TW201533216A - 有機電致發光元件 - Google Patents
有機電致發光元件 Download PDFInfo
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- TW201533216A TW201533216A TW103139398A TW103139398A TW201533216A TW 201533216 A TW201533216 A TW 201533216A TW 103139398 A TW103139398 A TW 103139398A TW 103139398 A TW103139398 A TW 103139398A TW 201533216 A TW201533216 A TW 201533216A
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- bis
- organic
- methyl
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- 229920000642 polymer Polymers 0.000 claims abstract description 66
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 58
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 238000000149 argon plasma sintering Methods 0.000 claims abstract description 30
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims description 58
- 239000002245 particle Substances 0.000 claims description 42
- 238000005401 electroluminescence Methods 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical group O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
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- 229910052760 oxygen Inorganic materials 0.000 claims description 8
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- 238000000605 extraction Methods 0.000 claims description 7
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- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 claims description 4
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 claims description 4
- 238000009792 diffusion process Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 14
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 16
- 229910000420 cerium oxide Inorganic materials 0.000 description 15
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 15
- 239000007822 coupling agent Substances 0.000 description 14
- 229910052707 ruthenium Inorganic materials 0.000 description 14
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 13
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- 229910052787 antimony Inorganic materials 0.000 description 11
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 11
- 229910052797 bismuth Inorganic materials 0.000 description 11
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 11
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
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- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
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- 125000001424 substituent group Chemical group 0.000 description 4
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- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
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- 239000000194 fatty acid Substances 0.000 description 3
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-N zinc;quinolin-8-ol Chemical compound [Zn+2].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Abstract
例如,具備使包含如下述式所示之含有三嗪環之聚合物、交聯劑、與光擴散劑之光散射膜形成用組成物硬化而得之光散射膜的有機電致發光元件,其電流效率優良。
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Description
本發明係關於具備光散射膜之有機電致發光元件。
至今為止已進行各種將高分子化合物高機能化的嘗試。例如,作為將高分子化合物高折射率化之方法,係進行了導入芳香族環、鹵素原子、硫原子之嘗試。其中尤以導入了硫原子之環硫化物高分子化合物及硫代胺基甲酸酯高分子化合物,作為眼鏡用高折射率透鏡已被實用化。
又,作為可達成高分子化合物之進一步高折射率化之最有力的方法,已知有使用無機金屬氧化物之方法。
例如,已報告使用混合矽氧烷聚合物、與分散有氧化鋯或氧化鈦等之微粒子分散材料而成之混成材料,來提高折射率之方法(專利文獻1)。
進一步地,亦報告了於矽氧烷聚合物之一部分,導入高折射率之縮合環狀骨架的方法(專利文獻2)。
又,亦進行了多數之用以對高分子化合物賦予耐熱性之嘗試,具體而言,藉由導入芳香族環,可提高高分子化合物之耐熱性,係已廣為人知。例如,報告了主鏈具有取代伸芳基重複單位之聚伸芳基共聚物(專利文獻3),該高分子化合物主要被期待對耐熱性塑膠之應用。
另一方面,三聚氰胺樹脂,係作為三嗪系之樹脂而廣為人知,但分解溫度遠低於石墨等之耐熱性材料。
至今為止,作為由碳及氮所成之耐熱性有機材料,主要使用芳香族聚醯亞胺或芳香族聚醯胺,但此等之材料因具有直鏈構造,故耐熱溫度並不那麼高。
又,作為具有耐熱性之含氮高分子材料,亦報告有三嗪系縮合材料(專利文獻4)。
而近年來,在開發液晶顯示器、有機電致發光(EL)顯示器、光半導體(LED)元件、固體攝影元件、有機薄膜太陽電池、色素增感太陽電池、及有機薄膜電晶體(TFT)等之電子裝置時,係變得要求高機能的高分子材料。
所要求的具體特性,可列舉1)耐熱性、2)透明性、3)高折射率、4)高溶解性、5)低體積收縮率等。
鑑於此點,本發明者等人,已發現了含有具有三嗪環及芳香環之重複單位的超分支狀聚合物,具有高折射率,聚合物單獨即可達成高耐熱性、高透明性、高折射率、高溶解性、低體積收縮,適合作為製作電子裝置時
的膜形成用組成物(專利文獻5),但將由該組成物所製作之硬化膜應用於有機EL元件或發光二極體之光提取層時,係要求光提取效率(電流效率)之進一步提高。
[專利文獻1]日本特開2007-246877號公報
[專利文獻2]日本特開2008-24832號公報
[專利文獻3]美國專利第5886130號說明書
[專利文獻4]日本特開2000-53659號公報
[專利文獻5]國際公開第2010/128661號
本發明係有鑑於上述實情而為者,其目的為提供具備含有超分支狀聚合物的硬化膜,且電流效率良好的有機電致發光元件(以下亦有稱為有機EL元件者),該超分支狀聚合物係含有具有三嗪環及芳香環之重複單位。
本發明者等人為了達成上述目的重複努力探討的結果,發現具備使含有特定之含有三嗪環之聚合物、
交聯劑、與光擴散劑之光散射膜形成用組成物硬化而得的光散射膜之有機EL元件的電流效率優良,完成了本發明。
亦即,本發明提供1.一種有機電致發光元件,其特徵為具備光散射膜,該光散射膜係使含有包含下述式(1)表示之重複單位構造之含有三嗪環之聚合物、交聯劑、與光擴散劑之光散射膜形成用組成物硬化而得,
{式中,R及R’係互相獨立地表示氫原子、烷基、烷氧基、芳基、或芳烷基,Ar係表示選自由式(2)~(13)所示之群的至少1種。
本發明中所用之光散射膜形成用組成物,為含有特定之含有三嗪環之聚合物、交聯劑及光擴散劑者,因此可有效率地製作光擴散性良好的硬化膜。
所得之硬化膜,可適合利用作為製作液晶顯示器、有機EL元件(有機EL顯示器或有機EL照明)、光半導體(LED)元件、固體攝影元件、有機薄膜太陽電池、色素增感太陽電池、有機薄膜電晶體(TFT)等電子裝置時的其一構件,特別地,因為光擴散性優良,故可適合利用作為有機EL元件或LED元件之光散射層(光提取層)用材料。
[圖1]係合成例1中所得之高分子化合物[3]的1H-NMR光譜圖。
[圖2]係顯示合成例1中所得之高分子化合物[3]之TG-DTA測定結果的圖。
以下進一步詳細說明本發明。
本發明之有機EL元件,係具備使光散射膜形成用組成物硬化而得之光散射膜者,該光散射膜形成用組成物係含有包含下述式(1)表示之重複單位構造的含有三嗪環之聚合物、交聯劑、與光擴散劑。
上述式中,R及R’係互相獨立地表示氫原子、烷基、烷氧基、芳基、或芳烷基。
本發明中,烷基之碳數並無特殊限定,較佳為1~20,考慮到更加提高聚合物之耐熱性時,更佳為碳數1~10、又更佳為1~3。又,其構造可為鏈狀、分支狀、環狀之任意者。
烷基之具體例子,可列舉甲基、乙基、n-丙基、異丙基、環丙基、n-丁基、異丁基、s-丁基、t-丁基、環丁基、1-甲基-環丙基、2-甲基-環丙基、n-戊基、1-甲基-n-丁基、2-甲基-n-丁基、3-甲基-n-丁基、1,1-二甲基-n-丙基、1,2-二甲基-n-丙基、2,2-二甲基-n-丙基、1-乙基-n-丙基、環戊基、1-甲基-環丁基、2-甲基-環丁基、3-甲基-環丁基、1,2-二甲基-環丙基、2,3-二甲基-環丙基、1-乙基-環丙基、2-乙基-環丙基、n-己基、1-甲基-n-戊基、2-甲基-n-戊基、3-甲基-n-戊基、4-甲基-n-戊基、1,1-
