WO2021103728A1 - Organic compound and organic electroluminescent device using same - Google Patents

Organic compound and organic electroluminescent device using same Download PDF

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WO2021103728A1
WO2021103728A1 PCT/CN2020/112988 CN2020112988W WO2021103728A1 WO 2021103728 A1 WO2021103728 A1 WO 2021103728A1 CN 2020112988 W CN2020112988 W CN 2020112988W WO 2021103728 A1 WO2021103728 A1 WO 2021103728A1
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organic
compound
layer
light
organic compound
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PCT/CN2020/112988
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Chinese (zh)
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赵晓宇
汪华月
华万鸣
黄娣
钱烨
杨金萍
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浙江华显光电科技有限公司
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Definitions

  • the present invention relates to an organic compound in the field of organic electroluminescence and an organic electroluminescence device using the compound, in particular a triphenylamine derivative and an organic electroluminescence device using the compound.
  • OLED Organic Light Emission Diodes
  • OLED devices usually have a sandwich-like structure, including positive and negative electrode film layers and organic functional material layers sandwiched between the electrode film layers. A voltage is applied to the electrodes of the OLED device, positive charges are injected from the positive electrode, and negative charges are injected from the negative electrode. Under the action of an electric field, the positive and negative charges migrate in the organic layer and meet and combine to emit light. It has been widely used in the display panels of new lighting fixtures, smart phones and tablet computers, and will further expand to the application of large-size display products such as TVs. It is a new display technology with fast development and high technical requirements.
  • OLED devices usually include the following types of organic materials: hole injection materials, hole transport materials, electron transport materials, as well as light-emitting materials of various colors (dye or doped guest materials) and corresponding host materials.
  • a host-guest structure that is, a phosphorescent emitting material is doped into the host material at a certain concentration to avoid triplet-triplet annihilation and improve phosphorescence emission efficiency.
  • the existing blue light host materials are anthracene-based fused ring derivatives, as described in patents CN1914293B, CN102448945B, US2015287928A1, etc. However, these compounds have problems of insufficient luminous efficiency and brightness, and poor device life.
  • aryl vinyl amine compounds WO 04/013073, WO 04/016575, WO 04/018587
  • hole-transporting host materials are most commonly used.
  • the molecules of these materials contain electron donors, such as carbazole and triphenylamine structures, which have the characteristics of hole transport.
  • Triphenylamine has a very high triplet energy level, ET is 3.04eV
  • the hole transport materials TAPC, TcTa, TPD, etc. that are often used are all derivatives of triphenylamine.
  • the HOMO energy level of most derivatives of triphenylamine is higher than that of carbazole derivatives, about -5.3eV, and its work function is close to that of ITO.
  • HOMO is also close to hole transport material NPB, which is conducive to holes. Implanted, so they are suitable for electro-phosphorescent host materials.
  • triphenylamine derivatives as phosphorescent host materials.
  • Yang's project was combined into a bridged structure of triphenylamine derivative FATPA, ["A fully diarylmethylene-bridged triphenylamine derivative as novel host for highly efficient green phosphorescent OLEDs", Org. Lett. 2009, 11. ,1503.] It is connected to the methylene group of diphenylmethane through the ortho position of aniline.
  • blue phosphorescent materials are the latest and the least mature. This is mainly due to the short wavelength and high energy level of blue phosphorescence.
  • it is necessary to increase the energy gap of the ligand that is, increase the energy levels of the HOMO and LUMO of the ligand by modifying the chemical structure of the ligand. This will lead to the weakening of the coordination bond between the ligand and the metal.
  • the stability of the complex is reduced, the complex is prone to bond breakage, and the non-radiative attenuation of the complex to the ground state will be accelerated. Phosphorescence efficiency is reduced.
  • blue phosphorescent materials the blue shift of wavelength and high-efficiency luminescence are a contradiction, and it is a dilemma to choose both at the same time. At the same time, this is also the reason why phosphorescent doped materials that play a role in emitting light are often used with host materials.
  • the triplet energy level of blue phosphorescent materials is relatively high, so a host with a higher triplet energy level is often required. The material is matched with it, so as to ensure that energy is transferred to the guest blue phosphorescent material to release phosphorescence.
  • the triplet energy level of the host material is lower than the triplet energy level of the blue phosphorescent material, the energy will be transferred to the host material and released, and the host material is a pure organic compound, and phosphorescence is not visible at room temperature, so The luminous efficiency of the device will decrease.
  • the existing blue light materials have poor thermal stability and are easy to decompose, resulting in poor device life; poor color purity makes it difficult to achieve deep blue light emission, so there are problems in full-color displays that reflect natural colors. Therefore, the materials still need to be further improved. High-performance blue light materials have always been the focus of people's development.
  • the asymmetric structural characteristics of the compound of the present invention improve device efficiency, thermal stability, film formation and other properties, and the patent is relatively simple in synthesis route.
  • the organic compound of the present invention is applied to the light-emitting layer in OLED devices and used as a blue light material.
  • the compound of the present invention triphenylamine and fluorene are linked to triphenylamine derivatives, because the C atom on the spiro ring blocks triphenylamine from other benzenes.
  • the conjugation of the ring allows the triplet state of the molecule to be maintained, with a higher triplet energy level, and more sufficient energy transfer; the transfer of electrons and holes is more balanced, and the efficiency and lifetime of the device are higher.
  • the invention provides an organic compound and its synthesis Method and its application in the field of organic electroluminescence.
  • the molecular structure of the organic compound is shown in structural formula I:
  • Ar 1 to Ar 4 are independently selected from substituted or unsubstituted C6-C60 aryl or heteroaryl, wherein the heteroaryl contains selected from B, N, O, S, Si and P At least one heteroatom, and preferably at least one N;
  • an organic compound of the present invention is independently selected from the following compounds:
  • the present invention also provides an organic electroluminescent device.
  • the device includes a cathode layer, an anode layer, and an organic layer.
  • the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, and an electron injection layer. And at least one of the electron transport layers, wherein at least one of the organic layers contains the compound represented by structural formula I.
  • the phosphorescent organic compound represented by structural formula I is as described above.
  • an organic compound represented by structural formula I is used as an organic material for the light-emitting layer of an organic electroluminescence device.
  • an organic compound represented by structural formula I is used as a guest dopant for the light-emitting layer of the organic electroluminescence device.
  • the compound represented by structural formula I can be used alone in organic electroluminescent devices, or used in combination with other compounds; the compound represented by structural formula I can use one of these compounds, or both Two or more compounds; use one compound selected from the structure formula I alone, or use two or more compounds selected from the structure formula I at the same time.
  • the light-emitting layer may be a red, yellow or blue light-emitting layer.
  • the above-mentioned compound for organic electro-devices is used as the blue host or blue doping, which can obtain high efficiency, high resolution, high brightness and long length. Life-span organic electro-induced devices.
  • the organic layer preferably includes an electron transport layer, and the electron transport layer includes the compound for an organic electro-device according to the above technical solution.
  • the electron transport layer preferably further includes a metal compound.
