Organic electroluminescent device and electronic device
Patent Information
- Application Number
- CN202211226718.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2022-10-09
- Publication Date
- 2026-09-04
- Estimated Expiration
- 2042-10-09
AI Technical Summary
[0004]目前,有机电致发光器件的使用过程中仍存在性能较差的问题,例如存在驱动电压过高、发光效率过低或者寿命较短等问题,这些都影响了机电致发光器件的使用领域,因此,仍有必要对该领域进行进一步研究,以改善有机电致发光器件的性能
[0011]本申请有机电致发光器件的发光层主体材料包含所述第一化合物和第二化合物,第一化合物具有苯并二苯并呋喃/噻吩与噁唑/噻唑稠合的母核连接电子传输基团的结构具有强电子传输特性,第二化合物选自吲哚咔唑类化合物或菲并噁唑/噻唑母核具有空穴传输特性,二者混合成红光主体材料。首先,本申请使用的空穴传输材料和电子传输材料均具有比较大的共轭面积,一方面能够降低化合物的第一激发三线态能级,另一方面有助于增强空穴出传输材料和电子传输材料之间的分子作用,能够更有效的形成激基复合物,提高载流子迁移率,从而提高主体材料向发光材料的能量传递效率,最终提高器件的发光效率。其次,本申请使用的第一化合物中,母核中母核与电子传输基团连接,能够将化合物的LUMO(最低空轨道)电子云分布限制在苯并二苯并呋喃/噻吩与噁唑/噻唑部分,抑制激子对芳胺中C-N键的攻击,从而提高器件的寿命。
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Figure CN117412652B_ABST
Abstract
Description
Technical Field
[0001] This application relates to the field of organic electroluminescent materials technology, and more particularly to an organic electroluminescent device and electronic apparatus. Background Technology
[0002] In recent years, organic light-emitting devices (OLEDs) have become a very popular emerging flat panel display product both domestically and internationally. This is because OLED displays have characteristics such as self-illumination, wide viewing angle, short response time, high efficiency, and wide color gamut.
[0003] Organic light-emitting diodes (OLEDs) typically include an anode, a cathode, and an organic layer formed between these two electrodes. This organic layer may include a hole injection layer, a hole transport layer, a hole auxiliary layer, an electron blocking layer, a light-emitting layer (containing host and dopant materials), a hole blocking layer, an electron transport layer, and an electron injection layer. When a voltage is applied to the OLED, holes and electrons are injected into the light-emitting layer from the anode and cathode, respectively. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. These excitons, in an excited state, release energy, causing the light-emitting layer to emit light.
[0004] Currently, organic electroluminescent devices still suffer from poor performance issues during use, such as excessively high driving voltage, low luminous efficiency, or short lifespan. These problems limit their application areas, so further research is necessary to improve their performance. Summary of the Invention
[0005] In view of the above-mentioned problems in the prior art, the purpose of this application is to provide an organic electroluminescent device and electronic device to improve the performance of the device and the apparatus.
[0006] According to a first aspect of this application, an organic electroluminescent device is provided, comprising a cathode, an anode, and an organic layer; The cathode and the anode are arranged opposite to each other; The organic layer is located between the cathode and the anode; The organic layer includes an organic light-emitting layer; The organic light-emitting layer comprises a first compound and a second compound; The first compound has the structure shown in Formula 1:
[0007] Formula 1 Among them, Z1, Z2 and Z3 are each independently selected from N or C(H), and at least one of Z1 to Z3 is N; Y is selected from S or O; One of X1 and X2 is -N=, and the other is O or S; Ring A is selected from naphthalene ring or phenanthrene ring; L1, L2, and L3 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L1, L2, L3, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each R1 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; n1 represents the number of R1s; n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; The second compound has the structure shown in Formula 2 or Formula 3:
[0008] Formula 2 One of X3 and X4 is -N=, and the other is O or S; L4, L5, and L6 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar4, Ar5, and Ar6 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L4, L5, L6, Ar4, Ar5, and Ar6 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each R2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; n2 represents the number of R2; n2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7;
[0009] Formula 3 The C ring and the E ring are each independently selected from aromatic rings with 6 to 14 carbon atoms; L7 and L8 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar7 and Ar8 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L7, L8, Ar7, and Ar8 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each of R3, R4, and R5 may be the same or different, and is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; optionally, any two adjacent R4s form a ring; n3 represents the number of R3s, n4 represents the number of R4s, and n5 represents the number of R5s; n3 and n5 are each independently selected from 0, 1, 2, 3, 4, 5, or 6; n4 is selected from 0, 1, or 2.
[0010] According to a second aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the first aspect.
[0011] The host material of the light-emitting layer of the organic electroluminescent device of this application comprises the first compound and the second compound. The first compound has a structure with a fused core of benzodibenzofuran / thiophene and oxazole / thiazole connected to an electron transport group, exhibiting strong electron transport properties. The second compound is selected from indolecarbazole compounds or phenanthreneoxazole / thiazole cores, exhibiting hole transport properties. The two are mixed to form the red light host material. First, both the hole transport material and the electron transport material used in this application have relatively large conjugated areas. On the one hand, this can reduce the first excited triplet energy level of the compound; on the other hand, it helps to enhance the molecular interaction between the hole transport material and the electron transport material, enabling more effective formation of excitocomplexes, increasing carrier mobility, thereby improving the energy transfer efficiency from the host material to the light-emitting material, and ultimately improving the luminous efficiency of the device. Second, in the first compound used in this application, the core is connected to the electron transport group, which can confine the LUMO (lowest empty orbital) electron cloud distribution of the compound to the benzodibenzofuran / thiophene and oxazole / thiazole parts, suppressing exciton attack on the CN bond in the aromatic amine, thereby improving the device lifetime. Attached Figure Description
[0012] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.
[0013] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.
[0014] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.
[0015] Figure Labels 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer 321, Hole Transport Layer 322, Hole Adjustment Layer 330, Organic light-emitting layer; 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device. Detailed Implementation
[0016] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided to make this application more comprehensive and complete, and to fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.
[0017] For clarity, the thickness of regions and layers may be exaggerated in the figures. The same reference numerals in the figures denote the same or similar structures, and therefore their detailed descriptions will be omitted.
