CN115175973A - 有机发光化合物及包含其的有机发光器件 - Google Patents
有机发光化合物及包含其的有机发光器件 Download PDFInfo
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- CN115175973A CN115175973A CN202080097653.XA CN202080097653A CN115175973A CN 115175973 A CN115175973 A CN 115175973A CN 202080097653 A CN202080097653 A CN 202080097653A CN 115175973 A CN115175973 A CN 115175973A
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 238000004528 spin coating Methods 0.000 description 1
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- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
本发明涉及一种有机发光化合物,其用于有机发光器件中具备的光效率改善层,使用该化合物的有机发光器件可以在低电压下驱动更改进的器件,并且可以通过改善的光提取效率实现优异的发光效率,因此可以有效地用于各种显示器件。
Description
技术领域
本发明涉及一种有机发光化合物,更具体地,涉及一种以用作有机发光器件中具备的光效率改善层(覆盖层(Capping layer))的材料为特征的有机发光化合物,以及通过使用该有机发光化合物来实现器件的低电压驱动及优异的发光效率等发光特性显著提高的有机发光器件。
背景技术
有机发光器件不仅可以在透明基板上形成器件,而且,与等离子体平板显示屏(Plasma Display Panel)或无机电致发光(EL)显示器相比,具有能够在10V以下的低电压下驱动、功耗较低、色彩感突出等优点,还可以显示绿、蓝、红三种颜色,近来作为新一代显示器件备受关注。
然而,为了使这种有机发光器件发挥上述特征,形成器件内有机层的物质,如空穴注入物质、空穴传输物质、发光物质、电子传输物质、电子注入物质等必须先得到稳定且高效的材料支撑,但目前还未充分开发出用于有机发光器件的稳定、高效的有机层材料。
因此,为了实现更稳定的有机发光器件和器件的高效率、长寿命、大型化等,需要在效率及寿命特性方面得到进一步的改善,尤其,迫切需要开发一种用于形成有机发光器件的各有机层的材料。
对此,针对上述有机发光器件结构中的空穴传输层材料,近来关于提高现有有机材料导电率(mobility)的研究非常活跃。
此外,除了关于通过改变各有机层材料的性能来提高有机发光器件特性的研究以外,通过优化阳极(anode)和阴极(cathode)之间的光学厚度来提高色纯度及发光效率的技术被视为提高器件性能的重要因素之一,这种方法的一个示例是在电极上使用覆盖层(capping layer)来提高光效率并获得优异的色纯度。
发明内容
技术问题
因此,本发明的目的在于,提供新型有机发光化合物以及包含其的有机发光器件,可以通过将上述有机发光化合物用于有机发光器件中具备的光效率改善层来实现器件的低电压驱动及发光效率高等优异的发光特性。
技术方案
为了解决上述问题,本发明提供选自由下述化学式Ⅰ表示的化合物中的任一种有机发光化合物。
化学式Ⅰ
关于上述化学式Ⅰ的特征结构及A1至A2将在下文中进行说明。
并且,本发明还提供一种有机发光器件,包含第一电极、第二电极及置于上述第一电极与第二电极之间的至少一层有机层,其特征在于,还包含光效率改善层(覆盖层(Capping layer)),其形成于上述第一电极和第二电极的上部或下部中与上述有机层相对的至少一侧,并且上述光效率改善层包含由上述化学式Ⅰ表示的有机发光化合物。
