CN110790754A - 可产生发光激基复合物的有机发光器件 - Google Patents
可产生发光激基复合物的有机发光器件 Download PDFInfo
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- CN110790754A CN110790754A CN201810873303.2A CN201810873303A CN110790754A CN 110790754 A CN110790754 A CN 110790754A CN 201810873303 A CN201810873303 A CN 201810873303A CN 110790754 A CN110790754 A CN 110790754A
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- emitting device
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- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 28
- 150000003918 triazines Chemical class 0.000 claims abstract description 24
- -1 nitro, carbonyl Chemical group 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000002019 doping agent Substances 0.000 claims description 14
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
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- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
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- 125000005842 heteroatom Chemical group 0.000 claims description 5
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005264 aryl amine group Chemical group 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 3
- 125000005362 aryl sulfone group Chemical group 0.000 claims description 3
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- 239000010931 gold Substances 0.000 claims description 3
- NDBCGHNTWCYIIU-UHFFFAOYSA-N iridium(3+);1-phenylisoquinoline Chemical group [Ir+3].[C-]1=CC=CC=C1C1=NC=CC2=CC=CC=C12.[C-]1=CC=CC=C1C1=NC=CC2=CC=CC=C12.[C-]1=CC=CC=C1C1=NC=CC2=CC=CC=C12 NDBCGHNTWCYIIU-UHFFFAOYSA-N 0.000 claims description 3
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- 230000007935 neutral effect Effects 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 6
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- JVHWZEWMZMHZFN-UHFFFAOYSA-N 4-(3-bromophenyl)dibenzothiophene Chemical compound BrC1=CC=CC(C=2C3=C(C4=CC=CC=C4S3)C=CC=2)=C1 JVHWZEWMZMHZFN-UHFFFAOYSA-N 0.000 description 4
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- 229910052736 halogen Inorganic materials 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
技术领域
本发明系关于一种有机发光器件,尤系关于一种可产生发光激基复合物的有机发光器件。
背景技术
有机发光器件(OLED)因其具有轻、薄、广视角、高对比度、低耗电、高响应速度、全彩、柔性等特点,因此,于全彩显示器或可携式电子装置方面之应用皆备受期待。
典型的OLED系藉由真空沉积法或涂布法依序沉积阳极、空穴传输层、发光层、电子传输层及阴极所形成之多层薄膜结构。当施加电流时,阳极注入空穴且阴极注入电子至该一层或多层有机层中,被注入的空穴及电子各自迁移至相反的带电荷电极。当电子及空穴局限在相同的分子上时,形成”激子(exciton)”,该激子系具有受激发能态的局限化电子─空穴对,通过发光机制该激子松弛而发射光。
