WO2018137296A1 - 含有喹喔啉和联苯基团的化合物及其有机电致发光器件 - Google Patents

含有喹喔啉和联苯基团的化合物及其有机电致发光器件 Download PDF

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WO2018137296A1
WO2018137296A1 PCT/CN2017/082971 CN2017082971W WO2018137296A1 WO 2018137296 A1 WO2018137296 A1 WO 2018137296A1 CN 2017082971 W CN2017082971 W CN 2017082971W WO 2018137296 A1 WO2018137296 A1 WO 2018137296A1
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organic electroluminescent
organic
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黄锦海
苏建华
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上海道亦化工科技有限公司
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
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    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

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  • the invention relates to the field of organic electroluminescent materials, in particular to an organic electroluminescent compound containing quinoxaline and a biphenyl group and an organic electroluminescent device thereof, and belongs to the technical field of organic electroluminescent device display.
  • OLEDs are devices prepared by spin coating or vacuum evaporation of an organic material between two metal electrodes.
  • a classic three-layer organic electroluminescent device comprises a hole transport layer, Light emitting layer and electron transport layer. The holes generated by the anode pass through the hole transport layer and the electrons generated by the cathode are combined by the electron transport layer to form excitons in the light-emitting layer, and then emit light.
  • the organic electroluminescent device can adjust the emission of various desired light by changing the material of the light-emitting layer as needed.
  • organic electroluminescent devices have self-luminous, wide viewing angle, low power consumption, high efficiency, thin, rich color, fast response, wide temperature range, low driving voltage, flexible and bendable
  • the unique advantages of a transparent display panel and environmental friendliness can be applied to flat panel displays and next-generation lighting, or as a backlight for LCDs.
  • organic electroluminescent devices have been used in the industry, such as screens such as cameras and mobile phones, but current OLED devices are constrained by wider applications due to low efficiency and short service life. Especially for large screen displays, it is necessary to increase the efficiency of the device. An important factor limiting this is the performance of organic electroluminescent materials in organic electroluminescent devices.
  • the OLED device since the OLED device generates Joule heat when the voltage is applied, the organic material is easily crystallized, which affects the life and efficiency of the device. Therefore, it is also required to develop a stable and efficient organic electroluminescent material.
  • the present invention firstly provides an organic electroluminescent compound containing quinoxaline and a biphenyl group, which has A compound of the formula I below:
  • Ar 1 -Ar 4 are each independently selected from a C1-C8 alkyl group, a C1-C8 alkoxy group, a C6-C30 substituted or unsubstituted aryl group, a C3-C30 substituted or unsubstituted one or more a heteroatom aryl; L is biphenyl; X 1 and X 2 are each independently selected from N and CH.
  • Ar 1 -Ar 4 are each independently selected from the group consisting of phenyl, biphenyl, naphthyl, anthracenyl, dibenzofuranyl, dibenzothiophenyl, and the above groups may further be a C1-C10 alkane. Substituted by alkoxy groups.
  • the compound containing a quinoxaline and a biphenyl group of the present invention is a compound of the following structural formula 1-24:
  • organic electroluminescent compound containing quinoxaline and biphenyl group of the present invention can be applied to the field of organic electroluminescent devices, organic solar cells, organic thin film transistors or organic photoreceptors.
  • the present invention also provides an organic electroluminescent device comprising an anode, a cathode and an organic layer, the organic layer comprising a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, and an electron transport More than one layer of the layer, wherein at least one of the organic layers contains an organic electroluminescent compound containing a quinoxaline and a biphenyl group as described in Structural Formula I:
  • Ar 1 -Ar 4 , X 1 , X 2 and L are as defined above.
  • the organic layer is a light emitting layer and an electron transport layer
  • the organic layer is a light emitting layer, a hole injecting layer, a hole transporting layer, and an electron transporting layer;
  • the organic layer is a light emitting layer, a hole injecting layer, a hole transporting layer, an electron transporting layer, and an electron injecting layer;
  • the organic layer is a light emitting layer, a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, and a barrier layer;
  • the organic layer is a light emitting layer, a hole transport layer, an electron transport layer, an electron injection layer, and a barrier layer;
  • the organic layer is a light-emitting layer, a hole transport layer, an electron injection layer, and a barrier layer.
