CN102958906A - 新颖有机电致发光化合物及使用该化合物的有机电致发光装置 - Google Patents

新颖有机电致发光化合物及使用该化合物的有机电致发光装置 Download PDF

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CN102958906A
CN102958906A CN2011800315542A CN201180031554A CN102958906A CN 102958906 A CN102958906 A CN 102958906A CN 2011800315542 A CN2011800315542 A CN 2011800315542A CN 201180031554 A CN201180031554 A CN 201180031554A CN 102958906 A CN102958906 A CN 102958906A
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organic electroluminescent
heteroaryl
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CN102958906B (zh
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金荣佶
金侈植
赵英俊
权赫柱
金圣珉
金奉玉
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Rohm and Haas Electronic Materials Korea Ltd
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Abstract

本发明提供新颖有机电致发光化合物及使用该化合物的有机电致发光装置。由于该有机电致发光化合物呈现蓝色高发光效率及优异的寿命性质，其可用于制造具有极高操作寿命的OLED装置。

Description

新颖有机电致发光化合物及使用该化合物的有机电致发光装置
【技术领域】
本发明涉及新颖有机电致发光化合物及使用该化合物的有机电致发光装置，更特别地，本发明涉及使用新颖有机电致发光化合物作为蓝色电致发光材料及使用该电致发光化合物作为掺杂剂的有机电致发光装置。
【背景技术】
于显示器装置中，电致发光(electroluminescent，EL)装置作为自发光显示器装置的优越性在于其视角广、对比度高且反应速率快。1987年，伊士曼-柯达(Eastman Kodak)首先研发出使用低分子量的芳香二胺及铝的络合物作为形成电致发光层的有机EL装置的物质[Appl.Phys.Lett．51,913,1987]。
于有机EL装置中，决定其包括发光效率及操作寿命的效能的最重要因素为电致发光材料。该电致发光材料的若干要求包含：在固态中的高电致发光量子产率(quantum yield)、高电子及空穴迁移率、于真空沉积过程中对分解的抗性、形成均匀薄膜的能力及稳定性。
有机电致发光材料一般可分为高分子材料及低分子材料。就分子结构层面来看，该低分子材料包含金属络合物及不含金属的完全有机电致发光材料。此等电致发光材料包含螯合剂络合物例如三（8-喹啉根）铝络合物(tris(8-quinolinolato)aluminum complex）、香豆素衍生物、四苯基丁二烯衍生物、双（苯乙烯基亚芳基）衍生物及
Figure BDA00002650354100011
二唑衍生物。已有报道指出可从那些材料中获得从蓝色至红色的可见光区域的发光，且该等材料预期可实现全彩显示器装置。
同时，对于传统的蓝色材料而言，自日本出光兴产株式会社(Idemitsu-Kosan)研发二苯乙烯基-联苯(DPVBi)(化合物a)以来，许多材料已被研发及商品化。除了日本出光兴产株式会社的蓝色材料系统外，亦已知Kodac的二萘基蒽(DNA)（化合物b）、四（叔丁基）苝(化合物C)体系等。然而，关于这些材料仍应进行广泛的研究及研发。