二甲基-n-丁基、1,2-二甲基-n-丁基、1,3-二甲基-n-丁基、2,2-二甲基-n-丁基、2,3-二甲基-n-丁基、3,3-二甲基-n-丁基、1-乙基-n-丁基、2-乙基-n-丁基、1,1,2-三甲基-n-丙基、1,2,2-三甲基-n-丙基、1-乙基-1-甲基-n-丙基、1-乙基-2-甲基-n-丙基、環己基、1-甲基-環戊基、2-甲基-環戊基、3-甲基-環戊基、1-乙基-環丁基、2-乙基-環丁基、3-乙基-環丁基、1,2-二甲基-環丁基、1,3-二甲基-環丁基、2,2-二甲基-環丁基、2,3-二甲基-環丁基、2,4-二甲基-環丁基、3,3-二甲基-環丁基、1-n-丙基-環丙基、2-n-丙基-環丙基、1-異丙基-環丙基、2-異丙基-環丙基、1,2,2-三甲基-環丙基、1,2,3-三甲基-環丙基、2,2,3-三甲基-環丙基、1-乙基-2-甲基-環丙基、2-乙基-1-甲基-環丙基、2-乙基-2-甲基-環丙基、2-乙基-3-甲基-環丙基等。
上述烷氧基之碳數並無特殊限定,較佳為1~20,考慮到更加提高聚合物之耐熱性時,更佳為碳數1~10、又更佳為1~3。又,其烷基部分之構造,可為鏈狀、分支狀、環狀之任意者。
烷氧基之具體例子,可列舉甲氧基、乙氧基、n-丙氧基、異丙氧基、n-丁氧基、異丁氧基、s-丁氧基、t-丁氧基、n-戊氧基、1-甲基-n-丁氧基、2-甲基-n-丁氧基、3-甲基-n-丁氧基、1,1-二甲基-n-丙氧基、1,2-二甲基-n-丙氧基、2,2-二甲基-n-丙氧基、1-乙基-n-丙氧基、n-己氧基、1-甲基-n-戊氧基、2-甲基-n-戊氧基、3-甲基-n-戊氧基、4-甲基-n-戊氧基、1,1-二甲基-n-丁氧基、1,2-二
甲基-n-丁氧基、1,3-二甲基-n-丁氧基、2,2-二甲基-n-丁氧基、2,3-二甲基-n-丁氧基、3,3-二甲基-n-丁氧基、1-乙基-n-丁氧基、2-乙基-n-丁氧基、1,1,2-三甲基-n-丙氧基、1,2,2-三甲基-n-丙氧基、1-乙基-1-甲基-n-丙氧基、1-乙基-2-甲基-n-丙氧基等。
上述芳基之碳數,並無特殊限定,較佳為6~40,考慮到更加提高聚合物之耐熱性時,更佳為碳數6~16、又更佳為6~13。
芳基之具體例子,可列舉苯基、o-氯苯基、m-氯苯基、p-氯苯基、o-氟苯基、p-氟苯基、o-甲氧基苯基、p-甲氧基苯基、p-硝基苯基、p-氰基苯基、α-萘基、β-萘基、o-聯苯基、m-聯苯基、p-聯苯基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基等。
芳烷基之碳數,並無特殊限定,較佳為碳數7~20,其烷基部分,可為直鏈、分支、環狀之任意者。
其具體例子,可列舉苄基、p-甲基苯基甲基、m-甲基苯基甲基、o-乙基苯基甲基、m-乙基苯基甲基、p-乙基苯基甲基、2-丙基苯基甲基、4-異丙基苯基甲基、4-異丁基苯基甲基、α-萘基甲基等。
上述Ar係表示選自由式(2)~(13)所示之群的至少1種。
上述R1~R92係互相獨立地表示氫原子、鹵素原子、羧基、磺基、碳數1~10之可具有分支構造之烷基、或碳數1~10之可具有分支構造之烷氧基,W1及W2係互相獨立地表示單鍵、CR95R96(R95及R96係互相獨立地表示氫原子或碳數1~10之可具有分支構造之烷基(惟,此等亦可一起形成環))、C=O、O、S、SO、SO2、或NR97(R97係表示氫原子或碳數1~10之可具有分支構造之烷基),R93及R94係表示氫原子或碳數1~10之可具有分支構造之烷基。
鹵素原子可列舉氟原子、氯原子、溴原子、碘原子。
再者,作為烷基、烷氧基者,可列舉與上述相同者。
又,X1及X2係互相獨立地表示單鍵、碳數1~10之可具有分支構造之伸烷基、或式(14)所示之基。
上述R98~R101係互相獨立地表示氫原子、鹵素原子、羧基、磺基、碳數1~10之可具有分支構造之烷基、或碳數1~10之可具有分支構造之烷氧基,Y1及Y2係互相獨立地表示單鍵或碳數1~10之可具有分支構造之伸烷基。作為此等鹵素原子、烷基、烷氧基,可列舉與上述相同者。
碳數1~10之可具有分支構造之伸烷基,可列舉亞甲基、伸乙基、伸丙基、三亞甲基、四亞甲基、五亞甲基等。
特別地,作為Ar者,較佳為式(2)、(5)~(13)所示之至少1種;更佳為式(2)、(5)、(7)、(8)、(11)~(13)所示之至少1種。上述式(2)~(13)表示之芳基之具體例子,可列舉下述式所示者,但不限定於此等。
此等之中,因可得到更高折射率之聚合物,尤以下述式所示之芳基更佳。
特別地,考慮到更提高對光阻溶劑等之安全性高之溶劑的溶解性時,較佳為包含式(15)所示之重複單位構造。
由如此觀點,作為特別適合的重複單位構造,可列舉下述式(16)所示者,而下述式(17)所示之高分支聚合物(超分支狀聚合物)最適合。
本發明中之聚合物的重量平均分子量,並無特殊限定,較佳為500~500,000、更佳為500~100,000,由更提高耐熱性,而且降低收縮率之觀點而言,較佳為2,000以上,由更提高溶解性,降低所得之溶液的黏度之觀點而言,較佳為50,000以下、更佳為30,000以下、又更佳為10,000以下。
再者,本發明中之重量平均分子量,係藉由凝膠滲透層析(以下稱為GPC)分析,以標準聚苯乙烯換算所得到之平均分子量。
本發明之含有三嗪環之聚合物,可藉由上述專利文獻5所揭示之方法製造。
例如,如下述流程1所示,具有重複構造(17’)之高分支聚合物(超分支狀聚合物),可藉由使鹵化三聚氰醯(18)及m-苯二胺化合物(19)在適當的有機溶劑中反應而得到。
如下述流程2所示,具有重複構造(17’)之高分支聚合物(超分支狀聚合物),亦可藉由自使鹵化三聚氰醯(18)及m-苯二胺化合物(19)在適當的有機溶劑中,使用等量來反應而得的化合物(20)來合成。
流程1及2之方法中,各原料之饋入量,只要可得到目標之聚合物,則為任意,但較佳係相對於鹵化三聚氰醯(18)1當量而言,為二胺基化合物(19)
0.01~10當量。
特別是流程1方法的情況時,較佳為相對於鹵化三聚氰醯(18)2當量而言,避免使用二胺基化合物(19)3當量。藉由使官能基之當量錯開,可防止生成凝膠化物。
為了得到具有多數之各種分子量的三嗪環末端之高分支聚合物(超分支狀聚合物),較佳為相對於鹵化三聚氰醯(18)2當量而言,使用未達3當量之量的二胺基化合物(19)。
另一方面,為了得到具有多數之各種分子量的胺末端之高分支聚合物(超分支狀聚合物),較佳為相對於二胺基化合物(19)3當量而言,使用未達2當量之量的鹵化三聚氰醯(18)。
例如,製作薄膜時,就具有優良透明性或耐光性之觀點而言,較佳為具有多數之三嗪環末端的高分支聚合物(超分支狀聚合物)。
如此地,藉由適當調整二胺基化合物(19)或鹵化三聚氰醯(18)之量,可輕易調節所得之高分支聚合物(超分支狀聚合物)的分子量。
作為上述有機溶劑者,可使用此種反應中通常所用之各種溶劑,可列舉例如四氫呋喃、二噁烷、二甲基亞碸;N,N-二甲基甲醯胺、N-甲基-2-吡咯啶酮、四甲基尿素、六甲基磷醯胺、N,N-二甲基乙醯胺、N-甲基-2-哌啶酮、N,N-二甲基乙烯尿素、N,N,N’,N’-四甲基丙二酸醯胺、N-甲基己內醯胺、N-乙醯基吡咯啶、N,N-二乙基乙
醯胺、N-乙基-2-吡咯啶酮、N,N-二甲基丙酸醯胺、N,N-二甲基異丁基醯胺、N-甲基甲醯胺、N,N’-二甲基丙烯尿素等之醯胺系溶劑、及該等之混合溶劑。
其中尤以N,N-二甲基甲醯胺、二甲基亞碸、N-甲基-2-吡咯啶酮、N,N-二甲基乙醯胺、及該等之混合系較佳,特別以N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮為適合。
流程1及流程2之第2階段反應中,反應溫度只要係於所用溶劑之熔點至沸點之範圍適當設定即可,特佳為0~150℃左右、又更佳為60~100℃。
特別是流程1之反應中,就抑制線性,提高分支度之觀點而言,反應溫度較佳為60~150℃、更佳為80~150℃、又更佳為80~120℃。
流程2之第1階段反應中,反應溫度只要係於所用溶劑之熔點至溶劑的沸點之範圍適當設定即可,特佳為-50~50℃左右、又更佳為-20~50℃左右、又再更佳為-10~50℃左右、又進一步更佳為-10~10℃。
特別是流程2的方法中,較佳為採用於-50~50℃反應之第1步驟、與接續該步驟後之於60~150℃反應的第2步驟所成之2階段步驟。
上述各反應中,各成分之摻合順序雖係任意,最適宜為在流程1之反應中,將含有鹵化三聚氰醯(18)或二胺基化合物(19)及有機溶劑的溶液加熱至60~150℃、較佳為80~150℃,在該溫度下,於該溶液中添加二胺基化合物(19)或鹵化三聚氰醯(18)之方法。
此時,預先溶解於溶劑之成分及其後所添加之成分係何者均可,然較佳為於二胺基化合物(19)之加熱溶液中添加鹵化三聚氰醯(18)之方法。
又,流程2之反應中,預先溶解於溶劑之成分及其後所添加之成分係何者均可,然較佳為於鹵化三聚氰醯(18)之冷卻溶液中添加二胺基化合物(19)之方法。
其後所添加之成分,可為以無溶劑方式添加、亦能夠以溶解於如上述之有機溶劑而得的溶液的方式添加,然考慮到操作之容易度或反應控制的容易度等時,後者之方法為適宜。
又,添加可藉由滴下等慢慢添加、亦可全部量一次添加。
流程1中,即使於經加熱之狀態將兩化合物混合後,(不階段性地提高溫度)以一階段進行反應的情況時,亦可不會凝膠化地,得到目標之含有三嗪環之高分支聚合物(超分支狀聚合物)。
又,上述流程1及流程2之第2階段反應中,亦可添加聚合時或聚合後通常所使用之各種鹼。
該鹼之具體例子,可列舉碳酸鉀、氫氧化鉀、碳酸鈉、氫氧化鈉、碳酸氫鈉、乙氧化鈉、乙酸鈉、碳酸鋰、氫氧化鋰、氧化鋰、乙酸鉀、氧化鎂、氧化鈣、氫氧化鋇、磷酸三鋰、磷酸三鈉、磷酸三鉀、氟化銫、氧化鋁、氨、三甲基胺、三乙基胺、二異丙基胺、二異丙基乙基胺、N-甲基哌啶、2,2,6,6-四甲基-N-甲基哌啶、吡啶、4-
二甲基胺基吡啶、N-甲基嗎啉等。
鹼之添加量,相對於鹵化三聚氰醯(18)1當量而言,較佳為1~100當量、更佳為1~10當量。再者,此等之鹼亦可以水溶液的形式使用。
所有的流程之方法中,均可藉由於反應結束後,將生成物以再沈澱法等而輕易地精製。
再者,本發明中,亦可將至少1個末端三嗪環之鹵素原子的一部分,以烷基、芳烷基、芳基、烷基胺基、含有烷氧基矽烷基之烷基胺基、芳烷基胺基、芳基胺基、烷氧基、芳烷氧基、芳氧基、酯基等封端(capping)。
此等之中,尤以烷基胺基、含有烷氧基矽烷基之烷基胺基、芳烷基胺基、芳基胺基較佳;更佳為烷基胺基、芳基胺基;又更佳為芳基胺基。
上述烷基、烷氧基,可列舉與上述相同者。
酯基之具體例子,可列舉甲氧基羰基、乙氧基羰基等。
芳基之具體例子,可列舉苯基、o-氯苯基、m-氯苯基、p-氯苯基、o-氟苯基、p-氟苯基、o-甲氧基苯基、p-甲氧基苯基、p-硝基苯基、p-氰基苯基、α-萘基、β-萘基、o-聯苯基、m-聯苯基、p-聯苯基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基等。
芳烷基之具體例子,可列舉苄基、p-甲基苯基甲基、m-甲基苯基甲基、o-乙基苯基甲基、m-乙基苯基甲基、p-
乙基苯基甲基、2-丙基苯基甲基、4-異丙基苯基甲基、4-異丁基苯基甲基、α-萘基甲基等。
烷基胺基之具體例子,可列舉甲基胺基、乙基胺基、n-丙基胺基、異丙基胺基、n-丁基胺基、異丁基胺基、s-丁基胺基、t-丁基胺基、n-戊基胺基、1-甲基-n-丁基胺基、2-甲基-n-丁基胺基、3-甲基-n-丁基胺基、1,1-二甲基-n-丙基胺基、1,2-二甲基-n-丙基胺基、2,2-二甲基-n-丙基胺基、1-乙基-n-丙基胺基、n-己基胺基、1-甲基-n-戊基胺基、2-甲基-n-戊基胺基、3-甲基-n-戊基胺基、4-甲基-n-戊基胺基、1,1-二甲基-n-丁基胺基、1,2-二甲基-n-丁基胺基、1,3-二甲基-n-丁基胺基、2,2-二甲基-n-丁基胺基、2,3-二甲基-n-丁基胺基、3,3-二甲基-n-丁基胺基、1-乙基-n-丁基胺基、2-乙基-n-丁基胺基、1,1,2-三甲基-n-丙基胺基、1,2,2-三甲基-n-丙基胺基、1-乙基-1-甲基-n-丙基胺基、1-乙基-2-甲基-n-丙基胺基等。
