TWI507407B - A hardened composition, a hardened product, and an organic electric field light-emitting element using the same - Google Patents
A hardened composition, a hardened product, and an organic electric field light-emitting element using the same Download PDFInfo
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- TWI507407B TWI507407B TW101102242A TW101102242A TWI507407B TW I507407 B TWI507407 B TW I507407B TW 101102242 A TW101102242 A TW 101102242A TW 101102242 A TW101102242 A TW 101102242A TW I507407 B TWI507407 B TW I507407B
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/26—Nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/32—Monomers containing only one unsaturated aliphatic radical containing two or more rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/34—Monomers containing two or more unsaturated aliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/26—Di-epoxy compounds heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
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Description
本發明係含有兩個聚合性基之吲哚并咔唑(indolocarbazole)骨架化合物的硬化性組成物、硬化物、及使用其之有機電場發光元件。
通常電場發光元件中係有在發光元件中使用無機化合物之無機電場發光元件、與使用有機化合物之有機電場發光元件者,近年來由於用低電壓並且可得高亮度發光之特徵,所以被積極地進行有機電場發光元件之實用化研究。
有機電場發光元件之構造係基本上在蒸著有銦-錫氧化物(ITO)等陽極材料薄膜的玻璃基板上,形成正孔注入層,再形成發光層等有機薄膜層,再於其上形成陰極材料之薄膜予以作成者做為其基本者,並在此基本構造上有適當地設置電洞(positive hole)輸送層或電子輸送層所成之元件者。有機電場發光元件之層構成係例如陽極/電洞注入層/發光層/電子輸送層/陰極、或陽極/電洞注入層/電洞輸送層/發光層/電子輸送層/陰極等者。
近年已獲知藉由在發光層與陽極之間,組合入電洞注入層及電洞輸送層等電荷輸送層時可以改善對發光層之電洞注入性,使其成為電荷之平衡性更為適當化之緩衡層予以作用。可以顯著地改善元件之發光效率或壽命之事已被獲知。
有機電場發光元件之電洞輸送層所用電洞輸送材料中係較大地分類時可以有低分子系電洞輸送材料與高分子系電洞輸送材料。
做為使用低分子系電洞輸送材料的電洞輸送層之製膜方法,主要係用真空噴鍍法,其特徵係在於可以極容易使具有不同功能之各種材料成多層化,可以形成為高性能之有機電場發光元件,可是相反地會造成配電盤成大畫面,很難經由高精細化而控制膜厚之均勻性或很難分別塗刷,甚至還須要大規模之真空裝置而提高其製造成本,成為其問題所在。
