CN103819455A - 新有机电致发光化合物和使用该化合物的有机电致发光设备 - Google Patents

新有机电致发光化合物和使用该化合物的有机电致发光设备 Download PDF

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CN103819455A
CN103819455A CN201410097500.1A CN201410097500A CN103819455A CN 103819455 A CN103819455 A CN 103819455A CN 201410097500 A CN201410097500 A CN 201410097500A CN 103819455 A CN103819455 A CN 103819455A
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alkyl
aryl
organic electroluminescent
organic
compound
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CN103819455B (zh
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李秀镛
金荣佶
赵英俊
权赫柱
金奉玉
金圣珉
尹勝洙
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Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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Abstract

本发明提供了新的有机电致发光化合物以及使用该化合物的有机电致发光设备。当用作OLED设备的有机电致发光材料的基质材料时，本文所述的有机电致发光化合物相比现有基质材料具有良好的发光效率和优异的寿命性质。因此，它们可用于制造具有良好工作寿命的OLED。

Description

新有机电致发光化合物和使用该化合物的有机电致发光设备
本发明专利申请是国际申请号为PCT/KR2010/004699，国际申请日为2010年7月19日，进入中国国家阶段的申请号为201080039344.3，名称为“新有机电致发光化合物和使用该化合物的有机电致发光设备”的发明专利申请的分案申请。
技术领域
本发明涉及新的有机电致发光化合物以及使用该化合物的有机电致发光设备，更具体地，涉及一种用作电致发光材料的有机电致发光化合物以及使用该化合物作为基质的有机电致发光设备。
背景技术
确定OLED发光效率的最重要因素是电致发光材料。目前，荧光材料广泛用作电致发光材料。但是，当考虑电致发光机理时磷光材料是更好的。理论上，磷光材料可将发光效率提高4倍（4-fold）。到目前为止，铱(III)络合物基磷光材料是众所周知的。这些材料如(acac)Ir(btp)2、Ir(ppy)3和Firpic已知分别用于红色、绿色和蓝色。目前，正在对磷光材料进行许多研究，特别是在日本、欧洲和美国。
Figure BDA0000477239660000011
目前，CBP最广泛用作磷光材料的基质材料。已经报道了使用包含BCP、BAlq等的空穴阻挡层的高效OLED。先锋公司（日本）等已经报道了使用BAlq衍生物作为基质的高性能OLED。
Figure BDA0000477239660000021
尽管这些材料提供了良好的电致发光特性，但是它们具有一些缺陷，如在真空高温沉积加工时会发生分解，这是因为它们具有低的玻璃化转变温度和差的热稳定性。因为OLED的功率效率（power efficiency）是由(π/电压)×电流效率确定的，所以功率效率与电压成反比。需要高的功率效率来降低OLED的功率消耗。实际上，使用磷光材料的OLED提供比使用荧光材料的OLED更好的电流效率（cd/A）。但是，当现有材料例如BAlq、CBP等用作磷光材料的基质时，相比使用荧光材料的OLED在功率效率（lm/W）方面没有明显优势，这是因为驱动电压较高。