  • the layer containing the quinoxaline and biphenyl group-containing organic electroluminescent compound as described in Structural Formula I is an electron transport layer and/or an electron injection layer.
  • the organic electroluminescent compound containing quinoxaline and biphenyl group as described in Structural Formula I is a compound of Structural Formula 1-24.
  • the organic electroluminescent compound containing quinoxaline and biphenyl group as described in Structural Formula I can be used alone or in combination with other compounds for the preparation of a light-emitting device; the quinoxaline containing the formula I
  • the organic electroluminescent compound of the biphenyl group one of the compounds may be used alone, or two or more compounds of the formula I may be used at the same time.
  • the organic electroluminescent device comprises an anode, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode, wherein the electron transporting layer and/or the electron
  • the compound of the formula I is contained in the injection layer; further preferably, the compound of the formula 1-24 is contained in the electron transport layer and/or the electron injection layer.
  • the compound of the formula I can also serve as an electron injecting layer as an electron transporting layer.
  • the organic electroluminescent device of the present invention has a total thickness of the organic layer of from 1 to 1000 nm, preferably from 50 to 500 nm.
  • the organic electroluminescent device of the present invention can be used in combination with other materials such as a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a barrier layer when using the compound of the formula I of the present invention.
  • a hole injecting layer a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a barrier layer when using the compound of the formula I of the present invention.
  • a barrier layer when using the compound of the formula I of the present invention.
  • the hole transport layer and the hole injection layer of the organic electroluminescent device of the present invention have a good hole transporting property and can efficiently transport holes from the anode to the light emitting layer.
  • Other small molecules and high molecular organic compounds may be included, including but not limited to carbazole compounds, triarylamine compounds, biphenyldiamine compounds, terpenoids, phthalocyanines, hexanitrile hexazatriphenylene , 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), polyvinylcarbazole, polythiophene, polyethylene or polyphenylene Sulfonic acid.
  • the light-emitting layer of the organic electroluminescent device of the present invention has excellent light-emitting characteristics, and the range of visible light can be adjusted as needed. May contain the following compounds, including but not limited to naphthalenes, terpenoids, terpenoids, phenanthrene compounds, quinone compounds, fluoranthene compounds, terpenoids, pentacene compounds, terpenoids, diaryl Ethylene compound, triphenylamine ethylene compound, amine compound, carbazole compound, benzimidazole compound, furan compound, metal organic fluorescent complex, metal organic phosphorescent complex (such as Ir, Pt, Os, An organic polymer luminescent material such as Cu, Au), polyvinyl carbazole, polyorganosilicon compound or polythiophene may be used singly or in combination of plural kinds.
  • the organic electron transporting material of the organic electroluminescent device of the present invention is required to have good electron transporting property, and can efficiently transport electrons from the cathode to the light emitting layer, and has a large electron mobility.
  • the following compounds may be selected or formulated, but are not limited thereto: oxazolylazole, thiazole compound, triazole compound, triazine compound, triazabenzene compound , porphyrin compounds, diazonium compounds, silicon-containing heterocyclic compounds, quinoline compounds, phenanthroline compounds, metal chelates (such as Alq 3 , lithium quinolate), fluorine-substituted benzene a compound, a benzimidazole compound.
  • the electron injecting layer of the organic electroluminescent device of the present invention can effectively inject electrons from the cathode into the organic layer, except for the compound of the formula I of the present invention, which is mainly selected from the alkali metal or alkali metal compound, or is selected from the alkaline earth.