  • the organic layer preferably includes a light-emitting layer and an electron-transporting layer, and both the light-emitting layer and the electron-transporting layer contain the compound for an organic electro-device according to the above technical solution, and the light-emitting layer and the electron-transporting layer
  • the organic compounds can be the same or different.
  • the present invention has no special restrictions on the preparation method of the organic electro-device.
  • the preparation method and material of the light-emitting device well known to those skilled in the art are used. can.
  • the organic electro-induced device of the present invention is an organic photovoltaic device, an organic light-emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-paper), an organic photoreceptor (OPC), an organic thin film transistor (OTFT) and Any of organic memory devices (Organic Memory Element).
  • OLED organic light-emitting device
  • OSC organic solar cell
  • e-paper electronic paper
  • OPC organic photoreceptor
  • OFT organic thin film transistor
  • Any of organic memory devices Organic Memory Element
  • the organic electro-optical device can use sputter coating, electron beam evaporation, vacuum evaporation and other methods to evaporate metal or conductive oxides and their alloys on the substrate to form an anode;
  • the surface of the anode is prepared by evaporating a hole injection layer, a hole transport layer, a light-emitting layer, an air barrier layer and an electron transport layer in order, and then the cathode is evaporated.
  • organic electro-devices are produced by vapor deposition on the substrate in the order of cathode, organic layer, and anode.
  • the organic layer may also include a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, and an electron transport layer.
  • the organic layer is made of polymer materials according to solvent engineering (spin-coating, tape-casting, doctor-blading, and Screen-Printing). , Inkjet printing or thermal imaging (Thermal-Imaging), etc.) instead of vapor deposition method, can reduce the number of device layers.
  • the materials used in the organic electro-optical device according to the present invention can be classified into top emission, low emission or double-sided emission.
  • the compound of the organic electro-optical device according to the embodiment of the present invention can be applied to organic solar cells, lighting OLEDs, flexible OLEDs, organic photoreceptors, organic thin-film transistors and other electro-induced devices on a similar principle to organic light-emitting devices.
  • the novel phosphorescent organic compound of the present invention has a relatively large molecular weight, multiple conjugated plane groups connected by single bonds, poor spatial symmetry, difficult to crystallize and decompose, increase the glass transition temperature of the material, and ensure that the material is not vaporized for a long time.
  • Decomposition The organic compound of the present invention is applied to electroluminescent devices, and has a large triplet energy level T1 that can block exciton diffusion and improve the efficiency and life of the device; the organic phosphorescence of the present invention is an organic compound that can balance holes And the transfer of electrons, improve the life of the device.
  • Figure 1 is a structural layer diagram of an organic electroluminescent diode device of the present invention
  • 110 represents a substrate
  • 120 represents an anode
  • 130 represents a hole injection layer
  • 140 represents a hole transport layer
  • 150 represents a light-emitting layer
  • 160 represents a hole blocking layer
  • 170 represents an electron transport layer
  • 180 represents an electron injection layer
  • 190 represents cathode.
  • intermediate 1-b (14.1 g, 39.6 mmol) and 145 mL of methanesulfonic acid were added, and the mixture was heated to 80° C. to react for 3 hours. It was confirmed by thin layer chromatography that the reaction was completed and then cooled to room temperature. The reaction solution was slowly added dropwise to 150 mL of ice water and then stirred for 30 minutes. The resulting solid was filtered and washed with water and methanol to obtain Intermediate 1-c (11.1 g, yield, 83%).
  • the present invention also prepares 10 bottom light emitting devices by means of thermal evaporation (each specific device structure is as follows:
  • the coating thickness of Fisher Company is The ITO glass substrate is cleaned twice in distilled water, ultrasonically cleaned for 30 minutes, and then repeatedly cleaned with distilled water for two times, ultrasonically cleaned for 10 minutes, after the distilled water cleaning is completed, use isopropanol, acetone, methanol solvents to perform ultrasonic cleaning in order After drying, the dried substrate is transferred to a plasma cleaning machine, and the substrate is washed for 5 minutes and then sent to the vapor deposition machine.
  • the hole injection layer 2-TNATA vapor deposition thickness is sequentially evaporated
  • the hole transport layer a-NPD evaporation thickness is ADN (9,10-bis(2-naphthyl)anthracene) and 5% of BD1 ⁇ BD3 or an organic compound of the present invention.
  • the vapor deposition thickness is The hole blocking layer and electron transport layer TPBi evaporation thickness is The thickness of LiF evaporation is And Al evaporation thickness is The cathode is formed; the organic vapor deposition speed is maintained during the above process
  • the evaporation rate of LiF is The vapor deposition rate of Al is
  • Table 1 shows the performance test results of the organic light-emitting devices prepared in the embodiment of the present invention and the comparative example.

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Abstract

An organic compound and an organic electroluminescent device using the compound used for the field of organic electroluminescence. The organic compound is as shown in structural formula I, wherein Ar1 to Ar 4 are independently selected from substituted or unsubstituted C6-C60 aryl or heteroaryl group and the heteroaryl group contains at least one heteroatom selected from B, N, O, S, Si and P, and preferably at least one N; and X is independently selected from O, S, Se, C(R)2, Si(R)2, NR, P(＝O)R or carbonyl, and R is selected from H, CN, alkyl and aryl. The compound has good thermal stability and high triplet energy level, can balance the transfer of holes and electrons, can implement sufficient energy transfer, and can effectively improve the efficiency and lifetime of the device.

Description

一种有机化合物和使用该化合物的有机电致发光器件Organic compound and organic electroluminescence device using the compound 技术领域Technical field
本发明涉及有机电致发光领域的一种有机化合物和使用该化合物的有机电致发光器件，具体为三苯胺衍生物和使用该化合物的有机电致发光器件。The present invention relates to an organic compound in the field of organic electroluminescence and an organic electroluminescence device using the compound, in particular a triphenylamine derivative and an organic electroluminescence device using the compound.
背景技术Background technique
有机电致发光器件(OLED:Organic Light Emission Diodes)有视角广阔、响应速度快、色彩质量高、可实现柔性发光等优点，具有广阔的应用前景。OLED器件通常是类三明治结构，包括正负电极膜层及夹在电极膜层之间的有机功能材料层。对OLED器件的电极施加电压，正电荷从正极注入，负电荷从负极注入，在电场作用下正负电荷在有机层中迁移相遇复合发光。已被广泛应用于新型照明灯具、智能手机及平板电脑等产品的显示面板，进一步还将向电视等大尺寸显示产品应用领域扩展，是一种发展快、技术要求高的新型显示技术。Organic Light Emission Diodes (OLED: Organic Light Emission Diodes) have the advantages of wide viewing angle, fast response speed, high color quality, flexible light emission, etc., and have broad application prospects. OLED devices usually have a sandwich-like structure, including positive and negative electrode film layers and organic functional material layers sandwiched between the electrode film layers. A voltage is applied to the electrodes of the OLED device, positive charges are injected from the positive electrode, and negative charges are injected from the negative electrode. Under the action of an electric field, the positive and negative charges migrate in the organic layer and meet and combine to emit light. It has been widely used in the display panels of new lighting fixtures, smart phones and tablet computers, and will further expand to the application of large-size display products such as TVs. It is a new display technology with fast development and high technical requirements.