[0018] In a first aspect, this application provides an organic electroluminescent device, including a cathode, an anode, and an organic layer; The cathode and the anode are arranged opposite to each other; The organic layer is located between the cathode and the anode; The organic layer includes an organic light-emitting layer; The organic light-emitting layer comprises a first compound and a second compound; The first compound has the structure shown in Formula 1:
[0019] Formula 1 Among them, Z1, Z2 and Z3 are each independently selected from N or C(H), and at least one of Z1 to Z3 is N; Y is selected from S or O; One of X1 and X2 is -N=, and the other is O or S; Ring A is selected from naphthalene ring or phenanthrene ring; L1, L2, and L3 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L1, L2, L3, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each R1 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; n1 represents the number of R1s; n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; The second compound has the structure shown in Formula 2 or Formula 3:
[0020] Formula 2 One of X3 and X4 is -N=, and the other is O or S; L4, L5, and L6 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar4, Ar5, and Ar6 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L4, L5, L6, Ar4, Ar5, and Ar6 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each R2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; n2 represents the number of R2; n2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7;
[0021] Formula 3 The C ring and the E ring are each independently selected from aromatic rings with 6 to 14 carbon atoms; L7 and L8 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar7 and Ar8 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L7, L8, Ar7, and Ar8 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each of R3, R4, and R5 may be the same or different, and is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; optionally, any two adjacent R4s form a ring; n3 represents the number of R3s, n4 represents the number of R4s, and n5 represents the number of R5s; n3 and n5 are each independently selected from 0, 1, 2, 3, 4, 5, or 6; n4 is selected from 0, 1, or 2.
[0022] In this application, the terms "optionally" or "optionally" mean that the events or circumstances described below may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring" includes: the scenario where any two adjacent substituents form a ring, and the scenario where any two adjacent substituents exist independently and do not form a ring. "Any two adjacent" can include having two substituents on the same atom, and can also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spirocyclic ring with the atom they are connected to; when there is one substituent on each of two adjacent atoms, the two substituents can fuse into a ring.
[0023] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, " In the formula Q-1, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.
[0024] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl group having a substituent Rc or an unsubstituted aryl group. The substituents mentioned above, i.e., Rc, can be, for example, deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms, etc. The number of substituents can be one or more.
[0025] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.
[0026] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms.
[0027] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).
[0028] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirodifluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, phenylene, etc.
[0029] In this application, the term "arylene" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.
[0030] In this application, terphenyl includes and .
[0031] In this application, the substituted or unsubstituted aryl (arylene) group can have 6, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40 carbon atoms. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 18 carbon atoms; and in yet another embodiment, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 15 carbon atoms.
[0032] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: , , , etc., but not limited to this.
[0033] In this application, aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, etc.
[0034] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms. The heteroatoms can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc.
[0035] In this application, the term "hybrid aryl" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.
[0036] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group (hybrid aryl group) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 30; in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 12 to 18; and in still other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 5 to 12.
[0037] In this application, the heteroaryl groups used as substituents include, but are not limited to, pyridyl, carbazolyl, dibenzothiophene, dibenzofuranyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl.
[0038] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc.
[0039] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.
[0040] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
[0041] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.
[0042] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.
[0043] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.
[0044] In this application, the number of carbon atoms in the deuterated alkyl group is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl.
[0045] In this application, the number of carbon atoms in the alkyl halogroup is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of alkyl halogroups include, but are not limited to, trifluoromethyl.
[0046] In this application, a ring system formed by n atoms is called an n-membered ring. For example, phenyl is a 6-membered ring. 3- to 15-membered rings refer to cyclic groups having 3 to 15 ring atoms. Examples of 3- to 15-membered rings include cyclopentane, cyclohexane, fluorene rings, and benzene rings.
[0047] In this application, It refers to the chemical bond that connects with other groups.
[0048] In this application, the single bond extending from the loop system involved in the non-positioning link is not specified. " or" The term "" indicates that one end of the linker can connect to any position in the ring system it traverses, while the other end connects to the rest of the compound molecule. For example, as shown in equation (f), the naphthyl group represented by equation (f) is connected to other positions in the molecule via two non-positional linkers that traverse the bicyclic ring. This means that any possible connection configuration shown in equations (f-1) to (f-10) is acceptable.
[0049] .
[0050] For another example, as shown in equation (X'), the dibenzofuran group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in equations (X'-1) to (X'-4) is included. .
[0051] In this application, a non-orienting substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in equation (Y) below, the substituent R' represented by equation (Y) is connected to the quinoline ring by a non-orienting linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7):
[0052] .
[0053] In some embodiments, Z1, Z2 and Z3 in the first compound are each independently selected from N or C(H), and at least one of Z1 to Z3 is N.
[0054] More specifically, in some embodiments of this application, in the first compound, X1 and X2 are both C(H), and X3 is N; or X1 and X3 are both C(H), and X2 is N; or X2 and X3 are both C(H), and X1 is N; or X1 and X2 are both N, and X3 is C(H); or X1 and X3 are both N, and X2 is C(H); or X2 and X3 are both N, and X1 is C(H); or X1, X2, and X3 are all N.
[0055] In some implementations, Z1, Z2 and Z3 are each independently selected from N or C(H), and at least two of Z1 to Z3 are N; or Z1, Z2 and Z3 are all N.
[0056] In some embodiments, the first compound is selected from the structures shown in 1-1 to 1-15 below: Where Y is O or S.
[0057] In some embodiments, in the first compound, Ar1, Ar2, and Ar3 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40 carbon atoms.
[0058] Optionally, the substituents in Ar1, Ar2 and Ar3 are each independently selected from deuterium, halogen groups, cyano, haloalkyl with 1 to 4 carbon atoms, deuteralkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 15 carbon atoms, heteroaryl with 5 to 12 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms or deuteralkyl with 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.
[0059] In some embodiments, in the first compound, Ar1, Ar2, and Ar3 are each independently selected from substituted or unsubstituted groups W1; the unsubstituted group W1 is selected from the group consisting of: ; The substituted group W1 has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, benzoxazolyl, or benzothiazolyl. When the number of substituents on group W1 is greater than 1, the substituents may be the same or different.
[0060] In some embodiments, in the first compound, Ar1, Ar2, and Ar3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, and substituted or unsubstituted pyridyl.
[0061] Optionally, the substituents in Ar1, Ar2 and Ar3 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl or carbazoyl. Optionally, any two adjacent substituents in Ar1 and Ar2 form a benzene ring.
[0062] In some embodiments, in the first compound, and Each is independently selected from the following groups:
[0063] In some embodiments, in the first compound, Ar1 and Ar2 are each independently selected from the group consisting of: .
[0064] In some embodiments, in the first compound, Ar3 is selected from the group consisting of: .