又,使用低分子系電洞輸送材料的電洞輸送層之製膜方法,針對藉由低分子系電洞輸送材料的溶液塗佈之製膜法亦曾被付予實用化之研究,惟這種手法中還被觀察到經由低分子化合物之結晶化被觀察到會有偏析或相分離,要實用化必須要加以改善。
另一方面做為高分子系電洞輸送材料之製膜方法,由於大多為無法以真空蒸著法無法蒸著之材料,所以通常使用自旋塗層法,印刷法或油墨噴射法等之溶液塗佈法。此等方法較容易大畫面化,易於量產化,但其反面卻很容易發生層面之混合,無法經由積層以分離其功能,更加上必須有對溶劑之溶解性等乾式不相同之特性,被限制成可使用於濕式法之電荷注入材料,電荷輸送材料而成為其問題所在。
為了要試予發現此等要求特性,例如專利文獻1雖報
告使用丙烯化合物或其硬化物,專利文獻2係報告使用具有乙烯基之NPD的硬化物,但使用此等化合物之有機電場發光元件雖然藉由積層可以造成機能分離,但其電子耐性或電荷輸送性能並無法充分達成,以得到充分之特性。
又,做為提高有機電場發光元件之發光效率的手法,還有在π共軛高分子之主鍵中組合電子耐性或電荷輸送性能優異之吲哚并咔唑單位的高分子材料,以及發光元件被揭示。即專利文獻3中係揭示在吲哚并咔唑之6,12單位結合之共軛系高分子,又專利文獻4中係揭示以N位取代之吲哚并咔唑做為主架構之共軛系高分子。惟此等高分子雖可具有較佳之電子耐性或電荷輸送性,但主鏈中含有以吲哚并咔唑骨架之π共軛高分子係對於有機溶劑之溶解性低,很難成膜,即使可以成膜,亦與其他可以塗佈之高分子一樣,薄膜本身不具有溶劑耐性,所以有無法將成膜後發光層材料等其他材料塗佈於上層予以成膜的問題存在。
先行技術文獻
[專利文獻1]日本特開2009-16739號公報
[專利文獻2]日本特開2009-252944號公報
[專利文獻3]日本特開2004-204234號公報
[專利文獻4]日本特開2006-183048號公報
欲以溶液塗佈法作成具有高性能之有機電場發光元件時,必須形成具高度電子耐性或電荷輸送性能,且不溶於
溶劑之有機薄膜層。
本發明係有鑑於上述課題而得以完成者,以提供含有高發光效率且可適用於濕式作業之有機電場發光元件用之具有二個聚合性基的吲哚并咔唑骨架化合物之硬化性組成物及其硬化物為目的者。又,本發明係以提供被使用於照明裝置、畫像顯示裝置、顯示裝置用背光等所用之上述硬化性組成物或使用該硬化物之有機電場發光元件為目的者。
為達成上述目的,本發明人係經過銳意檢討之結果,發現可以用含具有二個聚合性基之吲哚并咔唑骨架化合物的硬化性組成物及硬化物時,可以在上層塗佈含有其他材料之有機層即可以層合,且可以提高發光性能,遂而完成本發明者。
本發明係有關在含有具2個聚合性基之吲哚并咔唑骨架化合物做為特徵之硬化性組成物,硬化物及基板上所積層之陽極層與陰極層之間具備有機層之有機電場發光元件中,該有機層中的至少一層為含有該硬化性組成物或硬化物之層的有機電場發光元件者。
本發明係有關使一般式(1)所示之化合物及以一般式(2)所示之化合物的總莫耳數為100時,一般式(1)所示之化合物為含有5~100莫耳%、一般式(2)所示化合物為含有0~95莫耳%所成硬化性組成物者。
在此,環A係表示與鄰接環在任意位置縮合之式(1a)所示雜環,R係氫原子、C1~C20之烷基、C1~C20之烷氧基、C6~C30之芳基、C6~C30之芳氧基、C7~C36之芳基烷基、C7~C36之芳基烷氧基、C3~C30之雜芳基、C3~C30之雜芳氧基、C4~C36之雜芳烷基、C4~C36雜芳基烷氧基或C3~C30之環烷基,可為相同者亦可為不相同。Y1係示單結合、或二價之基,可相同亦可為不同者。可示C1~C20之烯烴基、C6~C30之丙炔基、C3~C30之雜丙炔基、CO、COO或O,可為相同亦可不相同。W1係聚合性基,可相同亦可不相同。
【化2】Z-Y2-W2(2)
在此Z係C6~C30之芳基、C3~C30之雜芳基、或C12~C60之二芳基胺基。Y2係示單結合、或二價之基。W2係聚合性基。又,Z、R、Y1、Y2係不具有5環以上之縮合環構造者。
做為一般式(1)所示化合物之較佳例,可為以下式(3)或(4)所示化合物。
式(3)或(4)中,Y1、W1係與一般式(1)相同意思,R1係與式(1)之R為相同意者。
上述一般式(2)之Z係以至少在其內部具有一個以下式(9)、(10)或(11)所示基較宜。