另外，OLED设备并不具有令人满意的工作寿命。因此，需要开发更稳定、更高性能的基质材料。
发明内容
技术问题
通过大量的努力以克服现有技术中的上述问题，本发明的发明人开发了新的有机电致发光化合物，它能够实现具有优异发光效率和显著提高的寿命性质的有机电致发光设备。
本发明的目的在于提供相对于常规基质或掺杂剂材料具有更好发光效率和设备寿命并具有适当的颜色坐标的具有骨架的有机电致发光化合物，同时克服了上述问题。
技术方案
提供了一种化学式1和6表示的新有机电致发光化合物以及使用该化合物的有机电致发光设备。因为本发明的有机电致发光化合物相比现有基质材料具有良好的发光效率和优异的寿命性质，所以它可用于制造具有非常好工作寿命的OLED设备。
其中：
X和Y独立地表示N(R1)、C(R2)(R3)或Si(R4)(R5)，条件在于X和Y的至少一个是N(R1)，且其余的是C(R2)(R3)或Si(R4)(R5)；
Z1到Z8独立地表示C(R6)或N，其中R6可相互不同，且相邻的R6可互相连接成环；
R1到R5独立地表示(C1-C30)烷基、(C3-C30)环烷基、5-到7-元杂环烷基、(C2-C30)烯基、(C2-C30)炔基、(C6-C30)芳基或(C3-C30)杂芳基；
R和R6独立地表示氢、(C1-C30)烷基、卤素、氰基、(C3-C30)环烷基、5-到7-元杂环烷基、(C2-C30)烯基、(C2-C30)炔基、(C6-C30)芳基、(C3-C30)杂芳基、单-或二(C1-C30)烷基氨基、单-或二(C6-C30)芳基氨基、RaRbRcSi-[其中，Ra、Rb和Rc独立地表示(C1-C30)烷基或(C6-C30)芳基],RdY-[其中Y表示O或S，且Rd表示(C1-C30)烷基或(C6-C30)芳基]，单-或二(C6-C30)芳基硼烷基、单-或二(C1-C60)烷基硼烷基、硝基或羟基；
R和R1到R6的烷基、环烷基、杂环烷基、烯基、炔基、芳基、杂芳基、烷基氨基、芳基氨基、芳基硼烷基或烷基硼烷以及Ra、Rb、Rc和Rd的烷基或芳基还可由一个或多个取代基取代，所述取代基选自(C1-C30)烷基、卤素、氰基、(C3-C30)环烷基、5-到7-元杂环烷基、(C2-C30)烯基、(C2-C30)炔基、(C6-C30)芳基、(C1-C30)烷氧基、(C6-C30)芳氧基、由P(=O)ReRf取代的(C6-C30)芳基[其中Re和Rf独立地表示(C1-C30)烷基或(C6-C30)芳基]、(C3-C30)杂芳基、(C6-C30)芳基取代的(C3-C30)杂芳基、(C1-C30)烷基取代的(C3-C30)杂芳基、(C6-C30)芳基(C1-C30)烷基、(C6-C30)芳硫基(arylthio)、(C1-C30)烷硫基(alkylthio)、单-或二(C1-C30)烷基氨基、单-或二(C6-C30)芳基氨基、三(C1-C30)烷基甲硅烷基、二(C1-C30)烷基(C6-C30)芳基甲硅烷基、三(C6-C30)芳基甲硅烷基、单-或二(C6-C30)芳基硼烷基、单-或二(C1-C30)烷基硼烷基、硝基和羟基；以及
所述杂环烷基或杂芳基可包含一个或多个选自B,N,O,S,P(=O),Si和P的杂原子。
