WO2016004772A1 - 用于发光二极管的发光材料 - Google Patents

用于发光二极管的发光材料 Download PDF

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WO2016004772A1
WO2016004772A1 PCT/CN2015/074265 CN2015074265W WO2016004772A1 WO 2016004772 A1 WO2016004772 A1 WO 2016004772A1 CN 2015074265 W CN2015074265 W CN 2015074265W WO 2016004772 A1 WO2016004772 A1 WO 2016004772A1
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luminescent material
alkyl
light
independently hydrogen
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支志明
蔡丽菲
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广东阿格蕾雅光电材料有限公司
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Priority to JP2017519759A priority Critical patent/JP6258558B2/ja
Priority to DE112015003222.3T priority patent/DE112015003222B4/de
Priority to KR1020167035175A priority patent/KR101904175B1/ko
Priority to US15/325,701 priority patent/US9831449B2/en
Publication of WO2016004772A1 publication Critical patent/WO2016004772A1/zh

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Definitions

  • the present invention relates to a luminescent material, and more particularly to a novel platinum (II) complex luminescent material and its use in an organic light emitting diode (OLED).
  • II platinum
  • OLED organic light emitting diode
  • CWTang disclosed a two-layer structure OLED (Organic Light Emitting Device) (U.S. Patent No. 4,356,429; Appl. Phys. Lett. 1987, 51, 12, 913).
  • OLED Organic Light Emitting Device
  • This finding is based on the use of a multilayer structure comprising a hole transport layer of an emissive electron-transporting layer and a suitable organic material.
  • Alq 3 q: deprotonated 8-hydroxywynyl
  • a phosphorescent material is used as a light emitter in the light-emitting layer of the OLED, and among different phosphorescent materials, a tantalum-containing and platinum-bearing complex is a mainstream material. Because the tantalum material has an octahedral geometry, OLEDs made of tantalum materials generally do not have significant efficiency degradation in addition to high performance. In contrast, platinum-bearing materials have a planar geometric configuration, so OLEDs made of tantalum-containing materials can have high efficiency, but at the same time have great efficiency attenuation. In other words, these devices can only be used in extremely low brightness.
  • High performance is achieved under conditions, and under normal operating brightness, such as 1000 cd m -2 , the performance of the device generally falls to very low levels.
  • the present invention provides a novel platinum (II) complex luminescent material having a low quenching constant and capable of producing a red OLED with high efficiency and low efficiency attenuation.
  • the invention also provides a method of preparing a further luminescent material.
  • the invention also provides a light emitting device prepared from the luminescent material.
  • R 1 to R 26 are independently hydrogen, halogen, hydroxy, unsubstituted alkyl, substituted alkyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitrate group, acylamino, aralkyl, cyano, carboxy, thio, styryl group, aminocarbonyl group, a carbamoyl group, an aryloxycarbonyl group, a phenoxycarbonyl group or an alkoxycarbonyl group, R 1 -R 26 may be independently The formation forms a 5-8 membered ring with adjacent R 1 -R 26 groups.
  • R 1 -R 26 are independently hydrogen, halogen, hydroxy, C 1 -C 6 alkyl, 5- or 6-membered cycloalkyl, 5- or 6-membered aryl, alkoxy, amino, nitro, cyano
  • the group, carboxyl group, R 1 -R 26 may independently form a 5-6 membered ring with the adjacent R 1 -R 26 groups.
  • R 3-8 and R 17-22 are independently hydrogen.
  • R 1 , R 11 , R 16 and R 24 are independently hydrogen
  • R 2 , R 23 , R 9-10 and R 25-26 are independently hydrogen and C 1 -C 6 alkyl.
  • R 12-15 is independently hydrogen, halogen, hydroxy, C 1 -C 6 alkyl, 5- or 6-membered cycloalkyl, 5- or 6-membered aryl, amino, nitro, cyano, or R 13 And R 14 forms a 5-6 membered aromatic ring.
  • R 13 and R 14 are independently hydrogen, halogen, C 1 -C 4 alkyl, amino, nitro, cyano, or R 13 and R 14 form a benzene ring.
  • R 12 and R 15 are independently hydrogen and C 1 -C 6 alkyl.