式(9)中、Ar1、Ar2係獨立地示C6~C30之芳基、C3~C30之雜芳基,亦可以Ar1、Ar2與N形成為縮合環。但Ar1、Ar2係不會具有5環以上之縮合環構造者。
式(10)、(11)中、R2係氫原子、C1~C20之烷基、C1~C20之烷氧基、C6~C30之芳基、C6~C30之芳氧基、C7~C36之芳基烷基、C7~C36之芳基烷氧基、C3~C30之雜芳基、C3~C30之雜芳氧基、C4~C36之雜芳烷基、C4~C36之雜芳基烷氧基或C3~C30之環烷基,可為相同亦可為不相同。但R2係不具有5環以上之縮合環構造者。
上述一般式(1)、(1a)及(2)中聚合性基W1、W2係為自由基聚合性基或陽離子聚合性基較為適宜。又,聚合性基W1、W2係以獨立地為自乙烯基,以碳數1~6之烷基所取代之乙烯基、環氧基、氧雜環丁烷基所選出之至少一個基為宜。
以一般式(1)、(1a)及(2)中W1、W2為選自乙烯基及自取代之乙烯基所選出之乙烯基類、式(1)所示化合物為具有二個乙烯基類,一般式(2)所示化合物為具有一個乙烯基類為最佳。
另外,本發明又為聚合上述硬化性組成物使其硬化之硬化物。上述硬化性硬化物亦可為單獨含有式(1)所示化合物者,亦可為含有一般式(1)所示化合物,與一般式(2)所示化合物之兩者所成者。然後,聚合此硬化性組成物使其硬化所成之硬化物係可為一般式(1)所示化合物之單獨聚合物,亦可為與一般式(2)所示化合物所成之共聚合物。
本發明係有關在被層合於基板上之陽極層及陰極層間具備有機層之有機電場發光元件,在該有機層之至少一層含有上述硬化物為特徵之有機電場發光元件者。做為含上述硬化物之有機層可為電洞輸送層。
以下就本發明之實施形態詳細說明。
本發明之硬化性組成物及其硬化物係具有優異之電荷輸送能力,尤其含有可賦予電洞輸送能力的兩個聚合性基
之吲哚并咔唑骨架者。
本發明之硬化性組成物係含有上述一般式(1)所示之具有2個聚合性基之吲哚并咔唑骨架化合物者。
吲哚并咔唑骨架係自吲哚環與咔唑環縮合後之五環縮合環化合物的二個N位之H除去2個所產生者。此骨架係因複數地存在有可以與吲哚環與咔唑環縮合之位置,所以2個N位取代基若為不同時,是可以採用以下式(A)~(F)之六種類構造異構物之基,惟其任一之構造異性體亦可。另外,二個N位之取代基若為相同時,(C)與(F)會變成相同構造,異構物會成為具有五種存在。吲哚并咔唑骨架係在不抑制本發明之效果範圍內,可以具有取代基者。
上述一般式(1)中環A係表示與鄰接環在任意位置縮合之以上述式(1a)所示之雜環。惟式(1a)中之環係在包含N之邊無法縮合,所以會成為如上述式(A)~(F)之任一構造。
上述一般式(1)中,R係氫原子、C1~C20之烷基、C1~C20之烷氧基、C6~C30之芳基、C6~C30之芳氧基、C7~C36之芳基烷基、C7~C36之芳基烷氧基、C3~C30之雜芳基、C3~C30之雜芳氧基、C4~C36之雜芳烷基、C4~C36雜芳基烷氧基或C3~C30之環烷基、可為相同亦可為不相同。較佳係氫原子C1~C20之烷基、C1~C20之烷氧基、C6~C30芳基、C3~C30之雜芳基或C3~C30之環烷基,更佳係氫原子、C1~C8之烷基、C1~C8之烷氧基、C6~C18之芳基、C3~C18雜芳基或C3~C12之環烷基。此等基係在對於性能不至於有不佳之影響的範圍,還可以具有取代基。惟R係不會具有5環以上之縮合環構造者。
烷基之具體例可為甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、較佳係甲基、乙基、丙基、丁基、戊基、己基、庚基或辛基等碳數1~8之烷基。上述烷基鏈可為直鏈,亦可被分支者。
烷氧基之具體例可為甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、庚氧基、辛氧基、壬氧基、癸氧基、較佳係甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、庚氧基或辛氧基等碳數1~8之烷氧基。上述烷基鏈可為直鏈,亦可被分支者。
芳基、雜芳基之具體例可為苯、戊搭烯、茚、萘、