在本发明中，(C1-C30)烷基、三(C1-C30)烷基甲硅烷基、二(C1-C30)烷基(C6-C30)芳基甲硅烷基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷氧基、(C1-C30)烷硫基等的烷基部分可具有_1-20个碳原子，优选1-10个碳原子。(C6-C30)芳基,二(C1-C30)烷基(C6-C30)芳基甲硅烷基,三(C6-C30)芳基甲硅烷基,(C6-C30)芳基(C1-C30)烷基,(C6-C30)芳氧基、(C6-C30)芳硫基等的芳基部分可具有6-20个碳原子，优选6-12个碳原子。“(C3-C30)杂芳基”的杂芳基可具有4-20个碳原子，更优选4-12个碳原子。“(C3-C30)环烷基”的环烷基可具有3-20个碳原子，更优选3-7个碳原子。“(C2-C30)烯基或炔基”的烯基或炔基可具有2-20个碳原子，更优选2-10个碳原子。
在本发明中，烷基包括直链和支链饱和单价烃自由基，其仅由碳原子和氢原子或其组合形成。所述环烷基包括烃基如金刚烷基，或者二环烷基或多环基以及单环基。
在本发明中，芳基表示通过从芳香烃除去一个氢原子得到的有机基团，可包括4-到7-元、优选5-或6-元的单环或稠环，包括通过单键连接的多个芳基。具体例子包括苯基、萘基、联苯基（biphenyl）、蒽基、茚基、芴基、菲基（phenanthryl）、苯并[9,10]菲基（triphenylenyl）、芘基、
Figure BDA0000477239660000051
基（perylenyl）、
Figure BDA0000477239660000052
基（chrysenyl）、并四苯基（naphthacenyl）、荧蒽基（fluoranthenyl）等，但不限于此。所述萘基包括1-萘基和2-萘基，所述蒽基包括1-蒽基、2-蒽基和9-蒽基，所述芴基包括1-芴基、2-芴基、3-芴基、4-芴基和9-芴基。在本发明中，“杂芳基”表示包含1-4个选自B,N,O,S,P(=O),Si和P的杂原子作为芳环骨架原子、其他芳环骨架原子为碳的芳基。它可以是5-或6-元单环杂芳基或与苯环缩合得到的多环杂芳基，且可部分饱和。另外，所述杂芳基包括通过单键连接的超过一个杂芳基。所述杂芳基包括二价芳基，其中环中的杂原子可被氧化或季铵化形成例如N-氧化物或季铵盐。具体的例子包括单环杂芳基例如呋喃基、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 BDA0000477239660000055
唑基、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；多环杂芳基例如苯并呋喃基（benzofuranyl）、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
Figure BDA0000477239660000054
唑基、苯并
Figure BDA0000477239660000053
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、喹喔啉基（quinoxalinyl）、咔唑基、菲啶基（phenanthridinyl）、苯并间二氧杂环戊烯基（benzodioxolyl）等；及其N-氧化物（例如吡啶基N-氧化物、喹啉基N-氧化物等）；及其季铵盐等，但并不限于此。
而且，本发明的有机电致发光化合物的例子可参见具有下述结构的化合物。
Figure BDA0000477239660000071
Figure BDA0000477239660000081
其中：
Y表示C(R2)(R3)或Si(R4)(R5)；且R和R1到R5与化学式1-6所定义的相同。而且，本发明的有机电致发光化合物的例子可参见具有下述结构的化合物。
Figure BDA0000477239660000091
其中：
Y表示C(R2)(R3)或Si(R4)(R5)；且R和R1到R5与化学式1-6所定义的相同。
另外，本发明的有机电致发光化合物的例子可参见具有下述结构的化合物。
Figure BDA0000477239660000101
其中：
R和R1到R6与化学式1-6中的定义相同。