[0065] In some embodiments, in the first compound, L1, L2, and L3 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
[0066] Optionally, the substituents in L1, L2 and L3 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, deuterylalkyl with 1 to 4 carbon atoms, phenyl or naphthyl.
[0067] In some embodiments, in the first compound, L1, L2, and L3 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted benzoxazolyl, and substituted or unsubstituted benzothiazolyl.
[0068] Optionally, the substituents in L1, L2 and L3 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.
[0069] In some embodiments, in the first compound, L3 is selected from the group consisting of single bonds or the following groups: .
[0070] In some embodiments, in the first compound, L1 and L2 are each independently selected from the group consisting of single bonds or the following groups: .
[0071] In some embodiments, in the first compound, each R1 may be the same or different, and each is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or carbazoleyl.
[0072] In some embodiments, the second compound is selected from the structures shown in formula (2-1), (2-2) or formulas (3-1) to (3-20).
[0073] In some embodiments, the compound of formula 2 has the structure shown in formula 2-1 or 2-2: .
[0074] In some embodiments, in Formula 2, Ar4, Ar5, and Ar6 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40 carbon atoms.
[0075] Optionally, the substituents in Ar4, Ar5 and Ar6 are each independently selected from deuterium, halogen groups, cyano, haloalkyl with 1 to 4 carbon atoms, deuteralkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 15 carbon atoms, heteroaryl with 5 to 12 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms or deuteralkyl with 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.
[0076] In some embodiments, in Formula 2, Ar4, Ar5, and Ar6 are each independently selected from substituted or unsubstituted groups W2; the unsubstituted group W2 is selected from the group consisting of: ; The substituted group W2 has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoleyl. When the number of substituents on group W2 is greater than 1, the substituents may be the same or different.
[0077] In some embodiments, in Formula 2, Ar4, Ar5, and Ar6 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted benzimidazolyl.
[0078] Optionally, the substituents in Ar4, Ar5 and Ar6 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl or carbazoyl. Optionally, in Ar4 and Ar5, any two adjacent substituents form a benzene ring.
[0079] In some implementations... and Each is independently selected from the following groups:
[0080] In some embodiments, in Formula 2, Ar4 and Ar5 are each independently selected from the group consisting of: .
[0081] In some embodiments, in Formula 2, Ar6 is selected from the group consisting of: .
[0082] In some embodiments, in Formula 2, L4, L5, and L6 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
[0083] Optionally, the substituents in L4, L5 and L6 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, deuterylalkyl with 1 to 4 carbon atoms, phenyl or naphthyl.
[0084] In some embodiments, in Formula 2, L4, L5 and L6 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl.
[0085] Optionally, the substituents in L4, L5 and L6 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.
[0086] In some embodiments, in Formula 2, L4 is selected from the group consisting of single bonds or the following groups: .
[0087] In some embodiments, in Formula 2, L5 and L6 are each independently selected from the group consisting of single bonds or the following groups: .
[0088] In some embodiments, in Formula 2, each R2 may be the same or different, and each is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or carbazoleyl.
[0089] In some embodiments, the second compound is selected from the structures shown in formulas (3-1) to (3-20):
[0090] In some embodiments, ring C and ring E in Formula 3 are each independently selected from benzene rings or naphthalene rings.
[0091] In some embodiments, in Formula 3, L7 and L8 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms.
[0092] Optionally, the substituents in L7 and L8 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, deuterylalkyl with 1 to 4 carbon atoms, phenyl or naphthyl.
[0093] In some embodiments, in Formula 3, L7 and L8 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthracene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl.
[0094] Optionally, the substituents in L7 and L8 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.
[0095] In some embodiments, in Formula 3, L7 and L8 are each independently selected from the group consisting of single bonds or the following groups: .
[0096] In some embodiments, in Formula 3, Ar7 and Ar8 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40 carbon atoms.
[0097] In some embodiments, in Formula 3, the substituents in Ar7 and Ar8 are each independently selected from deuterium, halogen groups, cyano, haloalkyl with 1 to 4 carbon atoms, deuteralkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 15 carbon atoms, heteroaryl with 5 to 12 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, or deuteralkyl with 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.
[0098] In some embodiments, in Formula 3, Ar7 and Ar8 are each independently selected from substituted or unsubstituted groups W3; the unsubstituted group W3 is selected from the group consisting of: ; The substituted group W3 has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiopheneyl or carbazoleyl, and when the number of substituents on group W3 is greater than 1, the substituents may be the same or different.
[0099] In some embodiments, in Formula 3, Ar7 and Ar8 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted benzimidazolyl, and substituted or unsubstituted pyridyl.
[0100] Optionally, the substituents in Ar7 and Ar8 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, or carbazoyl. Optionally, any two adjacent substituents in Ar7 and Ar8 form a benzene ring.
[0101] In some embodiments, in Formula 3, Ar7 and Ar8 are each independently selected from the group consisting of: .
[0102] In some implementations... and Each is independently selected from the following groups: .
[0103] In some embodiments, each R1 may be the same or different, and each is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or carbazoleyl.
[0104] In some embodiments, in Formula 2, each R2 may be the same or different, and each is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or carbazoyl.
[0105] In some embodiments, in Formula 3, each of R3, R4 and R5 may be the same or different, and each is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
[0106] In some embodiments, the first compound is selected from the compounds shown in A-1 to A-276 below:
[0107]
[0108]
[0109]
[0110]
[0111]
[0112]
[0113]
[0114]
[0115]
[0116]
[0117]
[0118]
[0119]
[0120]
[0121]
[0122]
[0123]
[0124]
[0125]
[0126]
[0127]
[0128]
[0129]
[0130]
[0131]
[0132]
[0133]
[0134]
[0135]
[0136]
[0137]
[0138]
[0139]
[0140]
[0141]
[0142]
[0143]
[0144]
[0145]
[0146]
[0147]
[0148]
[0149]
[0150] .
[0151] In some embodiments, the second compound is selected from compounds shown below as B1-~B-162 and C-1~C-104:
[0152]
[0153]
[0154]
[0155]
[0156]
[0157]
[0158]
[0159]
[0160]
[0161]
[0162]
[0163]
[0164]
[0165]
[0166]
[0167]
[0168]
[0169]
[0170]
[0171]
[0172]
[0173]
[0174]
[0175]
[0176]
[0177]
[0178]
[0179]
[0180]
[0181]
[0182]
[0183]
[0184]
[0185]
[0186]
[0187]
[0188]
[0189]
[0190]
[0191]
[0192]
[0193] .
