TWI708765B - 2,5-二氰基-3,6-二鹵吡𠯤之製造方法 - Google Patents
2,5-二氰基-3,6-二鹵吡𠯤之製造方法 Download PDFInfo
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- TWI708765B TWI708765B TW109110889A TW109110889A TWI708765B TW I708765 B TWI708765 B TW I708765B TW 109110889 A TW109110889 A TW 109110889A TW 109110889 A TW109110889 A TW 109110889A TW I708765 B TWI708765 B TW I708765B
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- ring
- unsubstituted
- dicyano
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- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 125000003118 aryl group Chemical group 0.000 claims abstract description 41
- WPJNZXXVNODVDC-UHFFFAOYSA-N 3,6-diaminopyridine-2,5-dicarbonitrile Chemical compound NC1=CC(C#N)=C(N)N=C1C#N WPJNZXXVNODVDC-UHFFFAOYSA-N 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 16
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- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000005658 halogenation reaction Methods 0.000 claims description 6
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- 229910052799 carbon Inorganic materials 0.000 abstract description 19
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
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Abstract
一種式(I)或式(II)表示之化合物。
[式(I)中之R3
表示供電子基,R4
表示氫原子、經取代或未經取代之芳基或供電子基,L3
表示經取代或未經取代之伸雜芳基(heteroarylene group)、或者經取代或未經取代之伸芳基,L4
表示單鍵、經取代或未經取代之伸雜芳基、或者經取代或未經取代之伸芳基。L3
與L4
亦可連接而與該等所鍵結之碳原子一起形成環。]
[式(II)中之R5
表示供電子基,R6
表示氫原子、經取代或未經取代之芳基或供電子基,L5
表示經取代或未經取代之伸雜芳基、或者經取代或未經取代之伸芳基,L6
表示單鍵、經取代或未經取代之伸雜芳基、或者經取代或未經取代之伸芳基。]
Description
本案係基於2015年11月10日於日本提出申請之特願2015-220371號及2015年12月11日於日本提出申請之特願2015-242690號主張優先權,並將該等之內容引用至本文中。
例如,專利文獻1揭示有一種有機固體螢光物質,其含有藉由後分光方式之反射率測定所獲得之固體於可見光區域之最大反射率為100%以上之式(1)表示之N,N,N',N'-四(2-甲基苄基)-2,5-二胺基-3,6-吡腈(N,N,N',N'-tetrakis(2-methylbenzyl)-2,5-diamino-3,6-pyrazinecarbonitrile)結晶。
專利文獻2揭示有一種膜,其係於式(2)表示之1,4,5,8,9,11-六氮雜聯三伸苯六甲腈(1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile)中添加包含式(3)表示之喹啉骨架或式(4)表示之2,3-二氰基吡骨架之化合物而成。上述膜似可用於有機電致發光元件或有機薄膜太陽電池等有機電子裝置。
式(5)中,R1及R2分別獨立地表示亦可具有取代基之雜環基或亦可具有取代基之烴環基。
專利文獻4揭示有一種式(6)等所表示之化合物。上述化合物似可用於電子傳輸材料、電荷產生材料、光學記錄材料、光電轉換材料等。
專利文獻5及6揭示有一種式(7)或式(8)等所表示之化合物。該等化合物似可用於電致發光、波長轉換材料等功能性材料。
專利文獻7揭示有一種由作為拉電子性部位之氰基吡啶與作為供
電子性部位之雜芳基鍵結而成之化合物所構成的發光材料。
製造具有供電子基之包含二氰基吡骨架之化合物之方法可列舉多種。為了廉價且以高產率獲得具有供電子基之包含二氰基吡骨架之化合物,必須研究起始原料或中間體。考慮到各種起始原料或中間體之候選者。例如,6-胺基吡-2,3,5-三甲腈、5,6-二胺基吡-2,3-二甲腈、3,5-二胺基吡-2,6-二甲腈、3,6-二胺基吡-2,5-二甲腈等具有胺基及氰基之吡化合物可以二胺順丁烯二腈或其同族體作為起始原料進行合成(非專利文獻2、專利文獻8、專利文獻9等)。
作為具有胺基及鹵基(halogeno group)之吡化合物,例如市售有2-胺基-6-氯吡、2-胺基-5-氯吡、2-胺基-5-溴吡及2-胺基-3,5-二溴吡,容易獲取。2-胺基-溴吡類可藉由如下方法進行合成:於溶劑中,於脫溴化氫劑之存在下,使吡核具有至少1個氫原子之2-胺基吡類與溴進行反應(專利文獻11)。該溴化係自氫向溴之取代反應。
作為具有氰基及溴基之吡化合物,例如,2,5-二氰基-3,6-二溴吡可自2-氰基-3-胺基吡藉由4個階段之反應而獲得,或者,自2-氰基-3-胺基-6-溴吡藉由3個階段之反應而獲得(非專利文獻1)。2-氰基-3-胺基吡係藉由非專利文獻3記載之方法而獲得。具有氰基及溴基之吡化合物之合成必需多階段之反應。
[專利文獻1]日本特開2007-204443號公報
[專利文獻2]日本特開2015-153864號公報
[專利文獻3]日本特開2001-261658號公報
[專利文獻4]日本特開2001-2661號公報
[專利文獻5]日本特開平5-32640號公報
[專利文獻6]日本特開平11-138974號公報
[專利文獻7]日本特開2015-172166號公報
[專利文獻8]日本特願昭63-75909號
[專利文獻9]WO 91/03469 A
[專利文獻10]WO 88/01264 A
[專利文獻11]日本特開2001-89460號公報
[非專利文獻1]N. Sato et al. "Synthesis of 3,6 - Dibromopyrazine - 2,5 - dicarbonitrile" Journal of Heterocyclic Chemistry, Vol.49, May 2012,675 -
[非專利文獻2]J. Org. Chem., Vol.39, 1235 - (1974)
[非專利文獻3]Journal of Heterocyclic Chemistry, Vol.26, 1989, 817 -
為了解決上述課題而進行努力研究,結果完成包含以下之形態之本發明。
即,本發明包含以下之形態。
[1]一種化合物,其係以式(I)或式(II)表示。
[式(I)中之R3表示供電子基,R4表示氫原子、經取代或未經取代之芳基或供電子基,L3表示經取代或未經取代之伸雜芳基(heteroarylene group)、或者經取代或未經取代之伸芳基,L4表示單鍵、經取代或未經取代之伸雜芳基、或者經取代或未經取代之伸芳基;L3與L4亦可連接而與該等所鍵結之碳原子一起形成環]
[式(II)中之R5表示供電子基,R6表示氫原子、經取代或未經取代之芳基或供電子基,L5表示經取代或未經取代之伸雜芳基、或者經取代或未經取代之伸芳基,L6表示單鍵、經取代或未經取代之伸雜芳基、或者經取代或未經取代
之伸芳基]
[2]如[1]記載之化合物,其中,R3及R5係選自由式(d1)~式(d7)表示之基組成之群中的至少一者。
(式(d1)~(d7)中,R表示取代基,a及b分別獨立地表示括號內之R之數量,且為0~4之任一整數;c表示括號內之R之數量,且為0~2之任一整數;d表示括號內之R之數量,且為0~5之任一整數;於複數個R進行取代時,該等可為相同之取代基,亦可為不同之取代基;鄰接之2個R亦可連接而與上述R所鍵結之碳原子一起形成環;*表示鍵結鍵)
[3]如[1]或[2]記載之化合物,其中,R4及R6係選自由式(d1)~式(d7)表示之基組成之群中的至少一者。
[4]如[1]、[2]或[3]記載之化合物,其中,L3、L4、L5及L6分別獨立地為經取代或未經取代之伸芳基。
[5]一種發光材料,其包含上述[1]至[4]中任一項記載之化合物。
[6]一種發光元件,其含有上述[5]記載之發光材料。