具体地，R和R2到R5独立地选自氢、卤素、烷基（如甲基、乙基、丙基、丁基、戊基、己基、乙基己基、庚基和辛基）以及芳基（如苯基、萘基、芴基、联苯基、菲基(phenanthryl)、三联苯基（terphenyl）、芘基（pyrenyl）、
Figure BDA0000477239660000103
基（perylenyl）、螺二芴基、荧蒽基（fluoranthenyl）、基（chrysenyl）和苯并[9,10]菲基（triphenylenyl），但不限于此。
具体地，R1和R6独立地表示苯基、1-萘基、2-萘基或选自下述结构的取代基，但不限于此。
Figure BDA0000477239660000111
Figure BDA0000477239660000121
Figure BDA0000477239660000131
提供了一种本发明的有机电致发光设备，它包括第一电极；第二电极；插入所述第一电极和第二电极之间的一层或多层有机层，所述有机层包括化学式1-6表示的一种或多种有机电致发光化合物。
在本发明的有机电致发光设备中，所述有机层可包括电致发光层，所述电致发光层包括一种或多种磷光掺杂剂以及一种或多种化学式1-6所示的有机电致发光化合物作为电致发光基质。所述电致发光掺杂剂并没有具体限制。
在本发明的有机电致发光设备中，可包含选自化学式1-6的一种或多种有机电致发光化合物，还可同时包含选自芳胺化合物或苯乙烯基芳胺化合物的一种或多种化合物。
除了选自化学式1-6的一种或多种有机电致发光化合物外，本发明的有机层还可包括一种或多种选自元素周期表第1族、第2族的有机金属、第四周期和第五周期过渡金属、镧系金属和d-过渡元素的金属或络合物。所述有机层可包括电致发光层和电荷产生层。
除了所述有机电致发光化合物外，所述有机层可同时包括一层或多层发蓝光、红光或绿光的有机电致发光层，以形成发白光的有机电致发光设备。
有益的效果
因为本发明的有机电致发光化合物相比现有基质材料具有良好的发光效率和优异的寿命性质，所以它可用于制造具有非常好工作寿命且消耗更少电力的OLED设备，因为它具有改善的功率效率。
具体实施方式
为了便于理解，本发明的有机电致发光化合物及其制备方法和使用该化合物的设备基于下述代表性化合物进行详细说明。但是，这些实施例仅仅是为了阐述的目的，而不是为了限制本发明的范围。
制备实施例
[制备例1]制备化合物A
Figure BDA0000477239660000141
制备化合物A-1
混合1-溴硝基苯(16g,74.25mmol)、9,9-二甲基-9H-芴-2-基硼酸(23g,96.60mmol)、Pd(PPh3)4(4.2g,3.63mmol)、2M K2CO3水溶液(111mL)、EtOH(100mL)和甲苯(200mL)，并加热到120℃回流3小时。反应完成后，用蒸馏水洗涤混合物。用EA萃取并用MgSO4干燥有机层后，使用旋转蒸发器除去溶剂。剩余物通过柱色谱纯化得到化合物(A-1)(22g,95%)。
制备化合物A-2
混合化合物A-1(24g,76.10mmol)、亚磷酸三乙酯(200mL)和1,2-二氯苯(200mL)，加热到180℃，并搅拌12小时。当反应完成时，使用蒸馏装置除去未反应的亚磷酸三乙酯和1,2-二氯苯，且用蒸馏水洗涤剩余物。用EA萃取并用MgSO4干燥有机层后，使用旋转蒸发器除去溶剂。剩余物通过柱色谱纯化得到化合物(A-2)(7g,33%)。
制备化合物A-3
DMF(10mL)加入到NaH(60%,1.15g,28.90mmol)中，并于室温搅拌。将化合物A-2(6.3g,28.98mmol)溶解在DMF(50mL)中后，所述混合物缓慢加入到包含NaH的反应容器中。于室温搅拌1小时后，向其中缓慢加入2,4-二氯嘧啶（dichloropyrimidin）(4.9g,33.34mmol)，并溶解在50mL的DMF中。反应5小时后，加入H2O(50mL)。形成的固体过滤，溶解在MC中，并萃取后，用MgSO4干燥有机层。通过旋转蒸发器除去溶剂。剩余物通过柱色谱纯化得到化合物(A-3)(4g,45%)。