蒽、庚搭烯、辛搭烯、苯并二烯、萘茚嵌戊烯、吩哪烯、醋蒽烯、萞、toninden、1,2-苯并苊、醋菲烯、醋蒽烯、三鄰亞苯、嵌二萘、1,2-苯并菲、丁芬、丁省、七曜烯、二萘品苯、芘、戊芬、戊省、四鄰亞苯、膽蒽、螺烯(Helicen)、己芬、玉紅省、暈苯、十環烯、庚酚、吡蒽、卯苯、collanulen、fluminen、二苯并芘、雪松烯、特麗綸、稠四苯基騈稠四苯、三亞蘊、呋喃、苯并呋喃、異苯開呋喃、呫噸、oxatoren、二苯并呋喃、迫騈、噻吩、噻噸、噻蒽、吩噻噁、硫茚、異硫茚、硫塑料、硫戊環、二苯并噻吩、吡咯、吡唑、tellurazole、硒唑、噻唑、異噻唑、噁唑、呋咱、吡啶、吡嗪、嘧啶、噠嗪、三嗪、吲哚嗪、吲哚、異吲哚、吲唑、嘌呤、噻嗪、異喹啉、咔唑、isodoeo咔唑、咪唑、萘錠、酞嗪、喹唑啉、苯二吖庚因、喹喔啉、噌啉、喹啉、蝶啶、菲啶、吖啶、啶、菲繞啉、吩嗪、咔啉、苯氧碲、吩硒嗪、吩噻嗪、吩噁嗪、抗賴氨酸、thebenizin、唑叨啉、喹嚀叨啉、Acrindorin、二苯基酞、三苯并噻嗪、三苯井二噁嗪、菲嗪、蒽吖嗪、苯并噻唑、苯并咪唑、苯並噁唑、苯并異噁唑、苯并異噻唑或此等芳香環為自被複數結合之芳香族化合物中除去氫所產生之基。
另外,若芳香環為自複數結合之芳香族化合物所生成之基時,所連結之數以2~10為宜,更佳係2~7,所連結之芳香環可為相同,亦可為不同。這時結合種之位置並不被限定,可為所連結之芳香環末端部的環,亦可為中央部
之環。在此,芳香環係指芳香族碳化氫環及芳香族雜環的總稱而言者。又,所連結之芳香環若含有至少一個雜環時係包含雜芳基者。
在此,若芳香環為自複數所連結之芳香族化合物除去氫所生成之一價基係例如以下式所示者。
(式(12)~(14)中,Ar3~Ar8係示取代或不取代之芳香環)。
芳烷基、雜芳烷基之具體例可為上述芳基、雜芳基中有上述烷基連結之基。
芳氧基、芳烷氧基、雜芳氧基、雜芳基烷氧基之具體例可為上述芳基、芳烷基、雜芳基、雜芳烷基中連結有氧基之基。
環烷基之具體例可為環丙基、環丁基、環戊基、環己基、環庚基、環辛基、或甲基環己基,較佳係環戊基、環
己基或甲基環己基。
上述一般式(1)及(2)中,Y1、Y2係表示單結合、或二價之基,可相同亦可不相同。二價之基係以-(Z2)m-(X)n-(Z3)p-(X)q-所示之基,在此Z2、Z3係烯基、丙炔或異丙炔,X係O、COO、S、CONH、CO等,m、n、p、q係0~3之數。較佳Z2、Z3係C1~C20之伸烷基、C6~C30之丙炔基、C3~C30之異丙炔基,X係CO、COO或O。Y1、Y2係較佳為單結合,C1~C6之伸烷基、C6~C12之丙炔基、C3~C12之異丙炔基、CO、COO或O。但Y1、Y2係不會具有5環以上之縮合環構造者。
伸烷基之具體例有亞甲基、乙撑、亞丙基、丁撑、戊撑、己烯基、庚烯基、辛烯基、壬烯基、癸烯基、較佳係亞甲基、乙撑、亞丙基、丁撑、戊撑、己烯基、庚烯基、辛烯基等碳數1~8之伸烷基。上述伸烷基鏈係可為直鏈者,亦可為分支者。
丙炔基、異丙炔基之具體例可為自上述R之芳基、雜芳基所例之芳香環或此等芳香環為被複數連結之芳香族化合物中予以除去2個氫所產生之基。
上述一般式(1)及(2)中,W1、W2係表示聚合性基,可藉由光、熱、觸媒等予以聚合之聚合性基。此聚合性基之較佳例有自由基聚合性基與陽離子聚合性基。自由基聚合性基係以乙烯基,碳數1~6之烷基所取代之取代乙烯基為宜,更佳係自乙烯基及取代乙烯基所選出之乙烯基類。較佳之乙烯基類係以-CR1=CR2R3所示者。在此R1、R2、R3係
C1~6氫烷基或苯基,較佳係氫或C1~3之烷基。自由基聚合性基係以環氧基、氧雜環丁烷基等環狀醚基為宜。此等環狀醚基係可具有取代基者,做為取代基可為碳數1~6之烷基。
上述一般式(1)所示化合物中,上述式(3)或(4)所示化合物係可做為較佳化合物做為例示者。R1、Y1、W1係與上述一般式(1)之R、Y1、W1相同者。
又,本發明之硬化性組成物係還可以將上述一般式(2)所示化合物,以一般式(1)所示化合物與一般式(2)所示化合物之總莫耳數為100時,使其為含有0~95莫耳%。若含有一般式(1)所示化合物時並不特別被限定,惟較佳係含有0~70%範圍之一般式(2)所示化合物為宜。