[7]一種2,5-二氰基-3,6-二鹵吡(式(11))之製造方法,其包括:於氧之存在下、溶劑中、酸性條件下使(2E)-2,3-二胺基-3-(取代氫硫基)-2-丙烯腈進行反應,獲得2,5-二氰基-3,6-二胺基吡;於亞硝酸或亞硝酸鹽之存在下,於溶劑中使2,5-二氰基-3,6-二胺基吡
(式(10))進行鹵化反應。
式(11)中之X表示鹵素原子。
[8]如[7]記載之製造方法,其中,(2E)-2,3-二胺基-3-(取代氫硫基)-2-丙烯腈係式(9)表示之化合物。
(式(9)中,R表示經取代或未經取代之芳基、經取代或未經取代之烷基、經取代或未經取代之芳烷基(aralkyl group)、或者經取代或未經取代之烯基)
[10]如[7]至[9]中任一項記載之製造方法,其進一步包括將鹵化反應時之溫度設為30~60℃。
[圖1]係表示Ac-CNP甲苯溶液A、Ac-CNP有機光致發光元件B及Ac-CNP有機光致發光元件C之吸收發射光譜之圖。
[圖2]係表示Ac-CNP有機光致發光元件C之暫態衰減曲線之圖。
[圖3]係表示Ac-CNP有機電致發光元件之膜構成之圖。
[圖4]係表示Ac-CNP有機電致發光元件之發射光譜之圖。
[圖5]係表示Ac-CNP有機電致發光元件之電壓-電流密度-發光強度特性之圖。
[圖6]係表示Ac-CNP有機電致發光元件之電流密度-外部量子效率特性之圖。
[圖7]係表示Px-CNP有機光致發光元件C之暫態衰減曲線之圖。
[圖8]係表示Px-CNP有機電致發光元件之膜構成之圖。
[圖9]係表示Px-CNP有機電致發光元件之發射光譜之圖。
[圖10]係表示Px-CNP有機電致發光元件之電壓-電流密度-發光強度特性之圖。
[圖11]係表示Px-CNP有機電致發光元件之電流密度-外部量子效率特性之圖。
[圖12]係表示BCz-CNP有機光致發光元件C之暫態衰減曲線之圖。
[圖13]係表示BCz-CNP有機電致發光元件之膜構成之圖。
[圖14]係表示PCz-DCP有機光致發光元件B及PCz-DCP有機光致發光元件C之吸收發射光譜之圖。
[圖15]係表示PCz-DCP有機光致發光元件C之暫態衰減曲線之圖。
[圖16]係表示PCz-DCP有機電致發光元件(器件B)之膜構成之圖。
[圖17]係表示PCz-DCP有機電致發光元件(器件A)之膜構成之圖。
[圖18]係表示PCz-DCP有機電致發光元件(器件B及器件A)之發射光譜之圖。
[圖19]係表示PCz-DCP有機電致發光元件(器件B及器件A)之電壓-電流密度-發光強度特性之圖。
[圖20]係表示PCz-DCP有機電致發光元件(器件B及器件A)之電流密度-外部量子效率特性之圖。
[圖21]係表示PAc-DCP有機光致發光元件C之暫態衰減曲線之圖。
[圖22]係表示PAc-DCP有機電致發光元件(器件B)之膜構成之圖。
[圖23]係表示PAc-DCP有機電致發光元件(器件A)之膜構成之圖。
[圖24]係表示PAc-DCP有機電致發光元件(器件B及器件A)之發射光譜之圖。
[圖25]係表示PAc-DCP有機電致發光元件(器件B及器件A)之電壓-電流密度-發光強度特性之圖。
[圖26]係表示PAc-DCP有機電致發光元件(器件B及器件A)之電流密度-外部量子效率特性之圖。
[式(I)中之R3表示供電子基,R4表示氫原子、經取代或未經取代之芳基或
供電子基,L3表示經取代或未經取代之伸雜芳基、或者經取代或未經取代之伸芳基,L4表示單鍵、經取代或未經取代之伸雜芳基、或者經取代或未經取代之伸芳基;L3與L4亦可連接而與該等所鍵結之碳原子一起形成環]
[式(II)中之R5表示供電子基,R6表示氫原子、經取代或未經取代之芳基或供電子基,L5表示經取代或未經取代之伸雜芳基、或者經取代或未經取代之伸芳基,L6表示單鍵、經取代或未經取代之伸雜芳基、或者經取代或未經取代之伸芳基]
於本發明中,用語「未經取代(unsubstituted)」意指僅為成為母核之基。於僅以成為母核之基之名稱進行記載時,只要未特別說明則為「未經取代」之含義。
另一方面,用語「經取代(substituted)」意指成為母核之基之任一氫原子經與母核相同或不同之結構的基取代。因此,「取代基」係鍵結於成為母核之基之其他基。取代基可為1個,亦可為2個以上。2個以上之取代基可相同,亦可不同。
「取代基」只要於化學上容許,且具有本發明之效果,則並無特別限制。
作為可成為「取代基」之基之具體例,可列舉以下之基。
氟基、氯基、溴基、碘基等鹵素基;甲基、乙基、正丙基、異丙基、正丁基、二級丁基、異丁基、三級丁基、正戊基、正己基等C1~6烷基;乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1
-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基等C2~6烯基;乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、2-甲基-3-丁炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-2-丁炔基、2-甲基-3-戊炔基、1-己炔基、1,1-二甲基-2-丁炔基等C2~6炔基;環丙基、環丁基、環戊基、環己基、環庚基、立方烷基(cubanyl group)等C3~8環烷基;2-環丙烯基、2-環戊烯基、3-環己烯基、4-環辛烯基等C3~8環烯基;苯基、萘基等C6~10芳基;吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、唑基、異唑基、噻唑基、異噻唑基、三唑基、二唑基(oxadiazolyl group)、噻二唑基(thiadiazolyl group)、四唑基等5員環之雜芳基;吡啶基、吡基、嘧啶基、嗒基、三基等6員環之雜芳基;吲哚基、苯并呋喃基、苯并噻吩基、苯并咪唑基、苯并唑基、苯并噻唑基、喹啉基、異喹啉基、喹啉基等縮合環之雜芳基;氧雜環丙基(oxiranyl group)、四氫呋喃基、二氧雜環戊基(dioxolanyl group)、二氧雜環己基(dioxanyl group)等環狀醚基;氮丙啶基(aziridinyl group)、吡咯啶基、哌啶基、哌基、啉基等環狀胺基;羥基;側氧基;甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、二級丁氧基、異丁氧基、三級丁氧基等C1~6烷氧基;
乙烯氧基、烯丙氧基、丙烯氧基、丁烯氧基等C2~6烯氧基;乙炔氧基、炔丙氧基等C2~6炔氧基;苯氧基、萘氧基等C6~10芳氧基;噻唑氧基、吡啶氧基等5~6員環之雜芳氧基;羧基;甲醯基、乙醯基、丙醯基等C1~6烷基羰基;甲醯氧基、乙醯氧基、丙醯氧基等C1~6烷基羰氧基;甲氧基羰基、乙氧基羰基、正丙氧基羰基、異丙氧基羰基、正丁氧基羰基、三級丁氧基羰基等C1~6烷氧基羰基;氯甲基、氯乙基、三氟甲基、1,2-二氯正丙基、1-氟正丁基、全氟正戊基等C1~6鹵化烷基;2-氯-1-丙烯基、2-氟-1-丁烯基等C2~6鹵化烯基;4,4-二氯-1-丁炔基、4-氟-1-戊炔基、5-溴-2-戊炔基等C2~6鹵化炔基;3,3-二氟環丁基等C3~6鹵化環烷基;2-氯正丙氧基、2,3-二氯丁氧基、三氟甲氧基、2,2,2-三氟乙氧基等C1~6鹵化烷氧基;2-氯丙烯氧基、3-溴丁烯氧基等C2~6鹵化烯氧基;氯乙醯基、三氟乙醯基、三氯乙醯基等C1~6鹵化烷基羰基;氰基;硝基;胺基;甲基胺基、二甲基胺基、二乙基胺基等C1~6烷基胺基;苯胺基、萘基胺基等C6~10芳基胺基;甲醯基胺基、乙醯基胺基、丙醯基胺基、丁醯基胺基、異丙基羰基胺基等C1~6烷基羰基胺基;
甲氧基羰基胺基、乙氧基羰基胺基、正丙氧基羰基胺基、異丙氧基羰基胺基等C1~6烷氧基羰基胺基;S,S-二甲基磺醯亞胺基(S,S-dimethyl sulfoxyimino group)等C1~6烷基磺醯亞胺基;胺基羰基;甲基胺基羰基、二甲基胺基羰基、乙基胺基羰基、異丙基胺基羰基等C1~6烷基胺基羰基;亞胺基甲基、(1-亞胺基)乙基、(1-亞胺基)正丙基等亞胺基C1~6烷基;羥基亞胺基甲基、(1-羥基亞胺基)乙基、(1-羥基亞胺基)丙基等羥基亞胺基C1~6烷基;甲氧基亞胺基甲基、(1-甲氧基亞胺基)乙基等C1~6烷氧基亞胺基C1~6烷基;巰基;甲基硫基、乙基硫基、正丙基硫基、異丙基硫基、正丁基硫基、異丁基硫基、二級丁基硫基、三級丁基硫基等C1~6烷基硫基;三氟甲基硫基、2,2,2-三氟乙基硫基等C1~6鹵化烷基硫基;乙烯基硫基、烯丙基硫基等C2~6烯基硫基;乙炔基硫基、炔丙基硫基等C2~6炔基硫基;甲基亞磺醯基、乙基亞磺醯基、三級丁基亞磺醯基等C1~6烷基亞磺醯基;三氟甲基亞磺醯基、2,2,2-三氟乙基亞磺醯基等C1~6鹵化烷基亞磺醯基;烯丙基亞磺醯基等C2~6烯基亞磺醯基;炔丙基亞磺醯基等C2~6炔基亞磺醯基;甲基磺醯基、乙基磺醯基、三級丁基磺醯基等C1~6烷基磺醯基;三氟甲基磺醯基、2,2,2-三氟乙基磺醯基等C1~6鹵化烷基磺醯基;
烯丙基磺醯基等C2~6烯基磺醯基;炔丙基磺醯基等C2~6炔基磺醯基;三甲基矽基、三乙基矽基、三級丁基二甲基矽基等三C1~6烷基矽基;三苯基矽基等三C6~10芳基矽基;又,對於該等「取代基」,上述取代基中之任一個氫原子亦可被不同結構之基取代。
「C1~6」等用語表示成為母核之基之碳原子數為1~6個等。該碳原子數不包括取代基中存在之碳原子之數。例如,關於乙氧基丁基,由於成為母核之基為丁基且取代基為乙氧基,故而分類為C2烷氧基C4烷基。
