WO2024230681A1 - Light-emitting compound and related electronic device - Google Patents

Abstract

The present invention belongs to the technical field of the preparation of electroluminescent devices. Disclosed are a new light-emitting compound and a related electronic device.

Description

A luminescent compound and related electronic device Technical Field

The invention belongs to the technical field of electroluminescent device preparation, and specifically relates to a luminescent compound and related electronic devices.

Background Art

With the development of multimedia technology and the improvement of information requirements, the requirements for panel display performance are getting higher and higher. Among them, OLED has a series of advantages such as autonomous luminescence, low-voltage DC drive, full curing, wide viewing angle, rich colors, etc., and has attracted widespread attention for its potential application in the new generation of display and lighting technology, and its application prospects are very broad. Organic electroluminescent devices are spontaneous luminescent devices. The mechanism of OLED luminescence is that under the action of an external electric field, electrons and holes are injected from the positive and negative electrodes respectively, and then migrate, recombine and decay in the organic material to produce luminescence. The typical structure of OLED includes one or more functional layers of cathode layer, anode layer, electron injection layer, electron transport layer, hole blocking layer, hole transport layer, hole injection layer and light-emitting layer. Although the research progress of organic electroluminescence is very rapid, there are still many problems to be solved. For example, high-efficiency and long-life blue light materials have always been a problem to be solved by technicians in this field.

Summary of the invention

202310507443.9 The purpose of the present invention is to provide a silicon-containing compound and its application in an organic light-emitting device in view of the deficiencies in the prior art. The present invention effectively suppresses the interaction between luminescent molecules by introducing a large steric hindering group of triphenylsilicon. The prepared silicon-containing compound has good electron and hole receiving ability, can improve the energy transfer performance between the host and the guest, and reduce the concentration of high-energy excitons in the light-emitting layer, thereby realizing efficient and long-life blue light materials. Therefore, this type of silicon-containing compound has important applications in organic light-emitting devices.

In order to achieve the purpose of the present invention, the technical solution of the present invention is as follows:

According to one or more embodiments, the present invention provides a silicon-containing compound having a structure shown in the following formula (1-1):

;

In formula (1-I), ring A, ring B, and ring C are unsubstituted, monosubstituted, or polysubstituted aryl rings, heteroaryl rings, or heteroalkyl rings; R ₁ , R ₂ , R ₃ , R ₄ , and R ₅ represent polysubstituted groups, which are unsubstituted, monosubstituted, or polysubstituted; at least one substituent among R ₁ -R ₅ is independently selected from the group consisting of: The structure shown.

More preferably, R ₁ to _{R 5} are each independently selected from the group consisting of hydrogen, oxygen, nitrogen, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 6 to 20 carbon atoms.

More preferably, in formula (1-I), ring A is a benzene ring or thiophene, and ring B and ring C are a benzene ring or pyridine.

Furthermore, at least one hydrogen in the compound or structure represented by formula (1-1) may be substituted by deuterium, cyano or halogen.

Further, R ₁ -R ₅ may be each independently selected from a group comprising the following substituents; ;

* is the connection point, and the group may be unsubstituted or substituted with other substituents, and the other substituents may be selected from deuterium, alkyl groups having 1 to 24 carbon atoms, cycloalkyl groups having 3 to 14 carbon atoms, aryl groups having 6 to 20 carbon atoms, and heteroaryl groups having 6 to 20 carbon atoms.

According to one or more embodiments, the silicon-containing compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:

On the one hand, the present invention also provides the use of the silicon-containing compound with the general structure shown in the above formula (1-I) in electronic devices.

Furthermore, the electronic devices include organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quenching devices (O-FQDs), light emitting electrochemical cells (LECs), and organic laser diodes (O-lasers).

In another aspect, the present invention further provides an organic electroluminescent device, which comprises a silicon-containing compound having a general structure as shown in the above formula (1-I).

Furthermore, the organic electroluminescent device comprises a cathode, an anode and an organic functional layer therebetween; the organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises a silicon-containing compound having a general structure as shown in formula (1-I) above. The mass percentage of the silicon-containing compound is 0.1%-50%.

In another aspect, the present invention further provides an organic photoelectric device, comprising a first electrode; a second electrode facing the first electrode; and a light-emitting material layer disposed between the first electrode and the second electrode, wherein the light-emitting material layer comprises a silicon-containing compound having a general structure as shown in formula (1-I) above. For example, the silicon-containing compound can be included in the light-emitting material layer as a dopant.

The present invention also provides a composition, which comprises a silicon-containing compound having a general structure as shown in the above formula (1-I).

The present invention also provides a preparation, which comprises a silicon-containing compound having a general structure as shown in the above formula (1-I) or a composition as described above and at least one solvent. The solvent is not particularly limited, and can be used, for example, unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, butyl chloride, butyl bromide, pentyl chloride, pentyl bromide, hexyl chloride, hexyl bromide, cyclohexyl chloride, cyclohexyl bromide, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, ether solvents such as tetrahydrofuran, tetrahydropyran, and ester solvents such as alkyl benzoate.

The present invention also provides a display or lighting device, which comprises one or more of the organic electroluminescent devices described above.

The silicon-containing compounds involved in the present invention have good thermal stability. The large steric hindrance group of triphenylsilicon can effectively inhibit the interaction between luminescent molecules, thereby improving the efficiency of the device. The silicon-containing compounds involved in the present invention have good electron and hole receiving capabilities, which can improve the energy transfer performance between the subject and the object. Specifically, the organic electroluminescent device made of the silicon-containing compound of the present invention as a functional layer, especially as a light-emitting layer, has improved current efficiency and reduced lighting voltage. At the same time, the life of the device is greatly improved, indicating that after most electrons and holes recombine, the energy is effectively transferred to the silicon-containing compound for luminescence rather than heat generation. 202310507443.9.

202310753983.5 The purpose of the present invention is to provide a narrow emission luminescent compound and its application in electronic devices in view of the deficiencies in the prior art. The present invention effectively suppresses the interaction between luminescent molecules by introducing large steric hindering groups. The prepared narrow emission luminescent compound has good electron and hole receiving ability, which can improve the energy transfer performance between the host and the guest, reduce the concentration of high-energy excitons in the light-emitting layer, and thus realize efficient and long-life blue light materials. Narrow emission luminescent compounds have important applications in organic light-emitting devices.

In order to achieve the purpose of the present invention, the technical solution of the present invention is as follows:

A narrow emission luminescent compound, wherein the luminescent compound has a structure shown in the following formula (2-I):

In formula 2-I, E is a substituted phenyl group, wherein the substitution is mono- or poly-substituted; the substituents are selected from one or a combination of at least two of deuterium, Si, C1-C12 alkyl, C1-C12 azaalkyl, C6-C30 aryl, C6-C30 aromatic silicon, C6-C30 aromatic amine, and C6-C30 azaaryl;

In formula 2-I, R ₆ -R ₉ are each independently selected from one or a combination of at least two of hydrogen, N, C1-C12 alkyl, C3-C20 cycloalkyl, C6-C30 aryl, and C6-C30 arylamine; any two adjacent substituents are not connected or are connected to each other to form a ring structure;

In formula 2-I, Z ₁ -Z ₅ are each independently represented by N or CR, and R is independently selected from one or a combination of at least two of hydrogen, C1-C12 alkyl, C3-C20 cycloalkyl, C6-C30 aryl, and C6-C30 heteroaryl; any two adjacent substituents are not connected or are connected to each other to form a ring structure.

As a preferred embodiment, in Formula 2-I, R ₇ and R ₈ are each independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted diphenylamine; when there are substituents, the substitution is mono- or poly-substitution, and the substituents are selected from C1-C6 alkyl or C6-C12 aryl.

As a preferred embodiment, in formula 2-I, R is selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, butyl, tert-butyl, phenyl, biphenyl, tert-butylbiphenyl, tert-butylbenzene, pyridyl or phenylpyridine, and any two adjacent substituents are not connected or are connected to each other to form a ring structure.

More preferably, in formula 2-I, R ₆ -R ₉ are each independently selected from one or a combination of at least two of hydrogen, deuterium, methyl, ethyl, propyl, butyl, tert-butyl, phenyl, biphenyl, tert-butylbiphenyl, tert-butylbenzene, pyridyl, phenylpyridine, aromatic amino, and diphenylamine; any two adjacent substituents are not connected or are connected to each other to form a ring structure.

As a preferred embodiment, in Formula 2-I, R ₆ and R ₉ are each independently selected from hydrogen, tert-butyl, phenyl, biphenyl, tert-butylphenyl, and 3,5-di-tert-butylphenyl.

As a preferred embodiment, the hydrogen atoms in the groups R, R ₆ -R ₉ in formula 2-I may be partially or fully deuterated.

As a preferred embodiment, in Formula 2-1, E is selected from the structural group shown in Formula 2-2 or Formula 2-3, and the hydrogen atoms in the structural group may be partially or fully deuterated:

;

Wherein, R ₁₀ and R ₁₁ are each independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamine; when containing substituents, the substituents are selected from C1-C6 alkyl and C6-C12 aryl; the dotted line indicates that it can be connected to the parent core.

Furthermore, the R ₁₀ and R ₁₁ are each independently selected from phenyl, tolyl, biphenyl, tert-butylphenyl, pyridine, carbazolyl or diphenyltriazine.

The present invention also provides a narrow emission light compound material, wherein the narrow emission light compound material is selected from the following specific structural compounds:

In another aspect, the present invention also provides the use of a narrow emission compound having a general structure as shown in the above formula 2-I in an electronic device.

