CN108586541A - 一类用作磷光材料的过渡金属配合物及其应用 - Google Patents
一类用作磷光材料的过渡金属配合物及其应用 Download PDFInfo
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- CN108586541A CN108586541A CN201810582621.3A CN201810582621A CN108586541A CN 108586541 A CN108586541 A CN 108586541A CN 201810582621 A CN201810582621 A CN 201810582621A CN 108586541 A CN108586541 A CN 108586541A
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- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 150000002602 lanthanoids Chemical class 0.000 description 1
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- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IBXNCJKFFQIKKY-UHFFFAOYSA-N n-propylacetylene Natural products CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000001296 phosphorescence spectrum Methods 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical compound C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Abstract
本发明涉及一类用作磷光材料的过渡金属配合物及其应用,具有如式(1)所示的分子结构:本发明的过渡金属配合物中含有一类新型辅助配体Ⅰ,该配体不仅有着与常用的乙酰丙酮一样的辅助配位作用,而且其轨道对过渡金属配合物的前线轨道有很大贡献,该配体与主配体Ⅱ相搭配,使得该过渡金属配合物发射光的波长可以从青绿光到橙红光进行调节,进而可调节其光电性能。
Description
技术领域
本发明涉及一种过渡金属配合物及其应用,尤其涉及一类用作磷光材料的过渡金属配合物及其应用。
背景技术
有机电致发光器件(OLED)作为新一代的显示技术,克服了第一代CRT显示器体积大、笨重、功耗大的缺点,也克服了LCD显示器视角小、响应速度慢、低温下不可使用且自身不能发光的不足,其最大的突破在于材料的机械韧性、低温制程及夹层式器件结构,不仅可以获得比传导性结构LCD更好的视觉效果,还可以在任何轻薄基板上得到应用,具有非常诱人的应用前景,发展潜力巨大。
在OLED的研究中,有机材料的选择起着决定性的作用。三明治型OLED器件按照功能分类可分为空穴注入层、空穴传输层、发光层、电子传输层及电子注入层等,而发光层的材料叫做主体材料。
由于贵金属的自旋-轨道耦合效应,使得原本自旋禁阻的激发态三线态到基态单线态的辐射跃迁变为局部允许,基于金属配合物的PhOLED(phosphorescent OLED)能有效地利用单线态激子和三线态激子,理论上内量子效率可以达到100%,并且单线态激发态到三线态激发态的系间窜跃几率显著提高,促进PhOLED产生高效磷光发光。与荧光OLED相比,PhOLED的诸多优势使其备受关注,逐渐成为研究的热点。磷光材料作为发光层,经过材料化学修饰和器件结构优化,器件抗浓度淬灭能力增强,发光效率可稳步提升。