芳烷基胺基之具體例子,可列舉苄基胺基、甲氧基羰基苯基甲基胺基、乙氧基羰基苯基甲基胺基、p-甲基苯基甲基胺基、m-甲基苯基甲基胺基、o-乙基苯基甲基胺基、m-乙基苯基甲基胺基、p-乙基苯基甲基胺基、2-丙基苯基甲基胺基、4-異丙基苯基甲基胺基、4-異丁基苯基甲基胺基、萘基甲基胺基、甲氧基羰基萘基甲基胺基、乙氧基羰基萘基甲基胺基等。
芳基胺基之具體例子,可列舉苯基胺基、甲氧基羰基苯基胺基、乙氧基羰基苯基胺基、萘基胺基、甲氧基羰基
萘基胺基、乙氧基羰基萘基胺基、蒽基胺基、芘基胺基、聯苯基胺基、聯三苯基胺基、茀基胺基等。
含有烷氧基矽烷基之烷基胺基,可為含有單烷氧基矽烷基之烷基胺基、含有二烷氧基矽烷基之烷基胺基、含有三烷氧基矽烷基之烷基胺基之任意者,其具體例子,可列舉3-三甲氧基矽烷基丙基胺基、3-三乙氧基矽烷基丙基胺基、3-二甲基乙氧基矽烷基丙基胺基、3-甲基二乙氧基矽烷基丙基胺基、N-(2-胺基乙基)-3-二甲基甲氧基矽烷基丙基胺基、N-(2-胺基乙基)-3-甲基二甲氧基矽烷基丙基胺基、N-(2-胺基乙基)-3-三甲氧基矽烷基丙基胺基等。
芳氧基之具體例子,可列舉苯氧基、萘氧基、蒽氧基、芘氧基、聯苯氧基、聯三苯氧基、茀氧基等。
芳烷氧基之具體例子,可列舉苄氧基、p-甲基苯基甲基氧基、m-甲基苯基甲基氧基、o-乙基苯基甲基氧基、m-乙基苯基甲基氧基、p-乙基苯基甲基氧基、2-丙基苯基甲基氧基、4-異丙基苯基甲基氧基、4-異丁基苯基甲基氧基、α-萘基甲基氧基等。
此等之基,可藉由將三嗪環上之鹵素原子以賦予所對應之取代基的化合物取代,而容易地導入,例如,如下述式流程3所示,藉由添加苯胺衍生物使其反應,可得到於至少1個末端具有苯基胺基之高分支聚合物(21)。
此時,藉由進行有機單胺之同時饋入,亦即在有機單胺之存在下,使鹵化三聚氰醯化合物與二胺基芳基化合物進行反應,可得到超分支狀聚合物之剛性被緩和之分支度低的柔軟超分支狀聚合物。
藉由此方法所得到之超分支狀聚合物,係成為對溶劑之溶解性(凝集抑制)、或與交聯劑之交聯性優良者。
此處,有機單胺可使用烷基單胺、芳烷基單胺、芳基單胺之任意者。
烷基單胺,可列舉甲基胺、乙基胺、n-丙基胺、異丙基胺、n-丁基胺、異丁基胺、s-丁基胺、t-丁基胺、n-戊基胺、1-甲基-n-丁基胺、2-甲基-n-丁基胺、3-甲基-n-丁基胺、1,1-二甲基-n-丙基胺、1,2-二甲基-n-丙基胺、2,2-二甲基-n-丙基胺、1-乙基-n-丙基胺、n-己基胺、1-甲基-n-戊基胺、2-甲基-n-戊基胺、3-甲基-n-戊基胺、4-甲基-n-戊基胺、1,1-二甲基-n-丁基胺、1,2-二甲基-n-丁基胺、1,3-二甲基-n-丁基胺、2,2-二甲基-n-丁基胺、2,3-
二甲基-n-丁基胺、3,3-二甲基-n-丁基胺、1-乙基-n-丁基胺、2-乙基-n-丁基胺、1,1,2-三甲基-n-丙基胺、1,2,2-三甲基-n-丙基胺、1-乙基-1-甲基-n-丙基胺、1-乙基-2-甲基-n-丙基胺、2-乙基己基胺等。
芳烷基單胺之具體例子,可列舉苄基胺、p-甲氧基羰基苄基胺、p-乙氧基羰基苄基胺、p-甲基苄基胺、m-甲基苄基胺、o-甲氧基苄基胺等。
芳基單胺之具體例子,可列舉苯胺、p-甲氧基羰基苯胺、p-乙氧基羰基苯胺、p-甲氧基苯胺、1-萘基胺、2-萘基胺、蒽基胺、1-胺基芘、4-聯苯基胺、o-苯基苯胺、4-胺基-p-聯三苯基、2-胺基茀等。
此時,有機單胺之使用量,相對於鹵化三聚氰醯化合物而言,較佳成為0.05~500當量、更佳為0.05~120當量、又更佳為0.05~50當量。
此時之反應溫度,亦由抑制線性、提高分支度之觀點而言,反應溫度較佳為60~150℃、更佳為80~150℃、又更佳為80~120℃。
惟,有機單胺、鹵化三聚氰醯化合物、二胺基芳基化合物之3成分的混合,亦可在低溫下進行,此時之溫度,較佳為-50~50℃左右、更佳為-20~50℃左右、又更佳為-20~10℃。低溫饋入後,較佳為一口氣(以一階段)地昇溫至聚合之溫度來進行反應。
又,鹵化三聚氰醯化合物與二胺基芳基化合物之2成分的混合,亦可在低溫下進行,此時之溫度,較佳為-50~
50℃左右、更佳為-20~50℃左右、又更佳為-20~10℃。低溫饋入後,較佳為添加有機單胺,一口氣(以一階段)地昇溫至聚合之溫度來進行反應。
又,在如此有機單胺之存在下,使鹵化三聚氰醯化合物與二胺基芳基化合物進行反應之反應,亦可使用與上述相同之有機溶劑來進行。
本發明之光散射膜形成用組成物所用之交聯劑,只要係具有可與上述含有三嗪環之聚合物反應的取代基之化合物,則無特殊限定。
如此之化合物,可列舉具有羥甲基、甲氧基甲基等之交聯形成取代基的三聚氰胺系化合物、取代尿素系化合物、含有環氧基或氧雜環丁烷基等之交聯形成取代基的化合物、具有異氰酸酯基之化合物、含有嵌段化異氰酸酯之化合物、具有酸酐之化合物、具有(甲基)丙烯酸基之化合物、酚樹脂(phenoplast)化合物等,就耐熱性或保存安定性之觀點而言,較佳為含有環氧基、異氰酸酯基、嵌段異氰酸酯基、(甲基)丙烯酸基之化合物,特佳為具有異氰酸酯基之化合物;或即使不使用起始劑亦可得到能夠光硬化之組成物的多官能環氧化合物及/或多官能(甲基)丙烯酸化合物。
再者,此等之化合物,當使用於聚合物的末端處理時,只要具有至少1個交聯形成取代基即可,當使用於聚合物彼此的交聯處理時,必須具有至少2個交聯形成取代基。
多官能環氧化合物,只要係一分子中具有2個以上之環氧基者,則無特殊限定。
其具體例子,可列舉參(2,3-環氧基丙基)三聚異氰酸酯、1,4-丁二醇二環氧丙基醚、1,2-環氧基-4-(環氧基乙基)環己烷、甘油三環氧丙基醚、二乙二醇二環氧丙基醚、2,6-二環氧丙基苯基環氧丙基醚、1,1,3-參[p-(2,3-環氧基丙氧基)苯基]丙烷、1,2-環己烷二羧酸二環氧丙酯、4,4’-亞甲基雙(N,N-二環氧丙基苯胺)、3,4-環氧基環己基甲基-3,4-環氧基環己烷羧酸酯、三羥甲基乙烷三環氧丙基醚、雙酚-A-二環氧丙基醚、季戊四醇聚環氧丙基醚等。
又,就市售品而言,亦可使用至少具有2個環氧基之環氧樹脂的YH-434、YH434L(東都化成(股)製)、具有環氧環己烷(cyclohexene oxide)構造之環氧樹脂的EpoLead GT-401、同GT-403、同GT-301、同GT-302、Celloxide 2021、同3000(Daicel化學工業(股)製)、雙酚A型環氧樹脂的Epikote(現、jER)1001、同1002、同1003、同1004、同1007、同1009、同1010、同828(以上,Japan Epoxy Resin(股)製)、雙酚F型環氧樹脂的Epikote(現、jER)807(Japan Epoxy Resin(股)製)、酚酚醛清漆(phenol novolac)型環氧樹脂的Epikote(現、jER)152、同154(以上,Japan Epoxy Resin(股)製)、EPPN201、同202(以上,日本化藥(股)製)、甲酚酚醛清漆型環氧樹脂的EOCN-102、同
103S、同104S、同1020、同1025、同1027(以上,日本化藥(股)製)、Epikote(現、jER)180S75(Japan Epoxy Resin(股)製)、脂環式環氧樹脂的DENACOL EX-252(Nagase chemteX(股)製)、CY175、CY177、CY179(以上,CIBA-GEIGY A.G製)、Araldite CY-182、同CY-192、同CY-184(以上,CIBA-GEIGY A.G製)、EPICLON 200、同400(以上,DIC(股)製)、Epikote(現、jER)871、同872(以上,Japan Epoxy Resin(股)製)、ED-5661、ED-5662(以上,Celanese Coating(股)製)、脂肪族聚環氧丙基醚的DENACOL EX-611、同EX-612、同EX-614、同EX-622、同EX-411、同EX-512、同EX-522、同EX-421、同EX-313、同EX-314、同EX-321(Nagase chemteX(股)製)等。
多官能(甲基)丙烯酸化合物,只要係一分子中具有2個以上之(甲基)丙烯酸基者,則無特殊限定。
其具體例子,可列舉乙二醇二丙烯酸酯、乙二醇二甲基丙烯酸酯、聚乙二醇二丙烯酸酯、聚乙二醇二甲基丙烯酸酯、乙氧基化雙酚A二丙烯酸酯、乙氧基化雙酚A二甲基丙烯酸酯、乙氧基化三羥甲基丙烷三丙烯酸酯、乙氧基化三羥甲基丙烷三甲基丙烯酸酯、乙氧基化甘油三丙烯酸酯、乙氧基化甘油三甲基丙烯酸酯、乙氧基化季戊四醇四丙烯酸酯、乙氧基化季戊四醇四甲基丙烯酸酯、乙氧基化二季戊四醇六丙烯酸酯、聚甘油單環氧乙烷聚丙烯酸
酯、聚甘油聚乙二醇聚丙烯酸酯、二季戊四醇六丙烯酸酯、二季戊四醇六甲基丙烯酸酯、新戊二醇二丙烯酸酯、新戊二醇二甲基丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇三甲基丙烯酸酯、三羥甲基丙烷三丙烯酸酯、三羥甲基丙烷三甲基丙烯酸酯、三環癸烷二甲醇二丙烯酸酯、三環癸烷二甲醇二甲基丙烯酸酯、1,6-己二醇二丙烯酸酯、1,6-己二醇二甲基丙烯酸酯等。
又,多官能(甲基)丙烯酸化合物,可作為市售品而獲得,其具體例子,可列舉NK Ester A-200、同A-400、同A-600、同A-1000、同A-9300(三聚異氰酸參(2-丙烯醯氧基乙酯))、同A-9300-1CL、同A-TMPT、同UA-53H、同1G、同2G、同3G、同4G、同9G、同14G、同23G、同ABE-300、同A-BPE-4、同A-BPE-6、同A-BPE-10、同A-BPE-20、同A-BPE-30、同BPE-80N、同BPE-100N、同BPE-200、同BPE-500、同BPE-900、同BPE-1300N、同A-GLY-3E、同A-GLY-9E、同A-GLY-20E、同A-TMPT-3EO、同A-TMPT-9EO、同AT-20E、同ATM-4E、同ATM-35E(以上,新中村化學工業(股)製)、KAYARAD(註冊商標)DPEA-12、同PEG400DA、同THE-330、同RP-1040(以上,日本化藥(股)製)、M-210、M-350(以上,東亞合成(股)製)、KAYARAD(註冊商標)DPHA、同NPGDA、同PET30(以上,日本化藥(股)製)、NK Ester A-DPH、同A-TMPT、同A-DCP、同A-HD-N、同TMPT、同
DCP、同NPG、同HD-N(以上,新中村化學工業(股)製)、NK Oligo U-15HA(新中村化學工業(股)製)、NK Polymer Vanaresin GH-1203(新中村化學工業(股)製)等。
作為酸酐化合物者,只要係使2分子之羧酸脫水縮合而得的羧酸酐,則無特殊限定,其具體例子,可列舉鄰苯二甲酸酐、四氫鄰苯二甲酸酐、六氫鄰苯二甲酸酐、甲基四氫鄰苯二甲酸酐、甲基六氫鄰苯二甲酸酐、橋亞甲基四氫鄰苯二甲酸酐(nadic anhydride)、甲基橋亞甲基四氫鄰苯二甲酸酐、馬來酸酐、琥珀酸酐、辛基琥珀酸酐、十二烯基琥珀酸酐等之分子內具有1個酸酐基者;1,2,3,4-環丁烷四羧酸二酐、苯均四酸酐、3,4-二羧基-1,2,3,4-四氫-1-萘琥珀酸二酐、雙環[3.3.0]辛烷-2,4,6,8-四羧酸二酐、5-(2,5-二氧代四氫-3-呋喃基)-3-甲基-3-環己烯-1,2-二羧酸酐、1,2,3,4-丁烷四羧酸二酐、3,3’,4,4’-二苯甲酮四羧酸二酐、3,3’,4,4’-聯苯基四羧酸二酐、2,2-雙(3,4-二羧基苯基)六氟丙烷二無水物、1,3-二甲基-1,2,3,4-環丁烷四羧酸二酐等之分子內具有2個酸酐基者等。
含有嵌段化異氰酸酯之化合物,只要係一分子中具有2個以上之將異氰酸酯基(-NCO)以適當之保護基封端之嵌段化異氰酸酯基,且暴露於熱硬化時的高溫時,保護基(封端部分)熱解離而脫離,所生成的異氰酸酯基與樹脂之間引起交聯反應者,則無特殊限定,可列舉