Furthermore, the electronic devices include organic photovoltaic devices, organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quenching devices (O-FQDs), light emitting electrochemical cells (LECs), and organic laser diodes (O-lasers).

In another aspect, the present invention further provides an organic electroluminescent device, which comprises a narrow emission compound having a general structure as shown in Formula 2-I above.

Furthermore, the organic electroluminescent device comprises a cathode, an anode and at least one organic functional layer between the cathode and the anode; the organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises a narrow emission compound having a general structure as shown in formula 2-1 above. The mass percentage of the narrow emission compound is 0.1%-50%.

In another aspect, the present invention also provides an organic photoelectric device, comprising a first electrode; a second electrode facing the first electrode; and a light-emitting material layer disposed between the first electrode and the second electrode, wherein the light-emitting material layer comprises a narrow emission compound having a general structure as shown in Formula 2-I above. For example, the narrow emission compound can be included in the light-emitting material layer as a dopant.

The present invention also provides a composition, which comprises a narrow emission compound having the general structure shown in Formula 2-I above.

The present invention also provides a preparation, which comprises a narrow emission compound of the general structure shown in the above formula 2-1 or the above composition and at least one solvent. The solvent is not particularly limited, and can be used, for example, unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, methylene chloride, ethylene dichloride, butyl chloride, butyl bromide, pentyl chloride, pentyl bromide, hexyl chloride, hexyl bromide, chlorocyclohexane, bromocyclohexane, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, ether solvents such as tetrahydrofuran, tetrahydropyran, ester solvents such as alkyl benzoate, etc., which are well known to those skilled in the art.

The present invention also provides a display or lighting device, which comprises one or more of the organic electroluminescent devices described above.

The compounds involved in the present invention have good thermal stability. Through large steric hindering groups such as triphenyl, dicarbazolylbenzene, and diphenylamine, the interaction between luminescent molecules can be effectively inhibited, thereby improving the efficiency of the device. Specifically, the organic electroluminescent device made with the narrow emission compound of the present invention as a functional layer, especially as a light-emitting layer, has an improved current efficiency and a greatly improved device life, indicating that after most electrons and holes recombine, the energy is effectively transferred to the narrow emission luminescent material for luminescence rather than heat generation. 202310753983.5.

202311482550.7 In order to solve the above technical problems, the present invention provides an organic compound, an OLED having the compound, and a display or lighting device.

The organic compound provided by the present invention is realized by the following technical scheme:

An organic compound having a structure shown in the following formula (3-I):

Formula (3-I)

In formula (3-I), R ₁ -R ₈ are each independently selected from hydrogen or deuterium; R ₉ and R ₁₀ are each independently selected from hydrogen, deuterium, C6-C30 aryl, C5-C30 heteroaryl, C6-C30 fused aromatic ring, C3-C30 fused heterocyclic ring, and the group consisting thereof; the heteroatom is O;

At least one substituent among R ₉ -R ₁₀ is selected from the structure shown in formula (3-II):

In formula (3-II), R ₁₁ is selected from hydrogen, C6-C30 aryl, C5-C30 heteroaryl, C5-C30 fused ring, and a combination thereof, and the combination includes a combination in the form of a fused ring; the heteroatom is O; Selected from absent or benzofuran; * indicates the attachment position.

Preferably, in formula (3-I), R ₉ or R ₁₀ is selected from deuterium, phenyl, naphthyl, phenanthryl, biphenyl, and the group consisting thereof.

In formula (3-II), R ₁₁ is selected from hydrogen, phenyl, furyl, benzofuranyl, and a combination thereof, and the combination includes a combination in the form of a fused ring.

According to one or more embodiments, the present invention provides an organic compound, wherein the organic compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:

.

The present invention also provides a use of the organic compound as described above in an organic electroluminescent device.

The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising:

A substrate layer; a first electrode, the first electrode being on the substrate; an organic light-emitting functional layer, the organic light-emitting functional layer being on the first electrode; and a second electrode, the second electrode being on the organic light-emitting functional layer;

The organic light-emitting functional layer comprises a light-emitting layer; the light-emitting layer comprises the organic compound as described above.

Preferably, the light-emitting layer further comprises a boron nitrogen compound having a structure shown in the following formula (3-III):

;

In formula (3-III), R ₁₂ -R ₁₅ are each independently selected from hydrogen, deuterium, halogen, C1-C20 alkyl, C3-C20 cycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C3-C30 silyl, C6-C30 arylsilyl, C5-C30 fused ring, and combinations thereof, and the combination includes combination in the form of a fused ring, and the heteroatom is O.

Preferably, in the formula (3-III), R ₁₂ is selected from methyl, tert-butyl, tert-butylphenyl, arylcyclohexane, phenyl, and combinations thereof.

Preferably, in the formula (3-III), R ₁₃ is selected from tert-butylphenyl or diphenylfuran.

Preferably, in the formula (3-III), R ₁₄ is selected from deuterium, F, methyl, tert-butyl, phenyl, triarylsilane, tert-butyldiphenylsilane, and combinations thereof.

Preferably, in the formula (3-III), R ₁₅ is selected from methyl, tert-butyl, phenyl, tert-butylphenyl, benzocyclohexane, and combinations thereof.

Preferably, the boron nitrogen compound is selected from any one of the following chemical structures, wherein "D" represents deuterium:

The organic electroluminescent device of the present invention can be used in OLED lighting or display devices. Specifically, it can be used in the commercial field, such as display screens of products and equipment such as POS machines and ATM machines, copiers, vending machines, game machines, gas stations, card punching machines, access control systems, electronic scales, etc.; in the communication field, such as display screens of products such as mobile phones, various video intercom systems (videophones), mobile network terminals, ebooks (electronic books), etc.; in the computer field, such as display screens of home and/or commercial computers (PC/workstations, etc.), PDAs and laptops; in consumer electronic products, such as display screens of decorative items (soft screens) and lamps, various audio equipment, MP3, calculators, digital cameras, head-mounted displays, digital video cameras, portable DVDs, portable televisions, electronic clocks, handheld game consoles, various household appliances (OLED TVs), etc.; in the transportation field, such as various indicator and symbol display screens such as GPS, car audio, car phones, aircraft instruments and equipment.

Preferably, the organic electroluminescent device prepared by the present invention is used in smart phones, tablet computers, smart wearable devices, televisions, VR, micro-display fields, and automobile central control screens or automobile taillights.

The present invention also provides a preparation, which comprises an organic compound having a structure as shown in the above formula (3-I) or a composition as described above and at least one solvent. The solvent is not particularly limited, and can be used as those skilled in the art, for example, unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, butyl chloride, butyl bromide, pentyl chloride, pentyl bromide, hexyl chloride, hexyl bromide, cyclohexyl chloride, cyclohexyl bromide, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, ether solvents such as tetrahydrofuran, tetrahydropyran, and ester solvents such as alkyl benzoate.

The organic electroluminescent device of the present invention can be used in an OLED lighting or display device.

The present invention also provides a display or lighting device, which comprises one or more of the organic electroluminescent devices described above.

In summary, compared with the prior art, the present invention has the following beneficial effects:

The organic compound of the present invention, through the combination of anthracene ring and specific substituent groups, makes the structure of the organic compound have good movement and injection of holes and electrons, and can improve the stability of the compound at the same time; the boron nitrogen compound provided by the present invention has excellent luminescence characteristics due to the narrow half-maximum full width; after it is used together with the organic compound provided by the present invention as a light-emitting layer material to prepare an organic light-emitting device, the organic light-emitting device can effectively have a lower driving voltage and maintain voltage stability, and the luminous efficiency is improved, and the working life of the device can also be better. 202311482550.7

DETAILED DESCRIPTION

202310507443.9 The content of the present invention is described in detail below. The description of the constituent elements recorded below is sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. The present disclosure can be more easily understood by referring to the following specific embodiments and the examples contained therein. Before disclosing and describing the compounds, devices and/or methods of the present invention, it should be understood that, unless otherwise stated, they are not limited to specific synthetic methods or specific reagents, as this can vary. It should also be understood that the terms used in the present invention are only used to describe specific aspects and are not intended to be limiting. Although any methods and materials similar or equivalent to those described in the present invention can be used in the practice or experiment, exemplary methods and materials are now described.

The "alkyl group having 1 to 24 carbon atoms" of the present invention refers to a monovalent alkyl group having 1 to 24 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms. Examples of this term include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-hexyl, etc.

The "cycloalkyl group having 3 to 14 carbon atoms" of the present invention refers to a cyclic alkyl group having 3 to 14 carbon atoms and having a monocyclic or polycyclic condensed ring, which may be substituted by 1 to 3 alkyl groups at will. Such cycloalkyl groups include, for example, monocyclic structures such as cyclopropyl, cyclobutyl, cyclopentyl, cyclooctyl, 1-methylcyclopropyl, 2-methylcyclopentyl, 2-methylcyclooctyl, etc., or polycyclic structures such as adamantyl, etc.

The "aryl group having 6 to 20 carbon atoms" of the present invention refers to an unsaturated aromatic carbocyclic ring having 6 to 20 carbon atoms and having a monocyclic ring (such as phenyl) or a polycyclic condensation (such as naphthyl or anthracenyl). Preferred aryl groups include phenyl, naphthyl, etc. Unless otherwise defined for individual substituents, such aryl groups may be optionally substituted by 1 to 3 of the following substituents: hydroxyl, acyl, acyloxy, alkyl, alkoxy, alkenyl, alkynyl, amino, aminoacyl, aryl, aryloxy, carboxyl, carboxyl ester, aminocarboxyl ester, cyano, halogen, nitro, heteroaryl, heterocycle, thioalkoxy, trihalomethyl, etc. Preferred substituents include alkyl, alkoxy, halogen, cyano, nitro, trihalomethyl and thioalkoxy. But not limited thereto.

