CN109980111B - 一种含四齿铂(ii)配合物的有机电致发光器件 - Google Patents
一种含四齿铂(ii)配合物的有机电致发光器件 Download PDFInfo
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- CN109980111B CN109980111B CN201811567622.7A CN201811567622A CN109980111B CN 109980111 B CN109980111 B CN 109980111B CN 201811567622 A CN201811567622 A CN 201811567622A CN 109980111 B CN109980111 B CN 109980111B
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- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000000463 material Substances 0.000 claims abstract description 16
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- 239000012044 organic layer Substances 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
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- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000005266 diarylamine group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- -1 cyano, carboxyl Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
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- 125000001424 substituent group Chemical group 0.000 description 8
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 4
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- 125000003342 alkenyl group Chemical group 0.000 description 4
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- 238000002347 injection Methods 0.000 description 4
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- 239000003446 ligand Substances 0.000 description 4
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- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101000687716 Drosophila melanogaster SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 homolog Proteins 0.000 description 3
- 101000687741 Mus musculus SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 Proteins 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
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- 239000000243 solution Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
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- 229910019029 PtCl4 Inorganic materials 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
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Abstract
Description
技术领域
本发明涉及一种含新型N^N^N^O四齿铂(II)配合物金属有机材料的OLED发光器件。
背景技术
有机发光二极管(OLED,Organic Light-Emitting Diode)显示技术自发现以来,因其具有能耗低、视角大、可柔性化等独特的性能一直受到广泛的关注与研究,近些年来更是在手机、电视、笔记本电脑等电子产品上逐步应用。但是与传统的显示技术相比,OLED存在使用寿命短、色彩纯度差、易老化等缺点导致其成本居高不下,阻碍了OLED技术的推广与发展。因此,如何设计新型的OLED材料,则是OLED领域研究的重点与难点。
在OLED材料领域,磷光OLED材料发展较为迅速与成熟。磷光OLED材料主要是基于一些重金属有机配合物,如铱、铂、铕、锇等。磷光材料在发光过程中可以充分利用单线态和三线态激子的能量,因此理论上其量子效率可达到100%,这大大提高了OLED器件的发光效率,是目前业界使用比较广的发光材料。
其中,近些年来基于铂(II)的磷光OLED材料在逐步发展并取得了较好的研究成果。铂(II)一般为四配位点,因而可以通过设计四齿配体形成具有唯一构型的金属有机铂(II)配合物。一般而言,常见的四齿配体主要有O^N^N^O(如式(1)),O^N^C^O(如式(2))类型,
其中,O^N^N^O类四齿铂(II)配合物主要为席夫碱(Schiff base)类,较为常见,但稳定性相对较差;O^N^C^O类四齿铂(II)配合物相对较为稳定,但性能有待提升。
发明内容
针对上述领域的缺陷,本发明一种含四齿铂(II)配合物的有机电致发光器件,发光性能好,同时具有较好的稳定性。
一种含四齿铂(II)配合物的有机电致发光器件,包括阳极,阴极和中间有机层,所述有机层中至少包括有发光层,其中发光层中含有式(3)所示结构的四齿铂(II)配合物作为磷光掺杂材料,
其中,A1-A5为取代的或非取代的五元环、六元环、稠环结构。
优选:如式(4)所示的结构:
其中R1-R17独立的选自氢、氘、卤素、羟基、酰基、烷氧基、酰氧基、氨基、硝基、酰基氨基、氰基、羧基、苯乙烯基、氨基羰基、氨基甲酰基、苄基羰基、芳氧基、二芳胺基、含1-30个C原子的饱和烷基、含1-20个C原子的不饱和烷基、含5-30个C原子取代的或未取代的芳基、含5-30个C原子取代的或未取代的杂芳基、或者相邻R1-R17相互通过共价键连接成环;其中,X1-X27为碳,所述卤素为F,Cl,Br。
优选:其中R1-R17独立的选自氢、卤素、氨基、硝基、氰基、二芳胺基、含1-10个C原子的饱和烷基、含5-20个C原子的被卤素或一个或多个C1-C4烷基取代的或未取代芳基、含5-20个C原子的被卤素或一个或多个C1-C4烷基取代的或未取代杂芳基、或者相邻R1-R17相互通过共价键连接成环,所述卤素为F,Cl。
优选:为下列结构
其中R1’-R5’独立的选自氢、卤素、二芳胺基、含1-10个C原子的饱和烷基、含5-10个C原子的被卤素或一个或多个C1-C4烷基取代的或未取代芳基、含5-10个C原子的被卤素或一个或多个C1-C4烷基取代的或未取代杂芳基、或者相邻R1’-R5’相互通过共价键连接成环。
优选:R1’-R5’的5个基团中,其中有0-3个基团独立的表示为二芳胺基、含5-10个C原子被卤素或一至三个C1-C4烷基取代的或未取代的芳基、含5-10个C原子的被卤素或一至三个C1-C4烷基取代的或未取代的杂芳基;其它的基团独立的表示为氢或含1-8个C原子的饱和烷基,所述卤素为F。
优选:R1’-R5’的5个基团中,其中有0-3个基团独立的表示为二苯胺基、苯、吡啶、咔唑基,其它基团独立的表示为氢、异丙基或叔丁基。
为了本申请的目的,除非另有指明,术语卤素、烷基、烯基、芳基、酰基、烷氧基和杂环芳族体系或杂环芳族基团可有以下含义:
上述卤素或卤代包括氟、氯、溴和碘,优选F,Cl,Br,特别优选F或Cl,最优选F。
