WO2022257584A1 - Compound, organic electroluminescence device containing same, and electronic device - Google Patents

Compound, organic electroluminescence device containing same, and electronic device Download PDF

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WO2022257584A1
WO2022257584A1 PCT/CN2022/085688 CN2022085688W WO2022257584A1 WO 2022257584 A1 WO2022257584 A1 WO 2022257584A1 CN 2022085688 W CN2022085688 W CN 2022085688W WO 2022257584 A1 WO2022257584 A1 WO 2022257584A1
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group
groups
identically
differently
aromatic
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曹建华
戴雄
张海威
谢佩
李程辉
刘赛赛
郭文龙
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北京八亿时空液晶科技股份有限公司
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Definitions

  • the present invention relates to a compound, and materials containing the compound for use in organic electroluminescent devices, and to organic electroluminescent devices and electronic equipment containing these materials.
  • OLED organic electroluminescence
  • EL organic light-emitting
  • organic electroluminescence display technology has become mature, and some products have entered the market, but there are still many problems to be solved in the process of industrialization.
  • organic materials used to make components there are still many problems in their carrier injection and transport performance, material electroluminescence performance, service life, color purity, matching between various materials and between electrodes, etc.
  • the problem is not resolved.
  • the luminous efficiency and service life of light-emitting elements have not yet met the practical requirements, which greatly limits the development of OLED technology.
  • Metal complex phosphorescent materials that use triplet light emission have high luminous efficiency, and their green and red light materials have met the requirements for use.
  • metal complexes have special electronic structure characteristics, which makes their blue light materials unable to meet the use requirements.
  • the present invention was made in view of the above situation and it was an object to provide compounds suitable for use in fluorescent or phosphorescent OLEDs, in particular in phosphorescent OLEDs, for example as hole-transport material in a hole-transport layer or in an exciton-blocking layer Or as a matrix material in the light-emitting layer.
  • the present invention adopts the following technical solutions:
  • each occurrence of L is, identically or differently, an aromatic ring system, wherein each L may be substituted by one or more groups R;
  • x is selected from 0, 1, 2, 3 or 4;
  • B represents an aromatic ring system or -NAr 3 Ar 4 , where L can also be linked to Ar 3 and/or Ar 4 via a group E;
  • W 1 to W 4 represent N or CR 2 identically or differently, or any two adjacent groups W 1 , W 2 , W 3 , W 4 represent groups represented by the following formula (II) or (III) ,
  • Z represents CR 3 or N identically or differently at each occurrence, and ⁇ indicates the corresponding adjacent groups W 1 and W 2 , W 2 and W 3 , or W 3 and W 4 in formula I;
  • T, E are selected from O, S, NAr 5 or CR 4 R 5 ;
  • Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 are, identically or differently at each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, each of which ring systems can be Substituted by one or more groups R 1 ; Ar 1 and Ar 2 , Ar 3 and Ar 4 may optionally be joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system;
  • R 7 is selected from a hydrogen atom, a deuterium atom, a fluorine atom, a nitrile group, an aliphatic hydrocarbon group with C 1 to C 20 , an aromatic ring or a heteroaromatic ring system with 5 to 30 carbon atoms, one or more of which A hydrogen atom can be replaced by a deuterium atom, a halogen atom or a nitrile group, wherein any adjacent two or more adjacent R 7 can form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system with each other.
  • the compound of formula (I) is selected from the compounds shown in formula IV, V, VI, VII, VIII, IX:
  • Z, W 1 , W 2 , W 3 or W 4 in the compound of formula IV, V, VI, VII, VIII or IX is particularly preferably represented by CH.
  • the groups B, Ar 1 , Ar 2 , Ar 3 , Ar 4 or Ar 5 are identically or differently selected from the groups of formulas (2) to (27) at each occurrence Groups composed of:
  • the dotted line key indicates the position of connection with N, and the symbols used have the meanings given above.
  • the group R 1 in the formulas (2) to (27) is particularly preferably represented by hydrogen.
  • said group Ar 1 or Ar 2 is a group of formula (2), (3), (4), (5) or (13), and in particular of formula (2 ), (3), (4), (5) or (13) in R 1 is preferably a hydrogen group, in the case of Ar 1 or Ar 2 for these groups, for organic electroluminescent devices, to achieve very good results.
  • said radicals Ar 1 and Ar 2 are different from each other.
  • the group L-NAr 3 Ar 4 preferably has one of the formulas (33), (34), (35), (36) or (37) Structure:
  • the label x 1 or 2
  • R 1 in the group —(L) x— is particularly preferably represented by hydrogen.
  • the label x 0
  • the group B is selected from the group consisting of groups of formulas (2) to (27)
  • R in the group B 1 is particularly preferably represented by hydrogen.
  • R 1 to R 5 are identically or differently selected from hydrogen atom, deuterium atom, halogen atom, nitrile group, Si(R 6 ) 3 , having C 1 to C 10 linear alkyl or alkoxy groups, C 3 to C 10 branched or cyclic alkyl or alkoxy groups, each of which may be replaced by one or more A group R 6 substituted, wherein in each case one or more non-adjacent -CH 2 - groups may be replaced by O, and wherein one or more hydrogen atoms may be replaced by deuterium atoms or halogen atoms, with 5 80, preferably 5 to 60 carbon atoms of aromatic or heteroaromatic ring systems, which may in each case be the same or different, which may in each case be replaced by one or more A group R is substituted, wherein two or more adjacent substituents may optionally be joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring systems, wherein two or more adjacent
  • radical R 1 is bonded to Ar 1 or Ar 2 or R 1 to Ar 3 or Ar 4 , said radical R 1 is identical or different at each occurrence It is selected from a hydrogen atom or a deuterium atom, a linear alkyl group having C 1 to C 10 or a branched or cyclic alkyl group having C 3 to C 10 .
  • the substituents R 2 or R 1 can preferably together form a cycloalkyl ring which preferably has 3 to 8 carbon atoms, particularly preferably 5 to 6 carbon atoms.
  • R 1 bonded to the carbon bridging group in formula (28) or (33) is selected at each occurrence identically or differently from linear alkyl groups having C 1 to C 10 or a branched or cyclic alkyl group having C 3 to C 10 , or an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, which may in each case be replaced by one or a plurality of radicals R 2 are substituted; in addition to the limitations given above for R 1 , here two radicals R 1 can also form with one another a ring system, which can be aliphatic or aromatic, Spirocyclic systems are formed by ring formation.
  • R 1 bonded to the nitrogen bridge group is selected from linear alkyl groups with C 1 to C 10 , straight chain alkyl groups with C 3 to C 10 A branched or cyclic alkyl group, or an aromatic ring or heteroaromatic ring system having 5 to 60 carbon atoms, especially an aromatic ring system having 6 to 24 carbon atoms, which in each Cases may be substituted by one or more groups R2 .
  • R 2 is identically or differently selected from a hydrogen atom, a deuterium atom, a straight-chain alkyl group having C 1 to C 5 , a branched or cyclic alkyl group having C 3 to C 6 , and a group having 5 to 5 An aromatic ring or heteroaromatic ring system of 18 carbon atoms.
  • Aryl in the sense of the present invention contains 6 to 60 carbon atoms
  • heteroaryl in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5 ; the heteroatom is preferably selected from N, O or S.
  • aryl or heteroaryl is taken to mean simple aromatic rings, i.e. benzene, naphthalene, etc., or simple heteroaromatic rings, such as pyridine, pyrimidine, thiophene, etc., or fused aryl or heteroaryl Groups, such as anthracene, phenanthrene, quinoline, isoquinoline, etc.
  • Aromatic rings connected to one another via single bonds, such as biphenyl are conversely not referred to as aryl or heteroaryl, but as aromatic ring systems.
  • Aromatic ring systems in the sense of the present invention are in particular also intended to be taken to mean systems which do not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups can also be formed by non-aromatic units such as C , N, O or S atom connection.
  • aryl groups are linked by, for example, short alkyl groups such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, Systems of diaryl ethers etc. are also taken to mean aromatic ring systems in the sense of the present invention.
  • Aliphatic hydrocarbon radicals or alkyl or alkenyl or alkynyl radicals containing 1 to 40 carbon atoms in the sense of the present invention and in which individual hydrogen atoms or -CH2- radicals may also be substituted by the aforementioned radicals are preferably considered to be Refers to the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, Neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cyclohepty
  • Alkoxy preferably having 1 to 40 carbon atoms is considered methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy radical, sec-butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n- Octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy.
  • Heteroalkyl is preferably an alkyl group having 1 to 40 carbon atoms, and refers to a group in which individual hydrogen atoms or -CH2- groups may be replaced by oxygen, sulfur, halogen atoms, and is considered to mean alkoxy, Alkylthio, fluorinated alkoxy, fluorinated alkylthio, especially methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butyl Oxygen, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio group, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethoxy,
  • cycloalkyl, cycloalkenyl can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl , cycloheptenyl, wherein one or more -CH 2 - groups can be replaced by the above groups; in addition, one or more hydrogen atoms can also be replaced by deuterium atoms, halogen atoms or nitrile groups.
  • Aromatic or heteroaromatic ring atoms according to the invention, aromatic or heteroaromatic ring systems which may in each case also be substituted by the abovementioned radicals R in particular mean radicals derived from benzene, Naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, Perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenyl, terphenyl, tripolyphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis Or trans indenofluorene, cis or trans indenocarbazole, cis or trans indolocarbazole, tripolyindene, isotripolyindene, spirothree polyindene, spiroisotripolyindene,
  • Examples of compounds according to the invention mainly include the compounds shown in the table below:
  • Another aspect of the present invention is a material for an organic electroluminescence device, which comprises the compound of the present invention.
  • an organic electroluminescent element/device comprising a cathode, an anode and at least one light emitting layer. Besides these layers it may also contain further layers, for example in each case one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, excitation layers, sub-blocking layer, electron blocking layer and/or charge generating layer. Interlayers having, for example, an exciton-blocking function can likewise be introduced between two emitting layers. It should be noted, however, that not every one of these layers is required to be present.
  • the organic electroluminescent device described herein may comprise one light-emitting layer, or it may comprise a plurality of light-emitting layers.
  • various light-emitting compounds capable of emitting light are used in the light-emitting layer.
  • Particular preference is given to systems with three emitting layers, the three layers being able to exhibit blue, green and red emission. If more than one emitting layer is present, according to the invention at least one of these layers comprises a compound according to the invention.
  • the compounds of the formula (I) or preferred embodiments can be used both in the hole-transport layer or in the exciton-blocking layer and as matrix in the emitting layer.
  • organic electroluminescent components in which one or more layers are applied by means of a sublimation method by vapor deposition in a vacuum sublimation apparatus at an initial pressure below 10 ⁇ 5 Pa, preferably below 10 ⁇ 6 Pa. Apply the material.
  • the initial pressure may also be even lower, for example below 10 ⁇ 7 Pa.
  • a particular example of this method is the organic vapor jet printing method, in which the material is applied directly via a nozzle and is thus structured.
  • organic electroluminescent elements which, from solution, for example by spin coating, or by means of any desired printing method, such as screen printing, flexographic printing, lithography, photoinduced thermography, thermal transfer, spray Ink printing or nozzle printing to produce one or more layers.
  • Soluble compound for example, the soluble compound can be obtained by modifying the compound represented by the formula (I) of the present invention by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Also possible are hybrid methods in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
  • the organic electroluminescent component according to the invention does not comprise a separate hole-injection layer and/or hole-transport layer and/or hole-blocking layer and/or electron-transport layer, i.e. emits light
  • a layer is directly adjacent to a hole injection layer or an anode, and/or an emissive layer is directly adjacent to an electron transport layer or an electron injection layer or a cathode.
  • the invention therefore also relates to a method for producing an organic electroluminescent element according to the invention, at least one layer being applied by means of a sublimation method and/or at least one layer being applied by means of an organic vapor deposition method or by means of sublimation of a carrier gas , and/or apply at least one layer from solution by spin coating or by means of a printing method.
  • the present invention relates to compounds comprising at least one of the above indicated compounds.
  • the compounds can preferably also comprise further compounds.
