TW201723029A - 矽氧烷單體及其聚合物、含有該聚合物之組成物、電子元件 - Google Patents
矽氧烷單體及其聚合物、含有該聚合物之組成物、電子元件 Download PDFInfo
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- TW201723029A TW201723029A TW105134669A TW105134669A TW201723029A TW 201723029 A TW201723029 A TW 201723029A TW 105134669 A TW105134669 A TW 105134669A TW 105134669 A TW105134669 A TW 105134669A TW 201723029 A TW201723029 A TW 201723029A
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- 125000000913 palmityl 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])[H] 0.000 description 1
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
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- 238000007789 sealing Methods 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- AAWSDNAGOTWUPV-UHFFFAOYSA-N sulfanyloxyethene Chemical compound SOC=C AAWSDNAGOTWUPV-UHFFFAOYSA-N 0.000 description 1
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- 230000008961 swelling Effects 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- ALYPESYVXOPFNK-UHFFFAOYSA-N thieno[2',3':4,5]thieno[3,2-b]thieno[2',3':4,5]thieno[2,3-d]thiophene Chemical compound C1=CSC2=C1SC1=C2SC2=C1SC1=C2SC=C1 ALYPESYVXOPFNK-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- HEPBQSXQJMTVFI-UHFFFAOYSA-N zinc;butane Chemical compound [Zn+2].CCC[CH2-].CCC[CH2-] HEPBQSXQJMTVFI-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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Abstract
本發明係以提供一種由新穎單體所得之聚合物、含有該聚合物之組成物、電子材料組成物、以及電子元件為目的,其藉由在塗布成膜時所使用的電子材料組成物‧印墨中添加而改善所得的塗膜之平滑性(調平性)的同時,也不會降低電子元件之驅動穩定性。本發明之新穎矽氧烷單體、其聚合物、含有該聚合物之組成物、電子材料組成物,被發現可製作平滑的有機薄膜;含有此等之組成物的電子元件,被發現元件壽命長,可改善驅動穩定性。
Description
本發明係關於一種矽氧烷單體及其聚合物,更關於一種含有該聚合物之組成物、電子材料組成物、及以含有電子材料組成物為特徵的電子元件。
近年來,TFT、太陽能電池、有機電致發光元件等電子元件的研究正向多方領域進展著。以往此等電子元件係藉由真空成膜來製作,但由於近幾年被要求基板的大面積化、產品的低成本化,故以印刷所得的電子元件製造法備受矚目。
此電子元件從材料方面大致上可分類為低分子系材料與高分子系材料。
關於低分子系電子材料,除了以往所使用的真空成膜外,近年亦有研究開發使用噴墨、噴嘴噴射、柔版印刷、轉印法等各種塗布方法將電子材料含有層加以成膜的技術。另一方面,關於高分子系電子材料,因分子量大而不適合真空成膜,故主要係使用與低分子系材料同樣的上述塗布方法。
由塗布成膜所得到的半導體膜,相較於真空
成膜,其平滑性差,且會使電子元件的特性降低,故正研討可形成電子元件之平坦性優異的半導體含有層的有機半導體含有層形成用調平劑及其使用方法、有機半導體含有層形成用組成物‧印墨、以及有機元件(organic device)及其製造方法,例如專利文獻1中提出了一種含有具有特定結構之矽氧烷化合物與(甲基)丙烯酸聚合物或此等兩者的有機半導體含有層形成用調平劑。
[專利文獻1]日本特開2014-205830號公報
然而,根據專利文獻1所記載的發明,就調平效果而言,所得到的塗膜雖具有一定的平坦性,但從高性能的有機發光元件指向的觀點來看,無法充分確保其平坦性。此外,(甲基)丙烯酸聚合物於電子元件中,由於羰基會成為載體捕捉位置,故恐有電子元件之發光效率、壽命等之驅動穩定性降低的情形。結果將致使所得到的電子元件無法得到所期望的性能。
因此,本發明係以提供一種由新穎單體所得之聚合物、含有該聚合物之組成物、電子材料組成物、以及電子元件為目的,其係藉由添加在塗布成膜時所使用的電子材料組成物‧印墨,而改善所得的塗膜之平滑性(調平性)的同時,也不會降低電子元件之驅動穩定性。
本發明者們為了解決上述課題,而進行專心研究的結果發現本發明之由新穎單體所得之聚合物、含有該聚合物之組成物、電子材料組成物可平滑地製作有機薄膜,含有此等之組成物的電子元件可改善驅動穩定性,進而完成本發明。
亦即,本發明關於一種新穎單體、其聚合物、含有該聚合物之組成物、電子材料組成物、及以含有電子材料組成物為特徵的電子元件。
一種以通式(1)所示之單體。
(通式(1)中,n表示1~1000,R1及R2表示亦可具有醚鍵之烴基。又,R3表示乙烯基、或具有乙烯基之有機基。(但,該有機基於結構中不具有羰基。))
又,一種聚合物,其係將至少選自前述通式(1)之單體聚合而成。
又,一種聚合物,其係將至少選自前述通式(1)之單體及通式(1)以外之單體共聚合而成。
又,一種組成物,其特徵在於含有前述聚合物。
又,一種電子材料組成物,其特徵在於含有前述聚合物。
此外,一種電子元件,其特徵在於含有前述組成物及前述電子材料組成物。茲提供如上。