目前以最高效率闻名的日本出光兴产株式会社的肉桂基(distryl)化合物系统具有6流明/瓦(1m/W)的功率效率以及超过30,000小时的有用装置寿命。然而，当将该系统应用于全彩显示器时，由于随着操作时间色纯度的下降，寿命仅为几千小时。在蓝色电致发光的例子中，从发光效率的观点来看，若电致发光波长往较长波长方向稍微移动会变得有利。然而，因为蓝色色纯度不足以符合要求，故不易将该材料应用于高品质的显示器。此外，由于色纯度、效率及热稳定性等问题，因此亟需研究及开发该等材料。
Figure BDA00002650354100021
【发明内容】
技术问题
为了克服上述传统技术的问题而作了大量的努力，本申请的发明人发现了新颖有机电致发光化合物，其实现了具有优异发光效率及显著改善操作寿命性质的有机电致发光装置。本发明的目的是提供有机电致发光化合物，且与传统掺杂剂材料相比，该化合物具有在适当的色坐标条件下提供更好的发光效率及装置寿命的骨架，同时克服上述问题；以及一种使用该有机电致发光化合物的高效率且长寿命的有机电致发光装置。
技术解决方案
本发明提供新颖有机电致发光化合物及使用该化合物的有机电致发光装置。该有机电致发光化合物为化学式1表示的化合物。由于本发明的有机电致发光化合物具有较高的蓝色发光效率及优异的寿命性质，因此其可用于制造具有极高操作寿命的OLED装置。
化学式1
Figure BDA00002650354100031
其中，
Ar1至Ar4独立地表示（C6-C30）芳基、含有一个或多个选自N、O及S的杂原子的（C2-C30）杂芳基、含有一个或多个选自N、O及S的杂原子的5至7元杂环烷基、(C3-C30)环烷基、金刚烷基、(C7-C30)双环烷基或
Figure BDA00002650354100032
或者Ar1及Ar2或Ar3及Ar4可通过具有或不具有芳香环或杂芳香环的（C3-C30）亚烷基或（C3-C30）亚烯基独立地相连接以形成稠合环，且该亚烷基的碳原子可进一步经NR21、O、S或SiR22R23取代；
R1至R6及R11至R13独立地表示氢、(C1-30)烷基、(C3-C30)环烷基、(C6-C30)芳基、(C2-C30)杂芳基、(C1-C30)烷氧基、（C6-C60）芳氧基、单-或二-(C1-C30)烷基胺基、单-或二-（C6-C30）芳基胺基、(C6-C30)芳基(C1-C30)烷基胺基、三（C1-C30）烷基甲硅烷基、二(C1-C30)烷基(C6-C30)芳基甲硅烷基或三(C6-C30)芳基甲硅烷基；
R21至R23独立地表示(C1-C30)烷基、卤(C1-C30)烷基、(C1-C30)烷氧基、吗啉基、硫代吗啉基、哌啶基、含有一个或多个选自N、O及S的杂原子的5至7元杂环烷基、（C3-C30）环烷基、金刚烷基、卤素、氰基、(C6-C30)芳基、(C2-C30)杂芳基、三(C1-C30)烷基甲硅烷基、二(C1-C30)烷基（C6-C30）芳基甲硅烷基或三(C6-C30)芳基甲硅烷基，或者R22及R23可通过具有或不具有稠合环的（C3-C30）亚烷基或(C3-C30)亚烯基相连接以形成稠合环；以及
R1至R6的烷基、环烷基、芳基、杂芳基、烷氧基、芳氧基、烷基胺基、芳基胺基、芳基烷基胺基、三烷基甲硅烷基、二烷基芳基甲硅烷基或三芳基甲硅烷基；Ar1至Ar4的芳基、杂芳基、杂环烷基、环烷基、金刚烷基或双环烷基；通过Ar1及Ar2或Ar3及Ar4各自的连接所形成的该稠合环；以及R21至R23的烷基、卤烷基、烷氧基、吗啉基、硫代吗啉基、哌啶基、杂环烷基、环烷基、金刚烷基、芳基、杂芳基、三烷基甲硅烷基、二烷基芳基甲硅烷基或三芳基甲硅烷基可进一步经一个或多个选自下列取代基的取代基取代：（C1-C30）烷基、卤（C1-C30）烷基、（C1-C30）烷氧基、（C1-C30）烷基硫基、哌啶基、吗啉基、硫代吗啉基、含有一个或多个选自N、O及S的杂原子的5至7元杂环烷基、（C3-C30）环烷基、卤素、氰基、硝基、羟基、(C6-30)芳基、(C6-30)芳氧基、（C6-C30）芳基硫基、（C2-C30）杂芳基、（C6-C30）芳基（Cl-C30）烷基、(C1-C30)烷基（C6-C30）芳基、三（C1-C30）烷基甲硅烷基、二（C1-C30）烷基（C6-C30）芳基甲硅烷基及三（C6-C30）芳基甲硅烷基。
在本发明中，“烷基”、“烷氧基”及含有“烷基”部分的其他取代基包含直链及支链两者。在本发明中，“芳基”意指自芳香烃去除一个氢原子后所得的有机基团，且可包含4至7元，尤指5元或6元的单环或稠合环。具体实例包含但不限于：苯基、萘基、联苯基、蒽基、茚基、芴基、菲基、苯并菲基(triphenylenyl)、芘基、苝基、