式(I)或式(II)中之R3、R4、R5或R6中之供電子基係具有對吡環供應電子之性質的原子或原子團。上述供電子基較佳為哈密特(Hammett)之σp值未達0。哈密特之σp值係將取代基對對位取代苯衍生物之反應速度或平衡造成之影響進行定量化。具體而言,哈密特之σp值係藉由式(h1)或(h2)之任一者定義之值。
log(k/k0)=ρ.σp (h1)
log(K/K0)=ρ.σp (h2)
k為未經取代之苯衍生物之反應速度常數,k0為經取代之苯衍生物之反應速度常數,K為未經取代之苯衍生物之平衡常數,K0為經取代之苯衍生物之平衡常數,ρ係根據反應之種類及條件而決定之反應常數。關於與哈密特之σp值相關之詳細之說明及各取代基之值,可參照J.A.Dean編寫之「Lange's Handbook of Chemistry第13版」,1985年,3-132~3-137頁,McGrow-Hill。
作為R3、R4、R5或R6中之供電子基,例如可列舉含有雜原子且哈密特之σp值未達0者。作為雜原子,可列舉:氮原子、氧原子、硫原子、矽原子、
磷原子等。較佳之供電子基係於雜原子具有鍵結鍵之基、或具有「雜原子之至少1個與sp2碳原子鍵結而使包含上述sp2碳原子之π共軛擴展至吡環」之結構的基。
作為於雜原子具有鍵結鍵之基,可列舉:經取代或未經取代之二芳基胺基、經取代或未經取代之二烷基胺基、經取代或未經取代之烷基芳基胺基、經取代或未經取代之環狀胺基、經取代或未經取代之芳氧基、經取代或未經取代之烷氧基、經取代或未經取代之芳硫基、經取代或未經取代之烷硫基、經取代或未經取代之三芳基矽基、經取代或未經取代之烷基二芳基矽基、經取代或未經取代之二烷基芳基矽基、經取代或未經取代之三烷基矽基、經取代或未經取代之環狀矽基、經取代或未經取代之二芳基膦基、經取代或未經取代之二烷基膦基、經取代或未經取代之環狀膦基等。
作為具有「雜原子之至少1個與sp2碳原子鍵結而使包含上述sp2碳原子之π共軛擴展至吡環」之結構的基,可列舉:經於雜原子具有鍵結鍵之基取代之芳基;經於雜原子具有鍵結鍵之基取代之雜芳基;經具有雜原子鍵結於sp2碳原子之結構之基取代之芳基,其具有包含上述sp2碳原子之π共軛經由上述芳基擴展至吡環之結構;經具有雜原子鍵結於sp2碳原子之結構之基取代之雜芳基,其具有包含上述sp2碳原子之π共軛經由上述雜芳基擴展至吡環之結構;經具有雜原子鍵結於sp2碳原子之結構之基取代之烯基,其具有包含上述sp2碳原子之π共軛經由上述烯基擴展至吡環之結構;經具有雜原子鍵結於sp2碳原子之結構之基取代之炔基,其具有包含上述sp2碳原子之π共軛經由上述炔基擴展至吡環之結構;等。
作為R3、R4、R5或R6中之供電子基,較佳者係於雜原子具有鍵結鍵之基;經於雜原子具有鍵結鍵之基取代之芳基;經於雜原子具有鍵結鍵之基取代之雜芳基;經具有雜原子鍵結於sp2碳原子之結構之基取代之芳基,其具有
包含上述sp2碳原子之π共軛經由上述芳基擴展至吡環之結構;或經具有雜原子鍵結於sp2碳原子之結構之基取代之雜芳基,其具有包含上述sp2碳原子之π共軛經由上述雜芳基擴展至吡環之結構;更佳者係於雜原子具有鍵結鍵之基;經於雜原子具有鍵結鍵之基取代之芳基;或經具有雜原子鍵結於sp2碳原子之結構之基取代之芳基,其具有包含上述sp2碳原子之π共軛經由上述芳基擴展至吡環之結構。
作為供電子基之構成要素之芳基可為單環或多環之任一者。多環芳基只要至少一個環為芳香環即可,其餘環可為飽和環、不飽和環或芳香環之任一者。構成未經取代之芳基之碳原子之數量較佳為6~40,更佳為6~20,進一步較佳為6~14。
作為未經取代之芳基,可列舉:苯基、1-萘基、2-萘基、薁基、二氫茚基、四氫萘基(Tetralinyl)等。
作為經取代之芳基,可列舉:4-氟苯基、4-氯苯基、2,4-二氯苯基、3,4-二氯苯基、3,5-二氯苯基、2,6-二氟苯基、4-三氟甲基苯基、4-甲氧基苯基、3,4-二甲氧基苯基、3,4-亞甲基二氧基苯基、4-三氟甲氧基苯基、4-甲氧基-1-萘基等。
作為供電子基之構成要素之雜芳基可為單環或多環之任一者。多環雜芳基只要至少一個環為雜芳香環即可,其餘環可為飽和環、不飽和環或芳香環之任一者。構成未經取代之雜芳基之原子之數量較佳為5~40,更佳為5~20,進一步較佳為5~14。
作為未經取代之雜芳基,可列舉:吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、唑基、異唑基、噻唑基、異噻唑基、三唑基、二唑基、噻二唑基、四唑基等5員環之雜芳基;吡啶基、吡基、嘧啶基、嗒基、三基等6員環之雜芳基;吲哚基、苯并呋喃基、苯并噻吩基、苯并咪唑基、苯并唑基、苯
并噻唑基、喹啉基、異喹啉基、喹啉基等縮合環之雜芳基等。
作為供電子基之構成要素之烯基於分子中具有至少一個碳-碳雙鍵。作為烯基,可列舉:乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基等。
作為供電子基之構成要素之炔基於分子中具有至少一個碳-碳三鍵。作為炔基,可列舉:乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、2-甲基-3-丁炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-2-丁炔基、2-甲基-3-戊炔基、1-己炔基、1,1-二甲基-2-丁炔基等。
R3、R4、R5或R6中之供電子基較佳為選自由式(d1)~式(d7)表示之基組成之群中的至少一者,更佳為選自由式(d2)、式(d3)及式(d6)表示之基組成之群中的至少一者。
(式(d1)~(d7)中,R表示取代基,a及b分別獨立地表示括號內之R之數量,且為0~4之任一整數,較佳為0或1,更佳為0;c表示括號內之R之數量,且為0~2之任一整數,較佳為0;d表示括號內之R之數量,且為0~5之任一整數,較佳為0;於複數個R進行取代時,該等可為相同之取代基,亦可為不同之取代
基;鄰接之2個R亦可連接而與上述R所鍵結之碳原子一起形成環;*表示鍵結鍵)
作為R,較佳為羥基、鹵基、C1~20烷基、C1~20烷氧基、C1~20烷硫基、C1~20烷基取代胺基、C6~40芳基取代胺基、C6~40芳基、5~40員雜芳基、C2~10烯基、C2~10炔基、C2~20烷基醯胺基、C6~20芳基醯胺基、三C1~10烷基矽基,較佳為C1~20烷基、C1~20烷氧基、C1~20烷硫基、C1~20烷基取代胺基、C6~40芳基取代胺基、C6~40芳基、5~40員雜芳基,更佳為C6~40芳基。
作為鄰接之2個R連接而形成之環,可列舉:苯環、萘環、吡啶環、嗒環、嘧啶環、吡環、吡咯環、咪唑環、吡唑環、咪唑啉環、唑環、異唑環、噻唑環、異噻唑環、環己二烯環、環己烯環、環戊烯環、環庚三烯環、環庚二烯環、環庚烯環等。
R4或R6中之經取代或未經取代之芳基可為單環或多環之任一者。多環芳基只要至少一個環為芳香環即可,其餘環可為飽和環、不飽和環或芳香環之任一者。構成未經取代之芳基之碳原子之數量較佳為6~40,更佳為6~20,進一步較佳為6~14。
作為未經取代之芳基,可列舉:苯基、1-萘基、2-萘基、薁基、二氫茚基、四氫萘基等。
作為經取代之芳基,可列舉:4-氟苯基、4-氯苯基、2,4-二氯苯基、3,4-二氯苯基、3,5-二氯苯基、2,6-二氟苯基、4-三氟甲基苯基、4-甲氧基苯基、3,4-二甲氧基苯基、3,4-亞甲基二氧基苯基、4-三氟甲氧基苯基、4-甲氧基-1-萘基等。
L3、L4、L5或L6中之經取代或未經取代之伸芳基可為單環或多環之任一者。多環伸芳基只要至少一個環為芳香環即可,其餘環可為飽和環、不飽和環或芳香環之任一者。構成未經取代之伸芳基之碳原子之數量較佳為6~
40,更佳為6~20,進一步較佳為6~14。
作為伸芳基,可列舉:伸苯基、伸萘基、伸薁基、伸二氫茚基、伸四氫萘基等,其中尤佳為伸苯基。
L3、L4、L5或L6中之經取代或未經取代之伸雜芳基可為單環或多環之任一者。多環伸雜芳基只要至少一個環為雜芳香環即可,其餘環可為飽和環、不飽和環或芳香環之任一者。構成未經取代之伸雜芳基之原子之數量較佳為5~40,更佳為5~20,進一步較佳為5~14。
作為伸雜芳基,可列舉:伸吡咯基、伸呋喃基、伸噻吩基、伸咪唑基、伸吡唑基、伸唑基、伸異唑基、伸噻唑基、伸異噻唑基、伸三唑基、伸二唑基、伸噻二唑基、伸四唑基等5員環之伸雜芳基;伸吡啶基、伸吡基、伸嘧啶基、伸嗒基、伸三基等6員環之伸雜芳基;伸吲哚基、伸苯并呋喃基、伸苯并噻吩基、伸苯并咪唑基、伸苯并唑基、伸苯并噻唑基、伸喹啉基、伸異喹啉基、伸喹啉基等縮合環之伸雜芳基等。
作為L3與L4連接而形成之環,可列舉:苯環、萘環、吡啶環、嗒環、嘧啶環、吡環、吡咯環、咪唑環、吡唑環、咪唑啉環、唑環、異唑環、噻唑環、異噻唑環、環己二烯環、環己烯環、環戊烯環、環庚三烯環、環庚二烯環、環庚烯環等。
例如,式(I)表示之化合物可藉由如下式般,使二乙醯基化合物與二胺順丁烯二腈進行反應而獲得。
(例I-1)
於乙醇60ml中,於60℃於氮環境中使二胺順丁烯二腈(0.88g、8.2mmol)、1,2-雙(4-溴苯基)乙烷-1,2-二酮(3.0g、8.2mmol)及鹽酸(36%、1.5g)反應3小時。冷卻至室溫後,藉由二氯甲烷100ml及水100ml進行萃取。藉由無水硫酸鎂使分離之有機相乾燥,繼而進行過濾及蒸發,獲得淡紫色固體之5,6-雙(4-溴苯基)吡-2,3-二甲腈(3.2g、產率90%)。
1H NMR(500MHz,CDCl3,δ):7.58(dd,4H),7.46(dd,4H);MS(MALDI-TOF)m/z:[M]+ calcd for C18H8Br2N4,437.91;found,437.70.