  • the organometallic complex having the chemical structure of structure I is referred to as a cyclometallated complex, and the platinum center in structure I is in the +2 oxidation state and has a square planar geometry.
  • the coordination point of the platinum center is supported by a tetradentate ligand.
  • the tetradentate ligand is coordinated to the platinum center by two nitrogen donor bonds and two oxygen donor bonds.
  • four The basic structure of the tooth ligand is Schiff base. It is mentioned in the background data that since the platinum complexes with Schiff base have high quenching constants, the devices prepared by them have high efficiency attenuation, and even if a large group is added, the problem cannot be improved.
  • the double ring attached to the phenol is one of the important points, and the annihilation constant can be effectively reduced.
  • the central portion of structure I (the thick line portion in the following figures) is responsible for the material having red light and a low quenching constant:
  • R 1 -R 26 do not seriously affect the luminescent properties and quenching constants of the materials, so they can be independently hydrogen, halogen, hydroxy, unsubstituted alkyl, substituted Alkyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, acylamino, aralkyl, cyano, carboxyl, thio, styryl, Aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl or alkoxycarbonyl.
  • Each R 1 -R 26 can independently form a 5-8 membered ring with an adjacent R group.
  • halogen alkyl, cycloalkyl, aryl, acyl, alkoxy, and heterocyclic aromatic or heterocyclic aromatic groups may have the following meanings, unless otherwise indicated:
  • Halogen or halo includes fluoro, chloro, bromo and iodo, preferably F, Cl, Br, particularly preferably F or Cl, most preferably F.
  • An aryl, aryl moiety or aromatic system as used herein includes a fused ring having 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 8 carbon atoms and having one or more aromatic rings
  • An aryl group composed of an aromatic ring. Suitable aryl groups are, for example, phenyl, naphthyl, acenaphthenyl, acenaphthylenyl, fluorenyl, fluorenyl, phenalenyl.
  • the aryl group may be unsubstituted (i.e., all carbon atoms capable of substituting a hydrogen atom) or substituted at one, more than one or all substitutable positions of the aryl group.
  • Suitable substituents are, for example, halogen, preferably F, Br or Cl; alkyl groups, preferably those having from 1 to 20, from 1 to 10 or from 1 to 8 carbon atoms, particularly preferably methyl, ethyl or iso- a propyl or tert-butyl group; an aryl group, preferably a re-substituted or unsubstituted C 6 -aryl or anthracenyl group; a heteroaryl group, preferably a heteroaryl group containing at least one nitrogen atom, particularly preferably a pyridyl group
  • the alkenyl group is a suitable substituent, preferably an alkenyl group having one double bond, and particularly preferably an alkenyl group having a double bond and 1-8 carbon atoms.
  • the aryl group particularly preferably has a substituent selected from the group consisting of F and a tert-butyl group, preferably an aryl group which is a given aryl group or a C 6 -aryl group optionally substituted by at least one of the above substituents, C 6
  • the aryl group particularly preferably has 0, 1 or 2 of the abovementioned substituents
  • the C 6 -aryl group is particularly preferably an unsubstituted phenyl group or a substituted phenyl group such as a biphenyl group, preferably a two-tert-butyl group. Substituted phenyl.
  • the aryl or aryl moiety as used herein is preferably phenyl which may be unsubstituted or substituted by the above substituents, preferably halogen, alkyl or aryl.
  • the alkyl or alkyl moiety as used herein includes alkyl groups having from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms, particularly preferably from 1 to 6 carbon atoms.
  • the alkyl group may be branched or straight chain and may be interrupted by one or more heteroatoms, preferably N, O or S.
  • the alkyl group may be substituted with one or more of the substituents mentioned for the aryl group.
  • the alkyl group may carry one or more aryl groups, all of which are suitable for this purpose, the alkyl group being particularly preferably selected from the group consisting of methyl, ethyl, iso-propyl, N-propyl, iso-butyl, n-butyl, tert-butyl, sec-butyl, iso-pentyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, iso - hexyl and sec-hexyl, particularly particularly preferred are tert-butyl, C 4 H 9 , C 6 H 13 .
