An organic electroluminescent compound and an organic electroluminescent device comprising the same

Abstract

The application relates to an organic electroluminescent compound and an organic electroluminescent device containing the same, the structural formula of the organic electroluminescent compound is as follows: the organic electroluminescent device can effectively reduce a driving voltage and improve a service life.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and in particular to an organic electroluminescent compound and an organic electroluminescent device comprising the same. Background Technology

[0002] Organic light-emitting diodes (OLEDs) convert electrical energy into light by applying electricity to organic light-emitting materials, and typically consist of an anode, a cathode, and an organic layer formed between these two electrodes. The organic layer of an OLED can include hole injection layers, hole transport layers, hole auxiliary layers, light-emitting auxiliary layers, electron blocking layers, light-emitting layers (containing host materials and dopant materials), electron buffer layers, hole blocking layers, electron transport layers, and electron injection layers, etc. Based on the functions achieved by each layer, the various materials used in the organic layer are categorized as hole injection materials, hole transport materials, hole auxiliary materials, light-emitting auxiliary materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, and electron injection materials, etc. In an OLED, holes from the anode and electrons from the cathode are injected into the light-emitting layer by applying a voltage, and high-energy excitons are generated through the recombination of holes and electrons. The organic light-emitting compound moves to an excited state by energy and emits light by the energy when the organic light-emitting compound returns from the excited state to the ground state.

[0003] Existing organic electroluminescent materials suffer from poor structural stability and poor matching between their HOMO and LUMO energy levels and adjacent energy levels, resulting in low stability and unbalanced carrier mobility. This further leads to higher driving voltages, lower luminous efficiency, and shorter lifetimes in organic electroluminescent devices incorporating these materials, severely limiting their applications. Summary of the Invention

[0004] The purpose of this invention is to overcome the problems of poor structural stability of existing organic electroluminescent materials and poor matching degree between the HOMO and LUMO energy levels and adjacent energy levels of existing organic electroluminescent materials, which leads to low stability and unbalanced carrier mobility of organic electroluminescent materials. This results in high driving voltage, low luminous efficiency and short lifetime of organic electroluminescent devices containing such organic electroluminescent materials, which seriously limits the application of organic electroluminescent devices. Therefore, this invention provides an organic electroluminescent compound and its application.

[0005] The technical solution adopted by the present invention to solve at least one of the above-mentioned technical problems is: an organic electroluminescent compound with the following structural formula:

[0006]

[0007] Among them, Q1, Q2, Q3, and Q4 are the same or different, and each is independently a substituted or unsubstituted C6-C60 aromatic ring or a substituted or unsubstituted C6-C60 aromatic heterocycle.

[0008] X is selected from O, S, NR 6 CR 7 R 8 ;

[0009] Among them, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 The same or different, and each independently selected from hydrogen, deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 heterocycloalkyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C1-C60 alkylthio, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C4-C60 heteroaryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C4-C60 heteroaryloxy;

[0010] a, b, c, and d may be the same or different, and each may be an independent integer selected from 0 to 7; e may be an integer selected from 0 to 3; for example, when a is an integer greater than or equal to 2, the corresponding multiple substituents R1 may be the same or different.

[0011] The substituents in the substituted C6-C60 aromatic ring, substituted C6-C60 aromatic heterocyclic ring, substituted C1-C60 alkyl, substituted C3-C60 cycloalkyl, substituted C2-C60 heterocyclic alkyl, substituted C1-C60 alkoxy, substituted C1-C60 alkylthio, substituted C6-C60 aryl, substituted C4-C60 heteroaryl, substituted C6-C60 aryloxy, and substituted C4-C60 heteroaryloxy are selected from deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, C1-C60 alkyl, C3-C60 cycloalkyl, C2-C60 heterocyclic alkyl, C1-C60 alkoxy, C1-C60 alkylthio, C6-C60 aryl, C4-C60 heteroaryl, C6-C60 aryloxy, and C4-C60 heteroaryloxy.

[0012] Preferably, Q1, Q2, Q3, and Q4 are the same or different, and each is independently selected from substituted or unsubstituted C6-C50 aromatic rings or substituted or unsubstituted C6-C50 aromatic heterocycles.

[0013] The substituents in the substituted C6-C50 aromatic ring or the substituted C6-C50 aromatic heterocycle are selected from deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, C1-C50 alkyl, C3-C50 cycloalkyl, C2-C50 heterocycloalkyl, C1-C50 alkoxy, C1-C50 alkylthio, C6-C50 aryl, C4-C50 heteroaryl, C6-C50 aryloxy, and C4-C50 heteroaryloxy.

[0014] Preferably, Q1, Q2, Q3, and Q4 are the same or different, and each is independently selected from substituted or unsubstituted C6-C25 aromatic rings or substituted or unsubstituted C6-C25 aromatic heterocycles.

[0015] The substituents in the substituted C6-C25 aromatic ring or the substituted C6-C25 aromatic heterocycle are selected from deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C2-C25 heterocycloalkyl, C1-C25 alkoxy, C1-C25 alkylthio, C6-C25 aryl, C4-C25 heteroaryl, C6-C25 aryloxy, and C4-C25 heteroaryloxy.

[0016] Preferably, Q1, Q2, Q3, and Q4 are the same or different, and each is independently selected from substituted or unsubstituted group D. Group D is selected from one or more of phenyl, biphenyl, terphenyl, pyridyl, benzothiophene, benzofuranyl, naphthothiophene, naphthofuranyl, carbazothiophene, carbazofuranyl, fluorenyl, fluorenyl, fluorenyl, fluorenylfuranyl, naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, dihydroanthraphene, dimethylfluorenyl, dihydroanthraphene, dihydroanthraphene, dihydronaphthofuranyl, tetrahydronaphthyl, dihydronaphthyl, carbazoyl, dibenzothiophene, dibenzofuranyl, and triphenylamino.

[0017] The substituents in the substituted gene D are selected from deuterium, carboxyl, nitro, cyano, amino, halogen, trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfuranylsilyl, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexyl Methyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylisopropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, spirodel, spiroundecyl, adamantyl, methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentoxy, isopentoxy, hexoxy, azircyclopropane, pyrrolidine, piperidine, azircycloheptane, azircycloheptane.

[0018] Preferably, two of Q1, Q2, Q3, and Q4 are selected from substituted or unsubstituted fluorene groups;

[0019] The substituents in the substituted fluorene group are selected from one or more of deuterium, carboxyl, nitro, cyano, amino, halogen, and silyl groups.