供電子基等取代基可藉由苯環上之鹵基之取代反應等而導入。
(例I-2)
一面於甲苯30ml中攪拌5,6-雙(4-溴苯基)吡-2,3-二甲腈(1.0g、2.3mmol)、9,9-二甲基-9,10-二氫吖啶(1.05g、5.1mmol)、雙(三-三級丁基膦)鈀(0)(0.012g、0.023mmol)及碳酸鉀(0.95g、6.9mmol)一面於氮環境下使之回流72小時。冷卻至室溫,進行矽藻土(Celite)過濾,於減壓下去除溶劑。藉由矽膠-管柱層析法進行精製,獲得橙色固體之5,6-雙(4-(9,9-二甲基-9,10-二氫吖啶-10-基)-苯基)吡-2,3-二甲腈(0.60g、40%)。
1H NMR(500MHz,CDCl3,δ):7.87(dt,J=8.5Hz,2Hz,4H),7.47-7.43(m,8H),6.97-6.90(m,8H),6.35(dd,J=7.6Hz,1.3Hz,4H),1.66(s,12H);13C NMR(125MHz,CDCl3,δ):154.77,144.69,140.35,134.21,132.3,131.42,130.84,130.16,126.48,125.28,121.48,114.64,113.04,36.18,30.66;MS(MALDI-TOF)m/z:[M]+calcd for C48H36N6,696.30;found,696.49.Anal.calcd for C48H36N6:C,82.73;H,5.21;N,12.06;found:C,82.21;H,5.16;N,11.85.
(例I-3)
一面於甲苯30ml中攪拌5,6-雙(4-溴苯基)吡-2,3-二甲腈(1.0g、2.3mmol)、10H-啡(0.92g、5.1mmol)、雙(三-三級丁基膦)鈀(0)(0.012g、0.023mmol)及碳酸鉀(0.95g、6.9mmol)一面於氮環境下使之回流72小時。冷卻至室溫,進行矽藻土過濾,於減壓下去除溶劑。藉由矽膠-管柱層析法進行精製,獲得紅色固體之5,6-雙(4-(10H-啡-10-基)-苯基)吡-2,3-二甲腈(1.03g、70%)。
1H NMR(500MHz,CDCl3,δ):7.82(dt,J=8.5Hz,2Hz,4H),7.45(d,J=8.5Hz,4H),6.75-7.71(m,4H),6.70(td,J=7.5Hz,1Hz,4H),6.59(td,J=8.0Hz,1.5Hz,4H),5.97(dd,J=8.0Hz,1Hz,4H);13C NMR(125MHz,CDCl3,δ):154.52,144.15,140.34,134.21,133.43,132.48,131.33,123.38,122.15,115.91,113.24,122.85;MS(MALDI-TOF)m/z:[M]+ calcd for C42H24N6O2,644.21;found,644.43.Anal.calcd for C42H24N6O2:C,78.25;H,3.75;N,13.04;O,4.96;found:C,78.33;H,3.65;N,13.13.
(例I-4)
於氮環境下,於室溫下攪拌苯基肼(10.0g、92.5mmol)、α-四氫萘酮(13.5g、92.5mmol)及乙醇(100mL),繼而加入鹽酸(35%、15mL)。將所獲得之混合物於氮環境下於60℃攪拌3小時。冷卻至室溫,過濾固形物成分。獲得白色固體之6,11-二氫-5H-苯并[a]咔唑(18.2g、90%)。
1H NMR(500MHz,CDCl3):8.20(br s,1H),7.56(d,J=8.0Hz,1H),7.39(d,J=8.0Hz,1H),7.34(d,J=7.5Hz,1H),7.28-7.25(m,2H),7.20-7.15(m,2H),7.14(td,J=8.0Hz,1.0Hz,1H),3.09-2.97(m,4H).MS(MALDI-TOF):m/z 219.32[M]+;calcd 219.10.
於氮環境下,於室溫下攪拌6,11-二氫-5H-苯并[a]咔唑(10.0g、45.6mmol)及對二甲苯(100mL)。於其中慢慢加入載持於碳之鈀(10wt%、0.49g、4.56mmol)。使所獲得之混合物於氮環境下回流24小時。冷卻至室溫,進行矽藻土過濾,於減壓下去除溶劑。藉由甲醇進行清洗,獲得白色固體之11H-苯并[a]咔唑(8.92g、90%)。
1H NMR(500MHz,CDCl3):8.81(br s,1H),8.16(t,J=8.5Hz,3H),8.03(d,J=8.0Hz,1H),7.68(d,J=8.0Hz,1H),7.63(td,J=6.7Hz,1.25Hz,1H),7.56(td,J=8.0Hz,1.25Hz,1H),7.46(td,J=7.2Hz,1.25Hz,1.1H),7.33(td,J=8.0Hz,1.25Hz,0.8H).MS(MALDI-TOF):m/z 217.57[M]+;calcd 217.09.
一面於甲苯30ml中攪拌5,6-雙(4-溴苯基)吡-2,3-二甲腈(1.0g、2.3mmol)、11H-苯并[a]咔唑(1.11g、5.1mmol)、雙(三-三級丁基膦)鈀(0)(0.012g、0.023mmol)及碳酸鉀(0.95g、6.9mmol)一面於氮環境下使之回流72小時。冷卻至室溫,進行矽藻土過濾,於減壓下去除溶劑。藉由矽膠-管柱層析法進行精製,獲得橙色固體之5,6-雙(4-(11H-苯并[a]咔唑-11-基)-苯基)吡-2,3-二甲腈(0.50g、31%)。
Anal.calcd for C48H36N6:C,84.25;H,3.96;N,11.79;found:C,84.21;H,3.96;N,11.07.