制备化合物A-4
1,3-二溴苯(20g,84.77mmol)加入到反应容器中，并在真空状态中形成氮气气氛。加入四氢呋喃(500mL)后,所述混合物于-78℃搅拌10分钟。缓慢加入N-BuLi(2.5M)(33.9mL,84.77mmol)后，所述混合物于-78℃搅拌1小时。氯三苯基硅烷(29.9g,107.72mmol)溶解在THF(100mL)中，并缓慢加入其中。于室温搅拌12小时后，完成反应且用蒸馏水洗涤所述混合物。用EA萃取并用MgSO4干燥有机层后，使用旋转蒸发器除去溶剂。从MC和MeOH重结晶得到化合物A-4(62g,63%)。
制备化合物A-5
化合物A-4(22.5g,0.10mol)加入到反应容器中，并在真空状态中形成氮气气氛。加入四氢呋喃(1.3L)后,所述混合物于-78℃搅拌10分钟。将n-BuLi(2.5M)(48.6mL,0.12mol)缓慢加入其中，并于-78℃搅拌1小时。缓慢加入硼酸三乙酯(18mL,0.16mmol)。于室温搅拌12小时后，反应完成且用蒸馏水洗涤所述混合物。用EA萃取并用MgSO4干燥有机层后，使用旋转蒸发器除去溶剂。剩余物通过柱色谱纯化得到化合物(A-5)(10g,45%)。
制备化合物A
将化合物A-3(2.5g,6.31mmol)、化合物A-5(3.6g,9.47mmol)、Pd(PPh3)4(730mg,0.63mmol)、K2CO3(2M)(19mL)、EtOH(19mL)和甲苯(40mL)混合，并加热到120℃回流3小时。反应完成时，用蒸馏水洗涤混合物。用EA萃取并用MgSO4干燥有机层后，使用旋转蒸发器除去溶剂。剩余物通过柱色谱纯化得到化合物A(3.8g,88%)。
[制备例2]制备化合物B
Figure BDA0000477239660000161
化合物B-2的制备
化合物B-1(50.0g,179mmol)溶解在DMF(200mL)中，且向其中加入铜粉末(27.0g,424mmol)。于125℃搅拌该混合物3小时。于室温冷却所述反应混合物，过滤并除去沉淀后干燥。用MeOH(500mL)洗涤得到化合物B-2(27.1g,88%)。
化合物B-3的制备
化合物B-2(15g,37.3mmol)溶解在乙醇(200mL)中，且向其中加入32％（w/w）HCl水溶液（120mL）。于室温在10分钟内分批加入锡粉末(17.6g,147mmol)，于100℃搅拌2小时。在室温冷却后，反应混合物加入到冰水中，使用20％（w/w）NaOH水溶液（150mL）变成碱性。用二乙基醚萃取，用盐水（bryn）洗涤并干燥。从乙醇重结晶得到化合物B-3(9.2g,72%)。
化合物B-4的制备
将17%(w/w)HCl水溶液(85mL)加入到0℃的包含化合物（B-3）(8.5g,25mmol)的圆底烧瓶中，且向其中加入NaNO2水溶液[NaNO24.3g(62mmol)+水(15mL)]。混合物搅拌30分钟，且向其中加入KI水溶液[KI41.5g(250_mmol)+水(15mL)]。所述混合物于室温搅拌1小时，并于60℃搅拌3小时。用饱和KOH溶液中和、用乙酸乙酯萃取且用饱和Na2SO3洗涤后，剩余物通过柱色谱纯化得到化合物B-4(4g,29%)。
化合物B-5的制备
包含化合物B-4(4g,7.1mmol)的圆底烧瓶A用氩气填充，并向其中加入30mL的THF。混合物冷却到-78℃。缓慢加入n-BuLi(在己烷中2.5M,6.2mL,15.6mmol)并搅拌1小时。向其中加入二氯二甲基硅烷(2.0g,15.6mmol)，并缓慢加热到室温回流12小时。用EA萃取并用水洗涤后，干燥所得有机层，并通过二氧化硅柱色谱纯化得到化合物B-5(2g,76%)。
化合物B-6的制备