  • the processing of the compounds according to the invention from the liquid phase requires the formulation of the compounds according to the invention. These formulations may, for example, be solutions, dispersions or emulsions. For this purpose, mixtures of two or more solvents may preferably be used.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, Tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenzone, 1,2,3,5-tetramethylbenzene, 1,2, 4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-Dimethylanisole, 3,5-Dimethylanisole, Acetophenone, ⁇ -Terpineol, Benzothiazole, Butyl Benzoate, Cumene, Cyclohexanol, Cyclohe
  • the organic electroluminescent element of the present invention can be either a top-emitting light element or a bottom-emitting light element.
  • the structure and preparation method of the organic electroluminescent element of the present invention are not limited.
  • the organic electroluminescent element prepared by using the compound of the invention can reduce the starting voltage and improve the luminous efficiency and brightness.
  • Still another aspect of the present invention is an electronic device including the organic electroluminescent element of the present invention.
  • the electronic device can be used in various applications, for example for monochrome or multicolor displays, for lighting applications or for medical and/or cosmetic applications, for example in phototherapy.
  • the compounds according to the invention are very suitable for use in hole-transport or hole-injection layers in organic electroluminescent components. They are also suitable in particular for use in layers directly adjacent to the phosphorescent emitting layer, since the compounds according to the invention do not annihilate the emission.
  • the compounds according to the invention lead to very high efficiencies and long lifetimes, which is especially suitable if the compounds are used as matrix materials together with other matrix materials and phosphorescent emitters point.
  • the compounds according to the invention lead to high efficiencies and, in the case of use and low operating voltages, to steep current-voltage curves.
  • the compounds according to the invention have high thermal stability and are capable of sublimation without decomposition and without residues.
  • the compounds according to the invention have a high oxidation stability, which has particularly positive effects on the handling of these compounds and on the storage stability of solutions.
  • FIG. 1 shows a schematic diagram of an example of bottom emission of the organic electroluminescent device of the present invention.
  • FIG. 2 shows a schematic diagram of an example of top emission of the organic electroluminescent device of the present invention.
  • the raw materials used in the present invention can be obtained commercially, and any range described in the present invention includes the end value and any value between the end value and the end value or any value between the end value Any subrange formed by .
  • the preparation methods are conventional methods unless otherwise specified.
  • the raw materials used can be obtained from public commercial sources unless otherwise specified, and the stated percentages are all mass percentages unless otherwise specified.
  • Luminance and chromaticity coordinates tested using spectral scanner PhotoResearch PR-715;
  • Life test use LTS-1004AC life test device.
  • the preparation method of compound CJHL461 ⁇ CJHL586 comprises the following steps:
  • the first step preparation of compound Int-1
  • the OLED element provided by the present invention is shown in FIG. 1 and FIG. 2 .
  • the organic electroluminescent device has a substrate 1 , an anode 2 , a cathode 8 , and layers 3 to 7 arranged between the anode 2 and the cathode 8 .
  • a hole blocking/electron transport layer 6 and an electron injection layer 7 are arranged between the cathode 8 and the light emitting layer 5, and a hole injection layer 3 and a hole transport/electron blocking layer are arranged between the light emitting layer 5 and the anode 2.
  • the aforementioned compound C is replaced by the compound of the present invention, except that, the same method is used to make the organic electroluminescent element: ITO/compound of the present invention+F4( 3%)
  • the drive voltage of the element prepared by the organic material of the present invention is low, the external quantum efficiency is high, and the color purity is good, and under the condition that the luminous brightness of the element is initially 1000 nits as the benchmark, the compound of the present invention is used as an empty space.
  • the device life of the hole injection layer material is much better.
  • the drive voltage of the element prepared by the organic material of the present invention is low, the external quantum efficiency is high, and the color purity is good, and under the condition that the luminous brightness of the element is initially 1000 nits as the benchmark, the compound of the present invention is used as the electronic component.
  • the component life of the barrier material is much better.

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Abstract

The present invention relates to a compound, which has a structural formula shown in formula (I) and is suitable for use in electronic components, especially in organic electroluminescence devices, and relates to a material for organic electroluminescence elements and organic electroluminescence device containing the compound, and an electronic device. The use of the compound in organic electroluminescent devices achieves high efficiency and a long service life and produces positive results.

Description

化合物和包含该化合物的有机电致发光装置和电子设备Compound and organic electroluminescent device and electronic device comprising the same 技术领域technical field
本发明涉及一种化合物，以及含有该化合物的用于有机电致发光装置中的材料，并且涉及包含这些材料的有机电致发光装置和电子设备。The present invention relates to a compound, and materials containing the compound for use in organic electroluminescent devices, and to organic electroluminescent devices and electronic equipment containing these materials.
背景技术Background technique
早在1963年，pope等人首先发现了有机化合物单晶蒽的电致发光现象，开启了有机电致发光(简称OLED)及相关的研究。经过二十几年的发展，有机发光(简称EL)材料已经全面实现了红、蓝、绿色发光，应用领域也从小分子扩展到了高分子以及金属络合物等领域。As early as 1963, Pope et al. first discovered the electroluminescence phenomenon of organic compound single crystal anthracene, which opened the organic electroluminescence (referred to as OLED) and related research. After more than 20 years of development, organic light-emitting (EL) materials have fully realized red, blue, and green light, and their application fields have also expanded from small molecules to polymers and metal complexes.
最近几年有机电致发光显示技术己趋于成熟，一些产品已进入市场，但在产业化时程中，仍有许多问题亟待解决。特别是用于制作元件的各种有机材料，其载流子注入和传输性能、材料电发光性能、使用寿命、色纯度、各种材料之间及与各电极之间的匹配等，尚有许多问题还未解决。尤其是发光元件在发光效率和使用寿命还达不到实用化要求，这大大限制了OLED技术的发展。而利用三线态发光的金属配合物磷光材料具有高的发光效率，其绿光和红光材料已经达到使用要求，但是金属配合物具有特殊的电子结构特征，导致其蓝光材料无法达到使用要求。In recent years, organic electroluminescence display technology has become mature, and some products have entered the market, but there are still many problems to be solved in the process of industrialization. Especially for various organic materials used to make components, there are still many problems in their carrier injection and transport performance, material electroluminescence performance, service life, color purity, matching between various materials and between electrodes, etc. The problem is not resolved. In particular, the luminous efficiency and service life of light-emitting elements have not yet met the practical requirements, which greatly limits the development of OLED technology. Metal complex phosphorescent materials that use triplet light emission have high luminous efficiency, and their green and red light materials have met the requirements for use. However, metal complexes have special electronic structure characteristics, which makes their blue light materials unable to meet the use requirements.
在目前的技术发展下，无论是对于荧光材料还是对于磷光材料，特别是在用于有机电致发光器件中的工作电压、效率和寿命方面和在升华期间的热稳定性方面，都还需要改进。Under the current technological development, both for fluorescent materials and phosphorescent materials, especially in terms of operating voltage, efficiency and lifetime used in organic electroluminescent devices and thermal stability during sublimation, there is still a need for improvement .
发明内容Contents of the invention
本发明鉴于上述情况而做出，目的在于提供适合用于荧光或磷光OLED中，特别是用于磷光OLED中的化合物，该化合物例如作为空穴传输层或激子阻挡层中的空穴传输材料或作为发光层中的基质材料。The present invention was made in view of the above situation and it was an object to provide compounds suitable for use in fluorescent or phosphorescent OLEDs, in particular in phosphorescent OLEDs, for example as hole-transport material in a hole-transport layer or in an exciton-blocking layer Or as a matrix material in the light-emitting layer.
令人惊讶地发现，在下文中更详细描述的特定化合物实现了这种目的，并且特别是在寿命、效率和工作电压方面在有机电致发光元件中引起了显著的改进。特别是将本发明的化合物用作空穴传输材料或用作基质材料时，这种情况适用于磷光和荧光的电致发光元件。所述材料通常具有高的热稳定性，并且因此能够在没有分解和没有残余物的情况下进行升华。因此，本发明涉及这些材料，并且涉及包含这种类型的化合物的电子元件。特别地，使用芳族单胺获得了非常好的结果，这是令人惊讶的结果，因为含有至少两个氮原子的空穴传输材料通常被用于有机电致发光元件中。It has surprisingly been found that the specific compounds described in more detail below achieve this object and lead to a marked improvement in organic electroluminescent components, in particular with regard to lifetime, efficiency and operating voltage. This applies to phosphorescent and fluorescent electroluminescent components, in particular when the compounds according to the invention are used as hole-transport materials or as matrix materials. Said materials generally have high thermal stability and are therefore capable of sublimation without decomposition and without residues. Accordingly, the present invention relates to these materials, and to electronic components comprising compounds of this type. In particular, very good results were obtained with aromatic monoamines, which is surprising since hole-transport materials containing at least two nitrogen atoms are generally used in organic electroluminescent elements.
为达到上述目的，本发明采用下述技术方案：To achieve the above object, the present invention adopts the following technical solutions:
一种化合物，其结构式如下述的式(I)所示：A kind of compound, its structural formula is shown in following formula (I):
Figure PCTCN2022085688-appb-000001
Figure PCTCN2022085688-appb-000001
其中，L在每次出现时相同或不同地为芳族环系，其中的每个L可以被一个或多个基团R 1取代； wherein each occurrence of L is, identically or differently, an aromatic ring system, wherein each L may be substituted by one or more groups R;
x选自0、1、2、3或4；x is selected from 0, 1, 2, 3 or 4;
B表示芳族环系或-NAr 3Ar 4，在此处L还可以通过基团E与Ar 3和/或Ar 4连接； B represents an aromatic ring system or -NAr 3 Ar 4 , where L can also be linked to Ar 3 and/or Ar 4 via a group E;
W 1～W 4相同或不同地代表N或CR 2，或者任意两个相邻的基团W 1、W 2、W 3、W 4代表下式(II)或(III)所示的基团， W 1 to W 4 represent N or CR 2 identically or differently, or any two adjacent groups W 1 , W 2 , W 3 , W 4 represent groups represented by the following formula (II) or (III) ,
Figure PCTCN2022085688-appb-000002
Figure PCTCN2022085688-appb-000002
其中，Z在每次出现时相同或不同地代表CR 3或N，并且^指示式I中的相应的相邻基团W 1和W 2、W 2和W 3，或W 3和W 4； wherein Z represents CR 3 or N identically or differently at each occurrence, and ^ indicates the corresponding adjacent groups W 1 and W 2 , W 2 and W 3 , or W 3 and W 4 in formula I;
T、E选自O、S、NAr 5或CR 4R 5； T, E are selected from O, S, NAr 5 or CR 4 R 5 ;
Ar 1、Ar 2、Ar 3、Ar 4、Ar 5在每次出现时相同或不同地为具有5至60个碳原子的芳族或杂芳族环系，所述环系中的每个可以被一个或多个基团R 1取代；Ar 1和Ar 2、Ar 3和Ar 4可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系； Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 are, identically or differently at each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, each of which ring systems can be Substituted by one or more groups R 1 ; Ar 1 and Ar 2 , Ar 3 and Ar 4 may optionally be joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system;
R 1～R 5在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、Si(R 6) 3、具有C 1～C 40的直链烷基、具有C 1～C 40的直链杂烷基、具有C 3～C 40的支链或环状的烷基、具有C 3～C 40的支链或环状的杂烷基、具有C 2～C 40的烯基或炔基基团，所述基团中的每个可被一个或多个基团R 6取代，其中在每种情况下一个或多个非相邻的-CH 2-基团可被R 6C＝CR 6、C≡C、Si(R 6) 2、Ge(R 6) 2、Sn(R 6) 2、C＝O、C＝S、C＝Se、C＝NR 6、P(＝O)(R 6)、SO、SO 2、NR 6、O、S或CONR 6代替，并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替，具有5至80个、优选5至60个碳原子的芳族环或杂芳蔟环系、具有5至60个碳原子的芳氧基或杂芳氧基组成的组，其在每种情况下可以被一个或多个基团R 6取代，或这些基团中的两个、三个、四个或五个的组合，其在每种情况下可以是相同的或不同的，其中两个或更多个相邻的取代基可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系，所述环系可被一个或多个基团R 6取代； R 1 to R 5 are identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, Si(R 6 ) 3 , a linear alkyl group having C 1 to C 40 , a straight chain alkyl group having C 1 ~C 40 straight chain heteroalkyl, C 3 ~C 40 branched or cyclic alkyl, C 3 ~C 40 branched or cyclic heteroalkyl, C 2 ~C 40 Alkenyl or alkynyl groups, each of which may be substituted by one or more radicals R 6 , wherein in each case one or more non-adjacent —CH 2 — groups may be replaced by R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P (=O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 instead, and wherein one or more hydrogen atoms can be replaced by deuterium atom, halogen atom, nitrile group or nitro group, with 5 to 80, preferably 5 to 60, carbon atoms of aromatic rings or heteroaryl ring systems, aryloxy or heteroaryloxy groups having 5 to 60 carbon atoms, which in each case may be Substitution by one or more groups R 6 , or combinations of two, three, four or five of these groups, which in each case may be the same or different, where two or more Two adjacent substituents may optionally be joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more groups R ;
R 6在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、Si(R 7) 3、具有C 1～C 40的直链烷基、具有C 1～C 40的直链杂烷基、具有C 3～C 40的支链或环状的烷基、具有 C 3～C 40的支链或环状的杂烷基、具有C 2～C 40的烯基或炔基，所述基团中的每个可被一个或多个基团R 7取代，其中一个或多个非相邻的-CH 2-基团可被R 7C＝CR 7、C≡C、Si(R 7) 2、Ge(R 7) 2、Sn(R 7) 2、C＝O、C＝S、C＝Se、C＝NR 7、P(＝O)(R 7)、SO、SO 2、NR 7、O、S或CONR 7代替，并且其中一个或多个氢原子可被氘原子、卤素原子或腈基代替，具有5至60个碳原子的芳族环或杂芳蔟环系、具有5至60个碳原子的芳氧基或杂芳氧基组成的组，其在每种情况下可以是相同的或不同的，其在每种情况下可以被一个或多个基团R 7取代，其中两个或更多个相邻的取代基R 6可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系，所述环系可被一个或多个基团R 7取代； R 6 is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, Si(R 7 ) 3 , a linear alkyl group having C 1 to C 40 , a straight chain alkyl group having C 1 to C 40 straight-chain heteroalkyl, branched or cyclic alkyl with C 3 to C 40 , branched or cyclic heteroalkyl with C 3 to C 40 , alkenyl with C 2 to C 40 or Alkynyl, each of which may be substituted by one or more groups R 7 , wherein one or more non-adjacent -CH 2 - groups may be replaced by R 7 C=CR 7 , C≡C , Si(R 7 ) 2 , Ge(R 7 ) 2 , Sn(R 7 ) 2 , C=O, C=S, C=Se, C=NR 7 , P(=O)(R 7 ), SO , SO 2 , NR 7 , O, S or CONR 7 instead, and wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms or nitrile groups, aromatic rings or heteroaryl clusters having 5 to 60 carbon atoms ring system, group consisting of aryloxy or heteroaryloxy groups having 5 to 60 carbon atoms, which may in each case be the same or different, which may in each case be replaced by one or more radicals Substituted by group R 7 , wherein two or more adjacent substituents R 6 may optionally be joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, said ring system Can be substituted by one or more groups R7 ;
R 7选自氢原子、氘原子、氟原子、腈基、具有C 1～C 20的脂族烃基、具有5～30个碳原子的芳族环或杂芳族环系，其中一个或多个氢原子可被氘原子、卤素原子或腈基代替，其中任意相邻的两个或多个相邻的R 7可彼此形成单环或多环的脂族、芳族或杂芳族环系。 R 7 is selected from a hydrogen atom, a deuterium atom, a fluorine atom, a nitrile group, an aliphatic hydrocarbon group with C 1 to C 20 , an aromatic ring or a heteroaromatic ring system with 5 to 30 carbon atoms, one or more of which A hydrogen atom can be replaced by a deuterium atom, a halogen atom or a nitrile group, wherein any adjacent two or more adjacent R 7 can form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system with each other.