The "heteroaryl group having 6 to 20 carbon atoms" described in the present invention refers to a general term for groups in which one or more aromatic carbon atoms in an aromatic group are replaced by heteroatoms, wherein the heteroatoms include but are not limited to oxygen, sulfur or nitrogen atoms, and the heteroaryl group may be a monocyclic heteroaryl group or a condensed-ring heteroaryl group. Examples may include pyridyl, pyrrolyl, pyridyl, thienyl, furyl, indolyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc., but are not limited thereto.

As used in the specification and the appended claims, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to "a component" includes a mixture of two or more components.

Unless otherwise stated, all commercial reagents involved in the following experiments were used directly after purchase.

In a preferred embodiment of the present invention, the OLED device of the present invention contains a hole transport layer, and the hole transport material can be preferably selected from known or unknown materials, and is particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures (Ph is phenyl):

In a preferred embodiment of the present invention, the hole injection layer contained in the OLED device of the present invention. The preferred hole injection layer material of the present invention is the following structure, but it does not mean that the present invention is limited to the following structure:

In a preferred embodiment of the present invention, the electron transport layer can be selected from at least one of the following compounds, but it does not mean that the present invention is limited to the following structures:

The preparation method of the silicon-containing compound, i.e., the guest compound, and the luminescent properties of the device are explained in detail in conjunction with the following examples.

The OLED device of the present invention contains a host material, which can be selected from known or unknown materials, and is particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures:

Example 1-1 Synthesis of Compound 1-53

(1) Synthesis of compound 1-53-3:

Compound 1-53-1 (248 mg, 1 mmoL) and compound 1-53-2 (149 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. After reflux for 72 hours, the reaction system was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:4, to obtain product 1-53-3 (170 mg, yield 54%). Mass spectrum m/z, theoretical value 315.18; measured value M+H: 316.22.

Synthesis of compound 1-53-5:

Compound 1-53-3 (316 mg, 1 mmoL) and compound 1-53-4 (269 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. After reflux for 48 hours, the reaction system was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:5, to obtain product 1-53-5 (256 mg, yield 57%). Mass spectrum m/z, theoretical value 447.18; measured value M+H: 448.26.

Synthesis of compound 1-53-7:

Compound 1-53-5 (448 mg, 1 mmoL) and compound 1-53-6 (351 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. After reflux for 48 hours, the reaction system was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:6, to obtain product 1-53-7 (241 mg, yield 32%). Mass spectrum m/z, theoretical value 762.35; measured value M+H: 763.39.

Synthesis of compound 1-53-9:

Compound 1-53-7 (763 mg, 1 mmoL) and compound 1-53-8 (562 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. After reflux for 48 hours, the reaction system was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:7, to obtain product 1-53-9 (258 mg, yield 21%). Mass spectrum m/z, theoretical value 1251.55; measured value M+H: 1252.59.

Synthesis of Compound 1-53

Compound 1-53-9 (1.253 g, 1 mmoL) was dissolved in 60 mL of anhydrous tert-butylbenzene. The reaction system was cooled to -78°C, and BuLi (1 mL, 2 mmoL, 2M in hexane) was slowly added. After reacting at -78°C for 4 hours, BBr ₃ (247 mg, 1 mmoL) was slowly added. After reacting at -50°C for 1 hour, the reaction was warmed to room temperature, and then N,N-diisopropylethylamine (387 mg, 3 mmoL) was added, followed by heating to 120°C for 12 hours. After cooling to room temperature, 5 mL of sodium acetate aqueous solution (1 M) was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the obtained crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:8, to obtain product 1-53 (378 mg, yield 32%). Mass spectrum m/z, theoretical value 1181.63; measured value M+H: 1182.66.

Example 1-2 Synthesis of Compound 1-4

Synthesis of compound 1-4-2

At -78 °C, BuLi (0.5 mL, 1 mmoL, 2M in hexane) was slowly added to a tetrahydrofuran (50 mL) solution of compound 1-4-1 (396 mg, 1 mmoL). After 3 hours of reaction, triphenylsilyl chloride (294 mg, 1 mmoL) was slowly added. After slowly warming to room temperature, the reaction was allowed to proceed overnight, and then the temperature was raised to 80 °C for 6 hours. After cooling to room temperature, 1 mL of ice water was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:9, to obtain product 1-4-2 (246 mg, yield 47%). Mass spectrum m/z, theoretical value 525.92; measured value M+H: 526.94.

Synthesis of compound 1-4-4

Compound 1-4-2 (529 mg, 1 mmoL) and compound 1-4-3 (281 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:6, to obtain product 1-4-4 (222 mg, yield 30%). Mass spectrum m/z, theoretical value 727.20; measured value M+H: 728.26.

Synthesis of compound 1-4-6

Compound 1-4-4 (729 mg, 1 mmoL) and compound 1-4-5 (338 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:7, to obtain product 1-4-6 (321 mg, yield 33%). Mass spectrum m/z, theoretical value 984.46; measured value M+H: 985.51.

Synthesis of Compounds 1-4

Under nitrogen atmosphere and zero temperature, tert-butyl lithium (1.25 mL, 1.6 M pentane solution, 2 mmoL) was slowly added dropwise to a solution of compound 1-4-6 (986 mg, 1 mmoL) in tert-butylbenzene (100 mL). After the system was reacted at 60°C for 4 hours, the temperature was lowered to -50°C, and then BBr ₃ (494 mg, 2 mmoL) was added. After reacting at room temperature for 1 hour, N,N-diisopropylethylamine (259 mg, 2 mmoL) was added. The temperature was then raised to 120°C for 12 hours. After cooling to room temperature, 5 mL of sodium acetate aqueous solution (1 M) was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the obtained crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:9, to obtain product 1-4 (302 mg, yield 31%). Mass spectrum m/z, theoretical value 958.49; found value M+H: 959.53.

Example 1-3 Synthesis of Compound 1-49

Synthesis of compound 1-49-3

Compound 1-49-1 (0.326 g, 1 mmoL) and compound 49-2 (0.413 g, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was heated under reflux for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:3, to obtain product 49-3 (348 mg, yield 53%). Mass spectrum m/z, theoretical value 657.18; measured value M+H: 658.25.

Synthesis of compound 1-49-6

Compound 1-49-4 (0.352 g, 1 mmoL) and compound 1-49-5 (0.269 g, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was heated under reflux for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:5, to obtain product 1-49-6 (179 mg, yield 33%). Mass spectrum m/z, theoretical value 539.30; measured value M+H: 540.36.

Synthesis of compound 1-49-7

Compound 1-49-3 (0.659 g, 1 mmoL) and compound 1-49-6 (0.540 g, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. The reaction system was heated under reflux for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:7, to obtain product 1-49-7 (412 mg, yield 37%). Mass spectrum m/z, theoretical value 1116.56; measured value M+H: 1117.61.

Synthesis of Compound 1-49

Under nitrogen atmosphere and zero temperature, tert-butyl lithium (1.25 mL, 1.6 M pentane solution, 2 mmoL) was slowly added dropwise to a solution of compound 1-49-7 (1118 mg, 1 mmoL) in tert-butylbenzene (100 mL). After the system was reacted at 60°C for 4 hours, the temperature was lowered to -50°C, and then BBr ₃ (494 mg, 2 mmoL) was added. After reacting at room temperature for 1 hour, N,N-diisopropylethylamine (259 mg, 2 mmoL) was added. The temperature was then raised to 120°C for 12 hours. After cooling to room temperature, 5 mL of sodium acetate aqueous solution (1 M) was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the obtained crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:8, to obtain product 1-49 (297 mg, yield 27%). Mass spectrum m/z, theoretical value 1090.58; measured value M+H: 1091.64.

Example 1-4: Synthesis of Compound 1-6

Compound 1-6

Referring to the synthetic route of compound 1-4, the yield of the final product was 26%. Mass spectrum m/z, theoretical value 1034.52; measured value M+H: 1035.57.

Example 1-5: Synthesis of Compound 1-8

Compound 1-8

Referring to the synthetic route of compound 1-4, the yield of the final product was 27%. Mass spectrum m/z, theoretical value 1090.58; measured value M+H: 1091.65.

Example 1-6: Synthesis of Compound 1-16

Compound 1-16

Referring to the synthetic route of compound 1-4, the yield of the final product was 34%. Mass spectrum m/z, theoretical value 1066.58; measured value M+H: 1067.62.

Example 1-7: Synthesis of Compound 1-34

Compound 1-34

Referring to the synthetic route of compound 1-53, the yield of the final product was 32%. Mass spectrum m/z, theoretical value 1014.55; measured value M+H: 1015.61.

Example 1-8: Synthesis of Compound 1-45

Compound 1-45

Referring to the synthetic route of compound 1-4, the yield of the final product was 31%. Mass spectrum m/z, theoretical value 1090.58; measured value M+H: 1091.61.

Example 1-9: Synthesis of Compound 1-46

Compound 1-46

Referring to the synthetic route of compound 1-49, the yield of the final product was 27%. Mass spectrum m/z, theoretical value 1070.61; measured value M+H: 1071.65.

Example 1-10: Synthesis of Compound 1-117

Compound 1-117

Referring to the synthetic route of compound 1-4, the yield of the final product was 24%. Mass spectrum m/z, theoretical value 1034.52; measured value M+H: 1035.56.