包含化合物B-5(2g,5.43mmol)的圆底烧瓶用氩气填充，并在向其中加入THF(25mL)后冷却到-78℃。缓慢加入n-BuLi(在己烷中2.5M,2.2mL,5.43mmol)并搅拌1小时。向其中加入1M HCl(20mL)，并搅拌2小时。当混合物充分搅拌时用EA萃取并用水洗涤，然后干燥所得有机层，并通过二氧化硅柱色谱纯化得到化合物B-6(1.5g,96%)。
化合物B-8的制备
包含化合物B-6(15g,51.9mmol)的圆底烧瓶用氩气填充，并在向其中加入THF(300mL)后冷却到-78℃。缓慢加入n-BuLi(在己烷中2.5M,20.8mL,51.9mmol)并搅拌1小时。向其中加入化合物B-7(335mg,62.3mmol)，并缓慢加热到室温回流12小时。用EA萃取并用水洗涤后，干燥所得有机层，并通过二氧化硅柱色谱纯化得到化合物B-8(12g,69%)。
化合物B-9的制备
向包含化合物B-8(12g,35.7mmol)的圆底烧瓶中加入2-溴硝基苯(8.65g,42.8mmol)和Pd(PPh3)4(1.24g,1.07mmol)，且用氩气填充圆底烧瓶。向其中加入甲苯(120mL)、乙醇(60mL)和2M K2CO3(60mL)，并回流搅拌4小时。在室温冷却、用EA萃取并用水洗涤后，干燥所得有机层，并通过二氧化硅柱色谱纯化得到化合物B-9(9.5g,80%)。
化合物B-10的制备
用氩气填充包含化合物B-9(9.5g,28.7mmol)的圆底烧瓶。向其中加入亚磷酸三乙酯(100mL)和1,2-二氯苯(500mL)，并回流搅拌12小时。在室温冷却、用EA萃取并用水洗涤后，干燥所得有机层，并通过二氧化硅柱色谱纯化得到化合物B-10(7.2g,84%)。
化合物B-13的制备
向包含化合物B-12(10g,67.1mmol)的圆底烧瓶中加入化合物B-11(9.8g,80.5mmol)和Pd(PPh3)4(2.33g,2.01mmol)，且用氩气填充圆底烧瓶。向其中加入甲苯(240mL)、乙醇(120mL)和2M K2CO3(120mL)，并回流搅拌4小时。在室温冷却、用EA萃取并用水洗涤后，干燥所得有机层，并通过二氧化硅柱色谱纯化得到化合物B-13(11g,86%)。
化合物B的制备
化合物B-10(3.0g,10.0mmol)溶解在DMF(200mL)中的混合物缓慢加入到包含NaH(288mg,12mmol)和DMF(100mL)的圆底烧瓶中，并搅拌1小时。化合物B-13(1.5g,10mmol)缓慢加入并溶解在DMF(200mL)中，并于室温搅拌12小时。
过滤反应混合物，用水和MeOH洗涤并干燥得到化合物B(2.1g,46%)。
[制备例3]制备化合物C
Figure BDA0000477239660000181
化合物C-1的制备
除了使用二氯二苯基硅烷代替二氯二甲基硅烷，以与制备例2中制备化合物B-5相同的方法用化合物B-4作为原料制备化合物C-1(1.7g,50%)。
化合物C的制备
以与制备例2中制备化合物B-6、B-8、B-9、B-10和B相同的方法用化合物C-1作为原料制备化合物C(347mg,55%)。
根据制备例1-3的方法制备有机电致发光化合物TA、TB和TC，表1-4列出了1H NMR和MS/FAB，它们是所制备有机电致发光化合物的取代形式。
表1
Figure BDA0000477239660000191
Figure BDA0000477239660000201
Figure BDA0000477239660000211
Figure BDA0000477239660000221
Figure BDA0000477239660000231
表2
Figure BDA0000477239660000232
Figure BDA0000477239660000241
Figure BDA0000477239660000251
表3
表4