本发明的优选的实施方式中，所述式(I)的化合物选自式IV、V、VI、VII、VIII、IX所示化合物：In a preferred embodiment of the present invention, the compound of formula (I) is selected from the compounds shown in formula IV, V, VI, VII, VIII, IX:
Figure PCTCN2022085688-appb-000003
Figure PCTCN2022085688-appb-000003
其中使用的符号和标记具有在上文中所给出的含义。The symbols and signs used therein have the meanings given above.
本发明的优选的实施方式中，所述式IV、V、VI、VII、VIII或IX化合物中的Z、W 1、W 2、W 3或W 4特别优选代表为CH。 In a preferred embodiment of the present invention, Z, W 1 , W 2 , W 3 or W 4 in the compound of formula IV, V, VI, VII, VIII or IX is particularly preferably represented by CH.
本发明的优选的实施方式中，所述基团B、Ar 1、Ar 2、Ar 3、Ar 4或Ar 5在每次出现时相同或不同地选自由式(2)～(27)的基团组成的群组： In a preferred embodiment of the present invention, the groups B, Ar 1 , Ar 2 , Ar 3 , Ar 4 or Ar 5 are identically or differently selected from the groups of formulas (2) to (27) at each occurrence Groups composed of:
Figure PCTCN2022085688-appb-000004
Figure PCTCN2022085688-appb-000004
Figure PCTCN2022085688-appb-000005
Figure PCTCN2022085688-appb-000005
其中，虚线键指示与N连接的位置，并且使用的符号具有在上文中所给出的含义。Wherein, the dotted line key indicates the position of connection with N, and the symbols used have the meanings given above.
本发明的优选的实施方式中，所述式(2)～(27)中的基团R 1特别优选代表为氢。 In a preferred embodiment of the present invention, the group R 1 in the formulas (2) to (27) is particularly preferably represented by hydrogen.
在本发明的优选的实施方式中，所述基团Ar 1或Ar 2为式(2)、(3)、(4)、(5)或(13)的基团，并且特别是式(2)、(3)、(4)、(5)或(13)中的R 1优选为氢的基团，在Ar 1或Ar 2为这些基团的情况下，对于有机电致发光器件，实现了非常好的结果。 In a preferred embodiment of the present invention, said group Ar 1 or Ar 2 is a group of formula (2), (3), (4), (5) or (13), and in particular of formula (2 ), (3), (4), (5) or (13) in R 1 is preferably a hydrogen group, in the case of Ar 1 or Ar 2 for these groups, for organic electroluminescent devices, to achieve very good results.
在本发明的优选的实施方式中，所述基团Ar 1和Ar 2是彼此不同的。 In a preferred embodiment of the invention, said radicals Ar 1 and Ar 2 are different from each other.
如果在式(I)化合物中的基团Ar 1和Ar 2或者Ar 3和Ar 4经由基团E彼此连接，那么所述基团NAr 1Ar 2、NAr 3Ar 4优选具有式(28)、(29)、(30)、(31)或(32)之一的结构： If the groups Ar 1 and Ar 2 or Ar 3 and Ar 4 in a compound of formula (I) are connected to each other via a group E, said groups NAr 1 Ar 2 , NAr 3 Ar 4 preferably have the formula (28), The structure of one of (29), (30), (31) or (32):
Figure PCTCN2022085688-appb-000006
Figure PCTCN2022085688-appb-000006
其中使用的符号具有在上文中所给出的含义，并且虚线键指示NAr 3Ar 4通过(L) x与所述环A的键合位置，或者NAr 1Ar 2与所述环A的键合位置。 The symbols used therein have the meanings given above, and the dotted bond indicates the bonding position of NAr 3 Ar 4 to said ring A through (L) x , or the bonding of NAr 1 Ar 2 to said ring A Location.
如果所述基团L经由基团E与Ar 3连接，那么所述基团L-NAr 3Ar 4优选具有式(33)、(34)、(35)、(36)或(37)之一的结构： If the group L is attached to Ar 3 via a group E, then the group L-NAr 3 Ar 4 preferably has one of the formulas (33), (34), (35), (36) or (37) Structure:
Figure PCTCN2022085688-appb-000007
Figure PCTCN2022085688-appb-000007
其中使用的符号具有在上文中所给出的含义，并且虚线键指示与所述L与环A的键合位置。类似的情形适用于所述基团L与Ar 4的连接。 The symbols used therein have the meanings given above, and the dotted bond indicates the bonding position to said L and ring A. A similar situation applies to the attachment of the group L to Ar 4 .
本发明的另外优选的实施方式中，所述标记x＝1或2，并且所述基团In another preferred embodiment of the present invention, the label x=1 or 2, and the group
—(L) x—代表式(38)至(54)之一的基团： —(L) x —represents a group of one of formulas (38) to (54):
Figure PCTCN2022085688-appb-000008
Figure PCTCN2022085688-appb-000008
Figure PCTCN2022085688-appb-000009
Figure PCTCN2022085688-appb-000009
其中使用的符号具有在上文中所给出的含义，并且一个虚线键指示与所述环A的键合，而另一个虚线指示与B的键合。The symbols used therein have the meanings given above, and one dotted bond indicates a bond to the ring A and the other dotted bond indicates a bond to B.
在本发明的特别优选的实施方式中，所述标记x＝1或2，并且所述基团—(L) x—中的R 1特别优选代表为氢。 In a particularly preferred embodiment of the invention, the label x=1 or 2, and R 1 in the group —(L) x— is particularly preferably represented by hydrogen.
在本发明的特别优选的实施方式中，所述标记x＝0，所述基团B选自由式(2)～(27)的基团组成的群组，并且所述基团B中的R 1特别优选代表为氢。 In a particularly preferred embodiment of the present invention, the label x=0, the group B is selected from the group consisting of groups of formulas (2) to (27), and R in the group B 1 is particularly preferably represented by hydrogen.
在本发明的一个优选的实施方式中，R 1～R 5在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、Si(R 6) 3、具有C 1～C 10的直链烷基或烷氧基基团、具有C 3～C 10的支链或环状的烷基或烷氧基基团，所述基团中的每个可被一个或多个基团R 6取代，其中在每种情况下一个或多个非相邻的-CH 2-基团可被O代替，并且其中一个或多个氢原子可被氘原子或卤素原子代替，具有5至80个、优选5至60个碳原子的芳族环或杂芳蔟环系组成的组，其在每种情况下可以是相同的或不同的，其在每种情况下可以被一个或多个基团R 6取代，其中两个或更多个相邻的取代基可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系，所述环系可被一个或多个基团R 6取代。 In a preferred embodiment of the present invention, R 1 to R 5 are identically or differently selected from hydrogen atom, deuterium atom, halogen atom, nitrile group, Si(R 6 ) 3 , having C 1 to C 10 linear alkyl or alkoxy groups, C 3 to C 10 branched or cyclic alkyl or alkoxy groups, each of which may be replaced by one or more A group R 6 substituted, wherein in each case one or more non-adjacent -CH 2 - groups may be replaced by O, and wherein one or more hydrogen atoms may be replaced by deuterium atoms or halogen atoms, with 5 80, preferably 5 to 60 carbon atoms of aromatic or heteroaromatic ring systems, which may in each case be the same or different, which may in each case be replaced by one or more A group R is substituted, wherein two or more adjacent substituents may optionally be joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, said ring system may be substituted by one or more groups R 6 .
在本发明的另外优选的实施方式中，如果基团R 1与Ar 1或Ar 2键合或者R 1与Ar 3或Ar 4，则所述基团R 1在每次出现时相同或不同地选自氢原子或氘原子，具有C 1～C 10的直链烷基基团或具有C 3～C 10的支链或环状的烷基基团。 In a further preferred embodiment of the invention, if a radical R 1 is bonded to Ar 1 or Ar 2 or R 1 to Ar 3 or Ar 4 , said radical R 1 is identical or different at each occurrence It is selected from a hydrogen atom or a deuterium atom, a linear alkyl group having C 1 to C 10 or a branched or cyclic alkyl group having C 3 to C 10 .
此外，对于与碳桥连基键合的两个取代基R 2或R 1，即式(6)、(17)、(18)、(19)、(44)、(49)中的两个取代基R 2或R 1可以优选一起形成环烷基环，该环优选具有3至8个碳原子，特别优选具有5至6个碳原子。 In addition, for the two substituents R 2 or R 1 bonded to the carbon bridging group, that is, two of the formulas (6), (17), (18), (19), (44), (49) The substituents R 2 or R 1 can preferably together form a cycloalkyl ring which preferably has 3 to 8 carbon atoms, particularly preferably 5 to 6 carbon atoms.