[0020] Preferably, formula I is selected from one of the following structures: formula (1-1) to formula (1-6):

[0021]

[0022]

[0023] Preferably, the R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8The same or different, and each independently selected from hydrogen, deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, substituted or unsubstituted C1-C50 alkyl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C2-C50 heterocycloalkyl, substituted or unsubstituted C1-C50 alkoxy, substituted or unsubstituted C1-C50 alkylthio, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C4-C50 heteroaryl, substituted or unsubstituted C6-C50 aryloxy, substituted or unsubstituted C4-C50 heteroaryloxy, and

[0024] The substituents in the substituted C1-C50 alkyl, substituted C3-C50 cycloalkyl, substituted C2-C50 heterocycloalkyl, substituted C1-C50 alkoxy, substituted C1-C50 alkylthio, substituted C6-C50 aryl, substituted C4-C50 heteroaryl, substituted C6-C50 aryloxy, and substituted C4-C50 heteroaryloxy groups are selected from deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, C1-C50 alkyl, C3-C50 cycloalkyl, C2-C50 heterocycloalkyl, C1-C50 alkoxy, C1-C50 alkylthio, C6-C50 aryl, C4-C50 heteroaryl, C6-C50 aryloxy, and C4-C50 heteroaryloxy groups.

[0025] Preferably, the R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 The same or different, and each independently selected from hydrogen, deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C2-C25 heterocycloalkyl, substituted or unsubstituted C1-C25 alkoxy, substituted or unsubstituted C1-C25 alkylthio, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C4-C25 heteroaryl, substituted or unsubstituted C6-C25 aryloxy, substituted or unsubstituted C4-C25 heteroaryloxy, and

[0026] The substituents in the substituted C1-C25 alkyl, substituted C3-C25 cycloalkyl, substituted C2-C25 heterocycloalkyl, substituted C1-C25 alkoxy, substituted C1-C25 alkylthio, substituted C6-C25 aryl, substituted C4-C25 heteroaryl, substituted C6-C25 aryloxy, and substituted C4-C25 heteroaryloxy groups are selected from deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C2-C25 heterocycloalkyl, C1-C25 alkoxy, C1-C25 alkylthio, C6-C25 aryl, C4-C25 heteroaryl, C6-C25 aryloxy, and C4-C25 heteroaryloxy groups.

[0027] Preferably, the R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 The same or different, and each independently selected from hydrogen, deuterium, carboxyl, nitro, cyano, amino, halogen, trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfuranylsilyl, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl The group consisting of octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylisopropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, spirodel, spiroundecyl, adamantyl, methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentoxy, isopentoxy, hexoxy, azircyclopropane, pyrrolidine, piperidine, azircycloheptane, or the following groups:

[0028]

[0029] Preferably, a, b, c, and d are the same or different, and each is an independent integer selected from 0 to 6;

[0030] Preferably, a, b, c, and d are the same or different, and each is an independent integer selected from 0 to 5;

[0031] Preferably, a, b, c, and d are the same or different, and each is an independent integer selected from 0 to 4;

[0032] Preferably, a, b, c, and d are the same or different, and each is an independent integer selected from 0 to 3;

[0033] Preferably, a, b, c, and d are the same or different, and each is an independent integer selected from 0 to 2;

[0034] Preferably, a, b, c, and d are the same or different, and each is an independent integer selected from 0 to 1;

[0035] Preferably, e is selected from integers from 0 to 2;

[0036] Preferably, e is selected from integers from 0 to 1.

[0037] Preferably, formula I is selected from one of the following structures: formulas B-1 to B-136.

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045] An organic electroluminescent material comprising the aforementioned organic electroluminescent compound.

[0046] An organic electroluminescent device includes a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer between the first electrode and the second electrode, wherein the organic layer comprises the aforementioned organic electroluminescent compound or the aforementioned organic electroluminescent material.

[0047] Preferably, the organic layer includes a light-emitting layer, which includes the above-described organic electroluminescent compound or the above-described organic electroluminescent material.

[0048] Application of the above-mentioned organic electroluminescent device in optical fiber equipment, lighting equipment, electrophotographic photosensitive equipment, photoelectric converters, organic solar cells, switching element equipment, organic light-emitting field-effect transistors, image sensors or dye lasers.

[0049] Compared with the prior art, the advantages of the present invention are as follows: the organic electroluminescent compound provided by the present invention can be matched to the corresponding level in the organic electroluminescent device, effectively reducing the driving voltage, current efficiency and extending the device lifetime; based on the structure of Formula I, further limiting the types of substituents can improve the structural stability of the compound, and the HOMO and LUMO energy levels of the electroluminescent compound have a high degree of matching with adjacent energy levels, so that the organic electroluminescent compound obtains high stability and relatively balanced carrier mobility, thereby making the organic electroluminescent device containing the electroluminescent compound have a better lifetime, while also having a lower driving voltage and higher efficiency. Attached Figure Description

[0050] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device in an embodiment of the present invention;

[0051] In this design, 1 is the substrate, 2 is the anode, 3 is the hole injection layer, 4 is the hole transport layer, 5 is the light-emitting layer, 6 is the electron transport layer, 7 is the electron injection layer, and 8 is the cathode. Detailed Implementation

[0052] The present invention will be further described in detail below with reference to the accompanying drawings and embodiments.

[0053] As used in this invention, the term "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent element and may include at least one compound. If desired, the organic electroluminescent material may be included in any layer constituting the organic electroluminescent element. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, an electron blocking material, a light-emitting auxiliary material, a light-emitting layer material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0054] In this invention, the term "substituent" has its usual meaning as known in the art, referring to a chemical moiety covalently attached to or, where appropriate, fused to a parent nucleus group.

[0055] In this invention, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The substituents mentioned above, namely Rc, can be, for example, deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, or C4-C60 heteroaryl. Of course, the number of substituents Rc can be one or more. When two substituents Rc are attached to the same atom, these two substituents Rc can exist independently (independent existence means that Rc can take the same group or different groups) or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent substituents Rc can exist independently or fuse with the functional group to which they are attached to form a ring.

[0056] In this invention, C1-C60, C3-C60, and C6-C60 define the range of carbon atoms, and the number of carbon atoms is any integer within the defined range. For example, C6-C60 aryl means that the number of carbon atoms representing the aryl group can be any integer within the range of 6-60, such as 6, 9, 14, 17, 21, 27, 31, 35, 44, 47, 54, 59, and 60.

[0057] In this invention, the term "silyl" refers to unsubstituted silyl (-SiH3) or substituted silyl (-SiH2R,-SiHR2,-SiR3), wherein R can be alkyl, aryl, heteroaryl, etc., and examples include, but are not limited to, trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfuranylsilyl, etc.

[0058] In this invention, the term "alkyl" refers, whether as part of other terms or used alone, to a saturated hydrocarbon group, which may be straight-chain or branched. The term "C1-C60 alkyl" is derived from a monovalent substituent of a straight-chain or branched saturated hydrocarbon having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms. Examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1 -Methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylisopropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc.

[0059] In this invention, the term "cycloalkyl" refers to a cyclic alkyl group consisting of at least 3 carbon atoms. Further, C3-C60 cycloalkyl refers to a monocyclic or polycyclic hydrocarbon derived from a main cyclic chain having 3 to 60 carbon atoms, preferably 3 to 40 carbon atoms, and even more preferably 3 to 20 carbon atoms. Of course, the cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, spirodecyl, spiroundecyl, adamantyl, etc.