为提升OLED的组件效率,日本九州岛大学安达千波矢(Chihaya Adachi)藉由适当的分子结构设计,使其单重激发态与三重激发态的能级差(ΔEST)缩小,增加逆系统间跨越(Reverse Inter-System Crossing;RISC)的可能性,达成热活化型延迟荧光(ThermallyActivated Delayed Fluorescence;TADF),令原本多以热运动方式散失能量的三重态激子,能回到单重态而放光,以达到理论上与磷光材料相同的100%内部量子效率。
除此之外,藉由两种独立具电荷传输的材料在接触界面生成激基复合物(exciplex),亦可达成低ΔEST,韩国J.J.Kim教授系以激基复合物作为共同主体材料制备有机发光器件,所形成的电荷施主之最高占据分子轨道(HOMO)及电荷受主之最低未占分子轨道(LUMO)间能级差,其特性相近于单重激发态和三重激发态能量,俾使单重态与三重态的能量完全转移至掺杂材料,大幅降低电荷注入势垒,惟,目前的挑战在于相当困难找到可在接触界面生成激基复合物之具电荷传输的材料。
因此,亟需开发一种有效提升组件性能的有机发光器件,以符合实际显示器应用之需求。
发明内容
本发明之目的在于提供一种提高有机发光器件之电流效率、外部量子效率、发光效率及降低操作电压等性能及延长其使用寿命。
本发明提供一种可产生发光激基复合物的有机发光器件,包含:阴极;阳极;以及发光层,系介于该阴极与阳极之间,且该发光层包括具式(I)之杂环化合物及具式(II)之三嗪衍生物,
其中,X系表示S或O;L1表示C6-C30亚芳基;Ar1和Ar2系为相同或相异,且各Ar1和Ar2系独立表示经C6-C9芳基、二-(C6-C9)芳基胺基、或至少一C1-C30烷基取代或未经取代之C6-C15芳基、或Ar2、N以及L1结合在一起以形成经(C6-C15)芳基取代或未经取代之咔唑部分;及Ar1及Ar2之至少一者具有C10-C15之芳香烃部分;
其中,各A1系为相同或相异且独立表示经取代或未经取代之C6-C20亚芳基、经取代或未经取代之含有选自由N、O、及S所组成群组中之至少一杂原子之C3-20亚杂芳基;
各Y系为相同或相异且独立选自卤基、硝基、羰基、吡啶基、氰基、吡唑基、经取代或未经取代之苯并咪唑基、经取代或未经取代之二唑基、经取代或未经取代之芳基砜基、经取代或未经取代之二-(C6-C20)芳基-膦氧基及经取代或未经取代之C6-C20芳基亚砜基所组成群组中之一者。
本发明提供之可产生发光激基复合物的有机发光器件,由于其发光层具有式(I)之杂环化合物及式(II)之三嗪衍生物所形成之发光激基复合物,使其单重激发态与三重激发态的能级差 (ΔEST)缩小,以有效提升整体组件性能并改善其有机发光器件的寿命。
附图说明
构成本发明的一部分的说明书附图用来提供对本发明的进一步理解,本发明的示意性实施例及其说明用于解释本发明,并不构成对本发明的不当限定。在附图中:
图1是本发明之有机发光器件之一实施例之剖面示意图;
图2是本发明之有机发光器件之另一实施例之剖面示意图;以及
图3是本发明之有机发光器件之又一实施例之剖面示意图。
其中,上述附图包括以下附图标记:
100、200、300有机发光器件;
110、210、310基板;
120、220、320阳极;
130、230、330空穴注入层;
140、240、340空穴传输层;
150、250、350发光层;
160、260、360电子传输层;
170、270、370电子注入层;
180、280、380阴极;
245电子阻挡层;
355空穴阻挡层。
具体实施方式
以下系藉由特定的具体实施例说明本发明之实施方式,熟习此技艺之人士可由本说明书所揭示之内容轻易地了解本发明之优点及功效。本发明亦可藉由其它不同之实施方式加以施行或应用,本说明书中的各项细节亦可基于不同观点与应用,在不悖离本发明所揭示之精神下赋予不同之修饰与变更。此外,本文所有范围和值都系包含及可合并的。落在本文中所述的范围内之任何数值或点,例如任何整数都可以作为最小值或最大值以导出下位范围等。
本发明提供一种可产生发光激基复合物的有机发光器件,包含:阴极;阳极;以及发光层,系介于该阴极与阳极之间,且该发光层包括具式(I)之杂环化合物及具式(II)之三嗪衍生物,
其中,X系表示S或O;L1表示C6-C30亚芳基;Ar1和Ar2系为相同或相异,且各Ar1和Ar2系独立表示经C6-C9芳基、二-(C6-C9)芳基胺基、或至少一C1-C30烷基取代或未经取代之C6-C15芳基、或Ar2、N以及L1结合在一起以形成经(C6-C15)芳基取代或未经取代之咔唑部分;及Ar1及Ar2之至少一者具有C10-C15之芳香烃部分;
其中,各A1系为相同或相异且独立表示经取代或未经取代之C6-C20亚芳基、经取代或未经取代之含有选自由N、O、及S所组成群组中之至少一杂原子之C3-20亚杂芳基;
各Y系为相同或相异且独立选自卤基、硝基、羰基、吡啶基、氰基、吡唑基、经取代或未经取代之苯并咪唑基、经取代或未经取代之二唑基、经取代或未经取代之芳基砜基、经取代或未经取代之二-(C6-C20)芳基-膦氧基及经取代或未经取代之C6-C20芳基亚砜基所组成群组中之一者。
文中,「芳基」表示芳基或(亚)芳基,该芳基系指衍生自芳香烃的单环或稠合多环,及包括,但不限于苯基、联苯基、联三苯基、萘基、联萘基、苯基萘基、萘基苯基、茀基、苯基茀基、苯并茀基、二苯并茀基、菲基、苯基菲基、蒽基、茚基、联亚三苯基、芘基、稠四苯基、苝基、蒯基、萘并萘基、丙二烯合茀基等。