根據本發明,含有由本發明之新穎單體所得到之聚合物的組成物,被發現可製作平滑的有機薄膜;由此等之有機薄膜所得到之電子元件,被發現可改善發光效率、壽命等之驅動穩定性。
以下,針對用以實施本發明之態樣進行詳細說明。
[矽氧烷單體]
本發明之矽氧烷單體係以下述通式(1)所示
(通式(1)中,n表示1~1000,R1及R2表示可具有醚鍵之烴基。又,R3表示乙烯基、或具有乙烯基之有機基。(但,該有機基於結構中不具有羰基。))
作為R1並無特別限制,可列舉:C1~C10烷基、C2~C10烷氧基烷基、C3~C30環烷基、C4~C30環烷氧基烷基、C6~C20之芳基、C6~C20之芳氧基。
作為前述C1~C10烷基並無特別限制,可列舉:甲基、乙基、丙基、異丙基、丁基、異丁基、二級丁基、三級丁基、戊基、己基、癸基等。
作為前述C2~C10烷氧基烷基並無特別限制,可列舉:甲氧基甲基、甲氧基乙基、乙氧基乙基、丙氧基乙基、丙氧基丙基、丁氧基丙基、丁氧基丁基、丁氧基戊基、戊氧基戊基等。
作為前述C3~C30環烷基並無特別限制,可列舉:環丙基、環丁基、環戊基、環己基、環庚基、三環[5,2,1,0(2,6)]癸基、金剛烷基等,較佳為碳原子數3~18之基團。
作為前述C4~C30環烷氧基烷基並無特別限制,可列舉:環丙氧基甲基、環丁氧基乙基、環戊氧基丙基、環己氧基丙基、環庚氧基丙基、三環[5,2,1,0(2,6)]癸氧基丙基、金剛烷氧基丙基等,較佳為碳原子數3~18之基團。
作為前述C6~C20之芳基,可列舉:苯基、萘基、蒽基(anthracenyl)、聯苯基等。
作為前述C6~C20之芳氧基,可列舉:苯氧基、萘氧基、蒽氧基(anthracenyloxy)、聯苯氧基等。
此時,構成前述C1~C10烷基、C1~C10烷氧基烷基、C3~C30環烷基、C3~C30環烷氧基烷基、C6~C20之芳基、C6~C20之芳氧基的氫原子的至少1個,可被前述記載之C1~C10烷基所取代。
此等之中,為了提高調平性,R1較佳為C1~
C10烷基,為了提高與溶劑的相溶性,更佳為甲基、乙基、丙基、異丙基、丁基、異丁基、二級丁基、三級丁基,為了改善電子元件特性,再佳為甲基、乙基、丙基、丁基。
作為R2並無特別限制,可列舉:C1~C10伸烷基、C2~C10伸烷基氧基伸烷基、C3~C30伸環烷基、C4~C30伸環烷基氧基伸烷基、C6~C20之伸芳基、C7~C20之伸芳基氧基伸烷基。
作為前述C1~C10伸烷基並無特別限制,可列舉:亞甲基、伸乙基、伸丙基、伸異丙基、伸丁基、伸異丁基、伸戊基、伸己基、伸癸基等。
作為前述C2~C10伸烷基氧基伸烷基並無特別限制,可列舉:亞甲基氧基亞甲基、伸乙基氧基亞甲基、伸丙基氧基伸乙基、伸丙基氧基伸丙基、伸丙基氧基伸丁基、伸丁基氧基伸丁基、伸丁基氧基伸戊基、伸戊基氧基伸戊基等。
作為前述C3~C30伸環烷基並無特別限制,可列舉:伸環丙基、伸環丁基、伸環戊基、伸環己基、伸環庚基等,較佳為碳原子數3~10之基團。
作為前述C4~C30伸環烷基氧基烷基並無特別限制,可列舉:伸環丙基氧基伸乙基、伸環丁基氧基伸丙基、伸環戊基氧基伸丙基、伸環己基氧基伸丙基、伸環庚基氧基伸丙基等。較佳為碳原子數3~10之基團。
作為前述C6~C20之伸芳基,可列舉:伸苯基、伸萘基、伸蒽基、伸聯苯基等。
作為前述C7~C20之伸芳基氧基伸烷基,可列舉:伸苯基氧基伸丙基、伸萘基氧基伸丙基、伸蒽基氧基伸丙基、伸聯苯基氧基伸丙基等。
此時,構成前述C1~C10伸烷基、C2~C10伸烷基氧基伸烷基、C3~C30伸環烷基、C4~C30伸環烷基氧基伸烷基、C6~C20之伸芳基、C7~C20之伸芳基氧基伸烷基的氫原子的至少1個,可被前述記載之C1~C10烷基所取代。
其中,為了提高調平性,R2較佳為C2~C10伸烷基氧基伸烷基,為了提高溶解性,特佳為亞甲基氧基亞甲基、亞甲基氧基伸乙基、伸乙基氧基伸乙基、伸乙基氧基伸丙基、伸丙基氧基伸丙基、伸丙基氧基伸丁基、伸丁基氧基伸丁基,為了改善電子元件特性,再佳為伸乙基氧基伸乙基、伸乙基氧基伸丙基、伸丙基氧基伸丙基。
R3為乙烯基或具有乙烯基之有機基。
作為具有乙烯基之有機基,可列舉:烯丙基、2-丁烯基、3-丁烯基、3-戊烯基、4-戊烯基、5-己烯基、丁二烯基、2,4-戊二烯基、3,5-己二烯基、4,6-庚二烯基、5,7-辛二烯基等之具有乙烯基之脂肪族烴基類;乙烯基氧基亞甲基、乙烯基氧基伸乙基、乙烯基氧基伸丙基、乙烯基氧基丁烯基等之乙烯基氧基伸烷基類;苯乙烯基;苯乙烯基亞甲基、苯乙烯基伸乙基、苯乙烯基伸丙基、苯乙烯基伸丁基等之具有乙烯基之芳烷基類;苯乙烯基氧基亞甲基、苯乙烯基氧基伸乙基、苯乙烯基氧
基伸丙基、苯乙烯基氧基伸丁基等之苯乙烯基氧基伸烷基類等。
其中,從聚合性優異的觀點來看,較佳為乙烯基、具有乙烯基之脂肪族烴基、苯乙烯基、具有乙烯基之芳烷基,從較容易設計廣範圍分子量的聚合物的觀點來看,特佳為乙烯基、丁二烯基、戊二烯基、苯乙烯基、具有乙烯基之芳烷基,從所得到之聚合物可改善電子元件之驅動穩定性的觀點來看,再佳為乙烯基、丁二烯基2,4-戊二烯基、苯乙烯基、苯乙烯基亞甲基。
通式中,n為1~1000,從由電子材料組成物‧印墨所得到之塗膜的平滑性優異的觀點來看,較佳為3~500,從提高電子元件之驅動穩定性的觀點來看,更佳為5~200。
本發明之矽氧烷單體的具體例顯示如下,但並不限定於此等。
【化3】
(上述化學式中,n為1~1000之整數。)
[矽氧烷單體之製造方法]
作為本發明之矽氧烷單體的製造方法並無特別限制,可列舉使具有羥基之矽氧烷化合物、與具有鹵素基之乙烯基化合物於鹼存在下進行反應之方法。
【化4】
(上述化學式中,n為1~1000之整數。)
作為具有鹵素基之乙烯基化合物可列舉例如:溴乙烯、氯乙烯等之鹵化乙烯基化合物;溴丙烯、氯丙烯、溴乙烯基乙烷(vinyl ethylene bromide)、氯乙烯基乙烷(vinyl ethylene chloride)、溴乙烯基丙烷(vinyl propylene bromide)、氯乙烯基丙烷(vinyl propylene chloride)等之鹵化乙烯基伸烷基化合物;4-溴-1,3-丁二烯、4-氯-1,3-丁二烯等之鹵化丁二烯化合物;5-溴-1,3-戊二烯、5-氯-1,3-戊二烯、6-溴-1,3-己二烯、6-氯-1,3-己二烯、7-溴-1,3-庚二烯、7-氯-1,3-庚二烯等之鹵化烷二烯化合物;4-溴苯乙烯、4-氯苯乙烯等之鹵化苯乙烯基化合物;4-溴甲基苯乙烯、4-氯甲基苯乙烯、4-溴乙基苯乙烯、4-氯乙基苯乙烯等之鹵化伸烷基苯乙烯基化合物等,但不限定於此等。
作為鹼並無特別限制,可列舉氫氧化鈉、氫氧化鉀、氫氧化銫、氫化鈉、三級丁醇鈉、三級丁醇鉀
、甲醇鈉、甲醇鉀等。