在另外优选的实施方式中，在式(28)或(33)中与碳桥连基键合的R 1在每次出现时相同或不同地选自具有C 1～C 10的直链烷基基团或具有C 3～C 10的支链或环状的烷基基团，或者具有5至60个碳原子的芳族环或杂芳族环系，其在每种情况下可以被一个或多个基团R 2取代；除了上文给出的R 1的限定外，在此处两个基团R 1还可以彼此形成环系，该环系可以是脂族的或者是芳族的，通过成环形成螺环系。 In another preferred embodiment, R 1 bonded to the carbon bridging group in formula (28) or (33) is selected at each occurrence identically or differently from linear alkyl groups having C 1 to C 10 or a branched or cyclic alkyl group having C 3 to C 10 , or an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, which may in each case be replaced by one or a plurality of radicals R 2 are substituted; in addition to the limitations given above for R 1 , here two radicals R 1 can also form with one another a ring system, which can be aliphatic or aromatic, Spirocyclic systems are formed by ring formation.
在另外优选的实施方式中，在式(31)或(36)中与氮桥连基键合的R 1选自具有C 1～C 10的直链烷基基团、具有C 3～C 10的支链或环状的烷基基团，或者具有5至60个碳原子的芳族环或杂芳族环系，特别是具有6至24个碳原子的芳族环系，其在每种情况下可以被一个 或多个基团R 2取代。 In another preferred embodiment, in formula (31) or (36), R 1 bonded to the nitrogen bridge group is selected from linear alkyl groups with C 1 to C 10 , straight chain alkyl groups with C 3 to C 10 A branched or cyclic alkyl group, or an aromatic ring or heteroaromatic ring system having 5 to 60 carbon atoms, especially an aromatic ring system having 6 to 24 carbon atoms, which in each Cases may be substituted by one or more groups R2 .
R 2在每次出现时相同或不同地选自氢原子、氘原子，具有C 1～C 5的直链烷基、具有C 3～C 6的支链或环状的烷基、具有5至18个碳原子的芳族环或杂芳族环系。 R 2 is identically or differently selected from a hydrogen atom, a deuterium atom, a straight-chain alkyl group having C 1 to C 5 , a branched or cyclic alkyl group having C 3 to C 6 , and a group having 5 to 5 An aromatic ring or heteroaromatic ring system of 18 carbon atoms.
本发明意义上的芳基含有6～60个碳原子，在本发明意义上的杂芳基含有2～60个碳原子和至少一个杂原子，其条件是碳原子和杂原子的总和至少是5；所述杂原子优选选自N、O或S。此处的芳基或杂芳基被认为是指简单的芳族环，即苯、萘等，或简单的杂芳族环，如吡啶、嘧啶、噻吩等，或稠合的芳基或杂芳基，如蒽、菲、喹啉、异喹啉等。通过单键彼此连接的芳族环，例如联苯，相反地不被称为芳基或杂芳基，而是称为芳族环系。Aryl in the sense of the present invention contains 6 to 60 carbon atoms, heteroaryl in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5 ; the heteroatom is preferably selected from N, O or S. Here aryl or heteroaryl is taken to mean simple aromatic rings, i.e. benzene, naphthalene, etc., or simple heteroaromatic rings, such as pyridine, pyrimidine, thiophene, etc., or fused aryl or heteroaryl Groups, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic rings connected to one another via single bonds, such as biphenyl, are conversely not referred to as aryl or heteroaryl, but as aromatic ring systems.
在本发明意义上的芳族或杂芳族环系中含有5～60个碳原子，其中从苯、萘、菲、芴、螺二芴、二苯并呋喃和二苯并噻吩或这些基团的组合构建所述芳族环系。本发明意义上的芳族环系特别是还旨在被认为是指不必仅含有芳基或杂芳基的体系，而是其中多个芳基或杂芳基还可以由非芳族单元例如C、N、O或S原子连接。因此，例如，和其中两个或更多个芳基被例如短的烷基连接的体系一样，诸如芴、9,9’-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚等的体系也被认为是指在本发明意义上的芳族环系。Aromatic or heteroaromatic ring systems containing 5 to 60 carbon atoms in the sense of the present invention, wherein the radicals selected from benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene or A combination of to construct the aromatic ring system. Aromatic ring systems in the sense of the present invention are in particular also intended to be taken to mean systems which do not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups can also be formed by non-aromatic units such as C , N, O or S atom connection. Thus, for example, as are systems in which two or more aryl groups are linked by, for example, short alkyl groups such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, Systems of diaryl ethers etc. are also taken to mean aromatic ring systems in the sense of the present invention.
对于本发明意义上的含有1～40个碳原子并且其中单独的氢原子或-CH 2-基团还可被上述基团取代的脂族烃基或者烷基或者烯基或炔基优选被认为是指如下基团：甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、新戊基、环戊基、正己基、新己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。烷氧基优选具有1～40个碳原子的烷氧基被认为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。杂烷基优选具有1～40个碳原子的烷基，是指其中单独的氢原子或-CH 2-基团可被氧、硫、卤素原子取代的基团，被认为是指烷氧基、烷硫基、氟代的烷氧基、氟代的烷硫基，特别是指甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、三氟甲硫基、三氟甲氧基、五氟乙氧基、五氟乙硫基、2,2,2-三氟乙氧基、2,2,2-三氟乙硫基、乙烯氧基、乙烯硫基、丙烯氧基、丙烯硫基、丁烯硫基、丁烯氧基、戊烯氧基、戊烯硫基、环戊烯氧基、环戊烯硫基、己烯氧基、己烯硫基、环己烯氧基、环己烯硫基、乙炔氧基、乙炔硫基、丙炔氧基、丙炔硫基、丁炔氧基、丁炔硫基、戊炔氧基、戊炔硫基、己炔氧基、己炔硫基。 Aliphatic hydrocarbon radicals or alkyl or alkenyl or alkynyl radicals containing 1 to 40 carbon atoms in the sense of the present invention and in which individual hydrogen atoms or -CH2- radicals may also be substituted by the aforementioned radicals are preferably considered to be Refers to the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, Neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptyl Alkenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. Alkoxy preferably having 1 to 40 carbon atoms is considered methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy radical, sec-butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n- Octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy. Heteroalkyl is preferably an alkyl group having 1 to 40 carbon atoms, and refers to a group in which individual hydrogen atoms or -CH2- groups may be replaced by oxygen, sulfur, halogen atoms, and is considered to mean alkoxy, Alkylthio, fluorinated alkoxy, fluorinated alkylthio, especially methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butyl Oxygen, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio group, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethoxy, 2,2,2-trifluoroethylthio, vinyloxy, vinylthio group, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio Cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio group, hexynyloxy, hexynylthio.
一般来说，根据本发明的环烷基、环烯基可为环丙基、环丁基、环戊基、环己基、环丁烯基、环戊烯基、环己烯基、环庚基、环庚烯基，其中一个或多个-CH 2-基团可被上述基团代替；此外，一个或多个氢原子还可被氘原子、卤素原子或腈基代替。 In general, cycloalkyl, cycloalkenyl according to the present invention can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl , cycloheptenyl, wherein one or more -CH 2 - groups can be replaced by the above groups; in addition, one or more hydrogen atoms can also be replaced by deuterium atoms, halogen atoms or nitrile groups.
根据本发明的芳族或杂芳族环原子，在每种情况下还可被上述基团R 1取代的芳族或杂芳族环系，特别是指衍生自如下物质的基团：苯、萘、蒽、苯并蒽、菲、芘、
Figure PCTCN2022085688-appb-000010
苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、顺式或反式茚并咔唑、顺式或反式吲哚并咔唑、三 聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并[5,6]喹啉、苯并[6,7]喹啉、苯并[7,8]喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、六氮杂苯并菲、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘，4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯并噻二唑或者衍生自这些体系的组合的基团。 Aromatic or heteroaromatic ring atoms according to the invention, aromatic or heteroaromatic ring systems which may in each case also be substituted by the abovementioned radicals R, in particular mean radicals derived from benzene, Naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,
Figure PCTCN2022085688-appb-000010
Perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenyl, terphenyl, tripolyphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis Or trans indenofluorene, cis or trans indenocarbazole, cis or trans indolocarbazole, tripolyindene, isotripolyindene, spirothree polyindene, spiroisotripolyindene, furan, Benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline , acridine, phenanthridine, benzo[5,6]quinoline, benzo[6,7]quinoline, benzo[7,8]quinoline, phenothiazine, phenoxazine, pyrazole, indazole , imidazole, benzimidazole, naphthimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthoxazole, anthraxazole, phenanthrene Oxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazapyrene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene Pyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorochrome, naphthyridine, azacarbazole, benzocarboline, carboline, phenanthrene oxadiazole, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2, 5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3, 4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2 , 3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole or groups derived from combinations of these systems.
根据本发明的化合物的实施例主要包括在下表中显示的化合物：Examples of compounds according to the invention mainly include the compounds shown in the table below:
Figure PCTCN2022085688-appb-000011
Figure PCTCN2022085688-appb-000011
Figure PCTCN2022085688-appb-000012
Figure PCTCN2022085688-appb-000012
Figure PCTCN2022085688-appb-000013
Figure PCTCN2022085688-appb-000013
Figure PCTCN2022085688-appb-000014
Figure PCTCN2022085688-appb-000014
Figure PCTCN2022085688-appb-000015
Figure PCTCN2022085688-appb-000015
Figure PCTCN2022085688-appb-000016
Figure PCTCN2022085688-appb-000016
Figure PCTCN2022085688-appb-000017
Figure PCTCN2022085688-appb-000017
Figure PCTCN2022085688-appb-000018
Figure PCTCN2022085688-appb-000018
Figure PCTCN2022085688-appb-000019
Figure PCTCN2022085688-appb-000019
Figure PCTCN2022085688-appb-000020
Figure PCTCN2022085688-appb-000020
本发明的另一方面为一种有机电致发光元件用材料，其包含本发明的化合物。Another aspect of the present invention is a material for an organic electroluminescence device, which comprises the compound of the present invention.
本发明的又一方面为一种有机电致发光元件/装置，所述有机电致发光元件包含阴极、阳极和至少一个发光层。除了这些层之外，它还可以包含其它的层，例如在每种情况下，包含一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、激子阻挡层、电子阻挡层和/或电荷产生层。具有例如激子阻挡功能的中间层同样可引入两个发光层之间。然而，应当指出，这些层中的每个并非必须都存在。此处所述有机电致发光装置可包含一个发光层，或者它可包含多个发光层。即，将能够发光的多种发光化合物用于所述发光层中。特别优选具有三个发光层的体系，其中所述三个层可显示蓝色、绿色和红色发光。如果存在多于一个的发光层，则根据本发明，这些层中的至少一个层包含本发明的化合物。Yet another aspect of the present invention is an organic electroluminescent element/device comprising a cathode, an anode and at least one light emitting layer. Besides these layers it may also contain further layers, for example in each case one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, excitation layers, sub-blocking layer, electron blocking layer and/or charge generating layer. Interlayers having, for example, an exciton-blocking function can likewise be introduced between two emitting layers. It should be noted, however, that not every one of these layers is required to be present. The organic electroluminescent device described herein may comprise one light-emitting layer, or it may comprise a plurality of light-emitting layers. That is, various light-emitting compounds capable of emitting light are used in the light-emitting layer. Particular preference is given to systems with three emitting layers, the three layers being able to exhibit blue, green and red emission. If more than one emitting layer is present, according to the invention at least one of these layers comprises a compound according to the invention.
在本发明的另外的实施方式中，式(I)的化合物或优选的实施方式既可用于空穴传输层中或激子阻挡层中，又可用作发光层中的基质。In a further embodiment of the invention, the compounds of the formula (I) or preferred embodiments can be used both in the hole-transport layer or in the exciton-blocking layer and as matrix in the emitting layer.
在根据本发明的有机电致发光元件的其它层中，特别是在空穴注入和空穴传输层中以及在电子注入和电子传输层中，所有材料可以按照根据现有技术通常所使用的方式来使用。本领域普通技术人员因此将能够在不付出创造性劳动的情况下与根据本发明的发光层组合使用关于有机电致发光元件所知的所有材料。In the other layers of the organic electroluminescent component according to the invention, in particular in the hole-injection and hole-transport layer and in the electron-injection and electron-transport layer, all materials can be used in the manner usually used according to the prior art to use. A person skilled in the art will therefore be able to use, without inventive step, all materials known for organic electroluminescent elements in combination with the emitting layer according to the invention.
