无机微粒优选由金属的氧化物或硫化物来形成。作为金属的氧化物或硫化物,可列举出氧化钛(例如金红石型、金红石型/锐钛型的混晶、锐钛型、无定形结构)、氧化锡、氧化铟、氧化锌、氧化锆、硫化锌等。其中,特别优选氧化钛、氧化锡及氧化铟。无机微粒以这些金属的氧化物或硫化物为主成分,可以进一步含有其他元素。主成分意味着在构成粒子的成分中含量(重量%)最多的成分。作为其他元素,可列举Ti、Zr、Sn、Sb、Cu、Fe、Mn、Pb、Cd、As、Cr、Hg、Zn、Al、Mg、Si、P、S等。使用由于皮膜成形性而能在溶剂中分散或其本身即为液体状的无机材料、例如各种元素的醇盐、有机酸的盐、与配位性化合物结合的配位化合物(例如螯合物)、活性无机聚合物,可以形成中、高折射率层。
在上述反射防止层的表面,可以赋予防炫射功能(使入射光在表面散射,防止膜周围的景色向膜表面转移的功能)。例如,在透明膜的表面形成微细的凹凸从而在其表面形成反射防止层,或在形成反射防止层后,通过印花辊在表面形成凹凸,从而得到具有防炫射功能的反射防止层。具有防炫射功能的反射防止层一般具有3~30%的雾度。
上述硬涂层具有比上述透明支撑体的硬度更高的硬度。硬涂层优选含有交联的聚合物。硬涂层可以用丙烯酸系、氨酯系、环氧系的聚合物、低聚物或单体(例如紫外线固化型树脂)等来形成。也可以由二氧化硅系材料来形成硬涂层。
在上述反射防止层(低折射率层)的表面,还可以形成润滑层。润滑层赋予低折射率层表面以润滑性,具有改善耐损伤性的功能。润滑层可以由聚有机硅氧烷(例如硅油)、天然蜡、石油蜡、高级脂肪酸金属盐、氟系润滑剂或其衍生物等来形成。润滑层的厚度优选为2~20nm。
当除上述各层外另行设置光吸收层时,可以单独使用本发明的吲哚化合物,也可以与粘合剂一起使用。作为粘合剂,可以使用例如明胶、酪蛋白、淀粉、纤维素衍生物、藻酸等天然高分子材料,或聚甲基丙烯酸甲酯、聚乙烯醇缩丁醛、聚乙烯基吡咯烷酮、聚乙烯醇、聚氯乙烯、苯乙烯-丁二烯共聚物、聚苯乙烯、聚碳酸酯、聚酰胺、聚氨酯、聚酯、聚脲等合成高分子材料。
上述下涂层、反射防止层、硬涂层、润滑层、光吸收层等可以通过一般的涂布方法来形成。作为涂布方法,可列举浸涂法、气刀涂布法、帘涂法、辊涂法、线棒涂布法、凹版涂布法、使用料斗的挤压涂布法(美国专利第2681294号说明书记载)等。可以通过同时涂布来形成二层以上的层。关于同时涂布法,例如在美国专利第2761791号、美国专利第2941898号、美国专利第3508947号、美国专利第3526528号的各说明书以及原崎勇次著《コ一テイング工学》(《涂布工学》)253页(1973年朝仓书店发行)中有记载。
下面,对本发明的光学记录材料进行说明。
本发明的光学记录材料含有本发明的吲哚化合物,并在光学记录介质的光学记录层的形成中使用,根据含有的吲哚化合物的光吸收特性可以在各种光学记录介质中适用。在本发明的光学记录材料中,特别适用于波长为380nm~420nm的短波长激光用光盘的光学记录材料是:其含有的吲哚化合物在溶液状态时的光吸收特性中具有最大吸收波长λmax在320~420nm的范围。另外,关于吸收强度,由于λmax处的ε若小于1.0×104,则记录感度有可能下降,所以优选为1.0×104以上。关于上述吲哚化合物的溶液状态下的λmax以及ε的测定,可以按照常法,选择样品溶液的浓度、测定所使用的溶剂等来进行。
关于使用含有上述吲哚化合物的本发明的光学记录材料来形成光学记录介质的光学记录层的方法,不受特殊限制。通常,可列举出将在甲醇、乙醇等低级醇类;甲基溶纤剂、乙基溶纤剂、丁基溶纤剂、丁基二甘醇等醚醇类;丙酮、甲乙酮、甲基异丁基酮、环己酮、二丙酮醇等酮类;乙酸乙酯、乙酸丁酯、乙酸甲氧基乙酯等酯类;丙烯酸乙酯、丙烯酸丁酯等丙烯酸酯类;2,2,3,3-四氟丙醇等氟化醇类;苯、甲苯、二甲苯等烃类;二氯甲烷、二氯乙烷、氯仿等氯化烃类等的有机溶剂中溶解了本发明的吲哚化合物以及各种化合物的溶液在基体上通过旋转涂布、喷雾、浸渍等进行涂布的湿式涂布法、蒸镀法、溅射法等。
上述光学记录层以薄膜的形式而形成,其厚度通常以0.001~10μm为宜,优选为0.01~5μm的范围。