文中,「杂芳基」表示杂芳基或(亚)杂芳基,该杂芳基系指含有选自由N、O、及S所组成群组中之至少一个杂原子的环主链原子的芳基,可为单环系环,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、异噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、三唑基、四唑基、呋呫基、吡啶基、吡嗪基、嘧啶基、哒嗪基等,或为与至少一个苯环缩合的稠合环,如苯并呋喃基、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹噁啉基、咔唑基、菲噁唑基、啡啶基、苯并二苊基、二氢吖啶基等。
文中,表达成「经取代或未经取代之」中的「经取代之」表示在某个官能基中之氢原子系经另一个原子或基团(即取代基)置换。该等取代基各自独立地选自由下列所组成之群组中之至少一者:氘、卤素、C1-C30烷基、C1-C30烷氧基、C6-C30芳基、C5-C30杂芳基、经C6-C30 芳基取代之C5-C30杂芳基、苯并咪唑基、C3-C30环烷基、C5-C7杂环烷基、三-(C1-C30)烷基硅烷基、三-(C1-C30)芳基硅烷基、二-(C1-C30)烷基-(C6-C30)芳基硅烷基、C1-C30烷基二 -(C6-C30)芳基硅烷基、C2-C30烯基、C2-C30炔基、氰基、二-(C1-C30)烷基胺基、二-(C6-C30) 芳基硼基、二-(C1-C30)烷基硼基、C1-C30烷基、C6-C30芳基C1-C30烷基、C1-C30烷基C6-C30 芳基、羧基、硝基及羟基。
所述之可产生发光激基复合物的有机发光器件,系藉由式(I)之杂环化合物及式(II)之三嗪衍生物结合形成之激基复合物,使热运动方式散失能量的三重态激子,能回到单重态而放光,以提升整体组件之量子效率。
文中,「激基复合物」(exciplex)系指藉由两种独立具电荷传输的材料在接触界面生成之激发态的络合物,透过该激基复合物而产生的发光现象则称为「发光激基复合物」。
于一具体实施例中,于该有机发光器件之发光层中,式(I)之杂环化合物及该式(II)之三嗪衍生物之重量比为3:7至8:2,其中,该式(I)之杂环化合物及该式(II)之三嗪衍生物之重量比又尤以1:1至4:1为佳。
关于式(I)之杂环化合物:
于一具体实施例中,前述之式(I)之杂环化合物之Ar1和Ar2各独立代表经取代或未经取代之C6-C15芳基。
所述经取代Ar1和Ar2之取代基系各独立选自C6-C9芳基、二-(C6-C9)芳基胺基、或至少一C1-C30烷基。
于另一具体实施例中,该C1-C30烷基系甲基,该C6-C9芳基系苯基,该二-(C6-C9)芳基胺基系二苯基胺基。
所述之取代基可经由被取代基团之任一位置链接。然而,该二-(C6-C9)芳基胺基不经由邻位连结至该C6-C15芳基。
于一具体实施例中,该式(I)之杂环化合物之Ar1和Ar2各独立表示苯基、萘基、联苯基、二甲基芴基或(二苯基胺基)苯基。
于一具体实施例中,Ar1及Ar2之至少一者具有C10-C15之芳香烃部分。
于一具体实施例中,Ar1表示苯基、萘基、联苯基、二甲基芴基或(二苯基胺基)苯基;以及Ar2、N以及L1结合在一起以形成经取代或未经取代之咔唑部分。
于另一具体实施例中,该咔唑部分系经(C6-C15)芳基取代。较佳者,该咔唑部分系以苯基、萘基或联苯基取代。
于又一具体实施例中,该式(I)之杂环化合物之咔唑部分系2,9-亚咔唑或3,9-亚咔唑。
于一具体实施例中,当Ar1表示(二苯基胺基)苯基时,Ar2系表示为苯基、萘基或联苯基。
于一具体实施例中,该式(I)之杂环化合物之L1系表示亚苯基或亚联苯基。
于一具体实施例中,该式(I)之杂环化合物之L1系表示亚苯基或亚联苯基且该Ar1和Ar2系为相同时,该Ar1和Ar2系具有C10-C15之芳香烃部分。其中,该Ar1和Ar2又尤以联苯基或萘基为佳。
前述具式(I)之杂环化合物之较佳实施例系选自于表1,但不限于此。
表1
以下说明式(I)之杂环化合物的典型合成途径之一,其系遵守文献中提到的铃木偶联 (Suzuki coupling)以及哈特维希胺化作用(Hartwig amination)的条件。
下列合成例系参照上述内容更详细说明本发明之式(I)之杂环化合物之合成步骤;然而,本发明不应受限于该些实施例所例示者。
合成例1
于250mL烧瓶中,使4-(4’-溴苯基)二苯并[b,d]呋喃(10g)、四氢呋喃(90mL)之混合物于氮气氛围下搅拌且冷却至-78℃,于-78℃注入正-丁基锂溶液(18.8ml,2.5M于正己烷中),且于 -78℃搅拌2小时。2小时后,注入硼酸三甲酯(16g)且使该反应平衡至室温过夜,以薄层层析法监测该反应。于完成该反应后,添加2N盐酸溶液(60mL)于该反应混合物且搅拌1小时,以水(50mL)淬灭该反应混合物,且使用乙酸乙酯(70mL)萃取,以水(3x 50mL)萃取该有机层且以无水硫酸钠干燥。随之,真空下于旋转蒸发器中蒸发乙酸乙酯层至干燥以产生4-(二苯并呋喃 -4’-基)苯基硼酸(5g)。
使4-(二苯并呋喃-4’-基)苯基硼酸(5g)、2-溴咔唑(4.7g)、肆(三苯基膦)钯(1g)、甲苯(64mL)、乙醇(7mL)、水(20mL)以及碳酸钾(6.6g)之混合物于回流下搅拌,以薄层层析法监测该反应。于完成该反应后,以水(100mL)淬灭该反应混合物,且使用乙酸乙酯(100mL)萃取,以水(3x 30mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,真空下于旋转蒸发器中蒸发乙酸乙酯层至干燥以产生HPLC纯度超过99%之化合物1-1(1g,39%)。
化合物1-1之熔点为246.35℃以及玻璃转化温度为95.24℃。
1H NMR(CDCl3,δ):8.34-8.27(m,1H);8.26-8.02(m,3H);7.98-7.88(m,2H);7.86-7.80(m,1H); 7.58-7.66(d,2H);7.60-7.40(m,7H);7.38-7.30(m,1H);7.29-7.21(m,7H);7.20-7.10(m,1H)。