根据本发明一实施例,其特征在于,上述光效率改善层具有50nm至150nm的厚度,在450nm的波长下具有2.10以上的折射率值。
发明的效果
当本发明的有机发光化合物用作有机发光器件中具备的光效率改善层的材料时,可以实现器件的低电压驱动及优异的发光效率等发光特性,因此可以有效地用于各种显示器件。
附图说明
图1为示出本发明的有机发光化合物的结构的代表图。
最佳实施方式
以下,将对本发明进行更加详细的说明。
本发明涉及由下述化学式Ⅰ表示的有机发光化合物,可以通过将其用于有机发光器件中具备的光效率改善层来实现器件的低电压驱动及优异的发光效率等发光特性。
化学式Ⅰ
在上述化学式Ⅰ中,其特征在于,A1至A2彼此相同或不同,分别独立地由下述结构式1表示。
像这样,本发明的化合物的特征在于,在结构上由化学式Ⅰ表示的骨架结构中导入下述结构式1,由此实现适合光效率改善层的材料,并且可以实现具有低电压驱动及优异的发光效率等发光特性的有机发光器件。
结构式1
在上述结构式1中,X为O或S。
R1至R4彼此相同或不同,分别独立地选自氢、氘、卤素基、氰基、取代或未取代的碳原子数1至20的烷基、取代或未取代的碳原子数2至20的烯基、取代或未取代的碳原子数3至20的环烷基、取代或未取代的碳原子数1至20的烷氧基、取代或未取代的碳原子数1至20的卤代烷基、取代或未取代的碳原子数1至20的卤代烷氧基、取代或未取代的碳原子数6至30的芳基及取代或未取代的碳原子数3至30的杂芳基中。
上述R1至R4可以互相键合或与相邻的取代基连接并形成至少一个脂环族、芳香族单环或多环,所形成的上述脂环族、芳香族单环或多环的碳原子能够被选自氮原子(N)、硫原子(S)及氧原子(O)中的至少一种杂原子取代。
由此,上述结构式1可以为选自由下述结构式2至结构式6表示的结构式中的任一种。
在上述结构式2至结构式6中,X为O或S。
Y1至Y4彼此相同或不同,分别独立地为N或CR5。
R1至R4及上述R5彼此相同或不同,分别独立地选自氢、氘、卤素基、氰基、取代或未取代的碳原子数1至20的烷基、取代或未取代的碳原子数2至20的烯基、取代或未取代的碳原子数3至20的环烷基、取代或未取代的碳原子数1至20的烷氧基、取代或未取代的碳原子数1至20的卤代烷基、取代或未取代的碳原子数1至20的卤代烷氧基、取代或未取代的碳原子数6至30的芳基及取代或未取代的碳原子数3至30的杂芳基中。
另一方面,在上述R1至R5的定义中,取代或未取代是指被选自由氢、氘、卤素基、氰基、硝基、羟基、甲硅烷基、烷基、环烷基、烷氧基、烯基、芳基及杂环基组成的组中的1种或2种以上的取代基取代,或被由上述取代基中2种以上的取代基连接的取代基取代,或不具有任何取代基。
具体举例来说,被取代的亚芳基是指被其他取代基取代的苯基、联苯基、萘基、芴基、芘基、菲基、苝基、并四苯基、蒽基等。
并且,被取代的亚杂芳基是指被其他取代基取代的吡啶基、噻吩基、三嗪基、喹啉基、菲咯啉基、咪唑基、噻唑基、恶唑基、咔唑基及它们的稠合杂环基,例如苯并喹啉基、苯并咪唑基、苯并恶唑基、苯并噻唑基、苯并咔唑基、二苯并噻吩基、二苯并呋喃基等。
关于本发明的上述取代基的示例将在下文中进行详细说明,但本发明不限于此。
在本发明中,上述烷基可以为直链或支链,碳原子数没有特别限制,但优选为1至20。具体示例有甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基丁基、1-乙基丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基丙基、1,1-二甲基丙基、异己基、2-甲基戊基、4-甲基己基、5-甲基己基等,但不限于此。