另外,在本发明的光学记录材料中的本发明的吲哚化合物的含量优选为:在本发明的光学记录材料中所含有的固体成分中,为10~100质量%。上述光学记录层优选形成为:在光学记录层中含有50~100质量%的上述通式(I)表示的吲哚化合物。为了形成含有上述含量的上述吲哚化合物的光学记录层,以本发明的光学记录材料中所含有的固体成分为基准,本发明的光学记录材料进一步优选含有50~100质量%的上述通式(I)表示的吲哚化合物。
本发明的光学记录材料中,除本发明的吲哚化合物外,根据需要,还可以含有花菁系化合物、偶氮系化合物、酞菁系化合物、氧杂菁系化合物、方形酸内鎓盐(squarylium)系化合物、苯乙烯系化合物、卟吩系化合物、甘菊环鎓盐(azulenium)系化合物、克酮酸次甲基(croconicmethine)系化合物、吡喃鎓系化合物、硫代吡喃鎓系化合物、三芳基甲烷系化合物、二苯基甲烷系化合物、四氢胆碱系化合物、靛酚系化合物、蒽醌系化合物、萘醌系化合物、呫吨系化合物、噻嗪系化合物、吖啶系化合物、噁嗪系化合物、螺吡喃系化合物、芴系化合物、若丹明系化合物等可在普通光学记录层中使用的化合物;聚乙烯、聚酯、聚苯乙烯、聚碳酸酯等树脂类;表面活性剂;抗静电剂;滑剂;阻燃剂;受阻胺等自由基捕获剂;二茂铁衍生物等凹坑(pit)形成促进剂;分散剂;抗氧剂;交联剂;耐光性赋予剂等。此外,本发明的光学记录材料还可以含有芳香族亚硝基化合物、胺鎓盐化合物、亚胺鎓盐化合物、二亚胺鎓盐化合物、过渡金属螯合物等作为单线态氧等的猝灭剂,也可以使用猝灭剂阴离子。在本发明的光学记录材料中,上述各种化合物在本发明的光学记录材料中所含有的固体成分中优选以0~50质量%范围的量使用。
设有上述光学记录层的上述基体的材质,只要是对于写入(记录)光和读取(再生)光为实质上透明的材质即可,没有特殊限制,例如,可以使用聚甲基丙烯酸甲酯、聚对苯二甲酸乙二酯、聚碳酸酯等树脂、玻璃等。另外,根据用途,其形状可以使用胶带、圆筒、皮带、圆盘等任意的形状。
另外,在上述光学记录层上,可以用金、银、铝、铜等,通过蒸镀法或溅射法来形成反射膜,也可以用丙烯酸树脂、紫外线固化性树脂等来形成保护层。
实施例
下面,用实施例和比较例更详细地说明本发明。但是,本发明不受以下实施例等的任何限制。
[实施例1]化合物No.1的合成
在氮置换后的反应烧瓶中,装入二甲基甲酰胺(DMF)10ml和氯仿80ml,在冰冷却下滴加氧氯化磷6.91g(45.1mmol),在冰冷却下搅拌1小时。在冰冷却下滴加1-甲基吲哚3.94g(30.0mmol)溶于氯仿40ml而形成的溶液,加热回流3小时。冷却至室温,将反应液缓慢滴加至六氟化磷酸钾23.1g(126mmol)的400ml水溶液中,室温下搅拌2小时。滤出析出物,用甲醇200ml在室温下搅拌30分钟,进行洗涤。经过过滤、干燥,得到粉红色固体9.32g(收率93.4%)。证实:得到的粉红色固体是目标物质即化合物No.1。得到的化合物No.1的分析结果如下所示。
(1)1H-NMR(ppm、DMSO溶剂)
3.57(s;3H)、3.74(s;3H)、4.01(s;3H)、7.39-7.50(m;2H)、7.26-7.65(m;1H)、8.00-8.10(m;1H)、8.70(s;1H)、9.12(s;1H)
(2)IR吸收(cm-1)
3168、1647、1536、1466、1402、1349、1256、1113、838、758
(3)UV吸收测定(丙酮溶剂)
λmax;345.0nm、ε;1.86×104(浓度6.68×10-6mol/l)
(4)分解温度(TG-DTA:100ml/分钟氮气流中、升温10℃/分钟)
295.8℃;熔点、326.7℃;质量减少起始点
[实施例2]化合物No.2的合成
在氮置换后的反应烧瓶中,装入DMF10ml和氯仿80ml,在冰冷却下滴加氧氯化磷6.90g(45.0mmol),在冰冷却下搅拌1小时。在冰冷却下滴加1-甲基-2-苯基吲哚6.22g(30.0mmol)溶于氯仿40ml而形成的溶液,加热回流3小时。冷却至室温,将反应液缓慢滴加至六氟化磷酸钾20.0g(109mmol)的400ml水溶液中,在室温下搅拌30分钟。除去水层,加水400ml,在室温下搅拌30分钟后,滤出析出物,用甲醇150ml在室温下搅拌30分钟,进行洗涤。经过过滤、干燥,得到灰白色固体。由乙腈/乙醇混合溶剂进行重结晶,得到灰白色固体5.06g(收率41.5%)。证实:得到的灰白色固体是目标物质即化合物No.2。得到的化合物No.2的分析结果如下所示。