合成例2
于250mL烧瓶中,在回流下搅拌二苯并[b,d]噻吩-4-基硼酸(5g,20.31mmol)、3-溴咔唑(4.9g, 21.33mmol)、肆(三苯基膦)钯(1.2g,1.01mmol)、甲苯(60ml)、乙醇(8ml)、H2O(20ml)以及碳酸钾(7.4g,53.33mmol)之混合物5小时,以薄层层析法监测该反应。于完成该反应后,以水(30mL) 淬灭该反应混合物,且使用乙酸乙酯(50mL)萃取,以水(3x30mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,真空下于旋转蒸发器中蒸发乙酸乙酯层至干燥以产生2-(二苯并[b,d]噻吩-4-基)-9H-咔唑(3g)。
使2-(二苯并[b,d]噻吩-4-基)-9H-咔唑(2g,58.72mmol)、2-溴萘(1.3g,6.29mmol)、双(二亚芐基丙酮)钯(0)(0.1g,0.17mmol)、第三丁醇钠(1.1g,11.44mmol)、甲苯(30ml)、三(第三丁基) 膦(0.09g,0.45mmole)之混合物于氮气氛围下回流,以薄层层析法监测该反应。于完成该反应后,以水(20mL)淬灭该反应混合物,且使用乙酸乙酯(50mL)萃取,以水(3x20mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,在真空下用旋转蒸发器蒸发乙酸乙酯层至干燥。进一步藉由添加200mL甲醇沉淀该残留物,真空下过滤及干燥。获得HPLC纯度超过99%且呈黄色固体之1g化合物1-4(36%)。
化合物1-4之熔点为187.51℃以及玻璃转化温度为101.31℃。
1H NMR(CDCl3,δ):8.56-8.53(d,1H);8.25-8.14(m,3H);7.13-7.09(m,2H);8.02-7.92(m,2H); 7.85-7.79(m,2H);7.76-7.72(m,1H);7.64-7.57(m,5H);7.53-7.42(m,4H);7.37-7.31(m,1H)。
合成例3
于150mL烧瓶中,使2-(二苯并[b,d]呋喃-4-基)-9H-咔唑(3.5g)、4-溴三苯基胺(3.7g)、双(二亚芐基丙酮)钯(0)(0.18g)、第三丁醇钠(2g)、甲苯(53mL)、三(第三丁基)膦(0.17g)之混合物于氮气氛围下回流,以薄层层析法监测该反应。于完成该反应后,以水(30mL)淬灭该反应混合物,且使用乙酸乙酯(50mL)萃取,以水(3x30mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,在真空下用旋转蒸发器蒸发乙酸乙酯层至干燥。进一步藉由添加甲醇沉淀该残留物,真空下过滤及干燥。获得HPLC纯度超过99%且呈黄色固体之3.5g化合物1-7(57%)。
化合物1-7之熔点为283.3℃以及玻璃转化温度为94.64℃。
1H NMR(CDCl3,δ):8.29-8.27(d,1H);8.20-8.18(d,1H);8.01-8.00(m,2H);7.95-7.94(m,1H); 7.85-7.83(d,1H);7.71-7.69(m,1H);7.55-7.54(d,1H);7.50-7.43(m,7H);7.39-7.36(t,1H); 7.31-7.20(m,10H);7.08-7.07(t,2H)。
合成例4
于80℃搅拌二苯并噻吩-4-硼酸(10克(g))、1,4-二溴苯(9.4g)、肆(三苯基膦)钯(2.42g)、甲苯(120毫升(mL))、乙醇(16毫升(mL))、水(46mL)以及碳酸钾(14.44g)之混合物5小时。以薄层层析法监测该反应;于完成该反应后,以水(100mL)淬灭该反应混合物且使用乙酸乙酯(100mL) 萃取,以水(3x30ml)萃取该有机层,并以无水硫酸钠干燥。使该收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,真空下于旋转蒸发器中蒸发乙酸乙酯层至干燥以产生13.52g之4-(4’-溴苯基)二苯并噻吩。将4-(4’-溴苯基)二苯并噻吩(10g)、双(4-联苯基)胺基 (13.08g)、双(二亚芐基丙酮)钯(0)(0.152g)、第三丁醇钠(6.52g)、甲苯(125ml)、三(第三丁基) 膦(0.274g)之混合物添加在一起,且于氮气氛围下回流,以薄层层析法监测该反应。于完成该反应后,以水(50ml)淬灭该反应混合物,且使用乙酸乙酯(100ml)萃取。以水(3x 30ml)萃取该有机层且以无水硫酸钠干燥。使所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,在真空下用旋转蒸发器蒸发乙酸乙酯层至干燥。藉由添加200mL甲醇进一步沉淀该残留物,真空下过滤及干燥。获得HPLC纯度超过99%且呈黄色固体之10.38g化合物1-12(44%)。
化合物1-12之熔点为278.3℃且玻璃转化温度为102.9℃。
1H NMR(CDCl3,δ):8.16-8.11(m,2H);7.79-7.77(m,1H);7.58-7.39(m,18H);7.33-7.22(m, 8H)。
合成例5
于250mL烧瓶中,使4-(4’-溴苯基)二苯并噻吩(10g)、N-苯基-2-萘胺 (N-Phenylnaphthalen-2-amine,7.75g)、双(二亚芐基丙酮)钯(0)(0.59g)、第三丁醇钠(6.5g)、甲苯 (150ml)、三(第三丁基)膦(0.55g)之混合物于氮气氛围下回流,以薄层层析法监测该反应。于完成该反应后,以水(50mL)淬灭该反应混合物,且使用乙酸乙酯(70mL)萃取。以水(3x50mL) 萃取该有机层且以无水硫酸钠干燥。使所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,在真空下用旋转蒸发器蒸发乙酸乙酯层至干燥。将该残留物进一步沉淀于甲醇(100ml)中,真空下过滤及干燥。获得HPLC纯度超过99%且呈黄色固体之7g化合物 1-14(49%)。