Figure BDA0000477239660000282
Figure BDA0000477239660000291
[实施例1]使用本发明的有机电致发光化合物制备OLED设备
使用本发明的电致发光材料制造了OLED装置。首先，将由玻璃制成的用于OLED的透明电极ITO薄膜(15Ω/□)（购自三星康宁公司（Samsung-Corning））依次用三氯乙烯、丙酮、乙醇和蒸馏水进行超声清洗，并在使用之前储存在异丙醇中。然后，将ITO基片装在真空气相沉积设备的基片夹（folder）中，将4,4',4"-三(N,N-(2-萘基)-苯基氨基)三苯胺(2-TNATA)置于真空气相沉积设备的小室(cell)中，然后，排气，使室内真空度最高达到10-6托。
接着，通过向所述小室施加电流以蒸发2-TNATA，在ITO基材上形成60nm厚的空穴注入层。接着，向真空沉积设备的另一个小室中加入N,N'-二(α-萘基)-N,N'-二苯基-4,4'-二胺(NPB)，通过向所述小室施加电流蒸发NPB，以在所述空穴注入层上沉积20nm厚的空穴传输层。
如下述在所述空穴传输层上形成电致发光层。于10-6托真空升华的本发明化合物(例如化合物TC10-19)装入真空气相沉积设备的小室内作为基质材料，且电致发光掺杂剂(例如(piq)2Ir(acac)[二-(1-苯基异喹啉基)铱(III)乙酰丙酮酸])装入另一个小室内。以不同的速率蒸发两种材料，所以以4-10摩尔％在空穴传输层上形成30nm厚的电致发光层。
之后，气相沉积20nm厚的三(8-羟基喹啉)合-铝(III)(Alq)作为电子传输层，且气相沉积1-2nm厚的喹啉合锂（Liq）作为电子注入层。然后，采用另一个真空气相沉积设备，气相沉积150纳米厚的Al阴极，制造OLED。
[实施例2]使用本发明的有机电致发光化合物制备OLED设备
用与实施例1相同的方法制造OLED，不同的是本发明的化合物（例如化合物TC10-12）用作基质材料，在电致发光层上气相沉积5nm厚的二(2-甲基-8-喹啉合)(对苯基苯酚合)铝(III)(BAlq)作为空穴阻挡层。
[实施例3]使用本发明的有机电致发光化合物制备OLED设备
用与实施例1相同的方法制造OLED，不同的是本发明的化合物(例如化合物TC10-97)用作基质材料，且有机铱络合物(Ir(ppy)3[三(2-苯基吡啶)铱])用作电致发光掺杂剂。
[实施例4]使用本发明的有机电致发光化合物制备OLED设备
用与实施例3相同的方法制造OLED，不同的是本发明的化合物（例如化合物TC4-105）用作基质材料，在电致发光层上气相沉积5nm厚的二(2-甲基-8-喹啉合)(对苯基苯酚合)铝(III)(BAlq)作为空穴阻挡层。
[比较例1和2]使用常规电致发光材料制造OLED器件
用与实施例2和4相同的方法制造OLED，不同的是在真空气相沉积设备的另一个小室内使用4,4'-二(9H-咔唑-9-酮)联苯(CBP)代替本发明的有机电致发光化合物作为电致发光基质材料。
于1,000cd/m2的条件分别测量包含本发明有机电致发光化合物（实施例1-4）和常规电致发光化合物（比较例1和2）的OLED的发光效率，结果列在表5中。
Figure BDA0000477239660000311
如表5所示，本发明的有机电致发光化合物相比常规材料具有优异的性质。另外，使用本发明的有机电致发光化合物作为基质材料的发红光或绿光的设备具有优异的电致发光性质和降低了驱动电压，从而提高了功率效率且改善了功率消耗。

Claims (9)

1.化学式4表示的有机电致发光化合物：
化学式4
Figure FDA0000477239650000011
其中：
X和Y独立地表示N(R1)、C(R2)(R3)或Si(R4)(R5)，条件在于X和Y的至少一个是N(R1)，且其余的是C(R2)(R3)或Si(R4)(R5)；