(例I-5)
式(I)表示之化合物可藉由如下式般,使菲-9,10-二酮化合物與二胺順丁烯二腈進行反應而獲得。
供電子基等取代基可藉由苯環上之鹵基之取代反應等而導入。
(例I-6)
(例I-7)
(例I-8)
(例II-1)
(例II-2)
該等化合物之精製可藉由利用管柱層析儀之精製、利用矽膠、活性碳、活性白土等之吸附精製、利用溶劑之萃取法、再結晶或晶析法等而進行。化合物之結構可藉由將IR、NMR、質譜等之圖譜與已知之結構異構物進行比較而決定。
本發明之2,5-二氰基-3,6-二鹵吡之製造方法包括:(第一步驟)於氧之存在下、溶劑中、酸性條件下使(2E)-2,3-二胺基
-3-(取代氫硫基)-2-丙烯腈進行反應,獲得2,5-二氰基-3,6-二胺基吡,(第二步驟)於亞硝酸或亞硝酸鹽之存在下,於溶劑中使2,5-二氰基-3,6-二胺基吡進行鹵化反應。
式中之X表示鹵素原子,R表示經取代或未經取代之芳基、經取代或未經取代之烷基、經取代或未經取代之芳烷基、或者經取代或未經取代之烯基。R較佳為經取代或未經取代之芳基,更佳為苯基。
成為原料之(2E)-2,3-二胺基-3-(取代氫硫基)-2-丙烯腈(例如式(9)表示之化合物)可藉由專利文獻10等記載之方法而容易地合成。(2E)-2,3-二胺基-3-(取代氫硫基)-2-丙烯腈有於酸性液中形成酸性鹽之形態之情況。
因此,第一步驟之反應係(a)將(2E)-2,3-二胺基-3-(取代氫硫基)-2-丙烯腈溶解於酸性溶液中進行反應,或者(b)將(2E)-2,3二胺基-3-(取代氫硫基)-2-丙烯腈之酸性鹽溶解於溶劑中進行反應。
(a)反應通常可於有機溶劑中、或於有機溶劑與水之混合系統、pH調整用酸或緩衝液之存在下視需要一面通入空氣,一面於0~30℃附近於大氣壓下進行1小時至數小時。
作為有機溶劑,可列舉:苯、甲苯、二甲苯等烴類;乙腈等腈類;氯仿、二氯甲烷等鹵化烴類;乙酸乙酯等酯類;甲醇、乙醇等醇類;丙酮、甲基乙基酮等酮類;二乙醚、四氫呋喃、二烷、1,2-二甲氧基乙烷(DME)等醚類;二甲基甲醯胺、二甲基亞碸(DMSO)。該等有機溶劑可單獨使用1種或者
混合2種以上而使用。
作為酸性度之指標之pH較佳為1~5,更佳為2~4。為了調整pH,可使用無機酸、有機酸等任一種酸,較佳為使用各種緩衝液。
又,第一步驟之反應被認為係氧化性二聚化縮合反應。因此,必須使系統為氧化性之環境。通常,僅與大氣之氧接觸即可,較理想為積極地將空氣、氧等通入至反應系統。
於(b)反應中,可使用可溶解式(1)表示之化合物之酸性鹽之溶劑、例如乙腈、醇類、二甲基甲醯胺、二甲基亞碸等之類之極性溶劑或該等之混合溶劑。該等溶劑亦可含水。反應可於室溫下進行2~12小時,較理想為與(a)反應相同地通入空氣等而使反應系統為氧化性環境。
作為式(1)表示之化合物之酸性鹽,可列舉:鹽酸鹽、硫酸鹽、硝酸鹽、過氯酸鹽等無機酸鹽;對甲苯磺酸鹽、草酸鹽、苦味酸鹽、三氟乙酸鹽等有機酸鹽。
第二步驟之反應中所使用之亞硝酸鹽(nitrite)可列舉:亞硝酸鈉、亞硝酸鉀等亞硝酸金屬鹽;亞硝酸正丁酯、亞硝酸三級丁酯、亞硝酸異丁酯、亞硝酸戊酯、亞硝酸異戊酯、亞硝酸己酯、亞硝酸異戊酯等亞硝酸酯等。就精製之觀點而言,較佳為亞硝酸酯。一般,據說因亞硝酸或亞硝酸鹽之作用而進行胺基之重氮化,成為重氮鎓鹽。亞硝酸或亞硝酸鹽之使用量並無特別限制,相對於2,5-二氰基-3,6-二胺基吡1莫耳,較佳為2莫耳以上,更佳為2.5~5莫耳。
作為鹵化劑,可列舉:四氟硼酸、溴化銅(I)、溴化銅(II)、氯
化銅(I)、氯化銅(II)、碘化鉀等。鹵化劑之使用量只要為足以將2,5-二氰基-3,6-二胺基吡中之2個胺基進行溴化之量,則並無特別限定。
作為反應溶劑,可使用苯、甲苯、二甲苯等烴類;乙腈等腈類;氯仿、二氯甲烷等鹵化烴類;乙酸乙酯等酯類;甲醇、乙醇等醇類;丙酮、甲基乙基酮等酮類;二乙醚、四氫呋喃、二烷、1,2-二甲氧基乙烷(DME)等醚類;二甲基甲醯胺、二甲基亞碸(DMSO);又,亦可混合而使用。
於第二步驟之反應中,可將2,5-二氰基-3,6-二胺基吡添加至含鹵化劑及亞硝酸或亞硝酸鹽之溶液中,亦可於含2,5-二氰基-3,6-二胺基吡及鹵化劑之溶液中添加亞硝酸或亞硝酸鹽,或者亦可採用其他添加順序,就容易控制反應時之發熱及發泡而言,較佳為於含2,5-二氰基-3,6-二胺基吡及鹵化劑之溶液中添加亞硝酸或亞硝酸鹽而進行反應。添加較佳為慢慢進行以抑制急遽之發熱或發泡。
第二步驟之反應時之溫度並無特別限制,較佳為10~80℃,更佳為20~70℃,進一步較佳為30~60℃。第二步驟之反應係於成為2,5-二氰基-3,6-二胺基吡、鹵化劑及亞硝酸或亞硝酸鹽共存於一個反應系統內之狀態時,具體而言於添加結束時大致完成。若反應完成後亦保持於高溫度之狀態下,則有產物發生分解之情況。因此,較佳為於反應完成後,冷卻至室溫以下以抑制產物之分解。
本發明之化合物可用作發光材料。本發明之發光材料可提供有機光致發光元件、有機電致發光元件等發光元件。本發明之化合物由於具有輔助其他發光材料(主體(host)材料)之發光之功能,故而可摻雜於其他發光材料
使用。
本發明之有機光致發光元件係於基板上設置含有本發明之發光材料之發光層而成。發光層可藉由旋轉塗佈等之類之塗佈法、噴墨印刷法等之類之印刷法、蒸鍍法等而獲得。
本發明之有機電致發光元件係於陽極與陰極之間設置有機層而成。本發明中之「有機層」意指位於陽極與陰極之間之實質上由有機物所構成之層,該等層亦可於無損本發明之發光元件之性能之範圍內包含無機物。
作為本發明之有機電致發光元件之一實施形態中之結構,可列舉於基板上依序由陽極、電洞注入層、電洞傳輸層、電子阻擋層、發光層、電洞阻擋層、電子傳輸層、陰極所構成者,又,可列舉於電子傳輸層與陰極之間進一步具有電子注入層者。於該等多層結構中可將有機層省略若干層,例如亦可於基板上依序設為陽極、電洞傳輸層、發光層、電子傳輸層、電子注入層、陰極,或者設為陽極、電洞傳輸層、發光層、電子傳輸層、陰極。本發明之發光材料不僅可摻雜於發光層中,亦可摻雜於電洞注入層、電洞傳輸層、電子阻擋層、電洞阻擋層、電子傳輸層或電子注入層中。
基板係成為發光元件之支持體者,使用矽板、石英板、玻璃板、金屬板、金屬箔、樹脂膜、樹脂片材等。尤佳為玻璃板、或聚酯、聚甲基丙烯酸酯、聚碳酸酯、聚碸等透明之合成樹脂之板。於使用合成樹脂基板之情形時,必須注意阻氣性。若基板之阻氣性過低,則有發光元件因通過基板之外部氣體而劣化之情況。因此,較佳為於合成樹脂基板之任一單側或兩側設置緻密之矽氧化膜等而確保阻氣性。
於基板上設置有陽極。陽極一般使用功函數較大之材料。作為陽極用材料,例如可列舉:鋁、金、銀、鎳、鈀、鉑等金屬;銦氧化物、錫氧化物、ITO、氧化鋅、In2O3-ZnO、IGZO等金屬氧化物;碘化銅等鹵化金屬;碳
黑、或聚(3-甲基噻吩)、聚吡咯、聚苯胺等導電性高分子等。陽極之形成多數情況下通常係藉由濺鍍法、真空蒸鍍法等而進行。又,於銀等之金屬微粒子、碘化銅等之微粒子、碳黑、導電性之金屬氧化物微粒子、導電性高分子微粉末等之情形時,亦可藉由分散於適當之黏合劑樹脂溶液中並塗佈於基板上而形成陽極。進一步,於導電性高分子之情形時,亦可藉由電解聚合直接於基板上形成薄膜,或於基板上塗佈導電性高分子而形成陽極。
陽極亦可積層不同之2種以上之物質而形成。陽極之厚度根據所需之透明性而不同。於必需透明性之情形時,較理想為將可見光之透過率設為通常60%以上、較佳為80%以上,於此情形時,厚度通常為10~1000nm,較佳為10~200nm。於可為不透明之情形時,陽極可與基板之厚度為相同程度。陽極之薄片電阻較佳為數百Ω/□以上。