化合物1-14之熔点为202.21℃以及玻璃转化温度为82.08℃。
1H NMR(CDCl3,δ):8.30-8.17(m,1H);8.16-8.10(m,1H);7.88-7.83(m,1H);7.82-7.76(m,2H); 7.68-7.63(m,3H);7.58-7.30(m,9H);7.29-7.22(m,5H);7.14-7.08(m,1H)。
合成例6
于80℃搅拌4-二苯并呋喃硼酸(13.3g)、1,4-二溴苯(10g)、肆(三苯基膦)钯(3.02g)、甲苯 (158mL)、乙醇(65mL)、水(65ml)以及碳酸钾(21.69g)之混合物5小时,以薄层层析法监测该反应。于完成该反应后,以水(100mL)淬灭该反应混合物,且使用乙酸乙酯(100mL)萃取。以水(3 x30ml)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,真空下于旋转蒸发器中蒸发乙酸乙酯层至干燥以产生13.7g之4-(4’-溴苯基)二苯并呋喃。
于500mL烧瓶中,使4-(4’-溴苯基)二苯并呋喃(10g)、双(4-联苯基)胺基(12.7g)、双(二亚芐基丙酮)钯(0)(0.62g)、第三丁醇钠(6.9g)、二甲苯(150mL)、三(第三丁基)膦(0.58g)之混合物于氮气氛围下回流,以薄层层析法监测该反应。于完成该反应后,以水(50mL)淬灭该反应混合物,且使用乙酸乙酯(70mL)萃取。以水(3x50mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,在真空下用旋转蒸发器蒸发乙酸乙酯层至干燥。将该残留物进一步沉淀于甲醇(100ml)中,真空下过滤及干燥。获得 HPLC纯度超过99%且呈淡黄色固体之7.67g化合物1-18(44%)。
化合物1-18之玻璃转化温度为96.57℃。
1H NMR(CDCl3,δ):8.00(d,1H);7.98-7.87(m,3H);7.63-7.53(m,10H);7.49-7.38(m,15H)。
合成例7
于500mL烧瓶中,使4-(4’-溴苯基)二苯并呋喃(4.2g)、N-(4-联苯基)-(9,9-二甲基茀-2-基) 胺基(5g)、双(二亚芐基丙酮)钯(0)(0.24g)、第三丁醇钠(2.65g)、甲苯(75mL)、三(第三丁基)膦 (0.22g)之混合物于氮气氛围下回流。于完成该反应后,以水(50mL)淬灭该反应混合物,且使用乙酸乙酯(70mL)萃取。以水(3x50mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,在真空下用旋转蒸发器蒸发乙酸乙酯层至干燥,获得HPLC纯度超过99%且呈黄色固体之3.45g化合物1-24(44%)。
化合物1-24之玻璃转化温度为110.5℃。
1H NMR(CDCl3,δ):8.01-7.99(d,1H);7.92-7.88(m,3H);7.69-7.55(m,11H);7.49-7.26(m, 17H);7.20-7.18(dd,1H)。
合成例8
于80℃搅拌4-二苯并呋喃硼酸(13.3g)、1,3-二溴苯(10g)、肆(三苯基膦)钯(3.02g)、甲苯 (158mL)、乙醇(65mL)、水(65mL)以及碳酸钾(21.69g)之混合物5小时,以薄层层析法监测该反应。于完成该反应后,以水(100mL)淬灭该反应混合物,且使用乙酸乙酯(100mL)萃取。以水(3x30mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,真空下于旋转蒸发器中蒸发乙酸乙酯层至干燥以产生13.7g之4-(3’- 溴苯基)二苯并呋喃。
使4-(3’-溴苯基)二苯并呋喃(7.4g)、N-(4-联苯基)-(9,9-二甲基茀-2-基)胺基(10g)、双(二亚芐基丙酮)钯(0)(0.46g)、第三丁醇钠(5.1g)、甲苯(110mL)、三(第三丁基)膦(0.43g)之混合物于氮气氛围下回流,以薄层层析法监测该反应。于完成该反应后,以水(50mL)淬灭该反应混合物,且使用乙酸乙酯(70mL)萃取,以水(3x50mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,在真空下用旋转蒸发器蒸发乙酸乙酯层至干燥,获得HPLC纯度超过99%且呈黄色固体之6.12g化合物1-28(44%)。
化合物1-28之玻璃转化温度为103.11℃。
1H NMR(CDCl3,δ):8.09-7.93(d,1H);7.92-7.89(d,1H);7.73-7.72(t,1H);7.71-7.60(m,6H); 7.57-7.30(m,22H);7.29-7.2(dd,2H)。
合成例9
于80℃搅拌二苯并[b,d]噻吩-4-基硼酸(10g,38.4毫摩尔(mmol))、1,3-二溴苯(9.5g, 40.33mmol)、肆(三苯基膦)钯(2.3g,2.01mmol)、甲苯(130ml)、乙醇(17ml)、H2O(45ml)以及碳酸钾(13.9g,100mmol)之混合物添5小时,以薄层层析法监测该反应。于完成该反应后,以水 (100mL)淬灭该反应混合物,且使用乙酸乙酯(100mL)萃取,以水(3x30mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,在真空下于旋转蒸发器中蒸发乙酸乙酯层至干燥,产生4-(3-溴苯基)二苯并[b,d]噻吩(8.2g)。