Figure BDA00002650354100041
基(chrysenyl)、稠四苯基(naphthacenyl)、荧蒽基(fluoranthenyl)等。在本发明中，“杂芳基”意指含有作为芳香环骨架原子的选自B、N、O、S、P(=O)、Si及Se的1至4个杂原子，以及作为剩余芳香环骨架原子的碳原子的芳基。该杂芳基可为5元或6元单环杂芳基或为与苯环缩合所得的多环杂芳基，并可呈部分饱和。
杂芳基包含二价芳基，其中，该环中的杂原子可经氧化或季化(quaternized)以形成诸如N-氧化物或季盐。具体实例包含但不限于：单环杂芳基，诸如呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异
Figure BDA00002650354100042
唑基、
Figure BDA00002650354100043
唑基、二唑基、三嗪基、四嗪基、三唑基、四唑基、呋咱基(furazanyl)、吡啶基、吡嗪基、嘧啶基、哒嗪基等；多环杂芳基，诸如苯并呋喃基、苯并噻吩基、异苯并呋喃基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异唑基、苯并
Figure BDA00002650354100046
唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基(cinnolinyl)、喹唑啉基、喹嗪基（quinolizinyl）、喹喔啉基、咔唑基、啡啶基、苯并二氧戊基(benzodioxolyl)等；其N-氧化物（例如，吡啶基N-氧化物、喹啉基N-氧化物等）；其季盐等，但不限于此。
在本发明中，“（C1-C30）烷基、（C1-C30）烷氧基、单或二(C1-C30)烷基胺基、(C6-C30)芳基(C1-C30)烷基胺基、三(C1-C30)烷基甲硅烷基、二(C1-C30)烷基(C6-C30)芳基甲硅烷基、卤素(C1-C30)烷基、(C1-C30)烷基硫基、(C6-C30)芳基(C 1-C30)烷基、(C 1-C30)烷基(C6-C30)芳基”等的烷基部分可具有1至20个碳原子，更具体而言，可具有1至10个碳原子。“（C6-C30）芳基、单或二(C6-C30)芳基胺基、（C6-C30）芳基(C1-C30)烷基胺基、二(C1-C30)烷基（C6-C30）芳基甲硅烷基、三（C6-C30）芳基甲硅烷基、（C6-C30）芳氧基、（C6-C30）芳基硫基、（C6-C30）芳基（C1-C30）烷基、(C1-C30)烷基（C6-C30）芳基”等的芳基部分可具有6至20个碳原子，更具体而言，可具有6至12个碳原子。“（C3-C30）杂芳基”的杂芳基可具有4至20个碳原子，更具体而言，可具有4至12个碳原子。“（C3-C30）环烷基”的环烷基可具有3至20个碳原子，更具体而言，可具有3至7个碳原子。“（C3-C30）亚烷基或亚烯基”的亚烷基或亚烯基可具有3至20个碳原子，更具体而言，可具有3至10个碳原子。
又，本发明的有机电致发光化合物可包含下列化学式2表示的化合物：
化学式2
其中，
R5及R6独立地表示氢、（C6-C30）芳基或(C2-C30)杂芳基；
Ar1至Ar4独立地表示（C6-C30）芳基、含有一个或多个选自N、O及S的杂原子的（C2-C30）杂芳基、含有一个或多个选自N、O及S的杂原子的5至7元杂环烷基、(C3-C30)环烷基、金刚烷基、（C7-C30）双环烷基或
Figure BDA00002650354100052
或者Ar1及Ar2或Ar3及Ar4可各自通过具有或不具有芳香环或杂芳香环的(C3-C30)亚烷基或(C3-C30)亚烯基相连接以形成稠合环，且该亚烷基的碳原子可进一步经NR21、O、S或SiR22R23取代；
R21至R23独立地表示(C1-C30)烷基或(C6-C30)芳基，或者R22及R23可通过具有或不具有稠合环的(C3-C30)亚烷基或（C3-C30）亚烯基相连接以形成稠合环；以及