在本发明中,烷氧基可以为直链或支链。烷氧基的碳原子数没有特别限制,但优选为不产生空间位阻的范围,即1至20。具体地,可以为甲氧基、乙氧基、正丙氧基、异丙氧基、i-丙氧基、正丁氧基、异丁氧基、叔丁氧基、仲丁氧基、正戊氧基、新戊氧基、异戊氧基、正己氧基、3,3-二甲基丁氧基、2-乙基丁氧基、正辛氧基、正壬氧基、正癸氧基、苄氧基、对甲基苄氧基等,但不限于此。
在本发明中,芳基可以为单环或多环,碳原子数没有特别限制,但优选为6至30。单环芳基的示例有苯基、联苯基、三联苯基和茋基等,多环芳基的示例有萘基、蒽基、菲基、芘基、苝基、并四苯基、草屈基、芴基、苊基、三亚苯基、荧蒽(fluoranthrene)基等,但本发明的范围不限于这些示例。
在本发明中,杂芳基及杂环基是作为杂原子包含O、N或S的杂环基,碳原子数没有特别限制,但优选碳原子数为2至30,在本发明中,其具体示例有噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、恶唑基、恶二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、三唑基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并恶唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、二苯并呋喃基、菲咯啉基、噻唑基、异恶唑基、恶二唑基、噻二唑基、苯并噻唑基、吩噻嗪基、吩恶嗪基、吩噻嗪基等,但不限于此。
在本发明中,甲硅烷基具体有三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等,但不限于此。
作为本发明中使用的取代基的卤素基,具体示例有氟(F)、氯(Cl)、溴(Br)等。
由于其结构特异性,由上述化学式Ⅰ表示的本发明的有机发光化合物可以用作有机发光器件内的各种有机层,更具体地,可以用作有机层内的发光层、空穴传输层或光效率改善层的材料。
由化学式Ⅰ表示的本发明的有机发光化合物的优选具体例有下列化合物,但不限于此。
像这样,本发明的有机发光化合物可以利用发挥其固有特性的特征骨架及导入其中的具有固有特性的部分(moiety)来合成具有多种特性的有机发光化合物,最终,当将本发明的有机发光化合物应用于发光层、光效率改善层、空穴传输层、电子传输层、电子阻挡层、空穴阻挡层等各种有机层物质时,可以进一步提高器件的发光效率等发光特性。
并且,本发明的化合物可以按照常规有机发光器件的制备方法应用于器件。
本发明一实施例的有机发光器件可以具有包含第一电极、第二电极及置于它们之间的有机层的结构,并且除了将本发明的有机发光化合物用于器件的有机层以外,可以使用常规的器件制备方法及材料来制备。
本发明的有机发光器件的有机层可以为单层结构,也可以为层叠2层以上有机层的多层结构。例如,它可以具有包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、电子阻挡层、空穴阻挡层、光效率改善层(覆盖层)等的结构。但不限于此,也可以包括更少或更多的有机层。
并且,本发明一实施例的有机电致发光器件包括基板、第一电极(阳极)、有机层、第二电极(阴极)及光效率改善层,上述光效率改善层可以形成于第一电极的下部(底部发光(Bottom emission))或第二电极的上部(顶部发光(Top emission))。
形成于第二电极的上部(顶部发光)的方式会将发光层形成的光发射至阴极方向,随着发射至阴极方向的光穿过折射率较高的由本发明的化合物形成的光效率改善层(CPL),光的波长被放大,光效率也随之提升。并且,形成于第一电极的下部(底部发光)的方式也是按照同样的原理将本发明的化合物用于光效率改善层,从而提高有机电致器件的光效率。
关于本发明的有机发光器件的优选有机层结构将在以下实施例中进行更详细的说明。