[0194] This application also provides a light-emitting layer composition comprising a first compound and a second compound, wherein the first compound has the structure shown in Formula 1:
[0195] Formula 1 Among them, Z1, Z2 and Z3 are each independently selected from N or C(H), and at least one of Z1 to Z3 is N; Y is selected from S or O; One of X1 and X2 is -N=, and the other is O or S; Ring A is selected from naphthalene ring or phenanthrene ring; L1, L2, and L3 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L1, L2, L3, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each R1 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; n1 represents the number of R1s; n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; The second compound has the structure shown in Formula 2 or Formula 3:
[0196] Formula 2 One of X3 and X4 is -N=, and the other is O or S; L4, L5, and L6 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar4, Ar5, and Ar6 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L4, L5, L6, Ar4, Ar5, and Ar6 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each R2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; n2 represents the number of R2; n2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7;
[0197] Formula 3 The C ring and the E ring are each independently selected from aromatic rings with 6 to 14 carbon atoms; L7 and L8 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar7 and Ar8 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L7, L8, Ar7, and Ar8 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each of R3, R4, and R5 may be the same or different, and is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; optionally, any two adjacent R4s form a ring; n3 represents the number of R3s, n4 represents the number of R4s, and n5 represents the number of R5s; n3 and n5 are each independently selected from 0, 1, 2, 3, 4, 5, or 6; n4 is selected from 0, 1, or 2.
[0198] Optionally, the mass ratio of the first compound to the second compound in the light-emitting layer composition is 1:99 to 99:1, preferably 10:90 to 90:10, more preferably 30:70 to 70:30, and even more preferably 40:60 to 60:40.
[0199] This application also provides the use of the light-emitting layer composition in the light-emitting layer of an organic electroluminescent device.
[0200] This application also provides an organic electroluminescent device comprising the composition.
[0201] The organic electroluminescent device provided in this application includes an anode and a cathode disposed opposite to each other, and an organic layer. The organic layer includes an organic light-emitting layer, which comprises a first compound and a second compound.
[0202] Furthermore, the organic light-emitting layer comprises a host material and a dopant. The host material comprises a first compound and a second compound. Typically, based on the total weight of the two compounds, the mass ratio of the first compound to the second compound is 1:99 to 99:1, preferably 10:90 to 90:10, more preferably 30:70 to 70:30, and even more preferably 40:60 to 60:40.
[0203] In some embodiments, the mass ratio of the first compound (compound of formula 1) and the second compound (compound of formula 2) in the light-emitting layer of the organic electroluminescent device is 30:70 to 70:30.
[0204] Optionally, in the main material, the mass ratio of the first compound (compound of formula 1) and the second compound (compound of formula 2) is 35:65, 40:60, 45:55, 50:50, 55:45, 60:40, or 65:35.
[0205] To obtain a mixture of main materials, the first and second compounds can be placed in an oscillator and mixed to obtain a mixture in the desired weight ratio.
[0206] To form each layer constituting the organic electroluminescent device of this application, dry film formation methods such as vacuum deposition, sputtering, plasma, ion plating, etc., or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc., can be used.
[0207] Furthermore, the first and second compounds can be film-formed using the methods listed above, typically via co-evaporation or mixed evaporation. Co-evaporation is a mixed deposition method in which two or more materials are placed in respective individual crucible sources and an electric current is simultaneously applied to multiple chambers to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in a crucible source before evaporation and an electric current is applied to a chamber to evaporate the materials.
[0208] In some embodiments of this application, the organic electroluminescent device is a phosphorescent device.
[0209] In some specific embodiments of this application, the organic electroluminescent device is a green organic electroluminescent device or a red organic electroluminescent device.
[0210] In some embodiments of this application, the organic electroluminescent device sequentially comprises an anode (e.g., an ITO / Ag / ITO substrate), a hole transport layer, a hole conditioning layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, a cathode (e.g., a Mg-Ag mixture), and an organic capping layer. The hole transport layer is located between the anode and the organic light-emitting layer, and the hole conditioning layer is located between the hole transport layer and the organic light-emitting layer.
[0211] According to a specific implementation method, such as Figure 1 As shown, the organic electroluminescent device includes an anode 100, a hole injection layer 310, a hole transport layer 321, a hole adjustment layer (also known as a hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are stacked in sequence.
[0212] In this application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.
[0213] In this application, the hole transport layer or the hole conditioning layer may each include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:
[0214]
[0215]
[0216] .
[0217] In one embodiment, the hole transport layer 321 is composed of HT-1 or HT-5.
[0218] In one embodiment, the hole adjustment layer 322 is composed of HT-2 or HT-1.
[0219] Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials, and this application does not impose any special limitations on this. The material of the hole injection layer 310 can be selected from, for example, the following compounds or any combination thereof;
[0220] HAT-CNF4-TCNQ .
[0221] In one embodiment of this application, the hole injection layer 310 is composed of PD and HT-1 or PD and HT-5.
[0222] Optionally, the organic light-emitting layer 330 may include the host material and the guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
[0223] The main material of the organic light-emitting layer 330 includes the first compound and the second compound.
[0224] The guest material of the organic light-emitting layer 330 can be a compound or its derivative having a condensed aryl ring, a compound or its derivative having a heteroaryl ring, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. For example, specific examples of phosphorescent dopant include, but are not limited to, [Ir(flq)2(acac)] (Ir(Mphq)3),
[0225] (RD-1).
[0226] In one embodiment of this application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 is composed of the first compound and the second compound. The guest material may be, for example, RD-1.
[0227] In another embodiment, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 is composed of the first compound and the second compound. The guest material can be, for example, […]. fac -Ir(ppy)3.
[0228] The electron transport layer 340 can be a single-layer structure or a multi-layer structure, and can include one or more electron transport materials. These electron transport materials can be selected from, but are not limited to, BmPyPhB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, triazine derivatives, etc., and this application does not impose any specific limitations on them. The material of the electron transport layer 340 includes LiQ and other electron transport materials, which can be selected from, but are not limited to, the following compounds: , (ET-2) , , , , , , (ET-1) (BmPyPhB) .
[0229] In one embodiment of this application, the electron transport layer 340 is composed of ET-1 and LiQ.
[0230] In this application, the cathode 200 includes a cathode material that has a small work function and facilitates electron injection into the functional layers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver may be included as the cathode.
[0231] Optionally, an electron injection layer 350 is further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In one embodiment of this application, the electron injection layer 350 includes ytterbium (Yb).
[0232] This application not only provides the organic electroluminescent device comprising the compound represented by Formula 1 and the compound represented by Formula 2 for the organic light-emitting layer, but also provides an electronic device comprising the organic electroluminescent device of this application.