一个效率好寿命长的有机电致发光器件通常是器件结构与各种有机材料的优化搭配的结果。常见的OLED器件通常包括以下种类的有机材料：空穴注入材料、空穴传输材料、电子传输材料，以及各色的发光材料(染料或者掺杂客体材料)和相应的主体材料等。An organic electroluminescent device with good efficiency and long lifetime is usually the result of the optimized combination of device structure and various organic materials. Common OLED devices usually include the following types of organic materials: hole injection materials, hole transport materials, electron transport materials, as well as light-emitting materials of various colors (dye or doped guest materials) and corresponding host materials.
现在的磷光电致发光器件中大多采用主客体结构，即将磷光发射物质以一定的浓度掺杂在主体物质中，以避免三重态-三重态湮灭，提高磷光发射效率。作为现有的蓝光主体材料是基于蒽的稠环类衍生物，如专利CN1914293B、CN102448945B、US2015287928A1等所述，然而这些化合物存在发光效率和亮度不充分及器件寿命较差的问题。作为现有技术的发蓝光客体化合物，可采用的是芳基乙烯基胺类化合物(WO 04/013073，WO 04/016575，WO 04/018587)。然而，这些化合物的热稳定性差，易分解，导致器件的寿命差，是目前产业上OLED材料最主要的缺点。此外，这些化合物的色纯度差，难以实现深蓝色的发光。另外，US 7233019、KR 2006-0006760等专利公开了利用芳基胺取代基的芘系化合物的有机电致发光元件，但是因为蓝光的色纯度低，很难实现深蓝发光。Most of the current phosphorescent electroluminescent devices adopt a host-guest structure, that is, a phosphorescent emitting material is doped into the host material at a certain concentration to avoid triplet-triplet annihilation and improve phosphorescence emission efficiency. The existing blue light host materials are anthracene-based fused ring derivatives, as described in patents CN1914293B, CN102448945B, US2015287928A1, etc. However, these compounds have problems of insufficient luminous efficiency and brightness, and poor device life. As the blue light-emitting guest compound in the prior art, aryl vinyl amine compounds (WO 04/013073, WO 04/016575, WO 04/018587) can be used. However, these compounds have poor thermal stability and are easy to decompose, leading to poor device life, which is the main disadvantage of OLED materials in the industry. In addition, these compounds have poor color purity, and it is difficult to achieve deep blue light emission. In addition, US 7233019, KR 2006-0006760 and other patents disclose organic electroluminescence elements using pyrene-based compounds with arylamine substituents, but because of the low color purity of blue light, it is difficult to achieve deep blue light emission.
在磷光主体材料中，最常使用的是空穴传输型主体材料。这类材料的分子中含有电子给体，如咔唑和三苯胺结构，具有空穴传输的特点。三苯胺具有很高的三线态能级，ET为3.04eV，经常使用空的穴传输材料TAPC、TcTa、TPD等都是三苯胺的衍生物。大多数三苯胺的衍生物的HOMO能级要比咔唑衍生物高，大概为-5.3eV，而且它与ITO的功函数接近，HOMO也与空穴传输材料NPB接近，有利于空穴的注入，因此它们适合于做电致磷光主体材料。但是由于三苯胺分子结构是扭曲的，缺少刚性，使得三苯胺衍生物的热稳定性和形貌稳定性不够好，这影响了它们的实际应用。所以关于三苯胺衍生物作为磷光主体材料的报道不是很多。为了提高三苯胺的刚性结构，Yang课题组合成了桥联结构的三苯胺衍生物FATPA，[“A fully diarylmethylene-bridged triphenylamine derivative as novel host for highly efficient green phosphorescent OLEDs”,Org.Lett.2009,11,1503.]它是通过苯胺的邻位与二苯甲烷的亚甲基连接，三苯胺形成了接近平面的环状结构，这样的结构使得分子具有较高的玻璃转化温度，Tg为178℃。该分子同时保持了较高的三线态能级(ET＝2.78eV)和HOMO(-5.22eV)能级。Among phosphorescent host materials, hole-transporting host materials are most commonly used. The molecules of these materials contain electron donors, such as carbazole and triphenylamine structures, which have the characteristics of hole transport. Triphenylamine has a very high triplet energy level, ET is 3.04eV, and the hole transport materials TAPC, TcTa, TPD, etc. that are often used are all derivatives of triphenylamine. The HOMO energy level of most derivatives of triphenylamine is higher than that of carbazole derivatives, about -5.3eV, and its work function is close to that of ITO. HOMO is also close to hole transport material NPB, which is conducive to holes. Implanted, so they are suitable for electro-phosphorescent host materials. However, because the molecular structure of triphenylamine is distorted and lacks rigidity, the thermal stability and morphological stability of triphenylamine derivatives are not good enough, which affects their practical applications. Therefore, there are not many reports about triphenylamine derivatives as phosphorescent host materials. In order to improve the rigid structure of triphenylamine, Yang's project was combined into a bridged structure of triphenylamine derivative FATPA, ["A fully diarylmethylene-bridged triphenylamine derivative as novel host for highly efficient green phosphorescent OLEDs", Org. Lett. 2009, 11. ,1503.] It is connected to the methylene group of diphenylmethane through the ortho position of aniline. Triphenylamine forms a nearly planar cyclic structure. This structure makes the molecule have a higher glass transition temperature, with a Tg of 178°C. The molecule maintains a higher triplet energy level (ET=2.78eV) and HOMO (-5.22eV) energy level at the same time.
相对于红色磷光材料和绿色磷光材料，蓝色磷光材料是开发得最晚的，也是最不成熟的。这主要是由蓝色磷光波长短能级高，为了获得短波长发光，就必须拉大配体的能隙，即通过修配体的化学结构来拉大配体的HOMO和LUMO的能级，但是，这样又会导致配体和金属之间的配位键的减弱，一方面使得配合物的稳定性降低，配合物容易发生键断裂，而且会加速配合物以非辐射方式衰减会到基态，使磷光效率降低。因此，在蓝色磷光材料中，波长的蓝移和高效发光是一对矛盾，同时兼有两者是两难的选择。同时这也是器件的结构中起发光作用的磷光掺杂材料往往要搭配的主体材料使用的原因，但蓝色磷光材料的三线态能级比较高，所以常常需要比其三线态能级高的主体材料与之相匹配，这样才能保证将能量传递给客体蓝色磷光材料，释放出磷光。如果主体材料的三线态能级低于蓝色磷光材料的三线态能级，则能量会传递到主体材料上释放，而主体材料是纯的有机化合物，在室温下是看不到磷光的，所以器件的发光效率会降低。同时现有的蓝光材料存在热稳定性差，易分解，导致器件的寿命差；色纯度差，难以实现深蓝色的发光，因此在体现 天然颜色的全彩色显示器方面有问题。因此，仍需进一步改进材料。高性能的蓝光材料一直是人们的开发重点。Compared with red phosphorescent materials and green phosphorescent materials, blue phosphorescent materials are the latest and the least mature. This is mainly due to the short wavelength and high energy level of blue phosphorescence. In order to obtain short-wavelength light emission, it is necessary to increase the energy gap of the ligand, that is, increase the energy levels of the HOMO and LUMO of the ligand by modifying the chemical structure of the ligand. This will lead to the weakening of the coordination bond between the ligand and the metal. On the one hand, the stability of the complex is reduced, the complex is prone to bond breakage, and the non-radiative attenuation of the complex to the ground state will be accelerated. Phosphorescence efficiency is reduced. Therefore, in blue phosphorescent materials, the blue shift of wavelength and high-efficiency luminescence are a contradiction, and it is a dilemma to choose both at the same time. At the same time, this is also the reason why phosphorescent doped materials that play a role in emitting light are often used with host materials. However, the triplet energy level of blue phosphorescent materials is relatively high, so a host with a higher triplet energy level is often required. The material is matched with it, so as to ensure that energy is transferred to the guest blue phosphorescent material to release phosphorescence. If the triplet energy level of the host material is lower than the triplet energy level of the blue phosphorescent material, the energy will be transferred to the host material and released, and the host material is a pure organic compound, and phosphorescence is not visible at room temperature, so The luminous efficiency of the device will decrease. At the same time, the existing blue light materials have poor thermal stability and are easy to decompose, resulting in poor device life; poor color purity makes it difficult to achieve deep blue light emission, so there are problems in full-color displays that reflect natural colors. Therefore, the materials still need to be further improved. High-performance blue light materials have always been the focus of people's development.