  • a cycloalkyl group is desirably a cyclic alkyl group, and preferred cycloalkyl groups are those having 3 to 7 carbon atoms, and include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group and the like. Further, the cycloalkyl group may be optionally substituted with one or more substituents selected from halo, alkyl, such as t-butyl, C 4 H 9 , C 6 H 13 .
  • an acyl group is an alkyl group, as used herein, attached to a CO group with a single bond.
  • an alkoxy group is an alkyl group, as used herein, attached to an oxygen.
  • a heterocyclic aromatic system or a heterocyclic aromatic group is understood to be related to an aromatic, C 3 -C 8 cyclo group, and also contains an oxygen or sulfur atom or 1-4 nitrogen atoms or a a combination of an oxygen or sulfur atom and up to two nitrogen atoms, and their substituted and benzo and pyridine-fused derivatives, for example, via one of the ring-forming carbon atoms, said heterocyclic aromatic system or The heterocyclic aromatic group may be substituted by one or more of the substituents mentioned for the aryl group.
  • a heteroaryl group can be a five- and six-membered-aromatic heterocyclic ring system that carries the same, or different, 0, 1, or 2 substituents above.
  • Typical examples of heteroaryl groups include, but are not limited to, unsubstituted furan, benzofuran, thiophene, benzothiophene, pyrrole, pyridine, hydrazine, azole, benzoxazole, isoxazole, benzisoxazole, thiazole, Benzothiazole, isothiazole, imidazole, benzimidazole, pyrazole, oxazole, tetrazole, quinoline, isoquinoline, pyridazine, pyrimidine, purine and pyrazine, furan, 1,2,3-diazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, triazole, benzotriazole, pter
  • platinum (II) complex Specific examples of the platinum (II) complex are shown below, but are not limited to the following complexes:
  • Thermally deposited and solution treated OLEDs can be fabricated using complexes with structure I.
  • An organic light emitting device comprising one or more luminescent materials for light emitting diodes as recited in claim 1 is included.
  • the luminescent material for the light-emitting diodes is applied in layers in the device by thermal deposition.
  • the luminescent material for the light-emitting diodes is applied in layers in the device by spin coating.
  • the luminescent material for the light-emitting diodes is applied in layers in the device by inkjet printing.
  • the above organic light-emitting device wherein the device emits a monochromatic-red color when a current is applied to the layer.
  • the platinum (II) complex in the present invention has high luminescence quantum efficiency, good thermal stability and low quenching constant, and can be manufactured high.
  • a red OLED that is efficient and inefficiently attenuated.
  • Figure 6 Spectrum of an OLED prepared with complex 101.
  • a chemical having a structure of structure II is obtained by a chemical reaction containing a phthalic acid group (structure III) and a chemical containing a phenol and a bicyclic ring (structure IV) by a condensation reaction to form two imine bonds. body.
  • structure III a phthalic acid group
  • structure IV a chemical containing a phenol and a bicyclic ring
  • Ligand 301 was prepared by the method of Example 201, wherein R 1 - R 26 were hydrogen. Yield: 100%.
  • the ligand having the chemical structure of structure II (301) and twice the amount of weak base are first dissolved in a small amount of hot dimethylformamide, followed by a salt containing one part of the platinum-containing salt. A methyl sulfoxide solution was added thereto. After one night of reaction, the precipitate was collected by filtration and finally purified by recrystallization.
  • the complex 101 was prepared by the method of Example 203, wherein the weak base was sodium acetate and the salt of platinum was potassium tetrachloroplatinate. Yield: 32%.
  • Example 208 - A device was prepared using Example 207, wherein the hole transport layer was 40 nm of 4,4'-cyclohexyl bis[N,N-bis(4-methylphenyl)aniline] (TAPC);
  • the luminescence consists of two different layers, the first layer is mainly the luminescent layer of tris(4-carbazol-9yl-phenyl)amine (TcTa) (host material), doped with a small amount of complex 101 (doped a second layer is a luminescent layer mainly composed of 9,9'-(2,6-pyridyldiyl-2,1-phenylene)bis-9H-carbazole (26DczPPy) (host material), doped Miscellaneous with a small amount of complex 101 (dopant);
  • the electron transport layer is 40 nm of 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3', 1"-terpheny
  • Example 209 - Example 209 illustrates the device performance of an OLED device made using the complex 101 as a luminescent material by the method described in Example 208.