[0233] According to one implementation method, such as Figure 2 As shown, the provided electronic device is electronic device 400. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.
[0234] The synthesis methods of the first and second compounds of this application are described in detail below with reference to the synthesis examples, but this application is not limited thereto.
[0235] Synthesis Examples Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the heterocyclic compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this application are commercially available starting materials.
[0236] Synthesis of the first compound: Synthesis of 7-bromo-1-iodo-2-naphthiophenol:
[0237] Under a nitrogen atmosphere, 7-bromo-1-iodo-2-naphthylamine (CAS: 2411719-24-7, 17.40 g, 50 mmol), concentrated hydrochloric acid (25 mL), and deionized water (25 mL) were added sequentially to a 1000 mL three-necked flask. The system was cooled to 0 °C using an ice-water bath. An aqueous solution of sodium nitrite (3.45 g, 50 mmol) (25 mL) was added dropwise to the system. After the addition was complete, an aqueous solution of potassium thiocyanate (9.72 g, 100 mmol) and ferric chloride (4.1 g, 25 mmol) (25 mL) was added dropwise to the reaction system. After the addition was complete, the system was slowly heated to room temperature and stirred overnight. The reaction solution was poured into deionized water (200 mL) and extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was used directly in the next reaction without purification.
[0238] Under a nitrogen atmosphere, the crude product, sodium sulfide nonahydrate (9.61 g, 100 mmol), ethanol (180 mL), and deionized water (360 mL) were added in one batch to a 1000 mL three-necked flask. The mixture was heated to reflux and stirred for 16 h. After the reaction system cooled to room temperature, it was filtered. The filtrate was acidified to pH 2 with 1 M hydrochloric acid and then extracted with dichloromethane (100 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (8.03 g, yield 44%).
[0239] Synthesis of Sub-a1:
[0240] Under a nitrogen atmosphere, 7-bromo-2-phenylbenzoxazole (CAS: 1268137-13-8, 12.06 g, 44 mmol), pinacol diborate (12.28 g, 48.4 mmol), potassium acetate (9.50 g, 96.8 mmol), and 1,4-dioxane (120 mL) were added sequentially to a 500 mL three-necked flask. The mixture was stirred and heated until it reached 40 °C. Then, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.40 g, 0.44 mmol) and (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (XPhos, 0.42 g, 0.88 mmol) were added rapidly. The mixture was then heated to reflux and stirred overnight. After the system cooled to room temperature, 200 mL of water was added to the system and stirred thoroughly for 30 min. The mixture was then filtered under reduced pressure. The filter cake was washed with deionized water until neutral and then rinsed with 100 mL of anhydrous ethanol. The filter cake was collected to obtain a gray solid. The crude product was slurried once with n-heptane, then dissolved in 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-a1 (10.17 g, yield 72%) was obtained.
[0241] Referring to the synthesis of Sub-a1, Sub-a2 to Sub-a4 were synthesized by replacing 7-bromo-2-phenylbenzoxazole with reactant A shown in Table 1.
[0242] Table 1: Synthesis of Sub-a2 and Sub-a4
[0243] Synthesis of Sub-b1:
[0244] Under a nitrogen atmosphere, Sub-a1 (17.66 g, 55 mmol), 7-bromo-1-iodo-2-hydroxynaphthalene (17.45 g, 50 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL), and deionized water (45 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 h. After cooling to room temperature, the mixture was extracted with dichloromethane (150 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation of the filtrate to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (11.03 g, yield 53%).
[0245] Referring to the synthesis of Sub-a1, Sub-b2 to Sub-b11 were synthesized by replacing Sub-a1 with reactant Sub aX as shown in Table 2 and replacing 7-bromo-1-iodo-2-hydroxynaphthalene with reactant B.
[0246] Table 2: Synthesis of Sub-b2 to Sub-b11
[0247] Synthesis of Sub-c1:
[0248] Under a nitrogen atmosphere, Sub-b1 (20.81 g, 50 mmol), tert-butyl peroxide (BzOOt-Bu, 19.42 g, 100 mmol), palladium acetate (1.12 g, 5 mmol), 3-nitropyridine (0.62 g, 5 mmol), hexafluorobenzene (C6F6, 210 mL), and N,N'-dimethylimidazolinone (DMI, 140 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the reaction was carried out at 90 °C for 4 h. After the system cooled to room temperature, extraction with ethyl acetate (100 mL × 3 times) was performed. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation of the filtrate to obtain the crude product. Purification of the crude product by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase yielded a white solid (10.77 g, 52% yield).
[0249] Referring to Sub-c1, use Sub-bX as shown in Table 3 to replace Sub-b1, and synthesize Sub-c2 to Sub-c11.
[0250] Table 3: Synthesis of Sub-c2 to Sub-c11
[0251] Synthesis of Sub-c11:
[0252] Under a nitrogen atmosphere, add Sub-Cl (10.36 g, 25 mmol) and 200 mL of benzene to a 100 mL three-necked flask. D6, after heating to 60℃, added trifluoromethanesulfonic acid (22.51 g, 150 mmol), and continued heating to boiling with stirring for 24 hours. After the reaction system cooled to room temperature, added 50 mL of heavy water, stirred for 10 minutes, and then added saturated K3PO4 aqueous solution to neutralize the reaction solution. The organic layer was extracted with dichloromethane (50 mL × 3 times), the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation of the filtrate to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid Sub-C10 (6.82 g, yield 64%).
[0253] Synthesis of Sub-c12:
[0254] Under a nitrogen atmosphere, Sub-b12 (10.80 g, 25 mmol), palladium dichloride (0.22 g, 1.25 mmol), and DMSO (120 mL) were added to a 250 mL three-necked flask. The mixture was heated to 140 °C and stirred for 12 hours. After the reaction system cooled to room temperature, the organic layer was extracted with dichloromethane (50 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation of the filtrate to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid, Sub-c13 (7.85 g, yield 73%).
[0255] Synthesis of Sub-d1:
[0256] Under a nitrogen atmosphere, Sub-Cl (13.36 g, 50 mmol), 4-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL), and deionized water (35 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 16 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation of the filtrate to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (13.82 g, yield 62%).