上述反應中,材料的進料量並無特別限制,從產率的觀點來看,較佳為相對於具有羥基之矽氧烷化合物,添加1~5當量之具有鹵素基之乙烯基化合物。又,鹼之進料量,從產率的觀點來看,較佳為相對於具有羥基之矽氧烷,添加1~5當量。反應溫度為10~80℃,反應氣體環境較佳為於非活性氣體環境下進行。此外,可添加碘化鉀等之觸媒。
[將矽氧烷單體聚合而成之聚合物]
將本發明之矽氧烷單體聚合而成之聚合物,可為將以通式(1)所示之矽氧烷單體單獨聚合而成之聚合物,亦可為將以通式(I)所示之矽氧烷單體與通式(1)以外之單體共聚而成之聚合物。
通式(1)以外的單體並無特別限制,例如可使用習知慣用的(甲基)丙烯酸酯單體、苯乙烯基單體、乙烯基醚單體、烯丙基單體等。
(甲基)丙烯酸酯單體並無特別限制,可列舉:(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸三級丁酯、(甲基)丙烯酸己酯、(甲基)丙烯酸庚酯、(甲基)丙烯酸辛酯、(甲基)丙烯酸壬酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸十二酯、(甲基)丙烯酸十四酯、(甲基)丙烯酸十六酯、(甲基)丙烯酸十八酯、(甲基)丙烯酸二十二酯等的(甲基)丙烯酸烷基酯類;(甲基)丙烯酸環己酯、(甲基)丙烯酸異酯、(甲基)丙烯酸二環戊酯、(甲基)丙烯酸二環戊氧基
乙酯等的(甲基)丙烯酸環烷基酯類;(甲基)丙烯酸苯甲醯氧乙酯、(甲基)丙烯酸芐酯、(甲基)丙烯酸苯乙酯、(甲基)丙烯酸苯氧乙酯、(甲基)丙烯酸苯氧基二乙二醇酯、(甲基)丙烯酸2-羥基-3-苯氧基丙酯等的(甲基)丙烯酸芳基酯類等。
作為苯乙烯基單體並無特別限制,可列舉:苯乙烯;α-甲基苯乙烯、α-乙基苯乙烯、α-丁基苯乙烯或4-甲基苯乙烯等的經烷基取代之苯乙烯類;氯苯乙烯等的苯乙烯衍生物等。
作為乙烯基醚單體並無特別限制,可列舉:甲基乙烯基醚、乙基乙烯基醚、丙基乙烯基醚、異丙基乙烯基醚、正丁基乙烯基醚、二級丁基乙烯基醚、三級丁基乙烯基醚、異丁基乙烯基醚、正戊基乙烯基醚、異戊基乙烯基醚等的烷基乙烯基醚類;環戊基乙烯基醚、環己基乙烯基醚、環庚基乙烯基醚、環辛基乙烯基醚、2-雙環[2.2.1]庚基乙烯基醚、2-雙環[2.2.2]辛基乙烯基醚、8-三環[5.2.1.0(2,6)]癸基乙烯基醚、1-金剛烷乙烯基醚、2-金剛烷乙烯基醚等的環烷基乙烯基醚類;苯基乙烯基醚、4-甲基苯基乙烯基醚、4-三氟甲基苯基乙烯基醚、4-氟苯基乙烯基醚等的芳基乙烯基醚類;苄基乙烯基醚、4-氟基苄基乙烯基醚等的芳基乙烯基醚類等。
作為烯丙基單體並無特別限制,可列舉:甲基烯丙基醚、乙基烯丙基醚、丙基烯丙基醚、丁基烯丙基醚等的烷基烯丙基醚類;苯基烯丙基醚等的芳基烯丙基醚類;乙酸烯丙酯、烯丙基醇、烯丙基胺。
此等(甲基)丙烯酸酯單體、苯乙烯基單體、乙烯基醚單體、烯丙基單體,特佳為含有疏水性基。在本說明書中,所謂的「疏水性基」係指疏水性基與氫原子鍵結所形成的分子對水的溶解度(25℃、25%RH)為100mg/L以下者。
作為前述疏水性基並無特別限制,可列舉:C1~C18烷基、C3~C20環烷基、C6~C30之芳基。
作為前述C1~C18烷基並無特別限制,可列舉:甲基、乙基、丙基、異丙基、丁基、異丁基、二級丁基、三級丁基、戊基、己基、癸基、十一烷基、十二烷基、十八烷基、2-乙基己基等。
作為前述C3~C20環烷基並無特別限制,可列舉:環丙基、環丁基、環戊基、環己基、環庚基、三環[5,2,1,0(2,6)]癸基、金剛烷基等。
作為前述C6~C30之芳基,可列舉:苯基、萘基、蒽基、聯苯基等。
作為這種具有疏水性基的單體,可列舉前述記載的:(甲基)丙烯酸烷基酯類、(甲基)丙烯酸環烷基酯類、(甲基)丙烯酸芳基酯類、苯乙烯、經烷基取代之苯乙烯類、烷基乙烯基醚類、環烷基乙烯基醚類、芳基乙烯基醚類、烷基烯丙基醚類、芳基烯丙基醚類。
前述具有疏水性基的單體之中,基於與通式(1)所表示之單體的共聚性良好,並可得到廣範圍分子量的聚合物,較佳為前述記載的(甲基)丙烯酸烷基酯類、(甲基)丙烯酸環烷基酯類、(甲基)丙烯酸芳基酯類、苯乙
烯、經烷基取代之苯乙烯類、烷基乙烯基醚類、環烷基乙烯基醚類、芳基乙烯基醚類。再者,從更適合得到提高所得到之聚合物之調平性效果的觀點來看,較佳為使用(甲基)丙烯酸芳基酯類、苯乙烯、經烷基取代之苯乙烯類、芳基乙烯基醚類等含有芳基的含芳香族單體,從電子元件之驅動穩定性的觀點來看,再佳為苯乙烯、經烷基取代之苯乙烯類、芳基乙烯基醚類,於使用苯乙烯、經烷基取代之苯乙烯類、苯基乙烯基醚、苄基乙烯基醚的情況下,本發明之效果尤為顯著。
此外,上述單體可單獨使用,亦可組合2種以上使用。
本發明之聚合物的重量平均分子量(Mw)較佳為500~100,000,從平滑性的觀點來看,更佳為3,000~40,000。此外,在本說明書中,「重量平均分子量(Mw)」的值,採用依實施例之測定方法所測定的值。
又,本發明之聚合物的數量平均分子量(Mn)較佳為500~100,000,從平滑性的觀點來看,更佳為3,000~40,000。此外,在本說明書中,「數量平均分子量(Mn)」的值,採用依實施例之測定方法所測定的值。
[聚合物之製造方法]
為了得到本發明之聚合物,只要使用上述單體與聚合起始劑,以習知慣用的方法使其聚合(共聚合)即可,可為隨機共聚物、嵌段共聚物、接枝共聚物等之任一種。
作為聚合方法,可列舉:自由基聚合、陰離
子聚合、陽離子聚合等。
作為自由基聚合,反應條件並無特別限定,例如可使用單體與自由基聚合起始劑,在溶劑中進行聚合。
作為自由基聚合起始劑可使用一般已知者,可列舉例如:2,2’-偶氮二異丁腈、2,2’-偶氮雙-(2,4-二甲基戊腈)、2,2’-偶氮雙-(4-甲氧基-2,4-二甲基戊腈)等的偶氮化合物;過氧化苯甲醯、過氧化月桂醯、三級丁基過氧化三甲基乙酸酯、三級丁基過氧基乙基己酸酯、1,1’-雙-(過氧化三級丁基)環己烷、過氧化三級戊基-2-乙基己酸酯、過氧化三級己基-2-乙基己酸酯等的有機過氧化物及過氧化氫等。該等可單獨使用1種,亦可併用兩種以上。
又,自由基聚合起始劑的使用量並無特別限制,相對於100質量份的單體,一般為0.001~1質量份。為了在前述較佳重量平均分子量的範圍內得到本發明之聚合物,相對於100質量份的單體,自由基聚合起始劑的使用量較佳為0.005~0.5質量份,再佳為0.01~0.3質量份。
若列舉可用於自由基聚合之溶劑的代表者,可列舉例如:丙酮、甲基乙基酮、甲基正丙基酮、甲基異丙基酮、甲基正丁基酮、甲基異丁基酮、甲基正戊基酮、甲基正己基酮、二乙基酮、乙基正丁基酮、二正丙基酮、二異丁酮、環己酮、佛耳酮等的酮系溶劑;
乙醚、異丙醚、正丁醚、二異戊醚、乙二醇二甲醚、乙二醇二乙醚、二乙二醇二甲醚、二乙二醇、