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Abstract

本发明涉及用于发光二极管的发光材料，其结构如式I所示，本发明中的铂(II)络合物具有高发光量子效率，良好的热稳应性及低猝灭常数，可以制造高效率并低效率衰减的红光OLED。

Description

用于发光二极管的发光材料 技术领域
本发明涉及一种发光材料，特别是涉及一种新型铂(II)络合物发光材料及其在有机发光二极管(OLED)中的用途。
背景技术
在上世纪八十年代，C.W.Tang公开了双层结构OLED(有机发光器件)(美国专利No.4,356,429；Appl.Phys.Lett.1987,51,12,913)。这种发现基于使用包括发光电子传输层(emissive electron-transporting layer)和合适的有机材料的空穴传输层的多层结构。选择Alq3(q:脱质子8-羟基哇琳基)作为发光电子传输材料。从那时起，持续研究OLED中使用的材料OLED提供几个优点，包括：(1)低工作电压，(2)薄整体结构，(3)发射光而非调制光，(4)良好的发光效率，(5)全色潜力；和(的高对比和分辨率.这些优点表明OLED可能用在平板显示器中。
对有机小分子进行研究以改进OLED的性能。通常，使用磷光材料作为OLED的发光层中的光发射体，而在不同的磷光材料之中，带铱和带铂的络合物是主流材料。因为带铱材料有着八面体的几何配置，由带铱材料制备的OLED，除了有高效能之外，一般也不会有极大的效率衰减。相对而言，带铂的材料有着平面的几何配置，所以由带铱材料制备的OLED，虽然也可以有高效能，但却同时有极大的效率衰减，换言之这些器件只能在极低亮度的情况之下得到高效能，而在正常运作的亮度例如1000cd m-2之下，器件的效能一般也会降至十分低的水平。例如，我们在2007年开发了一类带铂的磷光材料，由这些材料制备的器件可以得到高达51.8cd A-1的效能，但是这些器件的效能急速地下跌至低于最高效能的百分之五十(Appl.Phys.Lett.91,2007,063508)。这也是导致现在只有带铱材料能够用在OLED商品上应用的一个主要原因。
一般来说，材料具有高猝灭常数(在108dm3mol-1s-1以上)会导致严重的三重态-三重态湮灭而产生快速效率衰减。除了效率衰减之外，高猝灭常数还会使带铂的材料制备的器件只能在十分窄的掺杂窗口运作。换言之，高效能及高色纯度的器件只能在一个很小的掺杂范围(例如1％-2％)达到。这也是带铂材料未能被工业界接纳的原因。
为了解决这问题，不同的学者提出了不同的方案并制备出了不同的材料。在2010年我们加了大基团，Huo加了非平面基，在2012年，Xie加了非平面基到带铂材料中(Chem.Eur.J.2010,16,233-247；Inorg.Chem.2010,49,5107–5119；Chem.Commun.2012,48,3854-3856)。但是这问 题并没有得到明显的改善，制备出来的器件还是有着高于50％的效率衰减。这证明了加入大基团及非平面基并不是通常可行的方法去解决这问题。
发明内容
针对上述领域中的缺陷，本发明提供一种新型铂(II)络合物发光材料，其具有低猝灭常数，可以制造高效率并低效率衰减的红光OLED。
本发明还提供还发光材料的制备方法。
本发明还提供该发光材料制备的发光器件。
用于发光二极管的发光材料，其结构如式I所示，
Figure PCTCN2015074265-appb-000001
其中R1-R26独立地为氢、卤素、羟基、未取代烷基、取代烷基、环烷基、未取代芳基、取代芳基、酰基、烷氧基、酰氧基、氨基、硝基、酰基氨基、芳烷基、氰基、羧基、硫代、苯乙烯基、氨基羰基、氨基甲酰基、芳氧基羰基、苯氧基羰基或烷氧基羰基，R1-R26可独立地与邻近其它的R1-R26基团形成5-8元环。
其中R1-R26独立地为氢、卤素、羟基、C1-C6烷基、五元或六元环烷基、五元或六元芳基、烷氧基、氨基、硝基、氰基、羧基、R1-R26可独立地与邻近其它的R1-R26基团形成5-6元环。
其中R3-8、R17-22独立地为氢。
其中R1、R11、R16、R24独立地为氢，R2、R23、R9-10、R25-26独立的为氢、C1-C6烷基。