本发明化合物不对称的结构特性提高器件效率，热稳定性、成膜等性能，本专利比较相对合成路线简单。本发明的有机化合物应用于OLED器件中的发光层，并当作蓝光材料使用，本发明化合物三苯胺与芴连接起来三苯胺衍生物，由于螺环上的C原子阻断了三苯胺与其它苯环的共轭，使得分子的三线态得到了维持，具有较高的三线态能级，能量传递更加充分；电子和空穴的传递更加平衡，器件的效率和寿命更高。The asymmetric structural characteristics of the compound of the present invention improve device efficiency, thermal stability, film formation and other properties, and the patent is relatively simple in synthesis route. The organic compound of the present invention is applied to the light-emitting layer in OLED devices and used as a blue light material. The compound of the present invention, triphenylamine and fluorene are linked to triphenylamine derivatives, because the C atom on the spiro ring blocks triphenylamine from other benzenes. The conjugation of the ring allows the triplet state of the molecule to be maintained, with a higher triplet energy level, and more sufficient energy transfer; the transfer of electrons and holes is more balanced, and the efficiency and lifetime of the device are higher.
发明内容Summary of the invention
本发明为解决常用蓝色磷光材料的玻璃化温度较低，材料本身稳定性不高，且在高亮度下具有高效率滚降，阻碍其广泛使用的问题，而提供一种有机化合物、其合成方法及其在有机电致发光领域的应用。该有机化合物的分子结构如结构式I所示：In order to solve the problems that commonly used blue phosphorescent materials have low glass transition temperature, low stability of the material itself, and high-efficiency roll-off under high brightness, which hinders its widespread use, the invention provides an organic compound and its synthesis Method and its application in the field of organic electroluminescence. The molecular structure of the organic compound is shown in structural formula I:
Figure PCTCN2020112988-appb-000001
Figure PCTCN2020112988-appb-000001
其中，结构式I中，Ar 1至Ar 4独立地选自取代或未取代的C6-C60的芳基或杂芳基，其中杂芳基含有选自B、N、O、S、Si及P中至少一个杂原子，且较佳地至少一个N；X独立的选自O、S、Se、C(R) 2、Si(R) 2、NR、P(＝O)R或羰基，其中R选自H、CN、烷基、芳基。 Among them, in structural formula I, Ar 1 to Ar 4 are independently selected from substituted or unsubstituted C6-C60 aryl or heteroaryl, wherein the heteroaryl contains selected from B, N, O, S, Si and P At least one heteroatom, and preferably at least one N; X is independently selected from O, S, Se, C(R) 2 , Si(R) 2 , NR, P(=O)R or carbonyl, wherein R is selected from From H, CN, alkyl, aryl.
优选的，本发明一种有机化合物独立地选自下列化合物：Preferably, an organic compound of the present invention is independently selected from the following compounds:
Figure PCTCN2020112988-appb-000002
Figure PCTCN2020112988-appb-000002
Figure PCTCN2020112988-appb-000003
Figure PCTCN2020112988-appb-000003
Figure PCTCN2020112988-appb-000004
Figure PCTCN2020112988-appb-000004
Figure PCTCN2020112988-appb-000005
Figure PCTCN2020112988-appb-000005
Figure PCTCN2020112988-appb-000006
Figure PCTCN2020112988-appb-000006
本发明还提供了一种有机电致发光器件，该器件包括阴极层、阳极层和有机层，该有机层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层和电子传输层中至少一层，其中有机层中至少有一层含有如结构式I所表示的化合物。The present invention also provides an organic electroluminescent device. The device includes a cathode layer, an anode layer, and an organic layer. The organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, and an electron injection layer. And at least one of the electron transport layers, wherein at least one of the organic layers contains the compound represented by structural formula I.
其中，结构式I所表示的磷光一种有机化合物如前所述。Among them, the phosphorescent organic compound represented by structural formula I is as described above.
进一步的，结构式I所表示的一种有机化合物作为有机电致发光器件发光层的一种有机材料。Further, an organic compound represented by structural formula I is used as an organic material for the light-emitting layer of an organic electroluminescence device.
进一步的，结构式I所表示的一种有机化合物作为有机电致发光器件发光层的客体掺杂剂。Further, an organic compound represented by structural formula I is used as a guest dopant for the light-emitting layer of the organic electroluminescence device.
进一步的，如结构式I所表示的化合物可以单独使用在有机电致发光器件中，或和其他化合物混合使用；如结构式I所表示的化合物可以使用其中一种化合物，也可以同时使 用结构式I中的两种或两种以上化合物；单独使用一种选自结构式I所述的化合物，或同时使用两种以上选自结构式I所述的化合物。Further, the compound represented by structural formula I can be used alone in organic electroluminescent devices, or used in combination with other compounds; the compound represented by structural formula I can use one of these compounds, or both Two or more compounds; use one compound selected from the structure formula I alone, or use two or more compounds selected from the structure formula I at the same time.
在本发明中，所述发光层可以为红色、黄色或蓝色发光层。在本发明中，所述发光层为蓝色发光层时，采用上述所述的有机电致器件用化合物作为蓝色主体或蓝色掺杂，可得到高效率、高分辨率、高亮度及长寿命的有机电致器件。In the present invention, the light-emitting layer may be a red, yellow or blue light-emitting layer. In the present invention, when the light-emitting layer is a blue light-emitting layer, the above-mentioned compound for organic electro-devices is used as the blue host or blue doping, which can obtain high efficiency, high resolution, high brightness and long length. Life-span organic electro-induced devices.
在本发明中，所述有机物层优选包括电子传输层，所述电子传输层包括上述技术方案所述的有机电致器件用化合物。在本发明中，所述电子传输层优选还包括金属化合物。In the present invention, the organic layer preferably includes an electron transport layer, and the electron transport layer includes the compound for an organic electro-device according to the above technical solution. In the present invention, the electron transport layer preferably further includes a metal compound.