Example 1-11: Synthesis of Compound 1-14

Compound 1-14

Compound 1-14 was synthesized by referring to the synthetic route of compound 1-4. The yield of the final product was 26%. Mass spectrum m/z, theoretical value 1181.63; measured value M+H: 1182.66.

Example 1-12: Synthesis of Compound 1-20

Compound 1-20

Referring to the synthetic route of compound 1-4, compound 1-20 was synthesized. The yield of the final product was 28%. Mass spectrum m/z, theoretical value 1184.56; measured value M+H: 1185.61.

Example 1-13: Synthesis of Compound 1-68

Compound 1-68

Compound 1-68 was synthesized by referring to the synthetic route of compound 1-4. The yield of the final product was 32%. Mass spectrum m/z, theoretical value 1182.52; measured value M+H: 1183.56.

Example 1-14: Synthesis of Compound 1-97

Compound 1-97

Compound 1-97 was synthesized by referring to the synthetic route of compound 1-4. The yield of the final product was 33%. Mass spectrum m/z, theoretical value 1048.50; measured value M+H: 1049.54.

Example 1-15: Synthesis of Compound 1-122

Compound 1-122

Referring to the synthetic route of compound 1-4, compound 1-122 was synthesized. The yield of the final product was 30%. Mass spectrum m/z, theoretical value 1019.48; measured value M+H: 1020.53.

Example 1-16: Synthesis of Compound 1-156

Compound 1-156

Referring to the synthetic route of compound 1-4, compound 1-156 was synthesized. The yield of the final product was 28%. Mass spectrum m/z, theoretical value 1031.48; measured value M+H: 1032.52.

As a reference preparation method for a device embodiment, the present invention evaporates a p-doped material on the surface of an ITO glass with a light-emitting area of 2 mm×2 mm or on an anode, or co-evaporates the p-doped material with a hole transport material at a concentration of 1% to 50% to form a 5-100 nm hole injection layer (HIL), forms a 5-200 nm hole transport layer (HTL) on the hole injection layer, and then co-evaporates a host material and a silicon-containing compound (guest material) prepared by the present invention on the hole transport layer at a volume ratio of 3:97 to form a 10-100 nm light-emitting layer (EML), and finally co-evaporates to form a 35 nm electron transport layer (ETL), and then evaporates 70 nm of cathode Al to manufacture an organic electroluminescent diode.

In a preferred specific embodiment, the structure of the bottom-emitting OLED device provided by the present invention is: glass containing ITO is the anode, and HIL is evaporated in sequence, with a thickness of 10 nanometers; HTL is HT-1, with a thickness of 90 nanometers; EBL is HT-8, with a thickness of 10 nanometers, and EML is the main material (H-1): the silicon-containing compound 53 (97:3, v/v%) provided by the present invention, with a thickness of 35 nanometers, and ETL is ET-3:LiQ (50:50, v/v%), with a thickness of 35 nanometers, and then the cathode Al is evaporated to 70 nanometers to prepare an organic electroluminescent diode, which is recorded as Application Example 1.

Referring to the method provided in Application Example 1, the prepared silicon-containing compound 1-4, compound 1-49, compound 1-6, compound 1-8, compound 1-16, compound 1-34, compound 1-45, compound 1-46, compound 1-117, compound 1-14, compound 1-20, compound 1-68, compound 1-97, compound 1-122, and compound 1-156 are selected as implementation objects to replace compound 1-53, and they are co-evaporated with the main material compound in a volume ratio of 3:97 to form a light-emitting layer to prepare organic electroluminescent diodes, which are recorded as Application Examples 2 to Application Examples 16.

Comparative Examples 1-2 were prepared by referring to the method provided in Application Example 1, except that BN-1 and BN-2 were used as guest materials of the light-emitting layer in Comparative Examples 1-2 to replace the silicon-containing compound of the present invention. The chemical structures of the compounds BN-1 and BN-2 in the comparative examples are as follows:

The current efficiency, voltage, life and other characteristics of the device embodiments and comparative examples prepared above were tested by standard methods, and the device luminescence characteristic data are shown in Table 1-1.

Table 1-1. Device luminescence characteristics data table

As can be seen from Table 1, compared with Comparative Example 1 and Comparative Example 2, Application Examples 1 to 16 all show good device performance in terms of current efficiency and lifespan. The improvement in the performance of each device application example is based on the fact that the silicon-containing compound material of the present invention has better electron transport capability. Furthermore, it is used as the main material of the light-emitting layer to prepare an electronic device, which has higher current efficiency and lifespan while reducing the driving voltage. This shows that the silicon-containing compound provided by the present invention has certain commercial application value. 202310507443.9

202310753983.5 The content of the present invention is described in detail below. The description of the constituent elements recorded below is sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. The present disclosure can be more easily understood by referring to the following specific embodiments and the examples contained therein. Before disclosing and describing the compounds, devices and/or methods of the present invention, it should be understood that, unless otherwise stated, they are not limited to specific synthetic methods or specific reagents, as this can vary. It should also be understood that the terms used in the present invention are only used to describe specific aspects and are not intended to be limiting. Although any methods and materials similar or equivalent to those described in the present invention can be used in the practice or experiment, exemplary methods and materials are now described.

The "C1-C12 alkyl" of the present invention refers to a monovalent alkyl group having 1-12 carbon atoms, preferably 1-10 carbon atoms, more preferably 1-6 carbon atoms. Examples of the term include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-hexyl, etc.

The "C3-C20 cycloalkyl" of the present invention refers to a cycloalkyl having 3-20 carbon atoms and a monocyclic or polycyclic condensed ring, which may be substituted by 1-3 alkyl groups. Such cycloalkyl groups include, for example, monocyclic structures such as cyclopropyl, cyclobutyl, cyclopentyl, cyclooctyl, 1-methylcyclopropyl, 2-methylcyclopentyl, 2-methylcyclooctyl, etc., or polycyclic structures such as adamantyl, etc.

The "C6-C30 aryl" of the present invention refers to an unsaturated aromatic carbocyclic ring having 6-30 carbon atoms and having a monocyclic (such as phenyl) or polycyclic condensation (such as naphthyl or anthracenyl). Preferred aryl groups include phenyl, naphthyl, etc. Unless otherwise defined for individual substituents, such aryl groups may be optionally substituted by 1-3 of the following substituents: hydroxyl, acyl, acyloxy, alkyl, alkoxy, alkenyl, alkynyl, amino, aminoacyl, aryl, aryloxy, carboxyl, carboxyl ester, aminocarboxyl ester, cyano, halogen, nitro, heteroaryl, heterocycle, thioalkoxy, trihalomethyl, etc. Preferred substituents include alkyl, alkoxy, halogen, cyano, nitro, trihalomethyl and thioalkoxy. But not limited thereto.

The "C6-C30 heteroaryl group" mentioned in the present invention refers to a general term for groups in which one or more aromatic carbon atoms in the aromatic group are replaced by heteroatoms, wherein the heteroatoms include but are not limited to oxygen, sulfur or nitrogen atoms, and the heteroaryl group may be a monocyclic heteroaryl group or a condensed-ring heteroaryl group. Examples may include pyridyl, pyrrolyl, pyridyl, thienyl, furyl, indolyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc., but are not limited thereto.

As used in the specification and the appended claims, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise. Unless otherwise stated, all commercial reagents involved in the following experiments were used directly after purchase.

In a preferred embodiment of the present invention, the OLED device of the present invention contains a hole transport layer, and the hole transport material can be preferably selected from known or unknown materials, and is particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures (Ph is phenyl):

In a preferred embodiment of the present invention, the hole injection layer contained in the OLED device of the present invention. The preferred hole injection layer material of the present invention is the following structure, but it does not mean that the present invention is limited to the following structure:

In a preferred embodiment of the present invention, the electron transport layer can be selected from at least one of the following compounds, but it does not mean that the present invention is limited to the following structures:

The OLED device of the present invention contains a host material, which can be selected from known or unknown materials, and is particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures:

The preparation method of the narrow emission compound, i.e., the guest compound, and the luminescent properties of the device are explained in detail in conjunction with the following examples.

Synthesis route:

Synthesis of compound 2-4-3: Compound 2-4-1 (300 mg, 1 mmoL) and compound 2-4-2 (274 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, 10 mL sodium carbonate aqueous solution (2 M) and tetrakis(triphenylphosphine)palladium (57 mg, 0.05 mmoL) were added. After reflux for 48 hours, the reaction system was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:10, to obtain product 4-3 (210 mg, yield 52%). Mass spectrum m/z, theoretical value 402.04; measured value M+H: 403.06.

Synthesis of compound 2-4-5: Compound 2-4-3 (402 mg, 1 mmoL) and compound 2-4-4 (225 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. After reflux for 72 hours, the reaction system was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:4, to obtain product 2-4-5 (320 mg, yield 59%). Mass spectrum m/z, theoretical value 547.27; measured value M+H: 548.29.

Synthesis of compound 2-4-7: Compound 2-4-5 (547 mg, 1 mmoL) and compound 2-4-6 (338 mg, 1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (192 mg, 2 mmoL), palladium acetate (12 mg, 0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmoL) were added. After reflux for 72 hours, the reaction system was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:4, to obtain product 2-4-7 (290 mg, yield 38%). Mass spectrum m/z, theoretical value 757.27; measured value M+H: 758.30.