  • the following compounds may be selected, but are not limited thereto: an alkali metal, an alkaline earth metal, a rare earth metal, an oxide or halide of an alkali metal, an oxide or a halide of an alkaline earth metal, An oxide of a rare earth metal or an organic complex of a halide, an alkali metal or an alkaline earth metal; preferably lithium, lithium fluoride, lithium oxide, lithium nitride, lithium quinolate, hydrazine, cesium carbonate, 8-hydroxyl Quinolinium, calcium, calcium fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesium oxide, these compounds may be used singly or in combination with other organic electroluminescent materials.
  • Each layer of the organic layer in the organic electroluminescent device of the present invention may be subjected to vacuum evaporation, molecular beam evaporation, solvent dip coating, spin coating, bar coating or inkjet printing.
  • the metal motor can be prepared by an evaporation method or a sputtering method.
  • the device experiments show that the organic electroluminescent compound containing quinoxaline and biphenyl group according to the formula I has good thermal stability, high lifetime and high luminescence purity.
  • the organic electroluminescent device produced by using the organic electroluminescent compound has the advantages of good electroluminescence efficiency, excellent color purity, and long life.
  • FIG. 1 is a schematic structural view of an organic electroluminescent device of the present invention
  • 110 represents a glass substrate
  • 120 represents an anode
  • 130 represents a hole transport layer
  • 140 represents a light-emitting layer
  • 150 represents an electron transport layer
  • 160 represents an electron injection layer
  • 170 represents a cathode.
  • the synthesis method was the same as that of the intermediate 3-1, and the starting materials used were 3-chloro-phenylboronic acid and 4-(4-bromophenyl)-2,6-diphenylpyrimidine in a yield of 87%.
  • the synthesis method was the same as that of the intermediate 3-1, and the starting materials used were 3-chloro-benzeneboronic acid and 4-(3-bromophenyl)-2,6-diphenyl-1,3,5-triazine, yield 93 %.
  • the synthesis method was the same as that of the intermediate 3-1, and the starting materials used were 3-chlorophenylboronic acid and 2-phenyl-4-(4-biphenyl)-6-(3-bromophenyl)-pyrimidine in a yield of 86%. .
  • OLEDs are prepared using the compounds of the invention.
  • the transparent conductive ITO glass substrate 110 (with the anode 120 on the surface) (China CSG Group Co., Ltd.) was sequentially washed with deionized water, ethanol, acetone, and deionized water, and then treated with oxygen plasma for 30 seconds.
  • NPB was evaporated to form a hole transport layer 130 having a thickness of 60 nm.
  • a thickness of 37.5 nm is deposited on the light-emitting layer as the electron transport layer 150, including 75% of the present invention. And 25% LiQ.
  • LiF LiF was deposited as an electron injection layer 160 and 100 nm of Al as the device cathode 170.
  • Life after the devices prepared (see FIG. 1 structure diagram) operate at 6000cd / m 2 brightness of 24 hours as shown in Table 1.
  • the organic electroluminescent device prepared by applying the organic electroluminescent compound of the invention has a higher lifetime than the comparative example, and as described above, the compound of the invention has high stability, and the organic electricity prepared by the invention The electroluminescent device has a high lifetime and light purity.