例如一分子中具有2個以上之下述式所示之基(再者,此等之基可為相同、亦可為各自相異者)的化合物。
如此之化合物,例如可使適當的封端劑對一分子中具有2個以上之異氰酸酯基的化合物反應而得到。
一分子中具有2個以上之異氰酸酯基的化合物,可列舉例如異佛酮二異氰酸酯、1,6-六亞甲基二異氰酸酯、亞甲基雙(4-環己基異氰酸酯)、三甲基六亞甲基二異氰酸酯等之聚異氰酸酯;或此等之二聚體、三聚體、及此等與二醇類、三醇類、二胺類、或三胺類的反應物等。
封端劑,可列舉例如甲醇、乙醇、異丙醇、n-丁醇、2-乙氧基己醇、2-N,N-二甲基胺基乙醇、2-乙氧基乙醇、環己醇等之醇類;酚、o-硝基酚、p-氯酚、o-、m-或p-甲酚等之酚類;ε-己內醯胺等之內醯胺類、丙酮肟、甲基乙基酮肟、甲基異丁基酮肟、環己酮肟、苯乙酮肟、二苯甲酮肟等之肟類;吡唑、3,5-二甲基吡唑、3-甲基吡唑等之吡唑類;十二烷硫醇、苯硫醇等之硫醇類等。
含有嵌段化異氰酸酯之化合物,亦可作為市售品而獲得,其具體例子,可列舉B-830、B-815N、B-842N、B-870N、B-874N、B-882N、B-7005、B-7030、B-7075、B-5010(以上,三井化學聚胺基甲酸酯(股)
製)、Duranate(註冊商標)17B-60PX、同TPA-B80E、同MF-B60X、同MF-K60X、同E402-B80T(以上,旭化成化學品(股)製)、Karenz MOI-BM(註冊商標)(以上,昭和電工(股)製)等。
作為胺基樹脂(aminoplast)化合物者,只要係一分子中具有2個以上之甲氧基亞甲基者,則無特殊限定,可列舉例如六甲氧基甲基三聚氰胺CYMEL(註冊商標)303、四丁氧基甲基乙炔脲同1170、四甲氧基甲基苯并胍胺同1123(以上,日本Cytec Industries(股)製)等之CYMEL系列;甲基化三聚氰胺樹脂的Nikalac(註冊商標)MW-30HM、同MW-390、同MW-100LM、同MX-750LM、甲基化尿素樹脂的同MX-270、同MX-280、同MX-290(以上,(股)三和化學品製)等之Nikalac系列等之三聚氰胺系化合物。
作為氧雜環丁烷化合物者,只要係一分子中具有2個以上之氧雜環丁烷基者,則無特殊限定,可列舉例如含有氧雜環丁烷基之OXT-221、OX-SQ-H、OX-SC(以上,東亞合成(股)製)等。
酚樹脂化合物,係於一分子中具有2個以上之羥基亞甲基,且暴露於熱硬化時之高溫時,與本發明之聚合物之間藉由脫水縮合反應而進行交聯反應者。
酚樹脂化合物,可列舉例如2,6-二羥基甲基-4-甲基酚、2,4-二羥基甲基-6-甲基酚、雙(2-羥基-3-羥基甲基-5-甲基苯基)甲烷、雙(4-羥基-3-羥基甲基-5-甲基苯
基)甲烷、2,2-雙(4-羥基-3,5-二羥基甲基苯基)丙烷、雙(3-甲醯基-4-羥基苯基)甲烷、雙(4-羥基-2,5-二甲基苯基)甲醯基甲烷、α,α-雙(4-羥基-2,5-二甲基苯基)-4-甲醯基甲苯等。
酚樹脂化合物,亦可作為市售品而獲得,其具體例子,可列舉26DMPC、46DMOC、DM-BIPC-F、DM-BIOC-F、TM-BIP-A、BISA-F、BI25X-DF、BI25X-TPA(以上,旭有機材工業(股)製)等。
此等之中,就可抑制因摻合交聯劑所致之折射率降低,而且硬化反應會迅速進行的點而言,尤以多官能(甲基)丙烯酸化合物為適宜,其中,由與含有三嗪環之聚合物的相溶性優良而言,尤更佳為下述具有三聚異氰酸骨架之多官能(甲基)丙烯酸化合物。
具有如此骨架之多官能(甲基)丙烯酸化合物,可列舉例如NK Ester A-9300、同A-9300-1CL(均為新中村化學工業(股)製)等。
又,由更提高硬化速度,而且提高所得硬化
膜之耐溶劑性、耐酸性及耐鹼性的觀點而言,適合為使用單獨或2種以上組合之於25℃為液體,且其黏度為5000mPa‧s以下、較佳為1~3000mPa‧s、更佳為1~1000mPa‧s、又更佳為1~500mPa‧s之多官能(甲基)丙烯酸化合物(以下稱為低黏度交聯劑);或與上述具有三聚異氰酸骨架之多官能(甲基)丙烯酸化合物組合來使用。
如此之低黏度交聯劑亦可作為市售品而獲得,例如,上述多官能(甲基)丙烯酸化合物當中,可列舉NK Ester A-GLY-3E(85mPa‧s,25℃)、同A-GLY-9E(95mPa‧s,25℃)、同A-GLY-20E(200mPa‧s,25℃)、同A-TMPT-3EO(60mPa‧s,25℃)、同A-TMPT-9EO、同ATM-4E(150mPa‧s,25℃)、同ATM-35E(350mPa‧s,25℃)(以上,新中村化學工業(股)製)等之(甲基)丙烯酸基間之鏈長比較長的交聯劑。
進而,考慮到亦提高所得硬化膜之耐鹼性時,適合為組合使用NK Ester A-GLY-20E(新中村化學工業(股)製)、與上述具有三聚異氰酸骨架之多官能(甲基)丙烯酸化合物。
上述交聯劑可單獨使用、亦可組合2種以上使用。交聯劑之使用量,相對於含有三嗪環之聚合物100質量份而言,較佳為1~100質量份,但考慮到溶劑耐性時,其下限較佳為2質量份、更佳為5質量份,進一步考慮到控制折射率時,其上限較佳為20質量份、更佳為15
質量份。
本發明所用之光散射膜形成用組成物中,亦可摻合因應各交聯劑之起始劑。再者,如上所述,使用多官能環氧化合物及/或多官能(甲基)丙烯酸化合物作為交聯劑時,雖即使不使用起始劑光硬化亦會進行而得到硬化膜,但此時使用起始劑亦可。
使用多官能環氧化合物作為交聯劑時,可使用光酸產生劑或光鹼產生劑。
作為光酸產生劑者,只要由周知者中適當選擇使用即可,例如可使用重氮鎓鹽、鋶鹽或錪鹽等之鎓鹽衍生物。
其具體例子,可列舉苯基重氮鎓六氟磷酸鹽、4-甲氧基苯基重氮鎓六氟銻酸鹽、4-甲基苯基重氮鎓六氟磷酸鹽等之芳基重氮鎓鹽;二苯基錪六氟銻酸鹽、二(4-甲基苯基)錪六氟磷酸鹽、二(4-tert-丁基苯基)錪六氟磷酸鹽等之二芳基錪鹽;三苯基鋶六氟銻酸鹽、參(4-甲氧基苯基)鋶六氟磷酸鹽、二苯基-4-硫苯氧基苯基鋶六氟銻酸鹽、二苯基-4-硫苯氧基苯基鋶六氟磷酸鹽、4,4’-雙(二苯基鋶基)苯基硫醚-雙六氟銻酸鹽、4,4’-雙(二苯基鋶基)苯基硫醚-雙六氟磷酸鹽、4,4’-雙[二(β-羥基乙氧基)苯基鋶基]苯基硫醚-雙六氟銻酸鹽、4,4’-雙[二(β-羥基乙氧基)苯基鋶基]苯基硫醚-雙-六氟磷酸鹽、4-[4’-(苄醯基)苯硫基]苯基-二(4-氟苯基)鋶六氟銻酸鹽、4-[4’-(苄醯基)苯硫基]苯基-二(4-氟苯基)鋶六氟磷酸鹽等之三芳基鋶鹽等。
此等之鎓鹽亦可使用市售品,其具體例子,可列舉San-Aid SI-60、SI-80、SI-100、SI-60L、SI-80L、SI-100L、SI-L145、SI-L150、SI-L160、SI-L110、SI-L147(以上,三新化學工業(股)製)、UVI-6950、UVI-6970、UVI-6974、UVI-6990、UVI-6992(以上,Union Carbide公司製)、CPI-100P、CPI-100A、CPI-200K、CPI-200S(以上,San-Apro(股)製)、Adekaoptomer SP-150、SP-151、SP-170、SP-171(以上,旭電化工業(股)製)、Irgacure 261(BASF公司製)、CI-2481、CI-2624、CI-2639、CI-2064(以上,日本曹達(股)製)、CD-1010、CD-1011、CD-1012(以上,Sartomer公司製)、DS-100、DS-101、DAM-101、DAM-102、DAM-105、DAM-201、DSM-301、NAI-100、NAI-101、NAI-105、NAI-106、SI-100、SI-101、SI-105、SI-106、PI-105、NDI-105、BENZOIN TOSYLATE、MBZ-101、MBZ-301、PYR-100、PYR-200、DNB-101、NB-101、NB-201、BBI-101、BBI-102、BBI-103、BBI-109(以上,Midori化學(股)製)、PCI-061T、PCI-062T、PCI-020T、PCI-022T(以上,日本化藥(股)製)、IBPF、IBCF(三和化學品(股)製)等。
另一方面,光鹼產生劑亦只要由周知者當中適當選擇來使用即可,例如可使用Co-胺錯合物系、肟羧酸酯系、胺基甲酸酯系、四級銨鹽系光鹼產生劑等。
其具體例子,可列舉胺基甲酸2-硝基苄基環己酯、三
苯基甲醇、O-胺基甲醯基羥基醯胺、O-胺基甲醯基肟、[[(2,6-二硝基苄基)氧基]羰基]環己基胺、雙[[(2-硝基苄基)氧基]羰基]己烷1,6-二胺、4-(甲硫基苄醯基)-1-甲基-1-嗎啉基乙烷、(4-嗎啉基苄醯基)-1-苄基-1-二甲基胺基丙烷、N-(2-硝基苄氧基羰基)吡咯啶、六氨鈷(III)參(三苯基甲基硼酸鹽)、2-苄基-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2,6-二甲基-3,5-二乙醯基-4-(2’-硝基苯基)-1,4-二氫吡啶、2,6-二甲基-3,5-二乙醯基-4-(2’,4’-二硝基苯基)-1,4-二氫吡啶等。
又,光鹼產生劑亦可使用市售品,其具體例子,可列舉TPS-OH、NBC-101、ANC-101(均為產品名、Mirori化學(股)製)等。
使用光酸或鹼產生劑時,其使用量,相對於多官能環氧化合物100質量份而言,較佳為0.1~15質量份之範圍、更佳為1~10質量份之範圍。
再者,亦可依需要,以相對於多官能環氧化合物100質量份而言為1~100質量份的量來摻合環氧樹脂硬化劑。
另一方面,使用多官能(甲基)丙烯酸化合物時,可使用光自由基聚合起始劑。
光自由基聚合起始劑亦只要由周知者當中適當選擇來使用即可,可列舉例如苯乙酮類、二苯甲酮類、米其勒(Michler)之苄酸苄醯酯、戊肟酯(amyloxime ester)、肟酯類、四甲基甲硫碳醯胺單硫化物及噻噸酮類等。
特佳為光開裂型之光自由基聚合起始劑。關於光開裂
型之光自由基聚合起始劑,係記載於最新UV硬化技術(159頁,發行人:高薄一弘、發行所:(股)技術情報協會、1991年發行)。
市售之光自由基聚合起始劑,可列舉例如BASF公司製 商品名:Irgacure 127、184、369、379、379EG、651、500、754、819、903、907、784、2959、CGI1700、CGI1750、CGI1850、CG24-61、OXE01、OXE02、Darocur 1116、1173、MBF、BASF公司製 商品名:LUSILIN TPO、UCB公司製 商品名:Ebecryl P36、Fratelli Lamberti公司製 商品名:Esacure KIP150、KIP65LT、KIP100F、KT37、KT55、KTO46、KIP75/B等。
使用光自由基聚合起始劑時,相對於多官能(甲基)丙烯酸酯化合物100質量份而言,較佳於0.1~200質量份之範圍使用、更佳於1~150質量份之範圍使用。
本發明所用之光散射膜形成用組成物中,為了提高所得硬化膜之光擴散性,係進一步摻合光擴散劑。
光擴散劑並無特殊限定,可使用有機無機複合光擴散劑、有機光擴散劑、無機光擴散劑,此等可分別單獨使用、可組合同種的2種以上使用、亦可組合異種的2種以上使用。
進一步地,上述光擴散劑亦可使用經氧化矽、有機矽化合物、有機金屬化合物等表面處理的微粒子。
再者,以氧化矽進行之處理,係指於含有無機微粒子之分散體中,使氧化矽微粒子以周知之方法於微粒子表面成長者。以有機矽化合物、有機金屬化合物所進行的處理,係指於含有無機微粒子之分散體中添加此等之化合物,並加熱攪拌者。