[0257] Referring to the synthesis of Sub-d1, Sub-c1 was synthesized by replacing it with Sub-cX as shown in Table 5, and reactant C was replaced with 4-chlorophenylboronic acid. Sub-d2 to Sub-d8 were then synthesized. Table 5: Synthesis of Sub-d2 to Sub-d8
[0258] Preparation of compound A2
[0259] Intermediate Sub-c1 (35.0 g, 84.8 mmol) was added to a round-bottom flask. 350 mL of dehydrated THF was added to the flask. The system was cooled to -80°C to -90°C using liquid nitrogen. Lithium n-butyl (6.5 g, 101.4 mmol) was then added dropwise. After the addition was complete, the temperature was maintained for 1 h. Trimethyl borate (11.4 g, 109.8 mmol) was then added dropwise, maintaining the temperature at -80°C to -90°C. After the addition was complete, the temperature was maintained for 1 h, and the reaction was allowed to rise naturally to room temperature. Once the reaction was complete, 100 mL of an aqueous solution of HCl (2 mol / L) was added, and the mixture was stirred for 0.5 h. Dichloromethane and water were added for separation extraction. The organic phase was washed to neutral pH 7. The organic phases were combined, dried over anhydrous MgSO4 for 10 min, filtered, and the filtrate was evaporated to dryness. The filtrate was then slurried twice with n-heptane to obtain a white solid intermediate, Sub-e1 (16.0 g, 50% yield).
[0260] Sub-e1 (16.0 g, 42.2 mmol), 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-triazine (14.5 g, 42.2 mmol), tetratriphenylphosphine palladium (0.5 g, 0.4 mmol), potassium carbonate (11.6 g, 84.4 mmol), tetrabutylammonium bromide (0.1 g, 0.4 mmol), toluene (128 mL), ethanol (64 mL), and deionized water (32 mL) were added to a three-necked flask. The mixture was heated to 76 °C under nitrogen protection and stirred under reflux for 8 h. After the reaction was complete, the solution was cooled to room temperature, and the reaction solution was extracted with toluene and water. The organic phases were combined, the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography to give solid compound A2 (16.8 g, yield 62%, m / z = 643.2 [M+H]). + ).
[0261] Sub-eX was synthesized by replacing Sub-c1 with the reactant Sub-cX shown in Table 6, referring to Sub-c1.
[0262] Table 6: Synthesis of Sub-e2 to Sub-e10
[0263] Compound AX, shown in the table below, was synthesized using a method similar to that used for A2, except that starting material 1 was used instead of 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-triazine, and Sub-eX was used instead of sub-e1.
[0264] Table 7: Synthesis of compound AX
[0265] Mass spectrometry analysis was performed on some of the synthesized compounds, and the analytical results are shown in Table 8 below: Table 8: Mass spectrometry data of compound AX
[0266] Synthesis of the second compound: Synthesis of intermediate sub-I-A1
[0267] 1) Preparation of intermediate sub 1-I-A1 2-Bromocarbazole (30.0 g, 121.8 mmol), iodobenzene (24.8 g, 78.03 mmol), CuI (4.64 g, 24.3 mmol), K₂CO₃ (37.0 g, 268.1 mmol), and 18-crown ether-6 (3.2 g, 12.1 mmol) were added to a three-necked flask, along with 300 mL of dried DMF solvent. Under nitrogen protection, the mixture was heated to 150 °C and stirred for 17 hours. After cooling to room temperature, stirring was stopped. The reaction mixture was washed with water to separate the organic phase, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid intermediate, sub1-I-A1 (26.3 g, 67% yield).
[0268] 2) Preparation of intermediate sub 1-II-A1 The intermediates sub 1-I-A1 (26.0 g, 80.6 mmol), o-chloroaniline (11.3 g, 88.7 mmol), and Pd(dba)2 (0.73 g, 0.8 mmol) were used. 2-Dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (x-phos, 0.76 g, 1.6 mmol) and sodium tert-butoxide (11.6 g, 121.0 mmol) were added to a three-necked flask, along with 300 mL of toluene as solvent. Under nitrogen protection, the mixture was heated to 110 °C and stirred for 15 hours. After cooling to room temperature, stirring was stopped. The reaction mixture was washed with water to separate the organic phase, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid intermediate, sub 1-I-A1 (15.7 g, 53% yield).
[0269] 3) Preparation of intermediate sub-A1 Intermediate sub 1-I-A1 (15.0 g, 46.5 mmol), cesium carbonate (37.9 g, 116.3 mmol), tricyclohexylphosphonoborate (8.5 g, 23.2 mmol), and Pd(dba)2 (0.52 g, 2.3 mmol) were added to a three-necked flask, along with 150 mL of toluene solvent. Under nitrogen protection, the mixture was heated to 110 °C and stirred for 10 hours. After cooling to room temperature, stirring was stopped. The reaction mixture was washed with water, and the organic phase was separated. The solution was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain the white solid intermediate sub-A1 (9.43 g, yield 61%).
[0270] In the table below, if 2-bromocarbazole is substituted with reactant 3, iodobenzene with reactant 3, and o-chloroaniline with reactant 4, intermediates Sub-A2 to Sub-A10 shown in Table 9 can be synthesized using a method similar to sub-A1: Table 9: Synthesis of intermediates Sub-A2 to Sub-A10
[0271] Synthesis of compound B1
[0272] Intermediate sub-A1 (9.0 g, 27.0 mmol), 1-bromo-4-(2-phenyl)benzene (8.3 g, 27.0 mmol), tris(dibenzylacetone)palladium (0.2 g, 0.3 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (0.2 g, 0.5 mmol), and sodium tert-butoxide (5.2 g, 154.1 mmol) were added to a three-necked flask, along with 300 mL of toluene solvent. Under nitrogen protection, the mixture was heated to 110 °C and stirred for 15 hours. After cooling to room temperature, stirring was stopped, and the reaction mixture was washed with water to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid product B1 (9.9 g, 64% yield). Mass spectrometry: m / z = 561.2 [M+H] + .
[0273] In the table below, intermediates sub-A2 to sub-A10 replace intermediate sub-A1, and starting material 5 replaces 1-bromo-4-(2-phenyl)benzene. Compounds shown in Table 10 are synthesized using a similar method: Table 10: Synthesis of compound BX
[0274] Mass spectrometry analysis was performed on some of the synthesized compounds, and the analytical results are shown in Table 11 below: Table 11: Mass spectra of compound BX
[0275] C22 synthesis of compounds:
[0276] Under a nitrogen atmosphere, 10-chloro-2-phenylphenanthrene[3,4-D]azole (10.0 g, 30.3 mmol), N-phenyl-4-benzidine (CAS: 32228-99-2, 7.5 g, 30.9 mmol), tris(dibenzylacetone)palladium (0.27 g, 0.3 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (X-phos, 0.28 g, 0.6 mmol), sodium tert-butoxide (4.4 g, 45.4 mmol), and toluene (100 mL) were added sequentially to a 250 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to give a white solid compound C22 (12.7 g, yield 78%, m / z = 539.2 [M+H]). + ).