[0060] In this invention, the term "alkoxy" specifically includes, but is not limited to, phenoxy, p-toluoxy, m-toluoxy, 3,5-dimethylphenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenoxy, 4-biphenoxy, 1-naphthoxy, 2-naphthoxy, 4-methyl-1-naphthoxy, 5-methyl-2-naphthoxy, 1-anthraoxy, 2-anthraoxy, 9-anthraoxy, 1-phenanthoxy, 3-phenanthoxy, and 9-phenanthoxy.

[0061] In this invention, the term "alkoxide" specifically includes, but is not limited to, phenylthiol, p-toluenethiol, m-toluenethiol, 3,5-dimethylphenylthiol, 2,4,6-trimethylphenylthiol, p-tert-butylphenylthiol, 3-biphenylthiol, 4-biphenylthiol, 1-naphthylthiol, 2-naphthylthiol, 4-methyl-1-naphthylthiol, 5-methyl-2-naphthylthiol, 1-anthrathiol, 2-anthrathiol, 9-anthrathiol, 1-phenanthrenethiol, 3-phenanthrenethiol, and 9-phenanthrenethiol.

[0062] In this invention, the term "heterocyclic alkyl" refers to an aromatic or non-aromatic cyclic group containing one or more heteroatoms, wherein the one or more heteroatoms are O, S, N, P, B, Si, and Se, preferably selected from O, N, or S. Specifically, if N is present, it can be azircyclopropane, pyrrolidine, piperidine, azircycloheptane, azircycloheptane, etc., and also includes monocyclic or polycyclic compounds, and can be substituted by other substituents.

[0063] In this invention, the term "aromatic ring" or "aryl" includes monocyclic, polycyclic, or fused-ring aryl groups, which may be interrupted by short non-aromatic units and may contain spiro structures. Aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, spirodifluorenyl, etc.

[0064] In this invention, the term "aromatic heterocycle" or "heteroaryl" refers to an aromatic ring containing a heteroatom, such as thiophene, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazole, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiaphene, benzofuranyl, dibenzofuranyl, phenanthrololinyl, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, and benzothiazolyl. However, it is not limited to these.

[0065] In this invention, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0066] In this invention, unless otherwise stated, hydrogen atoms include protium, deuterium, and tritium.

[0067] In this invention, the organic electroluminescent compound having the structure of Formula I is prepared via the following synthetic route:

[0068]

[0069] For experiments not specifically described in the examples, the procedures or conditions should be followed according to the conventional experimental procedures described in the literature in this field. Reagents or instruments whose manufacturers are not specified are all commercially available conventional reagent products.

[0070] Those skilled in the art will recognize that the chemical reactions described in this invention can be suitably used to prepare many of the heterocyclic compounds of this invention, and other methods for preparing the compounds of this invention are considered to be within the scope of this invention. For example, the synthesis of those non-illustrative compounds according to this invention can be successfully accomplished by those skilled in the art through modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents besides those described in this invention, or by making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this invention are commercially available starting materials.

[0071] Synthesis of intermediate B1-a:

[0072]

[0073] (1) Preparation of intermediate b1-a-1

[0074] Under nitrogen protection, in a 500 mL four-necked flask, compound b-a1 (100 mmol), compound b-b1 (100 mmol), Pd(dppf)Cl2CH2Cl2 (1 mmol), and potassium carbonate (200 mmol) were dissolved in a mixture of 240 mL toluene and 50 mL water at room temperature. The reaction was quenched by reflux and stirring at 90 °C for 2 hours. After extraction with dichloromethane, the intermediate b1-a-1 was obtained by column chromatography (yield 85%).

[0075] (2) Preparation of intermediate b1-a-2

[0076] Under nitrogen protection, compound b1-a-1 (80 mmol) was dissolved in 150 mL of methanesulfonic acid in a 500 mL four-necked flask at room temperature. After stirring at 105 °C for 8 hours, the mixture was cooled to room temperature and quenched with water. The pH was adjusted to neutral, and the mixture was extracted with dichloromethane and then subjected to column chromatography to obtain intermediate b1-a-2 (yield 90%).

[0077] (3) Preparation of intermediate b1-a-3

[0078] Under nitrogen protection, compound b1-a-2 (65 mmol) was dissolved in 100 mL of dichloromethane in a 500 mL four-necked flask at room temperature. 100 mL of acetic acid was added, followed by the addition of 11.6 g of NBS. After stirring at room temperature for 2 hours, the pH was adjusted to neutral with a large amount of sodium bicarbonate aqueous solution. After extraction with dichloromethane, the intermediate compound b1-a-3 was obtained by column chromatography (yield 80%).

[0079] (4) Preparation of intermediate b1-a-4

[0080] Under nitrogen protection, compound b1-a-3 (50 mmol) was dissolved in 180 mL of dichloromethane in a 500 mL four-necked flask. After cooling to 0 °C, 9.5 g (100 mmol) of 1,2-ethanedithiol and 180 mL of boron trifluoride diethyl ether solution were slowly added dropwise. After stirring at room temperature for 6 hours, the mixture was quenched and washed with a large amount of saturated saline solution. After extraction with dichloromethane, the intermediate compound b1-a-4 was obtained by column chromatography (yield 80%).

[0081] (5) Preparation of intermediate B1-a

[0082] Under nitrogen protection, 150 mL of dichloromethane and 200 mmol of NIS were added dropwise to 120 mL of pyridine hydrogen fluoride in a 500 mL four-necked flask at 0 °C. After stirring at this temperature for 20 min, a solution of compound b1-a-4 (40 mmol) and 180 mL of dichloromethane was slowly added dropwise to the system. The reaction was quenched after stirring at room temperature for 2 hours. The mixture was then extracted with dichloromethane and subjected to column chromatography to obtain intermediate B1-a (yield 90%).

[0083] B12-a was synthesized using the same method as intermediate B1-a, except that starting material b-a1 was replaced by starting material b-a12. The specific synthetic route is shown below:

[0084]

[0085] B12-a was obtained with a yield of 89%.

[0086] Synthesis of intermediate B1-b:

[0087]

[0088] (1) Preparation of intermediate b1-b-1

[0089] Under nitrogen protection, in a 500 mL four-necked flask, compounds c1-a (100 mmol), d1-b (100 mmol), Pd2(dba)3 (1 mmol), and potassium carbonate (200 mmol) were dissolved in a mixture of 240 mL toluene and 50 mL water at room temperature. The reaction was quenched by reflux and stirring at 90 °C for 2 hours. After extraction with dichloromethane, the intermediate compound b1-b-1 was obtained by column chromatography (yield 83%).