上述一般式(2)中,Z係C6~C30之芳基、C3~C30之雜芳基或C12~C60之二芳基胺基,較佳係C6~C24之芳基、C3~C24之雜芳基或C12~C48之二芳胺基,更佳係C3~C18之雜芳基或C12~C36之二芳胺基。
上述一般式(2)中,Y2係與上述一般式(1)之Y1、W2係與上述一般式(1)之W1相同者。一般式(2)所示化合物係具有1個聚合性基者。
上述一般式(2)所示化合物係其為具有聚合性基之電荷輸送性之化合物較為適宜,Z為內部具有至少一個上述式(9)所示基為宜。式(9)中,Ar1、Ar2係獨立地表示C6~C30之芳基、C3~C30之雜芳基、與上述一般式(1)之R說明之芳基、雜芳基相同,亦可以Ar1、Ar2與N形成為縮合環。但
Ar1、Ar2係不會為五環以上之縮合環。又,上述一般式(2)之Z為至少其內部具有一個上述式(10)或(11)所示之基為宜。式(10)、(11)中,R2係與上述式(1)所說明之R相同者。
以下在此例示具有一般式(1)所示之具有二個聚合性基之吲哚并咔唑化合物,惟並不被此等所限定。
其次將列示具有一般式(2)聚合性基的化合物具體例,惟並不以此等予以限定。又,所例示之化合物還可以視其需要混合一種或二種予以使用。
本發明之硬化組成物、硬化物係可以僅為一般式(1)之化合物亦無妨,惟因可以導入第二成份而可調節載體之移動度或交聯密度,所以最好係與一般式(2)所示化合物之混合物。另外還可視其需要最好混合共聚合性之化合物、甲苯或THF等一般的有機溶媒、或AIBN或BPO、磷鎢酸等之
各種聚合觸媒使其成為硬化性組成物。
以下例示一般式(1)及(2)所示化合物之合成手法及硬化手法,惟並不被此等所限制者。
本發明之以一般式(1)所示具有二個聚合性基的吲哚并咔唑骨架的化合物係以公知之方法即可製造。例如具有二個乙烯基之化合物係可依以下反應式製造。
本發明具有以一般式(2)所示聚合性基的化合物係除去如市販之二苯胺基苯乙烯之類的乙烯基化合物或苯基丙烯酸酯之類的丙烯基化合物以外,亦可用公知之方法容易地製造。例如具有乙烯基之化合物係可依以下反應式予以製造者。
本發明硬化性組成物係以含有單獨之一般式(1)化合物,或為與一般式(2)之化合物所成的混合物者即可,經溶融或溶解於溶媒、以自旋塗佈法、油墨噴注法、印刷法、噴霧塗佈法、噴射發泡法等塗佈方法予以成膜、直接或乾燥除去溶媒,經過熱、光、觸媒等使其交聯硬化,而成為硬化物。硬化物係可以公知之方法即可極容易地硬化。例如在附有IPO之玻璃基板上製膜之聚(3,4-乙二氧噻吩)/磺化聚苯乙烯酸(PEDOT/PSS)上,使一般式(1)所示化合物溶解於甲苯、苯甲醚、THF等任意溶媒,經由自旋塗佈法予以製膜後,在厭氣條件下,以熱感光板加熱基板,即可得具有交聯構造不溶於溶劑之硬化膜。
又,為一般式(1)及一般式(2)之二種以上混合物時,亦可與單獨時者一樣的條件、調整溫度、硬化時間,又,可以視其需要添加對應聚合性基之觸媒,亦可以同樣地硬化。加上若為二種以上混合物時,使聚合性基成為可共聚合者時,更可順利地進行共聚合。這時使聚合性基為同種類者時則更有利。
本發明之硬化性組成物及硬化物係可使其含於有機EL
元件之有機層,即可成具有優異之有機電場發光元件。較佳係使其含於發光層、電洞輸送層、電子輸送層及電洞、阻止元件層所選出之至少一個有機層為宜。更佳係做為電洞輸送層之材料予以含有為最佳。
在此繼而說明本發明之硬化性組成物,使用硬化物之有機電場發光元件。
本發明之使用硬化性組成物及硬化物之有機電場發光元件係在一對陽極與陰極間具有複數的有機層、尤其最好由電洞輸送層/發光層兼電子輸送層、電洞輸送層兼發光層/電子輸送層、或電洞輸送層/發光層/電子輸送層所成為宜。尤其較佳為電洞輸送層/發光層/電子輸送層之層構造。又,本發明之有機電場發光元件係在形成各有機層後,還可以分別設置保護層。還可更進一步對元件全體使其不受水份或氧氣之傷害,為保護其亦可設置保護膜。
發光層係含有發光材料之層,可為螢光亦可為燐光均無妨。又,發光材料可做為摻雜劑使用,併用宿主材料亦無妨。
發光層中之發光材料係做為螢光發光材料有各種文獻中之公知化合物或以下所示之化合物可使用,惟並不限於此。
另一方面,做為燐光發光材料以含有至少一種選自釕、銠、鈀、銀、錸、鋨、銥、白金及金之金屬的有機金屬錯合物者為宜。該等有機金屬錯合物係在上述專利文獻等係為公知者,此等可被選擇使用。