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  • Optics & Photonics (AREA)
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Abstract

一种含有喹喔啉和联苯基团的有机电致发光化合物，该化合物具有较好热稳定性、高寿命、高发光纯度，可以用于制作有机电致发光器件，应用于有机太阳能电池、有机薄膜晶体管或有机光感受器领域。一种有机电致发光器件，其包括阳极（120）、阴极（170）和有机层，有机层包含发光层（140）、空穴注入层、空穴传输层（130）、空穴阻挡层、电子注入层（160）、电子传输层（150）中的一层以上，有机层中至少一层包含有如结构式I的化合物。

Description

含有喹喔啉和联苯基团的化合物及其有机电致发光器件 技术领域
本发明涉及有机电致发光材料领域，具体涉及一种含有喹喔啉和联苯基团的有机电致发光化合物及其有机电致发光器件，属于有机电致发光器件显示技术领域。
背景技术
有机电致发光器件(OLEDs)为在两个金属电极之间通过旋涂或者真空蒸镀沉积一层有机材料制备而成的器件，一个经典的三层有机电致发光器件包含空穴传输层、发光层和电子传输层。由阳极产生的空穴经空穴传输层跟由阴极产生的电子经电子传输层结合在发光层形成激子，而后发光。有机电致发光器件可以根据需要通过改变发光层的材料来调节发射各种需要的光。
有机电致发光器件作为一种新型的显示技术，具有自发光、宽视角、低能耗、效率高、薄、色彩丰富、响应速度快、适用温度范围广、低驱动电压、可制作柔性可弯曲与透明的显示面板以及环境友好等独特优点，可以应用在平板显示器和新一代照明上，也可以作为LCD的背光源。
自从20世纪80年代底发明以来，有机电致发光器件已经在产业上有所应用，比如作为相机和手机等屏幕，但是目前的OLED器件由于效率低，使用寿命短等因素制约其更广泛的应用，特别是大屏幕显示器，因此需要提高器件的效率。而制约其中的一个重要因素就是有机电致发光器件中的有机电致发光材料的性能。另外由于OLED器件在施加电压运行的时候，会产生焦耳热，使得有机材料容易发生结晶，影响了器件的寿命和效率，因此，也需要开发稳定高效的有机电致发光材料。
在OLED材料中，由于大多有机电致发光材料传输空穴的速度要比传输电子的速度快，容易造成发光层的电子和空穴数量不平衡，这样器件的效率就比较低。三(8-羟基喹啉)铝(Alq3)自发明以来，已经被广泛地研究，但是作为电子传输材料它的电子迁移率还是很低，并且自身会降解的内在特性，在以之为电子传输层的器件中，会出现电压下降的情况，同时，由于较低的电子迁移率，使得大量的空穴进入到Alq3层中，过量的空穴以非发光的形式辐射能量，并且在作为电子传输材料时，由于它发绿光的特性，在应用上受到了限制。因此，发展稳定并且具有较大电子迁移率的电子传输材料，对有机电致发光器件的广泛使用具有重大的价值。
发明内容
本发明首先提供一种含有喹喔啉和联苯基团的有机电致发光化合物，其为具有 如下结构式I的化合物：
Figure PCTCN2017082971-appb-000001
其中，Ar1-Ar4分别独立地选自C1-C8烷基、C1-C8烷氧基、C6-C30的取代或者未取代的芳基、C3-C30的取代或者未取代的含有一个或者多个的杂原子芳基；L为联苯；X1和X2分别独立地选自N和CH。
优选地，Ar1-Ar4分别独立地选自苯基、联苯基、萘基、芴基、二苯并呋喃基、二苯并噻吩基，以上这些基团可以进一步为C1-C10的烷基或者烷氧基取代。
进一步优选地，本发明的含有喹喔啉和联苯基团的化合物为下列结构式1-24的化合物：
Figure PCTCN2017082971-appb-000002
Figure PCTCN2017082971-appb-000003
Figure PCTCN2017082971-appb-000004