作為視需要設置之電洞注入層,除以銅酞青為代表之卟啉化合物以外,亦可使用萘二胺衍生物;星爆型之三苯基胺衍生物;分子中具有3個以上之三苯基胺結構且具有經單鍵或不包含雜原子之二價基連結之結構的芳基胺化合物等三苯基胺三聚物及四聚物;六氰基氮雜聯三伸苯之類之受體性之雜環化合物或塗佈型之高分子材料。該等材料除藉由蒸鍍法以外,亦可藉由旋轉塗佈法或噴墨法等公知之方法形成薄膜。
作為用於視需要設置之電洞傳輸層之電洞傳輸材料,較佳為自陽極之電洞注入效率高,且可高效率地傳輸注入之電洞。因此,較佳為離子化電位小,對可見光之光之透明性高,而且電洞遷移率大,進一步穩定性優異,不易於製造時或使用時產生成為阱(trap)之雜質。除上述一般要求以外,於考慮車載顯示用之應用之情形時,較佳為元件進一步耐熱性較高。因此,較理想為Tg具有70℃以上之值之材料。
作為視需要而設置之電洞傳輸層,可列舉:三唑衍生物、二唑衍生物、
咪唑衍生物、咔唑衍生物、吲哚并咔唑衍生物、聚芳基烷烴衍生物、吡唑啉衍生物、吡唑酮衍生物、苯二胺衍生物、芳基胺衍生物、胺基取代查耳酮衍生物、唑衍生物、苯乙烯基蒽衍生物、茀酮衍生物、腙衍生物、茋衍生物、矽氮烷衍生物、苯胺系共聚物、導電性高分子低聚物等。更具體而言,可列舉:含有間咔唑基苯基之化合物;N,N'-二苯基-N,N'-二(間甲苯基)-聯苯胺(以下,簡稱為TPD)、N,N'-二苯基-N,N'-二(α-萘基)-聯苯胺(以下,簡稱為NPD)、N,N,N',N'-四聯苯基聯苯胺等聯苯胺衍生物;1,1-雙[(二-4-甲苯基胺基)苯基]環己烷(以下,簡稱為TAPC);各種三苯基胺三聚物及四聚物或咔唑衍生物等。該等可單獨使用1種或者組合2種以上而使用。電洞傳輸層可為單層結構之膜,亦可為積層結構之膜。又,作為電洞之注入、傳輸層,可使用聚(3,4-乙二氧基噻吩)(以下,簡稱為PEDOT)/聚(苯乙烯磺酸鹽)(以下,簡稱為PSS)等塗佈型之高分子材料。該等材料除藉由蒸鍍法以外,亦可藉由旋轉塗佈法或噴墨法等公知之方法形成薄膜。
又,於電洞注入層或電洞傳輸層中可使用對上述層所通常使用之材料進一步P摻雜三溴苯基胺六氯銻而成者;或於其部分結構具有PD之結構之高分子化合物等。作為電洞注入、傳輸性之主體材料,可使用CBP或TCTA、mCP等咔唑衍生物等。
以下列舉可用作電洞注入材料之較佳之化合物(hi1)~(hi7)。
以下列舉可用作電洞傳輸材料之較佳之化合物(ht1)~(ht38)。
作為視需要設置之電子阻擋層,可使用4,4',4"-三(N-咔唑基)
三苯基胺(以下,簡稱為TCTA)、9,9-雙[4-(咔唑-9-基)苯基]茀、1,3-雙(咔唑-9-基)苯(以下,簡稱為mCP)、2,2-雙(4-咔唑-9-基苯基)金剛烷(以下,簡稱為Ad-Cz)等咔唑衍生物;以9-[4-(咔唑-9-基)苯基]-9-[4-(三苯基矽基)苯基]-9H-茀為代表之具有三苯基矽基及三芳基胺結構之化合物等具有電子阻擋作用之化合物。該等可單獨使用1種或者組合2種以上而使用。電子阻擋層可為單層結構之膜,亦可為積層結構之膜。該等材料除藉由蒸鍍法以外,亦可藉由旋轉塗佈法或噴墨法等公知之方法形成薄膜。
以下列舉可用作電子阻擋材料之較佳之化合物(es1)~(es5)。
發光層係具有藉由自陽極及陰極之各者注入之電洞及電子再結合而生成激子從而發光之功能的層。發光層可單獨藉由本發明之發光材料而形成,亦可對主體材料摻雜本發明之發光材料而形成。作為主體材料之例,可列舉:三(8-羥基喹啉)鋁(以下,簡稱為Alq3)等羥基喹啉衍生物之金屬錯合物、蒽衍生物、雙苯乙烯基苯衍生物、芘衍生物、唑衍生物、聚對苯乙炔衍生物、具有聯吡啶基及鄰聯三苯結構之化合物、mCP、噻唑衍生物、苯并咪唑
衍生物、聚二烷基茀衍生物等。於發光層中可包含公知之摻雜劑。作為摻雜劑,可列舉:喹吖酮、香豆素、紅螢烯、蒽、苝及該等之衍生物、苯并吡喃衍生物、玫瑰紅衍生物、胺基苯乙烯基衍生物等。又,亦可使用Ir(ppy)3等綠色之磷光發光體、FIrpic、FIr6等藍色之磷光發光體、Btp2Ir(acac)等紅色之磷光發光體等磷光性之發光體。該等可單獨使用1種或者組合2種以上而使用。發光層可為單層結構之膜,亦可為積層結構之膜。該等材料除藉由蒸鍍法以外,亦可藉由旋轉塗佈法或噴墨法等公知之方法形成薄膜。
於使用主體材料之情形時,關於發光層中可含有之本發明之發光材料之量,下限較佳為0.1質量%,更佳為1質量%,上限較佳為50質量%,更佳為20質量%,進一步較佳為10質量%。
以下列舉可用作發光層之主體材料之較佳之化合物(el1)~(el40)。
作為視需要設置之電洞阻擋層,可列舉:具有聯吡啶基及鄰聯三
苯結構之化合物、2,9-二甲基-4,7-聯苯-1,10-啡啉(以下,簡稱為BCP)等啡啉衍生物、或雙(2-甲基-8-喹啉)-4-苯基苯酚鋁(III)(以下,簡稱為BAlq)等羥基喹啉衍生物之金屬錯合物、各種稀土類錯合物、唑衍生物、三唑衍生物、三衍生物等具有電洞阻擋作用之化合物。該等材料可兼作電子傳輸層之材料。該等可單獨使用1種或者組合2種以上而使用。電洞阻擋層可為單層結構之膜,亦可為積層結構之膜。該等材料除藉由蒸鍍法以外,亦可藉由旋轉塗佈法或噴墨法等公知之方法形成薄膜。
以下列舉可用作電洞阻擋材料之較佳之化合物(hs1)~(hs11)。
作為視需要設置之電子傳輸層,除以Alq3、BAlq為代表之羥基喹啉衍生物之金屬錯合物以外,可使用各種金屬錯合物、三唑衍生物、三衍生物、二唑衍生物、噻二唑衍生物、碳二醯亞胺衍生物、喹啉衍生物、啡啉衍生物、噻咯衍生物等。該等可單獨使用1種或者組合2種以上而使用。電子傳輸層可為單層結構之膜,亦可為積層結構之膜。該等材料除藉由蒸鍍法以外,亦可藉由旋轉塗佈法或噴墨法等公知之方法形成薄膜。
作為視需要設置之電子注入層,可使用氟化鋰、氟化銫等鹼金屬鹽、氟化鎂等鹼土金屬鹽、氧化鋁等金屬氧化物等,於電子傳輸層及陰極之較佳之選擇中,可省略電子注入層。
於電子注入層或電子傳輸層中,可使用對通常用於上述層之材料進一步N摻雜銫等金屬而成者。
以下列舉可用作電子傳輸材料之較佳之化合物(et1)~(et30)。
以下列舉可用作電子注入材料之較佳之化合物(ei1)~(ei4)。
以下列舉可用作穩定化材料之較佳之化合物(st1)~(st5)。
陰極一般使用功函數較小之材料。作為陰極用材料,例如使用鈉、鈉-鉀合金、鋰、錫、鎂、鎂/銅混合物、鎂/鋁混合物、鎂/銦混合物、鋁/氧化鋁混合物、銦、鈣、鋁、銀、鋰/鋁混合物、鎂銀合金、鎂銦合金、鋁鎂合金等。藉由使用透明導電性材料,可獲得透明或半透明之陰極。陰極之厚度通常為10~5000nm,較佳為50~200nm。陰極之薄片電阻較佳為數百Ω/□以上。
若基於保護由低功函數金屬所構成之陰極之目的,於其上進一步積層鋁、銀、鎳、鉻、金、鉑等功函數高且相對於大氣較為穩定之金屬層,則增加元件之穩定性,故而較佳。又,為了提昇陰極與鄰接之有機層(例如電子傳輸層或電子注入層)之接觸,可於兩者之間設置陰極界面層。作為用於陰極界面層之材料,可列舉:芳香族二胺化合物、喹吖酮化合物、稠四苯衍生物、有機矽化合物、有機磷化合物、具有N-苯基咔唑骨架之化合物、N-乙烯基咔唑聚合物等。
本發明之發光元件可應用於單一之元件、由陣列狀地配置之結構所構成之元件、陽極與陰極呈X-Y矩陣狀地配置而成之結構之任一者。
以下,對本發明之實施形態示出其效果。
使用本發明之發光材料,製作有機光致發光元件及有機電致發光元件,評價發光特性。
發光特性之評價係使用電源電錶(SourceMeter)(吉時利公司製造:2400系列)、半導體參數分析器(安捷倫科技公司製造:E5273A)、光功率計測定裝置(Newport公司製造:1930C)、光學分光器(Ocean Optics公司製造:USB2000)、分光放射計(Topcon公司製造:SR-3)及高速掃描攝影機(濱松光子學公司製造:C4334型)而進行。