為得到高發光效率該燐光發光材料有具有以Ir等貴金屬元素為中心金屬之Ir(ppy)3等錯合物類、Ir(bt)2‧acac3等錯合物類、PtOEt3等錯合物類。以下將具體例示燐光發光材料,惟並不只限定於此等者。
可以改變發光材料之種類即可使其成為具有各種發光波長之有機電場發光元件。
以上述發光材料做為摻雜劑使用時,發光層中所含之量係以0.1~50重量%範圍較佳。更佳係1~30重量%。
發光層中之主(host)材料可以使用公知之主材料,還可以將本發明之聚合物做為主材料使用。又,本發明之聚合物亦可以與其他主材料併用。
可使用之公知的主化合物係以具有電洞輸送能力、電子輸送能力,且可以防止發光之長波長化,並且具有高玻璃轉移溫度之化合物較適宜。
這類的其他主材料係可以由多數專利文獻等所知者,所以可自此等選擇。主材料之具體例雖並不特別限定,惟
可為吲哚衍生物、咔唑衍生物、三氮雜茂衍生物、噁唑衍生物、噁二唑衍生物、咪唑衍生物、聚芳基鏈烷衍生物、吡唑啉衍生物、吡唑啉酮衍生物、苯二胺衍生物、烯丙胺衍生物、胺基取代苯丙烯醯苯衍生物、苯乙烯基蒽衍生物、芴酮衍生物、腙衍生物、茋衍生物、矽胺烷衍生物、芳香族第三胺化合物、苯乙烯基胺化合物、芳香族二甲叉系化合物、葉緣素系化合物、蒽醌二甲烷衍生物、蒽酮衍生物、二苯基苯醌衍生物、噻喃二氧化物衍生物、萘苝等之雜環四羧酸無水物、酞菁衍生物、8-喹啉酚衍生物之金屬錯合物或金屬酞菁、苯并唑或苯并噻唑衍生物之金屬錯合物所代表之各種金屬錯合物、聚矽烷系化合物、聚(N-乙烯基咔唑)衍生物、苯胺系共聚物、噻吩低聚物、聚噻吩衍生物、聚苯衍生物、聚苯撑乙烯衍生物、聚芴衍生物等高分子化合物等。
做為形成電洞輸送層的空穴輸送性化合物,本發明之硬化性組成物及硬化物可以有利地被使用。視其需要,在不傷及本發明目的之範圍,第三級胺之三苯胺衍生物、咔唑衍生物等可以配合一種或二種以上所例示之低分子電洞輸送性化合物做為添加劑,做為組成物使用亦可。以下將具體例示電洞輸送性化合物,惟並不被此等所限制。
做為形成電子輸送層之電子輸送性化合物可例示噁二唑衍生物、咪唑衍生物、三氮雜茂衍生物等。視其需要,在不傷及本發明目的之範圍,以低分子電子輸送性化合物等做為添加劑,配合一種或二種以上,做為組成物使用亦可。以下將具體例示電子輸送性化合物,惟並不被此等所限定者。
另外,為提高自陽極的電洞注入效率,可在陽極與電洞輸送層或發光層之間放入電洞注入層。做為形成電洞注入層的電洞注入材料可以使用聚噻吩衍生物、聚吡咯衍生物等導電性高分子。其中尤以聚噻吩衍生物之聚(3,4-乙二氧撑噻吩)/聚苯乙烯磺酸(PEDOT/PSS)係就電洞注入效率之觀點而言較佳。使用電洞注入層時其厚度係較佳為200nm以下,更佳係100nm以下。
陽極係對於電洞注入層、電洞輸送層或發光層等供給電洞者,通常係在玻璃基板上予以形成。本發明中所用之陽極材料並不特別被限定,惟具體而言係有銦-錫氧化物(ITO)、錫氧化物等導電性金屬氧化物、或金、銀、白金等金屬。又,還可以使用市販之附ITO之玻璃。市販之附ITO玻璃係通常以洗淨劑水溶液、溶劑洗淨後,經由UV臭氧照射裝置或等離子體照射裝置予以清淨後被使用。
陰極係可以供給電子予電子輸送層或發光層者,本發明所用之陽極材料雖不特別限定,但具體言可為Li、Mg、Ca、Al等金屬或此等之合金,例如Mg-Ag合金、Mg-Al合金等。
陰極及陽極係可依公知之方法,即可藉由真空蒸著法或濺射方法予以形成。陰極之厚度係較佳為300nm以下、更佳係200nm以下,另一方面陽極之厚度係較佳為200nm下、更佳為100nm以下者。
高分子發光材料,電洞輸送層用高分子材料或電子輸送層用高分子材料等高分子層的製膜方法係通常採用自旋
塗佈法,其他還有對於大面積之有機高分子層要製膜時之手法,還有油墨噴注法、印刷法、噴霧塗佈法、噴射發泡法等,惟並不被此等所限制。
以下將藉由實施例具體說明本發明,惟本發明並不被此等實施例所限定者。
合成例及實施例合成之化合物係自1H NMR(溶劑:重氯仿)FD-MS、GPC、TGA、DSC、UV及IR分析所選出之一種以上分析法予以鑑定。