在众多的贵金属配合物包括稀土元素配合物中,较多使用的是锇、铱、铂、钯等元素。除了金属元素对金属配合物性能的影响较大外,金属配合物中的配体对其性能也具有较大的影响。Forrest和Thompson等基于环化金属配体和辅助配体合成了一系列的金属配合物。这些金属配合物的最低三重激发态由金属d轨道到配体π*轨道的三重激发态和配体轨道到π*轨道的三重激发态组成,采用不同环金属化配体可实现磷光光谱的红移。为了发出重组的磷光,要求辅助配体的三重激发态能级要高于环金属化配体和金属到配体的三重激发态能级。因而磷光材料的关键在于配体的选择和搭配,目前常用的磷光材料配体包含主配体和辅助配体。常用的辅助配体有乙酰丙酮及基于乙酰丙酮的衍生物2,2,6,6-四甲基-3,5-庚二酸、2-吡啶甲酸等。这些辅助配体的前线轨道对磷光材料配合物的前线轨道贡献可以忽略,所以目前磷光材料的发光波长和效率的提高主要是通过调节主配体实现的。
设计合适的辅助配体,能够参与到磷光材料的发光颜色和效率的调节将对磷光材料的发展具有重要意义。
发明内容
本发明针对现有作为磷光材料的过渡金属配合物中辅助配体对配合物的前线轨道无贡献的现状,提供一类用作磷光材料的过渡金属配合物及其应用。
本发明解决上述技术问题的技术方案如下:
一类用作磷光材料的过渡金属配合物,具有如式(1)所示的分子结构:
式(1)中,M为过渡金属Ru、Re、Os、Ir、Au、Pd、Pt、Zr或Hf中的任意一种,M右侧为辅助配体Ⅰ,M左侧为主配体Ⅱ,n和m均为大于等于1的整数;
其中,辅助配体I中的Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8和Y9各自独立的为C、N、O、S、Se、CR1、CR2R3或NR4;主配体Ⅱ中的X1、X2、X3、X4各自独立的为N或C,Ar1环和Ar2环各自独立的为取代或未取代的芳族环系、取代或未取代的杂芳族环系中的任意一种;R1、R2、R3、R4、Ra和Rb各自独立地选自氢、氘、卤素、C(=O)RX、CN、Si(RX)、P(=O)(RX)、ORX、S(=O)RX、S(=O)2RX、羰基、具有1~50个碳原子的烷基或烷氧基、具有3~50个碳原子的环烷基、具有2~50个碳原子的烯基或炔基、芳族环系、杂芳族环系;其中所述的烷基、烷氧基、烯基、炔基、芳族环系和杂芳族环系包含各自被一个或者多个RX基团取代后所得基团;所述的烷基、烷氧基、烯基和炔基还包括一个或者多个CH2基团被-RXC=CRX-、-C≡C-、Si(RX)2、C=O、C=NRX、-C(=O)O-、-C(=O)NRX-、P(=O))(RX)、-O-、-S-、SO或者SO2代替后所得基团;
所述RX各自独立的选自氢、氘、卤素、CN、取代或未取代的具有1~50个碳原子的烷基基团、取代或未取代的芳族环系和取代或未取代的杂芳族环系;
j和k为整数,j≥0,k≥0,j个Ra相互独立,k个Rb相互独立。j和k为整数,j≥0,k≥0,j个Ra相互独立,k个Rb相互独立。
进一步,相邻的辅助配体Ⅰ之间、主配体Ⅱ之间以及辅助配体Ⅰ、主配体Ⅱ之间通过共价键或-(W)z-的桥基连接成四齿配体或六齿配体;所述的W为C、N、O、S、Se、CR5R6、CR7、NR8、DR9R10、羰基、取代或非取代的芳族环系、取代或未取代的杂芳族环系或环烷基中的任意一种,z≥1,且为整数;z个W相互独立;
其中,D为C、Si或Ge;R5、R6、R7、R8、R9、R10各自独立的选自氢、氘、卤素、C(=O)RY、CN、Si(RY)、P(=O)(RY)、ORY、S(=O)RY、S(=O)2RY、羰基、具有1至50个碳原子的烷基或烷氧基、具有3至50个碳原子的环烷基、具有2~50个碳原子的烯基或炔基、芳族环系、杂芳族环系;其中所述的烷基、烷氧基、烯基、炔基、芳族环系和杂芳族环系包含各自被一个或者多个RX基团取代后所得基团;所述的烷基、烷氧基、烯基和炔基还包括一个或者多个CH2基团被-RYC=CRY-、-C≡C-、Si(RY)2、C=O、C=NRY、-C(=O)O-、-C(=O)NRY-、P(=O))(RY)、-O-、-S-、SO或者SO2代替后所得基团;
所述RY各自独立的选自氢、氘、卤素、CN、取代或未取代的具有1~50个碳原子的烷基基团、取代或未取代的芳族环系和取代或未取代的杂芳族环系。