本发明的含有喹喔啉和联苯基团的有机电致发光化合物可以应用在有机电致发光器件、有机太阳能电池、有机薄膜晶体管或有机光感受器领域。
本发明还提供了一种有机电致发光器件，该器件包含阳极、阴极和有机层，有机层包含发光层、空穴注入层、空穴传输层、空穴阻挡层、电子注入层、电子传输层中的一层以上，其中所述有机层中至少有一层含有如结构式I所述的含有喹喔啉和联苯基团的有机电致发光化合物：
Figure PCTCN2017082971-appb-000005
其中Ar1-Ar4、X1、X2和L的定义如前所述。
其中有机层为发光层和电子传输层；
或者有机层为发光层、空穴注入层、空穴传输层和电子传输层；
或者有机层为发光层、空穴注入层、空穴传输层、电子传输层和电子注入层；
或者有机层为发光层、空穴注入层、空穴传输层、电子传输层、电子注入层和阻挡层；
或者有机层为发光层、空穴传输层、电子传输层、电子注入层和阻挡层；
或者有机层为发光层、空穴传输层、电子注入层和阻挡层。
优选地，如结构式I所述的含有喹喔啉和联苯基团的有机电致发光化合物所在层为电子传输层和/或电子注入层。
优选地，如结构式I所述的含有喹喔啉和联苯基团的有机电致发光化合物为结构式1-24的化合物。
如结构式I所述的含有喹喔啉和联苯基团的有机电致发光化合物用于发光器件制备时，可以单独使用，也可以和其它化合物混合使用；如结构式I所述的含有喹喔啉和联苯基团的有机电致发光化合物可以单独使用其中的一种化合物，也可以同时使用结构式I中的两种以上的化合物。
本发明的有机电致发光器件，进一步优选的方式为，该有机电致发光器件包含阳极、空穴传输层、发光层、电子传输层、电子注入层和阴极，其中电子传输层和/或电子注入层中含有结构式I的化合物；进一步优选地，电子传输层和/或电子注入层中含有结构式1-24的化合物。
在本发明的有机电致发光器件中，结构式I化合物作为电子传输层时也可以兼做电子注入层。
本发明的有机电致发光器件有机层的总厚度为1-1000nm，优选50-500nm。
本发明的有机电致发光器件在使用本发明具有结构式I的化合物时，可以搭配使用其它材料，如在空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阻挡层中等，而获得蓝光、绿光、黄光、红光或者白光。
本发明有机电致发光器件的空穴传输层和空穴注入层，所需材料具有很好的空穴传输性能，能够有效地把空穴从阳极传输到发光层上。可以包括其它小分子和高分子有机化合物，包括但不限于咔唑类化合物、三芳香胺化合物、联苯二胺化合物、芴类化合物、酞菁类化合物、六氰基六杂三苯(hexanitrilehexaazatriphenylene)、2,3,5,6-四氟-7,7',8,8'-四氰二甲基对苯醌(F4-TCNQ)、聚乙烯基咔唑、聚噻吩、聚乙烯或聚苯磺酸。
本发明的有机电致发光器件的发光层，具有很好的发光特性，可以根据需要调节可见光的范围。可以含有如下化合物，包括但是不限于萘类化合物、芘类化合物、芴类化合物、菲类化合物、屈类化合物、荧蒽类化合物、蒽类化合物、并五苯类化合物、苝类化合物、二芳乙烯类化合物、三苯胺乙烯类化合物、胺类化合物、咔唑类化合物、苯并咪唑类化合物、呋喃类化合物、金属有机荧光络合物、金属有机磷光络合物(如Ir、Pt、Os、Cu、Au)、聚乙烯咔唑、聚有机硅化合物、聚噻吩等有机高分子发光材料，它们可以单独使用，也可以多种混合物使用。
本发明有机电致发光器件的有机电子传输材料要求具有很好的电子传输性能，能够有效地把电子从阴极传输到发光层中，具有很大的电子迁移率。除本发明的具有结构式I化合物外，还可以选择或者搭配如下化合物，但是不限于此：氧杂恶唑、噻唑类化合物、三氮唑类化合物、三氮嗪类化合物、三氮杂苯类化合物、喔啉类化合物、二氮蒽类化合物、含硅杂环类化合物、喹啉类化合物、菲啰啉类化合物、金属螯合物(如Alq3、8-羟基喹啉锂)、氟取代苯类化合物、苯并咪唑类化合物。