在本发明中，所述有机物层优选包括发光层和电子传输层，所述发光层和电子传输层均含有上述技术方案所述的有机电致器件用化合物，所述发光层和电子传输层中的有机化合物可以相同也可以不同。In the present invention, the organic layer preferably includes a light-emitting layer and an electron-transporting layer, and both the light-emitting layer and the electron-transporting layer contain the compound for an organic electro-device according to the above technical solution, and the light-emitting layer and the electron-transporting layer The organic compounds can be the same or different.
本发明对所述有机电致器件的制备方法没有特殊的限制，除了使用式(I)的有机电致器件用化合物之外，采用本领域技术人员熟知的发光器件的制备方法和材料制备得到即可。The present invention has no special restrictions on the preparation method of the organic electro-device. In addition to the use of the compound for organic electro-device of formula (I), the preparation method and material of the light-emitting device well known to those skilled in the art are used. can.
本发明所述的有机电致器件是有机光伏器件、有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)、有机薄膜晶体管(OTFT)及有机内存器件(Organic Memory Element)中任意一种。The organic electro-induced device of the present invention is an organic photovoltaic device, an organic light-emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-paper), an organic photoreceptor (OPC), an organic thin film transistor (OTFT) and Any of organic memory devices (Organic Memory Element).
在本发明中，有机电致器件是可以利用喷溅涂覆法、电子束蒸发、真空蒸镀等方法在基板上蒸镀金属或具有导电性的氧化物以及它们的合金形成阳极；在制备得到的阳极表面按顺序蒸镀空穴注入层、空穴传输层、发光层、空气阻挡层和电子传输层，以后再蒸镀阴极的方法制备。以上方法以外基板上按阴极、有机物层、阳极顺序蒸镀制作有机电致器件。所述有机物层是也可以包括空穴注入层、空穴传输层、发光层、空穴阻挡层及电子传输层等多层结构。在本发明中有机物层是采用高分子材料按溶剂工程(旋转涂膜(spin-coating)、薄带成型(tape-casting)、刮片法(doctor-blading)、丝网印刷(Screen-Printing)、喷墨印刷或热成像(Thermal-Imaging)等)替代蒸镀方法制备，可以减少器件层数。In the present invention, the organic electro-optical device can use sputter coating, electron beam evaporation, vacuum evaporation and other methods to evaporate metal or conductive oxides and their alloys on the substrate to form an anode; The surface of the anode is prepared by evaporating a hole injection layer, a hole transport layer, a light-emitting layer, an air barrier layer and an electron transport layer in order, and then the cathode is evaporated. In addition to the above methods, organic electro-devices are produced by vapor deposition on the substrate in the order of cathode, organic layer, and anode. The organic layer may also include a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, and an electron transport layer. In the present invention, the organic layer is made of polymer materials according to solvent engineering (spin-coating, tape-casting, doctor-blading, and Screen-Printing). , Inkjet printing or thermal imaging (Thermal-Imaging), etc.) instead of vapor deposition method, can reduce the number of device layers.
根据本发明的有机电致器件所使用的材料可以分为顶发射、低发射或双面发射。根据 本发明实施方案的有机电致器件的化合物可以有机发光器件类似的原理适用于有机太阳能电池、照明的OLED、柔性OLED、有机感光体，有机薄膜晶体管等电致器件方面。The materials used in the organic electro-optical device according to the present invention can be classified into top emission, low emission or double-sided emission. The compound of the organic electro-optical device according to the embodiment of the present invention can be applied to organic solar cells, lighting OLEDs, flexible OLEDs, organic photoreceptors, organic thin-film transistors and other electro-induced devices on a similar principle to organic light-emitting devices.
与现有技术相比，本发明的有益效果是：Compared with the prior art, the beneficial effects of the present invention are:
本发明新型磷光一种有机化合物分子量比较大，通过单键连接的多个共轭平面基团，空间对称性差，不易结晶分解，提高了材料的玻璃化温度，保证了材料长时间蒸镀不被分解；.本发明的有机化合物应用于电致发光器件，具有较大的三线态能级T1能够阻挡激子扩散，提高器件的效率和寿命；本发明的有机磷光一种有机化合物能够平衡空穴和电子的传递，提高器件的寿命。The novel phosphorescent organic compound of the present invention has a relatively large molecular weight, multiple conjugated plane groups connected by single bonds, poor spatial symmetry, difficult to crystallize and decompose, increase the glass transition temperature of the material, and ensure that the material is not vaporized for a long time. Decomposition; The organic compound of the present invention is applied to electroluminescent devices, and has a large triplet energy level T1 that can block exciton diffusion and improve the efficiency and life of the device; the organic phosphorescence of the present invention is an organic compound that can balance holes And the transfer of electrons, improve the life of the device.
附图说明Description of the drawings
图1为本发明的一种有机电致发光二极管器件结构层图；Figure 1 is a structural layer diagram of an organic electroluminescent diode device of the present invention;
其中，110代表基板，120表示阳极，130表示空穴注入层，140表示空穴传输层，150表示发光层，160表示空穴阻挡层，170表示电子传输层，180表示电子注入层，190表示阴极。Among them, 110 represents a substrate, 120 represents an anode, 130 represents a hole injection layer, 140 represents a hole transport layer, 150 represents a light-emitting layer, 160 represents a hole blocking layer, 170 represents an electron transport layer, 180 represents an electron injection layer, and 190 represents cathode.
具体实施方式Detailed ways
为了使本发明的目的、技术方案及优点更加清楚明白，以下结合具体实施例，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。In order to make the objectives, technical solutions, and advantages of the present invention clearer, the following further describes the present invention in detail with reference to specific embodiments. It should be understood that the specific embodiments described here are only used to explain the present invention, but not used to limit the present invention.
中间体的合成流程：The synthetic process of the intermediate:
Figure PCTCN2020112988-appb-000007
Figure PCTCN2020112988-appb-000007
Figure PCTCN2020112988-appb-000008
Figure PCTCN2020112988-appb-000008
1.中间体1-a的合成1. Synthesis of Intermediate 1-a
向500ml圆底烧瓶反应器中投入3-溴-2-碘苯甲酸甲酯(25.0g,73mmol)、2-溴苯硼酸(17.7g,88mmol)、四(三苯基膦)钯(1.7g,0.15mmol)、碳酸钾(20.2g,146.7mmol)，并投入甲苯125mL、四氢呋喃125mL、水50mL。在氮气条件下，使反应器的温度上升到80℃，并搅拌10小时，待反应完毕，将反应器的温度降低至室温，并用乙酸乙酯提取并分离有几层。将有机层减压浓缩后通过柱层析法进行分离，从而获得中间体1-a(15.1g,收率，61％)。Put methyl 3-bromo-2-iodobenzoate (25.0g, 73mmol), 2-bromophenylboronic acid (17.7g, 88mmol), tetrakis (triphenylphosphine) palladium (1.7g) into the 500ml round bottom flask reactor. , 0.15mmol), potassium carbonate (20.2g, 146.7mmol), and put 125mL of toluene, 125mL of tetrahydrofuran, and 50mL of water. Under nitrogen conditions, the temperature of the reactor was raised to 80° C. and stirred for 10 hours. After the reaction was completed, the temperature of the reactor was lowered to room temperature, and extracted with ethyl acetate and separated into several layers. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain Intermediate 1-a (15.1 g, yield, 61%).