[0277] Referring to the synthesis of compound 3, the compounds in Table 12 were synthesized by replacing N-phenyl-4-benzidine with starting material 6 shown in Table 12.
[0278] Table 12: Synthesis of compound CX
[0279] Synthesis of compound C12
[0280] 10-Chloro-2-phenylphenanthrene[3,4-D]azole (35.0 g, 106.1 mmol), pinacol diboronate (32.3 g, 127.3 mmol), Pd(dppf)Cl2 (0.7 g, 1.1 mmol), and KOAc (20.8 g, 212.2 mmol) were added to 1,4-dioxane (350 mL) and refluxed at 100 °C for 12 h. At the end of the reaction, the mixture was extracted with CH2Cl2 and water. The organic layer was dried and concentrated using MgSO4, and the resulting compound was subjected to silica gel column chromatography and recrystallization to give compound sub-B1 (28.6 g, 64% yield).
[0281] Sub-B1 (25.0 g, 59.3 mmol), N-(4-bromophenyl-)-N-phenylbenzidine (23.7 g, 59.3 mmol), tetratetraphenylphosphine palladium (0.7 g, 0.6 mmol), potassium carbonate (16.4 g, 118.6 mmol), and tetrabutylammonium bromide (0.2 g, 0.6 mmol) were added to a three-necked flask. Toluene (200 mL), ethanol (100 mL), and deionized water (50 mL) were added to the flask. The mixture was heated to 76 °C under nitrogen protection and stirred under reflux for 18 h. After cooling to room temperature, stirring was stopped. The reaction mixture was washed with water to separate the organic phase, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain the white product C12 (24.7 g, yield 68%, m / z = 615.2 [M+H]). + ).
[0282] Referring to the synthesis of compound C12, the compounds in Table 13 were synthesized by replacing N-(4-bromophenyl-)-N-phenyl-benzidine with starting material 7 shown in Table 13.
[0283] Table 13: Synthesis of compound CX
[0284] Mass spectrometry analysis was performed on some of the synthesized compounds, and the analytical results are shown in Table 14 below: Table 14: Mass spectra of compound CX
[0285] Fabrication and evaluation of organic electroluminescent devices: Example 1: Fabrication of a red organic electroluminescent device The anode pretreatment is first carried out through the following process: On ITO / Ag / ITO substrates with thicknesses of 100Å, 1000Å and 100Å respectively, the surface is treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate is cleaned with organic solvent to remove impurities and oil stains.
[0286] On the experimental substrate (anode), PD:HT-1 was co-deposited at a deposition rate of 2%:98% to form a hole injection layer (HIL) with a thickness of 100 Å. Then, HT-1 was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 1075 Å.
[0287] Compound HT-2 was vacuum-deposited onto the hole transport layer to form a hole conditioning layer with a thickness of 865 Å.
[0288] Next, on the hole adjustment layer, compound A2 was used as the first host, compound C22 as the second host, and RD-1 as the dopant, and a red light emitting layer was prepared by co-evaporation. Compound A2:compound C22:RD-1 were co-deposited at a deposition rate of 49%:49%:2% to form a red light emitting layer (EML) with a thickness of 420 Å.
[0289] On the light-emitting layer, compound ET-1 and LiQ are mixed in a 1:1 weight ratio and vapor-deposited to form a 350 Å thick electron transport layer (ETL). Yb is vapor-deposited on the electron transport layer to form a 10 Å thick electron injection layer (EIL). Then, magnesium (Mg) and silver (Ag) are mixed at a 1:9 vapor deposition rate and vacuum-deposited on the electron injection layer to form a 130 Å thick cathode.
[0290] In addition, a CP-1 layer with a thickness of 800 Å is vacuum-deposited on the cathode to form a capping layer, thereby completing the fabrication of the red organic electroluminescent device.
[0291] Examples 2-36 Except that the main light-emitting layer combination in Table 15 below is used instead of the combination of compounds A2 and C22 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.
[0292] Comparative Examples 1-3 Except that, when fabricating the light-emitting layer, the main combinations of the light-emitting layer in Table 15 below are used instead of the combination of compounds A2 and C22 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.
[0293] The compounds used in the preparation of the various examples and comparative examples have the following structures:
[0294] .
[0295] The performance of the red organic electroluminescent devices prepared in Examples 1-36 and Comparative Examples 1-3 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 15.
[0296] Table 15
[0297] As can be seen from Table 15 above, the organic electroluminescent device of the present invention uses two specific compounds as the main materials of the light-emitting layer, and compared with the device of the comparative example, the luminous efficiency is increased by at least 11.5% and the lifetime is increased by at least 12.9%.
[0298] Example 37: Fabrication of a red organic electroluminescent device The anode pretreatment is first carried out through the following process: On ITO / Ag / ITO substrates with thicknesses of 100Å, 1000Å and 100Å respectively, the surface is treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate is cleaned with organic solvent to remove impurities and oil stains.
[0299] On the experimental substrate (anode), PD:HT-5 was co-deposited at a deposition rate of 3%:97% to form a hole injection layer (HIL) with a thickness of 100 Å. Then, HT-5 was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 1025 Å.
[0300] Compound HT-1 was vacuum-deposited onto the hole transport layer to form a hole conditioning layer with a thickness of 890 Å.
[0301] Next, on the hole adjustment layer, compound A2 was used as the first host, compound B9 as the second host, and RD-1 as the dopant, and a red light emitting layer was prepared by co-evaporation. The first host and the second host were mixed uniformly at a weight ratio of 50:50 to obtain a composition; the composition of the host materials and RD-1 were simultaneously evaporated at a evaporation rate ratio of 97%:3% to form a red light emitting layer (EML) with a thickness of 400 Å.
[0302] On the light-emitting layer, compound ET-3 and LiQ are mixed in a 1:1 weight ratio and vapor-deposited to form a 350 Å thick electron transport layer (ETL). Yb is vapor-deposited on the electron transport layer to form a 10 Å thick electron injection layer (EIL). Then, magnesium (Mg) and silver (Ag) are mixed at a 1:8 vapor deposition rate and vacuum-deposited on the electron injection layer to form a 130 Å thick cathode.
[0303] Furthermore, CP-1 with a thickness of 800 Å is vacuum-deposited on the aforementioned cathode, thereby completing the fabrication of the red organic electroluminescent device.