R5及R6的芳基或杂芳基；Ar1至Ar4的芳基、杂芳基、杂环烷基、环烷基、金刚烷基或双环烷基；通过Ar1及Ar2或Ar3及Ar4各自的连接所形成的该稠合环；以及R21至R23的烷基或芳基可进一步经一个或多个选自下列取代基的取代基取代：（C1-C30）烷基、卤(C1-C30)烷基、(C1-C30)烷氧基、(C1-C30)烷基硫基、哌啶基、吗啉基、硫代吗啉基、含有一个或多个选自N、O及S的杂原子的5至7元杂环烷基、(C3-C30)环烷基、卤素、氰基、硝基、羟基、(C6-30)芳基、(C6-30)芳氧基、(C6-C30)芳基硫基、(C2-C30)杂芳基、（C6-C30）芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、三(C1-C30)烷基甲硅烷基、二(C1-C30)烷基(C6-C30)芳基甲硅烷基及三（C6-C30）芳基甲硅烷基。
又，当Ar1及Ar2与Ar3及Ar4各自通过亚烷基或亚烯基连接形成的
Figure BDA00002650354100061
及
Figure BDA00002650354100062
独立地选自下列结构，但其并不限于此：
Figure BDA00002650354100063
其中，
R21至R25独立地表示（C1-C30）烷基或（C6-C30）芳基。
更具体而言，Ar1至Ar4独立地选自下列结构，但其并不限于此：
Figure BDA00002650354100071
本发明的有机电致发光化合物可通过下列化合物具体例示之，但其并不限于此：
Figure BDA00002650354100081
Figure BDA00002650354100101
Figure BDA00002650354100111
本发明的有机电致发光化合物可通过下列方案1制备，但其并不限于此。
方案1
Figure BDA00002650354100112
其中，
Ar1至Ar4及R1至R6的定义与化学式1定义相同。
本发明提供有机电致发光装置，其包括第一电极；第二电极；以及置于该第一电极与该第二电极之间的一层或多层有机层；其中，该有机层包括一种或多种化学式1表示的有机电致发光化合物。
在该有机电致发光装置中，当使用一种或多种化学式1的有机电致发光化合物作为电致发光掺杂剂时，该有机层包括含有一种或多种基质的电致发光层。用于本发明的有机电致发光装置的该基质并无特别限制，但可为选自下列化学式3或4表示的化合物。下列化学式3或4的基质化合物的具体结构如韩国专利申请案第10-2008-0060393号第<162>至<210>段中所例示，但其并不限于此。
化学式3
(Ar11)a-L1-(Ar12)b
化学式4
(Ar13)c-12-(Ar14)d
其中，
L1表示(C6-C30)亚芳基或(C4-C30)亚杂芳基；
L2表示亚蒽基；
Ar11至Ar14独立地表示氢、氘、(C1-C30)烷基、(C1-C30)烷氧基、卤素、(C4-C30)杂芳基、(C5-C30)环烷基或(C6-C30)芳基，且Ar11至Ar14的该环烷基、芳基或杂芳基可进一步经一个或多个选自下列取代基的取代基取代：具有或不具有一个或多个选自氘、(C1-C30)烷基、卤(C1-C30)烷基、(C1-C30)烷氧基、(C3-C30)环烷基、卤素、氰基、三(C1-C30)烷基甲硅烷基、二(C1-C30)烷基（C6-C30）芳基甲硅烷基及三(C6-C30)芳基甲硅烷基的取代基的(C6-C30)芳基或(C4-C30)杂芳基；氘：(C1-C30)烷基；卤（C1-C30）烷基；(C1-C30)烷氧基；(C3-C30)环烷基；卤素；氰基；三（C1-C30）烷基甲硅烷基：二(C1-C30)烷基(C6-C30)芳基甲硅烷基及三(C6-C30)芳基甲硅烷基：以及
a、b、c及d独立地表示0至4的整数。
该电致发光层意指发生电致发光的层，且其可为单层或由两层或更多层层叠(1aminate)而成的多层。当依据本发明的描述而使用基质-掺杂剂的混合物时，该电致发光基质确实可显著改善发光效率。掺杂浓度可为0.5至10重量%。与现存其他基质材料相比，本发明的电致发光基质提供优异的空穴及电子传导率，以及极高的稳定性，并提供显著改善的发光效率及操作寿命。因此，当选择化学式3或4表示的化合物作为电致发光基质时，其可弥补本发明的化学式1表示的有机电致发光化合物的电子缺陷。