其中R12-15独立的为氢、卤素、羟基、C1-C6烷基、五元或六元环烷基、五元或六元芳基、氨基、硝基、氰基，或者R13、R14形成5-6元芳环。
其中R13、R14独立的为氢、卤素、C1-C4烷基、氨基、硝基、氰基，或者R13、R14形成苯 环。
其中R12、R15独立的为氢、C1-C6烷基。
具有结构I的化学结构的有机金属络合物被称作环金属化络合物，结构I中的铂中心为+2氧化态并具有正方形平面几何形状。该铂中心的配位点被一个四齿配体.，四齿配体通过两个氮给体键和两个氧给体键键配位到铂中心上，为了达到发红光的需求，四齿配体的基本结构为希夫碱。在背景资料`中提及到由于带有希夫碱的铂络合物都具有高猝灭常数，用他们制备的器件都有高效率衰减，就算加入大基团也不能改善这问题。在本发明中，附在酚的双环是其中一个重点，能有效地减低猝灭常数。通过结构I，我们把这两个方法连在一起并得到了用其他基团得不到的效果。在这发明中，结构I中的中心部分(下列图中,粗线部分)是使材料有着发红光并有低猝灭常数的原因：
Figure PCTCN2015074265-appb-000002
而在结构I中,其他基团(R1-R26)并不会严重的影响材料的发光性质及猝灭常数，所以他们可以是独立地为氢、卤素、羟基、未取代烷基、取代烷基、环烷基、未取代芳基、取代芳基、酰基、烷氧基、酰氧基、氨基、硝基、酰基氨基、芳烷基、氰基、羧基、硫代、苯乙烯基、氨基羰基、氨基甲酰基、芳氧基羰基、苯氧基羰基或烷氧基羰基。各个R1-R26可独立地与邻近的R基团形成5-8元环。
为了本申请的目的，除非另有指明，术语卤素、烷基、环烷基、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:
本文所用的卤素或卤代包括氟、氯、溴和碘，优选F，Cl，Br，特别优选F或Cl，最优选F。
如本文所用的芳基、芳基部分或芳族体系包括具有6-30个碳原子，优选6-20个碳原子，更优选6-8个碳原子并且由一个芳环或多个稠合的芳环组成的芳基。适宜的芳基为，例如苯基，萘基,苊基(acenaphthenyl)、二氢苊基(acenaphthylenyl)，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的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，烯基是适宜的取代基，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。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C6-芳基的芳基，C6-芳基特别优选带有0、1或2个上述取代基，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。如本文所用的芳基或芳基部分优选为苯基，其可为未取代的或被上述取代基，优选卤素、烷基或芳基取代。
本文使用的烷基或烷基部分包括具有1-20个碳原子，优选1-10个碳原子，特别优1-6个碳原子的烷基。该烷基可为支链或是直链的，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提及的关于芳基的取代基取代。同样，对于烷基而言，带有一个或多个芳基是可能的，所有提到的芳基均适宜用于该目的，烷基特别优选选自甲基、乙基、异-丙基、正-丙基、异-丁基、正-丁基、叔-丁基、仲-丁基、异-戊基、正-戊基、仲-戊基、新戊基、正-已基、异-已基和仲-已基，尤其特别优选的是叔-丁基、C4H9、C6H13。
如本文所用的，环烷基期望为环形烷基，优选的环烷基为那些含3-7个碳原子的环烷基,并且包括环丙基、环戊基、环已基等。再有，环烷基可被选自卤代、烷基，诸如叔丁基、C4H9、C6H13的一个或多个取代基任选取代。
如本文所用的，酰基是以单键连接至CO基团的、如本文所用的烷基。
如本文所用的，烷氧基是与氧相连的、如本文所用的烷基。