準備化合物(A-1),依流程圖(S-1)合成化合物(A-2)及(A-3)。
氮氣氛下,於1000ml茄形燒瓶中,在5.00g(19.4mmol)化合物(A-1)中加入100g 1,3-二甲基-2-咪唑二酮,並予攪拌。其次再投入17.97g(77.6mmol)3-碘苯醛與1.38g(9.7mmol)氧化亞酮、8.03g(58.2mmol)碳酸鉀,以母線溫度170℃攪拌22小時。降溫至室溫,過濾固體部份、在濾液中加入乙酸乙酯及2莫耳/1-HCl水溶液、分離油水。以無水硫酸鎂脫水有機層、減壓餾去後,以矽膠柱色譜精製,得1.89g(收率21%)之白色粉末化合物(A-1)。
1H-NMR(400MHz,CDCl3r.t.):δ(ppm);10.149(1H,s)、10.113(1H,s)、8.14-8.21(5H,m)、8.065(1H,dt,J=7,2)、7.913(1H,dt,J=8,2)、7.908(1H,dt,J=8,2),7.846(2H,br t,J=8)、7.21-7.40(6H,m),6.790(1H,ddd,J=2,7,8)5.979(1H,d,J=8)
FD-MS光譜:464(M+、base)
繼而在氮氣氛下,在500ml茄形燒瓶中加入1.84g(3.97mmol)化合物(A-2)、2.97g(8.34mmol)溴化甲基三苯鏻及380ml脫水四氫呋喃,在室溫中予以攪拌。對其以5分鐘之時間滴下0.98g(8.73mol)特丁氧金屬之9ml脫水四氫呋喃溶液,再於室溫反應2.5小時。將此等移至2L茄形燒瓶中投入50ml水。蒸餾去除四氫呋喃後放入乙酸乙酯、飽和食鹽水、經油水分離、有機層以無水硫酸鎂脫水、減壓蒸餾去除。以矽膠柱色譜法精製二次,得0.73g(收率40%)白色粉末之化合物(A-3)。
1H-NMR(400MHz,CDCl3,r.t.):δ(ppm);8.172(1H,
d,J=9),8.150(1H,dd,J=8,2),7.69-7.72(2H,m),7.58-7.63(3H,m),7.554(1H,dr,J=8,2),7.524(1H,ddd,J=9,2,1),7.472(1H,dt,J=7,2),7.30-7.36(3H,m),7.313(1H,d,J=8),7.291(1H,br d,J=8),6.808(1H,dd,J=18,12),6.804(1H,dd,J=18,11),6.803(1H,ddd,J=8,7,1),6.060(1H,d,J=8),5.832(1H,br d,J=18),5.806(1H,br d,J=18),5.355(1H,d,J=12),5.326(1H,d,J=11)
FD-MS光譜:464(M+、base)
經由溶劑洗淨,在經由UV臭氧處理之膜厚150nm所成附ITO玻璃基板上,做為電洞注入層製膜以聚(3,4-乙二氧撑噻吩)/聚苯乙烯磺酸(PEDOT/PSS):(H.C.Stork股份有限公司製,商品名:Clevios PCH 8000)以膜厚25nm製膜。其次,將化合物(A-3)溶解於四氫呋喃,調製為0.4wt%溶液。經由自旋塗佈法做為電洞輸送層製膜為20nm。其次,在厭氣條件下150℃,以3小時熱感光板除去溶劑,進行加熱、硬化。使用真空蒸鍍裝置,做為發光層摻雜劑使用三(2-(p-甲苯基)吡啶)銥(III),做為主要發光層使用4,4’-雙(9H-咔唑-9-基)聯苯,經由共蒸鍍使摻雜劑濃度可成為0.6wt%,製膜為40nm發光層。然後使用真空蒸鍍裝置,以35nm Alq3做為陰極製膜LiF/Al為膜厚170nm,將此元件封在手套箱,製作為有機電場發光元件。
將上述所得之有機電場發光元件連接至外部電源,外加直流電壓,確認有如表1所示之發光特性。表1所示之亮度係在20mA/cm2下之值。又,元件發光光譜之極大波長係550nm,被觀測到有銥錯合物由來之綠色發光。