该有机电致发光装置可包括化学式1表示的有机电致发光化合物，还可包括一种或多种选自芳基胺(arylamine)化合物及苯乙烯基胺(styrylamine)化合物的化合物。该芳基胺或苯乙烯基胺化合物的具体实例于韩国专利申请案第10-2008-0060393号第<212>至<224>段中提供，但其并不限于此。
再者，在本发明的有机电致发光装置中，该有机层除了包括化学式1表示的有机电致发光化合物之外，可进一步包括一种或多种选自下列的金属：元素周期表第1族的有机金属、第2族、第4周期与第5周期的过渡金属、镧系金属及d-过渡元素。该有机层可包括电致发光层及电荷产生层。
本发明可实现具有独立发光模式的像素结构的有机电致发光装置，其中，包含本发明的化学式1表示的有机电致发光化合物的该有机电致发光装置作为次像素；以及一个或多个包含选自Ir、Pt、Pd、Rh、Re、Os、Tl、Pb、Bi、In、Sn、Sb、Te、Au及Ag的一种或多种金属化合物的次像素同时平行图案化。
再者，该有机层除了包含该有机电致发光化合物之外，可同时包含一层或多层发射蓝光、红光或绿光的有机电致发光层，以实现发射白光的有机电致发光装置。该发射蓝光、绿光或红光的化合物可以韩国专利申请案第10-2008-0123276号、第10-2008-0107606号或第10-2008-0118428号中揭示的化合物例示之，但其并不限于此。
在本发明的有机电致发光装置中，可将一层（后文中称为“表面层”）选自硫属化合物(chalcogenide)层、金属卤化物层及金属氧化物层的层设置于该电极对的一个或两个电极的内表面上。更具体而言，可将硅或铝的硫属化合物（包括氧化物）层设置于电致发光介质（medium）层的阳极表面上，并可将金属卤化物层或金属氧化物层设置于电致发光介质层的阴极表面上。借此可得到操作稳定性。该硫属化合物可为，诸如：SiOX(1＝x＝2)、AlOx(l＝x＝1.5)、SiON、SiAlON等。该金属卤化物可为，诸如：LiF、MgF2、CaF2、稀土金属氟化物等。该金属氧化物可为，诸如：Cs2O、Li2O、MgO、SrO、BaO、CaO等。
在本发明的有机电致发光装置中，优选亦可将电子传输化合物与还原性掺杂剂的混合区域、或空穴传输化合物与氧化性掺杂剂的混合区域设置于前述所制造的电极对的至少一个表面上。于该例中，由于电子传输化合物被还原成阴离子，因而使电子变得更容易自混合区域注入与传输至电致发光介质。此外，由于空穴传输化合物被氧化成阳离子，因而使空穴变得更容易自混合区域注入与传输至电致发光介质。优选的氧化性掺杂剂包含各种路易斯酸及受体化合物(acceptor compound)。优选的还原性掺杂剂包含碱金属、碱金属化合物、碱土金属、稀土金属、及其混合物。再者，可通过使用还原性掺杂剂层作为电荷产生层来制备具有两层或更多层电致发光层的发射白光的有机电致发光装置。
有利效果
由于本发明的有机电致发光化合物展现良好蓝色发光效率及优异寿命性质，其可用于制造具有极高操作寿命的OLED装置。
具体实施方式
本发明将进一步说明关于本发明的有机电致发光化合物、该化合物的制备方法、以及使用该化合物的装置的发光性质。然而，下列实施例仅提供用于例示性说明用，而非意旨限制本发明的范围。
[制备例1]化合物68的制备
Figure BDA00002650354100141
化合物B的制备
将化合物A(20克(g)，96.05毫摩尔(mmol）、过氧化苯甲酰(3.lg，9.60mmol，75%)、硝基苯(300毫升(mL))及Br2(10.85mL，211.3mmol)在室温混合并在120℃加热。3小时之后，使混合物冷却至室温，以KOH溶液中和及以二氯甲烷(MC)萃取。在减压下蒸馏后，以乙酸乙酯(EA)再结晶所得固体而获得化合物B(20g，56.92%)。
化合物C的制备
将2-溴萘(25.4g，122.95mmol)溶解于THF(1000mL)，并在-78℃缓慢加入正丁基锂(n-buLi)(114.7mmol，2.5摩尔浓度(M)，于己烷）。30分钟之后，在室温搅拌混合物。30分钟之后，将化合物B(14.lg，40mmol)加入该混合物。搅拌该混合物12小时并以蒸馏水及MC萃取。以MgSO4干燥有机层并在减压下通过蒸馏移除溶剂后，通过柱分离而获得化合物C(10g，40%)(MC:己烷=1:1)。
化合物D的制备