[0090] (2) Preparation of intermediate b1-b-2

[0091] Under nitrogen protection, compound b1-b-1 (80 mmol) was dissolved in 150 mL of methanesulfonic acid in a 500 mL four-necked flask at room temperature. After stirring at 105 °C for 8 hours, the mixture was cooled to room temperature and quenched with water. The pH was adjusted to neutral, and the mixture was extracted with dichloromethane and then subjected to column chromatography to obtain intermediate compound b1-b-2 (yield 90%).

[0092] (3) Preparation of intermediate b1-b-3

[0093] Under nitrogen protection, compound b1-b-2 (65 mmol) was dissolved in 180 mL of dichloromethane in a 500 mL four-necked flask at room temperature. After cooling to 0 °C, 9.5 g (100 mmol) of 1,2-ethanedithiol and 180 mL of boron trifluoride diethyl ether solution were slowly added dropwise. After stirring at room temperature for 6 hours, the mixture was quenched and washed with a large amount of saturated saline solution. After extraction with dichloromethane, the intermediate compound b1-b-3 was obtained by column chromatography (yield 82%).

[0094] (4) Preparation of intermediate b1-b-4

[0095] Under nitrogen protection, 150 mL of dichloromethane and 45 g (200 mmol) of NIS were added dropwise to 120 mL of pyridine hydrogen fluoride in a 500 mL four-necked flask at 0 °C. After stirring at this temperature for 20 min, a solution of compound b1-b-3 (40 mmol) and 180 mL of dichloromethane was slowly added dropwise to the system. The reaction was quenched after stirring at room temperature for 2 hours. After extraction with dichloromethane, the intermediate b1-b-4 was obtained by column chromatography (yield 82%).

[0096] (5) Preparation of intermediate B1-b

[0097] Under nitrogen protection, in a 1000 mL four-necked flask, Pd[P(o-tol)3]2 (0.15 mmol) and CyPF-t-Bu (0.15 mmol), sodium tert-butoxide (60 mmol), intermediate b1-b-4 (30 mmol), and liquid ammonia (300 mL 0.5 M dioxane solution) were added to 100 mL of dioxane. The mixture was kept sealed and heated to 80 °C, then stirred for 3 h. After quenching the reaction, the mixture was extracted with dichloromethane and then subjected to column chromatography to obtain intermediate B1-b (70% yield).

[0098] B58-b, B73-b, and B89-b were synthesized using the same method as intermediate B1-b, with the difference being the substitution of the corresponding raw materials. For details of the raw material substitutions, please refer to Table 1.

[0099] Table 1 List of Raw Materials and Products

[0100]

[0101] Synthesis of intermediate B19-d:

[0102]

[0103] In a 500 mL three-necked flask under nitrogen protection, compound B73-b (29.55 mmol), compound e19-a (13.40 mmol), 120 mL of toluene, tris(dibenzylacetone)palladium (0.068 mmol), sodium tert-butoxide (33.00 mmol), and 4,5-bis(diphenylphosphine-9,9-dimethyloxanthracene) (0.14 mmol) were added. The reaction was carried out overnight at 100 °C. After the reaction was completed, water was added to quench the reaction, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate to remove the organic solvent. The crude product was recrystallized from o-dichlorobenzene to give compound B19-d (yield 71%).

[0104] B26-d, B73-d, B104-d, B118-d, and B126-d were synthesized using the same method as intermediate B19-d, with the difference being the substitution of the corresponding raw materials. For details of the raw material substitutions, please refer to Table 2.

[0105] Table 2 List of Raw Materials and Products

[0106]

[0107]

[0108] Synthesis of intermediate B72-d:

[0109]

[0110] (1) Preparation of intermediate b72-d-1

[0111] Under nitrogen protection, in a 500 mL four-necked flask, compound c58-a (100 mmol), compound d73-b (100 mmol), Pd2(dba)3 (1 mmol), and potassium carbonate (200 mmol) were dissolved in a mixture of 240 mL toluene and 50 mL water at room temperature. The reaction was quenched by reflux and stirring at 90 °C for 2 hours. After extraction with dichloromethane, the intermediate compound b72-d-1 was obtained by column chromatography (yield 82%).

[0112] (2) Preparation of intermediate b72-d-2

[0113] Under nitrogen protection, compound b72-d-1 (80 mmol) was dissolved in 150 mL of methanesulfonic acid in a 500 mL four-necked flask at room temperature. After stirring at 105 °C for 8 hours, the mixture was cooled to room temperature and quenched with water. The pH was adjusted to neutral, and the mixture was extracted with dichloromethane and then subjected to column chromatography to obtain intermediate compound b72-d-2 (yield 91%).

[0114] (3) Preparation of intermediate b72-d-3

[0115] Under nitrogen protection, compound b72-d-2 (65 mmol) was dissolved in 180 mL of dichloromethane in a 500 mL four-necked flask at room temperature. After cooling to 0 °C, 9.5 g (100 mmol) of 1,2-ethanedithiol and 180 mL of boron trifluoride diethyl ether solution were slowly added dropwise. After stirring at room temperature for 6 hours, the mixture was quenched and washed with a large amount of saturated saline solution. After extraction with dichloromethane, the intermediate compound b72-d-3 was obtained by column chromatography (yield 81%).

[0116] (4) Preparation of intermediate b72-d-4

[0117] Under nitrogen protection, 150 mL of dichloromethane and 45 g (200 mmol) of NIS were added dropwise to 120 mL of pyridine hydrogen fluoride in a 500 mL four-necked flask at 0 °C. After stirring at this temperature for 20 min, a solution of compound b72-d-3 (40 mmol) and 180 mL of dichloromethane was slowly added dropwise to the system. The reaction was quenched after stirring at room temperature for 2 hours. After extraction with dichloromethane, the intermediate b72-d-4 was obtained by column chromatography (yield 83%).

[0118] (5) Preparation of intermediate B72-d

[0119] In a 500 mL three-necked flask under nitrogen protection, compound B89-b (29.55 mmol), compound b72-d-4 (13.40 mmol), 120 mL of toluene, tris(dibenzylacetone)palladium (0.068 mmol), sodium tert-butoxide (33.00 mmol), and 4,5-bis(diphenylphosphine-9,9-dimethyloxanthracene) (0.14 mmol) were added. The reaction was carried out overnight at 100 °C. After the reaction was completed, water was added to quench the reaction, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate to remove the organic solvent. The crude product was recrystallized from o-dichlorobenzene to give compound B72-d (70% yield).

[0120] Synthesis Example 1

[0121] This embodiment provides the synthesis of compound B-1, and the specific synthetic route is shown below:

[0122]

[0123] (1) Preparation of intermediate B1-1

[0124] Under nitrogen protection, in a 250 mL four-necked flask, 8.6 g (22 mmol) of compound B1-a, 4.8 g (22 mmol) of compound B1-b, 0.4 g (0.44 mmol) of Pd2(dba)3, 0.6 g (1.32 mmol) of X-phos, and 6.3 g (66 mmol) of sodium tert-butoxide were dissolved in 100 mL of toluene at room temperature. The mixture was refluxed at 100 °C and stirred for 6 hours. The reaction was quenched with water, and the mixture was extracted with dichloromethane and then subjected to column chromatography to give 9.9 g of intermediate compound B1-1 (yield 86%).