Synthesis of compound 2-4-9: Compound 2-4-7 (757 mg, 1 mmoL) and compound 2-4-8 (279 mg, 1 mmoL) were dissolved in 50 mL DMF solution. Cesium carbonate (326 mg, 1 mmol) was added under nitrogen atmosphere. The reaction system was heated at 120°C for 36 hours and then cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:5, to obtain product 2-4-9 (608 mg, yield 60%). Mass spectrum m/z, theoretical value 1016.46; measured value M+H: 1016.48.

Synthesis of compound 2-4: Compound 2-4-9 (1.016 g, 1 mmoL) was dissolved in 60 mL of anhydrous tert-butylbenzene. The reaction system was cooled to -78°C, and BuLi (1 mL, 2 mmoL, 2M in hexane) was slowly added. After reacting at -78°C for 4 hours, BBr ₃ (247 mg, 1 mmoL) was slowly added. After reacting at -50°C for 1 hour, the mixture was warmed to room temperature, and then N,N-diisopropylethylamine (387 mg, 3 mmoL) was added, followed by heating to 120°C for 12 hours. After cooling to room temperature, 5 mL of sodium acetate aqueous solution (1 M) was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:8, to obtain product 2-4 (310 mg, yield 33%). Mass spectrum m/z, theoretical value 946.54; measured value M+H: 947.57.

Example 2: Synthesis of Compound 2-9

Referring to the synthetic route of compound 2-4, compound 2-9 was synthesized. The yield of the final product was 27%. Mass spectrum m/z, theoretical value 1058.67; measured value M+H: 1058.70.

Example 3: Synthesis of Compound 2-11

Compound 2-11 was synthesized by referring to the synthetic route of compound 2-4. The yield of the final product was 26%. Mass spectrum m/z, theoretical value 1174.63; measured value M+H: 1175.67.

Example 4: Synthesis of Compound 2-22

Compound 2-22 was synthesized by referring to the synthetic route of compound 2-4. The yield of the final product was 22%. Mass spectrum m/z, theoretical value 1114.73; measured value M+H: 1115.77.

Example 5: Synthesis of Compound 2-53

Compound 2-53 was synthesized by referring to the synthetic route of compound 2-4. The yield of the final product was 40%. Mass spectrum m/z, theoretical value 1181.42; measured value M+H: 1182.44.

Example 6: Synthesis of Compound 2-63

Referring to the synthetic route of compound 2-4, compound 2-63 was synthesized. The yield of the final product was 31%. Mass spectrum m/z, theoretical value 1247.54; measured value M+H: 1248.56.

Example 7: Synthesis of Compound 2-69

Compound 2-69 was synthesized by referring to the synthetic route of compound 2-4. The yield of the final product was 36%. Mass spectrum m/z, theoretical value 1154.39; measured value M+H: 1155.41.

Example 8: Synthesis of Compound 2-86

Compound 2-86 was synthesized by referring to the synthetic route of compound 2-4. The yield of the final product was 31%. Mass spectrum m/z, theoretical value 1114.73; measured value M+H: 1115.75.

Example 9: Synthesis of Compound 2-91

Compound 2-91 was synthesized by referring to the synthetic route of compound 2-4. The yield of the final product was 25%. Mass spectrum m/z, theoretical value 1115.33; measured value M+H: 1116.35.

Example 10: Synthesis of Compound 2-100

Referring to the synthetic route of compound 2-4, compound 2-100 was synthesized. The yield of the final product was 25%. Mass spectrum m/z, theoretical value 1190.64; measured value M+H: 1191.66.

Example 11: Synthesis of Compound 2-103

Compound 2-103 was synthesized by referring to the synthetic route of compound 2-4. The yield of the final product was 31%. Mass spectrum m/z, theoretical value 1115.72; measured value M+H: 1116.75.

Example 12: Synthesis of Compound 2-104

Compound 2-104 was synthesized by referring to the synthetic route of compound 2-4. The yield of the final product was 26%. Mass spectrum m/z, theoretical value 1119.57; measured value M+H: 1120.59.

Example 13: Synthesis of Compound 2-106

Referring to the synthetic route of compound 2-4, compound 2-106 was synthesized. The yield of the final product was 23%. Mass spectrum m/z, theoretical value 869.49; measured value M+H: 870.52.

Example 14: Synthesis of Compound 2-108

Compound 2-108 was synthesized by referring to the synthetic route of compound 4. The yield of the final product was 28%. Mass spectrum m/z, theoretical value 945.52; measured value M+H: 946.54.

Example 15: Synthesis of Compound 2-114

Referring to the synthetic route of compound 2-4, compound 2-114 was synthesized. The yield of the final product was 36%. Mass spectrum m/z, theoretical value 1047.57; measured value M+H: 1048.59.

Example 16: Synthesis of Compound 2-122

Referring to the synthetic route of compound 2-4, compound 2-122 was synthesized. The yield of the final product was 27%. Mass spectrum m/z, theoretical value 1003.60; measured value M+H: 1004.63.

Example 17: Synthesis of Compound 2-126

Referring to the synthetic route of compound 2-4, compound 2-126 was synthesized. The yield of the final product was 34%. Mass spectrum m/z, theoretical value 960.52; measured value M+H: 961.54.

Example 18: Synthesis of Compound 2-140

Referring to the synthetic route of compound 2-4, compound 2-140 was synthesized. The yield of the final product was 36%. Mass spectrum m/z, theoretical value 1115.72; measured value M+H: 1116.74.

Example 19: Synthesis of Compound 2-152

Referring to the synthetic route of compound 2-4, compound 2-152 was synthesized. The yield of the final product was 27%. Mass spectrum m/z, theoretical value 802.30; measured value M+H: 803.32.

Example 20: Synthesis of Compound 2-156

Referring to the synthetic route of compound 2-4, compound 2-156 was synthesized. The yield of the final product was 33%. Mass spectrum m/z, theoretical value 1209.61; measured value M+H: 1210.64.

Example 21: Synthesis of Compound 2-159

Referring to the synthetic route of compound 2-4, compound 2-159 was synthesized. The yield of the final product was 41%. Mass spectrum m/z, theoretical value 1159.57; measured value M+H: 1160.59.

Example 22: Synthesis of Compound 2-163

Referring to the synthetic route of compound 2-4, compound 2-163 was synthesized. The yield of the final product was 26%. Mass spectrum m/z, theoretical value 1080.64; measured value M+H: 1081.67.

Example 23: Synthesis of Compound 2-175

Referring to the synthetic route of compound 2-4, compound 2-175 was synthesized. The yield of the final product was 35%. Mass spectrum m/z, theoretical value 1078.52; measured value M+H: 1079.54.

Example 24: Synthesis of Compound 2-183

Compound 2-183 was synthesized by referring to the synthetic route of compound 2-4. The yield of the final product was 27%. Mass spectrum m/z, theoretical value 1251.66; measured value M+H: 1252.68.

Example 25: Synthesis of Compound 2-190

Referring to the synthetic route of compound 2-4, compound 2-190 was synthesized. The yield of the final product was 31%. Mass spectrum m/z, theoretical value 1209.70; measured value M+H: 1210.73.

Example 26: Synthesis of Compound 2-202

Compound 2-202 was synthesized by referring to the synthetic route of compound 2-4. The yield of the final product was 34%. Mass spectrum m/z, theoretical value 1092.62; measured value M+H: 1093.64.

Example 27: Synthesis of Compound 2-204

Referring to the synthetic route of compound 2-4, compound 2-204 was synthesized. The yield of the final product was 28%. Mass spectrum m/z, theoretical value 921.47; measured value M+H: 922.51.

As a reference preparation method for a device embodiment, the present invention evaporates a p-doped material on the surface of an ITO glass with a light-emitting area of 2 mm×2 mm or on an anode, or co-evaporates the p-doped material with a hole transport material at a concentration of 1% to 50% to form a 5-100 nm hole injection layer (HIL), forms a 5-200 nm hole transport layer (HTL) on the hole injection layer, and then co-evaporates a host material and a compound prepared by the present invention (guest material) on the hole transport layer at a volume ratio of 3:97 to form a 10-100 nm light-emitting layer (EML), and finally co-evaporates to form a 35 nm electron transport layer (ETL), and then evaporates 70 nm of cathode Al to manufacture an organic electroluminescent diode.

In a preferred specific embodiment, the structure of the bottom-emitting OLED device provided by the present invention is: glass containing ITO is the anode, and HIL is evaporated in sequence, with a thickness of 10 nanometers; HTL is HT-1, with a thickness of 90 nanometers; EBL is HT-8, with a thickness of 10 nanometers, and EML is the main material (H-1): the narrow emission compound 2-4 (97:3, v/v%) provided by the present invention, with a thickness of 35 nanometers, and ETL is ET-3:LiQ (50:50, v/v%), with a thickness of 35 nanometers, and then the cathode Al is evaporated to 70 nanometers to prepare an organic electroluminescent diode, which is recorded as Application Example 1.

Referring to the method provided in Application Example 1, the prepared compounds 2-9, 2-11, 2-22, 2-48, 2-53, 2-63, 2-69, 2-72, 2-77, 2-85, 2-91, 2-100, 2-103, 2-104, 2-106, 2-108, 2-114, 2-12 2. Compound 2-126, compound 2-140, compound 2-152, compound 2-156, compound 2-159, compound 2-163, compound 2-175, compound 2-183, compound 2-190, compound 2-202, and compound 2-204 were used as the implementation objects to replace compound 2-4, and they were co-evaporated with the main material compound H-1 in a volume ratio of 3:97 to form a light-emitting layer to prepare an organic electroluminescent diode, which is recorded as Application Example 2 to Application Example 27.