經由溶劑洗淨,在經由UV臭氧處理之膜厚150nm所成附ITO玻璃基板上,做為電洞注入層製膜以聚(3,4-乙二氧撑噻吩)/聚苯乙烯磺酸(PEDOT/PSS)(H.C.Stork股份有限公司製,商品名:Clevios PCH 8000)以膜厚25nm予以製膜。其次,將化合物(A-3)溶解於四氫呋喃,調製為0.4wt%溶液。經由自旋塗佈法做為電洞輸送層製膜為20nm。其次,在厭氣條件下150℃,以1小時熱感光板除去溶劑進行加熱、硬化。此熱硬化膜係具有交聯構造之膜,不會溶於溶劑。此熱硬化膜係電洞輸送層(HTL)。而且做為發光層摻雜劑使用三(2-(p-甲苯基)吡啶)銥(III),做為主要發光層使用4,4’-雙(9H-咔唑-9-基)聯苯,為使摻雜劑濃度可成為0.6wt%,使其溶解於甲苯,調製成1wt%溶液,經由自旋塗佈法製膜40nm發光層。然後使用真空蒸鍍裝置,以Alq3為35nm做為電子輸送層,做為陰極以LiF/Al製膜為膜厚170nm,將此元件封在手套箱,以製作有機電場發光元件。元件評估係與實施例2一樣進行。另外,自旋塗佈製膜發光層後,使用高速分光橢圓規度器(J.A.Woollam‧JAPAN公司製M2000)確認硬化膜不致於溶解,已積層為發
光層。
實施例3中,單獨改變為化合物(A-3),使用以化合物(A-3):二苯胺基苯乙烯(DPAS)=5:5之比率混合之混合物以外,其他與實施例3一樣製作元件進行評估。
實施例3中,代替化合物(A-3)使用下述化合物(A-4)以外,其他則與實施例3一樣製作元件進行評估。另外,化合物(A-4)係使用流程圖(S-1)所示之自(A-1)予以製作(A-2)之手法加以合成。
實施例3中,除使用以下化合物(A-5)以外,其他則與實施例3一樣製作元件予以評估。另外,化合物(A-5)係以流程圖(S-1)所示手法予以合成。
實施例2中,除不使用化合物(A-3)以外,其他則與實施例2一樣製作元件予以評估。
實施例2中,代替(A-3)使用下述化合物(B1)予以作成電洞輸送層,對於硬化使用交流電源方式使用紫外線照射裝置,照射90秒之紫外線,以光聚合進行硬化,除此以外則與實施例2一樣製作元件予以評估。
實施例3中,除不使用化合物(A-3)以外,其他則與實
施例3一樣製作元件予以評估。
電洞輸送層(HTL)使用之化合物與發光層之製膜方式,以及元件評估結果則示如表1。
由實施例2與比較例1之比較可知,使用本發明化合物後,以濕式作業形成電洞輸送層之元件係示有優異之元件特性者。又由實施例3~6與比較例2、3之比較可知,使用本發明化合物以濕式作業形成電洞輸送層,再以濕式作業形成鄰接層之發光層時,亦獲知可以形成極佳之層合,示有極佳之發光特性。
在有機電場發光元件之有機層使用本發明之硬化性組成物及硬化物時,可以改善電洞注入層或電子耐性、電荷
輸送性,而可得極優異之發光效率。又,在上層塗佈含有其他材料之有機層時因可以層合,而可以極易製作大面積之元件。使用此硬化性組成物或硬化物之有機電場發光元件係因具有優異之發光效率,所以被考慮應用於被使用在照明裝置,畫像顯示裝置,顯示裝置用背光等的有機電場發光元件上之應用,其技術上之價值係莫大者。
Claims (7)
- 一種有機電場發光元件,其係於被層合於基板上之陽極層與陰極層之間具備有機層之有機電場發光元件,該有機層之至少一層含有使下述硬化性組成物硬化所成的硬化物,前述硬化性組成物係以一般式(1)所示化合物與一般式(2)所示化合物之總莫耳數為100時,一般式(1)所示化合物含有5~100莫耳%、一般式(2)所示化合物含有0~95莫耳%者,
- 如申請專利範圍第1項之有機電場發光元件,其中一般式(1)所示化合物為以下式(3)或(4)所示化合物,
- 如申請專利範圍第1項之有機電場發光元件,其中一般式(2)中之Z為在內部中具有至少一個以下式(9)所示基,
- 如申請專利範圍第1項之有機電場發光元件,其中式(2)中Z為內部具有至少一個以下式(10)或(11)所示基者,
- 如申請專利範圍第1項之有機電場發光元件,其中一般式(1)、式(1a)及一般式(2)中之W1、W2為選自乙烯基及取代乙烯基之乙烯基類,一般式(1)所示化合物為具有二個乙烯基類,一般式(2)所示化合物為具有1個乙烯基類者。
- 如申請專利範圍第1項之有機電場發光元件,其中式(1)所示化合物為使100莫耳%之硬化性組成物予以硬化所成者。
- 如申請專利範圍第1項之有機電場發光元件,其中含有硬化物之有機層為電洞輸送層。
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