[0125] (2) Preparation of intermediate B1-2

[0126] Under nitrogen protection, 6.4 g (12 mmol) of intermediate B1-1, 2.7 g (12 mmol) of compound B1-c, 0.23 g (0.24 mmol) of Pd2(dba)3, 0.2 g (0.36 mmol) of X-phos, and 2.9 g (30 mmol) of sodium tert-butoxide were added to 100 mL of toluene in a 250 mL three-necked flask. The mixture was refluxed at 100 °C and stirred for 3 hours. The reaction was quenched with water, extracted with dichloromethane, and then subjected to column chromatography to obtain 6.9 g of intermediate compound B1-2 (yield 85%).

[0127] (3) Preparation of intermediate B1-3

[0128] Under nitrogen protection, 5.2 g (10 mmol) of intermediate B1-2, 5.2 g (12 mmol) of compound B1-d, 0.20 g (0.2 mmol) of Pd2(dba)3, 0.15 g (0.30 mmol) of X-phos, and 2.9 g (30 mmol) of sodium tert-butoxide were added to a 250 mL three-necked flask and dissolved in 100 mL of toluene. The mixture was refluxed at 100 °C and stirred for 3 hours. The reaction was quenched with water, extracted with dichloromethane, and then subjected to column chromatography to obtain 8.8 g of intermediate compound B1-3 (yield 76%).

[0129] (4) Preparation of compound B-1

[0130] Under nitrogen protection, 8.1 g (7 mmol) of starting material B1-3 and 40 mL of anhydrous tert-butylbenzene were added to a 100 mL three-necked flask. After cooling to -60 °C, a pentane solution of tert-butyllithium (12 mL, 1.3 M, 15 mmol) was slowly added dropwise. The temperature was then raised to -30 °C and the reaction was carried out for 2 hours. Boron tribromide (15 mL, 1.0 M, 15 mmol) was then slowly added and the mixture was stirred for another 2 hours. N,N-diisopropylethylamine (2 g, 15 mmol) was then slowly added while maintaining the temperature. The temperature was raised to 120 °C and the reaction was continued for 5 hours. After cooling to room temperature, the solvent was evaporated under vacuum, and column chromatography yielded 2.8 g of yellow solid B-1 (yield 36%).

[0131] Elemental analysis: C 76 H 62 BF4N3S. Theoretical values: C, 80.34; H, 5.50; B, 0.95; F, 6.69; N, 3.70; S, 2.82; Measured values: C, 80.36; H, 5.51; B, 0.94; F, 6.68; N, 3.68; S, 2.83.

[0132] HRMS(ESI)m / z[M+H]+: Theoretical value: 1135.47; Measured value: 1136.34.

[0133] Synthesis Example 2

[0134] Compound B-7 was synthesized using the same method as in Example 1, except that starting material B1-c was replaced with starting material B7-c. The specific synthetic route is shown below:

[0135]

[0136] Compound B-7 was obtained in 38% yield. Elemental analysis: C80H70BF4N3S. Theoretical values: C, 80.59; H, 5.92; B, 0.91; F, 6.37; N, 3.52; S, 2.69; Found values: C, 80.62; H, 5.93; B, 0.90; F, 6.36; N, 3.51; S, 2.68.

[0137] HRMS(ESI)m / z[M+H]+: Theoretical value: 1191.53; Measured value: 1192.24.

[0138] Synthesis Example 3

[0139] Compound B-12 was synthesized using the synthetic method of Example 1, except that starting material B12-a was used instead of starting material B1-a and starting material B7-c was used instead of starting material B1-c. The specific synthetic route is shown below:

[0140]

[0141] Compound B-12 was obtained in 41% yield. Elemental analysis: C 90 H 82 BF4N3S. Theoretical values: C, 81.61; H, 6.24; B, 0.82; F, 5.74; N, 3.17; S, 2.42; Measured values: C, 81.63; H, 6.25; B, 0.81; F, 5.73; N, 3.15; S, 2.43.

[0142] HRMS(ESI)m / z[M+H]+: Theoretical value: 1323.63; Measured value: 1324.61.

[0143] Synthesis Example 4

[0144] Compound B-19 was synthesized using the synthetic method of Example 1, except that starting material B19-b was used instead of starting material B1-b, starting material B7-c was used instead of starting material B1-c, and starting material B19-d was used instead of starting material B1-d. The specific synthetic route is shown below:

[0145]

[0146] Compound B-19 was obtained in 44% yield. Elemental analysis: C 62 H 57 BF4N2S. Theoretical values: C, 78.47; H, 6.05; B, 1.14; F, 8.01; N, 2.95; S, 3.38; Measured values: C, 78.49; H, 6.07; B, 1.13; F, 8.00; N, 2.94; S, 3.37.

[0147] HRMS(ESI)m / z[M+H]+: Theoretical value: 948.43; Measured value: 949.33.

[0148] Synthesis Example 5

[0149] Compound B-26 was synthesized using the same method as in Example 1, except that starting material B19-b was used instead of starting material B1-b, starting material B7-c was used instead of starting material B1-c, and starting material B26-d was used instead of starting material B1-d. The specific synthetic route is shown below:

[0150]

[0151] Compound B-26 was obtained in 46% yield. Elemental analysis: C 66 H 65BF4N2S. Theoretical values: C, 78.87; H, 6.52; B, 1.08; F, 7.56; N, 2.79; S, 3.19; Measured values: C, 78.88; H, 6.53; B, 1.09; F, 7.57; N, 2.77; S, 3.17.

[0152] HRMS(ESI)m / z[M+H]+: Theoretical value: 1004.49; Measured value: 1005.51.

[0153] Synthesis Example 6

[0154] Compound B-42 was synthesized using the synthetic method of Example 1, except that starting material B42-a replaced starting material B1-a, starting material B19-b replaced starting material B1-b, and starting material B19-d replaced starting material B1-d. The specific synthetic route is shown below:

[0155]

[0156] Compound B-42 was obtained in 45% yield. Elemental analysis: C 60 H 45 BF4N2S. Theoretical values: C, 78.94; H, 4.97; B, 1.18; F, 8.32; N, 3.07; S, 3.51; Measured values: C, 78.96; H, 4.99; B, 1.17; F, 8.31; N, 3.06; S, 3.50.

[0157] HRMS(ESI)m / z[M+H]+: Theoretical value: 912.33; Measured value: 913.45.