二烷、四氫呋喃等的醚系溶劑;甲酸乙酯、甲酸丙酯、甲酸-正丁酯、乙酸乙酯、乙酸-正丙酯、乙酸異丙酯、乙酸-正丁酯、乙酸-正戊酯、乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、二乙二醇單甲醚乙酸酯、二乙二醇單乙醚乙酸酯、丙二醇單甲醚乙酸酯、乙基-3-乙氧基丙酸酯等的酯系溶劑;甲醇、乙醇、異丙醇、正丁醇、異丁醇、二丙酮醇、3-甲氧基-1-丙醇、3-甲氧基-1-丁醇、3-甲基-3-甲氧基丁醇等的醇系溶劑;甲苯、二甲苯、Solvesso 100、Solvesso 150、Swasol 1800、Swasol 310、Isopar E、Isopar G、Exxon naphtha 5號、Exxon naphtha 6號等的烴系溶劑。
此等溶劑可單獨使用,亦可併用2種以上。
自由基聚合反應中溶劑的使用量並無特別限制,相對於100質量份的單體進料量,從攪拌性的觀點來看,較佳為0~3000質量份,從反應性的觀點來看,更佳為10~1000質量份,從分子量控制的觀點來看,再佳為10~500質量份。
作為陰離子聚合,反應條件並無特別限定,例如可使用單體與陰離子聚合起始劑,在溶劑中進行聚合。
作為陰離子聚合起始劑可使用一般已知者,可列舉例如:甲基鋰、正丁基鋰、二級丁基鋰、三級丁基鋰、異丙基鋰、正丙基鋰、異丙基鋰苯基鋰、苄基鋰、己基鋰、丁基鈉、丁基鉀等的有機鹼金屬;氯化甲鎂
、溴化甲鎂、碘化甲鎂、溴化乙鎂、溴化丙鎂、氯化苯鎂、溴化苯鎂、二丁基鎂等的有機鹼土金屬;鋰、鈉、鉀等的鹼金屬;二乙基鋅、二丁基鋅、乙基丁基鋅等的有機鋅;三甲基鋁、三乙基鋁、甲基雙苯氧基鋁、異丙基雙苯氧基鋁、雙(2,6-二-三級丁基苯氧基)甲基鋁、雙(2,6-二-三級丁基-4-甲基苯氧基)甲基鋁等的有機鋁等。該等可單獨使用1種,亦可併用兩種以上。
又,陰離子聚合起始劑的使用量並無特別限制,相對於100質量份的單體,較佳為0.001~1質量份,更佳為0.005~0.5質量份,再佳為0.01~0.3質量份。
作為可用於陰離子聚合的溶劑,可列舉如上述者。
陰離子聚合反應中溶劑的使用量並無特別限制,相對於100質量份的單體進料量,從攪拌性的觀點來看,較佳為0~3000質量份,從反應性的觀點來看,更佳為10~1000質量份,從分子量控制的觀點來看,再佳為10~500質量份。
作為陽離子聚合,反應條件並無特別限定,例如可使用單體與陽離子聚合起始劑,在溶劑中進行聚合。
作為陽離子聚合起始劑,可用一般已知者,可列舉例如:鹽酸、硫酸、過氯酸、三氟乙酸、甲磺酸、三氟甲磺酸、氯磺酸、氟磺酸等的質子酸;三氟化硼、氯化鋁、四氯化鈦、四氯化錫、三氯化鐵等的路易士酸等。該等可單獨使用1種,亦可併用兩種以上。
又,陽離子聚合起始劑的使用量並無特別限制,相對於100質量份的單體,一般為0.001~1質量份。為了在前述較佳重量平均分子量的範圍內得到本發明之聚合物,相對於100質量份的單體,陽離子聚合起始劑的使用量較佳為0.005~0.5質量份,再佳為0.01~0.3質量份。
作為可用於陽離子聚合的溶劑,可列舉上述可用於自由基聚合的溶劑。
陽離子聚合反應中溶劑的使用量並無特別限制,相對於100質量份的單體進料量,從攪拌性的觀點來看,較佳為0~3000質量份,從反應性的觀點來看,更佳為10~51000質量份,從分子量控制的觀點來看,再佳為10~500質量份。
此外,上述自由基聚合、陰離子聚合、陽離子聚合可為活性聚合(living polymerization),可使用例如「季刊 化學總論No.18,1993精密聚合 日本化學會編(學會出版中心)」所記載的方法。
[組成物]
含有本發明之聚合物的組成物,從具有提高成膜後之調平性的功能的觀點來看,可列舉:以熱或光所形成的硬化組成物、印墨組成物、塗布組成物、電子材料組成物等,但並不限定於此等。其中,本發明之聚合物不會降低電子元件的電特性,故可用於對電子材料組成物。
[電子材料組成物]
含有本發明之聚合物的電子材料組成物,包含有機
半導體材料、本發明之聚合物(調平劑)及溶劑。此外,前述電子材料組成物中亦可因應其他需要而含有界面活性劑等。
相對於電子材料組成物總量而言,有機半導體材料的含量較佳為0.01~10質量%,從電特性的觀點來看,更佳為0.01~5質量%。
相對於電子材料組成物總量而言,本發明之聚合物的含量較佳為0.001~5.0質量%,從調平性的觀點來看,更佳為0.001~1.0質量%。
相對於電子材料組成物總量而言,溶劑的含量較佳為90~99質量%,從成膜性的觀點來看,更佳為95~99質量%。
(有機半導體材料)
作為有機半導體材料,可列舉:有機TFT材料、有機太陽能電池材料、有機EL材料等,但並不限定於此等。
作為有機TFT材料,只要是可使用於構成有機TFT元件之層的材料即可,並無特別限制,可列舉例如:萘、蔥、稠四苯、稠五苯、稠六苯、稠七苯等可附有取代基的稠苯類,例如:1,4-雙苯乙烯基苯、1,4-雙(2-甲基苯乙烯基)苯、1,4-雙(3-甲基苯乙烯基)苯(4MSB)、1,4-雙(4-甲基苯乙烯基)苯、聚伸苯伸乙烯等具有C6H5-CH=CH-C6H5所表示之苯乙烯基結構的化合物、這種化合物的寡聚物或聚合物;α-4T、α-5T、α-6T、α-7T、α-8T的衍生物等之可具有取代基的噻吩寡聚物;聚己基噻吩、聚(9,9-二辛基茀基-2,7-二基-共聚-聯噻吩)等的
噻吩系高分子;雙苯并噻吩衍生物、α,α’-雙(二噻吩并[3,2-b:2’,3’-d]噻吩)、二噻吩并噻吩-噻吩之共寡聚物(co-oligomer)、稠五噻吩(pentathienoacene)等稠合寡聚噻吩特別是具有噻吩并苯骨架或二噻吩并苯骨架的化合物、[1]苯并噻吩并[3,2-b][1]苯并噻吩衍生物;又,硒吩寡聚物、無金屬酞青素、銅酞青素、鉛酞青素、氧鈦酞青素;鉑卟啉、卟啉、苯并卟啉等的卟啉類;四硫富烯(TTF)及其衍生物、紅螢烯及其衍生物等;四氰醌二甲烷(TCNQ)、11,11,12,12-四氰基萘-2,6-醌二甲烷(TCNNQ)等的醌寡聚物;C60、C70、PCBM等的富勒烯類;N,N’-二苯基-3,4,9,10-苝四甲酸二醯亞胺、N,N’-二辛基-3,4,9,10-苝四甲酸二醯亞胺(C8-PTCDI)、NTCDA、1,4,5,8-萘四甲酸二醯亞胺(NTCDI)等的四羧酸類等。
作為有機太陽能電池材料,只要是可用於構成有機太陽能電池元件之層的材料即可,並無特別限制,可列舉例如:C60及C70之富勒烯、富勒烯衍生物、奈米碳管、苝衍生物、多環醌、喹吖酮等,高分子系可列舉CN-聚(伸苯基-伸乙烯基)、MEH-CN-PPV、含有-CN基或CF3基之聚合物、該等之經-CF3取代聚合物、聚(茀)衍生物等。