其次,示出實施例而更具體地說明本發明。本發明並不受該等實施例限制。於不脫離本發明之宗旨之範圍內,可進行構成之附加、省略、置換及其他變更。
於氬環境之手套箱中製備Ac-CNP之甲苯溶液A(濃度10-4莫耳/l)。
使用Ac-CNP作為蒸鍍源,於真空度10-4Pa以下之條件下,蒸鍍於石英基板上,獲得具有厚度100nm之薄膜之有機光致發光元件B。
分別使用Ac-CNP及mCBP作為蒸鍍源,於10-4Pa以下之條件下,蒸鍍於石英基板上,獲得具有Ac-CNP濃度6.0重量%且厚度100nm之薄膜之有機光致發光元件C。
對甲苯溶液A、有機光致發光元件B及有機光致發光元件C測定由310nm激發光所產生之發射光譜及吸收光譜。將結果示於圖1。
關於光致發光量子效率,經過氮起泡之甲苯溶液A為20.4%,未經過氮起泡之甲苯溶液A為9.3%,有機光致發光元件C為67.4%。
將有機光致發光元件C之5K、50K、100K、150K、200K、250K及300K
下之暫態衰減曲線示於圖2。該暫態衰減曲線於初期觀察到直線性成分(螢光成分),但於數μ秒以後觀察到自直線性偏離之成分(延遲成分)。根據該結果可知,Ac-CNP係除螢光成分以外亦包含延遲成分之發光體(τprompt=45奈秒,τdelayed=71微秒)。又,可知延遲成分之壽命因溫度而有變化,故而Ac-CNP為熱活性型延遲螢光材料(TADF)。
於形成有膜壓110nm之由銦錫氧化物(ITO)所構成之陽極之玻璃基板上依序藉由真空蒸鍍法(5.0×10-4Pa以下)積層厚度40nm之電洞傳輸層、厚度10nm之電子阻擋層、厚度20nm之發光層、厚度10nm之電洞阻擋層及厚度30nm之電子傳輸層(參照圖3)。
使用α-NPD作為電洞傳輸層之材料。
使用mCP作為電子阻擋層之材料。
使用mCBP作為發光層之主體材料。
使用Ac-CNP作為發光層之摻雜材料。將Ac-CNP濃度設定為6.0重量%。
使用PPF作為電洞阻擋層之材料。
使用TPBi作為電子傳輸層之材料。
繼而,藉由依序利用真空蒸鍍法積層厚度0.8nm之氟化鋰膜及厚度80nm之
鋁膜而形成陰極,獲得有機電致發光元件。
測定有機電致發光元件之特性。於圖4中表示發射光譜。發射光譜處於約500nm~約700nm之範圍。於圖5中表示電壓-電流密度-發光強度特性。朝左之箭頭所示之資料表示電壓-電流密度特性,朝右之箭頭所示之資料表示電壓-發光強度特性。於圖6中表示電流密度-外部量子效率特性。最大外部量子效率為13.3%。由於使用螢光材料之有機電致發光元件之外部量子效率之理論極限值為5~7.5%,故而使用Ac-CNP而獲得之本發明之有機電致發光元件實現超過理論極限值的高外部量子效率。
使用Px-CNP代替Ac-CNP,除此以外,藉由與實施例1相同之方法進行特性評價。甲苯溶液無法觀察到可見光範圍之發光。關於光致發光量子效率,有機光致發光元件C為15.1%。根據暫態衰減曲線可知,Px-CNP係除螢光成分以外亦包含延遲成分之發光體(τprompt=21奈秒,τdelayed=1.5微秒)(參照圖7)。又,可知延遲成分之壽命因溫度而有變化,故而Px-CNP為熱活性型延遲螢光材料(TADF)。
測定有機電致發光元件(圖8)之特性。於圖9中表示發射光譜。與實施例1同樣地,發射光譜處於約500nm~約700nm之範圍。於圖10中表示電壓-電流密度-發光強度特性。朝左之箭頭所示之資料表示電壓-電流密度特性,朝右之箭頭所示之資料表示電壓-發光強度特性。於圖11中表示電流密度-外部量子效率特性。最大外部量子效率為3.0%。
使用BCz-CNP代替Ac-CNP,除此以外,藉由與實施例1相同之方法進行特性評價。關於光致發光量子效率,經過氮起泡之甲苯溶液A為15.6%,未經過氮起泡之甲苯溶液A為10.8%,有機光致發光元件C為54.7%。根據暫態衰減曲線可知,BCz-CNP係除螢光成分以外亦包含延遲成分之發光體(τprompt=35奈秒,τdelayed=135微秒)(參照圖12)。又,可知延遲成分之壽命因溫度而有變化,故而BCz-CNP為熱活性型延遲螢光材料(TADF)。
測定有機電致發光元件(圖13)之特性。與實施例1同樣地,發射光譜處於約500nm~約700nm之範圍。最大外部量子效率為11.9%。
使用PCz-DCP作為蒸鍍源,於真空度10-4Pa以下之條件下,蒸鍍於石英基板上,獲得具有厚度100nm之薄膜之有機光致發光元件B。
分別使用PCz-DCP及CBP作為蒸鍍源,於10-4Pa以下之條件下蒸鍍於石英
基板上,獲得具有PCz-DCP濃度6.0重量%且厚度100nm之薄膜之有機光致發光元件C。
對有機光致發光元件B及有機光致發光元件C測定由310nm激發光所產生之發射光譜及吸收光譜。將結果示於圖14。
關於光致發光量子效率,有機光致發光元件C為36.5%。
將有機光致發光元件C之5K、50K、100K、150K、200K、250K及300K下之暫態衰減曲線示於圖15。該暫態衰減曲線於初期觀察到直線性成分(螢光成分),但於數μ秒以後觀察到自直線性偏離之成分(延遲成分)。根據該結果可知,PCz-DCP係除螢光成分以外亦包含延遲成分之發光體(τprompt=28奈秒,τdelayed=147微秒)。又,可知延遲成分之壽命因溫度而有變化,故而PCz-DCP為熱活性型延遲螢光材料(TADF)。
於形成有膜壓110nm之由銦錫氧化物(ITO)所構成之陽極之玻璃基板上依序藉由真空蒸鍍法(5.0×10-4Pa以下)積層厚度35nm之電洞傳輸層、厚度15nm之發光層、厚度10nm之電洞阻擋層及厚度40nm之電子傳輸層。
使用TAPC作為電洞傳輸層之材料。
使用CBP作為發光層之主體材料。
使用PCz-DCP作為發光層之摻雜材料。將PCz-DCP濃度設定為6.0重量%。
使用PPF作為電洞阻擋層之材料。
使用B3PyPB作為電子傳輸層之材料。
繼而,藉由依序利用真空蒸鍍法積層厚度0.8nm之氟化鋰膜及厚度80nm之鋁膜而形成陰極,獲得有機電致發光元件(器件B)(參照圖16)。
測定有機電致發光元件(器件B)之特性。於圖18中表示發射光譜。與實施例1同樣地,發射光譜處於約500nm~約700nm之範圍。於圖19中表示電壓-電流密度-發光強度特性。朝左之箭頭所示之資料表示電壓-電流密度特性,朝右之箭頭所示之資料表示電壓-發光強度特性。於圖20中表示電流密度-外部量子效率特性。最大外部量子效率為7.8%。
使用26mCPy代替CBP,除此以外,藉由與實施例4相同之方法獲得有機電致發光元件(器件A)(參照圖17)。
測定有機電致發光元件(器件A)之特性。於圖18中表示發射光譜。與實施例1同樣地,發射光譜處於約500nm~約700nm之範圍。於圖19中表示電壓-電流密度-發光強度特性。朝左之箭頭所示之資料表示電壓-電流密度特性,朝右之箭頭所示之資料表示電壓-發光強度特性。於圖20中表示電流密度-外部量子效率特性。最大外部量子效率為6.4%。
使用PAc-DCP代替PCz-DCP,除此以外,藉由與實施例4相同之方法進行特性評價。甲苯溶液無法觀察到可見光範圍之發光。關於光致發光量子效率,有機光致發光元件C為31.9%。根據暫態衰減曲線可知,PAc-DCP係除螢光成分以外亦包含延遲成分之發光體(τprompt=19奈秒,τdelayed=2.6微秒)(圖21)。又,可知延遲成分之壽命因溫度而有變化,故而PAc-DCP為熱活性型延遲螢光材料(TADF)。
測定有機電致發光元件(器件B:圖22)之特性。於圖24中表示發射光譜。與實施例1同樣地,發射光譜處於約500nm~約700nm之範圍。於圖25中表示電壓-電流密度-發光強度特性。朝左之箭頭所示之資料表示電壓-電流密度特性,朝右之箭頭所示之資料表示電壓-發光強度特性。於圖26中表示電流密度-外部量子效率特性。最大外部量子效率為6.9%。