此外优选如下的有机电致发光元件，借助于升华方法施加一个或多个层，其中在真空升华装置中在低于10 -5Pa、优选低于10 -6Pa的初压下通过气相沉积来施加所述材料。然而，所述初压还可能甚至更低，例如低于10 -7Pa。 Furthermore, preference is given to organic electroluminescent components in which one or more layers are applied by means of a sublimation method by vapor deposition in a vacuum sublimation apparatus at an initial pressure below 10 −5 Pa, preferably below 10 −6 Pa. Apply the material. However, the initial pressure may also be even lower, for example below 10 −7 Pa.
同样优选如下的有机电致发光元件，借助于有机气相沉积方法或借助于载气升华来施加一个或多个层，其中，在10 -5Pa至1Pa之间的压力下施加所述材料。该方法的特别的例子是有机蒸气喷印方法，其中所述材料通过喷嘴直接施加，并且因此是结构化的。 Preference is likewise given to organic electroluminescent components in which one or more layers are applied by means of organic vapor deposition methods or by means of carrier gas sublimation, the materials being applied at a pressure of between 10 −5 Pa and 1 Pa. A particular example of this method is the organic vapor jet printing method, in which the material is applied directly via a nozzle and is thus structured.
此外优选如下的有机电致发光元件，从溶液中，例如通过旋涂，或借助于任何所希望的印刷方法例如丝网印刷、柔性版印刷、平版印刷、光引发热成像、热转印、喷墨印刷或喷嘴印刷，来产生一个或多个层。可溶性化合物，例如通过适当的取代修饰本发明式(I)所示的化合物获得可溶性化合物。这些方法也特别适于低聚物、树枝状大分子和聚合物。此外可行的是混合方法，其中例如从溶液中施加一个或多个层并且通过气相沉积施加一个或多个另外的层。Furthermore, preference is given to organic electroluminescent elements which, from solution, for example by spin coating, or by means of any desired printing method, such as screen printing, flexographic printing, lithography, photoinduced thermography, thermal transfer, spray Ink printing or nozzle printing to produce one or more layers. Soluble compound, for example, the soluble compound can be obtained by modifying the compound represented by the formula (I) of the present invention by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Also possible are hybrid methods in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
在本发明的另一个实施方式中，根据本发明的有机电致发光元件不包含单独的空穴注入层和/或空穴传输层和/或空穴阻挡层和/或电子传输层，即发光层与空穴注入层或阳极直 接相邻，和/或发光层与电子传输层或电子注入层或阴极直接相邻。In a further embodiment of the invention, the organic electroluminescent component according to the invention does not comprise a separate hole-injection layer and/or hole-transport layer and/or hole-blocking layer and/or electron-transport layer, i.e. emits light A layer is directly adjacent to a hole injection layer or an anode, and/or an emissive layer is directly adjacent to an electron transport layer or an electron injection layer or a cathode.
这些方法是本领域普通技术人员通常已知的，并且他们可以在不付出创造性劳动的情况下将其应用于包含根据本发明的化合物的有机电致发光元件。These methods are generally known to those skilled in the art and they can apply them without inventive effort to organic electroluminescent components comprising the compounds according to the invention.
因此，本发明还涉及制造根据本发明的有机电致发光元件的方法，可借助于升华方法来施加至少一个层，和/或借助于有机气相沉积方法或借助于载气升华来施加至少一个层，和/或从溶液中通过旋涂或借助于印刷方法来施加至少一个层。The invention therefore also relates to a method for producing an organic electroluminescent element according to the invention, at least one layer being applied by means of a sublimation method and/or at least one layer being applied by means of an organic vapor deposition method or by means of sublimation of a carrier gas , and/or apply at least one layer from solution by spin coating or by means of a printing method.
此外，本发明涉及包含至少一种上文指出的化合物。如上文关于有机电致发光元件指出的相同优选情况适用于所述本发明的化合物。特别是，所述化合物此外还可优选包含其它化合物。从液相处理根据本发明的化合物，例如通过旋涂或通过印刷方法进行处理，需要根据本发明的化合物的制剂。这些制剂可以例如是溶液、分散体或乳液。出于这个目的，可优选使用两种或更多种溶剂的混合物。合适并且优选的溶剂例如是甲苯、苯甲醚、邻二甲苯、间二甲苯或对二甲苯、苯甲酸甲酯、均三甲苯、萘满、邻二甲氧基苯、四氢呋喃、甲基四氢呋喃、四氢吡喃、氯苯、二噁烷、苯氧基甲苯，特别是3-苯氧基甲苯、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯烷酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、异丙苯、环己醇、环己酮、环己基苯、十氢化萘、十二烷基苯、苯甲酸乙酯、茚满、苯甲酸甲酯、1-甲基吡咯烷酮、对甲基异丙基苯、苯乙醚、1,4-二异丙基苯、二苄醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二甲基醚、二乙二醇单丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-异丙基萘、戊苯、己苯、庚苯、辛苯、1,1-双(3,4-二甲基苯基)乙烷，或这些溶剂的混合物。Furthermore, the present invention relates to compounds comprising at least one of the above indicated compounds. The same preferences as indicated above for organic electroluminescent elements apply to the compounds according to the invention. In particular, the compounds can preferably also comprise further compounds. The processing of the compounds according to the invention from the liquid phase, for example by spin coating or by printing methods, requires the formulation of the compounds according to the invention. These formulations may, for example, be solutions, dispersions or emulsions. For this purpose, mixtures of two or more solvents may preferably be used. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, Tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenzone, 1,2,3,5-tetramethylbenzene, 1,2, 4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-Dimethylanisole, 3,5-Dimethylanisole, Acetophenone, α-Terpineol, Benzothiazole, Butyl Benzoate, Cumene, Cyclohexanol, Cyclohexanol Hexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1,4 -Diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol mono Butyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-di methylphenyl)ethane, or a mixture of these solvents.
这些方法通常为本领域的技术人员所知，并且可由他在没有付出创造性劳动的情况下应用到包含本发明化合物的有机电致发光元件中。These methods are generally known to the person skilled in the art and can be applied by him without inventive effort to organic electroluminescent components comprising the compounds according to the invention.
本发明的有机电致发光元件既可以是顶发射光元件，又可以是底发射光元件。本发明的有机电致发光元件的结构和制备方法没有限定。采用本发明的化合物制得的有机电致发光元件可降低启动电压、提高发光效率和亮度。The organic electroluminescent element of the present invention can be either a top-emitting light element or a bottom-emitting light element. The structure and preparation method of the organic electroluminescent element of the present invention are not limited. The organic electroluminescent element prepared by using the compound of the invention can reduce the starting voltage and improve the luminous efficiency and brightness.
本发明的再一方面为一种电子设备，其具备本发明的有机电致发光元件。Still another aspect of the present invention is an electronic device including the organic electroluminescent element of the present invention.
所述电子设备能够用于多种应用，例如用于单色或多色显示器，用于照明应用或用于医疗和/或美容应用，例如用于光线疗法中。The electronic device can be used in various applications, for example for monochrome or multicolor displays, for lighting applications or for medical and/or cosmetic applications, for example in phototherapy.
根据本发明的化合物和根据本发明的有机电致发光元件具有如下优于现有技术的令人惊讶的优点：The compounds according to the invention and the organic electroluminescent elements according to the invention have the following surprising advantages over the prior art:
1.根据本发明的化合物非常适合用于有机电致发光元件中的空穴传输或空穴注入层中。它们特别是还适合用于与磷光发光层直接相邻的层中，因为根据本发明的化合物并不湮灭发光。1. The compounds according to the invention are very suitable for use in hole-transport or hole-injection layers in organic electroluminescent components. They are also suitable in particular for use in layers directly adjacent to the phosphorescent emitting layer, since the compounds according to the invention do not annihilate the emission.
2.当用作荧光或磷光发光体的基质材料时，根据本发明的化合物导致非常高的效率和长寿命，如果所述化合物与其它基质材料和磷光发光体一起用作基质材料则特别适用这 点。2. When used as matrix material for fluorescent or phosphorescent emitters, the compounds according to the invention lead to very high efficiencies and long lifetimes, which is especially suitable if the compounds are used as matrix materials together with other matrix materials and phosphorescent emitters point.
3.当用于有机电致发光元件中时，根据本发明的化合物导致高效率，并且在使用和低工作电压的情况下导致陡峭的电流-电压曲线。3. When used in organic electroluminescent elements, the compounds according to the invention lead to high efficiencies and, in the case of use and low operating voltages, to steep current-voltage curves.
4.根据本发明的化合物具有高的热稳定性，并且能够在不分解和没有残余物的情况下进行升华。4. The compounds according to the invention have high thermal stability and are capable of sublimation without decomposition and without residues.
5.根据本发明的化合物具有高的氧化稳定性，这对于这些化合物的处理和对于溶液的贮存稳定性特别具有积极的效果。5. The compounds according to the invention have a high oxidation stability, which has particularly positive effects on the handling of these compounds and on the storage stability of solutions.
上述这些优点并不伴有对其它电子性质的损害。These above-mentioned advantages are not accompanied by impairment of other electronic properties.
附图说明Description of drawings
图1中示出本发明的有机电致发光装置的一个底部发光例子的示意图。FIG. 1 shows a schematic diagram of an example of bottom emission of the organic electroluminescent device of the present invention.
图2中示出本发明的有机电致发光装置的一个顶部发光例子的示意图。FIG. 2 shows a schematic diagram of an example of top emission of the organic electroluminescent device of the present invention.
其中，1-基板、2-阳极、3-空穴注入层、4-空穴传输/电子阻挡层、5-发光层、6-空穴阻挡/电子传输层、7-电子注入层、8-阴极。Among them, 1-substrate, 2-anode, 3-hole injection layer, 4-hole transport/electron blocking layer, 5-light-emitting layer, 6-hole blocking/electron transport layer, 7-electron injection layer, 8- cathode.
具体实施方式Detailed ways
通过如下实施例更详细地解释本发明，但并不希望由此限制本发明。在所述描述的基础上，本领域普通技术人员将能够在没有付出创造性劳动的情况下所公开整个范围内实施本发明并且制备根据本发明的其它化合物，并且将它们用于电子元件中或使用根据本发明的方法。The invention is explained in more detail by the following examples, without wishing to limit the invention thereby. On the basis of the description, a person skilled in the art will be able, without inventive effort, to carry out the invention within the entire scope disclosed and to prepare other compounds according to the invention and to use them in electronic components or use according to the method of the invention.
实施例Example
以下，对本发明的实施例进行说明，但本发明并不限于这些实施例。Hereinafter, examples of the present invention will be described, but the present invention is not limited to these examples.
另外，如无特殊说明，本发明中所用原料均可通过市售商购获得，本发明所记载的任何范围包括端值以及端值之间的任何数值以及端值或者端值之间的任意数值所构成的任意子范围。In addition, unless otherwise specified, the raw materials used in the present invention can be obtained commercially, and any range described in the present invention includes the end value and any value between the end value and the end value or any value between the end value Any subrange formed by .
为了更清楚地说明本发明，下面结合优选实施例和附图对本发明做进一步的说明。附图中相似的部件以相同的附图标记进行表示。本领域技术人员应当理解，下面所具体描述的内容是说明性的而非限制性的，不应以此限制本发明的保护范围。In order to illustrate the present invention more clearly, the present invention will be further described below in conjunction with preferred embodiments and accompanying drawings. Similar parts in the figures are denoted by the same reference numerals. Those skilled in the art should understand that the content specifically described below is illustrative rather than restrictive, and should not limit the protection scope of the present invention.
在本发明的描述中，除非另有说明，“多个”的含义是两个或两个以上；术语“上”、“下”等指示的方位或位置关系为基于附图所示的方位或位置关系，仅是为了便于描述本发明和简化描述，而不是指示或暗示所指的装置或元件必须具有特定的方位、以特定的方位构造和操作，因此不能理解为对本发明的限制。In the description of the present invention, unless otherwise specified, the meaning of "plurality" is two or more; the orientation or positional relationship indicated by the terms "upper", "lower" and so on is based on the orientation or position shown in the drawings. The positional relationship is only for the convenience of describing the present invention and simplifying the description, but does not indicate or imply that the referred device or element must have a specific orientation, be constructed and operated in a specific orientation, and thus should not be construed as limiting the present invention.