使4-(3-溴苯基)二苯并[b,d]噻吩(8.2g)(3.5g,10.31mmol)、双(4-联苯基)胺基(3.48g, 10.83mmol)、双(二亚芐基丙酮)钯(0)(0.19g,0.32mmol)、第三丁醇钠(2g,21.65mmol)、二甲苯(40ml)、三第三丁基膦(0.17g,0.86mmole)之混合物于氮气氛围下回流,以薄层层析法监测该反应。于完成该反应后,以水(30mL)淬灭该反应混合物,且使用乙酸乙酯(50mL)萃取,以水(3x 30mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,在真空下用旋转蒸发器蒸发乙酸乙酯层至干燥,获得HPLC纯度超过99%之呈黄色固体之3.0g化合物1-32(50%)。
化合物1-32之熔点为191.22℃以及玻璃转化温度为93.21℃。
1H NMR(CDCl3,δ):8.18-8.10(m,2H);7.82-7.78(m,1H);7.62-7.49(m,6H);7.48-7.38(m, 11H);7.34-7.22(m,9H)。
合成例10
于250mL烧瓶中,使4-(3’-溴苯基)二苯并噻吩(5g)、N-(4-联苯基)-(9,9-二甲基茀-2-基)胺基(6.39g)、双(二亚芐基丙酮)钯(0)(0.29g)、第三丁醇钠(3.27g)、甲苯(95mL)、三(第三丁基)膦 (0.28g)之混合物于氮气氛围下回流,以薄层层析法监测该反应。于完成该反应后,以水(50mL) 淬灭该反应混合物,且使用乙酸乙酯(70mL)萃取,以水(3x50mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,在真空下用旋转蒸发器蒸发乙酸乙酯层至干燥,获得HPLC纯度超过99%且呈黄色固体之3.0g化合物 1-40(32%)。
化合物1-40之熔点为202.82℃以及玻璃转化温度107.65℃。
1H NMR(CDCl3,δ):7.77-7.43(m,1H);7.68-7.62(m,3H);7.62-7.58(m,3H);7.55-7.47(m,5H); 7.46-7.23(m,20H);7.20-7.16(m,1H)。
合成例11
使4-(3’-溴苯基)二苯并呋喃(2.7g)、双(4-联苯基)胺基(3.1g)、双(二亚芐基丙酮)钯(0)(0.14g)、第三丁醇钠(1.6g)、二甲苯(40ml)、三第三丁基膦(0.13g)之混合物于氮气氛围下回流,以薄层层析法监测该反应。于完成该反应后,以水(30mL)淬灭该反应混合物,且使用乙酸乙酯(50mL)萃取,以水(3x30mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,在真空下用旋转蒸发器蒸发乙酸乙酯层至干燥,藉由添加200mL甲醇进一步沉淀该残留物,真空下过滤及干燥。获得HPLC纯度超过 99%且呈黄色固体之3g化合物1-43(63%)。
化合物1-43之熔点为177℃以及玻璃转化温度为86.8℃。
1H NMR(CDCl3,δ):7.97-7.94(d,1H);7.92-7.88(m,1H);7.77-7.74(t,1H);7.64-7.54(m,10H); 7.51-7.30(m,15H);7.30-7.26(m,1H)。
合成例12
使4-(3’-溴苯基)二苯并[b,d]噻吩(2.6g)、N1-(萘-1-基)-N4,N4-二苯基苯-1,4-二胺(3.55g)、双(二亚芐基丙酮)钯(0)(0.15g)、第三丁醇钠(1.7g)、甲苯(50mL)、三第三丁基膦(0.14g)之混合物于氮气氛围下回流,以薄层层析法监测该反应。于完成该反应后,以水(30mL)淬灭该反应混合物,且使用乙酸乙酯(50mL)萃取,以水(3x30mL)萃取该有机层且以无水硫酸钠干燥。将所收集之乙酸乙酯层通过硅藻土管柱层析法用以进一步纯化。随之,在真空下用旋转蒸发器蒸发乙酸乙酯层至干燥,藉由添加200mL甲醇进一步沉淀该残留物,真空下过滤及干燥。获得 HPLC纯度超过99%且呈黄色固体之2g化合物1-51(40%)。
化合物1-51之熔点为167.01℃以及玻璃转化温度为99.93℃。
1H NMR(CDCl3,δ):8.14-8.06(m,7H);7.93-7.90(d,3H);7.71-7.73(m,1H);7.68-7.62(t,2H); 7.62-7.58(m,2H);7.55-7.47(m,4H);7.46-7.67(m,3H);7.52-7.39(m,19H)。
关于式(II)之三嗪衍生物:
于一具体实施例中,该A1系代表经取代或未经取代之C6-C20亚芳基,其实例包括但不限于亚苯基、亚萘基、亚蒽基、亚联苯基、亚菲基、亚芴基及其类似物。
于另一具体实施例中,该A1系代表经取代或未经取代之含有选自由N、O、及S所组成群组中之至少一杂原子之C3-20亚杂芳基,其实例包括但不限于亚吡啶基、亚吡嗪基、亚嘧啶基、亚哒嗪基、亚吲哚基、亚吲唑基、亚咔唑基、亚噻唑基、亚噻吩基、亚呋喃基及其类似物。
于一具体实施例中,该式(II)之三嗪衍生物之Y系可键结于A1之任一位置。
于一具体实施例中,该式(II)之三嗪衍生物之A1系皆为相同时,Y系皆为相同且键结于 A1的位置亦同。
于一具体实施例中,该A1系皆为亚联苯基或亚苯基。
于另一具体实施例中,该式(II)之三嗪衍生物之A1皆为亚苯基时,且Y系相对于三嗪环键结于A1之间位位置。
前述具式(II)之三嗪衍生物之较佳实施例系选自于表2,但不限于此。
表2
关于具式(II)之三嗪衍生物之合成步骤系揭示于第I501959号台湾地区专利,其全文亦并入本文参考。
于本发明之可产生发光激基复合物的有机发光器件中,该发光层厚度系200至300埃;其中,该发光层可仅由式(I)之杂环化合物及式(II)之三嗪衍生物所组成,或将式(I)之杂环化合物及式(II)之三嗪衍生物作为发光主体,并与其他客发光体结合使用。