2.中间体1-b的合成2. Synthesis of Intermediate 1-b
向500ml圆底烧瓶反应器中投入中间体1-a(15.1g,44.5mmol)、氢氧化钠(2.14g,54mmol)加热回流搅拌使其反应48小时，待反应完毕，将反应器的温度降低至室温，在冷却的溶液中滴加盐酸酸化，将生成的固体搅拌30分钟之后过滤。利用二氯甲烷和正己烷进行重结晶，从而获得中间体1-b(14.1g,收率，89％)。Put Intermediate 1-a (15.1g, 44.5mmol) and sodium hydroxide (2.14g, 54mmol) into a 500ml round bottom flask reactor and heat reflux with stirring to react for 48 hours. When the reaction is complete, reduce the temperature of the reactor To room temperature, add hydrochloric acid dropwise to the cooled solution to acidify, and the resulting solid is stirred for 30 minutes and then filtered. Recrystallization was performed using dichloromethane and n-hexane to obtain Intermediate 1-b (14.1 g, yield, 89%).
3.中间体1-c的合成3. Synthesis of Intermediate 1-c
向250ml圆底烧瓶中投入中间体1-b(14.1g,39.6mmol)、甲磺酸145mL，并加热至80℃反应3小时。利用薄层色谱法确认反应借宿之后冷却至室温。将反应溶液缓慢滴加到冰水150mL之后搅拌30分钟。并将生成的固体过滤之后用水和甲醇进行清洗而获得了中间体1-c(11.1g,收率，83％)。Into a 250 ml round-bottomed flask, intermediate 1-b (14.1 g, 39.6 mmol) and 145 mL of methanesulfonic acid were added, and the mixture was heated to 80° C. to react for 3 hours. It was confirmed by thin layer chromatography that the reaction was completed and then cooled to room temperature. The reaction solution was slowly added dropwise to 150 mL of ice water and then stirred for 30 minutes. The resulting solid was filtered and washed with water and methanol to obtain Intermediate 1-c (11.1 g, yield, 83%).
4.中间体2-a的合成4. Synthesis of Intermediate 2-a
在氮气氛围下，将中间体1-c(11.1g,32.9mmol)、2,2'-联苯二硼酸：8.0g,33.1mmol)、四(三苯基膦)钯(0)：1.1g、碳酸氢钠：10.0g、甲苯：100mL、乙醇：50mL、水：50mL投入烧瓶中，进行12小时的加热回流搅拌。冷却至室温(25℃)后，将反应溶液转移至分液漏 斗中，用甲苯进行萃取。之后，将有机层用硫酸钠进行干燥，进行过滤、浓缩。将残渣用硅胶柱色谱进行纯化，得到了白色固体2-a(6.3g产率58％)。Under a nitrogen atmosphere, the intermediate 1-c (11.1 g, 32.9 mmol), 2,2'-biphenyl diboronic acid: 8.0 g, 33.1 mmol), and tetrakis (triphenylphosphine) palladium (0): 1.1 g , Sodium bicarbonate: 10.0 g, toluene: 100 mL, ethanol: 50 mL, and water: 50 mL were put into the flask, and heated under reflux and stirred for 12 hours. After cooling to room temperature (25°C), the reaction solution was transferred to a separatory funnel and extracted with toluene. After that, the organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography to obtain white solid 2-a (6.3 g, yield 58%).
5.中间体2-b的合成5. Synthesis of Intermediate 2-b
在1L圆底烧瓶中加入2-a(6.3g,19.1mmol)、二氯甲烷180mL并常温搅拌。将溴(3.4mL,66mmol)稀释滴加到二氯甲烷50mL，常温下搅拌8小时，反应完毕后在反应容器中国投入丙酮100mL并搅拌。将生成的固体过滤之后利用丙酮进行清洗。用一氯苯重结晶固体而获得中间体2-b(7.2g,收率，77％)。Add 2-a (6.3 g, 19.1 mmol) and 180 mL of dichloromethane to a 1L round bottom flask and stir at room temperature. Bromine (3.4 mL, 66 mmol) was diluted and added dropwise to 50 mL of dichloromethane, and stirred at room temperature for 8 hours. After the reaction was completed, 100 mL of acetone was poured into the reaction vessel and stirred. After filtering the generated solid, it was washed with acetone. The solid was recrystallized from monochlorobenzene to obtain Intermediate 2-b (7.2 g, yield, 77%).
6.中间体4-c的合成6. Synthesis of Intermediate 4-c
Figure PCTCN2020112988-appb-000009
Figure PCTCN2020112988-appb-000009
在250mL圆底烧瓶中加入4-a(6.2g,25.0mmol)和四氢呋喃100mL，并在氮气氛围下冷却至-78℃。在冷却的反应溶液中将正丁基锂(0.026mol)在相同温度下滴加。将反应溶液反应2小时后，分多次每次加入小量的中间体2-b(7.2g,14.7mmol)，并在常温下搅拌。当反应溶液颜色改变时，利用TLC确认反应结束。投入H2O 50mL使反应结束，并利用乙酸乙酯和水进行萃取。将有机层进行非减压浓缩，然后利用乙腈进行重结晶而获得中间体4-b(7.8g,收率，81％)。A 250 mL round bottom flask was charged with 4-a (6.2 g, 25.0 mmol) and 100 mL of tetrahydrofuran, and cooled to -78°C under a nitrogen atmosphere. In the cooled reaction solution, n-butyllithium (0.026 mol) was added dropwise at the same temperature. After reacting the reaction solution for 2 hours, a small amount of Intermediate 2-b (7.2 g, 14.7 mmol) was added in multiple times and stirred at normal temperature. When the color of the reaction solution changes, use TLC to confirm the end of the reaction. Add 50mL of H2O to complete the reaction, and extract with ethyl acetate and water. The organic layer was concentrated under reduced pressure, and then recrystallized with acetonitrile to obtain Intermediate 4-b (7.8 g, yield, 81%).
在250mL圆底烧瓶中加入4-b(7.8g,11.8mmol)和醋酸120mL、硫酸2mL，并搅拌回流5小时。当固体生成时，利用薄层色谱法确认反应结束，冷却至室温。生成的固体过滤后用水、甲醇清洗，肉厚溶解在一氯苯并进行硅胶过滤、浓缩之后常温冷却，从而获得中间体4-c(6.8g,收率，90％)。生成的化合物通过用LC-MS确定。LC-MS：M/Z 641.0(M+H)+。Add 4-b (7.8 g, 11.8 mmol), 120 mL of acetic acid and 2 mL of sulfuric acid to a 250 mL round bottom flask, and stir and reflux for 5 hours. When solids are formed, confirm the completion of the reaction by thin layer chromatography, and cool to room temperature. The resulting solid was filtered and washed with water and methanol, the meat was thickly dissolved in monochlorobenzene, filtered through silica gel, concentrated, and then cooled at room temperature to obtain Intermediate 4-c (6.8 g, yield, 90%). The resulting compound was confirmed by LC-MS. LC-MS: M/Z 641.0(M+H)+.