作為有機EL材料,只要係可用於構成有機EL元件之層的材料即可,並無特別限制。在一實施態樣中,作為電子材料組成物可含有的有機EL材料,可列舉:可使用於發光層的發光材料、可使用於電洞注入層的電洞注入材料、可使用於電洞輸送層的電洞輸送材料、可
使用於電子輸送層的電子輸送材料。
(發光材料)
發光材料包含主體材料及摻雜材料。
主體材料與摻雜材料的組成比並不限定於此,但相對於100質量份的主體而言,摻雜物較佳為1~50質量份,從發光效率的觀點來看,再佳為5~20質量份。
前述主體材料可分類為高分子主體材料及低分子主體材料。此外,在本說明書中,所謂的「低分子」係指重量平均分子量(Mw)為5,000以下者。另一方面,在本說明書中,所謂的「高分子」係指重量平均分子量(Mw)超過5,000者。此時,在本說明書中,「重量平均分子量(Mw)」係採用使用以聚苯乙烯為標準物質的凝膠滲透層析法(GPC)所測定的值。
作為高分子主體材料並無特別限制,可列舉:聚(9-乙烯基咔唑)(PVK)、聚茀(PF)、聚伸苯基伸乙烯(PPV)、及包含此等單體單元的共聚物等。
高分子主體材料的重量平均分子量(Mw)較佳為超過5,000且5,000,000以下,從成膜性的觀點來看,更佳為超過5,000且1,000,000以下。
作為低分子主體材料並無特別限制,可列舉:4,4’-雙(9H-咔唑-9-基)聯苯(CBP)、4,4’-雙(9-咔唑基)-2,2’-二甲基聯苯(CDBP)、N,N’-二咔唑基-1,4-二甲基苯(DCB)、1,3-二咔唑基苯(mCP)、3,5-雙(9-咔唑基)四苯基矽烷(SimCP)、9,9’-(對三級丁基苯基)-1,3-雙咔唑等的咔唑衍生物、4,4‘-二(二(三苯矽基)-聯苯(BSB)、9-(4-三級
丁基苯基)-3,6-雙(三苯矽基)-9H-咔唑(CzSi)、1,3-雙(三苯矽基)苯(UGH3)等的矽烷衍生物、雙(2-甲基-8-羥基喹啉基)-4-(苯基酚)鋁(Bis(2-methyl-8-quinolinolato)-4-(phenylphenolato)aluminium)(BAlq)等的金屬錯合物、2,7-雙(二苯基氧化膦)-9,9-二甲基螢光素(P06)等的氧化膦衍生物、1,3,5-參[4-(二苯基胺基)苯基]苯(TDAPB)等的胺衍生物、二唑衍生物、咪唑衍生物、三衍生物、吡啶衍生物、嘧啶衍生物等的雜環化合物等。
低分子主體材料的重量平均分子量(Mw)較佳為100~5,000,從成膜性的觀點來看,更佳為300~5,000。
上述主體材料之中,作為主體材料較佳為使用低分子主體材料,更佳為使用4,4’-雙(9H-咔唑-9-基)聯苯(CBP)、9,9’-(對三級丁基苯)-1,3-雙咔唑等的咔唑衍生物、雙(2-甲基-8-羥基喹啉基)-4-(苯基酚)鋁(BAlq)、二唑衍生物、咪唑衍生物、三衍生物、吡啶衍生物、嘧啶衍生物等的雜環化合物,再佳為使用4,4’-雙(9H-咔唑-9-基)聯苯(CBP)、9,9’-(對三級丁基苯)-1,3-雙咔唑、咪唑衍生物、三衍生物、吡啶衍生物、嘧啶衍生物等的雜環化合物。
上述主體材料可單獨使用,亦可組合2種以上使用。
前述摻雜材料,一般可分類為高分子摻雜材料及低分子摻雜材料。
作為高分子摻雜材料並無特別限制,可列舉
:聚伸苯基伸乙烯(PPV)、氰基聚伸苯基伸乙烯(CN-PPV)、聚(伸茀基伸乙炔)(PFE)、聚茀(PFO)、聚噻吩聚合物、聚吡啶、及包含該等單體單元的共聚物等。
高分子摻雜材料的重量平均分子量(Mw)較佳為超過5,000且5,000,000以下,從發光效率的觀點來看,更佳為超過5,000且1,000,000以下。
作為低分子摻雜材料並無特別限制,可列舉螢光發光材料、磷光發光材料等。
作為前述螢光發光材料,可列舉:萘、苝、芘、、蔥、香豆素、對雙(2-苯基乙烯基)苯、喹吖酮、Al(C9H6NO)3等的鋁錯合物等、紅螢烯、萘嘧啶酮(perimidone)、二氰基亞甲基-2-甲基-6-(對二甲胺基苯乙烯基)-4H-哌喃(DCM)、苯并哌喃、玫瑰紅、苯并硫(benzothioxanthene)、氮雜苯并硫、及此等之衍生物等。
作為前述磷光發光材料,可列舉含有周期表第7族~第11族之中心金屬與配位於前述中心金屬之芳香族系配位子的錯合物。
作為前述周期表第7族~第11族之中心金屬,可列舉:釕、銠、鈀、鋨、銥、金、鉑、銀、銅等。此等之中,從發光效率的觀點來看,中心金屬較佳為銥。
作為前述配位子,可列舉:苯基吡啶、對甲苯基吡啶、噻吩基吡啶、二氟苯基吡啶、苯基異喹啉、茀吡啶(fluorenopyridine)、茀喹啉(fluorenoquinoline)、乙醯丙酮、及此等之衍生物。此等之中,配位子較佳為
苯基吡啶、對甲苯基吡啶、及此等之衍生物,從成膜性的觀點來看,更佳為對甲苯基吡啶及其衍生物。
作為具體的磷光發光材料,可列舉:參(2-苯基吡啶)銥(Ir(ppy)3)、參(2-苯基吡啶)釕、參(2-苯基吡啶)鈀、雙(2-苯基吡啶)鉑、參(2-苯基吡啶)鋨、參(2-苯基吡啶)錸、參[2-(對甲苯基)吡啶]銥(Ir(mppy)3)、參[2-(對甲苯基)吡啶]釕、參[2-(對甲苯基)吡啶]鈀、參[2-(對甲苯基)吡啶]鉑、參[2-(對甲苯基)吡啶]鋨、參[2-(對甲苯基)吡啶]錸、辛乙基鉑卟啉、辛苯基鉑卟啉、辛乙基鈀卟啉、辛苯基鈀卟啉等。
上述之中,摻雜材料較佳為低分子摻雜材料,從發光效率的觀點來看,較佳為磷光發光材料。
低分子摻雜材料的重量平均分子量(Mw)較佳為100~5,000,更佳為100~3,000。
上述摻雜材料可單獨使用,亦可組合2種以上使用。
上述之中,作為發光材料,從可得到更高發光效率的觀點來看,較佳為使用低分子發光材料,更佳為使用低分子主體材料及低分子摻雜材料。
(電洞注入材料)
作為電洞注入材料並無特別限制,可列舉:銅酞青素等的酞青素化合物;4,4’,4”-參[苯基(m-甲苯基)胺基]三苯胺等的三苯胺衍生物;1,4,5,8,9,12-六氮雜聯伸三苯六腈、2,3,5,6-四氟基-7,7,8,8-四氰基-醌二甲烷等的氰基化合物;氧化釩、氧化鉬等的氧化物;非晶碳;聚苯胺(
苯胺綠)、聚(3,4-伸乙基二氧噻吩)-聚(苯乙烯磺酸)(PEDOT-PSS)、聚吡咯等的高分子。此等之中,從成膜性的觀點來看,電洞注入材料較佳為高分子。
上述電洞注入材料可單獨使用,亦可組合2種以上使用。
(電洞輸送材料)
作為電洞輸送材料並無特別限制,可列舉:TPD(N,N'-二苯基-N,N’-二(3-甲基苯基)-1,1’-聯苯-4,4’二胺)、α-NPD(4,4’-雙[N-(1-萘基)-N-苯基胺基]聯苯)、m-MTDATA(4、4’,4”-參(3-甲基苯基苯基胺基)三苯胺)等的低分子三苯胺衍生物;聚乙烯基咔唑;下述化學式HT-2所表示之將取代基導入三苯胺衍生物並進行聚合而成的高分子化合物等。該等之中,從電洞輸送性的觀點來看,電洞輸送材料較佳為三苯胺衍生物、將取代基導入三苯胺衍生物並進行聚合而成的如化5所表示之HT-2般的高分子化合物。