于一具体实施例中,本发明之可产生发光激基复合物的有机发光器件之发光层复包含客发光体。
于一具体实施例中,本发明之可产生发光激基复合物的有机发光器件之客发光体系为磷光掺杂剂,且该具式(I)之杂环化合物及具式(II)之三嗪衍生物作为发光主体材料,俾使单重态与三重态的能量完全转移至磷光掺杂剂,大幅降低电荷注入势垒。
于本发明之可产生发光激基复合物的有机发光器件中,该发光层之磷光掺杂剂的含量系为1wt%至5wt%,较现有技术的掺杂添加量更少,更有利于降低制备成本。其中,该发光层之磷光掺杂剂的含量优选为1wt%至3wt%。
于一具体实施例中,本发明之可产生发光激基复合物的有机发光器件之发光层系发射红光。
于另一具体实施例中,该磷光掺杂剂系包含至少一种选自钌、铑、钯、银、铼、锇、铱、铂金及金所组成群组之金属的有机金属配合物。
于又一具体实施例中,该磷光掺杂剂(PER)系为三[1-苯基异喹啉-C2,N]铱(Ⅲ)(Ir(piq)3),其结构如下式(3-1)所示:
于本发明之可产生发光激基复合物的有机发光器件中,除了上述之发光层外,复包含至少一层形成于该阳极及该发光层间之空穴辅助层。其中,该空穴辅助层之材料系可选择常用材料,常见用于空穴辅助层之材料系包括选自三唑衍生物、噁二唑衍生物、咪唑衍生物、苯二胺衍生物、星状多胺类衍生物、螺环接分子衍生物或芳胺衍生物所组成之群组之至少一者。
于一具体实施例中,该空穴辅助层系排除使用式(I)之杂环化合物,配合本发明前述之技术手段所设置之发光层,得以再优化并提升其发光组件性能。
于本发明之可产生发光激基复合物的有机发光器件中,可复包含至少一层形成于该发光层及该阴极间之电子辅助层。其中,该电子辅助层之材料系可选择常用材料,常见用于电子注入层之材料系包括碱金属卤化物或含氮、氧之碱金属螯合物,如:LiF、8-quinolinolato lithium (Liq);习知的电子传输层材料系包括选自有机碱金属/碱土金属络合物、氧化物、卤化物、碳酸盐及含有至少一种选自锂和铯金属之磷酸碱金属/碱土金属盐所组成之群组之其中一种。
于一具体实施例中,该电子辅助层系排除使用式(II)之三嗪衍生物,同样地,配合本发明前述之技术手段所设置之发光层,得以再优化并提升其发光组件性能。
所述之空穴辅助层可为空穴注入层、空穴传输层或电子阻挡层;同样地,所述之电子辅助层亦可为电子注入层、电子传输层或空穴阻挡层。
本发明之有机发光器件之结构将配合图式加以说明。
图1是本发明之有机发光器件之一实施例之剖面示意图,该有机发光器件100包含基板 110、阳极120、空穴注入层130、空穴传输层140、发光层150、电子传输层160、电子注入层170及阴极180。有机发光器件100可经由依序沉积上述各层来制作。
图2是本发明之有机发光器件之另一具体实施例之剖面示意图。有机发光器件200包含基板210、阳极220、空穴注入层230、空穴传输层240、电子阻挡层245、发光层250、电子传输层260、电子注入层270及阴极280,与图1之差异在于该电子阻挡层245系设于空穴传输层240与发光层250之间。
图3是本发明之有机发光器件之又一具体实施例之剖面示意图。有机发光器件300包含基板310、阳极320、空穴注入层330、空穴传输层340、发光层350、空穴阻挡层355、电子传输层360、电子注入层370及阴极380,与图1之差异在于该空穴阻挡层355系设于发光层350与电子传输层360之间。
上述图式所示结构之有机发光器件可反向制造,在该相反结构中,可视需要增加或移除一层或多层。
所述之阳极为具高功函数之金属或导电化合物,可选择常用材料包括透明金属氧化物如: ITO、IZO、SnO2、ZnO等材料或如poly-Si、a-Si等基材,于第5844363号美国专利揭示一种结合阳极之可挠性透明基底,其全部内容为本发明所引用。
所述之阴极为具低功函数之金属或导电化合物,可选择常用材料包括Au、Al、In、Mg、 Ca或类似之金属、合金等,于第5703436及5707745号美国专利所例示阴极之全部内容为本发明所引用,该阴极具有金属薄层,如:镁/银(Mg:Ag),及以溅镀沉积覆盖金属薄层之透明导电层(ITO Layer)。
此外,上述电极中需至少有一为透明或半透明的,以利于发射光穿透。
未特别说明之结构及材料亦可应用于本发明,如第5247190号美国专利所揭示包括聚合物材料(PLEDs)之有机发光器件,其全部内容为本发明所引用。如第20030230980号美国专利所例示n型掺杂之电子传输层系以摩尔比1:1于BPhen掺杂锂,其全部内容为本发明所引用。第6097147及20030230980号美国专利所揭示各阻挡层之应用及原理,其全部内容为本发明所引用。第20040174116号美国专利所例示之注入层及同案所说明之保护层,其全部内容为本发明所引用。
除有特别限定,不同实施例中之任何层可使用任何适当方法来沉积形成。以有机层而言,较佳之方法包含如第6013982及6087196号美国专利所揭示之热蒸镀法及喷印法,其全部内容为本发明所引用;第6337102号美国专利所揭示有机气相沉积法(organicvapor phase deposition,OVPD),其全部内容为本发明所引用;第10/233470号美国专利所揭示有机气相喷印沉积法(deposition by organic vapor jet printing,OVJP),其全部内容为本发明所引用。其他适当方法包含旋转涂布及以溶液为基础之制程。以溶液为基础之制程较佳是在氮气或惰性气体环境中进行。对于其他之层而言,较佳之方法包含热蒸镀法。较佳的图案化方法包含如第 6294398及6468819号美国专利所揭示通过屏蔽沉积再冷焊之制程,及整合喷印或有机气相喷印沉积与图案化之制程,其全部内容为本发明所引用。当然亦可使用其他方法。用于沉积之材料可予调整以对应其所特用之沉积方法。