进一步,两个或多个相邻的R1、R2、R3和R4之间连接形成环状基团,多个Ra之间、Rb之间以及Ra和Rb之间连接形成环状基团。
进一步,所述辅助配体Ⅰ优选如下结构:
进一步,所述主配体Ⅱ优选如下结构:
进一步,所述过渡金属配合物优选如下分子结构:
以上述的配合物Ir4和Ir5为例,通过密度泛函理论对其电子结构进行了分析。密度泛函理论计算中采用的是B3PW91泛函,对金属Ir使用LANL2DZ赝势基组,对C,N,O,H,S则使用6-31G**基组。
结果表明,Ir4的最高占据轨道(HOMO)主要分布在配体I上,比HOMO低一级的轨道(HOMO-1)则主要分布在配体Ⅱ上;最低空轨道(LUMO)和更高一级的空轨道(LUMO+1)主要分布在配体Ⅱ上,如图1所示。这表明,配体I对配合物Ir4的激发态有很大贡献,通过I可以影响和调节发光材料的光电性质。
配合物Ir5跟Ir4的电子结构相似,HOMO主要分布在I配体上,LUMO主要分布在配体Ⅱ上,如图2所示。
在本发明上下文中所述的芳族环系是指包含6~50个芳族环原子且不包含任何杂原子作为芳族环原子的芳香族环。因此,在本发明上下文中的芳族环系不包含任何杂芳基基团。在本发明上下文中的芳族环系指的是体系,其不必仅含有芳基基团,还可以是多个芳基基团通过单键或非芳族单元键合。例如,两个或更多芳族基团通过直链烷基、环烷基、烯基、炔基或甲硅烷基、B、C、Si、N、O或S原子等连接的体系,如9’9-螺二芴、9’9-二芳基芴、三芳基胺、二芳基醚、二苯乙烯、三苯基硅烷的体系同样被认为是包含在本发明上下文中的芳族环系之中。此外,其中两个或更多个芳基基团通过单键彼此连接的体系也被认为是包含在本发明上下文中的芳族环系内,例如,诸如联苯、三联苯、苯连萘的体系。
在本发明的上下文中的杂芳族环系是指包含5~50个芳族环原子且其中至少一个是杂原子的芳香族环。杂芳族环体系的杂原子优选B、N、O或S。杂芳族环系符合上述芳族环系的定义,但具有至少一个杂原子作为芳族环原子之一。以此种方式,其不同于在本申请定义的意义上的芳族环系。
在本发明上下文中的芳基基团是指含有6~50个芳族环原子,且都不是杂原子。在本发明上下文中的芳基基团是指简单的芳族环,即苯,或稠合芳族环,如萘、菲或者蒽等。在本申请上下文中的稠合芳族环由彼此稠合的两个或者更多个简单芳族环组成。环之间稠合在这里是指所述环彼此公用至少一个边。
本发明上下文中的杂芳基基团是指含有5~40个芳族环原子,且其中至少有一个是杂原子。杂芳基基团的杂原子优选B、N、O或S。在本发明上下文中的杂芳基基团是指简单的杂芳族环,例如吡啶、呋喃、噻吩、嘧啶等,或稠合杂芳族多环,例如喹啉、咔唑、苯并呋喃、二苯并噻吩等。在本申请上下文中的稠合杂芳族多环是指由彼此稠合的两个或更多个简单的杂芳族环彼此稠合所得基团,或一个或多个简单的杂芳族环和一个或多个简单芳族环稠合所得基团。环之间稠合是指所述环彼此共用至少一个边。
具有6~50个环原子的芳族环系或者具有5~50个环原子的杂芳族环系是指衍生自以下的基团:上文在芳基基团和杂芳基基团中提及的基团,以及联苯、三联苯、四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、茚并芴、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、茚并咔唑或者上述基团的组合。
各自可被上述基团取代并且可经由任何希望的位置与芳族或杂芳族体系连接的芳基或者杂芳基基团,可以理解为是指衍生自如下物质的基团:苯、萘、蒽、菲、芘、二氢芘、三亚苯、荧蒽、苯并蒽、苯并菲、并四苯、并五苯、苯并芘、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异奎琳、吖啶、菲碇。
本发明的上下文中具有2至50个碳原子的烷基、3~50个碳原子的环烷基和具有2~50个碳原子的烯基或炔基基团优选地被理解为甲基、乙基、正丙基、异丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基基团,各个基团中单独的氢原子或者CH2基团也可被上述基团所取代。