Comparative Example 1 was prepared by referring to the method provided in the above Application Example 1, except that BN-1 was used as the guest material of the light-emitting layer in Comparative Example 1 to replace the compound of the present invention. The chemical structure of the compound BN-1 in the comparative example is as follows: The molecular structure formula of the related materials is as follows:

The current efficiency, full width at half maximum (FWHM), driving voltage, lifespan and other characteristics of the device embodiments and comparative examples prepared above were tested by standard methods, and the device luminescence characteristic data are shown in Table 2-1.

Table 2-1. Device luminescence characteristics data table

As can be seen from Table 1, compared with Comparative Example 1, Application Examples 1 to 27 all show good device performance in terms of current efficiency and lifespan. The performance improvement of each device application example is based on the fact that the compound material of the present invention has a better inhibitory effect on aggregation-induced quenching. Furthermore, it is used as the main material of the light-emitting layer to prepare an electronic device, which has higher current efficiency and lifespan while reducing the driving voltage. It is an organic light-emitting functional material with good performance and great commercial promotion value. 202310753983.5

202311482550.7 The following will be a clear and complete description of the technical solutions in conjunction with the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present invention.

The aromatic group described in the present invention refers to a general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic hydrocarbon molecule. It can be a monocyclic aromatic group or a condensed aromatic group. Examples may include phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl or pyrene, but are not limited thereto.

The heteroaryl group described in the present invention refers to a general term for groups in which one or more aromatic carbon atoms in an aromatic group are replaced by heteroatoms, wherein the heteroatoms include but are not limited to oxygen, sulfur or nitrogen atoms. The heteroaryl group may be a monocyclic heteroaryl group or a condensed ring heteroaryl group. Examples may include pyridyl, pyrrolyl, pyridyl, thienyl, furyl, indolyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc., but are not limited thereto.

Throughout the specification, unless explicitly described to the contrary, "comprising" any component will be understood to imply the inclusion of other elements, rather than excluding any other elements. In addition, it should be understood that throughout the specification, when an element such as a layer, film, region or substrate is referred to as being "on" or "above" another element, it can be "directly on" another element, or there may be intervening elements. In addition, "on..." or "above..." means being located above the target portion, and does not necessarily mean being located above according to the direction of gravity.

An object of the present invention is to provide an organic electroluminescent device, which includes: a substrate layer; a first electrode, which is on the substrate; an organic light-emitting functional layer, which is on the first electrode; a second electrode, which is on the organic light-emitting functional layer; the organic light-emitting functional layer includes a light-emitting layer, and the light-emitting layer includes an organic compound with an anthracene ring structure.

In one embodiment of the present invention, the light-emitting layer in the organic electroluminescent (OLED) device contains one or more components of the compound represented by the above general formula (I) as the light-emitting main material; and also contains one or more components of the compound represented by the above general formula (Ш) as the light-emitting doping material.

In a preferred embodiment of the present invention, an OLED is provided, which includes a substrate, an anode, a cathode, and an organic light-emitting functional layer, wherein the organic light-emitting functional layer may include a light-emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, etc., or may only include a light-emitting layer and one or more other layers; wherein the light-emitting layer comprises one or more of the compounds represented by the above general formula (I); preferably, it also comprises one or more compounds of the general formula (Ш). Optionally, there is a covering layer, a protective layer and/or an encapsulation layer on the organic light-emitting functional layer.

The substrate of the present invention can be any substrate used in a typical organic light-emitting device. It can be a glass or transparent plastic substrate, or a substrate of an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and waterproofness. Depending on the properties of the substrate, the use direction is different.

As materials for the hole injection layer, the hole transport layer, and the electron injection layer, any material can be selected from known related materials used for OLED devices.

As a guest material capable of producing blue fluorescence, green fluorescence and blue-green fluorescence, it not only needs to have an extremely high fluorescence quantum luminescence efficiency, but also needs to have an appropriate energy level to effectively absorb the excitation energy of the host material to emit light.

The present invention is described in detail below in conjunction with specific examples. Synthesis Examples All raw materials and solvents are commercially available unless otherwise specified, and the solvents are used directly without further treatment.

Example

Example 1: Synthesis of Compound 3-1-031

Synthesis route:

1) In a three-necked reaction flask, 1-031-1 (15 mmoL) and 1-031-2 (15 mmoL) were dissolved in 150 mL of 1,4-dioxane, and K ₂ CO ₃ (20 mmoL) dissolved in 100 mL of H ₂ O was added. Pd(P(t-Bu) ₃ ) ₂ (0.15 mmoL) was then added, and the mixture was stirred for 5 hours under argon reflux. After the reaction was completed and cooled to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain the intermediate product 1-031-3.

2) In a double-necked reaction flask, add the intermediate product 1-031-3 (10 mmol), N-bromosuccinimide (NBS) (12 mmol) and 100 mL of dimethylformamide (DMF), and stir for 10 hours under an argon atmosphere at room temperature. After the reaction is completed, transfer the reaction solution to a separatory funnel and extract with water and ethyl acetate. Dry the extract with MgSO ₄ , filter and concentrate, and finally purify the sample by silica gel column chromatography to obtain the intermediate product 1-031-4.

3) In a three-necked reaction flask, 1-031-4 (6 mmoL) and 1-031-5 (6 mmoL) were dissolved in 150 mL of 1,4-dioxane, and K ₂ CO ₃ (20 mmoL) dissolved in 100 mL of H ₂ O was added. Pd(P(t-Bu) ₃ ) ₂ (0.06 mmoL) was then added, and the mixture was stirred for 5 hours under argon reflux. After the reaction was completed and cooled to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO ₄ , filtered and concentrated, and finally the sample was purified by silica gel column chromatography to obtain the final product 1-031. Test the structure of the target product 3-1-031: LC-MS (m/z) (M+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 596.21, and the test value was 596.49.

Example 2: Synthesis of Compound 3-1-003

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-003 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 496.18 and the test value was 496.48.

Example 3: Synthesis of Compound 3-1-004

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-004 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 546.20 and the test value was 546.54.

Example 4: Synthesis of Compound 3-1-005

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-005 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 470.17 and the test value was 470.49.

Example 5: Synthesis of Compound 3-1-019

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-019 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 520.18 and the test value was 520.52.

Example 6: Synthesis of Compound 3-1-022

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-022 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 596.21 and the test value was 596.49.

Example 7: Synthesis of Compound 3-1-025

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-025 was synthesized, and LC-MS (m/z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 646.23, and the test value was 646.56.

Example 8: Synthesis of Compound 3-1-032

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-032 was synthesized, and LC-MS (m/z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 570.20, and the test value was 570.53.

Example 9: Synthesis of Compound 3-1-036

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-036 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 546.20 and the test value was 546.48.

Example 10: Synthesis of Compound 3-1-037

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-037 was synthesized, and LC-MS (m/z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 596.21, and the test value was 596.54.

Example 11: Synthesis of Compound 3-1-050

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-050 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 546.20 and the test value was 546.55.

Example 12: Synthesis of Compound 3-1-051

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-051 was synthesized, and LC-MS (m/z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 622.23, and the test value was 622.64.

Example 13: Synthesis of Compound 3-1-053:

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-053 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 572.21 and the test value was 572.51.

Example 14: Synthesis of Compound 3-1-054

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-054 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 596.21 and the test value was 596.61.

Example 15: Synthesis of Compound 3-1-058

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-058 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 520.18 and the test value was 520.53.

Example 16: Synthesis of Compound 3-1-061

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-061 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 560.18 and the test value was 560.62.

Example 17: Synthesis of Compound 3-1-062

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-062 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 510.16 and the test value was 510.45.

Example 18: Synthesis of Compound 3-1-064

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-064 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 686.22 and the test value was 686.63.

Example 19: Synthesis of Compound 1-065

Referring to the synthesis steps and reaction conditions of Example 1, compound 1-065 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 636.21 and the test value was 636.56.

Example 20: Synthesis of Compound 3-1-068

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-068 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 610.19 and the test value was 610.48.

Example 21: Synthesis of Compound 3-1-103

Referring to the synthesis steps and reaction conditions of Example 1, compound 3-1-103 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 586.19 and the test value was 586.47.

Example 22: Synthesis of Compound 3-1-165

Synthesis route:

1) In a three-necked reaction flask, 1-165-1 (15 mmoL) and 1-165-2 (15 mmoL) were dissolved in 150 mL of 1,4-dioxane, and K ₂ CO ₃ (20 mmoL) dissolved in 100 mL of H ₂ O was added. Pd(P(t-Bu) ₃ ) ₂ (0.15 mmoL) was then added, and the mixture was stirred for 5 hours under argon reflux. After the reaction was completed and cooled to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain the intermediate product 1-165-3.

2) In a double-necked reaction flask, add the intermediate product 1-165-3 (10 mmol), N-bromosuccinimide (NBS) (12 mmol) and 100 mL of dimethylformamide (DMF), and stir for 10 hours under an argon atmosphere at room temperature. After the reaction is completed, transfer the reaction solution to a separatory funnel and extract with water and ethyl acetate. Dry the extract with MgSO ₄ , filter and concentrate, and finally purify the sample by silica gel column chromatography to obtain the intermediate product 1-165-4.

3) In a three-necked reaction flask, 1-165-4 (6 mmoL) and 1-165-5 (6 mmoL) were dissolved in 150 mL of 1,4-dioxane, and K ₂ CO ₃ (20 mmoL) dissolved in 100 mL of H ₂ O was added. Pd(P(t-Bu) ₃ ) ₂ (0.06 mmoL) was then added, and the mixture was stirred for 5 hours under argon reflux. After the reaction was completed and cooled to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO ₄ , filtered and concentrated, and the sample was purified by silica gel column chromatography to obtain the final product 3-1-165. Test the structure of the target product 3-1-165: LC-MS (m/z) (M+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 518.21, and the test value was 518.53.