7.中间体5-c的合成7. Synthesis of Intermediate 5-c
Figure PCTCN2020112988-appb-000010
Figure PCTCN2020112988-appb-000010
中间体5-c的合同方法同中间体4-c，合成获得中间体5-c(6.9g)。生成的化合物通过用LC-MS确定。LC-MS：M/Z 656.9(M+H)+。The contract method of Intermediate 5-c was the same as Intermediate 4-c, and Intermediate 5-c (6.9g) was obtained by synthesis. The resulting compound was confirmed by LC-MS. LC-MS: M/Z 656.9(M+H)+.
实施例1Example 1
化合物C-6的合成Synthesis of compound C-6
Figure PCTCN2020112988-appb-000011
Figure PCTCN2020112988-appb-000011
在250mL圆底烧瓶中加入(6.8g,10.6mmol)、二(4-甲基苯基)胺(5.0g,25.4mol)、Pd 2(dba) 3(0.08g,0.4mmol)、叔丁醇钠(3.4g,0.035mol)、三叔丁基膦(0.07g,0.4mmol)、甲苯60mL,并回流搅拌2小时。在反应完毕之后常温冷却。利用二氯甲烷和水对反应溶液进行萃取。分离有机层，并用硫酸镁进行干燥，然后减压浓缩。利用柱层析法对物质进行分离提纯，后利用二氯甲烷和丙酮进行重结晶而获得化合物C-6(3.7g，产率40％)。生成的化合物通过用LC-MS确定。LC-MS:M/Z 873.3(M+H) +。理论元素含量(％)C 65H48N 2O：C,89.42；H,5.54；N,3.21；O,1.83。上述结果证实获得产物为目标产品。 Add (6.8g, 10.6mmol), bis(4-methylphenyl)amine (5.0g, 25.4mol), Pd 2 (dba) 3 (0.08g, 0.4mmol), tert-butanol in a 250mL round bottom flask Sodium (3.4g, 0.035mol), tri-tert-butylphosphine (0.07g, 0.4mmol), toluene 60mL, and reflux and stir for 2 hours. After the reaction is completed, it is cooled at room temperature. The reaction solution was extracted with dichloromethane and water. The organic layer was separated, dried with magnesium sulfate, and then concentrated under reduced pressure. The substance was separated and purified by column chromatography, and then recrystallized with dichloromethane and acetone to obtain compound C-6 (3.7 g, yield 40%). The resulting compound was confirmed by LC-MS. LC-MS: M/Z 873.3(M+H) + . Theoretical element content (%) C 65 H48N 2O : C, 89.42; H, 5.54; N, 3.21; O, 1.83. The above results confirm that the obtained product is the target product.
实施例2Example 2
化合物C-9的合成Synthesis of compound C-9
Figure PCTCN2020112988-appb-000012
Figure PCTCN2020112988-appb-000012
化合物C-9的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-9(4.4g，产率38％)。LC-MS：M/Z 1081.4(M+H)+。The synthesis steps of compound C-9 are the same as the above reaction formula, and the preparation and confirmation methods are the same as those of compound C-6, and compound C-9 (4.4 g, yield 38%) can be obtained. LC-MS: M/Z 1081.4(M+H)+.
实施例3Example 3
化合物C-11的合成Synthesis of compound C-11
Figure PCTCN2020112988-appb-000013
Figure PCTCN2020112988-appb-000013
化合物C-11的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-11(4.7g，产率40％)。LC-MS：M/Z 1121.4(M+H)+。The synthesis procedure of compound C-11 is the same as the above reaction formula, and the preparation and confirmation method is the same as that of compound C-6, and compound C-11 (4.7 g, yield 40%) can be obtained. LC-MS: M/Z 1121.4(M+H)+.
实施例4Example 4
化合物C-20的合成Synthesis of compound C-20
Figure PCTCN2020112988-appb-000014
Figure PCTCN2020112988-appb-000014
化合物C-20的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-20(4.1g，产率44％)。LC-MS：M/Z 881.3(M+H)+。The synthesis procedure of compound C-20 is the same as the above reaction formula, and the preparation and confirmation method is the same as that of compound C-6, and compound C-20 (4.1 g, yield 44%) can be obtained. LC-MS: M/Z 881.3(M+H)+.
实施例5Example 5
化合物C-28的合成Synthesis of compound C-28
Figure PCTCN2020112988-appb-000015
Figure PCTCN2020112988-appb-000015
化合物C-28的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-28(4.3g，产率39％)。LC-MS：M/Z 1050.3(M+H)+。The synthesis procedure of compound C-28 is the same as the above reaction formula, and the preparation and confirmation method is the same as that of compound C-6, and compound C-28 (4.3 g, yield 39%) can be obtained. LC-MS: M/Z 1050.3(M+H)+.
实施例6Example 6
化合物C-38的合成Synthesis of compound C-38
Figure PCTCN2020112988-appb-000016
Figure PCTCN2020112988-appb-000016
化合物C-38的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-38(4.4g，产率45％)。LC-MS：M/Z 917.3(M+H)+。The synthesis steps of compound C-38 are as the above reaction formula, and the preparation and confirmation methods are the same as those of compound C-6, and compound C-38 (4.4 g, yield 45%) can be obtained. LC-MS: M/Z 917.3(M+H)+.
实施例7Example 7
化合物C-43的合成Synthesis of compound C-43
Figure PCTCN2020112988-appb-000017
Figure PCTCN2020112988-appb-000017
化合物C-43的合成步骤如上述反应式，制备及确认方法同化合物C-6，可获得化合物C-43(3.7g，产率40％)。LC-MS：M/Z 861.3(M+H)+。The synthesis steps of compound C-43 are the same as the above reaction formula, and the preparation and confirmation methods are the same as those of compound C-6, and compound C-43 (3.7 g, yield 40%) can be obtained. LC-MS: M/Z 861.3(M+H)+.
本发明还通过热蒸镀的方式制备了10个底发光器件(各个具体的器件结构如下：The present invention also prepares 10 bottom light emitting devices by means of thermal evaporation (each specific device structure is as follows:
器件实施例：Device embodiment:
将费希尔公司涂层厚度为
Figure PCTCN2020112988-appb-000018
的ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30分钟，再用蒸馏水反复清洗2次，超声波洗涤10分钟，蒸馏水清洗结束后，采用异丙醇、丙酮、甲醇溶剂按顺序进行超声波洗涤后干燥，将干燥后的基板转移到等离子体清洗机里，将上述基板洗涤5分钟后送到蒸镀机里。 The coating thickness of Fisher Company is
Figure PCTCN2020112988-appb-000018
The ITO glass substrate is cleaned twice in distilled water, ultrasonically cleaned for 30 minutes, and then repeatedly cleaned with distilled water for two times, ultrasonically cleaned for 10 minutes, after the distilled water cleaning is completed, use isopropanol, acetone, methanol solvents to perform ultrasonic cleaning in order After drying, the dried substrate is transferred to a plasma cleaning machine, and the substrate is washed for 5 minutes and then sent to the vapor deposition machine.