将化合物C(10g，16.06mmol)加入乙酸(500mL)，且将该混合物加热至130℃。将Zn(20.2g)缓慢加入该混合物，接着于其内缓慢加入HCl(20mL)。30分钟之后，将Zn(10g)加入该混合物，接着于其内再加入HCl(10mL)。回流搅拌该混合物12小时后，使该混合物冷却至室温。所产生的固体在减压下通过加入蒸馏水而过滤。所得固体以NaOH溶液清洗并通过柱分离纯化而获得化合物D(6.5g，11.04mmol，68.74%)。
化合物68的制备
加入化合物D(5g，8.49mmol)、二苯基胺(3.7g，22.09mmol)、Pd(OAc)2(0.09g,0.42mmol)及NaOt-bu(3.26g，33.99mmol)。于氮气氛围下，将甲苯(200mL)及P(t-bu)3（0.50mL，1.019mmol，50%于二甲苯）加入该混合物。回流搅拌该混合物。搅拌该混合物12小时后，使该混合物冷却至室温并以蒸馏水及MC萃取。以MgSO4干燥有机层并在减压下通过蒸馏移除溶剂后，通过柱分离纯化而获得化合物68(2.9g，75.8%)。
1H NMR  (CDCl3,200MHz):d=6.63(8H,m),6.81(4H,m),7.02(2H,m),7.2(8H,m),7.58~7.59(6H,m),7.73(2H,m),7.87-7.92(4H,m),8(4H,m)，8.13(2H,m)．MS/FAB：764.96（实测值），764.32（计算值）。
根据制备例1的方法制备有机电致发光化合物1至67。所制备的有机电致发光化合物的1H NMR及MS/FAB显示于表1中。
Figure BDA00002650354100151
Figure BDA00002650354100161
Figure BDA00002650354100171
Figure BDA00002650354100181
Figure BDA00002650354100191
Figure BDA00002650354100201
Figure BDA00002650354100221
Figure BDA00002650354100231
Figure BDA00002650354100241
[实施例1至3]使用本发明的有机电致发光化合物的OLED装置的制造
使用本发明的电致发光材料制造OLED装置。首先，使用超声波依序以三氯乙烯、丙酮、乙醇及蒸馏水清洗得自OLED（Samsung Corning所制得）用玻璃的透明电极ITO薄膜(15Ω/□)，并储存于异丙醇中备用。然后，将ITO基板装配于真空气相沉积装置的基板夹中，并将4,4',4″-三（N,N-(2-萘基)-苯基胺基）三苯胺（2-TNATA）置于该真空气相沉积装置的一小室中，然后抽气使该腔室内到最高达10-6托(torr)真空。然后，对该小室施加电流以蒸发2-TNATA，从而于该ITO基板上形成厚度为60纳米(nm)的空穴注入层。
接着，将N,N'-双（α-萘基）-N,N'-二苯基-4,4'-胺(NPB)置于该真空气相沉积装置的另一小室中，并对该小室施加电流以蒸发NPB，从而于该空穴注入层上形成厚度为20nm的空穴传输层。
形成该空穴注入层及空穴传输层之后，于所形成的层上气相沉积电致发光层。将下列结构的DNA（实施例1至3）置于真空气相沉积装置的一小室中，并将本发明的化合物置于另一小室中。然后，以100:3的沉积速率于该空穴传输层上气相沉积厚度为30nm的电致发光层。
Figure BDA00002650354100251
接着，在该电致发光层上气相沉积厚度为20nm的三（8-羟基喹啉基）铝(III)(Alq)作为电子传输层。然后，气相沉积具有厚度为1至2nm的8-羟基喹啉锂(lithium quinolate，Liq)作为电子注入层后，使用另一真空气相沉积装置形成厚度为150nm的Al阴极，以制造出OLED。
用于该OLED的各个化合物皆是已通过在10-6torr真空升华而纯化者。
于1,000cd/m2分别测量包括本发明的有机电致发光化合物的OLED（实施例1至3）的发光效率，且结果显示于表2中。
表2
从表2中可知，本发明的有机电致发光化合物提供深蓝色。即，当蓝色为实现接近有机电致发光显示器的NTSC标准的颜色所需者时，本发明的有机电致发光化合物可为有用。由于菲衍生物具有高玻璃转移温度，因此可获得高热稳定性。如本发明所述，本发明的有机电致发光化合物作为具有高纯度的发射蓝光材料使用。