[0158] Synthesis Example 7

[0159] Compound B-49 was synthesized using the same method as in Example 1, except that starting material B49-a replaced starting material B1-a, starting material B7-c replaced starting material B1-c, and starting material B19-d replaced starting material B1-d. The specific synthetic route is shown below:

[0160]

[0161] Compound B-49 was obtained in 42% yield. Elemental analysis: C 58 H 49 BF4N2S. Theoretical values: C, 78.02; H, 5.53; B, 1.21; F, 8.51; N, 3.14; S, 3.59; Measured values: C, 78.04; H, 5.55; B, 1.20; F, 8.52; N, 3.12; S, 3.57.

[0162] HRMS(ESI)m / z[M+H]+: Theoretical value: 892.36; Measured value: 893.21.

[0163] Synthesis Example 8

[0164] Compound B-58 was synthesized using the synthetic method of Example 1, except that reactant B49-a replaced reactant B1-a, reactant B58-b replaced reactant B1-b, reactant B7-c replaced reactant B1-c, and reactant B26-d replaced reactant B1-d. The specific synthetic route is shown below:

[0165]

[0166] Compound B-58 was obtained in 43% yield. Elemental analysis: C 66 H 65 BF4N2S. Theoretical values: C, 78.87; H, 6.52; B, 1.08; F, 7.56; N, 2.79; S, 3.19; Measured values: C, 78.89; H, 6.54; B, 1.09; F, 7.55; N, 2.77; S, 3.17.

[0167] HRMS(ESI)m / z[M+H]+: Theoretical value: 1004.49; Measured value: 1005.31.

[0168] Synthesis Example 9

[0169] Compound B-72 was synthesized using the synthetic method of Example 1, except that reactant B49-a replaced reactant B1-a, reactant B19-b replaced reactant B1-b, reactant B72-c replaced reactant B1-c, and reactant B72-d replaced reactant B1-d. The specific synthetic route is shown below:

[0170]

[0171] Compound B-72 was obtained in 41% yield. Elemental analysis: C 68 H 61 BF4N2S. Theoretical values: C, 79.67; H, 6.00; B, 1.05; F, 7.41; N, 2.73; S, 3.13; Measured values: C, 79.68; H, 6.02; B, 1.06; F, 7.40; N, 2.71; S, 3.12.

[0172] HRMS(ESI)m / z[M+H]+: Theoretical value: 1024.46; Measured value: 1025.43.

[0173] Synthesis Example 10

[0174] Compound B-73 was synthesized using the synthetic method of Example 1, except that starting material B73-a replaced starting material B1-a, starting material B73-b replaced starting material B1-b, and starting material B73-d replaced starting material B1-d. The specific synthetic route is shown below:

[0175]

[0176] Compound B-73 was obtained in 48% yield. Elemental analysis: C 46 H 25 BF4N2S. Theoretical values: C, 76.25; H, 3.48; B, 1.49; F, 10.49; N, 3.87; S, 4.42; Measured values: C, 76.27; H, 3.49; B, 1.48; F, 10.48; N, 3.85; S, 4.43.

[0177] HRMS(ESI)m / z[M+H]+: Theoretical value: 724.18; Measured value: 725.11.

[0178] Synthesis Example 11

[0179] Compound B-77 was synthesized using the synthetic method described in the synthetic examples, except that reactant B73-a replaced reactant B1-a, reactant B73-b replaced reactant B1-b, reactant B77-c replaced reactant B1-c, and reactant B73-d replaced reactant B1-d. The specific synthetic route is shown below:

[0180]

[0181] Compound B-77 was obtained in 47% yield. Elemental analysis: C 56 H 37 BF4N2S. Theoretical values: C, 78.50; H, 4.35; B, 1.26; F, 8.87; N, 3.27; S, 3.74; Measured values: C, 78.53; H, 4.37; B, 1.25; F, 8.88; N, 3.23; S, 3.73.

[0182] HRMS(ESI)m / z[M+H]+: Theoretical value: 856.27; Measured value: 857.22.

[0183] Synthesis Example 12

[0184] Compound B-89 was synthesized using the synthetic method of Example 1, except that reactant B49-a replaced reactant B1-a, reactant B89-b replaced reactant B1-b, reactant B77-c replaced reactant B1-c, and reactant B26-d replaced reactant B1-d. The specific synthetic route is shown below:

[0185]

[0186] Compound B-89 was obtained in 46% yield. Elemental analysis: C 72 H 69 BF4N2S. Theoretical values: C, 79.98; H, 6.43; B, 1.00; F, 7.03; N, 2.59; S, 2.97; Measured values: C, 79.99; H, 6.45; B, 1.01; F, 7.02; N, 2.58; S, 2.95.

[0187] HRMS(ESI)m / z[M+H]+: Theoretical value: 1080.52; Measured value: 1081.44.

[0188] Synthesis Example 13

[0189] Compound B-104 was synthesized using the synthetic method of Example 1, except that starting material B104-a was replaced with starting material B1-a, starting material B73-b with starting material B1-b, starting material B104-c with starting material B1-c, and starting material B104-d with starting material B1-d. The specific synthetic route is shown below:

[0190]

[0191] Compound B-104 was obtained in 45% yield. Elemental analysis: C 69 H 48 BF4N3S. Theoretical values: C, 79.84; H, 4.66; B, 1.04; F, 7.32; N, 4.05; S, 3.09; Measured values: C, 79.86; H, 4.68; B, 1.03; F, 7.33; N, 4.03; S, 3.07.

[0192] HRMS(ESI)m / z[M+H]+: Theoretical value: 1037.36; Measured value: 1038.31.

[0193] Synthesis Example 14

[0194] Compound B-118 was synthesized using the synthetic method of Example 1, except that starting material B118-a was replaced with starting material B1-a, starting material B73-b with starting material B1-b, starting material B72-c with starting material B1-c, and starting material B118-d with starting material B1-d. The specific synthetic route is shown below:

[0195]

[0196] Compound B-118 was obtained in 42% yield. Elemental analysis: C 86 H 74BF4N3S. Theoretical values: C, 81.44; H, 5.88; B, 0.85; F, 5.99; N, 3.31; S, 2.53; Measured values: C, 81.46; H, 5.89; B, 0.86; F, 5.98; N, 3.30; S, 2.51.

[0197] HRMS(ESI)m / z[M+H]+: Theoretical value: 1268.57; Measured value: 1269.53.

[0198] Synthesis Example 15

[0199] Compound B-126 was synthesized using the synthetic method of Example 1, except that reactant B118-a was used instead of reactant B1-a, reactant B73-b was used instead of reactant B1-b, reactant B126-c was used instead of reactant B1-c, and reactant B126-d was used instead of reactant B1-d. The specific synthetic route is shown below:

[0200]

[0201] Compound B-126 was obtained in 41% yield. Elemental analysis: C 89 H 84 BF4N3S. Theoretical values: C, 81.32; H, 6.44; B, 0.82; F, 5.78; N, 3.20; S, 2.44; Measured values: C, 81.34; H, 6.46; B, 0.81; F, 5.79; N, 3.18; S, 2.42.