本发明有机电致发光器件的电子注入层，可以有效地把电子从阴极注入到有机层中，除本发明的具有结构式I化合物外，主要选自碱金属或者碱金属的化合物，或选自碱土金属或者碱土金属的化合物或者碱金属络合物，可以选择如下化合物，但是不限于此：碱金属、碱土金属、稀土金属、碱金属的氧化物或者卤化物、碱土金属的氧化物或者卤化物、稀土金属的氧化物或者卤化物、碱金属或者碱土金属的有机络合物；优选为锂、氟化锂、氧化锂、氮化锂、8-羟基喹啉锂、铯、碳酸铯、8-羟基喹啉铯、钙、氟化钙、氧化钙、镁、氟化镁、碳酸镁、氧化镁，这些化合物可以单独使用也可以混合物使用，也可以跟其他有机电致发光材料配合使用。
本发明的有机电致发光器件中有机层的每一层，可以通过真空蒸镀法、分子束蒸镀法、溶于溶剂的浸涂法、旋涂法、棒涂法或者喷墨打印等方式制备。对于金属电机可以使用蒸镀法或者溅射法进行制备。
器件实验表明，本发明如结构式I所述的含有喹喔啉和联苯基团的有机电致发光化合物，具有较好热稳定性、高寿命、高发光纯度。采用该有机电致发光化合物制作的有机电致发光器件具有电致发光效率良好和色纯度优异以及寿命长的优点。
附图说明
图1是本发明的一种有机电致发光器件结构示意图；
其中，110代表为玻璃基板，120代表为阳极，130代表为空穴传输层，140代表为发光层，150代表为电子传输层，160代表为电子注入层，170代表为阴极。
具体实施方式
为了更详细叙述本发明，特举以下例子，但是不限于此。
实施例1
化合物3的合成
Figure PCTCN2017082971-appb-000006
中间体3-1的合成
在三口烧瓶中，加入对氯苯硼酸(2g,12.8mmol)、2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪(5g,12.8mmol)、碳酸钾(3.5g,25.6mmol)、四三苯基膦钯(0.2g)、四氢呋喃(50ml)和水(15ml)，在氮气保护下加热回流10小时，冷却，浓缩，过滤，粗产品用四氢呋喃和乙醇重结晶得到产率4.9g，产率91％。
化合物3的合成
在三口烧瓶中，加入中间体3-1(3g,7.2mmol)、2,3-二苯基-6-(4,4,5,5-四甲基-1,3,2-二氧基-硼基)-喹喔啉(2.9g,7.2mmol)、碳酸钾(2g,15mmol)、醋酸钯(0.2g)、X-phos(0.4g)、四氢呋喃(50ml)和水(15ml)，在氮气保护下加热回流10小时，冷却，浓缩，过滤，粗产品用四氢呋喃和乙醇重结晶得到产率3.9g，产率82％。质谱665.51。
实施例2
化合物5的合成
Figure PCTCN2017082971-appb-000007
中间体5-1
合成方法跟中间体3-1一样，所用原料为3-氯-苯硼酸和4-(4-溴苯基)-2,6-二苯基嘧啶，产率87％。
化合物5的合成
合成方法跟化合物3一样，用中间体5-1代替中间体3-1，产率71％。质谱664.71。
实施例3
化合物12的合成
Figure PCTCN2017082971-appb-000008
中间体12-1的合成
合成方法跟中间体3-1一样，所用原料为3-氯-苯硼酸和4-(3-溴苯基)-2,6-二苯基-1,3,5-三嗪，产率93％。
化合物12的合成
合成方法跟化合物3一样，除了用中间体12-1代替中间体3-1外，产率75％。质谱665.49。
实施例4
化合物23的合成
Figure PCTCN2017082971-appb-000009
中间体23-1的合成
合成方法跟中间体3-1一样，所用原料为3-氯苯硼酸和2-苯基-4-(4-联苯基)-6-(3-溴苯基)-嘧啶，产率86％。
化合物23的合成
合成方法跟化合物3的合成一样，除了有用中间体23-1代替3-1外，产率87％。质谱740.31。
实施例5-8
有机电致发光器件的制备
使用本发明的化合物制备OLED。
首先，将透明导电ITO玻璃基板110(上面带有阳极120)(中国南玻集团股份有限公司)依次经：去离子水、乙醇、丙酮和去离子水洗净，再用氧等离子处理30秒。