并且,本发明的有机发光器件利用溅射(sputtering)或电子束蒸发(e-beamevaporation)等物理气相沉积(PVD,physical vapor deposition)法,通过在基板上沉积金属或具有导电性的金属氧化物或其合金来形成阳极,在其上形成包括空穴注入层、空穴传输层、发光层、电子传输层的有机层后,在其上沉积能够用作阴极的物质来制备。
除了上述方法以外,还可以通过在基板上依次沉积阴极物质、有机层、阳极物质来制备有机发光器件。上述有机层可以为包括空穴注入层、空穴传输层、发光层及电子传输层等的多层结构,但不限于此,也可以为单层结构。并且,除了物理气相沉积法以外,上述有机层也可以使用多种聚合物材料,采用溶剂法(solvent process),例如旋涂法、浸涂法、刮刀法、丝网印刷法、喷墨印刷法或热转印法等来制备成更少的层。
作为上述阳极物质,通常优选功函数大的材料,以使空穴可以顺利地注入有机层。本发明中可以使用的阳极物质的具体示例有钒、铬、铜、锌、金等金属或其合金,氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物,ZnO:Al或SnO2:Sb等金属与氧化物的组合,聚(3-甲基噻吩)、聚[3,4-(乙烯-1,2-二氧基)噻吩](PEDT)、聚吡咯及聚苯胺等导电聚合物等,但不限于此。
作为上述阴极物质,通常优选功函数小的材料,以使电子可以容易地注入到有机层。阴极物质的具体示例有镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡及铅等金属或其合金,LiF/Al或LiO2/Al等多层结构物质等,但不限于此。
作为空穴注入物质,是能够在低电压下很好地接收从阳极注入的空穴的物质,优选地,空穴注入物质的最高占据分子轨道(HOMO,highest occupiedmolecular orbital)应在阳极物质的功函数和周边有机层的最高占据分子轨道之间。空穴注入物质的具体示例有金属卟啉(porphyrine)、低聚噻吩、芳胺类有机物、六腈六氮杂苯并苯、喹吖啶酮(quinacridone)类有机物、苝(perylene)类有机物、蒽醌及聚苯胺和聚噻吩类导电聚合物等,但不限于此。
作为空穴传输物质,是能够接收从阳极或空穴注入层传输的空穴并转移到发光层的物质,适合的是对空穴的迁移性大的物质。具体示例有芳基胺类有机物、导电聚合物、以及同时具有共轭部分和非共轭部分的嵌段共聚物,但是使用本发明的有机发光化合物可以进一步提高器件的低电压驱动特性、发光效率及寿命特性。
作为发光物质,是能够通过分别接收从空穴传输层传输的空穴及从电子传输层传输的电子来发出可见光区域的光的物质,优选对荧光或磷光的量子效率良好的物质。具体示例有8-羟基-喹啉铝络合物(Alq3)、咔唑类化合物、二聚苯乙烯基(dimerized styryl)化合物、BAlq、10-羟基苯并喹啉-金属化合物、苯并恶唑、苯并噻唑及苯并咪唑类化合物、聚(对苯乙撑)(PPV)类聚合物、螺(spiro)化合物、聚芴、红荧烯等,但不限于此。
作为电子传输物质,是能够很好地接收从阴极注入的电子并转移到发光层的物质,优选对电子的迁移性大的物质。具体示例有8-羟基喹啉的Al络合物、包含Alq3的络合物、有机自由基化合物及羟基黄酮-金属络合物等,但不限于此。
根据所使用的材料,本发明的有机发光器件可以为前面发光型、背面发光型或双面发光型。
并且,本发明的有机发光化合物能够与应用于有机发光器件的类似的原理作用于包括有机太阳能电池、有机感光体、有机晶体管等的有机电子器件。
具体实施方式
以下,将通过优选实施例对本发明进行更详细地说明。但是,这些实施例只是为了更具体地说明本发明,本发明的范围不限于此,对本领域的普通技术人员显而易见的是,在本发明的范畴及技术思想范围内,可以对本发明进行各种变更和修改。
合成例1:合成化合物1
(1)制备例1:合成中间体1-1