上述有機矽化合物可列舉矽烷偶合劑或矽烷,矽烷偶合劑之具體例子,可列舉乙烯基三氯矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、2-(3,4-環氧基環己基)乙基三甲氧基矽烷、3-環氧丙氧基丙基三甲氧基矽烷、3-環氧丙氧基丙基甲基二-三乙氧基矽烷、3-環氧丙氧基丙基三乙氧基矽烷、p-苯乙烯基三甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷、3-甲基丙烯醯氧基丙基三乙氧基矽烷、3-丙烯醯氧基丙基三甲氧基矽烷、N-2-(胺基乙基)-3-胺基丙基甲基二甲氧基矽烷、N-2-(胺基乙基)-3-胺基丙基甲基三甲氧基矽烷、N-2-(胺基乙基)-3-胺基丙基甲基三乙氧基矽烷、3-胺基丙基三甲氧基矽烷、3-胺基丙基三乙氧基矽烷、3-三乙氧基矽烷基-N-(1,3-二甲基-亞丁基)丙基胺、N-苯基-3-胺基丙基三甲氧基矽烷、3-氯丙基三甲氧基矽烷、3-巰基丙基甲基二甲氧基矽烷、3-巰基丙基三甲氧基矽烷、雙(三乙氧基矽烷基丙基)四硫醚、3-異氰酸酯丙基三乙氧基矽烷等。
又,矽烷之具體例子,可列舉甲基三氯矽
烷、二甲基二氯矽烷、三甲基氯矽烷、苯基三氯矽烷、甲基三甲氧基矽烷、二甲基二甲氧基矽烷、苯基三甲氧基矽烷、甲基三乙氧基矽烷、甲基三乙氧基矽烷、二甲基二乙氧基矽烷苯基三乙氧基矽烷、n-丙基三甲氧基矽烷、n-丙基三乙氧基矽烷、己基三甲氧基矽烷、己基三乙氧基矽烷、癸基三甲氧基矽烷、三氟丙基三甲氧基矽烷、六甲基二矽氮烷等。
上述有機金屬化合物,可列舉鈦酸酯系偶合劑或鋁系偶合劑,鈦酸酯系偶合劑之具體例子,可列舉PLENACT KR TTS、KR 46B、KR 38B、KR 138S、KR238S、338X、KR 44、KR 9SA、KR ET5、KR ET(味之素Fine-Techno(股)製);鋁系偶合劑之具體例子,可列舉PLENACT AL-M(味之素Fine-Techno(股)製)等。
此等有機矽化合物、有機金屬化合物之使用量,相對於上述無機微粒子100質量份而言,較佳為2~100質量份。
有機無機複合光擴散劑,可列舉例如三聚氰胺樹脂/二氧化矽複合粒子等。如此之有機無機複合光擴散劑之市售品,可列舉例如三聚氰胺樹脂/二氧化矽複合粒子的Optobeads(註冊商標)500S(日產化學工業(股)製)等。
該三聚氰胺樹脂/二氧化矽複合粒子等之有機無機複合光擴散劑,較佳為以表面修飾劑處理後使用。
此時,作為表面修飾劑者,只要係可提高基質樹脂與光擴散劑之相溶性者,並無特殊限定,但考慮到基質樹脂為含有三嗪環之聚合物時,較佳為合併使用矽烷偶合劑及具有(甲基)丙烯酸基與異氰酸酯基之化合物的2成分。
矽烷偶合劑並無特殊限定,例如可適合使用具有胺基者、具有硫醇基者等,其中尤以具有胺基之矽烷偶合劑較佳。
具有胺基之矽烷偶合化劑,可列舉例如3-胺基丙基三甲氧基矽烷、3-胺基丙基三乙氧基矽烷、3-胺基丙基甲基二甲氧基矽烷、3-胺基丙基二甲基甲氧基矽烷、3-胺基丙基甲基二乙氧基矽烷、3-胺基丙基二甲基乙氧基矽烷、N-苯基-3-胺基丙基三甲氧基矽烷、N-苯基-3-胺基丙基三乙氧基矽烷等。
具有硫醇基之矽烷偶合化劑,可列舉例如3-巰基丙基三甲氧基矽烷、3-巰基丙基三乙氧基矽烷、巰基甲基二甲基乙氧基矽烷、(巰基甲基)甲基二乙氧基矽烷、3-巰基丙基甲基二甲氧基矽烷等。
作為具有(甲基)丙烯酸基與異氰酸酯基之化合物者,亦只要係具有此等兩官能基者,則無特殊限定。
其具體例子,可列舉丙烯酸2-異氰酸基乙酯、甲基丙烯酸2-異氰酸基乙酯、異氰酸1,1-(雙丙烯醯氧基甲基)乙酯、或將該等之異氰酸酯基嵌段化而得的化合物等。
如此化合物之市售品,可列舉丙烯酸2-異氰酸基乙酯
的Karenz AOI(註冊商標)、甲基丙烯酸2-異氰酸基乙酯的Karenz MOI(註冊商標)、異氰酸1,1-(雙丙烯醯氧基甲基)乙酯的Karenz BEI(註冊商標)、甲基丙烯酸2-(O-[1’-甲基亞丙基胺基]羧基胺基)乙酯的Karenz MOI-BM(註冊商標,Karenz MOI之嵌段化異氰酸酯化合物)、甲基丙烯酸2-[(3,5-二甲基吡唑基)羰基胺基]乙酯的Karenz MOI-BP(註冊商標,Karenz MOI之嵌段化異氰酸酯化合物)、Karenz MOI-EG(註冊商標)(均為昭和電工(股)製)等。
表面修飾法並無特殊限定,只要適當採用以往周知之方法即可,可列舉例如將有機無機複合光擴散劑、矽烷偶合劑、以及具有(甲基)丙烯酸基及異氰酸酯基之化合物,於適當溶劑中混合並加熱攪拌之方法。
此時,矽烷偶合劑與具有(甲基)丙烯酸基及異氰酸酯基的化合物之使用比率,較佳為矽烷偶合劑中之胺基或硫醇基(以下稱為活性氫基)、與具有(甲基)丙烯酸基及異氰酸酯基之化合物中的異氰酸酯基(以下稱為NCO基)之莫耳比,為活性氫基/NCO=0.1/10~15/10之範圍、特別適合為1/1。
又,相對於光擴散劑而言,表面處理劑之使用量,相對於光擴散劑100質量份,以表面處理劑之總量計,較佳為1~150質量份、更佳為10~100質量份。
作為溶劑者,只要係具有粒子之分散能力者即可,可列舉例如水、甲苯、p-二甲苯、o-二甲苯、m-二
甲苯、乙苯、苯乙烯、乙二醇二甲基醚、丙二醇單甲基醚、乙二醇單甲基醚、丙二醇、丙二醇單乙基醚、乙二醇單乙基醚、乙二醇單異丙基醚、乙二醇甲基醚乙酸酯、丙二醇單甲基醚乙酸酯、乙二醇乙基醚乙酸酯、二乙二醇二甲基醚、丙二醇單丁基醚、乙二醇單丁基醚、二乙二醇二乙基醚、二丙二醇單甲基醚、二乙二醇單甲基醚、二丙二醇單乙基醚、二乙二醇單乙基醚、三乙二醇二甲基醚、二乙二醇單乙基醚乙酸酯、二乙二醇、1-辛醇、乙二醇、己二醇、三亞甲二醇、1-甲氧基-2-丁醇、環己醇、二丙酮醇、呋喃甲醇、四氫呋喃甲醇、丙二醇、苄基醇、1,3-丁二醇、1,4-丁二醇、2,3-丁二醇、γ-丁內酯、丙酮、甲基乙基酮、甲基異丙基酮、二乙基酮、甲基異丁基酮、甲基正丁基酮、環戊酮、環己酮、乙酸乙酯、乙酸異丙酯、乙酸正丙酯、乙酸異丁酯、乙酸正丁酯、乳酸乙酯、甲醇、乙醇、異丙醇、tert-丁醇、烯丙醇、正丙醇、2-甲基-2-丁醇、異丁醇、正丁醇、2-甲基-1-丁醇、1-戊醇、2-甲基-1-戊醇、2-乙基己醇、1-甲氧基-2-丙醇、四氫呋喃、1,4-二噁烷、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺(DMAc)、N-甲基吡咯啶酮、1,3-二甲基-2-四氫咪唑酮、二甲基亞碸、N-環己基-2-四氫吡咯酮等,此等可單獨使用、亦可混合2種以上使用。
表面處理後,可將經表面處理之光擴散劑取出使用、亦可以分散液的形式直接使用。以分散液的形式使用時,其固體成分濃度並無特殊限定,可為0.1~50質
量%左右。
上述表面修飾時,為了更加提高所得表面修飾光擴散劑之分散性,亦可將表面修飾前之光擴散劑預先分散於上述溶劑,配製分散液,且於該分散液中添加表面修飾劑來進行表面修飾。
作為分散處理法者,並無特殊限定,可使用超音波處理、濕式噴射磨機處理等。
此時之分散液之固體成分濃度亦無特殊限定,可為0.1~50質量%左右。
有機光擴散劑,可列舉交聯聚甲基丙烯酸甲酯(PMMA)粒子、交聯聚甲基丙烯酸酯粒子、交聯聚苯乙烯粒子、交聯苯乙烯丙烯酸共聚合粒子、三聚氰胺-甲醛粒子、聚矽氧樹脂粒子、二氧化矽‧丙烯酸複合粒子、耐綸粒子、苯并胍胺-甲醛粒子、苯并胍胺/三聚氰胺/甲醛粒子、氟樹脂粒子、環氧樹脂粒子、聚苯硫樹脂粒子、聚醚碸樹脂粒子、聚丙烯腈粒子、聚胺基甲酸酯粒子等。如此之有機光擴散劑的市售品,可列舉交聯PMMA粒子的MX-150(綜研化學(股)製)、Techpolymer SSX系列(積水化成(股)製)、Taftic(註冊商標)FH-S系列(東洋紡績(股)製)、交聯苯乙烯-丙烯酸系中空粒子(NANOTEX,JSR(股)製)、聚矽氧樹脂粒子的Tospearl系列(Momentive製)、KMP系列(信越化學工業(股)製)、聚苯乙烯系及聚甲基丙烯酸酯系粒子的Ganz Pearl系列(Ganz化成(股)製)、二氧化矽/丙烯
酸複合粒子的Soliostar RA、SP((股)日本觸媒製)、耐綸粒子的Amilan(東麗(股)製)、苯并胍胺-甲醛粒子的Epostar MS、M05、L15((股)日本觸媒製)、苯并胍胺/三聚氰胺/甲醛粒子的Epostar M30((股)日本觸媒製)、氟樹脂粒子的Fluon PTFE分散液(旭硝子(股)製)、環氧樹脂粒子的Torepearl EP(東麗(股)製)、聚苯硫樹脂粒子的Torepearl PPS(東麗(股)製)、聚醚碸樹脂粒子的Torepearl PES(東麗(股)製)、聚丙烯腈粒子的Taftic F系列F-120(東洋紡(股)製)、聚胺基甲酸酯粒子的Artperl(交聯胺基甲酸酯珠MM,根上工業(股)製)等。
無機光擴散劑,可列舉碳酸鈣(CaCO3)、氧化鈦(TiO2)、硫酸鋇(BaSO4)、氫氧化鋁(Al(OH)3)、二氧化矽(SiO2)、滑石等,但由更提高所得硬化膜之光擴散性的觀點而言,較佳為氧化鈦(TiO2)或凝集二氧化矽粒子、更佳為非凝集性之氧化鈦(TiO2),並無特殊限定,其中尤以經3-丙烯醯氧基丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-丙烯醯氧基丙基三乙氧基矽烷、3-甲基丙烯醯氧基丙基三乙氧基矽烷、3-丙烯醯氧基丙基甲基二甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷、3-丙烯醯氧基丙基二甲基甲氧基矽烷、3-甲基丙烯醯氧基丙基二甲基甲氧基矽烷、3-丙烯醯氧基丙基甲基二乙氧基矽烷、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷、3-丙烯醯氧基丙基二甲基
乙氧基矽烷、3-甲基丙烯醯氧基丙基二甲基乙氧基矽烷等之含有(甲基)丙烯醯氧基之三烷氧基矽烷表面修飾劑表面處理者為適宜。
此等表面修飾劑之使用量並無特殊限定,較佳為氧化鈦(TiO2)或二氧化矽粒子表面之每1nm2,表面修飾劑成為1.0~5.0個左右的量。
表面修飾法並無特殊限定,只要適當採用以往周知之方法即可。
又,考慮到提高於基質樹脂的含有三嗪環之聚合物中的分散性時,氧化鈦(TiO2)或凝集二氧化矽粒子,較佳為作為有機溶劑分散液來使用。此時,有機溶劑並無特殊限定,可列舉上述有機無機複合光擴散劑之表面處理用溶劑中所例示的有機溶劑等,作為氧化鈦之分散液配製用溶劑,較佳為丙酮、甲基乙基酮、甲基異丙基酮、二乙基酮、甲基異丁基酮、甲基正丁基酮、環己酮等之酮系溶劑,作為凝集二氧化矽之分散液配製用溶劑,較佳為乙二醇二甲基醚、丙二醇單甲基醚、乙二醇單甲基醚、丙二醇、丙二醇單乙基醚、乙二醇單乙基醚、乙二醇單異丙基醚、乙二醇甲基醚乙酸酯、丙二醇單甲基醚乙酸酯、乙二醇乙基醚乙酸酯、二乙二醇二甲基醚、丙二醇單丁基醚、乙二醇單丁基醚、二乙二醇二乙基醚、二丙二醇單甲基醚、二乙二醇單甲基醚、二丙二醇單乙基醚、二乙二醇單乙基醚、三乙二醇二甲基醚、二乙二醇單乙基醚乙酸酯等之二醇醚系溶劑。
其固體成分濃度並無特殊限定,可為0.1~50質量%左右。
再者,凝集二氧化矽粒子之市售品,可列舉凝集二氧化矽粒子之鹼性分散液的Light Star LA-S26(日產化學工業(股)製)、Light Star LA-OS20PGM(日產化學工業(股)製)等,可經適當方法進行溶劑取代來使用。
上述各光擴散劑之中,考慮到提高所得硬化膜之光擴散性時,尤以氧化鈦(TiO2)較佳,進而亦考慮到氧化鈦分散液之分散安定性提高或過濾性等之作業性提高等時,最適宜為經含有(甲基)丙烯醯氧基之三烷氧基矽烷表面修飾劑表面處理的非凝集性氧化鈦(TiO2)。
光擴散劑之平均粒子徑並無特殊限定,但由更加提高分散性,而且將所得硬化膜予以更加薄膜化、及更加提高硬化膜之平坦性的觀點而言,較佳為3μm以下、更佳為2μm以下、又更佳為1μm以下。又,由使所得之硬化膜發揮充分的光擴散性之觀點而言,較佳為100nm以上、更佳為150nm以上、又更佳為200nm以上。
再者,平均粒子徑(μm),係基於Mie理論,以雷射繞射/散射法測定所得之50%體積直徑(中位直徑),例如可藉由Malvern Instruments公司製Mastersizer(註冊商標)2000等來測定。
光擴散劑之使用量並無特殊限定,但考慮到更加提高所得硬化膜之光散射效率時,相對於含有三嗪環