Z1到Z8独立地表示C(R6)或N，其中R6可相互不同，且相邻的R6可互相连接成环；
R1到R5独立地表示(C1-C30)烷基、(C3-C30)环烷基、5-到7-元杂环烷基、(C2-C30)烯基、(C2-C30)炔基、(C6-C30)芳基或(C3-C30)杂芳基；
R和R6独立地表示氢、(C1-C30)烷基、卤素、氰基、(C3-C30)环烷基、5-到7-元杂环烷基、(C2-C30)烯基、(C2-C30)炔基、(C6-C30)芳基、(C3-C30)杂芳基、单-或二(C1-C30)烷基氨基、单-或二(C6-C30)芳基氨基、RaRbRcSi-[其中，Ra、Rb和Rc独立地表示(C1-C30)烷基或(C6-C30)芳基],RdY-[其中Y表示O或S，且Rd表示(C1-C30)烷基或(C6-C30)芳基]，单-或二(C6-C30)芳基硼烷基、单-或二(C1-C60)烷基硼烷基、硝基或羟基；
R和R1到R6的烷基、环烷基、杂环烷基、烯基、炔基、芳基、杂芳基、烷基氨基、芳基氨基、芳基硼烷基或烷基硼烷基以及Ra、Rb、Rc和Rd的烷基或芳基还可由一个或多个取代基取代，所述取代基选自(C1-C30)烷基、卤素、氰基、(C3-C30)环烷基、5-到7-元杂环烷基、(C2-C30)烯基、(C2-C30)炔基、(C6-C30)芳基、(C1-C30)烷氧基、(C6-C30)芳氧基、由P(=O)ReRf取代的(C6-C30)芳基[其中Re和Rf独立地表示(C1-C30)烷基或(C6-C30)芳基]、(C3-C30)杂芳基、(C6-C30)芳基取代的(C3-C30)杂芳基、(C1-C30)烷基取代的(C3-C30)杂芳基、(C6-C30)芳基(C1-C30)烷基、(C6-C30)芳硫基、(C1-C30)烷硫基、单-或二(C1-C30)烷基氨基、单-或二(C6-C30)芳基氨基、三(C1-C30)烷基甲硅烷基、二(C1-C30)烷基(C6-C30)芳基甲硅烷基、三(C6-C30)芳基甲硅烷基、单-或二(C6-C30)芳基硼烷基、单-或二(C1-C30)烷基硼烷基、硝基和羟基；以及
所述杂环烷基或杂芳基可包含一个或多个选自B,N,O,S,P(=O),Si和P的杂原子。
2.如权利要求1所述的有机电致发光化合物，其特征在于，所述化合物选自下述化合物：
Figure FDA0000477239650000021
Figure FDA0000477239650000031
其中：
Y表示C(R2)(R3)或Si(R4)(R5)；且R和R1到R5与权利要求1所定义的相同。
3.如权利要求1所述的有机电致发光化合物，其特征在于，所述化合物选自下述化合物：
Figure FDA0000477239650000032
其中：
R和R1到R6与权利要求1中的定义相同。
4.一种有机电致发光器件，所述器件包括权利要求1-3中任一项所述的有机电致发光化合物。
5.如权利要求4所述的有机电致发光器件，所述器件包括：第一电极；第二电极；以及插入所述第一电极和第二电极之间的一层或多层有机层，其中所述有机层包含一种或多种权利要求1-3中任一项所述的有机电致发光化合物，和一种或多种磷光掺杂剂。
6.如权利要求5所述的有机电致发光设备，其特征在于，所述有机层包含选自芳胺化合物和苯乙烯基芳胺化合物的一种或多种胺化合物。
7.如权利要求5所述的有机电致发光器件，其特征在于，所述有机层还包含选自元素周期表中第1族、第2族的有机金属、第四周期和第五周期过渡金属、镧系金属和d-过渡元素的一种或多种金属或络合物。
8.如权利要求5所述的有机电致发光器件，其特征在于，所述有机层包括电致发光层和电荷产生层。
9.如权利要求5所述的有机电致发光设备，其特征在于，所述有机电致发光设备是发射白光的有机电致发光设备，所述有机层还包括一层或多层发射蓝光、红光或绿光的有机电致发光层。
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