在3,6-二溴咔唑(3,6-Dibromocarbazole)(10g,0.031mol)、2-(4-氟苯基)萘(2-(4-fluorophenyl)naphthalene)(8.2g,0.037mol)、碳酸铯(cesium carbonate)(15g,0.046mol)中加入500mL的N,N-二甲基甲酰胺(DMF),在150℃下回流搅拌反应15小时。反应结束后萃取,进行柱纯化,得到16.8g(收率70.8%)的中间体1-1。
(2)制备例2:合成化合物1
加入中间体1-1(10g,0.019mol)、苯并[d]恶唑-2-基硼酸(benzo[d]oxazol-2-ylboronic acid)(7.42g,0.046mol)、碳酸钾(potassium carbonate)(13.1g,0.095mol)、Pd(PPh3)4(1.10g,0.001mol)、100mL的甲苯(toluene)及30mL的H2O、30mL的乙醇(Ethanol)后,在95℃下回流搅拌反应6小时。反应结束后萃取,进行柱纯化,得到7.5g(收率65.5%)的化合物1。
LC/MS:m/z=603[(M)+]
合成例2:合成化合物7
(1)制备例1:合成化合物7
加入中间体1-1(10g,0.019mol)、6-氰基苯并[d]恶唑-2-基硼酸(6-cyanobenzo[d]oxazol-2-ylboronic acid)(8.56g,0.046mol)、碳酸钾(13.1g,0.095mol)、Pd(PPh3)4(1.10g,0.001mol)、100mL的甲苯及30mL的H2O、30mL的乙醇后,在95℃下回流搅拌反应6小时。反应结束后萃取,进行柱纯化,得到8.1g(收率65.3%)的化合物7。
LC/MS:m/z=653[(M)+]
合成例3:合成化合物16
(1)制备例1:合成中间体16-1
在2,7-二溴-9H-咔唑(2,7-Dibromo-9H-carbazole)(10g,0.031mol)、2-(4-氟苯基)萘(17.5g,0.037mol)、碳酸铯(15g,0.046mol)中加入500mL的DMF,在150℃下回流搅拌12小时。反应结束后萃取,进行柱纯化,得到16.8g(收率70.8%)的中间体16-1。
(2)制备例2:合成化合物16
在中间体16-1(10g,0.019mol)、6-乙基苯并[d]恶唑-2-基硼酸(6-ethylbenzo[d]oxazol-2-ylboronic acid)(8.7g,0.046mol)、碳酸铯(13.1g,0.095mol)中加入500mL的DMF,在150℃下回流搅拌12小时。反应结束后萃取,进行柱纯化,得到8.7g(收率69.5%)的化合物16。
LC/MS:m/z=659[(M)+]
合成例4:合成化合物27
(1)制备例1:合成化合物27
加入中间体1-1(10g,0.019mol)、5,6-二甲基苯并[d]噻唑-2-基硼酸(5,6-dimethylbenzo[d]thiazol-2-ylboronic acid)(9.4g,0.046mol)、碳酸钾(13.1g,0.095mol)、Pd(PPh3)4(1.10g,0.001mol)、100mL的甲苯及30mL的H2O、30mL的乙醇后,在95℃下回流搅拌反应6小时。反应结束后萃取,进行柱纯化,得到8.9g(收率67.8%)的化合物27。
LC/MS:m/z=691[(M)+]
合成例5:合成化合物38
(1)制备例1:合成化合物38
加入中间体16-1(10g,0.019mol)、苯并[d]噻唑-2-基硼酸(benzo[d]thiazol-2-ylboronic acid)(8.15g,0.046mol)、碳酸钾(13.1g,0.095mol)、Pd(PPh3)4(1.10g,0.001mol)、100mL的甲苯及30mL的H2O、30mL的乙醇后,在95℃下回流搅拌反应6小时。反应结束后萃取,进行柱纯化,得到8.4g(收率69.7%)的化合物38。
LC/MS:m/z=635[(M)+]
合成例6:合成化合物49
(1)制备例1:合成化合物49