(1)1H-NMR(ppm、DMSO溶剂)
3.53(s;3H)、3.68(s;3H)、3.82(s;3H)、7.45-7.55(m;2H)、7.58-7.75(m;5H)、7.83(d;1H、J=7.8Hz)、7.88(d;1H、J=7.6Hz)、8.51(s;1H)
(2)IR吸收(cm-1)
3430、1656、1490、1474、1463、1391、1120、842、795、754、705
(3)UV吸收测定(丙酮溶剂)
λmax;348.5nm、ε;1.74×104(浓度1.93×10-6mol/l)
(4)分解温度(TG-DTA:100ml/分钟氮气流中、升温10℃/分钟)
162.6℃;熔点、332.9℃;质量减少起始点
[实施例3]化合物No.3的合成
在氮置换后的反应烧瓶中,在冰冷却下装入N,N-二正丁基甲酰胺15g(95.4mmol)和氧氯化磷5.21g(34.0mmol),在冰冷却下搅拌1小时。在冰冷却下加入1-甲基吲哚2.62g(20.0mmol),在100℃下搅拌3小时。冷却至室温,馏去N,N-二正丁基甲酰胺后,加入六氟化磷酸钾15.3g(95.4mmol),混合均匀。加水150ml,在室温下搅拌30分钟后,滤出析出物,用甲醇100ml在室温下搅拌30分钟,进一步加水50ml,在室温下搅拌30分钟进行洗涤。经过过滤、干燥,得到土黄色固体。由乙腈/甲醇混合溶剂进行重结晶,经过过滤、干燥,得到浅粉色固体2.90g(收率34.8%)。证实:得到的浅粉色固体是目标物质即化合物No.3。得到的化合物No.3的分析结果如下所示。
(1)1H-NMR(ppm、DMSO溶剂)
0.96(t;3H;J=7.3Hz)、0.97(t;3H;J=7.3Hz)、1.36(tq;2H;J=7.6、7.3Hz)、1.52(tq;2H;J=7.8、7.6Hz)、1.70-1.89(m;4)、3.85-3.99(m;4)、4.05(s;3H)、7.45(dd;1H、J=6.6、3.9Hz)、7.46(dd;1H、J=6.6、3.7Hz)、7.68-7.80(m;1H)、8.08-8.20(m;1H)、8.56(s;1H)、9.08(s;1H)
(2)IR吸收(cm-1)
2955、2874、1639、1532、1476、1352、1256、1114、834、751
(3)UV吸收测定(氯仿溶剂)
λmax;357.0nm、ε;2.04×104(浓度5.64×10-6mol/l)
(4)分解温度(TG-DTA:100ml/分钟氮气流中、升温10℃/分钟)
179.7℃;熔点、307.8℃;质量减少起始点
[实施例4]化合物No.4的合成
在氮置换后的反应烧瓶中,在冰冷却下装入N,N-二正丁基甲酰胺15g(95.4mmol)和氧氯化磷5.21g(34.0mmol),在冰冷却下搅拌1小时。在冰冷却下加入1-甲基吲哚6.22g(30.0mmol),在100℃下搅拌4小时。冷却至室温,馏去N,N-二正丁基甲酰胺后,加入三氟甲磺酸钾25.0g(132mmol),混合均匀。加水150ml,在室温下进行30分钟超声波照射后,滤出析出物。由乙醇/二乙基醚混合溶剂进行重结晶,经过过滤、干燥,得到浅黄色固体4.64g(收率55.1%)。证实:得到的浅黄色固体是目标物质即化合物No.4。得到的化合物No.4的分析结果如下所示。
(1)1H-NMR(ppm、DMSO溶剂)
0.94(t;3H;J=6.6Hz)、0.96(t;3H;J=7.1Hz)、1.35(tq;2H;J=7.6、7.6Hz)、1.51(tq;2H;J=7.6、7.6Hz)、1.70-1.85(m;4H)、3.85-3.95(m;4H)、4.05(s;3H)、7.35-7.50(m;2H)、7.65-7.80(m;1H)、8.05-8.20(m;1H)、8.58(s;1H)、9.09(s;1H)
(2)IR吸收(cm-1)
2960、2874、1624、1588、1476、1464、1430、1265、1153、1032、965
(3)UV吸收测定(氯仿溶剂)