然后，蒸镀NPB，形成60nm厚的空穴传输层130。
然后，在空穴传输层上蒸镀37.5nm厚的Alq3掺杂1％C-545T作为发光层140。
然后，在发光层上蒸镀37.5nm厚作为电子传输层150，包含75％本发明化合 物和25％的LiQ。
最后，蒸镀1nm LiF为电子注入层160和100nm Al作为器件阴极170。
比较例
除了电子传输层用Alq3代替本发明化合物外，其它的跟实施例5-8一样。
所制备的器件(结构示意图见图1)在6000cd/m2亮度下工作24小时后的寿命如表1所示。
表1
实施例 化合物 寿命 颜色
5 3 82％ 绿光
6 5 83％ 绿光
7 12 84％ 绿光
8 23 84％ 绿光
比较例 Alq3 75％ 绿光
在相同的条件下，应用本发明的有机电致发光化合物制备的有机电致发光器件的寿命都高于比较例，如上所述，本发明的化合物具有高的稳定性，本发明制备的有机电致发光器件具有高的寿命和光纯度。
器件中所述化合物的结构式如下：
Figure PCTCN2017082971-appb-000010
以上详细描述了本发明的较佳具体实施例。应当理解，本领域的普通技术人员无需创造性劳动就可以根据本发明的构思作出诸多修改和变化。因此，凡本技术领域中技术人员依本发明的构思在现有技术的基础上通过逻辑分析、推理或者有限的实验可以得到的技术方案，皆应在由权利要求书所确定的保护范围内。

Claims (9)

  1. 一种含有喹喔啉和联苯基团的有机电致发光化合物，其特征在于其为具有如下结构式I的化合物：
    Figure PCTCN2017082971-appb-100001
    其中，Ar1-Ar4分别独立地选自C1-C8烷基、C1-C8烷氧基、C6-C30的取代或者未取代的芳基、C3-C30的取代或者未取代的含有一个或者多个的杂原子芳基；L为联苯；X1和X2分别独立地选自N和CH。
  2. 根据权利要求1所述的含有喹喔啉和联苯基团的有机电致发光化合物，其特征在于Ar1-Ar4分别独立地选自苯基、联苯基、萘基、芴基、二苯并呋喃基、二苯并噻吩基，或以上这些基团进一步为C1-C10的烷基或者烷氧基取代。
  3. 根据权利要求1所述的含有喹喔啉和联苯基团的有机电致发光化合物，其特征在于其为下列结构式1-24的化合物：
    Figure PCTCN2017082971-appb-100002
    Figure PCTCN2017082971-appb-100003
    Figure PCTCN2017082971-appb-100004
  4. 一种有机电致发光器件，其包括阳极、阴极和有机层，有机层包含发光层、空穴注入层、空穴传输层、空穴阻挡层、电子注入层、电子传输层中的一层以上，其特征在于所述有机层中至少有一层含有如权利要求1所述的含有喹喔啉和联苯基团的有机电致发光化合物。
  5. 根据权利要求4所述的有机电致发光器件，其特征在于如结构式I所述的含有喹喔啉和联苯基团的有机电致发光化合物所在层为电子传输层和/或电子注入层。
  6. 根据权利要求4所述的有机电致发光器件，其特征在于如结构式I所述的含有喹喔啉和联苯基团的有机电致发光化合物为结构式1-24的化合物。
  7. 根据权利要求4所述的有机电致发光器件，其特征在于如结构式I所述的含有喹喔啉和联苯基团的有机电致发光化合物单独使用，或和其它化合物混合使用。
  8. 根据权利要求4所述的有机电致发光器件，其特征在于如结构式I所述的含有喹喔啉和联苯基团的有机电致发光化合物单独使用其中的一种化合物，或同时使用结构式I中的两种以上的化合物。
  9. 根据权利要求4所述的有机电致发光器件，其特征在于其包含阳极、空穴传输层、发光层、电子传输层、电子注入层和阴极，其特征在于电子传输层和/或电子注入层中含有结构式I的化合物。
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