上述通过共价键连接成环、芳基、杂芳基包括具有5-30个碳原子,优选5-20个碳原子,更优选5-10个碳原子并且由一个芳环或多个稠和的芳环组成的芳基。适宜的芳基为,例如苯基,萘基,苊基(acenaphthenyl),二氢苊基(acenaphthenyl),蒽基、芴基、菲基(phenalenyl)。该芳基可为未取代的(即所有能够取代的碳原子带有氢原子)或在芳基的一个、多于一个或所有可取代的位置上被取代。适宜的取代基为例如卤素,优选F、Br或Cl;烷基,优选具有1-20个,1-10个或1-8个碳原子的烷基,特别优选甲基、乙基、异丙基或叔丁基;芳基,优选可再次被取代的或是未取代C5,C6芳基或芴基;杂芳基,优选含至少一个氮原子的杂芳基,特别优选吡啶基;芳基尤其特别优选带有选自F和叔丁基的取代基,优选可为给定的芳基或任选被至少一个上述取代基取代的为C5,C6芳基的芳基,C5,C6芳基特别优选带有0、1或2个上述取代基,C5,C6芳基尤其特别优选未取代的苯基或取代的苯基,诸如联苯基、被两个叔丁基优选在间位取代的苯基。
含1-20个C原子的不饱和烷基,优选烯基,更优选具有一个双键的烯基,特别优选具有双键和1-8个碳原子的烯基。
上述烷基包括具有1-30个碳原子,优选1-10个碳原子,优选1-4个碳原子的烷基。该烷基可为支链或直链的,也可以是环形的,并且可被一个或多个杂原子,优选N、O或S间断。而且,该烷基可被一个或多个卤素或上述的关于芳基的取代基所取代。同样,对于烷基而言,带有一个或多个芳基是可能的,所有上述的芳基均适用于该目的,烷基特别优选自甲基、乙基、异丙基、正丙基、异丁基、正丁基、叔丁基、仲丁基、异戊基、环丙基、环戊基、环己基。
上述酰基是以单键连接至CO基团的,如本文所用的烷基。
上述烷氧基是以单键与氧直接相连的,如本文所用的烷基。
上述杂芳基团被理解为与芳族、C3-C8环基相关,并且还包含一个氧或硫原子或1-4个氮原子或一个氧或硫原子与最多两个氮原子的组合,和他们的取代的以及苯并和吡啶并稠和的衍生物,例如,经由其中一个成环碳原子相连,所述杂芳基团可被一个或多个提到的关于芳基的取代基所取代。
在某些实施方案中,杂芳基可为携带以上独立的含有0、1或2个取代基的五、六元芳族杂环体系。杂芳基的典型实例包括但不限于未取代的呋喃、苯并呋喃、噻吩、苯并噻吩、吡咯、吡啶、吲哚、唑、苯并唑、异唑、苯并异唑、噻唑、苯并噻唑、异噻唑、咪唑、苯并咪唑、吡唑、吲唑、四唑、喹啉、异喹啉、哒嗪、嘧啶、嘌呤和吡嗪、呋喃、1,2,3-二唑、1,2,3-噻二唑、1,2,4-噻二唑、三唑、苯并三唑、喋啶、苯并唑、二唑、苯并吡唑、喹嗪、噌啉、酞嗪、喹唑和喹喔啉及其单-或二-取代的衍生物。在某些实施方案中,取代基为卤代、羟基、氰基、O-C1~6烷基、C1~6烷基、羟基C1~6烷基和氨基-C1~6烷基。
如下所示的具体实例,包括但不限于以下结构:
上述配合物的制备方法,包括如下步骤:
如下所示,咔唑类衍生物S1经溴代反应得到底物S2,S2与联硼酸频哪醇酯反应得到相应的频哪醇酯衍生物S3,S3与吡啶类衍生物S4经Suzuki反应得到S5,S5与吡啶类衍生物S6经Suzuki反应得到S7,S7脱甲基后得到相应的配体S8,S8与K2PtCl4反应即得到目标产物P。
其中,R'1~R'5为芳香或非芳香取代基。
该N^N^N^O四齿铂(II)配合物可以用于OLED发光器件中,在发光层中起光子发射作用的磷光掺杂材料。所述四齿铂(II)配合物的掺杂量为1%-12%。优选4%-8%。
采用具有上述结构的铂(II)配合物,可制造热沉积和溶液处理的OLED器件。
包括含有一种或多种配合物的有机发光器件。
其中通过热沉积在该器件中以层形式施加该配合物。
其中通过旋涂在该器件中以层形式施加该配合物。
其中通过喷墨打印在该器件中以层形式施加该配合物。
上述有机发光器件,在施加电流时该器件发射为橙红色。
本发明中的铂(II)配合物具有高荧光量子效率,良好的热稳定性及低淬灭常数,可以制造高发光效率、低滚降的橙红色光OLED器件。
附图说明
图1本发明有机电致发光器件结构示意图。
具体实施方式
下面结合实施例对本发明做进一步的详细说明。
实施例1:
合成路线:
化合物2的合成:取6.50g(20.0mmol)化合物1,联硼酸频哪醇酯12.70g(2.5eq.,50.0mmol),碳酸钾5.18g(2.5eq.,50.0mmol)和Pd(dppf)Cl2 292mg(0.02eq.,0.4mmol),加入到三颈烧瓶中,抽真空通入氮气置换多次,然后注入乙腈二氧六环150mL,加热至85℃。在氮气保护下反应12hr后,冷却至室温,旋蒸除去溶剂,再加入适量水和乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体7.12g,产率85%,纯度99.0%。