工业适用性
由于如本发明所述的有机电致发光化合物呈现蓝色高发光效率及优异的寿命性质，其可用于制造具有极高操作寿命的OLED装置。

Claims (10)

1.一种化学式1表示的有机电致发光化合物：
[化学式1]
Figure FDA00002650354000011
其中，
Ar1至Ar4独立地表示(C6-C30)芳基、含有一个或多个选自N、O及S的杂原子的(C2-C30)杂芳基、含有一个或多个选自N、O及S的杂原子的5至7元杂环烷基、（C3-C30）环烷基、金刚烷基、(C7-C30)双环烷基或，
Figure FDA00002650354000012
或者Ar1及Ar2或Ar3及Ar4各自可通过具有或不具有芳香环或杂芳香环的（C3-C30）亚烷基或（C3-C30）亚烯基连接以形成稠合环，且该亚烷基的碳原子可进一步经NR21、O、S或SiR22R23取代；
R1至R6及R11至R13独立地表示氢、(C1-30)烷基、（C3-C30）环烷基、（C6-C30）芳基、（C2-C30）杂芳基、(C1-C30)烷氧基、（C6-C60）芳氧基、单-或二-（C1-C30）烷基胺基、单-或二-（C6-C30）芳基胺基、(C6-C30)芳基（C1-C30）烷基胺基、三（C1-C30）烷基甲硅烷基、二(C 1-C30)烷基（C6-C30）芳基甲硅烷基或三（C6-C30）芳基甲硅烷基；
R21至R23独立地表示(C1-C30)烷基、卤(C1-C30)烷基、（C1-C30）烷氧基、吗啉基、硫代吗啉基、哌啶基、含有一个或多个选自N、O及S的杂原子的5至7元杂环烷基、(C3-C30)环烷基、金刚烷基、卤素、氰基、（C6-C30）芳基、(C2-C30)杂芳基、三（C1-C30）烷基甲硅烷基、二(C1-C30)烷基(C6-C30)芳基甲硅烷基或三（C6-C30）芳基甲硅烷基，或者R22及R23可通过具有或不具有稠合环的（C3-C30）亚烷基或(C3-C30)亚烯基相连接以形成稠合环；以及
R1至R6的烷基、环烷基、芳基、杂芳基、烷氧基、芳氧基、烷基胺基、芳基胺基、芳基烷基胺基、三烷基甲硅烷基、二烷基芳基甲硅烷基或三芳基甲硅烷基：Ar1至Ar4的芳基、杂芳基、杂环烷基、环烷基、金刚烷基或双环烷基；通过Ar1及Ar2或Ar3及Ar4各自的连接所形成的该稠合环；以及R21至R23的烷基、卤烷基、烷氧基、吗啉基、硫代吗啉基、哌啶基、杂环烷基、环烷基、金刚烷基、芳基、杂芳基、三烷基甲硅烷基、二烷基芳基甲硅烷基或三芳基甲硅烷基可进一步经一个或多个选自下列取代基的取代基取代：（C1—C30）烷基、卤(C1-C30)烷基、(C1-C30)烷氧基、(C1-C30)烷基硫基、哌啶基、吗啉基、硫代吗啉基、含有一个或多个选自N、O及S的杂原子的5至7元杂环烷基、(C3-C30)环烷基、卤素、氰基、硝基、羟基、(C6-30)芳基、(C6-30)芳氧基、（C6-C30）芳基硫基、（C2-C30）杂芳基、(C6-C30)芳基（C1-C30）烷基、(C1-C30)烷基（C6-C30）芳基、三（C1-C30）烷基甲硅烷基、二（C1-C30）烷基(C6-C30)芳基甲硅烷基及三（C6-C30）芳基甲硅烷基。
2.如权利要求1所述的有机电致发光化合物，其以化学式2表示：
化学式2
其中，
R5及R6独立地表示氢、（C6-C30）芳基或(C2-C30)杂芳基；
Ar1至Ar4独立地表示(C6-C30)芳基、含有一个或多个选自N、O及S的杂原子的（C2-C30）杂芳基、含有一个或多个选自N、O及S的杂原子的5至7元杂环烷基、（C3-C30）环烷基或
Figure FDA00002650354000022
或者Ar1及Ar2或Ar3及Ar4各自可通过具有或不具有芳香环或杂芳香环的（C3-C30）亚烷基或(C3-C30)亚烯基连接以形成稠合环，且该亚烷基的碳原子可进一步经NR21、O、S或SiR22R23取代；
R21至R23独立地表示(C1-C30)烷基或(C6-C30)芳基，或者R22及R23可通过具有或不具有稠合环的（C3-C30）亚烷基或（C3-C30）亚烯基相连接以形成稠合环；以及