如本文所用的，杂环芳族体系或杂环芳族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，和它们的取代的以及苯并和吡啶并-稠合的衍生物，例如，经由其中一个成环碳原子相连，所述杂环芳族体系或杂环芳族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彼此可相同或不同的0、1、或2个取代基的五-和六元-芳族杂环体系。杂芳基的典型的实例包括，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、蝶啶、苯并唑、二唑、苯并吡唑、喹嗪、噌啉、酞嗪、喹唑和喹喔琳及其单-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。
铂(II)络合物的具体实例示出如下，但不限于以下络合物:
Figure PCTCN2015074265-appb-000003
采用具有结构I的络合物，可制造热沉积和溶液处理的OLED。
包括含有一种或多种如权利要求1中所述的用于发光二极管的发光材料的有机发光器件。
其中通过热沉积在该器件中以层形式施加该用于发光二极管的发光材料。
其中通过旋涂在该器件中以层形式施加该用于发光二极管的发光材料。
其中通过喷墨印刷在该器件中以层形式施加该用于发光二极管的发光材料。
上述有机发光器件，其中在对层施加电流时该器件发射单色-红色。
本发明中的铂(II)络合物具有高发光量子效率,良好的热稳应性及低猝灭常数，可以制造高 效率并低效率衰减的红光OLED。
附图说明
图1:具有结构II的化学结构的配体的合成方案，
图2:具有结构I的化学结构的络合物的合成方案，
图3:络合物101的吸收及发射光谱，
图4:络合物101的循环伏安，
图5:用络合物101制备的OLED的数据，
图6:用络合物101制备的OLED的光谱。
具体实施方式
下面是如本文描述的铂(II)络合物(用于发光二极管的发光材料)的制备、物理性质和和电致发光数据的实例。提出实例是为了帮助理解本发明，而并非意欲且不应被解释为以任何方式对在其后所附权利要求书中阐述的本发明的限制。
除非在下面的实施例中和在说明书及权利要求书中其它地方另有指出，所有份数和百分比均以重量计，所有温度以摄氏度表示和压力为处于大气压或接近大气压。
不在操作实例中，或另有指出，提及用于本说明书及权利要求书中的成分、反应条件等的量的所有数字、值和/或表达应被理解为在所有情况下通过术语"约"来修饰。
至于给出特征的任何图或数字范围，自一个范围中的图或参数可与自对相同特征的不同范围的图或参数合并，以形成数字范围。
实施例201-具有结构II的化学结构的配体的通用制备方法：
参考图1，利用含有邻苯二胺基(结构III)的化学物与含有酚及双环的化学物(结构IV),通过缩合反应生成两个亚胺键后得到具有结构II的化学结构的配体。(上述III、IV是市售产品)
实施例202-配体301的制备
Figure PCTCN2015074265-appb-000004
通过实施例201中的方法制备配体301，其中R1-R26是氢。得率：100％。1H NMR(500MHz,CDCl3)δ13.33(s,2H),8.54(s,2H),7.34–7.22(m,2H),7.22–7.11(m,2H),7.09(s,2H),6.87(s,2H),3.32(d,J＝11.0Hz,4H),1.90(d,J＝7.5Hz,4H),1.73(d,J＝8.1Hz,2H),1.54(d,J＝8.6Hz, 2H),1.20(d,J＝5.7Hz,4H).
实施例203-具有结构I的化学结构的结构I的络合物的通用制备方法：
参考图2，首先把具有结构II(301)的化学结构的配体及两倍份量的弱碱溶在小量的热二甲基甲酰胺中，跟着把含有一倍份量带铂的盐的二甲基亚砜溶液加入其中。在反应一个晚上之后，用过滤法收集沉淀物，最后用重结晶法提纯。
实施例204-络合物101的制备
Figure PCTCN2015074265-appb-000005
通过实施例203中的方法制络合物101，其中弱碱是乙酸钠,带铂的盐是四氯铂酸钾，得率:32％.1H NMR(500MHz,CD2Cl2)δ8.76(s,2H),7.97(dd,J＝6.0,3.2Hz,2H),7.32(dd,J＝6.1,3.2Hz,2H),7.28(s,2H),7.08(s,2H),3.36(d,J＝6.4Hz,4H),1.97(d,J＝8.3Hz,4H),1.80(d,J＝8.0Hz,2H),1.62(d,J＝8.8Hz,2H),1.31(d,J＝7.5Hz,4H).