化合物3的合成:取11.85g(50.0mmol)化合物2,6-二溴吡啶,2-甲氧基苯硼酸7.60g(1.0eq.,50.0mmol),碳酸钾6.48g(1.25eq.,62.5mmol)和Pd(OAc)2 224mg(0.02eq.,1mmol),PPh3 1.31g(0.1eq.,5mmol)加入到三颈烧瓶中,抽真空通入氮气置换多次,然后注入乙腈150mL,甲醇50mL,加热至60℃。在氮气保护下反应12hr后,冷却至室温,旋蒸除去溶剂,再加入适量水和乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体9.90g,产率75%,纯度99.5%。
化合物4的合成:取6.29g(15.0mmol)化合物2,化合物3 3.96g(1.0eq.,15.0mmol),碳酸钾3.45g(1.25eq.,25.0mmol)和Pd(PPh3)4 347mg(0.02eq.,0.3mmol),加入到三颈烧瓶中,抽真空通入氮气置换多次,然后注入乙腈100mL和50mL甲醇,加热至60℃。在氮气保护下反应12hr后,冷却至室温,旋蒸除去溶剂,再加入适量水和乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体4.28g,产率60%,纯度99.5%。
化合物5的合成:取3.81g(8.0mmol)化合物4,2-溴吡啶1.37g(1.1eq.,8.8mmol),碳酸钾1.38g(1.25eq.,10.0mmol)和Pd(PPh3)4 185mg(0.02eq.,0.16mmol),加入到三颈烧瓶中,抽真空通入氮气置换多次,然后注入乙腈60mL和30mL甲醇,加热至60℃。在氮气保护下反应12hr后,冷却至室温,旋蒸除去溶剂,再加入适量水和乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体3.07g,产率90%,纯度99.9%。
化合物6的合成:取2.14g(4.0mmol)化合物5,吡啶盐酸盐30g(PyHCl),加入到三颈烧瓶中,抽真空通入氮气置换多次,在氮气保护下加热至190℃,反应4hr后,冷却至室温,再加入适量水和乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体1.32g,产率80%,纯度99.9%。质谱(ESI-)([M-H]-)C28H18N3O理论值:412.15;实测值:412.13。
化合物P1的合成:取826mg(2.0mmol)化合物5和328mg无水醋酸钠(2.0eq.,4.0mmol)溶于25mL DMSO中,搅拌,加热至80℃,然后加入四氯铂酸钾830mg(1.0eq.,2.0mmol),抽真空通入氮气置换数次,升温到120℃反应5hr。反应结束后,趁热加入100ml水,过滤,收集固体,用适量水和甲醇洗涤,将得到的固体用甲苯重结晶,然后真空升华得到深红色固体788mg,总产率65%,纯度99.9%。质谱(ESI-)([M-H]-)C28H16N3OPt理论值:605.10;实测值:605.08。
实施例2:
合成路线:
化合物7的合成:取16.72g咔唑(0.10mol)和655mg无水三氯化铝(5mmol)于三颈烧瓶中,抽真空通入氮气置换多次,然后滴加氯代叔丁烷27.77g(3.0eq.,0.30mmol)和干燥的二氯甲烷250mL,在氮气保护下搅拌反应12hr后,再加入适量水萃取,收集有机相,旋蒸除去溶剂,将得到的固体使用乙醇重结晶,得到白色固体23.20g,产率83%,纯度99.5%。
化合物8的合成:取13.97g(50.0mmol)化合物7,溶于750mL醋酸中,然后滴入液溴19.98g(2.5eq.,125.0mmol),遮光反应。室温搅拌约4hr后,旋蒸除去溶剂,再加入适量水和亚硫酸氢钠溶液洗涤,乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体20.77g,产率95%,纯度99.9%。
化合物9的合成:取10.93g(25.0mmol)化合物8,联硼酸频哪醇酯15.88g(2.5eq.,62.5mmol),碳酸钾8.64g(2.5eq.,62.5mmol)和Pd(dppf)Cl2 366mg(0.02eq.,0.5mmol),加入到三颈烧瓶中,抽真空通入氮气置换多次,然后注入二氧六环300mL,加热至85℃。在氮气保护下反应12hr后,冷却至室温,旋蒸除去溶剂,再加入适量水和乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体9.56g,产率72%,纯度99.9%。