λmax;356.5nm、ε;1.84×104(浓度9.89×10-6mol/l)
(4)分解温度(TG-DTA:100ml/分钟氮气流中、升温10℃/分钟)
110.3℃;熔点、287.1℃;质量减少起始点
[实施例5]
在氮置换后的反应烧瓶中,在冰冷却下装入N,N-二正丁基甲酰胺22.5g(143mmol)和氧氯化磷7.82g(51.0mmol),在冰冷却下搅拌1小时。在冰冷却下加入1-(3,5-双(三氟甲基)苯基)吲哚6.08g(18.4mmol),在100℃下搅拌4小时。冷却至室温,馏去N,N-二正丁基甲酰胺后,加入六氟化磷酸钾50.0g(272mmol),混合均匀。加水1L,在室温下搅拌30分钟后,除去水层,用乙醇1L搅拌30分钟进行洗涤后,滤出析出物。由丙酮/乙醇混合溶剂进行重结晶,经过过滤、干燥,得到无色透明针状结晶2.75g(收率24.3%)。证实:得到的无色透明针状结晶是目标物质即化合物No.5。得到的化合物No.5的分析结果如下所示。
(1)1H-NMR(ppm、DMSO溶剂)
0.96(t;3H;J=7.6Hz)、0.99(t;3H;J=7.1Hz)、1.40(tq;2H;J=7.3、7.1Hz)、1.48(tq;2H;J=7.6、7.6Hz)、1.78-1.95(m;4H)、4.05(t;2H;J=7.6Hz)、4.11(t;2H;J=7.8Hz)、7.51(dd;1H;J=8.5、7.1Hz)、7.55(dd;1H;J=7.8、7.1Hz)、7.64(d;1H;J=8.3Hz)、8.26(d;1H;J=7.6Hz)、8.41(s;1H)、8.60(s;2H)、8.83(s;1H)、9.34(s;1H)
(2)IR吸收(cm-1)
2967、2880、1646、1522、1475、1360、1282、1230、1192、1146、843、825、762
(3)UV吸收测定(氯仿溶剂)
λmax;354.5nm、ε;1.92×104(浓度6.87×10-6mol/l)
(4)分解温度(TG-DTA:100ml/分钟氮气流中、升温10℃/分钟)
183.3℃;熔点、297.5℃;质量减少起始点
[实施例6]化合物No.6的合成
在氮置换后的反应烧瓶中,在冰冷却下装入N,N-二正丁基甲酰胺22.5g(143mmol)和氧氯化磷7.82g(51.0mmol),在冰冷却下搅拌1小时。在冰冷却下加入1-甲基-2-苯基吲哚6.22g(30.0mmol),在100℃下搅拌4小时。冷却至室温,馏去N,N-二正丁基甲酰胺后,加入六氟化磷酸钾50.0g(272mmol),混合均匀。加水1L,在室温下搅拌30分钟进行洗涤后,滤出析出物。由丙酮/乙醇混合溶剂进行重结晶,经过过滤、干燥,得到浅绿色固体3.02g(收率20.4%)。证实:得到的浅绿色固体是目标物质即化合物No.6。得到的化合物No.6的分析结果如下所示。
(1)1H-NMR(ppm、DMSO溶剂)
0.80(t;3H;J=7.3Hz)、0.90(t;3H;J=7.3Hz)、1.20(tq;2H;J=7.6、7.6Hz)、1.30(tq;2H;J=7.6、7.6Hz)、1.65-1.79(m;4H)、3.82(s;3H)、3.89(t;2H;J=6.8Hz)、3.91(t;2H;J=6.8Hz)、7.49(dd;1H;J=7.2、7.2Hz)、7.53(dd;1H;J=7.1、7.1Hz)、7.57-7.63(m;2H)、7.64-7.77(m;3H)、7.80(d;1H;J=7.8Hz)、7.85(d;1H;J=7.8Hz)、8.54(s;1H)
(2)IR吸收(cm-1)
2960、2935、2874、1651、1477、1464、1404、1368、1086、838、802、750
(3)UV吸收测定(氯仿溶剂)
λmax;352.5nm、ε;2.48×104(浓度4.07×10-6mol/l)
(4)分解温度(TG-DTA:100ml/分钟氮气流中、升温10℃/分钟)
100.4℃;熔点、304.9℃;质量减少起始点
[实施例7]化合物No.21的合成