本发明的上下文中具有1至50个碳原子的烷氧基或硫代烷基基团优选被理解为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基、2,2,2-三氟乙氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、正戊硫基、仲戊硫基、正己硫基、环己硫基、正庚硫基、环庚硫基、正辛硫基、环辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、环戊烯硫基、己烯硫基、环己烯硫基、庚烯硫基、环庚烯硫基、辛烯硫基、环辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基,各个基团中单独的氢原子或者CH2基团也可被上述基团所取代。
在本申请的上下文中,两个或更多个基团一起可形成环的措词应理解为两个基团通过化学键彼此连接。上述措词也应理解为是指,如果两个基团之一是氢,则第二基团结合于氢原子所键合的位置,从而成环。
本发明提供的过渡金属配合物的有益效果是:
本发明的过渡金属配合物中含有一类新型辅助配体Ⅰ,该配体不仅有着与常用的乙酰丙酮一样的辅助配位作用,而且其轨道对过渡金属配合物的前线轨道有很大贡献,该配体与主配体Ⅱ相搭配,使得该过渡金属配合物发射光的波长可以从天蓝光到深红光进行调节,进而可调节其光电性能。
本发明还要求保护使用上述过渡金属配合物的有机电致发光器件,包括阳极层、阴极层和位于阳极层、阴极层之间的功能层,功能层中包含前述的过渡金属配合物。
进一步,所述功能层是指发光层。
进一步,所述发光层包括主体发光材料和客体发光材料,本发明提供的过渡金属配合物作为客体发光材料。
附图说明
图1为Ir4的密度泛函理论分析结果;
图2为Ir5的密度泛函理论分析结果;
图3为应用例1~6的发光光谱分析图。
具体实施方式
以下结合实例对本发明的原理和特征进行描述,所举实例只用于解释本发明,并非用于限定本发明的范围。
一、过渡金属配合物的合成实施例
实施例1:
配体Ⅰ-A的合成,反应方程式如下:
1)将三叔丁基膦(4.4ml的1.0mol/L的甲苯溶液,1.48g,0.05mmol)、醋酸钯(0.4g,1.83mmol)和叔丁醇钠(52.7g,,549mmol)添加至2-氨基恶唑(A1,16.8g,200mmol)和2-溴恶唑(A2,29.4g,200mmol)的甲苯溶液(500ml)中,并且将该混合物在回流下加热2小时。再将反应混合物冷却至室温,用甲苯稀释并且经由硅藻土过滤。再将该滤液用水稀释,并用甲苯提取,合并有机相,将其在真空下进行蒸发。将残余物经硅胶进行过滤,然后重结晶得到中间体二恶唑胺A3(19.6g,130mmol)。
2)将二恶唑胺A3溶解在500ml四氢呋喃溶液中,置入冰浴中,缓慢滴加正丁基(12.5g,195mmol)进行搅拌,缓慢恢复到室温,持续搅拌2小时,得到二恶唑-2基-胺基锂A4的溶液。
A4的阴离子部分与配体I-A互为共振结构,所以它们对应的是同一物质,如下式所示。
实施例2:
配体Ⅰ-B的合成反应方程式如下:
参照合成配体I-A的方法,将2-氨基恶唑(A1)和2-溴恶唑(A2)更换成2-氨基噻唑(B1)和2-溴噻唑(B2),相同的反应条件反应依次得到二噻唑胺B3和二噻唑-2基-胺基锂B4。
B4的阴离子部分与配体I-A互为共振结构,所以它们对应的是同一物质。
实施例3:
铱配合物Ir4的合成,反应方程式如下:
(1)合成氯桥二聚体
(2)目标物合成
具体操作过程如下:
1)将配体2-苯基吡啶(Ⅱ-A,31.0g,200mmol)、水合三氯化铱(26.7g,75.7mmol)、水150ml、乙二醇甲醚400ml、氮气氛围下搅拌回流反应24小时,后反应液冷却至室温,过滤,依次用水、乙醇和丙酮淋洗,抽干后自然晾干得到草绿色氯桥化合物II-A-Cl;
2)将II-A-Cl加入到二恶唑-2基-胺基锂A4的四氢呋喃溶液中,在80℃下搅拌,反应16小时,冷却至室温,分液,有机相用水洗至中性,硫酸镁干燥,过滤,减压浓缩,残留物用柱层层析纯化得到绿色化合物Ir4。