加入中间体1-1(10g,0.019mol)、苯并[d]恶唑-2-基硼酸(3.71g,0.023mol)、碳酸钾(7.86g,0.057mol)、Pd(PPh3)4(1.10g,0.001mol)100mL的甲苯及30mL的H2O、30mL的乙醇后,在95℃下回流搅拌反应6小时。反应结束后萃取,进行柱纯化,得到7.3g(收率68.1%)的中间体49-1。
(2)制备例2:合成化合物49
加入中间体49-1(10g,0.018mol)、苯并[d]噻唑-2-基硼酸(3.8g,0.021mol)、碳酸钾(7.33g,0.053mol)、Pd(PPh3)4(1.02g,0.001mol)、100mL的甲苯及30mL的H2O、30mL的乙醇后,在95℃下回流搅拌反应6小时。反应结束后萃取,进行柱纯化,得到8.1g(收率73.9%)的化合物49。
LC/MS:m/z=619[(M)+]
实验例1:本发明的化合物的光学特性
在本发明的实验例中,清洗25mm×25mm大小的玻璃基板。之后,安装在真空室中,当基础压力达到1×10-6torr以上时,在玻璃基板上分别沉积本发明的化合物及对比化合物来测量光学特性。
(1)实施例1至8
将本发明的化合物1、3、9、26、27、38、46、49分别在玻璃基板上沉积100nm来测量折射率。
石英玻璃(Quartzglass)/有机物(100nm)
(2)除了使用CP1来代替本发明实施的化合物以外,以相同的方法制备对比例1的基板来测量光学特性。
(3)对如上制备的基板使用椭圆光度法(Ellipsometry,Elli-SE)来测量折射率,在450nm参考波长下的结果值如下表1所示。
表1
观察上述表1中示出的结果,可以确认本发明的化合物在450nm的波长下具有2.20以上的折射率值。因此,本发明的化合物具有比对比例1更高的折射率,更适合作为光效率改善层的材料,由此,当将本发明的化合物用于光效率改善层时,可以进一步提高器件的特性。
器件实施例(覆盖层)
在本发明的实施例中,阳极使用包含25mm×25mm×0.7mm的Ag的ITO玻璃基板进行图案化,使发光面积达到2mm×2mm大小后清洗。将图案化的ITO基板安装在真空室后,在1×10-6torr以上的工艺压力下,将有机物及金属沉积成如下结构。
器件实施例9至16
通过将本发明实施的化合物用于光效率改善层来制备具有如下器件结构的蓝色有机发光器件,测量包括发光效率在内的发光特性。
Ag/ITO/空穴注入层(HAT-CN,5nm)/空穴传输层(α-NPB,100nm)/电子阻挡层(TCTA,10nm)/发光层(20nm)/电子传输层(201:Liq,30nm)/LiF(1nm)/Mg:Ag(15nm)/光效率改善层(70nm)
为了在玻璃基板上的包含Ag的ITO透明电极中形成空穴注入层,将HAT-CN成膜至5nm的厚度,然后空穴传输层用α-NPB成膜至100nm的厚度。电子阻挡层用TCTA成膜至10nm的厚度。并且,发光层以BH1作为主体化合物,BD1作为掺杂剂化合物来共沉积至20nm的厚度。此外,电子传输层(以下化合物201掺杂50%Liq)以30nm及LiF为1nm的厚度成膜。接着,将Mg:Ag以1:9的比例成膜至15nm。然后,作为光效率改善层(覆盖层)的化合物,将本发明实施的化合物1、3、9、26、27、38、46、49成膜至70nm的厚度来制备有机发光器件。
器件对比例1
除了在上述实施例9至16的器件结构中,使用CP1作为光效率改善层的化合物来代替本发明的化合物以外,以相同的方法制备器件对比例1的有机发光器件。
器件对比例2
除了在上述实施例9至16的器件结构中,不使用光效率改善层以外,以相同的方法制备器件对比例2的有机发光器件。
器件对比例3
除了在上述实施例9至16的器件结构中,使用Alq3作为光效率改善层的化合物来代替本发明的化合物以外,以相同的方法制备器件对比例3的有机发光器件。
实验例2:器件实施例9至16的发光特性