在氮置换后的反应烧瓶中,在冰冷却下装入N,N-二正丁基甲酰胺10ml、氯仿80ml和氧氯化磷6.74g(44.0mmol),在冰冷却下搅拌1小时。在冰冷却下加入1-丙基二茂铁基吲哚10.5g(29.3mmol)的氯仿40ml溶液,加热回流3.5小时。冷却至室温,缓慢滴加至六氟化磷酸钾23.5g(127mmol)的水500ml水溶液,在室温下搅拌1小时。滤出析出物,经过过滤、干燥,得到茶褐色固体16.2g(收率99.4%)。证实:得到的茶褐色固体是目标物质即化合物No.21。得到的化合物No.21的分析结果如下所示。
(1)1H-NMR(ppm、DMSO溶剂)
1.48(dt;2H;J=7.3、7.3Hz)、1.90(dt;2H;J=7.3、7.3Hz)、2.32(t;2H;J=7.6Hz)、3.61(s;3H)、3.74(s;3H)、4.03(s;5H)、3.98-4.05(m;4H)、4.44(t;2H、J=7.3Hz)、7.35-7.50(m;2H)、7.81(d;1H;J=7.1Hz)、8.08(d;1H;J=6.8Hz)、8.76(s;1H)、9.17(s;1H)
(2)IR吸收(cm-1)
1654、1530、1404、1364、1105、836
(3)UV吸收测定(氯仿溶剂)
λmax;353.0nm、ε;2.10×104(浓度1.59×10-5mol/l)
(4)分解温度(TG-DTA:100ml/分钟氮气流中、升温10℃/分钟)
200.5℃;熔点、284.7℃;质量减少起始点
[实施例8]化合物No.24的合成
在氮置换后的反应烧瓶中,在冰冷却下装入N,N-二正丁基甲酰胺43.6g(277mmol)和氧氯化磷13.3g(87.1mmol),在冰冷却下搅拌1小时。在冰冷却下加入5-溴-1-甲基吲哚12.2g(58.0mmol),在100℃下搅拌4小时。冷却至室温,馏去N,N-二正丁基甲酰胺后,加入六氟化磷酸钾58.0g(315mmol),混合均匀。加水1L,在室温下搅拌30分钟进行洗涤后,滤出析出物。由丙酮/甲醇混合溶剂进行重结晶,经过过滤、干燥,得到浅黄色固体18.9g(收率65.8%)。证实:得到的浅黄色固体是目标物质即化合物No.24。得到的化合物No.24的分析结果如下所示。
(1)1H-NMR(ppm、DMSO溶剂)
0.95(t;3H;J=7.3Hz)、0.96(t;3H;J=7.3Hz)、1.36(tq;2H;J=7.3、7.8Hz)、1.50(tq;2H;J=7.6、7.8Hz)、1.72-1.87(m;4H)、3.91(t;4H;J=7.1Hz)、4.04(s;3H)、7.59(dd;1H;J=1.7、8.8Hz)、7.71(d;1H;J=8.8Hz)、8.41(d;1H;J=1.7Hz)、8.58(s;1H)、9.11(s;1H)
(2)IR吸收(cm-1)
2964、1638、1530、1449、1353、1253、1123、838
(3)UV吸收测定(氯仿溶剂)
λmax;354.0nm、ε;2.14×104(浓度1.01×10-5mol/l)
(4)分解温度(TG-DTA:100ml/分钟氮气流中、升温10℃/分钟)
161.7℃;熔点、313.8℃;质量减少起始点
[实施例9]化合物No.23的合成
将2.06g(4.18mmol)的由实施例8中得到的化合物No.24溶解于丙酮20ml中,滴加将化学式[C]所示的阴离子的三乙胺盐5.0mmol溶于丙酮162ml而形成的溶液,加热回流3小时。冷却至室温后,将反应物缓慢滴加至水800ml中,在室温下搅拌14小时。滤出析出的固体,用丙酮洗涤后,使其干燥,得到红褐色固体4.18g(收率93.7%)。证实:得到的红褐色固体是目标物质即化合物No.23。得到的化合物No.23的分析结果如下所示。
(1)1H-NMR(ppm、DMSO溶剂)
0.95(t;6H;J=7.1Hz)、1.01(t;12H;J=7.1Hz)、1.36(tq;2H;J=7.3、7.3Hz)、1.48(tq;2H;J=7.3、7.3Hz)、1.72-1.85(m;4H)、3.29(q;8H;J=6.8Hz)、3.89(t;4H;J=7.6Hz)、4.00(s;3H)、5.74(d;2H;J=2.4Hz)、6.35(dd;2H;J=2.7、9.5Hz)、6.55(d;2H;J=9.3Hz)、7.58(dd;1H;J=1.7、8.8Hz)、7.64(d;2H;J=9.3Hz)、7.69(d;1H;J=8.8Hz)、7.84(dd;2H;J=2.9、9.3Hz)、8.39(d;1H;J=1.7Hz)、8.54(s;1H)、9.00(d;2H;J=2.9Hz)、9.08(s;1H)