上述電洞輸送材料可單獨使用,亦可組合2種以上使用。
(電子輸送材料)
作為電子輸送材料並無特別限制,可列舉:參(8-羥基喹啉)鋁(Alq)、參(4-甲基-8-羥基喹啉)鋁(Almq3)、雙(10-羥基苯并[h]喹啉)鈹(BeBq2)、雙(2-甲基-8-羥基喹啉)(對苯基酚)鋁(BAlq)、雙(8-羥基喹啉)鋅(Znq)等具有喹啉骨架或苯并喹啉骨架的金屬錯合物;雙[2-(2’-羥苯基)苯并唑(benzooxazolato)]鋅(Zn(BOX)2)等具有苯并唑啉骨架的金屬錯合物;雙[2-(2’-羥苯基)苯并噻唑(benzothiazolato)]鋅(Zn(BTZ)2)般具有苯并噻唑啉骨架的金屬錯合物;2-(4-聯苯基)-5-(4-三級丁基苯)-1,3,4-二唑(PBD)、3-(4-聯苯基)-4-苯基-5-(4-三級丁基苯基)-1,2,4-三唑(TAZ)、1,3-雙[5-(對三級丁基苯基)-1,3,4-二唑-2-基]苯(OXD-7)、9-[4-(5-苯基-1,3,4-二唑-2-基)苯基]咔唑(CO11)、2,2’,2”-(1,3,5-次苄基)參(1-苯基-1H-苯并咪唑)(TPBI)、2-[3-(二苯并噻吩-4-基)苯基]-1-苯基-1H-苯并咪唑(mDBTBIm-II)等的聚唑衍生物;如化6所表示之ET-1的苯并咪唑衍生物;喹啉衍生物;苝衍生物;吡啶衍生物;嘧啶衍生物;三衍生物;喹啉衍生物;二苯基醌衍生物;經硝取代之茀衍生物等。此等之中,從電子輸送性的觀點來看,電子輸送材料較佳為苯并咪唑衍生物、吡啶衍生物、嘧啶衍生物、三衍生物。
【化6】
上述電子輸送材料可單獨使用,亦可組合2種以上使用。
(溶劑)
作為溶劑並無特別限制,可適當使用習知者。具體而言,可列舉:芳香族系溶劑、烷烴系溶劑、醚系溶劑、醇系溶劑、酯系溶劑、醯胺系溶劑、其他溶劑等。
作為前述芳香族系溶劑,可列舉:甲苯、二甲苯、乙苯、異丙苯、戊苯、己苯、環己苯、十二烷基苯、1,3,5-三甲苯、二苯甲烷、二甲氧基苯、苯乙醚、甲氧基甲苯、苯甲醚、甲基苯甲醚、二甲基苯甲醚等的單環式芳香族溶劑;環己苯、四氫化萘、萘、甲基萘等的稠合環芳香族溶劑;甲基苯基醚、乙基苯基醚、丙基苯基醚、丁基苯基醚等的醚系芳香族溶劑;乙酸苯酯、丙酸苯酯、苯甲酸乙酯、苯甲酸丙酯、苯甲酸丁酯等的酯系芳香族溶劑等。
作為前述烷烴系溶劑,可列舉:戊烷、己烷、辛烷、環己烷等。
作為前述醚系溶劑,可列舉:二烷、乙二醇二甲醚、乙二醇二乙醚、丙二醇-1-單甲醚乙酸酯、四氫呋喃等。
作為前述醇系溶劑,可列舉:甲醇、乙醇、異丙醇等。
作為前述酯系溶劑,可列舉:乙酸乙酯、乙酸丁酯、乳酸乙酯、乳酸丁酯等。
作為前述醯胺系溶劑,可列舉:N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等。
作為前述其他溶劑,可列舉:水、二甲亞碸、丙酮、氯仿、二氯甲烷等。
此等之中,作為溶劑,從有機半導體材料之溶解性的觀點來看,較佳為芳香族系溶劑,從調平性的觀點來看,更佳為含有選自包含稠合環芳香族溶劑、醚系芳香族溶劑及酯系芳香族溶劑之群組中的至少1種,從成膜性的觀點來看,再佳為使用稠合環芳香族溶劑及/或醚系芳香族溶劑。
此外,上述溶劑可單獨使用,亦可組合2種以上使用。
若塗布本態樣之電子材料組成物而形成塗膜,則因做為調平劑的本發明之聚合物具有矽氧烷結構,故在塗膜表面上配向,而使表面張力降低。而,藉由使此狀態下所得到之塗膜進行乾燥,可防止因乾燥而發生膨脹,可得到高度實現平坦性的層,進而可得到具有高性能的有機功能層。
又,在一實施態樣中,將電子材料組成物使用於形成有機EL元件之發光層的情況下,亦可呈現提高有機EL元件之驅動穩定性的功能。這樣的功能係被認為是由於在本發明之聚合物所具有的矽氧烷結構中,沒有作為載體捕捉位置的羰基之故。
若更詳細地進行說明,在一實施態樣中,發光材料包含主體材料及摻雜材料。而,在發光層中,以主體材料輸送電洞及/或電子,藉由利用因摻雜材料所輸送之電洞及電子的再結合所產生的能量,使得發光層發光。因此,只要在發光層中有效率地進行電洞與電子的輸送,即可有效率地發光,進而提高驅動穩定性。
電子材料組成物所含有之以往的調平劑,雖可於塗布印墨組成物所得到之塗膜的表面配向而使表面張力降低,以製作平滑的塗膜,但調平劑所具有的矽氧烷結構中,由於具有成為載體捕捉位置之電荷極化官能基,故而電荷的輸送受到抑制,元件之驅動變得不穩定。亦即,若使用以往的調平劑,雖然可以得到一定程度的起伏(undulation)之防止效果,但其代價則是降低驅動穩定性。
相對於此,若於調平劑之矽氧烷結構中不含電荷極化官能基,則可抑制電荷輸送之妨礙。其結果可於發光層中更有效率地輸送電荷,提升元件的驅動穩定性。
[電子元件]
接著,就本發明之電子元件進行說明。其係以任一
種態樣含有「具有本發明之聚合物的組成物或電子材料組成物」的電子元件。作為電子元件的具體例,可列舉:太陽能電池或光吸收元件等的光電轉換元件、電場效果型電晶體或靜電感應型電晶體或雙極性電晶體等的電晶體、有機電致發光元件(以下簡稱為有機EL元件)、溫度感測器、氣體感測器、濕度感測器、輻射線感測器等,但並不限定於此等。
作為其中一例,以下就有機EL元件進行說明。
<有機EL元件>
根據本發明之一態樣,其提供一種包含陽極、發光層、及陰極的有機EL元件。此時,其特徵為:前述發光層係由電子材料組成物所形成。
此外,前述有機EL元件,可含有1層以上的電洞注入層、電洞輸送層、電子輸送層及電子注入層等的其他層。又,亦可含有密封構件等習知者。
又,根據另一實施態樣,其提供一種包含陽極、發光層、陰極、及選自包含電洞注入層、電洞輸送層、電子輸送層及電子注入層之群組中的至少1層的有機EL元件。此時,選自包含發光層、電洞注入層、電洞輸送層、及電子輸送層之群組中的至少1層,其特徵為包含本發明之聚合物(調平劑)。
亦即,有機EL元件具有下述情況:以陽極、發光層及陰極作為最小構成單元,更包含以選自包含電洞注入層、電洞輸送層、電子輸送層及電子注入層之群組中的至少1層為任意構成單元。此情形下,調平劑可僅
包含於發光層,亦可僅包含於選自包含電洞注入層、電洞輸送層及電子輸送性之群組中的至少1層(例如僅電洞輸送層、或者電洞輸送層及電子輸送層),亦可包含於發光層、以及電洞注入層、電洞輸送層及電子輸送層之至少1層。其中,較佳為發光層及/或電洞輸送層包含調平劑,更佳為發光層包含調平劑。
以下就有機EL元件的各構成進行詳細說明。
[陽極]
作為陽極並無特別限制,可使用金(Au)等的金屬、碘化銅(CuI)、氧化銦錫(ITO)、氧化錫(SnO2)、氧化鋅(ZnO)等。該等材料可單獨使用,亦可組合2種以上使用。