本发明之有机发光器件可应用于单一组件,其结构为数组配置或数组X-Y坐标中设有阴阳两极之组件。相较于习知组件,本发明能显著提升有机发光器件之使用寿命及驱动稳定性。
以下藉由实施例详细说明本发明之诸多性质及功效。该等详述实施例仅用于说明本发明之性质,本发明不限于特定实施例所例示者。
实施例1:有机发光器件之制造
于基底加载蒸镀系统使用前,先以溶剂及紫外线臭氧清洗基底进行脱脂。之后,将基底传送至真空沉积室,于基底之顶部沉积所有层。依图2所示之各层系由加热的蒸镀舟(boat)在约10-6托之真空度依序沉积:
a)氧化铟锡层(ITO),厚度1350埃
b)空穴注入层,厚度200埃包含掺杂有2wt%p型电性传导掺质之HT623(昱镭光电制备),其中,该p型电性传导掺质系购自上海瀚丰化工有限公司;
组件结构可表示如:ITO(1350埃)//p型电性传导掺质:HT623(200埃)//HT623(1000 埃)//HT305(600埃)//PER:化合物1-51/化合物2-1(300埃)//Liq:ET(300埃)//LiF(3埃)//Al(1500 埃)。
于沉积形成上述各层后,该组件自沉积室传送至干燥箱中,随即以UV可固化环氧树脂及含有吸湿剂之玻璃盖板进行封装。该有机发光器件具有9平方毫米之发光区域。
实施例2至6:有机发光器件之制造
以相同实施例1的层结构及制法制备实施例2至6之有机发光器件,惟异动其发光层之化合物1-51及化合物2-1组成比例及客发光体PER的体积比,如表3及表4所示。
将上述制成之有机发光器件之电激发光性质均使用定电流源(KEITHLEY 2400Source Meter,made by Keithley Instruments,Inc.,Cleveland,Ohio)及亮度计(PHOTORESEARCH SpectraScan PR 650,made by Photo Research,Inc.,Chatsworth,Calif.)于室温下测量其发光性质,将有机发光器件操作达亮度于1000尼特(nits)之操作电压(V)、亮度、色彩空间坐标(CIE(x,y))、发光波长、电流效率、发光效率、外部量子效率(EQE)及T50值等性能结果列示于表3,以及于平均电流密度10毫安/平方厘米(mA/cm2)操作下之有机发光器件之性能结果列示于表4。其中,T50值之定义为亮度水平降至相对于初始亮度的50%的水平所消耗的时间,系作为评估有机发光器件之使用寿命或稳定性的衡量标准。
表3
表3(续)
表4
表4(续)
如表3及表4所述,由于上述之发光层具有式(I)之杂环化合物及式(II)之三嗪衍生物所形成之发光激基复合物,具有提高组件之电流效率、外部量子效率、发光效率及降低操作电压之特性,并能延长其使用寿命,展现高稳定性之组件性能。
上述实施例仅为例示性说明,而非用于限制本发明。任何熟习此项技艺之人士均可在不违背本发明之精神及范畴下,对上述实施例进行修饰与改变。因此,本发明之权利保护范围系由本发明所附之申请专利范围所定义,只要不影响本发明之效果及实施目的,应涵盖于此公开技术内容中。
Claims (16)
1.一种可产生发光激基复合物的有机发光器件,包含:
阴极;
阳极;以及
发光层,系介于该阴极与阳极之间,且该发光层包括具式(I)之杂环化合物及具式(II)之三嗪衍生物,
其中,X系表示S或O;
L1表示C6-C30亚芳基;
Ar1和Ar2系为相同或相异,且各Ar1和Ar2系独立表示经C6-C9芳基、二-(C6-C9)芳基胺基、或至少一C1-C30烷基取代或未经取代之C6-C15芳基、或Ar2、N以及L1结合在一起以形成经(C6-C15)芳基取代或未经取代之咔唑部分;及
Ar1及Ar2之至少一者具有C10-C15之芳香烃部分;
其中,各A1系为相同或相异且独立表示经取代或未经取代之C6-C20亚芳基、经取代或未经取代之含有选自由N、O、及S所组成群组中之至少一杂原子之C3-20亚杂芳基;
2.根据权利要求1所述的有机发光器件,其中,该式(I)之杂环化合物之Ar1和Ar2各独立表示苯基、萘基、联苯基、二甲基芴基或(二苯基胺基)苯基。
3.根据权利要求1所述的有机发光器件,其特征在于,其中,该式(I)之杂环化合物之咔唑部分系2,9-亚咔唑或3,9-亚咔唑。
5.根据权利要求1所述的有机发光器件,其中,该式(I)之杂环化合物之L1系表示亚苯基。
7.根据权利要求1所述的有机发光器件,其中,该式(II)之三嗪衍生物之A1皆为亚联苯基。
9.根据权利要求1所述的有机发光器件,其中,该式(II)之三嗪衍生物之A1皆为亚苯基,且Y系相对于三嗪环键结于A1之间位位置。
10.根据权利要求9所述的有机发光器件,其中,该式(II)之三嗪衍生物系选自由下列化合物所组成之群组:
11.根据权利要求1所述的有机发光器件,其中,该式(I)之杂环化合物及该式(II)之三嗪衍生物之重量比为3:7至8:2。
12.根据权利要求1所述的有机发光器件,其中,该发光层复包含客发光体,其中,该客发光体系为磷光掺杂剂,且该磷光掺杂剂的含量为1wt%至3wt%。
13.根据权利要求12所述的有机发光器件,其中,该发光层系发射红光。
14.根据权利要求12所述的有机发光器件,其中,该磷光掺杂剂系包含至少一种选自钌、铑、钯、银、铼、锇、铱、铂金及金所组成群组之金属的有机金属配合物。
15.根据权利要求14所述的有机发光器件,其中,该磷光掺杂剂系为三[1-苯基异喹啉-C2,N]铱(Ⅲ)。
16.根据权利要求1所述的有机发光器件,其中,该发光层厚度系200至300埃。
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