[0202] HRMS(ESI)m / z[M+H]+: Theoretical value: 1313.64; Measured value: 1314.44.

[0203] Device Example 1

[0204] Device Example 1 provides an organic electroluminescent device, such as Figure 1 As shown, the organic electroluminescent device has the following layered structure in sequence: substrate 1 / anode 2 / hole injection layer 3 (HIL) / hole transport layer 4 (HTL) / light emission layer 5 (EML) / electron transport layer 6 (ETL) / electron injection layer 7 (EIL), and finally cathode 8.

[0205] The materials used to manufacture the above-mentioned organic electroluminescent devices are shown in Table 3 below:

[0206] Table 3 Some materials used in organic light-emitting devices

[0207]

[0208] The fabrication of the above-mentioned organic electroluminescent device includes the following steps:

[0209] 1) Substrate cleaning:

[0210] The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio of acetone and ethanol 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0211] 2) Preparation of organic layer:

[0212] The ITO transparent substrate was transferred to an evaporation equipment and vacuumed to 1×10⁻⁶. -6 Up to 2×10 -4 Pa, hole injection layer (HIL) / hole transport layer (HTL) / light emission layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / thick cathode (Al) are sequentially deposited on the anode film.

[0213] in:

[0214] The hole injection layer (HIL) is a mixture of HAT-CN and HT-1, with a mass ratio of HAT-CN to HT-1 of 3:97, a thickness of 10 nm, and a total evaporation rate of 0.1 nm / s.

[0215] The hole transport layer (HTL) is made of HT-1 material, has a thickness of 40 nm, and a total evaporation rate of 0.1 nm / s.

[0216] The light-emitting layer (EML) is vacuum-deposited by co-evaporation. The material of the light-emitting layer includes a host material and a dopant material. The host material is BH-1, and the dopant material is composed of the B-1 compound in synthesis example 1. The weight ratio of the host material to the dopant material is 96:4, the thickness is 30 nm, and the total evaporation rate is 0.1 nm / s.

[0217] The electron transport layer (ETL) is made of ET, has a thickness of 30 nm, and a total evaporation rate of 0.1 nm / s.

[0218] The electron injection layer (EIL) is made of LiQ with a thickness of 1 nm and a total evaporation rate of 0.1 nm / s.

[0219] The cathode is made of aluminum with a thickness of 150 nm and a deposition rate of 1 nm / s.

[0220] Device Examples 2-15

[0221] The device is largely the same as in Device Example 1, except that material B-1 in Device Example 1 is replaced with the compounds obtained in Synthesis Examples 2 to 15. Please refer to Table 4 for details.

[0222] Table 4. Compounds and thicknesses in the luminescent layer

[0223] Serial Number EML / Thickness Device Example 1 BH-1:B-1 (mass ratio 96:4) / 30nm Device Example 2 BH-1:B-7 (mass ratio 96:4) / 30nm Device Example 3 BH-1:B-12 (mass ratio 96:4) / 30nm Device Example 4 BH-1:B-19 (mass ratio 96:4) / 30nm Device Example 5 BH-1:B-26 (mass ratio 96:4) / 30nm Device Example 6 BH-1:B-42 (mass ratio 96:4) / 30nm Device Example 7 BH-1:B-49 (mass ratio 96:4) / 30nm Device Example 8 BH-1:B-58 (mass ratio 96:4) / 30nm Device Example 9 BH-1:B-72 (mass ratio 96:4) / 30nm Device Example 10 BH-1:B-73 (mass ratio 96:4) / 30nm m Device Example 11 BH-1:B-77 (mass ratio 96:4) / 30nm Device Example 12 BH-1:B-89 (mass ratio 96:4) / 30nm Device Example 13 BH-1:B-104 (mass ratio 96:4) / 30nm Device Example 14 BH-1:B-118 (mass ratio 96:4) / 30nm Device Example 15 BH-1:B-126 (mass ratio 96:4) / 30nm Device Comparison Example 1 BH-1:REF-1 (mass ratio 96:4) / 30nm Device Comparison Example 2 BH-1:REF-2 (mass ratio 96:4) / 30nm

[0224] Device Comparison Example 1

[0225] The device is largely the same as in Device Example 1, except that material B-1 in Device Example 1 is replaced with the following structure REF-1, as shown in Table 4.

[0226]

[0227] Device Comparison Example 2

[0228] The device is largely the same as in Device Example 1, except that material B-1 in Device Example 1 is replaced with the following structure REF-2, as shown in Table 4.

[0229]

[0230] Device Test Examples

[0231] The organic electroluminescent devices obtained in Device Examples 1 to 15 and Device Comparative Examples 1 and 2 in the device examples were tested.

[0232] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;

[0233] Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0234] Lifetime test: Current density 10mA / cm 2 The recording time (in hours) was recorded when the device brightness dropped to 95% of its original brightness. The lifetime T95 of device Comparative Example 1 was set, and the lifetime T95 results of devices 1 to 15 relative to device Comparative Example 1 are shown in Table 5.

[0235] Table 5. Photoelectric property test results for Device Examples 1-15 and Device Comparative Examples 1 and 2.

[0236]

[0237]

[0238] As can be seen from Table 5, the organic electroluminescent devices prepared using the compound provided by the present invention as the doping material of the light-emitting layer have lower driving voltage, higher current efficiency and longer lifetime.

[0239] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic electroluminescent compound, characterized in that: The structural formula is as follows: Among them, Q1, Q2, Q3, and Q4 are the same or different, and each is independently a substituted or unsubstituted C6-C60 aromatic ring or a substituted or unsubstituted C6-C60 aromatic heterocycle. X is selected from O, S, NR 6 CR 7 R 8 ; Among them, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 The same or different, and each independently selected from hydrogen, deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 heterocycloalkyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C1-C60 alkylthio, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C4-C60 heteroaryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C4-C60 heteroaryloxy; a, b, c, and d may be the same or different, and each may be an integer selected independently from 0 to 7; e may be an integer selected from 0 to 3. The substituents in the substituted C6-C60 aromatic ring, substituted C6-C60 aromatic heterocyclic ring, substituted C1-C60 alkyl, substituted C3-C60 cycloalkyl, substituted C2-C60 heterocyclic alkyl, substituted C1-C60 alkoxy, substituted C1-C60 alkylthio, substituted C6-C60 aryl, substituted C4-C60 heteroaryl, substituted C6-C60 aryloxy, and substituted C4-C60 heteroaryloxy are selected from deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, C1-C60 alkyl, C3-C60 cycloalkyl, C2-C60 heterocyclic alkyl, C1-C60 alkoxy, C1-C60 alkylthio, C6-C60 aryl, C4-C60 heteroaryl, C6-C60 aryloxy, and C4-C60 heteroaryloxy.