(2)IR吸收(cm-1)
2975、1611、1578、1459、1320、1283、1262、1141
(3)UV吸收测定(氯仿溶剂)
λmax;357.5nm、ε;3.95×104
541.5nm、ε;6.20×104(浓度2.18×10-6mol/l)
(4)分解温度(TG-DTA:100ml/分钟氮气流中、升温10℃/分钟)
216.8℃;熔点、258.9℃;质量减少起始点
[实施例10]含有粘合剂层的滤光器的制造
按下述配方制作UV清漆,在经过易粘附处理的188μm厚的PET膜上,将该UV清漆用棒布涂器#9涂布后,在100℃下干燥10分钟。然后,用带有红外线阻挡膜滤色器的高压汞灯照射紫外线100mJ,得到在PET膜上具有固化膜厚约为5微米的膜层(粘合剂层)的滤光器。用日本分光(株)制的紫外可见近红外分光光度计V-570对该滤光器进行测定,结果是λmax为353nm。
(配方)
化合物No.4 2.0mg
丙烯酸系粘合剂(DB5541:ダイヤボンド社制) 20g
甲乙酮 80g
[实施例11]滤光器的制造
按下述配方制作UV清漆,在经过易粘附处理的188μm厚的PET膜上,将该UV清漆用棒涂布器#9涂布后,在100℃下干燥10分钟。然后,用带有红外线阻挡膜滤色器的高压汞灯照射紫外线100mJ,得到在PET膜上具有固化膜厚约为5微米的膜层的滤光器。用日本分光(株)制的紫外可见近红外分光光度计V-570对该滤光器进行测定,结果是λmax为354nm。
(配方)
ADEKA OPTOMER KRX-571-65 100g
(旭电化工业社制UV固化树脂、树脂成分80重量%)
化合物No.5 2.0mg
甲乙酮 60g
[实施例12]光学记录材料以及光学记录介质的制造和光学记录介质的评价
将由上述制造例4中得到的化合物No.4溶解于2,2,3,3-四氟丙醇中并使化合物No.4的浓度为1.0质量%,得到作为2,2,3,3-四氟丙醇溶液的光学记录材料。在将钛螯合物(T-50:日本曹达公司制)涂布、水解而设有底层(0.01μm)的直径为12cm的聚碳酸酯圆盘基板上,将上述光学记录材料通过旋转涂布法涂布以形成厚100nm的光学记录层,从而得到光学记录介质。对该光学记录介质,测定了薄膜的吸收UV光谱和入射角为5°的反射光的UV光谱,结果是:吸收λmax为353nm,反射光λmax为382nm。
可确认:使用了本发明的吲哚化合物的滤色器在特定波长(340~390nm)具有最大吸收(实施例10和11),适宜作为滤光器用紫外线吸收剂。
另外,具有用含有本发明的吲哚化合物的光学记录材料形成的光学记录层的光学记录介质在特定波长(340~390nm)具有反射光的最大吸收(实施例12)。在以光盘为代表的光学记录介质的再生模式中,对于使激光反射在光学记录介质上而形成的反射光,根据激光波长的光量之差来检测记录的有无,因此,在反射光的吸收光谱中,越靠近激光的波长处的吸收强度越大的光学记录介质为优选。因此,含有本发明的吲哚化合物的本发明的光学记录材料,适宜作为在短波长激光用光盘等使用405nm激光的光学记录介质的光学记录层的形成中使用的光学记录材料。
[评价例1-1~1-5和比较评价例1-1]上述通式(I)表示的化合物的耐光性评价
对实施例7~9中得到的化合物No.21、No.23和No.24以及比较化合物1进行耐光性评价。
首先,在2,2,3,3-四氟丙醇中溶解本发明的化合物并使其为1质量%,调制2,2,3,3-四氟丙醇溶液,将得到的溶液在20×20mm的聚碳酸酯板上通过旋转涂布法以2000rpm、60秒进行涂布来制作试验片。关于评价,对该试验片照射55000勒克斯的光,分别照射24小时、150小时后,通过测定照射前的UV吸收光谱的λmax处的吸光度残留率来进行评价。另外,在[表1]中,作为并用物,将下述[化学式8]所示的二亚胺鎓盐化合物或二硫酚化合物溶解在2,2,3,3-四氟丙醇溶液中并使其为0.1质量%。结果如[表1]所示。