对根据上述实施例制备的有机发光器件,使用光源计(Source meter,Model237,Keithley公司)及亮度计(PR-650,Photo Research公司)来测量驱动电压、电流效率及色坐标,以1000nit为基准的结果值如下表2所示。
表2
观察上述表2中示出的结果,可以确认当将具有高折射率值的本发明的化合物作为光效率改善层应用于器件时,与现有的器件(对比例1、2、3)相比,驱动电压降低,电流效率得到提高。
产业上的可利用性
当将本发明的有机发光化合物用作有机发光器件中具备的光效率改善层的材料时,可以实现器件的低电压驱动及优异的发光效率等发光特性,因此可以有效地用于各种显示器件。
Claims (9)
1.一种有机发光化合物,其特征在于,由下述化学式Ⅰ表示:
化学式Ⅰ:
在上述化学式Ⅰ中,A1至A2彼此相同或不同,分别独立地由下述结构式1表示:
结构式1:
在上述结构式1中,
X为O或S,
R1至R4彼此相同或不同,分别独立地选自氢、氘、卤素基、氰基、取代或未取代的碳原子数1至20的烷基、取代或未取代的碳原子数2至20的烯基、取代或未取代的碳原子数3至20的环烷基、取代或未取代的碳原子数1至20的烷氧基、取代或未取代的碳原子数1至20的卤代烷基、取代或未取代的碳原子数1至20的卤代烷氧基、取代或未取代的碳原子数6至30的芳基及取代或未取代的碳原子数3至30的杂芳基中,
上述R1至R4能够互相键合或与相邻的取代基连接并形成至少一个脂环族、芳香族单环或多环,所形成的上述脂环族、芳香族单环或多环的碳原子能够被选自氮原子N、硫原子S及氧原子O中的至少一种杂原子取代。
2.根据权利要求1所述的有机发光化合物,其特征在于,上述结构式1为选自由下述结构式2至结构式6表示的结构式中的任一种:
在上述结构式2至结构式6中,
X为O或S,
Y1至Y4彼此相同或不同,分别独立地为N或CR5,
R1至R4及上述R5彼此相同或不同,分别独立地选自氢、氘、卤素基、氰基、取代或未取代的碳原子数1至20的烷基、取代或未取代的碳原子数2至20的烯基、取代或未取代的碳原子数3至20的环烷基、取代或未取代的碳原子数1至20的烷氧基、取代或未取代的碳原子数1至20的卤代烷基、取代或未取代的碳原子数1至20的卤代烷氧基、取代或未取代的碳原子数6至30的芳基及取代或未取代的碳原子数3至30的杂芳基中。
3.根据权利要求1或2所述的有机发光化合物,其特征在于,在上述R1至R5的定义中,“取代或未取代”是指被选自由氘、卤素基、氰基、硝基、羟基、甲硅烷基、烷基、环烷基、烷氧基、烯基、芳基及杂环基组成的组中的1种或2种以上的取代基取代,或被由上述取代基中2种以上的取代基连接的取代基取代,或不具有任何取代基。
5.一种有机发光器件,包含第一电极、第二电极及置于上述第一电极与第二电极之间的至少一层有机层,其特征在于,上述有机层中的至少一层包含权利要求1所述的化学式Ⅰ的有机发光化合物。
6.根据权利要求5所述的有机发光器件,其特征在于,
上述有机层包含选自空穴注入层、空穴传输层、同时执行空穴注入和空穴传输功能的层、电子传输层、电子注入层、同时执行电子传输和电子注入功能的层、电子阻挡层、空穴阻挡层及发光层中的至少一层,
上述各层中的至少一层包含由上述化学式Ⅰ表示的有机发光化合物。
7.根据权利要求5所述的有机发光器件,其特征在于,
还包含光效率改善层,其形成于上述第一电极和第二电极的上部或下部中与上述有机层相对的至少一侧,
上述光效率改善层包含由上述化学式Ⅰ表示的有机发光化合物。
8.根据权利要求7所述的有机发光器件,其特征在于,上述光效率改善层形成于上述第一电极的下部或上述第二电极的上部中的至少一处。
9.根据权利要求7所述的有机发光器件,其特征在于,上述光效率改善层具有50nm至150nm的厚度,在450nm的波长下具有2.10以上的折射率值。
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