化合物10的合成:取7.97g(15.0mmol)化合物9,化合物3 3.96g(1.0eq.,15.0mmol),碳酸钾3.45g(1.25eq.,25.0mmol)和Pd(PPh3)4 347mg(0.02eq.,0.3mmol),加入到三颈烧瓶中,抽真空通入氮气置换多次,然后注入乙腈100mL和50mL甲醇,加热至60℃。在氮气保护下反应12hr后,冷却至室温,旋蒸除去溶剂,再加入适量水和乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体5.74g,产率65%,纯度99.9%。
化合物11的合成:取4.71g(8.0mmol)化合物10,2-溴吡啶1.37g(1.1eq.,8.8mmol),碳酸钾1.38g(1.25eq.,10.0mmol)和Pd(PPh3)4 185mg(0.02eq.,0.16mmol),加入到三颈烧瓶中,抽真空通入氮气置换多次,然后注入乙腈60mL和30mL甲醇,加热至60℃。在氮气保护下反应12hr后,冷却至室温,旋蒸除去溶剂,再加入适量水和乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体3.67g,产率85%,纯度99.9%。
化合物12的合成:取2.16g(4.0mmol)化合物11,吡啶盐酸盐30g(PyHCl),加入到三颈烧瓶中,抽真空通入氮气置换多次,在氮气保护下加热至190℃,反应4hr后,冷却至室温,再加入适量水和乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体1.79g,产率85%,纯度99.9%。质谱(ESI-)([M-H]-)C36H34N3O理论值:524.27;实测值:524.24。
化合物P2的合成:取1.06g(2.0mmol)化合物5和328mg无水醋酸钠(2.0eq.,4.0mmol)溶于25mL DMSO中,搅拌,加热至80℃,然后加入四氯铂酸钾830mg(1.0eq.,2.0mmol),抽真空通入氮气置换数次,升温到120℃反应5hr。反应结束后,趁热加入100ml水,过滤,收集固体,用适量水和甲醇洗涤,将得到的固体用甲苯重结晶,然后真空升华得到深红色固体1.01g,总产率70%,99.9%。质谱(ESI-)([M-H]-)C36H33N3OPt理论值:717.23;实测值:717.20。
实施例3:
合成路线:
化合物14的合成:取7.97g(15.0mmol)化合物9,化合物13 7.63g(1.0eq.,15.0mmol),碳酸钾3.45g(1.25eq.,25.0mmol)和Pd(PPh3)4 347mg(0.02eq.,0.3mmol),加入到三颈烧瓶中,抽真空通入氮气置换多次,然后注入乙腈100mL和50mL甲醇,加热至60℃。在氮气保护下反应12hr后,冷却至室温,旋蒸除去溶剂,再加入适量水和乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体7.50g,产率60%,纯度99.5%。
化合物15的合成:取6.66g(8.0mmol)化合物14,2-溴吡啶1.37g(1.1eq.,8.8mmol),碳酸钾1.38g(1.25eq.,10.0mmol)和Pd(PPh3)4 185mg(0.02eq.,0.16mmol),加入到三颈烧瓶中,抽真空通入氮气置换多次,然后注入乙腈60mL和30mL甲醇,加热至60℃。在氮气保护下反应12hr后,冷却至室温,旋蒸除去溶剂,再加入适量水和乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体6.27g,产率80%,纯度99.9%。
化合物16的合成:取3.14g(4.0mmol)化合物15,吡啶盐酸盐30g(PyHCl),加入到三颈烧瓶中,抽真空通入氮气置换多次,在氮气保护下加热至190℃,反应4hr后,冷却至室温,再加入适量水和乙酸乙酯萃取,收集有机相,无水硫酸镁干燥后加入适量硅胶,旋蒸除去溶剂,使用正己烷/乙酸乙酯体系柱层析,得到白色固体2.77g,产率90%,纯度99.9%。质谱(ESI-)([M-H]-)C54H62N3O理论值:768.50;实测值:768.47。
化合物P105的合成:取1.54g(2.0mmol)化合物16和328mg无水醋酸钠(2.0eq.,4.0mmol)溶于25mL DMSO中,搅拌,加热至80℃,然后加入四氯铂酸钾830mg(1.0eq.,2.0mmol),抽真空通入氮气置换数次,升温到120℃反应5hr。反应结束后,趁热加入100ml水,过滤,收集固体,用适量水和甲醇洗涤,将得到的固体用甲苯重结晶,然后真空升华得到深红色固体1.25g,总产率65%,纯度99.9%。质谱(ESI-)([M-H]-)C54H60N3OPt理论值:961.44;实测值:961.42。