之聚合物100質量份而言,其下限較佳為1質量份、更佳為5質量份、又更佳為30質量份,考慮到抑制硬化膜之光透過率降低、或抑制製膜性之降低等時,其上限較佳為250質量份、更佳為200質量份、又更佳為150質量份。
本發明所用之光散射膜形成用組成物中,較佳為添加各種溶劑,將含有三嗪環之聚合物溶解來使用。
此時,溶劑可為與聚合時所使用的溶劑相同者,亦可為不同者。該溶劑只要係不損及與聚合物之相溶性則無特殊限定,可任意選擇1種或複數種來使用。
如此溶劑之具體例子,可列舉與於上述光擴散劑之表面修飾所使用之溶劑中所例示者相同者。
此時,光散射膜形成組成物中之固體成分濃度,只要係不對保存安定性造成影響的範圍,則無特殊限定,只要依目標之膜厚度來適當設定即可。具體而言,由溶解性及保存安定性之觀點而言,較佳為固體成分濃度0.1~50質量%、更佳為0.1~40質量%。
本發明所用之光散射膜形成用組成物中,只要不損及本發明之效果,亦可包含含有三嗪環之聚合物、交聯劑、光擴散劑及溶劑以外之其他成分,例如調平劑、界面活性劑等。
界面活性劑可列舉例如聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、聚氧乙烯鯨蠟基醚、聚氧乙烯油醯基醚等之聚氧乙烯烷基醚類;聚氧乙烯辛基酚醚、聚氧乙烯壬基酚醚等之聚氧乙烯烷基烯丙基醚類;聚氧乙烯/聚氧丙烯嵌段
共聚物類;山梨醇酐單月桂酸酯、山梨醇酐單棕櫚酸酯、山梨醇酐單硬脂酸酯、山梨醇酐單油酸酯、山梨醇酐三油酸酯、山梨醇酐三硬脂酸酯等之山梨醇酐脂肪酸酯類;聚氧乙烯山梨醇酐單月桂酸酯、聚氧乙烯山梨醇酐單棕櫚酸酯、聚氧乙烯山梨醇酐單硬脂酸酯、聚氧乙烯山梨醇酐三油酸酯、聚氧乙烯山梨醇酐三硬脂酸酯等之聚氧乙烯山梨醇酐脂肪酸酯類等之非離子系界面活性劑;商品名Eftop EF301、EF303、EF352(三菱材料電子化成(股)(舊(股)Jemco)製)、商品名Megafac F171、F173、R-08、R-30、R-40、F-553、F-554、RS-75、RS-72-K(DIC(股)製)、FLUORAD FC430、FC431(住友3M(股)製)、商品名AsahiGuard AG710,Surflon S-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(股)製)等之氟系界面活性劑、有機矽氧烷聚合物KP341(信越化學工業(股)製)、BYK-302、BYK-307、BYK-322、BYK-323、BYK-330、BYK-333、BYK-370、BYK-375、BYK-378(BYK Japan(股)製)等。
此等之界面活性劑,可單獨使用、亦可組合2種以上使用。界面活性劑之使用量,相對於含有三嗪環之聚合物100質量份而言,較佳為0.0001~5質量份、更佳為0.001~1質量份、又更佳為0.01~0.5質量份。
再者,上述其他成分,可於配製本發明之組成物時的任意步驟添加。
將上述光散射膜形成用組成物,塗佈於基
材,之後依需要加熱使溶劑蒸發後,加熱或光照射,可成為所期望之硬化膜。
組成物之塗佈方法係為任意,例如可採用旋轉塗佈法、浸漬法、流動塗佈法、噴墨法、噴霧法、棒塗佈法、凹版塗佈法、狹縫塗佈法、輥塗佈法、轉印印刷法、刷毛塗佈、刮刀塗佈法、氣刀塗佈法、網版印刷法等之方法。
又,基材可列舉矽、成膜有銦錫氧化物(ITO)之玻璃、成膜有銦鋅氧化物(IZO)之玻璃、聚對苯二甲酸乙二酯(PET)、塑膠、玻璃、石英、陶瓷等所成之基材等,亦可使用具有可撓性之可撓基材。
燒成溫度以使溶劑蒸發為目的則無特殊限定,例如可於40~400℃進行。
燒成方法並無特殊限定,例如使用加熱板或烘箱,於大氣、氮等之惰性氣體、真空中等之適切環境下使溶劑蒸發即可。
燒成溫度及燒成時間,只要選擇適合於目標之電子裝置的製程步驟之條件即可,且只要選擇所得之膜的物性值符合於電子裝置的要求特性之燒成條件即可。
光照射時的條件亦無特殊限定,只要依照所用之含有三嗪環之聚合物及交聯劑,採用適宜的照射能量及時間即可。
如此方式所得之本發明之硬化膜,可達成高耐熱性、高透明性、高折射率、高溶解性、及低體積收縮,因此可適合利用作為製作液晶顯示器、有機EL元件
(有機EL顯示器或有機EL照明)、光半導體(LED)元件、固體攝影元件、有機薄膜太陽電池、色素增感太陽電池、有機薄膜電晶體(TFT)等電子裝置時的一構件,特別地,因光擴散性優良,因此可適合利用作為有機EL元件或LED元件之光散射層(光提取層)用材料。
再者,為了更加提高所得硬化膜之平坦性,亦可由上述光散射膜形成用組成物中,以光擴散劑以外的組成物作為平坦化材料,使用其於上述硬化膜(光散射膜)之上進一步層合平坦化膜。
該平坦化材料中,含有三嗪環之聚合物或交聯劑等之具體例、或者該等之摻合量、及膜形成方法,係如上所述。
藉由將上述硬化膜使用作為有機EL元件之光提取膜,可得到有機EL元件之電流效率(光提取效率)良好的元件。
作為光提取膜使用時,係製作具有上述硬化膜之電極基板,且於其上層合各種機能層,作為有機EL元件。
若列舉一例,係於玻璃等之基材上,使用上述光散射膜形成用組成物,以上述方法形成硬化膜,進一步於其上,以RF濺鍍法等之通常方法,形成作為陽極材料的ITO或IZO膜,以製作陽極基板。
使用該陽極基板,來製作低分子系有機電致發光(OLED)元件、或高分子系有機電致發光(PLED)元件即可。
製作OLED元件時的使用材料或製作方法,可列舉如下述者,但不限定於此等。
所使用之電極基板,較佳為預先以洗劑、醇、純水等進行液體洗淨而予以清潔,例如於陽極基板,較佳為於剛要使用前進行UV臭氧處理、氧-電漿處理等之表面處理。惟陽極材料以有機物為主成分時,亦可不進行表面處理。
於電極上使電洞注入層、電洞輸送層、發光層、電子輸送層、電子輸送層/電洞阻擋層、陰極金屬成膜,作為OLED元件。再者,亦可依需要,於發光層與電洞輸送層之間設置電子阻擋層。
陽極材料可列舉以銦錫氧化物(ITO)、銦鋅氧化物(IZO)為代表之透明電極、或以鋁為代表之金屬或此等之合金等所構成的金屬陽極,較佳為進行過平坦化處理者。亦可使用具有高電荷輸送性之聚噻吩衍生物或聚苯胺衍生物。
再者,作為構成金屬陽極之其他金屬者,可列舉鈧、鈦、釩、鉻、錳、鐵、鈷、鎳、銅、鋅、鎵、釔、鋯、鈮、鉬、釕、銠、鈀、鎘、銦、鈧、鑭、鈰、鐠、釹、鉕、釤、銪、釓、鋱、鏑、鈥、鉺、銩、鐿、鉿、鉈、鎢、錸、鋨、銥、鉑、金、鈦、鉛、鉍或此等之合金等,但不限定於此等。
作為形成電洞注入層及電洞輸送層之材料者,可列舉(三苯基胺)二聚物衍生物、[(三苯基胺)
二聚物]螺二聚物、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-聯苯胺(α-NPD)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-聯苯胺、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-聯苯胺、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-螺聯茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-螺聯茀、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-二甲基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-二甲基-茀、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-二苯基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-二苯基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-2,2’-二甲基聯苯胺、2,2’,7,7’-肆(N,N-二苯基胺基)-9,9-螺聯茀、9,9-雙[4-(N,N-雙-聯苯基-4-基-胺基)苯基]-9H-茀、9,9-雙[4-(N,N-雙-萘-2-基-胺基)苯基]-9H-茀、9,9-雙[4-(N-萘-1-基-N-苯基胺基)-苯基]-9H-茀、2,2’,7,7’-肆[N-萘基(苯基)-胺基]-9,9-螺聯茀、N,N’-雙(菲-9-基)-N,N’-雙(苯基)-聯苯胺、2,2’-雙[N,N-雙(聯苯基-4-基)胺基]-9,9-螺聯茀、2,2’-雙(N,N-二苯基胺基)-9,9-螺聯茀、二-[4-(N,N-二(p-甲苯基)胺基)-苯基]環己烷、2,2’,7,7’-四(N,N-二(p-甲苯基))胺基-9,9-螺聯茀、N,N,N’,N’-四-萘-2-基-聯苯胺、N,N,N’,N’-四-(3-甲基苯基)-3,3’-二甲基聯苯胺、N,N’-二(萘基)-N,N’-二(萘-2-基)-聯苯胺、N,N,N’,N’-四(萘基)-聯苯胺、N,N’-二(萘-2-基)-N,N’-二苯基聯苯胺-1,4-二胺、N1,N4-二苯基-N1,N4-二(m-甲苯基)苯-1,4-二胺、N2,N2,N6,N6-四苯基萘-2,6-
二胺、參(4-(喹啉-8-基)苯基)胺、2,2’-雙(3-(N,N-二(p-甲苯基)胺基)苯基)聯苯、4,4’,4”-參[3-甲基苯基(苯基)胺基]三苯基胺(m-MTDATA)、4,4’,4”-參[1-萘基(苯基)胺基]三苯基胺(1-TNATA)等之三芳基胺類、5,5”-雙-{4-[雙(4-甲基苯基)胺基]苯基}-2,2’:5’,2”-聯三噻吩(BMA-3T)等之寡聚噻吩類等之電洞輸送性低分子材料等。
作為形成發光層之材料者,可列舉參(8-羥基喹啉)鋁(III)(Alq3)、雙(8-羥基喹啉)鋅(II)(Znq2)、雙(2-甲基-8-羥基喹啉)-4-(p-苯基酚)鋁(III)(BAlq)、4,4’-雙(2,2-二苯基乙烯基)聯苯、9,10-二(萘-2-基)蒽、2-t-丁基-9,10-二(萘-2-基)蒽、2,7-雙[9,9-二(4-甲基苯基)-茀-2-基]-9,9-二(4-甲基苯基)茀、2-甲基-9,10-雙(萘-2-基)蒽、2-(9,9-螺聯茀-2-基)-9,9-螺聯茀、2,7-雙(9,9-螺聯茀-2-基)-9,9-螺聯茀、2-[9,9-二(4-甲基苯基)-茀-2-基]-9,9-二(4-甲基苯基)茀、2,2’-二芘基-9,9-螺聯茀、1,3,5-參(芘-1-基)苯、9,9-雙[4-(芘基)苯基]-9H-茀、2,2’-聯(9,10-二苯基蒽)、2,7-二芘基-9,9-螺聯茀、1,4-二(芘-1-基)苯、1,3-二(芘-1-基)苯、6,13-二(聯苯-4-基)稠五苯、3,9-二(萘-2-基)苝、3,10-二(萘-2-基)苝、參[4-(芘基)-苯基]胺、10,10’-二(聯苯-4-基)-9,9’-聯蒽、N,N’-二(萘-1-基)-N,N’-二苯基-[1,1’:4’,1”:4”,1”’-聯四苯基]-4,4”’-二胺、4,4’-二[10-(萘-1-基)蒽-9-基]聯苯、二
苯并{[f,f’]-4,4’,7,7’-四苯基}二茚并[1,2,3-cd:1’,2’,3’-lm]苝、1-(7-(9,9’-聯蒽-10-基)-9,9-二甲基-9H-茀-2-基)芘、1-(7-(9,9’-聯蒽-10-基)-9,9-二己基-9H-茀-2-基)芘、1,3-雙(咔唑-9-基)苯、1,3,5-參(咔唑-9-基)苯、4,4’,4”-參(咔唑-9-基)三苯基胺、4,4’-雙(咔唑-9-基)聯苯(CBP)、4,4’-雙(咔唑-9-基)-2,2’-二甲基聯苯、2,7-雙(咔唑-9-基)-9,9-二甲基茀、2,2’,7,7’-肆(咔唑-9-基)-9,9-螺聯茀、2,7-雙(咔唑-9-基)-9,9-二(p-甲苯基)茀、9,9-雙[4-(咔唑-9-基)-苯基]茀、2,7-雙(咔唑-9-基)-9,9-螺聯茀、1,4-雙(三苯基矽烷基)苯、1,3-雙(三苯基矽烷基)苯、雙(4-N,N-二乙基胺基-2-甲基苯基)-4-甲基苯基甲烷、2,7-雙(咔唑-9-基)-9,9-二辛基茀、4,4”-二(三苯基矽烷基)-p-聯三苯基、4,4’-二(三苯基矽烷基)聯苯、9-(4-t-丁基苯基)-3,6-雙(三苯基矽烷基)-9H-咔唑、9-(4-t-丁基苯基)-3,6-二-三苯甲基-9H-咔唑、9-(4-t-丁基苯基)-3,6-雙(9-(4-甲氧基苯基)-9H-茀-9-基)-9H-咔唑、2,6-雙(3-(9H-咔唑-9-基)苯基)吡啶、三苯基(4-(9-苯基-9H-茀-9-基)苯基)矽烷、9,9-二甲基-N,N-二苯基-7-(4-(1-苯基-1H-苯并[d]咪唑-2-基)苯基)-9H-茀-2-胺、3,5-雙(3-(9H-咔唑-9-基)苯基)吡啶、9,9-螺聯茀-2-基-二苯基-膦氧化物、9,9’-(5-(三苯基矽烷基)-1,3-伸苯基)雙(9H-咔唑)、3-(2,7-雙(二苯基磷氧基)-9-苯基-9H-茀-9-基)-9-苯基-9H-咔唑、4,4,8,8,12,12-六(p-甲苯基)-4H-8H-