[0304] Examples 37-45 Except that, when fabricating the light-emitting layer, the main combination of the light-emitting layer shown in Table 8 below is used instead of the combination of compounds A2 and B9 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 37.
[0305] Comparative Examples 4-5 Except that when fabricating the light-emitting layer, the combination of compounds A2 and B9 in Example 31 is replaced by the combination of light-emitting layer main components in Table 8 below, the organic electroluminescent device is prepared using the same method as in Example 31.
[0306] The compounds used in the preparation of the various examples and comparative examples have the following structures:
[0307] The performance of the red organic electroluminescent devices prepared in Examples 37-45 and Comparative Examples 4-5 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 16.
[0308] Table 16
[0309] As can be seen from Table 16 above, the organic electroluminescent device of the present invention uses two specific compounds as the main materials of the light-emitting layer, and compared with the device of the comparative example, the luminous efficiency is improved by at least 16.5% and the T95 lifetime is improved by at least 13.2%.
[0310] The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings. However, the present invention is not limited to the specific details of the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the protection scope of the present invention.
Claims
1. An organic electroluminescent device, comprising a cathode, an anode, and an organic layer; in, The cathode and the anode are arranged opposite to each other; The organic layer is located between the cathode and the anode; The organic layer includes an organic light-emitting layer; The organic light-emitting layer comprises a first compound and a second compound; The first compound has the structure shown in Formula 1: Formula 1 Z1, Z2 and Z3 are each independently selected from N or C(H), and at least one of Z1 to Z3 is N; Y is selected from S or O; One of X1 and X2 is -N=, and the other is O or S; Ring A is selected from naphthalene ring or phenanthrene ring; L1, L2, and L3 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L1, L2, L3, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each R1 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; n1 represents the number of R1; n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; The second compound has the structure shown in Formula 2 or Formula 3: Formula 2 One of X3 and X4 is -N=, and the other is O or S; L4, L5, and L6 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar4, Ar5, and Ar6 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L4, L5, L6, Ar4, Ar5, and Ar6 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each R2 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; n2 represents the number of R2; n2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; Formula 3 The C ring and the E ring are each independently selected from aromatic rings with 6 to 14 carbon atoms; L7 and L8 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar7 and Ar8 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in L7, L8, Ar7, and Ar8 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkoxy groups with 1 to 10 carbon atoms, alkylthio groups with 1 to 10 carbon atoms, aryloxy groups with 6 to 20 carbon atoms, or arylthio groups with 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring; Each of R3, R4, and R5 may be the same or different, and is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteratedalkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms; n3 represents the number of R3, n4 represents the number of R4, and n5 represents the number of R5; n3 and n5 are each independently selected from 0, 1, 2, 3, 4, 5, or 6; n4 is selected from 0, 1, or 2.
2. The organic electroluminescent device according to claim 1, wherein, The first compound is selected from the structures shown in 1-1 to 1-15 below: ; Where Y is O or S.
3. The organic electroluminescent device according to claim 1, wherein, In the first compound, Ar1, Ar2, and Ar3 are each independently selected from substituted or unsubstituted groups W1; the unsubstituted groups W1 are selected from the group consisting of: ; The substituted group W1 has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, benzoxazolyl, or benzothiazolyl. When the number of substituents on group W1 is greater than 1, the substituents may be the same or different.
4. The organic electroluminescent device according to claim 1, wherein, In the first compound, L1, L2 and L3 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted benzoxazolyl, and substituted or unsubstituted benzothiazolyl.
5. The organic electroluminescent device according to claim 1, wherein, The second compound is selected from the structures shown in formula (2-1), (2-2) or formulas (3-1) to (3-20): 。 6. The organic electroluminescent device according to claim 1, wherein, In Formula 2, Ar4, Ar5 and Ar6 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted benzimidazolyl.
7. The organic electroluminescent device according to claim 1, wherein, In Formula 2, L4, L5 and L6 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthracene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl.
8. The organic electroluminescent device according to claim 1, wherein, In Formula 1, each R1 may be the same or different, and each is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or carbazoyl.
9. The organic electroluminescent device according to claim 1, wherein, In Formula 3, L7 and L8 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted anthracene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl.
10. The organic electroluminescent device according to claim 1, wherein, In Formula 3, Ar7 and Ar8 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted benzimidazolyl, and substituted or unsubstituted pyridyl.
11. The organic electroluminescent device according to claim 1, wherein, In the first compound, and Each is independently selected from the following groups: 。 12. The organic electroluminescent device according to claim 1, wherein, The organic light-emitting layer comprises a host material and a dopant. The host material includes a first compound and a second compound. The mass ratio of the first compound and the second compound is 30:70 to 70:
30.
13. The organic electroluminescent device according to claim 1, wherein, The first compound is selected from the group consisting of the following compounds: 。 14. The organic electroluminescent device according to claim 1, wherein, Any two adjacent R4s form a loop.
15. The organic electroluminescent device according to claim 4, wherein, The substituents in L1, L2, and L3 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, or phenyl.
16. The organic electroluminescent device according to claim 6, wherein, The substituents in Ar4, Ar5 and Ar6 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl or carbazoyl. Optionally, in Ar4 and Ar5, any two adjacent substituents form a benzene ring.
17. The organic electroluminescent device according to claim 7, wherein, The substituents in L4, L5, and L6 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, or phenyl.
18. The organic electroluminescent device according to claim 8, wherein, In Formula 2, each R2 may be the same or different, and each is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl.
19. The organic electroluminescent device according to claim 8, wherein, In Formula 3, each of R3, R4 and R5 may be the same or different, and each is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
20. The organic electroluminescent device according to claim 9, wherein, The substituents in L7 and L8 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, or phenyl.
21. The organic electroluminescent device according to claim 10, wherein, The substituents in Ar7 and Ar8 are each independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl. Optionally, any two adjacent substituents in Ar7 and Ar8 form a benzene ring.
22. The organic electroluminescent device according to claim 11, wherein, In Equation 2, and Each is independently selected from the following groups: 。 23. The organic electroluminescent device according to claim 11, wherein, In Equation 3, and Each is independently selected from the following groups: 。 24. The organic electroluminescent device according to claim 13, wherein, The second compound is selected from the group consisting of the following compounds: The second compound shown in Formula 3 is selected from the following structures: 。 25. An electronic device, characterized in that, Includes the organic electroluminescent device according to any one of claims 1 to 24.
Citation Information
Patent Citations
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