Example 23: Synthesis of Compound 3-1-108

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-108 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 618.24 and the test value was 618.57.

Example 24: Synthesis of Compound 3-1-110

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-110 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 594.24 and the test value was 594.61.

Example 25: Synthesis of Compound 3-1-111

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-111 was synthesized, and LC-MS (m/z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 644.26, and the test value was 644.57.

Example 26: Synthesis of Compound 3-1-115

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-115 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 568.23 and the test value was 568.58.

Example 27: Synthesis of Compound 3-1-124

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-124 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 694.27 and the test value was 694.64.

Example 28: Synthesis of Compound 3-1-132

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-132 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 654.28 and the test value was 654.65.

Example 29: Synthesis of Compound 3-1-137

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-137 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z)(Μ+): the theoretical value was 604.26 and the test value was 604.66.

Example 30: Synthesis of Compound 3-1-139

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-139 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 578.25 and the test value was 578.58.

Example 31: Synthesis of Compound 3-1-140

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-140 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 554.25 and the test value was 554.62.

Example 32: Synthesis of Compound 3-1-151

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-151 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z)(Μ+): the theoretical value was 528.23 and the test value was 528.63.

Example 33: Synthesis of Compound 3-1-171

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-171 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z)(Μ+): the theoretical value was 478.22 and the test value was 478.52.

Example 34: Synthesis of Compound 3-1-173

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-173 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 475.20 and the test value was 475.48.

Example 35: Synthesis of Compound 3-1-174

Referring to the synthesis steps and reaction conditions of Example 22, compound 3-1-174 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 505.24 and the test value was 505.58.

Example 36: Synthesis of Compound 3-2-009

Synthesis route:

  

1) Compound 3-2-009-1 (1 mmoL) and compound 3-2-009-2 (1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added. After the reaction system was refluxed for 72 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography column, eluent: dichloromethane: petroleum ether = 1:4, intermediate product 3-2-009-3.

2) The intermediate product 3-2-009-3 (1 mmoL) and compound 3-2-009-4 (1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added. After the reaction system was refluxed for 72 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography column, eluent: dichloromethane: petroleum ether = 1:4, intermediate product 3-2-009-5.

3) The intermediate product 3-2-009-5 (1 mmoL) and compound 3-2-009-6 (1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added. After the reaction system was refluxed for 72 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography column, eluent: dichloromethane: petroleum ether = 1:4, intermediate product 3-2-009-7.

4) The intermediate product 3-2-009-7 (1 mmoL) and compound 3-2-009-8 (1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added. After the reaction system was refluxed for 72 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography column, eluent: dichloromethane: petroleum ether = 1:4, intermediate product 3-2-009-9.

5) The intermediate product 3-2-009-9 (1 mmoL) was dissolved in 60 mL of anhydrous tert-butylbenzene. The reaction system was cooled to ‑78°C, and BuLi (1 mL, 2 mmoL, 2M in hexane) was slowly added. After reacting at ‑78°C for 4 hours, BBr (3247 mg, 1 mmoL) was slowly added. After reacting at ‑50°C for 1 hour, the mixture was warmed to room temperature, and then N,N-diisopropylethylamine (387 mg, 3 mmoL) was added, followed by heating to 120°C for 12 hours. After cooling to room temperature, 5 mL of sodium acetate aqueous solution (1 M) was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:8, to obtain the final product 3-2-009. The structure of the test target product 3-2-009: LC-MS (m/z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value is 1107.53, and the test value is 1107.97.

Example 37: Synthesis of Compound 3-2-001

Referring to the synthesis steps and reaction conditions of Example 36, compound 3-2-001 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 686.22 and the test value was 686.63.

Example 38: Synthesis of Compound 3-2-004

Referring to the synthesis steps and reaction conditions of Example 36, compound 3-2-004 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 686.22 and the test value was 686.63.

Example 39: Synthesis of Compound 3-2-005

Referring to the synthesis steps and reaction conditions of Example 36, compound 3-2-005 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 686.22 and the test value was 686.63.

Example 40: Synthesis of Compound 3-2-008

Referring to the synthesis steps and reaction conditions of Example 36, compound 3-2-008 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 686.22 and the test value was 686.63.

Example 41: Synthesis of Compound 3-2-012

Referring to the synthesis steps and reaction conditions of Example 36, compound 3-2-012 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1125.52 and the test value was 1125.86.

Example 42: Synthesis of Compound 3-2-013

Referring to the synthesis steps and reaction conditions of Example 36, compound 3-2-013 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1058.52 and the test value was 1058.86.

Example 43: Synthesis of Compound 3-2-016

Referring to the synthesis steps and reaction conditions of Example 36, compound 3-2-016 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1024.57 and the test value was 1024.93.

Example 44: Synthesis of Compound 3-2-017

Referring to the synthesis steps and reaction conditions of Example 36, compound 3-2-017 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1024.57 and the test value was 1024.93.

Example 45: Synthesis of Compound 3-2-020

Referring to the synthesis steps and reaction conditions of Example 36, compound 3-2-020 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1201.59 and the test value was 1201.87.

Example 46: Synthesis of Compound 3-2-021

Referring to the synthesis steps and reaction conditions of Example 36, compound 3-2-021 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1201.59 and the test value was 1201.87.

Example 47: Synthesis of Compound 3-2-025

Referring to the synthesis steps and reaction conditions of Example 36, compound 3-2-025 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1201.59 and the test value was 1201.87.

Example 48: Synthesis of Compound 3-2-029

Referring to the synthesis steps and reaction conditions of Example 36, compound 3-2-029 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1201.59 and the test value was 1201.87.

Example 49: Synthesis of Compound 3-2-036

Synthesis route:

    

1) Compound 3-2-036-1 (1 mmoL) and compound 3-2-036-2 (1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added. After the reaction system was refluxed for 72 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:4, intermediate product 3-2-036-3.

2) The intermediate product 3-2-036-3 (1 mmoL) and compound 3-2-036-4 (1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added. After the reaction system was refluxed for 72 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography column, eluent: dichloromethane: petroleum ether = 1:4, intermediate product 3-2-036-5.

3) The intermediate product 3-2-036-5 (1 mmoL) and compound 3-2-036-6 (1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added. After the reaction system was refluxed for 72 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography column, eluent: dichloromethane: petroleum ether = 1:4, intermediate product 3-2-036-7.

4) The intermediate product 3-2-036-7 (1 mmoL) and compound 3-2-036-8 (1 mmoL) were dissolved in 50 mL toluene solution. Under nitrogen atmosphere, sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL), and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added. After the reaction system was refluxed for 72 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried with sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:4, intermediate product 3-2-036-9.

5) The intermediate product 3-2-036-9 (1 mmoL) was dissolved in 60 mL of anhydrous tert-butylbenzene. The reaction system was cooled to ‑78°C, and BuLi (1 mL, 2 mmoL, 2M in hexane) was slowly added. After reacting at ‑78°C for 4 hours, BBr (3247 mg, 1 mmoL) was slowly added. After reacting at ‑50°C for 1 hour, the mixture was warmed to room temperature, and then N,N-diisopropylethylamine (387 mg, 3 mmoL) was added, followed by heating to 120°C for 12 hours. After cooling to room temperature, 5 mL of sodium acetate aqueous solution (1 M) was added. The solvent was removed by rotary evaporation, and the residue was extracted with dichloromethane (3×100 mL). The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by vacuum distillation, and the resulting crude product was separated and purified by silica gel chromatography, eluent: dichloromethane: petroleum ether = 1:8, to obtain the final product 3-2-036. The structure of the test target product 3-2-036: LC-MS (m/z) (Μ+) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value is 1078.62, and the test value is 1078.98.

Example 50: Synthesis of Compound 3-2-033

Referring to the synthesis steps and reaction conditions of Example 49, compound 3-2-033 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1112.56 and the test value was 1112.92.

Example 51: Synthesis of Compound 3-2-038

Referring to the synthesis steps and reaction conditions of Example 49, compound 3-2-038 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1121.55 and the test value was 1121.89.

Example 52: Synthesis of Compound 3-2-040

Referring to the synthesis steps and reaction conditions of Example 49, compound 3-2-040 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1235.54 and the test value was 1235.87.

Example 53: Synthesis of Compound 3-2-042

Referring to the synthesis steps and reaction conditions of Example 49, compound 3-2-042 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1166.61 and the test value was 1166.97.

Example 54: Synthesis of Compound 3-2-044

Referring to the synthesis steps and reaction conditions of Example 49, compound 3-2-044 was synthesized and analyzed by liquid chromatography-mass spectrometry to obtain LC-MS (m/z) (Μ+): the theoretical value was 1215.57 and the test value was 1215.93.

Several examples of the application of the organic compound of the present invention in OLED devices are listed below to further illustrate the beneficial effects of the compound of the present invention. The materials used in the examples are purchased from commercial sources or synthesized by the user.

As a reference preparation method for a device embodiment, the present invention evaporates 50-500nm ITO/Ag/ITO on an alkali-free glass substrate as an anode, evaporates a hole injection layer (5nm-20nm), a hole transport layer (50-120nm), a light-emitting auxiliary layer (5-120nm), a light-emitting layer (20-50nm), an electron transport layer (20-80nm), and an electron injection layer (1-10nm) on the anode, and then co-evaporates Mg and Ag (weight ratio 10:1, 10-50nm) to make a semi-transparent cathode, and then evaporates a cover layer compound. Finally, the light-emitting device is encapsulated using an epoxy resin adhesive in a nitrogen atmosphere.