就陽極的膜厚而言,並無特別限制,較佳為10~1000nm,更佳為10~200nm。
可藉由蒸鍍或濺鍍等方法形成陽極。此時,亦可藉由光刻法或使用遮罩的方法進行圖案形成。
[電洞注入層]
電洞注入層係有機發光元件中的任意構成要件,其具有從陽極導入電洞的功能。一般從陽極導入的電洞被輸送至電洞輸送層或發光層。
可用於電洞注入層的材料,可使用與上述相同者,故此處省略說明。
就電洞注入層的膜厚而言,並無特別限制,較佳為0.1nm~5μm。
電洞注入層可為單層,亦可為積層2層以上者。
可藉由濕式成膜法及乾式成膜法形成電洞注
入層。
以濕式成膜法形成電洞注入層的情況下,一般包含塗布上述有機發光元件用印墨組成物,並將所得到之塗膜乾燥的步驟。此時,作為塗布的方式並無特別限制,可列舉:噴墨印刷法、凸版印刷法、照相凹版印刷法、網版印刷法、噴嘴印刷法等。
又,以乾式成膜法形成電洞注入層的情況下,可應用真空蒸鍍法、旋轉塗布法等。
[電洞輸送層]
電洞輸送層係有機發光元件中的任意構成要件,其具有有效地輸送電洞的功能。又,電洞輸送層可具有防止電洞輸送的功能。電洞輸送層,一般係從陽極或電洞注入層導入電洞,並將電洞輸送至發光層。
可用於電洞輸送層的材料,可使用與上述相同者,故此處省略說明。
就電洞輸送層的膜厚而言,並無特別限制,較佳為1nm~5μm,更佳為5nm~1μm,再佳為10~500nm。
電洞輸送層可為單層,亦可為積層2層以上者。
可藉由濕式成膜法及乾式成膜法形成電洞輸送層。
以濕式成膜法形成電洞輸送層的情況下,一般包含塗布上述有機發光元件用印墨組成物,並將所得到之塗膜乾燥的步驟。此時,作為塗布的方式並無特別限制,可列舉:噴墨印刷法、凸版印刷法、照相凹版印刷法、網版印刷法、噴嘴印刷法等。
又,以乾式成膜法形成電洞輸送層的情況下,可應用真空蒸鍍法、旋轉塗布法等。
[發光層]
發光層具有利用因注入發光層之電洞及電子的再結合所產生的能量而使其發光的功能。
可用於發光層的材料可使用與上述相同者,故此處省略說明。
就發光層的膜厚而言,並無特別限制,較佳為2~100nm,更佳為2~20nm。
可藉由濕式成膜法及乾式成膜法形成發光層。
以濕式成膜法形成發光層的情況下,一般包含塗布上述有機發光元件用印墨組成物,並將所得到之塗膜乾燥的步驟。此時,作為塗布的方式並無特別限制,可列舉:噴墨印刷法、凸版印刷法、照相凹版印刷法、網版印刷法、噴嘴印刷法等。
又,以乾式成膜法形成發光層的情況下,可應用真空蒸鍍法、旋轉塗布法等。
[電子輸送層]
電子輸送層係有機發光元件中的任意構成要件,其具有有效地輸送電子的功能。又,電子輸送層可具有防止電子輸送的功能。電子輸送層一般係從陰極或電子注入層導入電子,並將電子輸送至發光層。
可用於電子輸送層的材料可使用與上述相同者,故此處省略說明。
就電子輸送層的膜厚而言,並無特別限制,
較佳為5nm~5μm,更佳為5~200nm。
電子輸送層可為單層,亦可為積層2層以上者。
可藉由濕式成膜法及乾式成膜法形成電子輸送層。
以濕式成膜法形成電子輸送層的情況下,一般包含塗布上述有機發光元件用印墨組成物,並將所得到之塗膜乾燥的步驟。此時,作為塗布的方式並無特別限制,可列舉:噴墨印刷法、凸版印刷法、照相凹版印刷法、網版印刷法、噴嘴印刷法等。
又,以乾式成膜法形成電子輸送層的情況下,可應用真空蒸鍍法、旋轉塗布法等。
[電子注入層]
電子注入層係有機發光元件中的任意構成要件,其具有從陰極導入電子的功能。一般從陰極導入的電子被輸送至電子輸送層或發光層。
電子注入材料並無特別限制,可列舉:鋰、鈣等的鹼金屬;鍶、鋁等的金屬;氟化鋰、氟化鈉等的鹼金屬鹽;8-羥基喹啉鋰等的鹼金屬化合物;氟化鎂等的鹼土金屬鹽;氧化鋁等的氧化物等。該等之中,電子注入材料較佳為鹼金屬、鹼金屬鹽、鹼金屬化合物,更佳為鹼金屬鹽、鹼金屬化合物。
上述電子注入材料可單獨使用,亦可組合2種以上使用。
就電子注入層的膜厚而言,並無特別限制,較佳為0.1nm~5μm。
電子注入層可為單層,亦可為積層2層以上者。
可藉由濕式成膜法及乾式成膜法形成電子注入層。
以濕式成膜法形成電子注入層的情況下,一般包含塗布上述有機發光元件用印墨組成物,並將所得到之塗膜乾燥的步驟。此時,作為塗布的方式並無特別限制,可列舉:噴墨印刷法、凸版印刷法、照相凹版印刷法、網版印刷法、噴嘴印刷法等。
又,以乾式成膜法形成電子注入層情況下,可應用真空蒸鍍法、旋轉塗布法等。
[陰極]
作為陰極並無特別限制,可列舉:鋰、鈉、鎂、鋁、鈉-鉀合金、鎂/鋁混合物、鎂/銦混合物、鋁/氧化鋁(Al2O3)混合物、稀土類金屬等。此等材料可單獨使用,亦可組合2種以上使用。
一般可藉由蒸鍍或濺鍍等方法形成陰極。
就陰極的膜厚而言,並無特別限制,較佳為10~1000nm,更佳為10~200nm。
在一實施態樣中,包含使用上述電子材料組成物所形成之層體的有機EL元件,可適當地防止形成之層的起伏。藉此,所得到之有機EL元件,具有可防止輝度不均等的高性能。
又,在另一實施態樣中,使用上述電子材料組成物形成發光層的情況下,所得到之有機EL元件,可實現高驅動穩定性。
以下列舉實施例具體說明本發明。
<矽氧烷單體之合成>
[實施例1]
將100g的SILAPLANE FM-0411(JNC股份有限公司製)與16.8g的三級丁醇鉀投入經以裝有100g之四氫呋喃(THF)的以氬氣進行取代的500mL之三頸燒瓶,在室溫下攪拌1小時。於其中滴下11.8g的5-溴基-1,3-戊二烯,在室溫下攪拌18小時。之後,減壓餾去THF,以甲苯進行萃取,並以水進行洗淨3次後,以硫酸鈉進行乾燥。之後,以矽膠管柱層析法進行純化,得到本發明之矽氧烷單體a。產量為18g。
矽氧烷單體a的結構顯示如下。
[實施例2]
除了使用12.2g的4-(氯甲基)苯乙烯代替5-溴-1,3-戊二烯外,以與實施例1同樣的方法,合成本發明之矽氧烷單體b。產量為12g。
矽氧烷單體b之結構顯示如下。
<聚合物之合成>
[實施例3]
將700mg的苯乙烯與672mg之於實施例1所得的矽氧烷單體a、27.6mg的Perbutyl Z(日本油脂股份有限公司製)、3.3g的環己酮裝入10mL的三頸燒瓶中,於裝入氮氣下,於110℃下攪拌30小時。將所得到之反應液滴入甲醇,使聚合物沈澱後,藉由過濾、乾燥得到本發明之聚合物A1.3g。
測定所得到之聚合物A的數量平均分子量(Mn)及重量平均分子量(Mw),分別為7,900及20,000。此外,數量平均分子量及重量平均分子量係使用高速GPC裝置(TOSOH股份有限公司製)以聚苯乙烯作為標準物質來測定。
[實施例4]
除了使用於實施例2所得到之矽氧烷單體b代替矽氧烷單體a外,以與實施例3同樣的方法,合成本發明之聚合物B。
測定所得到之聚合物B的數量平均分子量(Mn)及重量平均分子量(Mw),分別為8,100及21,000。
[實施例5]