实施例4:
铱配合物Ir5的合成,参照实施例3的反应过程,将实施例3步骤2)中的二恶唑-2基-胺基锂A4替换为二噻唑-2基-胺基锂B4,即可反应得到铱配合物Ir5。
实施例5:
铱配合物Ir16的合成,参照实施例3的反应过程,将实施例3步骤1)中的配体2-苯基吡啶Ⅱ-A替换为1-苯基异喹啉Ⅱ-B,即可反应得到铱配合物Ir16,1-苯基异喹啉Ⅱ-B的结构如下式所示。
实施例6:
铱配合物Ir17的合成,参照实施例3的反应过程,不同之处在于将步骤1)中的配体2-苯基吡啶Ⅱ-A替换为1-苯基异喹啉Ⅱ-B,同时将步骤2)中用到的配体二恶唑-2基-胺基锂A4替换为二噻唑-2基-胺基锂B4,即可反应得到铱配合物Ir17。
实施例7:
铱配合物Ir28的合成,参照实施例3的反应过程,不同之处在于将步骤1)中的配体2-苯基吡啶Ⅱ-A替换为3-苯基异喹啉Ⅱ-C,即可反应得到铱配合物Ir17,3-苯基异喹啉Ⅱ-C结构如下式所示。
实施例8:
铱配合物Ir29的合成,参照实施例3的反应过程,不同之处在于将步骤1)中的配体2-苯基吡啶Ⅱ-A替换为3-苯基异喹啉Ⅱ-C,同时将步骤2)中用到的配体二恶唑-2基-胺基锂A4替换为二噻唑-2基-胺基锂B4,即可反应得到铱配合物Ir29。
实施例9:
铂配合物Pt4的合成,反应方程式如下:
(1)合成氯桥二聚体
(2)目标物合成
具体操作过程如下:
1)将1.86g(12mmol)2-苯基吡啶II-A的2-乙氧乙醇溶液(210ml)加入到K2PtCl4的水溶液(30ml)中。惰性气体保护下,升温至80℃,反应48h,过滤,依次用水(50ml),甲醇(150ml)洗涤,干燥,得到3.5g II-B-Cl,产率75%。
2)C4的合成与实施例1)的合成方法相同,不同之处在于反应物分别为C1和C2反应生成C3,C3反应生成C4。C1、C2、C3、C4的结构式如下所示。
3)将1.72g(9.35mmol)C4的二氯甲烷溶液(150ml)加入到溶解有0.35g(0.45mmol)II-B-Cl的二氯甲烷溶液(50ml)中,室温条件下搅拌180小时。TLC显示反应完全后,过滤,减压脱溶剂,重结晶后得产物Pt4。
实施例10:
铂配合物Pt5的合成,参照实施例9反应过程,不同之处在于,将步骤1)中的配体2-苯基吡啶Ⅱ-A替换为3-苯基异喹啉Ⅱ-C,同时将步骤3)中的C4替换为B4,即可反应得到铂配合物Pt5。
二、有机电致发光器件应用实施例
应用实施例中使用到的化合物结构式如下:
应用例1~7的有机电致发光器件的制备过程如下:
1)在玻璃底衬1上沉积一层厚度为100nm的氧化铟锡(ITO)作为透明阳极层2;
2)在透明阳极层2上真空蒸镀厚度为10nm的NPB(N,N’-二(1-萘基)-N,N’-二苯基-1,1’-联苯-4-4’-二胺)空穴传输材料作为空穴注入层3,其中掺杂质量比3%的F4-TCNQ(2,3,5,6-四氟-7,7',8,8'-四氰二甲基对苯醌);
3)空穴注入层3上为一层厚度为100nm的spiro-TAD(2,2',7,7'-四(二苯基氨基)-9,9'-螺双芴)作为空穴传输层4;
4)在空穴传输层4上真空蒸镀一层厚度为40nm的发光层5,发光层包括主体发光材料和客体发光材料,应用例1~7的主体发光材料均为CBP(4,4'-二(9-咔唑)联苯),铱配合物Ir4、Ir5、Ir15、Ir16、Ir28、Ir29或Pt4作为客体发光材料,发光层中客体发光材料的质量分数为6wt%;
5)再在发光层5上依次真空蒸镀一层厚度为30nm的TPQ(2,3,5,8-四苯基喹喔啉)作为电子传输层6;
6)于电子传输层上真空蒸镀厚度为1nm的LiF作为电子注入层7;
7)最后在电子注入层7上采用真空蒸镀膜沉积技术沉积厚度为100nm的金属铝(Al)作为器件的阴极层8。
应用例1~7所得的有机电致发光器件的发光光谱图如图3所示,性能测试结果如表1所示。
表1应用例1~7的有机电致发光器件的性能测试结果
以上所述仅为本发明的较佳实施例,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (9)