实施例205-络合物101的光物理性质
Figure PCTCN2015074265-appb-000006
实施例206-络合物101的电物理性质
Figure PCTCN2015074265-appb-000007
实施例207‐通用热离解OLED制造方法
在高真空环境(压力<1x10‐6托)中，在覆盖透明物质、空穴传输层、发光层、电子传输层、电子注入层的阳极和金属阴极上顺序沉积。
实施例208-用实施例207制造一种装置,其中的空穴传输层为40nm的4,4'-环己基二[N,N-二(4-甲基苯基)苯胺](TAPC)；发光由两层不同分层组成，第一层主要是三(4-咔唑-9基-苯基)胺(TcTa)(主体材料)的发光层，掺杂有小量络合物101(掺杂剂)，第二层是主要是9,9'-(2,6-吡啶二基二-3,1-亚苯)双-9H-咔唑(26DczPPy)(主体材料)的发光层，掺杂有小量络合物101(掺杂剂)；电子传输层为40nm的3,3'-[5'-[3-(3-吡啶基)苯基][1,1':3',1”-三联苯]-3,3”-二基]二吡啶(TmPYPB)；电子注入层为1nm的氟化锂和金属阴极为100nm的铝。
实施例209-实施例209阐明通过实施例208中所述的方法使用络合物101作为发光材料制成的OLED器件的器件性能.
Figure PCTCN2015074265-appb-000008
a)最大亮度；b)最大电流效率；c)最大电源效率；d)在1000cdm‐2的电流效率；e)效率衰减＝1‐(ηc 1000/ηc max)

Claims (10)

  1. 用于发光二极管的发光材料，其结构如式I所示，
    Figure PCTCN2015074265-appb-100001
    其中R1-R26独立地为氢、卤素、羟基、未取代烷基、取代烷基、环烷基、未取代芳基、取代芳基、酰基、烷氧基、酰氧基、氨基、硝基、酰基氨基、芳烷基、氰基、羧基、硫代、苯乙烯基、氨基羰基、氨基甲酰基、芳氧基羰基、苯氧基羰基或烷氧基羰基，R1-R26可独立地与邻近其它的R1-R26基团形成5-8元环。
  2. 根据权利要求1所述的发光材料，其中R1-R26独立地为氢、卤素、羟基、C1-C6烷基、五元或六元环烷基、五元或六元芳基、烷氧基、氨基、硝基、氰基、羧基、R1-R26可独立地与邻近其它的R1-R26基团形成5-6元环。
  3. 根据权利要求2所述的发光材料，其中R3-8、R17-22独立地为氢。
  4. 根据权利要求3所述的发光材料，其中R1、R11、R16、R24独立地为氢，R2、R23、R9-10、R25-26独立的为氢、C1-C6烷基。
  5. 根据权利要求4所述的发光材料，其中R12-15独立的为氢、卤素、羟基、C1-C6烷基、五元或六元环烷基、五元或六元芳基、氨基、硝基、氰基，或者R13、R14形成5-6元芳环。
  6. 根据权利要求5所述的发光材料，其中R13、R14独立的为氢、卤素、C1-C4烷基、氨基、硝基、氰基，或者R13、R14形成苯环。
  7. 根据权利要求6所述的发光材料，其中R12、R15独立的为氢、C1-C6烷基。
  8. 根据权利要求7所述的发光材料，为如下结构的化合物：
    Figure PCTCN2015074265-appb-100002
  9. 包括含有一种或多种如权利要求1-8任一所述的用于发光二极管的发光材料的有机发光器件。
  10. 根据权利要求9所述的有机发光器件，其中通过热沉积在该器件中以层形式施加该用于发光二极管的发光材料；或者通过旋涂在该器件中以层形式施加该用于发光二极管的发光材料；或者通过喷墨印刷在该器件中以层形式施加该用于发光二极管的发光材料。
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