本发明中，制备方法如无特殊说明则均为常规方法。所用的原料如无特别说明均可从公开的商业途径获得，所述百分比如无特殊说明，均为质量百分比。In the present invention, the preparation methods are conventional methods unless otherwise specified. The raw materials used can be obtained from public commercial sources unless otherwise specified, and the stated percentages are all mass percentages unless otherwise specified.
下述实施例对OLED材料及元件进行性能测试的测试仪器及方法如下：The testing apparatus and method that following embodiment carries out performance test to OLED material and element are as follows:
OLED元件性能检测条件：OLED component performance testing conditions:
亮度和色度坐标：使用光谱扫描仪PhotoResearch PR-715测试；Luminance and chromaticity coordinates: tested using spectral scanner PhotoResearch PR-715;
电流密度和起亮电压：使用数字源表Keithley 2420测试；Current density and lighting voltage: Tested with Keithley 2420 digital source meter;
功率效率：使用NEWPORT 1931-C测试；Power efficiency: tested with NEWPORT 1931-C;
寿命测试：使用LTS-1004AC寿命测试装置。Life test: use LTS-1004AC life test device.
实施例Example
化合物CJHL461～CJHL586的制备方法，包括如下步骤：The preparation method of compound CJHL461～CJHL586 comprises the following steps:
第一步：化合物Int-1的制备The first step: preparation of compound Int-1
Figure PCTCN2022085688-appb-000021
Figure PCTCN2022085688-appb-000021
50.0mmol的4-溴二苯并[b,d]呋喃(CAS:89827-45-2)、50.0mmol的对氯苯胺、60.0mmol的叔丁醇钠和80.0mL的甲苯混合，再加入52mg(0.05mmol)的Pd 2(dba) 3CHCl 3催化剂、0.05mL的10％三叔丁基磷甲苯溶液，在氮气保护下，升温至100℃搅拌反应12小时，冷却到室温，加入60mL的水稀释，用乙酸乙酯萃取，有机相干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到化合物Int-1，黄色固体，收率78％。 50.0mmol of 4-bromodibenzo[b,d]furan (CAS: 89827-45-2), 50.0mmol of p-chloroaniline, 60.0mmol of sodium tert-butoxide and 80.0mL of toluene were mixed, and then 52mg ( 0.05mmol) of Pd 2 (dba) 3 CHCl 3 catalyst, 0.05mL of 10% tri-tert-butylphosphorus toluene solution, under nitrogen protection, heat up to 100°C and stir for 12 hours, cool to room temperature, add 60mL of water to dilute , extracted with ethyl acetate, the organic phase was dried, filtered, the filtrate was concentrated to dryness under reduced pressure, separated and purified by silica gel column to obtain compound Int-1, a yellow solid, with a yield of 78%.
第二步：化合物Int-2的制备The second step: the preparation of compound Int-2
Figure PCTCN2022085688-appb-000022
Figure PCTCN2022085688-appb-000022
40.0mmol的化合物Int-1溶解于100mL的二氯甲烷，加入80.0mmol的吡啶，在氮气保护下，降温至0℃，滴加入44.0mmol的1-金钢烷甲酰氯，搅拌反应1小时，升到室温反应1小时，加入20mL的1N稀盐酸水溶液，收集有机相干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到化合物Int-2，收率95％。40.0mmol of compound Int-1 was dissolved in 100mL of dichloromethane, 80.0mmol of pyridine was added, under the protection of nitrogen, the temperature was lowered to 0°C, 44.0mmol of 1-adamantanecarbonyl chloride was added dropwise, and the reaction was stirred for 1 hour. After reacting at room temperature for 1 hour, 20 mL of 1N dilute hydrochloric acid aqueous solution was added, the organic phase was collected and dried, filtered, and the filtrate was concentrated to dryness under reduced pressure, separated and purified by silica gel column to obtain compound Int-2 with a yield of 95%.
第三步：化合物A1的制备The third step: preparation of compound A1
Figure PCTCN2022085688-appb-000023
Figure PCTCN2022085688-appb-000023
40.0mmol的化合物Int-2溶于80mL干燥的二氯甲烷中，在氮气保护下，滴加入88.0mmol三溴化硼溶于二氯甲烷的溶液，搅拌反应2小时，加入88.0mmol的频那醇和0.2mol的三乙胺，搅拌反应2小时，加入20mL的饱和氯化铵水溶液，用二氯甲烷萃取，收集有 机相，干燥，减压浓缩干，用硅胶柱分离纯化，得到白色固体，收率72％。40.0mmol of compound Int-2 was dissolved in 80mL of dry dichloromethane, under nitrogen protection, a solution of 88.0mmol boron tribromide dissolved in dichloromethane was added dropwise, stirred for 2 hours, and 88.0mmol of pinacol and 0.2mol of triethylamine, stirred and reacted for 2 hours, added 20mL of saturated ammonium chloride aqueous solution, extracted with dichloromethane, collected the organic phase, dried, concentrated under reduced pressure to dryness, separated and purified with a silica gel column to obtain a white solid, the yield 72%.
以上述类似的合成方法，制备以下化合物：With above-mentioned similar synthesis method, prepare following compound:
Figure PCTCN2022085688-appb-000024
Figure PCTCN2022085688-appb-000024
Figure PCTCN2022085688-appb-000025
Figure PCTCN2022085688-appb-000025
Figure PCTCN2022085688-appb-000026
Figure PCTCN2022085688-appb-000026
Figure PCTCN2022085688-appb-000027
Figure PCTCN2022085688-appb-000027
Figure PCTCN2022085688-appb-000028
Figure PCTCN2022085688-appb-000028
Figure PCTCN2022085688-appb-000029
Figure PCTCN2022085688-appb-000029
第四步：化合物B476的制备The fourth step: the preparation of compound B476
Figure PCTCN2022085688-appb-000030
Figure PCTCN2022085688-appb-000030
24.0mmol的A1溶解于60mL的甲苯、30mL的乙醇和30mL的水中，在氮气保护下，加入20.0mmol的N-(4-溴苯基)-9,9-二甲基-N-苯基-9H-芴-2-胺(CAS:885684-43-5)和277.0mg的Pd(PPh 3) 4催化剂，再加入80.0mmol的无水碳酸钠，升温回流搅拌反应10小时，冷却到室温，滴加入50mL饱和的氯化钠水溶液，用乙酸乙酯萃取，收集有机相干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到化合物B476，收率85％。 24.0mmol of A1 was dissolved in 60mL of toluene, 30mL of ethanol and 30mL of water, and under nitrogen protection, 20.0mmol of N-(4-bromophenyl)-9,9-dimethyl-N-phenyl- 9H-Fluoren-2-amine (CAS: 885684-43-5) and 277.0 mg of Pd(PPh 3 ) 4 catalyst, then added 80.0 mmol of anhydrous sodium carbonate, heated and refluxed and stirred for 10 hours, cooled to room temperature, dropwise Add 50 mL of saturated sodium chloride aqueous solution, extract with ethyl acetate, collect the organic phase and dry it, filter it, concentrate the filtrate to dryness under reduced pressure, and separate and purify it with a silica gel column to obtain compound B476 with a yield of 85%.
第五步：化合物Int-3的制备Step 5: Preparation of compound Int-3
Figure PCTCN2022085688-appb-000031
Figure PCTCN2022085688-appb-000031
24.0mmol的苯硼酸(CAS:98-80-6)溶解于80mL的THF和20mL的水中，在氮气保护下，加入20.0mmol的B476和35.5mg的Pd132催化剂，再加入0.1mol的氢氧化钠，升温回流搅拌反应10小时，冷却到室温，加入100mL饱和的氯化钠水溶液，过滤，滤饼用水洗、乙醇洗，用硅胶柱分离纯化，得到化合物Int-3，收率78％。24.0mmol of phenylboronic acid (CAS: 98-80-6) was dissolved in 80mL of THF and 20mL of water, under nitrogen protection, 20.0mmol of B476 and 35.5mg of Pd132 catalyst were added, then 0.1mol of sodium hydroxide was added, Raise the temperature to reflux and stir for 10 hours, cool to room temperature, add 100mL saturated aqueous sodium chloride solution, filter, wash the filter cake with water and ethanol, and separate and purify with a silica gel column to obtain compound Int-3 with a yield of 78%.
第六步：化合物CJHL476的制备Step 6: Preparation of Compound CJHL476
Figure PCTCN2022085688-appb-000032
Figure PCTCN2022085688-appb-000032
26.0mmol的Int-3溶解于100mL的甲苯中，在氮气保护下，加入31.2mmol的碘苯(CAS:591-50-4)和39.0mmol的叔丁醇钠，再加入0.02mmol的Pd 2(dba) 3催化剂、0.04mmol的Xphos，升温至100℃搅拌反应12小时，冷却到室温，加入60mL的水稀释，过滤，滤饼用水洗、乙醇洗，用硅胶柱分离纯化，得到化合物CJHL476，黄色固体，收率88％，HRMS：771.3391[M+H] +。 26.0 mmol of Int-3 was dissolved in 100 mL of toluene, under nitrogen protection, 31.2 mmol of iodobenzene (CAS: 591-50-4) and 39.0 mmol of sodium tert-butoxide were added, and then 0.02 mmol of Pd 2 ( dba) 3 catalyst, 0.04mmol of Xphos, heat up to 100°C and stir for 12 hours, cool to room temperature, add 60mL of water to dilute, filter, wash the filter cake with water and ethanol, separate and purify with silica gel column to obtain compound CJHL476, yellow Solid, yield 88%, HRMS: 771.3391 [M+H] + .
参照上述第四步至第六步的合成方法，制备以下化合物：With reference to the synthetic method of the above-mentioned fourth step to the sixth step, the following compounds are prepared:
Figure PCTCN2022085688-appb-000033
Figure PCTCN2022085688-appb-000033
Figure PCTCN2022085688-appb-000034
Figure PCTCN2022085688-appb-000034
Figure PCTCN2022085688-appb-000035
Figure PCTCN2022085688-appb-000035
Figure PCTCN2022085688-appb-000036
Figure PCTCN2022085688-appb-000036
Figure PCTCN2022085688-appb-000037
Figure PCTCN2022085688-appb-000037
本发明提供的OLED元件如图1和图2所示，该有机电致发光装置具有基板1、阳极2、阴极8，以及配置于阳极2与阴极8之间的层3～7。其中，在阴极8与发光层5之间配置有空穴阻挡/电子传输层6和电子注入层7，在发光层5与阳极2之间配置有空穴注入层3和空穴传输/电子阻挡层4。The OLED element provided by the present invention is shown in FIG. 1 and FIG. 2 . The organic electroluminescent device has a substrate 1 , an anode 2 , a cathode 8 , and layers 3 to 7 arranged between the anode 2 and the cathode 8 . Among them, a hole blocking/electron transport layer 6 and an electron injection layer 7 are arranged between the cathode 8 and the light emitting layer 5, and a hole injection layer 3 and a hole transport/electron blocking layer are arranged between the light emitting layer 5 and the anode 2. Layer 4.
有机电致发光元件的对比例Comparative example of organic electroluminescence element
使用下述的式C作为空穴注入层材料、式F4作为p型掺杂材料、式D作为空穴传输层材料、式H作为电子阻挡层材料、式A作为发光层的主体材料，使用下述的式B作为发光层的掺杂材料、式G作为n型掺杂材料、LiQ作为电子传输层的主体材料，如下所述的制备有机电致发光元件。Use the following formula C as the hole injection layer material, formula F4 as the p-type dopant material, formula D as the hole transport layer material, formula H as the electron blocking layer material, and formula A as the host material of the light-emitting layer, using the following Formula B is used as the doping material of the light-emitting layer, formula G is used as the n-type doping material, and LiQ is used as the host material of the electron transport layer, and the organic electroluminescent element is prepared as follows.
Figure PCTCN2022085688-appb-000038
Figure PCTCN2022085688-appb-000038
将化合物C+F4(3％)
Figure PCTCN2022085688-appb-000039
Figure PCTCN2022085688-appb-000040
依次采用DOV公司制造的EL蒸镀机蒸镀到ITO玻璃上制作发光元件，制得对比例的有机电致发光元件。 Compound C+F4 (3%)
Figure PCTCN2022085688-appb-000039
Figure PCTCN2022085688-appb-000040
The EL vapor deposition machine manufactured by DOV Company was used to vapor-deposit on the ITO glass to make light-emitting elements in turn, and the organic electroluminescent element of the comparative example was obtained.