实施例的Pt(II)配合物,在二氯甲烷溶液中呈现出明显的橙红光发射,如下表所示:
下面是本发明化合物的应用实例。
器件制备方式:
器件的基本结构模型为:ITO/HTL-1(60nm)/EML-1:Pt(II)(40nm)/ETL-1(30nm)/LiF(1nm)/Al(80nm)。
依次使用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)20(10Ω/sq)玻璃基板10进行超声清洗,再用氧气等离子处理5分钟。
然后将ITO衬底安装在真空气相蒸镀设备的衬底固定器上。在蒸镀设备中,控制体系压力在10-6torr。
此后,向ITO衬底上蒸发厚度为60nm的空穴传输层30材料HTL-1。
然后蒸发厚度为40nm的发光层40材料EML-1,其中掺杂不同质量分数的铂(II)配合物掺杂剂。
然后蒸发厚度为30nm的电子传输层50材料ETL-1。
然后蒸发厚度为1nm的LiF为电子注入层60。
最后蒸发厚度为80nm的Al作为阴极70并完成器件封装。见图1所示。
测试器件的结构和制作方法完全相同,区别在于依次使用有机金属配合物Pt0、Pt1、Pt2、Pt105作为发光层中的掺杂剂和掺杂浓度。其中,Pt0为经典的O^N^N^O类红光材料。
器件对比结果下表所示:
在四齿铂(II)配合物掺杂浓度分别为4wt%,8wt%,12wt%条件下,以上述ITO/HTL-1(60nm)/EML-1:Pt(II)(40nm)/ETL-1(30nm)/LiF(1nm)/Al(80nm)器件基本结构制备器件。以基于Pt0的器件性能为参考,四齿铂(II)配合物Pt1,Pt2,Pt105的器件在启动电压Von相比Pt0的器件均有不同程度的降低,尤其是基于Pt105的器件其启动电压降至3.0V。同时,在1000cd/A条件下,基于Pt1,Pt2,Pt105的器件在电流效率(CE),功率效率(PE)和外量子效率(EQE)相对于基于Pt-0的器件均有不同程度的提升,尤其是Pt105,在电流效率(CE),功率效率(PE)和外量子效率(EQE)上提升较为明显。在四齿铂(II)配合物掺杂浓度增加时,Pt0,Pt1的效率提升较小甚至效率有一定程度的下降,但是Pt105有较好的效率提升,其电流效率由73.5cd/A提升至78.5cd/A,功率效率由67.8lm/W提升至78.5lm/W,外量子效率由17.8%提升至18.7%。Pt105相对于Pt0,Pt1,Pt2有较大的位阻基团,能有效降低分子间的聚集作用,避免形成激基复合物,提高发光效率。同时,Pt1,Pt2相对于Pt0在性能上也有不同程度的提升。
综上所述,本发明所制备的有机电致发光器件的性能相对于基准器件具有较好的性能提升,所涉及的新型N^N^N^O四齿铂(II)配合物金属有机材料具有较大的应用价值。
Claims (10)
3.根据权利要求2所述的有机电致发光器件,其中R1-R17独立的选自氢、卤素、氨基、硝基、氰基、二芳胺基、含1-10个C原子的饱和烷基、含5-20个C原子的被卤素或一个或多个C1-C4烷基取代的或未取代芳基、含5-20个C原子的被卤素或一个或多个C1-C4烷基取代的或未取代杂芳基、或者相邻R1-R17相互通过共价键连接成环,其中R1-R17中的卤素和被卤素取代中的卤素均为F,Cl。
5.根据权利要求4所述的有机电致发光器件,其中R1’-R5’的5个基团中,其中有0-3个基团独立的表示为二芳胺基、含5-10个C原子被卤素或一至三个C1-C4烷基取代的或未取代的芳基、含5-10个C原子的被卤素或一至三个C1-C4烷基取代的或未取代的杂芳基;其它的基团独立的表示为氢或含1-8个C原子的饱和烷基,所述卤素为F。
6.根据权利要求5所述的有机电致发光器件,R1’-R5’的5个基团中,其中有0-3个基团独立的表示为二苯胺基、苯、吡啶、咔唑基,其它基团独立的表示为氢、异丙基或叔丁基。
9.根据权利要求7所述的有机电致发光器件,所述四齿铂(II)配合物的掺杂量为重量百分比1%-12%。
10.根据权利要求7所述的有机电致发光器件,所述四齿铂(II)配合物的掺杂量为重量百分比4%-8%,所述四齿铂(II)配合物采用通过热沉积、旋涂、喷墨打印以层形式施加在该器件中。
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