[表1]
[化学式9]
[化学式10]
由[表1]可知,本发明的上述通式(I)表示的化合物,即使照射150小时后,吸光度残留率也很高,在与二亚胺鎓盐化合物或二硫酚化合物并用的情况下,照射150小时后也未发现吸光度残留率下降。另一方面,比较化合物在照射24小时后,发现吸光度残留率下降,而且在照射150小时后,吸光度残留率显著下降。
本发明可以提供适于作为光学要素的新型吲哚化合物。另外,使用该吲哚化合物的滤光器适宜作为图像显示装置用滤光器,含有该吲哚化合物而形成的光学记录材料适用于光学记录介质的光学记录层的形成中。
权利要求书(按照条约第19条的修改)
1. (删除)
2. (删除)
3. (修正后)滤光器,其含有下述通式(I)表示的吲哚化合物而形成,
式中,R1和R2分别独立地表示氢原子、碳原子数为1~30的烃基或下述通式(II)表示的取代基,R3和R4分别独立地表示碳原子数为1~10的烷基、碳原子数为1~10的烷氧基或碳原子数为6~30的芳基,R5、R6、R7和R8分别独立地表示氢原子、碳原子数为1~30的烃基、卤原子、羟基、硝基、氰基、NHR或NR’R”,R、R’和R”分别独立地表示碳原子数为1~10的烷基,R’和R”可以相互连接形成环,R5和R6、R6和R7、R7和R8也可以分别相互连接形成环;Anq-表示q价的阴离子,q表示1或2,p表示使电荷保持中性的系数;
式中,Ra~Ri各自独立地表示氢原子或碳原子数为1~4的烷基,该烷基中的亚甲基可以被-O-或-CO-取代,Z表示直接键合或可以具有取代基的碳原子数为1~8的亚烷基,该亚烷基中的亚甲基也可以被-O-、-S-、-CO-、-COO-、-OCO-、-SO2-、-NH-、-CONH-、-NHCO-、-N=CH-或-CH=CH-取代,M表示金属原子。
4. 根据权利要求3所述的滤光器,其用于图像显示装置。
5. (修正后)光学记录材料,其用于在基体上形成有光学记录层的光学记录介质的该光学记录层中,并含有下述通式(I)表示的吲哚化合物而形成,
式中,R1和R2分别独立地表示氢原子、碳原子数为1~30的烃基或下述通式(II)表示的取代基,R3和R4分别独立地表示碳原子数为1~10的烷基、碳原子数为1~10的烷氧基或碳原子数为6~30的芳基,R5、R6、R7和R8分别独立地表示氢原子、碳原子数为1~30的烃基、卤原子、羟基、硝基、氰基、NHR或NR’R”,R、R’和R”分别独立地表示碳原子数为1~10的烷基,R’和R”可以相互连接形成环,R5和R6、R6和R7、R7和R8也可以分别相互连接形成环;Anq-表示q价的阴离子,q表示1或2,p表示使电荷保持中性的系数;
式中,Ra~Ri各自独立地表示氢原子或碳原子数为1~4的烷基,该烷基中的亚甲基可以被-O-或-CO-取代,Z表示直接键合或可以具有取代基的碳原子数为1~8的亚烷基,该亚烷基中的亚甲基也可以被-O-、-S-、-CO-、-COO-、-OCO-、-SO2-、-NH-、-CONH-、-NHCO-、-N=CH-或-CH=CH-取代,M表示金属原子。
6. (追加)根据权利要求3或4所述的滤光器或根据权利要求5所述的光学记录材料,其中,在所述通式(I)中,R1是碳原子数为1~30的烃基,R2是氢原子或碳原子数为1~30的烃基,R3是碳原子数为1~10的烷基,R4是碳原子数为1~10的烷基。
Claims (5)
1. 下述通式(I)表示的吲哚化合物,
式中,R1和R2分别独立地表示氢原子、碳原子数为1~30的烃基或下述通式(II)表示的取代基,R3和R4分别独立地表示碳原子数为1~10的烷基、碳原子数为1~10的烷氧基或碳原子数为6~30的芳基,R5、R6、R7和R8分别独立地表示氢原子、碳原子数为1~30的烃基、卤原子、羟基、硝基、氰基、NHR或NR’R”,R、R’和R”分别独立地表示碳原子数为1~10的烷基,R’和R”可以相互连接形成环,R5和R6、R6和R7、R7和R8也可以分别相互连接形成环;Anq-表示q价的阴离子,q表示1或2,p表示使电荷保持中性的系数;