有机电致发光元件的实施例Examples of organic electroluminescent elements
在前述的有机电致发光元件的对比例中，将前述的化合物C替换为本发明的化合物，除此之外，采用同样的方法制作有机电致发光元件：ITO/本发明的化合物+F4(3％)
Figure PCTCN2022085688-appb-000041
Figure PCTCN2022085688-appb-000042
In the comparative example of the aforementioned organic electroluminescent element, the aforementioned compound C is replaced by the compound of the present invention, except that, the same method is used to make the organic electroluminescent element: ITO/compound of the present invention+F4( 3%)
Figure PCTCN2022085688-appb-000041
Figure PCTCN2022085688-appb-000042
所得元件的性能检测结果列于表1中，其中驱动电压、外量子效率EQE、电流效率LE和寿命T80％的数据是相对于对比例数据的归一化。The performance test results of the obtained components are listed in Table 1, wherein the data of driving voltage, external quantum efficiency EQE, current efficiency LE and lifetime T80% are normalized relative to the data of the comparative example.
表1元件性能检测结果Table 1 Component performance test results
Figure PCTCN2022085688-appb-000043
Figure PCTCN2022085688-appb-000043
Figure PCTCN2022085688-appb-000044
Figure PCTCN2022085688-appb-000044
Figure PCTCN2022085688-appb-000045
Figure PCTCN2022085688-appb-000045
Figure PCTCN2022085688-appb-000046
Figure PCTCN2022085688-appb-000046
由上可知，本发明的有机材料制备的元件驱动电压低，外量子效率较高，色纯度较好，而且在元件发光亮度初始为1000尼特为基准的条件下，使用本发明的化合物作为空穴注入层材料的元件寿命要好很多。It can be known from the above that the drive voltage of the element prepared by the organic material of the present invention is low, the external quantum efficiency is high, and the color purity is good, and under the condition that the luminous brightness of the element is initially 1000 nits as the benchmark, the compound of the present invention is used as an empty space. The device life of the hole injection layer material is much better.
在前述的有机电致发光元件的对比例中，将前述的化合物H替换为本发明的化合物，除此之外，采用同样的方法制作有机电致发光元件：ITO/C+F4(3％)
Figure PCTCN2022085688-appb-000047
本 发明的化合物
Figure PCTCN2022085688-appb-000048
In the comparative example of the aforementioned organic electroluminescent element, the aforementioned compound H is replaced by the compound of the present invention, except that, the same method is used to make the organic electroluminescent element: ITO/C+F4 (3%)
Figure PCTCN2022085688-appb-000047
Compounds of the invention
Figure PCTCN2022085688-appb-000048
所得元件的性能检测结果列于表2中。The performance test results of the obtained components are listed in Table 2.
表2元件性能检测结果Table 2 Component performance test results
Figure PCTCN2022085688-appb-000049
Figure PCTCN2022085688-appb-000049
Figure PCTCN2022085688-appb-000050
Figure PCTCN2022085688-appb-000050
Figure PCTCN2022085688-appb-000051
Figure PCTCN2022085688-appb-000051
Figure PCTCN2022085688-appb-000052
Figure PCTCN2022085688-appb-000052
由上可知，本发明的有机材料制备的元件驱动电压低，外量子效率较高，色纯度较好，而且在元件发光亮度初始为1000尼特为基准的条件下，使用本发明的化合物作为电子阻挡层材料的元件寿命要好很多。It can be seen from the above that the drive voltage of the element prepared by the organic material of the present invention is low, the external quantum efficiency is high, and the color purity is good, and under the condition that the luminous brightness of the element is initially 1000 nits as the benchmark, the compound of the present invention is used as the electronic component. The component life of the barrier material is much better.
在前述的有机电致发光元件的对比例中，将前述的化合物D替换为本发明的化合物，除此之外，采用同样的方法制作有机电致发光元件：ITO/C+F4(3％)
Figure PCTCN2022085688-appb-000053
本发明的化合物
Figure PCTCN2022085688-appb-000054
所得元件的性能检测结果列于表3中。 In the comparative example of the aforementioned organic electroluminescent element, the aforementioned compound D is replaced by the compound of the present invention, except that, the same method is used to make the organic electroluminescent element: ITO/C+F4 (3%)
Figure PCTCN2022085688-appb-000053
Compounds of the invention
Figure PCTCN2022085688-appb-000054
The performance test results of the obtained components are listed in Table 3.
表3元件性能检测结果Table 3 Component performance test results
Figure PCTCN2022085688-appb-000055
Figure PCTCN2022085688-appb-000055
Figure PCTCN2022085688-appb-000056
Figure PCTCN2022085688-appb-000056
Figure PCTCN2022085688-appb-000057
Figure PCTCN2022085688-appb-000057
Figure PCTCN2022085688-appb-000058
Figure PCTCN2022085688-appb-000058
由表3的元件性能测试结果可知，本发明的有机材料制备成的元件驱动电压明显降低，外量子效率提高，发光色纯度较好，而且在元件发光初始亮度为1000尼特为基准的条件下，使用本发明的化合物作为空穴传输层材料的元件寿命衰减要慢很多。It can be seen from the test results of the element performance in Table 3 that the driving voltage of the element prepared by the organic material of the present invention is significantly reduced, the external quantum efficiency is improved, and the purity of the luminous color is better, and under the condition that the initial luminance of the element is 1000 nits as the benchmark , the decay of the lifetime of the device using the compound of the present invention as the material of the hole transport layer is much slower.
显然，本发明的应用不限于上述实施例的举例，对于所属领域的普通技术人员来说，在上述说明的基础上还可以做出其它不同形式的变化或变动，这里无法对所有的实施方式予以穷举，凡是属于本发明的技术方案所引伸出的显而易见的变化或变动仍处于本发明所属权利要求的保护范围之列。Obviously, the application of the present invention is not limited to the examples of the above-mentioned embodiments. For those of ordinary skill in the art, on the basis of the above-mentioned descriptions, other changes or changes in different forms can also be made. Exhaustively, all the obvious changes or changes derived from the technical solutions of the present invention are still within the protection scope of the claims of the present invention.

Claims (10)

  1. 一种化合物，其结构式如式(I)所示，A kind of compound, its structural formula is shown in formula (I),
    Figure PCTCN2022085688-appb-100001
    Figure PCTCN2022085688-appb-100001
    其中，L在每次出现时相同或不同地为芳族环系，其中的每个L可以被一个或多个基团R 1取代； wherein each occurrence of L is, identically or differently, an aromatic ring system, wherein each L may be substituted by one or more groups R;
    x选自0、1、2、3或4；x is selected from 0, 1, 2, 3 or 4;
    B表示芳族环系或-NAr 3Ar 4，在此处L还可以通过基团E与Ar 3和/或Ar 4连接； B represents an aromatic ring system or -NAr 3 Ar 4 , where L can also be linked to Ar 3 and/or Ar 4 via a group E;
    W 1～W 4相同或不同地代表N或CR 2，或者任意两个相邻的基团W 1、W 2、W 3、W 4代表下式(II)或(III)的基团， W 1 to W 4 represent N or CR 2 identically or differently, or any two adjacent groups W 1 , W 2 , W 3 , W 4 represent groups of the following formula (II) or (III),
    Figure PCTCN2022085688-appb-100002
    Figure PCTCN2022085688-appb-100002
    其中，Z在每次出现时相同或不同地代表CR 3或N，并且^指示式I中的相应的相邻基团W 1和W 2、W 2和W 3，或W 3和W 4； wherein Z represents CR 3 or N identically or differently at each occurrence, and ^ indicates the corresponding adjacent groups W 1 and W 2 , W 2 and W 3 , or W 3 and W 4 in formula I;
    T、E选自O、S、NAr 5或CR 4R 5； T, E are selected from O, S, NAr 5 or CR 4 R 5 ;
    Ar 1、Ar 2、Ar 3、Ar 4、Ar 5在每次出现时相同或不同地为具有5至60个碳原子的芳族或杂芳族环系，所述环系中的每个可以被一个或多个基团R 1取代；Ar 1和Ar 2、Ar 3和Ar 4可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系； Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 are, identically or differently at each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, each of which ring systems can be Substituted by one or more groups R 1 ; Ar 1 and Ar 2 , Ar 3 and Ar 4 may optionally be joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system;
    R 1～R 5在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、Si(R 6) 3、具有C 1～C 40的直链烷基、具有C 1～C 40的直链杂烷基、具有C 3～C 40的支链或环状的烷基、具有C 3～C 40的支链或环状的杂烷基、具有C 2～C 40的烯基或炔基基团，所述基团中的每个可被一个或多个基团R 6取代，其中在每种情况下一个或多个非相邻的-CH 2-基团可被R 6C＝CR 6、C≡C、Si(R 6) 2、Ge(R 6) 2、Sn(R 6) 2、C＝O、C＝S、C＝Se、C＝NR 6、P(＝O)(R 6)、SO、SO 2、NR 6、O、S或CONR 6代替，并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替，具有5至80个、优选5至60个碳原子的芳族环或杂芳蔟环系、具有5至60个碳原子的芳氧基或杂芳氧基组成的组，其在每种情况下可以被一个或多个基团R 6取代，或这些基团中的两个、三个、四个或五个的组合，其在每种情况下可以是相同的或不同的，其中两个或更多个相邻的取代基可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系，所述环系可被一个或多个基团R 6取代； R 1 to R 5 are identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, Si(R 6 ) 3 , a linear alkyl group having C 1 to C 40 , a straight chain alkyl group having C 1 ~C 40 straight chain heteroalkyl, C 3 ~C 40 branched or cyclic alkyl, C 3 ~C 40 branched or cyclic heteroalkyl, C 2 ~C 40 Alkenyl or alkynyl groups, each of which may be substituted by one or more radicals R 6 , wherein in each case one or more non-adjacent —CH 2 — groups may be replaced by R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P (=O)(R 6 ), SO, SO 2 , NR 6 , O, S or CONR 6 instead, and wherein one or more hydrogen atoms can be replaced by deuterium atom, halogen atom, nitrile group or nitro group, with 5 to 80, preferably 5 to 60, carbon atoms of aromatic rings or heteroaryl ring systems, aryloxy or heteroaryloxy groups having 5 to 60 carbon atoms, which in each case may be Substitution by one or more groups R 6 , or combinations of two, three, four or five of these groups, which in each case may be the same or different, where two or more Two adjacent substituents may optionally be joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more groups R ;
    R 6在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、Si(R 7) 3、具有 C 1～C 40的直链烷基、具有C 1～C 40的直链杂烷基、具有C 3～C 40的支链或环状的烷基、具有C 3～C 40的支链或环状的杂烷基、具有C 2～C 40的烯基或炔基，所述基团中的每个可被一个或多个基团R 7取代，其中一个或多个非相邻的-CH 2-基团可被R 7C＝CR 7、C≡C、Si(R 7) 2、Ge(R 7) 2、Sn(R 7) 2、C＝O、C＝S、C＝Se、C＝NR 7、P(＝O)(R 7)、SO、SO 2、NR 7、O、S或CONR 7代替，并且其中一个或多个氢原子可被氘原子、卤素原子或腈基代替，具有5至60个碳原子的芳族环或杂芳蔟环系、具有5至60个碳原子的芳氧基或杂芳氧基组成的组，其在每种情况下可以是相同的或不同的，其在每种情况下可以被一个或多个基团R 7取代，其中两个或更多个相邻的取代基R 6可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系，所述环系可被一个或多个基团R 7取代； R 6 is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, Si(R 7 ) 3 , a linear alkyl group having C 1 to C 40 , a straight chain alkyl group having C 1 to C 40 straight-chain heteroalkyl, branched or cyclic alkyl with C 3 to C 40 , branched or cyclic heteroalkyl with C 3 to C 40 , alkenyl with C 2 to C 40 or Alkynyl, each of which may be substituted by one or more groups R 7 , wherein one or more non-adjacent -CH 2 - groups may be replaced by R 7 C=CR 7 , C≡C , Si(R 7 ) 2 , Ge(R 7 ) 2 , Sn(R 7 ) 2 , C=O, C=S, C=Se, C=NR 7 , P(=O)(R 7 ), SO , SO 2 , NR 7 , O, S or CONR 7 instead, and wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms or nitrile groups, aromatic rings or heteroaryl clusters having 5 to 60 carbon atoms ring system, group consisting of aryloxy or heteroaryloxy groups having 5 to 60 carbon atoms, which may in each case be the same or different, which may in each case be replaced by one or more radicals Substituted by group R 7 , wherein two or more adjacent substituents R 6 may optionally be joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system, said ring system Can be substituted by one or more groups R7 ;
    R 7选自氢原子、氘原子、氟原子、腈基、具有C 1～C 20的脂族烃基、具有5～30个碳原子的芳族环或杂芳族环系，其中一个或多个氢原子可被氘原子、卤素原子、或腈基代替，其中任意相邻的两个或多个相邻的R 7可彼此形成单环或多环的脂族、芳族或杂芳族环系。 R 7 is selected from a hydrogen atom, a deuterium atom, a fluorine atom, a nitrile group, an aliphatic hydrocarbon group with C 1 to C 20 , an aromatic ring or a heteroaromatic ring system with 5 to 30 carbon atoms, one or more of which A hydrogen atom can be replaced by a deuterium atom, a halogen atom, or a nitrile group, wherein any adjacent two or more adjacent R can form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system with each other .