R5及R6的芳基或杂芳基；Ar1至Ar4的该芳基、杂芳基、杂环烷基、环烷基、金刚烷基或双环烷基；通过Ar1及Ar2或Ar3及Ar4各自的连接所形成的稠合环：以及R21至R23的烷基或芳基可进一步经一个或多个选自下列取代基的取代基取代：(C1-C30)烷基、卤(C1-C30)烷基、（C1-C30）烷氧基、(C1-C30)烷基硫基、哌啶基、吗啉基、硫代吗啉基、含有一个或多个选自N、O及S的杂原子的5至7元杂环烷基、(C3-C30)环烷基、卤素、氰基、硝基、羟基、(C6-30)芳基、(C6-30)芳氧基、(C6-C30)芳基硫基、(C2-C30)杂芳基、（C6-C30）芳基（C1-C30）烷基、(C1-C30)烷基（C6-C30）芳基、三(C1-C30)烷基甲硅烷基、二(C1-C30)烷基(C6-C30)芳基甲硅烷基及三(C6-C30)芳基甲硅烷基。
3.如权利要求2所述的有机电致发光化合物，其中，
Figure FDA00002650354000031
及
Figure FDA00002650354000032
独立地选自下列结构：
Figure FDA00002650354000033
其中，
R21至R25独立地表示（C1-C30）烷基或(C6-C30)芳基。
4.如权利要求1所述的有机电致发光化合物，其选自下列化合物：
Figure FDA00002650354000061
Figure FDA00002650354000071
5.一种有机电致发光装置，包括如权利要求1至4中任一项所述的有机电致发光化合物。
6.如权利要求5所述的有机电致发光装置，其包括第一电极：第二电极；以及一层或多层置于该第一电极与该第二电极间的有机层；其中，该有机层包括一种或多种有机电致发光化合物，以及一种或多种化学式3或4表示的基质化合物：
化学式3
(Ar11)a-L1-(Ar12)b
化学式4
(Ar13)c-L2-(Ar14)d
其中，
L1表示（C6-C30）亚芳基或（C4-C30）亚杂芳基；
L2表示亚蒽基；
Ar11至Ar14独立地表示氢、氘、（C1-C30）烷基、（C1-C30）烷氧基、卤素、（C4-C30）杂芳基、（C5-C30）环烷基或（C6-C30）芳基，且Ar11至Ar14的环烷基、芳基或杂芳基可进一步经一个或多个选自下列取代基的取代基取代：具有或不具有一个或多个选自氘、（C1-C30）烷基、卤（C1-C30）烷基、(C1-C30)烷氧基、（C3-C30）环烷基、卤素、氰基、三（C1-C30）烷基甲硅烷基、二（C1-C30）烷基（C6-C30）芳基甲硅烷基及三（C6-C30）芳基甲硅烷基的取代基的(C6-C30)芳基或（C4-C30）杂芳基；氘；（C1-C30）烷基；卤（C1-C30）烷基；(C1-C30)烷氧基；（C3-C30）环烷基；卤素；氰基：三（C1-C30）烷基甲硅烷基；二（C1-C30）烷基（C6-C30）芳基甲硅烷基及三(C6-C30)芳基甲硅烷基；以及
a、b、c及d独立地表示0至4的整数。
7.如权利要求6所述的有机电致发光装置，其中，该有机层进一步包括一种或多种选自芳基胺化合物及苯乙烯基芳基胺化合物的化合物，或者一种或多种选自下列的金属：元素周期表第1族的有机金属、第2族、第4周期与第5周期的过渡金属、镧系金属及d-过渡元素。
8.如权利要求6所述的有机电致发光装置，其系发射白光的有机电致发光装置，其中，该有机层同时包括一层或多层发射蓝光、红光或绿光的有机电致发光层。
9.如权利要求6所述的有机电致发光装置，其中，该有机层包括电致发光层及电荷产生层。
10.如权利要求6所述的有机电致发光装置，其中，于该电极对的一个或二个电极的内表面上设置还原性掺杂剂与有机物质的混合区域、或氧化性掺杂剂与有机物质的混合区域。
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CN114075112A (zh) * 2020-08-14 2022-02-22 广州华睿光电材料有限公司 芴类化合物及其应用
CN114075112B (zh) * 2020-08-14 2023-12-01 广州华睿光电材料有限公司 芴类化合物及其应用
CN112939788A (zh) * 2021-03-01 2021-06-11 浙江虹舞科技有限公司 一种金刚烷胺类化合物及其应用以及包含该化合物的有机电致发光器件

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