式中,Ra~Ri各自独立地表示氢原子或碳原子数为1~4的烷基,该烷基中的亚甲基可以被-O-或-CO-取代,Z表示直接键合或可以具有取代基的碳原子数为1~8的亚烷基,该亚烷基中的亚甲基也可以被-O-、-S-、-CO-、-COO-、-OCO-、-SO2-、-NH-、-CONH-、-NHCO-、-N=CH-或-CH=CH-取代,M表示金属原子。
2. 根据权利要求1所述的吲哚化合物,其中,在所述通式(I)中,R1是碳原子数为1~30的烃基,R2是氢原子或碳原子数为1~30的烃基,R3是碳原子数为1~10的烷基,R4是碳原子数为1~10的烷基。
3. 一种滤光器,其含有权利要求1或2所述的吲哚化合物而形成。
4. 根据权利要求3所述的滤光器,其用于图像显示装置。
5. 一种光学记录材料,其用于在基体上形成有光学记录层的光学记录介质的该光学记录层中,且含有权利要求1或2所述的吲哚化合物而形成。
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CN102959435A (zh) * | 2010-06-25 | 2013-03-06 | 旭硝子株式会社 | 光学薄膜及其制造方法 |
CN112566949A (zh) * | 2018-08-09 | 2021-03-26 | 住友化学株式会社 | 树脂及粘合剂组合物 |
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US2941898A (en) | 1957-12-16 | 1960-06-21 | Ilford Ltd | Production of multilayer photographic materials |
GB1159598A (en) | 1965-10-28 | 1969-07-30 | Fuji Photo Film Co Ltd | Multiple Coating Process and Apparatus |
US3508947A (en) | 1968-06-03 | 1970-04-28 | Eastman Kodak Co | Method for simultaneously applying a plurality of coated layers by forming a stable multilayer free-falling vertical curtain |
US6558768B2 (en) * | 2000-03-07 | 2003-05-06 | Ricoh Company, Ltd. | Optical recording medium and optical recording and reading method using the same |
JP4183918B2 (ja) * | 2001-02-14 | 2008-11-19 | 株式会社リコー | 光記録媒体及びこれを用いる光記録方法 |
JP4145529B2 (ja) | 2002-02-15 | 2008-09-03 | 三菱化学株式会社 | 光学記録媒体及び記録方法 |
TW589349B (en) * | 2002-04-19 | 2004-06-01 | Ind Tech Res Inst | New indolestyryl compounds and its use for a high density optical recording medium |
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JP2004058365A (ja) | 2002-07-26 | 2004-02-26 | Matsushita Electric Ind Co Ltd | 光記録媒体および製造方法 |
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KR20080042810A (ko) | 2008-05-15 |
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US7923091B2 (en) | 2011-04-12 |
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