  2. 根据权利要求1所述的化合物，其特征在于，所述式(I)选自以下式IV、V、VI、VII、VIII、IX所示化合物：The compound according to claim 1, wherein the formula (I) is selected from compounds shown in the following formulas IV, V, VI, VII, VIII, and IX:
    Figure PCTCN2022085688-appb-100003
    Figure PCTCN2022085688-appb-100003
    其中使用的符号和标记具有在权利要求1中所给出的含义。The symbols and signs used therein have the meanings given in claim 1.
  3. 根据权利要求1或2所述的化合物，其特征在于，所述基团B、Ar 1、Ar 2、Ar 3、Ar 4、Ar 5在每次出现时相同或不同地选自由式(2)～(27)的基团组成的群组： The compound according to claim 1 or 2, characterized in that the groups B, Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 are selected from the formula (2) identically or differently at each occurrence The group consisting of groups of ~(27):
    Figure PCTCN2022085688-appb-100004
    Figure PCTCN2022085688-appb-100004
    Figure PCTCN2022085688-appb-100005
    Figure PCTCN2022085688-appb-100005
    其中，虚线键指示与N连接的位置，并且使用的符号具有在权利要求1中所给出的含义。Wherein, the dotted line key indicates the position connected with N, and the symbols used have the meanings given in claim 1.
  4. 根据权利要求1～3中任一项所述的化合物，其特征在于，所述基团-NAr 1Ar 2或-NAr 3Ar 4具有式(28)、(29)、(30)、(31)或(32)之一的结构，或者所述基团L-NAr 3Ar 4具有式(33)、(34)、(35)、(36)或(37)之一的结构， The compound according to any one of claims 1 to 3, wherein the group -NAr 1 Ar 2 or -NAr 3 Ar 4 has the formulas (28), (29), (30), (31 ) or (32), or the group L-NAr 3 Ar 4 has a structure of one of formulas (33), (34), (35), (36) or (37),
    Figure PCTCN2022085688-appb-100006
    Figure PCTCN2022085688-appb-100006
    其中使用的符号具有在权利要求1中所给出的含义，并且虚线键指示与所述环A键合的位置；The symbols used therein have the meanings given in claim 1, and the dotted bond indicates the bonded position with said ring A;
    Figure PCTCN2022085688-appb-100007
    Figure PCTCN2022085688-appb-100007
    其中使用的符号具有在权利要求1中所给出的含义，并且虚线键指示与所述(L) x的键合位置。 The symbols used therein have the meanings given in claim 1, and the dotted bond indicates the bonding position with said (L) x .
  5. 根据权利要求1～4中任一项所述的化合物，其特征在于，所述基团—(L) x—代表式(38)至(54)之一的基团， The compound according to any one of claims 1 to 4, wherein said group —(L) x —represents a group of one of formulas (38) to (54),
    Figure PCTCN2022085688-appb-100008
    Figure PCTCN2022085688-appb-100008
    其中使用的符号具有在权利要求1中所给出的含义，并且一个虚线键指示与所述环A的键合，而另一个虚线指示与N的键合。The symbols used therein have the meanings given in claim 1, and one dotted bond indicates a bond to said ring A, while the other dotted line indicates a bond to N.
  6. 根据权利要求1～5中任一项所述的化合物，其特征在于，所述化合物中L在每次出现时相同或不同地为芳族环系，其中，对于x＝1或2，—(L) x—选自式(38)～(54)的基团； The compound according to any one of claims 1 to 5, wherein L in the compound is identically or differently each occurrence of an aromatic ring system, wherein, for x=1 or 2,—( L) x —group selected from formula (38)～(54);
    B在每次出现时相同或不同地为芳族环系或NAr 3Ar 4，在此处L还可以通过基团E与Ar 3和/或Ar 4连接； B is identically or differently at each occurrence an aromatic ring system or NAr 3 Ar 4 , where L can also be linked via a group E to Ar 3 and/or Ar 4 ;
    所述B、Ar 1、Ar 2、Ar 3、Ar 4或Ar 5在每次出现时相同或不同地为选自由式(2)～(27)的基团组成的群组；或者NAr 1Ar 2、NAr 3Ar 4代表式(28)～(32)之一的基团； Said B, Ar 1 , Ar 2 , Ar 3 , Ar 4 or Ar 5 are identically or differently selected from the group consisting of groups of formulas (2) to (27) at each occurrence; or NAr 1 Ar 2. NAr 3 Ar 4 represents a group of one of the formulas (28) to (32);
    或者L-NAr 3Ar 4代表式(33)～(37)之一的基团； Or L-NAr 3 Ar 4 represents a group of one of the formulas (33) to (37);
    E在每次出现时相同或不同地选自C(R 3) 2、O、S或NR 4； E is selected at each occurrence, identically or differently, from C(R 3 ) 2 , O, S or NR 4 ;
    x在每次出现时相同或不同地为1或2；x is equally or differently 1 or 2 at each occurrence;
    R 1～R 4在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、Si(R 5) 3、具有C 1～C 10的直链烷基或烷氧基基团、具有C 3～C 10的支链或环状的烷基或烷氧基基团，所述基团中的每个可被一个或多个基团R 5取代，其中在每种情况下一个或多个非相邻的-CH 2-基团可被O代替，并且其中一个或多个氢原子可被氘原子或卤素原子代替，具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系组成的组，其在每种情况下可以是相同的或不同的，其在每种情况下可以被一个或多个基团R 5取代，其中两个或更多个相邻的取代基可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系，所述环系可被一个或多个基团R 5取代； R 1 to R 4 are identically or differently selected from hydrogen atom, deuterium atom, halogen atom, nitrile group, Si(R 5 ) 3 , linear alkyl or alkoxy group having C 1 to C 10 at each occurrence group, a branched or cyclic alkyl or alkoxy group having C 3 to C 10 , each of which may be substituted by one or more groups R 5 , wherein in each case The next one or more non-adjacent -CH2- groups can be replaced by O, and one or more hydrogen atoms can be replaced by deuterium atoms or halogen atoms, with 5 to 80, preferably 5 to 60 carbon atoms The group consisting of aromatic rings or heteroaromatic ring systems, which in each case may be the same or different, which in each case may be substituted by one or more radicals R 5 , of which two or Further adjacent substituents may optionally be joined or fused to form a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more groups R ;
    如果基团R 1与Ar 1、Ar 2、Ar 3、Ar 4或Ar 5键合，则所述基团R 1在每次出现时相同或不同地选自氢原子或氘原子，具有C 1～C 10的直链烷基基团或具有C 3～C 10的支链或环状的烷基基团； If a group R 1 is bonded to Ar 1 , Ar 2 , Ar 3 , Ar 4 or Ar 5 , said group R 1 is selected at each occurrence, identically or differently, from a hydrogen atom or a deuterium atom, with C 1 ~C 10 straight chain alkyl group or C 3 ~C 10 branched or cyclic alkyl group;
    或者在式(28)或(33)中与碳桥连基键合的R 1在每次出现时相同或不同地选自具有C 1～C 10的直链烷基基团或具有C 3～C 10的支链或环状的烷基基团，或者具有5至60个碳原子的芳族环或杂芳蔟环系，其在每种情况下可以被一个或多个基团R 5取代；在此处两个基团R 1还可以彼此形成脂族或芳族的环系； Or R 1 bonded to the carbon bridging group in formula (28) or (33) is identically or differently selected at each occurrence from straight-chain alkyl groups having C 1 to C 10 or having C 3 to C branched or cyclic alkyl radicals, or aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, which may in each case be substituted by one or more radicals R ; the two radicals R 1 can also form an aliphatic or aromatic ring system with one another here;
    或者在式(31)或(36)中与氮桥连基键合的R 1选自具有C 1～C 10的直链烷基基团、具有C 3～C 10的支链或环状的烷基基团，或者具有5至60个碳原子的芳族环或杂芳族环系，其在每种情况下可以被一个或多个基团R 5取代； Or in formula (31) or (36), R 1 bonded to the nitrogen bridge group is selected from straight-chain alkyl groups with C 1 to C 10 , branched or cyclic alkyl groups with C 3 to C 10 Alkyl groups, or aromatic rings or heteroaromatic ring systems having 5 to 60 carbon atoms, which may in each case be substituted by one or more radicals R 5 ;
    R 5在每次出现时相同或不同地选自氢原子、氘原子，具有C 1～C 5的直链烷基、具有C 3～C 6的支链或环状的烷基、具有5至18个碳原子的芳族环或杂芳族环系。 R 5 is identically or differently selected from a hydrogen atom, a deuterium atom, a straight-chain alkyl group having C 1 to C 5 , a branched or cyclic alkyl group having C 3 to C 6 , and a group having 5 to 5 An aromatic ring or heteroaromatic ring system of 18 carbon atoms.
  7. 根据权利要求1～6中任一项所述的化合物，其特征在于，所述化合物包括如式CJHL461～CJHL598所示的化合物：The compound according to any one of claims 1 to 6, characterized in that the compound includes compounds of the formulas CJHL461 to CJHL598:
    Figure PCTCN2022085688-appb-100009
    Figure PCTCN2022085688-appb-100009
    Figure PCTCN2022085688-appb-100010
    Figure PCTCN2022085688-appb-100010
    Figure PCTCN2022085688-appb-100011
    Figure PCTCN2022085688-appb-100011
    Figure PCTCN2022085688-appb-100012
    Figure PCTCN2022085688-appb-100012
    Figure PCTCN2022085688-appb-100013
    Figure PCTCN2022085688-appb-100013
    Figure PCTCN2022085688-appb-100014
    Figure PCTCN2022085688-appb-100014
    Figure PCTCN2022085688-appb-100015
    Figure PCTCN2022085688-appb-100015
    Figure PCTCN2022085688-appb-100016
    Figure PCTCN2022085688-appb-100016
    Figure PCTCN2022085688-appb-100017
    Figure PCTCN2022085688-appb-100017
    Figure PCTCN2022085688-appb-100018
    Figure PCTCN2022085688-appb-100018
  8. 一种有机电致发光装置，其包含第一电极、第二电极和置于所述第一电极、所述第二电极之间的一层以上的有机层，其特征在于，An organic electroluminescent device comprising a first electrode, a second electrode, and more than one organic layer placed between the first electrode and the second electrode, characterized in that,
    所述有机层的至少一层包含权利要求1～7的任一项所述的化合物。At least one of the organic layers contains the compound according to any one of claims 1-7.
  9. 根据权利要求8所述的有机电致发光装置，其特征在于，所述化合物在所述有机电致发光装置中用作空穴传输层或空穴注入层或激子阻挡层中的空穴传输材料或用作荧光发光体或磷光发光体的基质材料。The organic electroluminescent device according to claim 8, characterized in that the compound is used in the organic electroluminescent device as a hole transport layer or a hole injection layer or a hole transport in an exciton blocking layer materials or as host materials for fluorescent emitters or phosphorescent emitters.
  10. 一种电子设备，其具备权利要求8或9所述的有机电致发光装置。An electronic device comprising the organic electroluminescent device according to claim 8 or 9.
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