12H-12C-氮雜二苯并[cd,mn]芘、4,7-二(9H-咔唑-9-基)-1,10-啡啉、2,2’-雙(4-(咔唑-9-基)苯基)聯苯、2,8-雙(二苯基磷氧基)二苯并[b,d]噻吩、雙(2-甲基苯基)二苯基矽烷、雙[3,5-二(9H-咔唑-9-基)苯基]二苯基矽烷、3,6-雙(咔唑-9-基)-9-(2-乙基-己基)-9H-咔唑、3-(二苯基磷氧基)-9-(4-(二苯基磷氧基)苯基)-9H-咔唑、3,6-雙[(3,5-二苯基)苯基]-9-苯基咔唑等,亦可藉由與發光性摻雜劑共蒸鍍,來形成發光層。
作為發光性摻雜劑者,可列舉3-(2-苯并噻唑基)-7-(二乙基胺基)香豆素、2,3,6,7-四氫-1,1,7,7-四甲基-1H,5H,11H-10-(2-苯并噻唑基)唑嗪并[9,9a,1gh]香豆素、喹吖酮、N,N’-二甲基-喹吖酮、參(2-苯基吡啶)銥(III)(Ir(ppy)3)、雙(2-苯基吡啶)(乙醯基丙酮酸)銥(III)(Ir(ppy)2(acac))、參[2-(p-甲苯基)吡啶]銥(III)(Ir(mppy)3)、9,10-雙[N,N-二(p-甲苯基)胺基]蒽、9,10-雙[苯基(m-甲苯基)胺基]蒽、雙[2-(2-羥基苯基)苯并噻唑基]鋅(II)、N10,N10,N10’,N10’-四(p-甲苯基)-9,9’-聯蒽-10,10’-二胺、N10,N10,N10’,N10’-四苯基-9,9’-聯蒽-10,10’-二胺、N10,N10’-二苯基-N10,N10’-二萘基-9,9’-聯蒽-10,10’-二胺、4,4’-雙(9-乙基-3-咔唑伸乙烯基)-1,1’-聯苯、苝、2,5,8,11-四-t-丁基苝、1,4-雙[2-(3-N-乙基咔唑基)乙烯基]苯、4,4’-雙[4-(二-p-甲苯基胺基)苯乙烯基]聯苯、4-(二-p-甲苯基胺基)-4’-[(二-p-甲苯基胺基)苯乙烯基]二苯乙烯、雙[3,5-二氟-2-(2-
吡啶基)苯基-(2-羧基吡啶基)]銥(III)、4,4’-雙[4-(二苯基胺基)苯乙烯基]聯苯、雙(2,4-二氟苯基吡啶根)肆(1-吡唑基)硼酸鹽銥(III)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-參(9,9-二甲基伸茀基)、2,7-雙{2-[苯基(m-甲苯基)胺基]-9,9-二甲基-茀-7-基}-9,9-二甲基-茀、N-(4-((E)-2-(6((E)-4-(二苯基胺基)苯乙烯基)萘-2-基)乙烯基)苯基)-N-苯基苯胺、fac-銥(III)參(1-苯基-3-甲基苯并咪唑啉-2-亞基-C,C2’)、mer-銥(III)參(1-苯基-3-甲基苯并咪唑啉-2-亞基-C,C2’)、2,7-雙[4-(二苯基胺基)苯乙烯基]-9,9-螺聯茀、6-甲基-2-(4-(9-(4-(6-甲基苯并[d]噻唑-2-基)苯基)蒽-10-基)苯基)苯并[d]噻唑、1,4-二[4-(N,N-二苯基)胺基]苯乙烯基苯、1,4-雙(4-(9H-咔唑-9-基)苯乙烯基)苯、(E)-6-(4-(二苯基胺基)苯乙烯基)-N,N-二苯基萘-2-胺、雙(2,4-二氟苯基吡啶根)(5-(吡啶-2-基)-1H-四唑)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑)((2,4-二氟苄基)二苯基亞膦酸)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑)(苄基二苯基亞膦酸)銥(III)、雙(1-(2,4-二氟苄基)-3-甲基苯并咪唑鎓)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑)(4’,6’-二氟苯基吡啶)銥(III)、雙(4’,6’-二氟苯基吡啶根)(3,5-雙(三氟甲基)-2-(2’-吡啶基)吡咯)銥(III)、雙(4’,6’-二氟苯基吡啶根)(3-(三氟甲基)-
5-(2-吡啶基)-1,2,4-三唑)銥(III)、(Z)-6-均三甲苯基-N-(6-均三甲苯基喹啉-2(1H)-亞基)喹啉-2-胺-BF2、(E)-2-(2-(4-(二甲基胺基)苯乙烯基)-6-甲基-4H-吡喃-4-亞基)丙二腈、4-(二氰基亞甲基)-2-甲基-6-久咯啶基-9-烯基-4H-吡喃、4-(二氰基亞甲基)-2-甲基-6-(1,1,7,7-四甲基久咯啶基-9-烯基)-4H-吡喃、4-(二氰基亞甲基)-2-t-丁基-6-(1,1,7,7-四甲基久咯啶-4-基-乙烯基)-4H-吡喃、參(二苄醯基甲烷)啡啉銪(III)、5,6,11,12-四苯基稠四苯、雙(2-苯并[b]噻吩-2-基-吡啶)(乙醯基丙酮酸)銥(III)、參(1-苯基異喹啉)銥(III)、雙(1-苯基異喹啉)(乙醯基丙酮酸)銥(III)、雙[1-(9,9-二甲基-9H-茀-2-基)-異喹啉](乙醯基丙酮酸)銥(III)、雙[2-(9,9-二甲基-9H-茀-2-基)喹啉](乙醯基丙酮酸)銥(III)、參[4,4’-二-t-丁基-(2,2’)-聯吡啶]釕(III)/雙(六氟磷酸鹽)、參(2-苯基喹啉)銥(III)、雙(2-苯基喹啉)(乙醯基丙酮酸)銥(III)、2,8-二-t-丁基-5,11-雙(4-t-丁基苯基)-6,12-二苯基稠四苯、雙(2-苯基苯并噻唑基)(乙醯基丙酮酸)銥(III)、5,10,15,20-四苯基四苯并卟啉鉑、鋨(II)雙(3-三氟甲基-5-(2-吡啶)-吡唑)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三唑)二苯基甲基膦、鋨(II)雙(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三唑)二
甲基苯基膦、雙[2-(4-n-己基苯基)喹啉](乙醯基丙酮酸)銥(III)、參[2-(4-n-己基苯基)喹啉]銥(III)、參[2-苯基-4-甲基喹啉]銥(III)、雙(2-苯基喹啉)(2-(3-甲基苯基)吡啶)銥(III)、雙(2-(9,9-二乙基-茀-2-基)-1-苯基-1H-苯并[d]咪唑基)(乙醯基丙酮酸)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-苯并哌喃-2-酮酸)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮酸)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮酸)銥(III)、銥(III)雙(4-苯基噻吩并[3,2-c]吡啶根-N,C2’)乙醯基丙酮酸鹽、(E)-2-(2-t-丁基-6-(2-(2,6,6-三甲基-2,4,5,6-四氫-1H-吡咯并[3,2,1-ij]喹啉-8-基)乙烯基)-4H-吡喃-4-亞基)丙二腈、雙(3-三氟甲基-5-(1-異喹啉基)吡唑)(甲基二苯基膦)釕、雙[(4-n-己基苯基)異喹啉](乙醯基丙酮酸)銥(III)、鉑(II)八乙基卟吩、雙(2-甲基二苯并[f,h]喹噁啉)(乙醯基丙酮酸)銥(III)、參[(4-n-己基苯基)氧代喹啉]銥(III)等。
作為形成電子輸送層/電洞阻擋層之材料者,可列舉8-羥基喹啉醇化物-鋰、2,2’,2”-(1,3,5-石油醚甲苯基)-參(1-苯基-1-H-苯并咪唑)、2-(4-聯苯基)5-(4-t-丁基苯基)-1,3,4-噁二唑、2,9-二甲基-4,7-二苯基-1,10-啡啉、4,7-二苯基-1,10-啡啉、雙(2-甲基-8-喹啉醇化物)-4-(苯基酚)鋁、1,3-雙[2-(2,2’-聯吡啶-6-基)-1,3,4-噁二唑-5-基]苯、6,6’-雙[5-(聯苯基-4-基)-1,3,4-
噁二唑-2-基]-2,2’-聯吡啶、3-(4-聯苯基)-4-苯基-5-t-丁基苯基-1,2,4-三唑、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-三唑、2,9-雙(萘-2-基)-4,7-二苯基-1,10-啡啉、2,7-雙[2-(2,2’-聯吡啶-6-基)-1,3,4-噁二唑-5-基]-9,9-二甲基茀、1,3-雙[2-(4-t-丁基苯基)-1,3,4-噁二唑-5-基]苯、參(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、1-甲基-2-(4-(萘-2-基)苯基)-1H-咪唑并[4,5f][1,10]啡啉、2-(萘-2-基)-4,7-二苯基-1,10-啡啉、苯基-二芘基膦氧化物、3,3’,5,5’-四[(m-吡啶基)-吩-3-基]聯苯(3,3’,5,5’-tetra[(m-pyridyl)-phen-3-yl]biphenyl)、1,3,5-參[(3-吡啶基)-吩-3-基]苯(1,3,5-tris[(3-pyridyl)-phen-3-yl]benzene)、4,4’-雙(4,6-二苯基-1,3,5-三嗪-2-基)聯苯、1,3-雙[3,5-二(吡啶-3-基)苯基]苯、雙(10-羥基苯并[h]喹啉基)鈹、二苯基雙(4-(吡啶-3-基)苯基)矽烷、3,5-二(芘-1-基)吡啶等。
作為形成電子注入層之材料者,可列舉氧化鋰(Li2O)、氧化鎂(MgO)、氧化鋁(Al2O3)、氟化鋰(LiF)、氟化鈉(NaF)、氟化鎂(MgF2)、氟化銫(CsF)、氟化鍶(SrF2)、三氧化鉬(MoO3)、鋁、Li(acac)、乙酸鋰、安息香酸鋰等。
作為陰極材料者,可列舉鋁、鎂-銀合金、鋁-鋰合金、鋰、鈉、鉀、銫等。
作為形成電子阻擋層之材料者,可列舉參(苯基吡唑)銥等。
PLED元件之製作方法並無特殊限定,可列舉以下之方法。
上述OLED元件製作中,藉由依次形成電洞輸送性高分子層、發光性高分子層,以取代使電洞輸送層、發光層、電子輸送層、電子注入層成膜,可製作PLED元件。
所使用之陰極及陽極材料,可使用與上述OLED元件製作時相同者,且可進行同樣之洗淨處理、表面處理。
作為電洞輸送性高分子層及發光性高分子層之形成方法者,可列舉對電洞輸送性高分子材料或發光性高分子材料、或於此等中添加有摻雜劑物質的材料添加溶劑進行溶解,或均勻地分散,於電洞注入層或電洞輸送性高分子層之上塗佈後,分別進行燒成藉以成膜的方法。
電洞輸送性高分子材料,可列舉聚[(9,9-二己基茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[(9,9-二辛基茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,1’-伸聯苯基-4,4-二胺)]、聚[(9,9-雙{1’-戊烯-5’-基}茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[N,N’-雙(4-丁基苯基)-N,N’-雙(苯基)-聯苯胺]-以聚倍半矽氧烷封端(end capped with polysilsesquioxane)、聚[(9,9-二辛基茀基-2,7-二基)-co-(4,4’-(N-(p-丁基苯基))二苯基胺)]等。
發光性高分子材料,可列舉聚(9,9-二烷基
茀)(PDAF)等之聚茀衍生物、聚(2-甲氧基-5-(2’-乙基六氧)-1,4-伸苯基伸乙烯)(MEH-PPV)等之聚伸苯基伸乙烯基衍生物、聚(3-烷基噻吩)(PAT)等之聚噻吩衍生物、聚乙烯基咔唑(PVCz)等。