使用α-NPD代替TAPC,使用26mCPy代替CBP,且使用TPBi代替B3PyPB,除此以外,藉由與實施例6相同之方法獲得有機電致發光元件(器件A)(參照圖23)。
測定有機電致發光元件(器件A)之特性。於圖24中表示發射光譜。與實施例1同樣地,發射光譜處於約500nm~約700nm之範圍。於圖25中表示電壓-電流密度-發光強度特性。朝左之箭頭所示之資料表示電壓-電流密度特性,朝右之箭頭所示之資料表示電壓-發光強度特性。於圖26中表示電流密度-外部量子效率特性。最大外部量子效率為2.4%。
合成中心骨架具有2,3-二氰基吡之化合物(式(I)表示之化合物)而獲得之發光材料於基於TADF之評價中,獲得高EL發光特性。又,可實現遠遠高於通常之螢光分子之外部量子效率(EQE)之理論極限值(5%)的EQE值。式(I)表示之化合物係極為有望作為TADF發光材料之材料。
合成中心骨架具有2,5-二氰基吡之式(II)表示之化合物而獲得之發光材料於基於TADF之評價中,獲得高EL發光特性。又,可實現高於通常之螢光分子之外部量子效率(EQE)之理論極限值(5%)之EQE值。式(II)表示之化合物係有望作為TADF發光材料之材料。
參考例
將(2E)-2,3-二胺基-3-(苯硫基)丙烯腈400mg溶解於1,2-二甲氧基乙烷45ml中,將所獲得之溶液加入至含0.1M檸檬酸-檸檬酸鈉緩衝液(pH=3.0)150ml及水150ml之溶液中並於室溫下放置5小時。對析出之紅色針狀結晶進行過濾並藉由正己烷-乙酸乙酯(3:1)3ml進行清洗。獲得3,6-二胺基-2,5-二氰基吡7.5mg(產率4.5%)。
13C-NMR(d6-DMSO):149.730,115.115,113.251ppm
使溴化銅(II)23.73g(106.2毫莫耳)及亞硝酸三級丁酯10.95g(118.0毫莫耳)溶解於乾燥乙腈100ml中。於所獲得之溶液中,於60℃慢慢添加3,6-二胺基-2,5-二氰基吡3.40g(21.2毫莫耳)。於添加3,6-二胺基-2,5-二氰基吡時發泡。添加結束後,於70℃攪拌5小時使該等反應(反應率69.1%)。將反應液冷卻至室溫,注入至水中,繼而藉由氯仿萃取3次,分液為有機相及水相。藉由水清洗有機相,繼而藉由無水硫酸鈉進行脫水,進一步進行過濾及濃縮。藉由矽膠層析法對粗產物進行精製,於真空下使之乾燥,獲得2,5-二氰基-3,6-二溴吡(4.1g、產率67.0莫耳%)。
13C-NMR(125MHz、CDCl3):δ 140.78,134.25,112.62.MS:m/z 287.01[M]+
於3,6-二胺基-2,5-二氰基吡40.0g(217.4毫莫耳)中添加乙腈(水含量:約250ppm)522ml並進行攪拌而獲得均勻之溶液。於該溶液中加入溴化銅(II)145.7g(652.3毫莫耳)。繼而,將溶液維持為40℃,歷時90分鐘滴加純度90%之亞硝酸三級丁酯87.20g(101ml、761.0毫莫耳)。滴加結束後,於40℃攪拌30分鐘使該等反應(反應率(Gross Yield)80.1%)。過濾40℃之反應液而去除不溶物。將濾液注入至水中並於10℃使固形物成分析出,繼而進行過濾。於40℃使固形物成分溶解於甲苯中。將所獲得之溶液進行過濾而去除不溶
物。於55℃減壓下濃縮濾液。於25℃於濃縮液中滴加正己烷,滴加結束後,冷卻至10℃,進行過濾。使濾布上之淡黃色固形物乾燥,獲得2,5-二氰基-3,6-二溴吡45.34g(產率(Net Yield)70.3莫耳%、純度97%)。
於3,6-二胺基-2,5-二氰基吡2.25g(14.1毫莫耳)中添加乾燥乙腈68ml並進行攪拌而獲得均勻之溶液。於該溶液中加入溴化銅(II)15.53g(69.5毫莫耳)。繼而,將溶液維持為40℃,歷時40分鐘滴加純度90%之亞硝酸三級丁酯8.00g(9.2ml,69.8毫莫耳)與乾燥乙腈9.2ml之混合液。滴加結束後,於40℃攪拌4小時使該等反應(反應率(Gross Yield)79.4%)。將40℃之反應液進行過濾而去除不溶物。將濾液注入至水中並於10℃使固形物成分析出,繼而進行過濾。於40℃使固形物成分溶解於氯仿中。將所獲得之溶液進行過濾而去除不溶物。於40℃減壓下濃縮濾液。於25℃於濃縮液中滴加正己烷,滴加結束後,冷卻至10℃,進行過濾。使濾布上之淡黃色固形物乾燥,獲得2,5-二氰基-3,6-二溴吡2.97g(產率(Net Yield)72莫耳%、純度98%)。
於3,6-二胺基-2,5-二氰基吡2.0g(12.5毫莫耳)中添加乾燥乙腈60ml並進行攪拌而獲得均勻之溶液。於該溶液中加入溴化銅(II)13.96g(62.5毫莫耳)。繼而,將溶液維持為40℃,歷時85分鐘滴加純度90%之亞硝酸正丁酯7.21g(8.1ml,62.9毫莫耳)與乾燥乙腈8.1ml之混合液。滴加結束後,於40℃攪拌2小時使該等反應(反應率(Gross Yield)79.2%)。將40℃之反應液進行過濾而去除不溶物。將濾液注入至水中並於10℃使固形物成分析出,繼而進行過濾。於40℃使固形物成分溶解於氯仿中。將所獲得之溶液進行過濾而去除不溶物。於40℃減壓下濃縮濾液。於25℃於濃縮液中滴加正己烷,滴加結束後,冷卻至10℃,進行過濾。使濾布上之淡黃色固形物乾燥,獲得2,5-二氰基
-3,6-二溴吡2.66g(產率(Net Yield)69.9莫耳%、純度94.6%)。
將純度90%之亞硝酸正丁酯7.21g與乾燥乙腈8.1ml之混合液變更為純度95%之亞硝酸異丁酯6.79g(7.8ml)與乾燥乙腈7.8ml之混合液,除此以外,藉由與實施例11相同之方法獲得2,5-二氰基-3,6-二溴吡。反應率為79.5%,產率為70.0莫耳%,純度為95.4%。
將純度90%之亞硝酸正丁酯7.21g與乾燥乙腈8.1ml之混合液變更為純度95%之亞硝酸異戊酯7.74g(8.8ml)與乾燥乙腈8.8ml之混合液,將滴加時間變更為90分鐘,除此以外,藉由與實施例11相同之方法獲得2,5-二氰基-3,6-二溴吡。反應率為78.8%,產率為69.6莫耳%,純度為95.3%。
將3,6-二胺基-2,5-二氰基吡之量變更為2.0g,將溴化銅(II)之量變更為13.96g,將乙腈之量變更為60ml,將純度90%之亞硝酸三級丁酯之量變更為7.13g,將反應時之溫度變更為30℃,將滴加時間變更為30分鐘,將滴加結束後之攪拌變更為4小時,除此以外,藉由與實施例9相同之方法獲得2,5-二氰基-3,6-二溴吡。反應率為76.4%。
將3,6-二胺基-2,5-二氰基吡之量變更為2.0g,將溴化銅(II)之量變更為13.98g,將乙腈之量變更為60ml,將純度90%之亞硝酸三級丁酯之量變更為7.13g,將反應時之溫度變更為60℃,將滴加時間變更為20分鐘,將滴加結束後之攪拌變更為3小時,除此以外,藉由與實施例9相同之方法獲得2,5-二氰基-3,6-二溴吡。反應率為76.3%。
將3,6-二胺基-2,5-二氰基吡之量變更為2.0g,將溴化銅(II)之量變更為13.96g,將乙腈之量變更為60ml,將純度90%之亞硝酸三級丁酯之量變更為7.22g,將滴加結束後之攪拌變更為3小時,除此以外,藉由與實施例9相同之方法獲得2,5-二氰基-3,6-二溴吡。反應率為72.4%。
將3,6-二胺基-2,5-二氰基吡之量變更為2.0g,將溴化銅(II)之量變更為13.96g,將乙腈之量變更為60ml,將純度90%之亞硝酸三級丁酯之量變更為7.22g,不進行滴加結束後之攪拌,除此以外,藉由與實施例9相同之方法獲得2,5-二氰基-3,6-二溴吡。反應率為77.8%。
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