在已经清洗好的ITO透明电极上依次蒸镀空穴注入层2-TNATA蒸镀厚度为
Figure PCTCN2020112988-appb-000019
空穴传输层a-NPD蒸镀厚度为
Figure PCTCN2020112988-appb-000020
ADN(9,10-二(2-萘基)蒽)和5％的BD1～BD3或本发明一种有机化合物蒸镀厚度为
Figure PCTCN2020112988-appb-000021
空穴阻挡层及电子传输层TPBi蒸镀厚度为
Figure PCTCN2020112988-appb-000022
LiF蒸镀厚度为
Figure PCTCN2020112988-appb-000023
和Al蒸镀厚度为
Figure PCTCN2020112988-appb-000024
形成阴极；上述过程有机物蒸镀速度保持
Figure PCTCN2020112988-appb-000025
Figure PCTCN2020112988-appb-000026
LiF的蒸镀速度为
Figure PCTCN2020112988-appb-000027
Al的蒸镀速度为
Figure PCTCN2020112988-appb-000028
On the cleaned ITO transparent electrode, the hole injection layer 2-TNATA vapor deposition thickness is sequentially evaporated
Figure PCTCN2020112988-appb-000019
The hole transport layer a-NPD evaporation thickness is
Figure PCTCN2020112988-appb-000020
ADN (9,10-bis(2-naphthyl)anthracene) and 5% of BD1～BD3 or an organic compound of the present invention. The vapor deposition thickness is
Figure PCTCN2020112988-appb-000021
The hole blocking layer and electron transport layer TPBi evaporation thickness is
Figure PCTCN2020112988-appb-000022
The thickness of LiF evaporation is
Figure PCTCN2020112988-appb-000023
And Al evaporation thickness is
Figure PCTCN2020112988-appb-000024
The cathode is formed; the organic vapor deposition speed is maintained during the above process
Figure PCTCN2020112988-appb-000025
Figure PCTCN2020112988-appb-000026
The evaporation rate of LiF is
Figure PCTCN2020112988-appb-000027
The vapor deposition rate of Al is
Figure PCTCN2020112988-appb-000028
Figure PCTCN2020112988-appb-000029
Figure PCTCN2020112988-appb-000029
表1为本发明实施例和比较例制备得到的有机发光器件的性能检测结果。Table 1 shows the performance test results of the organic light-emitting devices prepared in the embodiment of the present invention and the comparative example.
[表1][Table 1]
Figure PCTCN2020112988-appb-000030
Figure PCTCN2020112988-appb-000030
Figure PCTCN2020112988-appb-000031
Figure PCTCN2020112988-appb-000031
从上述表1结果中，采用本发明提供的有机电致器件用化合物制备有机电致器件，有机电致器件的发光效率和寿命特性显著提高。From the results in Table 1 above, using the compound for organic electro-devices provided by the present invention to prepare organic electro-devices, the luminous efficiency and life characteristics of the organic electro-devices are significantly improved.
以上所述，仅为本发明较佳的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明揭露的技术范围内，根据本发明的技术方案及其发明构思加以等同替换或改变，都应涵盖在本发明的保护范围之内。The above are only the preferred specific embodiments of the present invention, but the protection scope of the present invention is not limited to this. Anyone familiar with the technical field within the technical scope disclosed in the present invention, according to the technical solution of the present invention The equivalent replacement or change of the inventive concept thereof shall all fall within the protection scope of the present invention.

Claims (7)

  1. 一种应用于有机电致发光领域的有机化合物，该有机化合物的分子结构式为结构式I所示结构；An organic compound used in the field of organic electroluminescence, the molecular structural formula of the organic compound is the structure shown in structural formula I;
    Figure PCTCN2020112988-appb-100001
    Figure PCTCN2020112988-appb-100001
    其特征在于，结构式I中，Ar 1至Ar 4独立地选自取代或未取代的C6-C60的芳基或杂芳基，其中杂芳基含有选自B、N、O、S、Si及P中至少一个杂原子，且较佳地至少一个N；X独立的选自O、S、Se、C(R) 2、Si(R) 2、NR、P(＝O)R或羰基，其中R选自H、CN、烷基、芳基。 It is characterized in that, in structural formula I, Ar 1 to Ar 4 are independently selected from substituted or unsubstituted C6-C60 aryl or heteroaryl, wherein the heteroaryl contains selected from B, N, O, S, Si and At least one heteroatom in P, and preferably at least one N; X is independently selected from O, S, Se, C(R) 2 , Si(R) 2 , NR, P(=O)R or carbonyl, wherein R is selected from H, CN, alkyl, and aryl.
  2. 根据权利要求1所述的一种应用于有机电致发光领域的有机化合物，其特征在于：所述有机化合物独立地选自下列化合物：The organic compound used in the field of organic electroluminescence according to claim 1, wherein the organic compound is independently selected from the following compounds:
    Figure PCTCN2020112988-appb-100002
    Figure PCTCN2020112988-appb-100002
    Figure PCTCN2020112988-appb-100003
    Figure PCTCN2020112988-appb-100003
    Figure PCTCN2020112988-appb-100004
    Figure PCTCN2020112988-appb-100004
    Figure PCTCN2020112988-appb-100005
    Figure PCTCN2020112988-appb-100005
    Figure PCTCN2020112988-appb-100006
    Figure PCTCN2020112988-appb-100006
    Figure PCTCN2020112988-appb-100007
    Figure PCTCN2020112988-appb-100007
  3. 一种有机电致发光器件，包括阴极层、阳极层和有机层，该有机层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层、电子传输层中的至少一层，其特征在于：该器件的有机层中至少有一层含有如权利要求1所述的有机化合物。An organic electroluminescence device, comprising a cathode layer, an anode layer and an organic layer. The organic layer includes at least a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron injection layer, and an electron transport layer. A layer, characterized in that: at least one of the organic layers of the device contains the organic compound according to claim 1.
  4. 根据权利要求3所述的有机电致发光器件，其特征在于，有机电致发光器件发光层中含有权利要求1所述的化合物。The organic electroluminescence device according to claim 3, wherein the light-emitting layer of the organic electroluminescence device contains the compound according to claim 1.
  5. 根据权利要求3或权利要求4所述的有机电致发光器件，其特征在于，权利要求1所述的化合物在有机电致发光器件发光层中作为客体掺杂剂使用。The organic electroluminescent device of claim 3 or claim 4, wherein the compound of claim 1 is used as a guest dopant in the light-emitting layer of the organic electroluminescent device.
  6. 根据权利要求3所述的有机电致发光器件，其特征在于，权利要求1所述的化合物可以单独使用，或和其他化合物混合使用。The organic electroluminescent device according to claim 3, wherein the compound according to claim 1 can be used alone or mixed with other compounds.
  7. 根据权利要求3所述的有机电致发光器件，其特征在于，单独使用一种选自如权利要求2所述的有机化合物，或同时使用两种或两种以上选自如权利要求2所述的有机化合物。The organic electroluminescence device according to claim 3, wherein one kind selected from the organic compound according to claim 2 is used alone, or two or more kinds selected from the organic compound according to claim 2 are used simultaneously. Compound.
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