2. The organic electroluminescent compound according to claim 1, characterized in that: Q1, Q2, Q3, and Q4 may be the same or different, and each is independently selected from substituted or unsubstituted C6-C50 aromatic rings or substituted or unsubstituted C6-C50 aromatic heterocycles. The substituents in the substituted C6-C50 aromatic ring or the substituted C6-C50 aromatic heterocycle are selected from deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, C1-C50 alkyl, C3-C50 cycloalkyl, C2-C50 heterocycloalkyl, C1-C50 alkoxy, C1-C50 alkylthio, C6-C50 aryl, C4-C50 heteroaryl, C6-C50 aryloxy, and C4-C50 heteroaryloxy. Preferably, Q1, Q2, Q3, and Q4 are the same or different, and each is independently selected from substituted or unsubstituted C6-C25 aromatic rings or substituted or unsubstituted C6-C25 aromatic heterocycles. The substituents in the substituted C6-C25 aromatic ring or the substituted C6-C25 aromatic heterocycle are selected from deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C2-C25 heterocycloalkyl, C1-C25 alkoxy, C1-C25 alkylthio, C6-C25 aryl, C4-C25 heteroaryl, C6-C25 aryloxy, and C4-C25 heteroaryloxy. Preferably, Q1, Q2, Q3, and Q4 are the same or different, and each is independently selected from substituted or unsubstituted group D. Group D is selected from one or more of phenyl, biphenyl, terphenyl, pyridyl, benzothiophene, benzofuranyl, naphthothiophene, naphthofuranyl, carbazothiophene, carbazofuranyl, fluorenyl, fluorenyl, fluorenyl, fluorenylfuranyl, naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, dihydroanthraphene, dimethylfluorenyl, dihydroanthraphene, dihydroanthraphene, dihydronaphthofuranyl, tetrahydronaphthyl, dihydronaphthyl, carbazoyl, dibenzothiophene, dibenzofuranyl, and triphenylamino. The substituents in the substituted gene D are selected from deuterium, carboxyl, nitro, cyano, amino, halogen, trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfuranylsilyl, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexyl Methyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylisopropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, spirodel, spiroundecyl, adamantyl, methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentoxy, isopentoxy, hexoxy, azircyclopropane, pyrrolidine, piperidine, azircycloheptane, azircycloheptane.

3. The organic electroluminescent compound according to claim 1, characterized in that: Two of Q1, Q2, Q3, and Q4 are selected from substituted or unsubstituted fluorene groups; The substituents in the substituted fluorene group are selected from one or more of deuterium, carboxyl, nitro, cyano, amino, halogen, and silyl groups.

4. The organic electroluminescent compound according to any one of claims 1 to 3, characterized in that: Formula I is selected from one of the following structures: (1-1) to (1-6):

5. The organic electroluminescent compound according to claim 1, characterized in that: The R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 The same or different, and each independently selected from hydrogen, deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, substituted or unsubstituted C1-C50 alkyl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C2-C50 heterocycloalkyl, substituted or unsubstituted C1-C50 alkoxy, substituted or unsubstituted C1-C50 alkylthio, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C4-C50 heteroaryl, substituted or unsubstituted C6-C50 aryloxy, substituted or unsubstituted C4-C50 heteroaryloxy, and The substituents in the substituted C1-C50 alkyl, substituted C3-C50 cycloalkyl, substituted C2-C50 heterocycloalkyl, substituted C1-C50 alkoxy, substituted C1-C50 alkylthio, substituted C6-C50 aryl, substituted C4-C50 heteroaryl, substituted C6-C50 aryloxy, and substituted C4-C50 heteroaryloxy groups are selected from deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, C1-C50 alkyl, C3-C50 cycloalkyl, C2-C50 heterocycloalkyl, C1-C50 alkoxy, C1-C50 alkylthio, C6-C50 aryl, C4-C50 heteroaryl, C6-C50 aryloxy, and C4-C50 heteroaryloxy groups. Preferably, the R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 The same or different, and each independently selected from hydrogen, deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C2-C25 heterocycloalkyl, substituted or unsubstituted C1-C25 alkoxy, substituted or unsubstituted C1-C25 alkylthio, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C4-C25 heteroaryl, substituted or unsubstituted C6-C25 aryloxy, substituted or unsubstituted C4-C25 heteroaryloxy, and The substituents in the substituted C1-C25 alkyl, substituted C3-C25 cycloalkyl, substituted C2-C25 heterocycloalkyl, substituted C1-C25 alkoxy, substituted C1-C25 alkylthio, substituted C6-C25 aryl, substituted C4-C25 heteroaryl, substituted C6-C25 aryloxy, and substituted C4-C25 heteroaryloxy groups are selected from deuterium, carboxyl, nitro, cyano, amino, halogen, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C2-C25 heterocycloalkyl, C1-C25 alkoxy, C1-C25 alkylthio, C6-C25 aryl, C4-C25 heteroaryl, C6-C25 aryloxy, and C4-C25 heteroaryloxy groups. Preferably, the R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 The same or different, and each independently selected from hydrogen, deuterium, carboxyl, nitro, cyano, amino, halogen, trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfuranylsilyl, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl The group consisting of octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylisopropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, spirodel, spiroundecyl, adamantyl, methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentoxy, isopentoxy, hexoxy, azircyclopropane, pyrrolidine, piperidine, azircycloheptane, or the following groups:

6. The organic electroluminescent compound according to claim 1, characterized in that: a, b, c, and d may be the same or different, and each is an independent integer selected from 0 to 6; Preferably, a, b, c, and d are the same or different, and each is an independent integer selected from 0 to 5; Preferably, a, b, c, and d are the same or different, and each is an independent integer selected from 0 to 4; Preferably, a, b, c, and d are the same or different, and each is an independent integer selected from 0 to 3; Preferably, a, b, c, and d are the same or different, and each is an independent integer selected from 0 to 2; Preferably, a, b, c, and d are the same or different, and each is an independent integer selected from 0 to 1; Preferably, e is selected from integers from 0 to 2; Preferably, e is selected from integers from 0 to 1.

7. The organic electroluminescent compound according to claim 1, characterized in that: Formula I is selected from one of the following structures: Formula B-1 to B-136.

8. An organic electroluminescent material, characterized in that: It includes the organic electroluminescent compound as described in any one of claims 1 to 7.

9. An organic electroluminescent device, characterized in that: The organic electroluminescent device includes a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer between the first electrode and the second electrode, wherein the organic layer comprises an organic electroluminescent compound as described in any one of claims 1 to 7 or an organic electroluminescent material as described in claim 8; Preferably, the organic layer includes a light-emitting layer, which includes an organic electroluminescent compound as described in any one of claims 1 to 7 or an organic electroluminescent material as described in claim 8.

10. The application of the organic electroluminescent device as described in claim 9 in optical fiber equipment, lighting equipment, electrophotographic photosensitive equipment, photoelectric converters, organic solar cells, switching element equipment, organic light-emitting field-effect transistors, image sensors, or dye lasers.

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