1.一类用作磷光材料的过渡金属配合物,其特征在于,具有如式(1)所示的分子结构:
式(1)中,M为过渡金属Ir、Pd或Pt中的任意一种,M右侧为辅助配体Ⅰ,M左侧为主配体Ⅱ,n和m均为大于等于1的整数;
其中,辅助配体I中的Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8和Y9各自独立的为C、N、O、S、Se、CR1、CR2R3或NR4;主配体Ⅱ中的X1、X2、X3、X4各自独立的为N或C,Ar1环和Ar2环各自独立的为取代或未取代的芳族环系、取代或未取代的杂芳族环系中的任意一种;R1、R2、R3、R4、Ra和Rb各自独立地选自氢、氘、卤素、C(=O)RX、CN、Si(RX)、P(=O)(RX)、ORX、S(=O)RX、S(=O)2RX、羰基、具有1~50个碳原子的烷基或烷氧基、具有3~50个碳原子的环烷基、具有2~50个碳原子的烯基或炔基、芳族环系、杂芳族环系;其中所述的烷基、烷氧基、烯基、炔基、芳族环系和杂芳族环系包含各自被一个或者多个RX基团取代后所得基团;所述的烷基、烷氧基、烯基和炔基还包括一个或者多个CH2基团被-RXC=CRX-、-C≡C-、Si(RX)2、C=O、C=NRX、-C(=O)O-、-C(=O)NRX-、P(=O))(RX)、-O-、-S-、SO或者SO2代替后所得基团;
所述RX各自独立的选自氢、氘、卤素、CN、取代或未取代的具有1~50个碳原子的烷基基团、取代或未取代的芳族环系、取代或未取代的杂芳族环系;
j和k为整数,j≥0,k≥0,j个Ra相互独立,k个Rb相互独立。
2.根据权利要求1所述的过渡金属配合物,其特征在于,相邻的辅助配体Ⅰ之间、主配体Ⅱ之间以及辅助配体Ⅰ、主配体Ⅱ之间通过共价键或-(W)z-的桥基连接成四齿配体或六齿配体;所述的W为C、N、O、S、Se、CR5R6、CR7、NR8、DR9R10、羰基、取代或非取代的芳族环系、取代或未取代的杂芳族环系或环烷基中的任意一种,z≥1,且为整数;z个W相互独立;
其中,D为C、Si或Ge;R5、R6、R7、R8、R9、R10各自独立的选自氢、氘、卤素、C(=O)RY、CN、Si(RY)、P(=O)(RY)、ORY、S(=O)RY、S(=O)2RY、羰基、具有1至50个碳原子的烷基或烷氧基、具有3至50个碳原子的环烷基、具有2~50个碳原子的烯基或炔基、芳族环系、杂芳族环系;其中所述的烷基、烷氧基、烯基、炔基、芳族环系和杂芳族环系包含各自被一个或者多个RX基团取代后所得基团;所述的烷基、烷氧基、烯基和炔基还包括一个或者多个CH2基团被-RYC=CRY-、-C≡C-、Si(RY)2、C=O、C=NRY、-C(=O)O-、-C(=O)NRY-、P(=O))(RY)、-O-、-S-、SO或者SO2代替后所得基团;
所述RY各自独立的选自氢、氘、卤素、CN、取代或未取代的具有1~50个碳原子的烷基基团、取代或未取代的芳族环系和取代或未取代的杂芳族环系。
3.根据权利要求1或2所述的过渡金属配合物,其特征在于,两个或多个相邻的R1、R2、R3和R4之间连接形成环状基团,多个Ra之间、Rb之间以及Ra和Rb之间连接形成环状基团。
4.根据权利要求1或2所述的过渡金属配合物,其特征在于,所述辅助配体Ⅰ的具体结构如下:
5.根据权利要求1或2所述的过渡金属配合物,其特征在于,所述主配体Ⅱ的具体结构如下:
6.根据权利要求1或2所述的过渡金属配合物,其特征在于,具有如下所示的分子结构:
7.一种有机电致发光器件,包括阳极层、阴极层和位于阳极层、阴极层之间的功能层,其特征在于,所述功能层中包含权利要求1~6任一项所述的过渡金属配合物。
8.根据权利要求7所述的有机电致发光器件,其特征在于,所述功能层是指发光层。
9.根据权利要求8所述的有机电致发光器件,其特征在于,所述发光层包括主体发光材料和客体发光材料,权利要求1~6任一项所述的过渡金属配合物作为客体发光材料。
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