溶劑可列舉甲苯、二甲苯、氯仿等,作為溶解或均勻分散法者,可列舉攪拌、加熱攪拌、超音波分散等之方法。
塗佈方法並無特殊限定,可列舉噴墨法、噴霧法、浸漬法、旋轉塗佈法、轉印印刷法、輥塗佈法、刷毛塗佈法等。再者,塗佈較佳為在氮、氬等之惰性氣體下進行。
燒成方法可列舉在惰性氣體下或真空中,以烘箱或加熱板加熱之方法。
以下列舉合成例、製造例、實施例及比較例,以更具體說明本發明,但本發明不受下述實施例限定。再者,實施例中使用之各測定裝置係如以下所述。
裝置:Varian NMR System 400NB(400MHz)JEOL-ECA700(700MHz)
測定溶劑:DMSO-d6
基準物質:四甲基矽烷(TMS)(δ0.0ppm)
裝置:東曹(股)製 HLC-8200 GPC
管柱:Shodex KF-804L+KF-805L
管柱溫度:40℃
溶劑:四氫呋喃(以下、THF)
檢測器:UV(254nm)
檢量線:標準聚苯乙烯
裝置:J.A Woollam Japan製 多入射角分光橢圓偏光儀VASE
裝置:(股)Rigaku製 TG-8120
昇溫速度:10℃/分鐘
測定溫度:25℃-750℃
裝置:(股)小坂研究所製 ET-4000
裝置:NAPSON corporation製 EC-80
裝置:長州產業(股)製 基板洗淨裝置(減壓電漿方式)
裝置:長州產業(股)製 多機能蒸鍍裝置系統C-E2L1G1-N
裝置:(有)Tech world製 I-V-L測定系統
於氮下,於1000mL四口燒瓶中添加DMAc 456.02g,藉由丙酮-乾冰浴冷卻至-10℃,添加2,4,6-三氯-1,3,5-三嗪[1](84.83g、0.460mol、EVONIK DEGUSSA公司製)使其溶解。之後,滴下溶解於DMAc304.01g之m-苯二胺[2](62.18g、0.575mol)、及苯胺(14.57g、0.156mol)。滴下後攪拌30分鐘,將此反應溶液以送液泵花1小時滴下至於2000mL四口燒瓶中添加DMAc 621.85g並預先於油浴中加熱至85℃之槽中,攪拌1小時
以聚合。
之後,添加苯胺(113.95g、1.224mol),攪拌1小時後,結束反應。藉由冰浴冷卻至室溫後,滴下三乙基胺(116.36g、1.15mol),攪拌30分鐘,將鹽酸予以淬熄。之後,將析出之鹽酸鹽過濾去除。將過濾之反應溶液於28%氨水溶液(279.29g)與離子交換水(8820g)之混合溶液中再沈澱。過濾沈澱物,以減壓乾燥機於150℃乾燥8小時後,再溶解於THF(833.1g),於離子交換水(6665g)中再沈澱。過濾所得之沈澱物,以減壓乾燥機於150℃乾燥25小時,得到目標之高分子化合物[3](以下略稱為HB-TmDA40)118.0g。
HB-TmDA40之1H-NMR光譜的測定結果示於圖1。所得之HB-TmDA40為具有式(1)表示之構造單位的化合物。HB-TmDA40之以GPC、聚苯乙烯換算所測定之重量平均分子量Mw為4,300、多分散度Mw/Mn為3.44。
對於合成例1中所得之HB-TmDA40進行TG-DTA測定後,5%重量減少為419℃。其結果示於圖2。
將合成例1中所得之HB-TmDA40 0.5g溶解於環己酮4.5g,得到淡黃色透明溶液。將所得之聚合物塗漆於玻璃基板上使用旋轉塗佈器以200rpm旋轉塗佈5秒、以
2000rpm旋轉塗佈30秒,於150℃加熱1分鐘、250℃加熱5分鐘去除溶劑,得到被膜。測定所得被膜之折射率後,於550nm之折射率為1.790。
將合成例1中所得之HB-TmDA40 40g溶解於環己酮153.6g、離子交換水6.4g,配製20質量%之溶液(以下稱為HB-TmDA40V)。
添加氧化鈦粒子(金紅石型氧化鈦JA-600A)70.0g、環己酮272.3g、3-甲基丙烯醯氧基丙基三乙氧基矽烷(KBE-503、信越化學工業(股)製)7.0g、離子交換水0.7g,於60℃攪拌3小時。於此分散液296.4g中添加添加製造例1中配製之HB-TmDA40V 84.7g,以超高速萬能均質機(Hiscotron NS-56S、(股)Microtec Nition製、以下同樣)使其分散。將所得之分散液以注射器過濾器過濾(以下將此分散液稱為JA600A-KBE10-D)。
添加製造例1中配製之HB-TmDA40V 874.6g、交聯劑B-882N(三井化學(股)製)50.1g、界面活性劑
Megafac F-554(DIC(股)製)之5質量%環己酮溶液1.75g、環己酮/離子交換水(96/4=wt/wt)473.5g,配製分散液(以下稱為HB-TmDA40-V-F)。
添加製造例1中配製之HB-TmDA40V 526.3g、Light Star LA-OS20PGM(日產化學工業(股)製)359.4g、交聯劑B-882N(三井化學(股)製)30.2g、環己酮/離子交換水(96/4=wt/wt)84.1g,配製分散液(以下稱為HB-TmDA40-L1-70)。
添加製造例1中配製之HB-TmDA40V 294.7g、製造例2中配製之JA600A-KBE10-D 331.6g、交聯劑(B-882N)21.1g、環己酮/離子交換水(96/4=wt/wt)52.6g,配製分散液(以下稱為HB-TmDA40-JA600A-KBE10-70)。
使用製造例3中配製之HB-TmDA40-V-F,於無鹼玻璃基板上藉由旋轉塗佈法,以200rpm 5秒、1000rpm 30秒之條件製膜。之後,於100℃乾燥1分鐘、250℃乾燥1小時,得到硬化膜。測定硬化膜膜厚後,為970nm。
接著於此硬化膜上,使用濺鍍裝置(Sanyu電子
(股)製,SRS-700T/LL),以22℃、輸出350W、7分鐘之條件將ITO予以RF濺鍍,得到ITO基板(以下稱為G-HB-ITO)。ITO之膜厚為250nm。
測定所得ITO基板之表面電阻後,其係113Ω/cm2。
使用製造例4中配製之HB-TmDA40-L1-70,於無鹼玻璃基板上藉由旋轉塗佈法,以200rpm 5秒、1000rpm 30秒之條件製膜。之後,於100℃乾燥1分鐘、250℃乾燥1小時,得到硬化膜。測定硬化膜之膜厚後,其係1.7μm。
於所得之基板上,使用製造例3中配製之HB-TmDA40-V-F,藉由旋轉塗佈法,以200rpm 5秒、1000rpm 30秒之條件製膜。之後,於100℃乾燥1分鐘、250℃乾燥1小時,得到硬化膜。測定硬化膜之膜厚後,其係1.0μm。
接著於此硬化膜上,使用濺鍍裝置(Sanyu電子(股)製,SRS-700T/LL),以22℃、輸出350W、7分鐘之條件將ITO予以RF濺鍍,得到ITO基板(以下稱為G-L-HB-ITO)。ITO之膜厚為250nm。
進一步地,將基板於150℃燒成1小時,測定所得ITO基板之表面電阻後,其係65Ω/cm2。
使用製造例5中配製之HB-TmDA40-JA600A-KBE10-70,於無鹼玻璃基板上藉由旋轉塗佈法,以200rpm 5秒、1000rpm 30秒之條件製膜。之後,於100℃乾燥1分鐘、250℃乾燥1小時,得到硬化膜。測定硬化膜之膜厚後,其係1.0μm。
於所得之基板上,使用製造例3中配製之HB-TmDA40-V-F,藉由旋轉塗佈法,以200rpm 5秒、1000rpm 30秒之條件製膜。之後,於100℃乾燥1分鐘、250℃乾燥1小時,得到硬化膜。測定硬化膜之膜厚後,其係1.0μm。
接著於此硬化膜上,使用濺鍍裝置(Sanyu電子(股)製,SRS-700T/LL),以22℃、輸出350W、7分鐘之條件將ITO予以RF濺鍍,得到ITO基板(以下稱為G-J-HB-ITO)。ITO之膜厚為250nm。
測定所得ITO基板之表面電阻後,其係85Ω/cm2。
於無鹼玻璃基板上,使用濺鍍裝置,以22℃、輸出350W、7分鐘之條件將ITO予以RF濺鍍,得到ITO基板(以下稱為G-ITO)。ITO之膜厚為250nm。
所得之ITO基板的表面電阻為77Ω/cm2。
於投入蒸鍍機前,將製造例7中所得之ITO基板(G-L-HB-ITO),以O2電漿洗淨裝置(150W、30秒)去除表面上之雜質。
接著,對經施以洗淨之ITO基板,使用蒸鍍裝置(真空度1.0×10-5Pa),使下述構造所示之HAT-CN以0.2nm/秒成膜30nm作為電洞注入層。接著,使下述構造所示之α-NPD以0.2nm/秒成膜100nm作為電洞輸送層。進一步,將下述構造所示之CBP與Ir(PPy)3予以共蒸鍍,作為發光層。共蒸鍍係將蒸鍍速率控制為Ir(PPy)3之濃度成為6%,層合40nm。接著,依次層合作為電子輸送層之下述構造所示之BAlq、作為電子注入層之氟化鋰及作為陰極之鋁的薄膜,得到有機EL元件。此時,蒸鍍速率就BAlq及鋁而言係以0.2nm/秒、就氟化鋰而言係以0.02nm/秒之條件分別進行,膜厚分別設為20nm、0.5nm及100nm。
再者,為了防止空氣中之氧、水等之影響所致之特性劣化,係將有機EL元件以密封基板密封後,評估其特性。密封係依以下順序進行。於氧濃度2ppm以下、露點-85℃以下之氮環境中,將有機EL元件容納於密封基板之間,將密封基板以接著材(Nagase chemteX(股)製,XNR5516Z-B1)貼合。此時,將保水劑(Dynic(股)製,HD-071010W-40)與有機EL元件一起容納於密封基板內。對貼合之密封基板照射UV光(波長:365nm、照射量:6,000mJ/cm2)後,於80℃退火處理1小時,使接著材硬化。
除了使用製造例8中所得之ITO基板(G-J-HB-ITO)以取代製造例7中所得之ITO基板(G-L-HB-ITO)以外,係與實施例1同樣地製作有機EL元件。
除了使用製造例6中所得之ITO基板(G-HB-ITO)以取代製造例7中所得之ITO基板(G-L-HB-ITO)以外,係與實施例1同樣地製作有機EL元件。
除了使用製造例9中所得之ITO基板(G-ITO)以取
代製造例7中所得之ITO基板(G-L-HB-ITO)以外,係與實施例1同樣地製作有機EL元件。
對所製作之各元件,測定輝度3000cd/m2時之驅動電壓、電流密度及電流效率。結果示於表1。
如表1所示,以比較例2之元件的電流效率為1.00時,比較例1、實施例1及實施例2之各元件的電流效率,係0.99、1.17、1.60,可知使用了具備特定之光散射膜的ITO電極之本發明之有機EL元件的電流效率優異。
Claims (9)
- 一種有機電致發光元件,其特徵為具備光散射膜,該光散射膜係使含有包含下述式(1)表示之重複單位構造的含有三嗪環之聚合物、交聯劑、與光擴散劑的光散射膜形成用組成物硬化而得到,
- 如請求項1之有機電致發光元件,其中前述光擴散劑之平均粒子徑,為100nm~3μm。
- 如請求項1或2之有機電致發光元件,其中前述光擴散劑,為由有機無機複合光擴散劑、有機光擴散劑及無機光擴散劑中選出之1種或2種以上。
- 如請求項3之有機電致發光元件,其中前述光擴散劑為氧化鈦。
- 如請求項4之有機電致發光元件,其中前述光擴散劑為經表面修飾劑處理之氧化鈦。
- 如請求項3之有機電致發光元件,其中前述光擴散劑為凝集二氧化矽粒子。
- 如請求項6之有機電致發光元件,其中前述光擴散劑為經表面修飾劑處理之凝集二氧化矽粒子。
- 如請求項1~7中任一項之有機電致發光元件,其中前述交聯劑為含有嵌段化異氰酸酯之化合物。
- 如請求項1~8中任一項之有機電致發光元件,其中前述光散射膜係構成光提取層。
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US11460624B2 (en) * | 2017-06-12 | 2022-10-04 | Signify Holding B.V. | Light guide comprising a local light out coupling portion and a method for introducing the same |
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