In a preferred embodiment, the structure of the OLED device provided by the present invention is: first, use an ultrasonic cleaner to wash the alkali-free glass substrate with isopropanol for 15 minutes, and then perform UV ozone cleaning in the air for 30 minutes. The treated substrate is vacuum-deposited with ITO/Ag/ITO 100nm as an anode, and then a hole injection layer (HT:PD, 10nm, 2%), a hole transport layer (NPB, 30nm), a light-emitting auxiliary layer (BP, 5nm) blue light-emitting layer (main material; doping material = compound 3-1-031: compound 3-2-009 (weight ratio 97:3, 30nm)), an electron transport layer (compound ET: Liq=1:1, 30nm), and an electron injection layer (LiF, 0.5nm) are sequentially stacked and evaporated, and Mg and Ag (weight ratio 10:1, 15nm) are co-evaporated to make a semi-transparent cathode, and then compound CPL (65nm) is evaporated as a covering layer. Finally, the light emitting device is encapsulated using epoxy resin adhesive in a nitrogen atmosphere, which is recorded as Application Example 1. The molecular structure formula of the relevant materials is as follows:

The method provided in the above-mentioned application example 1 was used to prepare application examples 2 to 35 and comparative example 1, the only difference being that the compounds listed in Table 1 were used as the main materials to replace the compound 3-1-003 in application example 1. The structure of BH-002 in comparative example 1 is as follows:

.

The current of the OLED device at different voltages was tested with a Keithley 2365A digital nanovoltmeter, and then the current was divided by the luminous area to obtain the current density of the OLED device at different voltages; the brightness and radiant energy flux density of the OLED device at different voltages were tested with a Konicaminolta CS-2000 spectroradiometer; according to the current density and brightness of the OLED device at different voltages, the working voltage Volt and current efficiency (cd/A) at the same current density (10mA/cm ² ) were obtained. BI=E/CIEy refers to the Blue Index in blue light and is also a parameter for measuring the luminous efficiency of blue light. E refers to the current efficiency, and CIEy refers to the ordinate color point obtained by bringing the wavelength of the device's luminous half-peak width into the CIE1930 software. The test data is shown in Table 3-1.

Table 3-1 Organic electroluminescent devices and electronic luminescence characteristics

It can be seen from Table 1 that, compared with Comparative Example 1, Application Examples 1 to 35 have lower operating voltage, higher BI luminous efficiency and longer service life. The performance improvement of each application example is based on the organic compound material of the present invention having better charge transport capability.

In order to further verify the excellent performance of the organic compound provided by the present invention, Application Examples 36 to 58 and Comparative Examples 2 to 5 were prepared by referring to the method provided in Application Example 1 above; the only difference is that the compounds listed in Table 2 were used as the main material and the light-emitting auxiliary material to replace the compound 3-1-031 and the compound 3-2-009 in Application Example 1. The structure of the new material involved in the comparative example in Table 2 is as follows:

.

Table 3-2. Devices and electronic luminescence characteristics of combined material applications

It can be seen from Table 2 that compared with Comparative Examples 2 to 5, Application Examples 36 to 58 have better operating voltage, higher BI luminous efficiency and longer service life. It can be seen that the compatibility of the luminescent host material and the luminescent doping material in the present invention is better, which can enable the blue light emitting layer to better achieve the balance of electron and hole transmission and exciton conversion rate, significantly reduce the power consumption of the white light device, and increase the service life of the panel. It can significantly improve the luminous efficiency of the device. 202311482550.7

Obviously, the above embodiments are merely examples for the purpose of clear explanation, and are not intended to limit the implementation methods. For those skilled in the art, other different forms of changes or modifications can be made based on the above description. It is not necessary and impossible to list all the implementation methods here. The obvious changes or modifications derived therefrom are still within the scope of protection of the invention.

Claims (18)

A luminescent compound, characterized in that the organic compound has a structure shown in the following formula (1-I) or formula 2-1: ; In formula (1-I), Ring A, Ring B, and Ring C are unsubstituted, monosubstituted, or polysubstituted aryl rings, heteroaryl rings, or heteroalkyl rings; R ₁ , R ₂ , R ₃ , R ₄ , and R ₅ represent a polysubstituted group, which is unsubstituted, monosubstituted, or polysubstituted; at least one substituent in R ₁ -R ₅ is independently selected from the group consisting of: The structure shown; In formula 2-I, E is a substituted phenyl group, and the substitution is mono- or poly-substitution; the substituents are selected from one or a combination of at least two of deuterium, Si, C1-C12 alkyl, C1-C12 azaalkyl, C6-C30 aryl, C6-C30 aromatic silicon, C6-C30 aromatic amino, and C6-C30 azaaromatic; R ₆ -R ₉ are each independently selected from one or a combination of at least two of hydrogen, N, C1-C12 alkyl, C3-C20 cycloalkyl, C6-C30 aryl, and C6-C30 aromatic amino; any two adjacent substituents are not connected or are connected to each other to form a ring structure; Z ₁ -Z ₅ are each independently represented by N or CR, and the R is independently selected from one or a combination of at least two of hydrogen, C1-C12 alkyl, C3-C20 cycloalkyl, C6-C30 aryl, and C6-C30 heteroaromatic; any two adjacent substituents are not connected or are connected to each other to form a ring structure. The luminescent compound according to claim 1, characterized in that, in formula (1-I), R ₁ -R ₅ are each independently selected from the group consisting of hydrogen, oxygen, nitrogen, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 6 to 20 carbon atoms; In formula 2-I, R ₇ and R ₈ are each independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted diphenylamine; when there are substituents, the substitution is mono- or poly-substitution, and the substituents are selected from C1-C6 alkyl or C6-C12 aryl. The luminescent compound according to claim 1, characterized in that, in formula (1-I), ring A is a benzene ring or thiophene, and ring B and ring C are benzene rings or pyridine; in formula 2-I, E is selected from the structural group shown in formula 2-2 or formula 2-3, and the hydrogen atoms in the structural group may be partially deuterated or fully deuterated: , ; Wherein, R ₁₀ and R ₁₁ are each independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamine; when containing substituents, the substituents are selected from C1-C6 alkyl and C6-C12 aryl; the dotted line indicates that it can be connected to the parent core. The luminescent compound according to claim 1, characterized in that in formula 2-I, R is selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, butyl, tert-butyl, phenyl, biphenyl, tert-butylbiphenyl, tert-butylbenzene, pyridyl or phenylpyridine, and any two adjacent substituents are not connected or are connected to each other to form a ring structure. The luminescent compound according to claim 1 is characterized in that at least one hydrogen in the compound or structure represented by formula (1-1) can be substituted by deuterium, cyano or halogen; and the hydrogen atoms in the R, R ₆ -R ₉ groups in formula 2-I can be partially or fully deuterated. The luminescent compound according to claim 1, characterized in that, in formula (1-1), R ₁ -R ₅ can be independently selected from a group comprising the following substituents; ; * is a connection point, and the group may be unsubstituted or substituted by other substituents, and other substituents may be selected from deuterium, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 6 to 20 carbon atoms; in formula 2-I, R ₆ -R ₉ are each independently selected from one or a combination of at least two of hydrogen, deuterium, methyl, ethyl, propyl, butyl, tert-butyl, phenyl, biphenyl, tert-butylbiphenyl, tert-butylbenzene, pyridyl, phenylpyridine, arylamino, and diphenylamine; any two adjacent substituents are not connected or are connected to each other to form a ring structure. The luminescent compound according to claim 1, characterized in that in formula (2-I), R ₆ and R ₉ are each independently selected from hydrogen, tert-butyl, phenyl, biphenyl, tert-butylphenyl, 3,5-di-tert-butylphenyl; and R ₁₀ and R ₁₁ are each independently selected from phenyl, tolyl, biphenyl, tert-butylphenyl, pyridine, carbazolyl or diphenyltriazine. A luminescent compound, wherein the luminescent compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium: Use of the luminescent compound according to any one of claims 1 to 8 in an electronic device. The use according to claim 9 is characterized in that the electronic device is an organic electroluminescent device, an organic integrated circuit, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic solar cell, an organic optical detector, an organic photoreceptor, an organic field quenching device, a light emitting electrochemical cell and/or an organic laser diode. A composition, characterized in that it contains the luminescent compound according to any one of claims 1 to 8. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises the luminescent compound according to any one of claims 1 to 8. The organic electroluminescent device according to claim 11, comprising a cathode, an anode and an organic functional layer therebetween; characterized in that the organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises the light-emitting compound according to any one of claims 1 to 8. A composition, characterized in that the composition comprises any one of the following chemical structures, wherein "D" represents deuterium: ; The composition further comprises a boron-nitrogen compound, wherein the boron-nitrogen compound is selected from any one of the following chemical structures, wherein "D" represents deuterium: . An organic electroluminescent device, comprising a cathode, an anode and an organic functional layer therebetween; characterized in that the organic functional layer comprises the composition as claimed in claim 14. An organic photoelectric device, comprising a first electrode, a second electrode facing the first electrode, and a light-emitting material layer arranged between the first electrode and the second electrode; characterized in that the light-emitting material layer contains the light-emitting compound according to any one of claims 1 to 8; or contains the composition according to claim 14. A preparation, characterized in that it contains the luminescent compound according to any one of claims 1 to 8 or the composition according to claim 14, and at least one solvent. A display or lighting device, characterized in that the device comprises one or more of the organic electroluminescent devices described in claim 12 or claim 15.