除了使用苄基乙烯基醚代替苯乙烯外,以與實施例4同樣的方法,合成本發明之聚合物C。
測定所得到之聚合物C的數量平均分子量(Mn)及重量平均分子量(Mw),分別為8,500及22,000。
[合成例1]
除了使用FM-0711代替矽氧烷單體A外,以與實施例
3同樣的方法,合成聚合物D。
測定所得到之聚合物D的數量平均分子量(Mn)及重量平均分子量(Mw),分別為9,500及24,000。
FM-0711之結構顯示如下。
<主體材料之合成>
[合成例2]中間體1之合成
於250mL的四頸燒瓶中依序加入1,2,3,4-四氫咔唑(12g,72mmol)、活性碳(12g)、1,2-二氯苯120mL,一邊以500mL/分鐘加入空氣,一邊於150℃下攪拌反應液15小時。將反應液冷卻至室溫後,過濾反應液,減壓去除有機溶劑,以管柱層析法進行純化。減壓去除有機溶劑後,得到黃色固體(中間體1)3.2g(產率:10%)。
[合成例3]9,9’-(對三級丁基苯)-1,3-雙咔唑的合成
在氬氣環境下,於200mL的三頸燒瓶中依序加入中間體1(0.836g,2.52mmol)、1-溴基4-三級丁基苯(1.287g,6.04mmol)、參(二亞苄基)二鈀(0.130g,0.13mmol)、三-三級丁基膦(0.076g,0.38mmol)、三級丁醇鈉(0.725g,7.55mmol)、甲苯50mL,並加熱回流8小時。將反應液冷卻至室溫後,加入水並以分液漏斗回收有機層。減壓去除有機溶劑後,以矽膠層析法進行純化,得到白色固體(化合物6)0.9g(產率60%)。
<電子材料組成物之製造>
使用於實施例3~5所得到之本發明之聚合物A~C、以及合成例1所得到之聚合物D,製作使用發光材料之電子材料組成物作為有機EL材料。
[實施例6]
使0.001g的實施例3所合成之聚合物A溶解於溶劑9.9g之四氫化萘。於所得到之溶液中添加0.04g的參[2-(對甲苯基)吡啶]銥(Ir(mppy)3)(Lumtec公司製)與合成例3所合成的0.26g之9,9’-(對三級丁基苯)-1,3-雙咔唑,以60℃進行加熱,藉此製造電子材料組成物。
[實施例7]
除了將聚合物A變更成於實施例4合成的聚合物B外,以與實施例6同樣的方法製造電子材料組成物。
[實施例8]
除了將聚合物A變更成於實施例5合成的聚合物C外,以與實施例6同樣的方法製造電子材料組成物。
[比較例]
除了將聚合物A變更成於合成例1所得到之聚合物D外,以與實施例6同樣的方法製造電子材料組成物。
<評價>
針對於實施例6~8及比較例所製造之電子材料組成物進行以下之各種評價。
[平滑性評價]
於銦錫氧化物(ITO)基板上滴下0.1μL之電子材料組成物,於25℃、1Torr減壓乾燥。使用光干涉表面形狀計測裝置(菱化系統股份有限公司製)測定所得到之有機薄膜的凸部及凹部之差(凹凸差),根據以下之基準進行評價。此外,前述所謂的凸部係指有機薄膜表面中以水平面為基準之最高者,前述所謂的凹部係指有機薄膜表面中以水平面為基準之最低者。
[發光效率評價]
製作有機EL元件,評價所得到之有機發光元件的發光效率。
以下述方式製作有機EL元件。
亦即,對經洗淨之ITO基板照射UV/O3,藉由旋轉塗布將聚(3,4-伸乙基二氧噻吩)-聚(苯乙烯磺酸)(PEDOT-PSS)形成45nm的薄膜,於大氣中、180℃下加熱15分鐘,形成電洞注入層。接著,藉由旋轉塗布,於電洞注入層上將下式所表示之HT-2的0.3重量%二甲苯溶液形成10nm的薄膜,於氮氣環境下、200℃下使其乾燥30分鐘,藉此形成電洞輸送層。接著,藉由旋轉塗布,將實施例6~8及比較例所得到之電子材料組成物形成
30nm之膜於電洞輸送層上,於25℃、1Torr下進行減壓乾燥3分鐘後,於氮氣環境下、110℃下使其乾燥15分鐘,藉此形成發光層。接著,於5×10-3Pa的真空條件下,依序形成45nm的下式所表示之ET-1作為電子輸送層、形成0.5nm的氟化鋰作為電子注入層、形成100nm的鋁作為陰極。最後,將基板移送至手套工作箱,並以玻璃基板進行密封,藉此製作有機發光元件。
[發光效率]
使用製作之有機EL元件評價發光效率。
更詳細來說,對所製作之有機EL元件,將其與外部電源連接,以BM-9(TOPCON股份有限公司製)對來自有機EL元件的發光進行測光。此時,從電流值算出10mA/cm2時的發光效率。
[壽命]
使用製作之有機EL元件,評價壽命。
更詳細來說,對所製作之有機EL元件,施加10mA/cm2的電流,以光電二極體式壽命測定裝置(System
Engineers股份有限公司製)測定輝度半衰期。
所得到之結果示於下述表1。
從上述表1之結果可看出來,與比較例相比,使用實施例6~8之電子材料組成物形成塗膜的情形可以得到凹凸差少的膜,元件壽命提升。亦即,可知曉藉由使用本發明之電子材料組成物,所得到之塗膜的平滑性可被改善,並顯示優異的元件之驅動穩定性。
Claims (6)
- 一種以通式(1)所示之單體,
- 一種聚合物,其係將至少選自該通式(1)之單體聚合而成。
- 一種聚合物,其係將至少選自該通式(1)之單體及通式(1)以外之單體共聚合而成。
- 一種組成物,其特徵在於含有如請求項2或3之聚合物。
- 一種電子材料組成物,其特徵在於含有如請求項2或3之聚合物。
- 一種電子元件,其特徵在於含有如請求項4之組成物或如請求項5之電子材料組成物。
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US6649722B2 (en) * | 1999-12-10 | 2003-11-18 | Novartis Ag | Contact lens |
JP2007137944A (ja) * | 2005-11-15 | 2007-06-07 | Fujifilm Corp | 硬化性樹脂組成物、硬化膜、反射防止フィルム、偏光板、及び表示装置 |
JP2007153914A (ja) * | 2005-11-30 | 2007-06-21 | Fujifilm Corp | 硬化性組成物、フィルム、偏光板および画像表示装置 |
JP2007238675A (ja) * | 2006-03-06 | 2007-09-20 | Fujifilm Corp | 硬化性組成物、硬化性組成物の製造方法、光学フィルム、反射防止フィルム、偏光板、および画像表示装置 |
JP2010249933A (ja) * | 2009-04-13 | 2010-11-04 | Konica Minolta Business Technologies Inc | クリアトナー、画像形成方法 |
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