CN117946146A - Boron-nitrogen compound containing imidazole and derivative group, organic electroluminescent device and application - Google Patents

Boron-nitrogen compound containing imidazole and derivative group, organic electroluminescent device and application Download PDF

Info

Publication number
CN117946146A
CN117946146A CN202410353804.3A CN202410353804A CN117946146A CN 117946146 A CN117946146 A CN 117946146A CN 202410353804 A CN202410353804 A CN 202410353804A CN 117946146 A CN117946146 A CN 117946146A
Authority
CN
China
Prior art keywords
compound
boron
substituted
nitrogen compound
deuterium
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202410353804.3A
Other languages
Chinese (zh)
Inventor
赵晓宇
申屠晓波
张磊
吴空物
刘运起
孔祥贞
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zhejiang Huadisplay Optoelectronics Co Ltd
Original Assignee
Zhejiang Huadisplay Optoelectronics Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zhejiang Huadisplay Optoelectronics Co Ltd filed Critical Zhejiang Huadisplay Optoelectronics Co Ltd
Priority to CN202410353804.3A priority Critical patent/CN117946146A/en
Publication of CN117946146A publication Critical patent/CN117946146A/en
Pending legal-status Critical Current

Links

Classifications

    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Abstract

The invention relates to the technical field of organic photoelectric material preparation, in particular to a boron-nitrogen compound containing imidazole and derivative groups, an organic electroluminescent device and application thereof. The boron-nitrogen compound has good thermal stability and good electron and hole transmission capability, and can improve the energy transmission performance and exciton utilization efficiency between a host and an object and the thermal stability; the boron-nitrogen compound is used as a functional layer, particularly used as a luminescent layer to manufacture an organic electroluminescent device, so that the current efficiency is improved, the service life of the device is also greatly prolonged, and the energy is effectively transferred to the boron-nitrogen compound for luminescent instead of heating after most of electrons and holes are compounded.

Description

Boron-nitrogen compound containing imidazole and derivative group, organic electroluminescent device and application
Technical Field
The invention relates to the technical field of organic photoelectric material preparation, in particular to a boron-nitrogen compound containing imidazole and derivative groups, an organic electroluminescent device and application thereof.
Background
With the development of multimedia technology and the improvement of informatization requirements, the requirements on the performance of panel displays are higher and higher. The OLED has a series of advantages of autonomous luminescence, low-voltage direct current drive, full solidification, wide viewing angle, rich colors and the like, and is widely paid attention to potential application in a new-generation display and illumination technology, so that the OLED has a very wide application prospect. The organic electroluminescent device is a spontaneous luminescent device, and the mechanism of OLED luminescence is that electrons and holes are respectively injected from positive and negative poles and then migrate, recombine and decay in an organic material under the action of an external electric field to generate luminescence. Typical structures of OLEDs include one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer, and a light emitting layer. Although research progress of organic electroluminescence is very rapid, development of new luminescent materials is still needed, especially development and design of high-efficiency long-life luminescent host materials.
Disclosure of Invention
The invention aims at overcoming the defects of the prior art and provides a boron nitride compound containing imidazole and derivative groups, an organic electroluminescent device and application thereof. The compound improves the thermal stability of the compound by introducing imidazole and imidazole derivative groups, improves the electron and hole transmission capacity of the compound, and can effectively improve the energy transmission performance between a host and an object after a device is prepared.
In order to achieve the purpose of the invention, the technical scheme of the invention is as follows:
According to one or more embodiments, the present invention provides a boron nitride compound containing imidazole and a derivative group, the boron nitride compound having a structure represented by the following formula (I):
In formula (I), ar 1 is absent or present, when present, said Ar 1 is fused to an attached imidazole group, ar 1 is selected from substituted or unsubstituted C6-C36 aryl;
R 1、R2、R3、R4、R5 represents a polysubstituted group, which may be unsubstituted, monosubstituted or polysubstituted; in the case of being substituted with a plurality of substituents, the plurality of substituents are the same or different from each other;
Each R 1-R5 is independently selected from hydrogen, deuterium, C1-C24 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, the heteroatoms in the heteroaryl being selected from O, S; when substituted, the substituent is selected from any one or more of deuterium, C1-C24 alkyl, C3-C24 cycloalkyl and substituted or unsubstituted C6-C30 aryl.
Preferably, ar 1 is selected from one of non-existing or phenyl, methyl substituted indenyl and phenanthryl; r 2 is selected from hydrogen, methyl, ethyl, propyl, tert-butyl, phenyl, tert-butylphenyl.
Preferably, each R 1、R4 is independently selected from hydrogen, deuterium, methyl, ethyl, propyl, t-butyl, pyridinyl, adamantyl, phenyl, t-butylphenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, triphenylsilyl, substituted or unsubstituted indenyl, substituted or unsubstituted benzimidazolyl; when substituted, the substitution is selected from any one or more of deuterium, C1-C10 alkyl, C3-C14 cycloalkyl, C6-C36 aryl.
Preferably, the R 3 is selected from hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, tert-butylphenyl, di-tert-butylphenyl, biphenyl, tert-butyl substituted biphenyl, adamantyl, dibenzofuranyl, dimethylfluorenyl.
Preferably, the R 5 is selected from hydrogen, deuterium, methyl, ethyl, propyl, tertiary butyl, diphenylamino, methoxyphenyl, triphenylsilyl, dibenzofuranyl, dimethylfluorenyl, phenyl-substituted benzimidazolyl.
At least one hydrogen in the compounds of formula (I) of the present invention may be substituted with deuterium, tritium, cyano or halogen.
According to one or more embodiments, the boron nitrogen compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:
/>
/>
/>
/>
/>
。
According to one or more embodiments, the present invention also provides the use of a boron nitrogen compound having a general structure as shown in formula (I) above in the manufacture of an electronic device.
Preferably, the electronic device comprises an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field quench device (O-FQD), a light emitting electrochemical cell (LEC), and an organic laser diode (O-laser).
According to one or more embodiments, the present invention also provides an organic electroluminescent device comprising the boron nitrogen compound of the general structure as shown in the above formula (I).
Preferably, the organic electroluminescent device comprises a cathode, an anode and an 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 boron-nitrogen compound with a general structure shown in the formula (I). Wherein the mass percentage of the boron nitrogen compound is 0.1% -50%.
According to one or more embodiments, the present invention also provides an organic optoelectronic device comprising a substrate layer; a first electrode; a second electrode facing the first electrode; and a luminescent material layer disposed between the first electrode and the second electrode, wherein the luminescent material layer comprises a boron nitrogen compound having a general structure as shown in formula (I) above. For example, a boron nitride compound may be included as a guest material in the light emitting material layer.
The invention also provides a composition which comprises the boron-nitrogen compound with the general structure shown in the formula (I).
The invention also provides a preparation which comprises the boron nitrogen compound with the general structure shown in the formula (I) or the composition and at least one solvent. The solvent is not particularly limited, and for example, an unsaturated hydrocarbon solvent such as toluene, xylene, mesitylene, tetrahydronaphthalene, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, a halogenated saturated hydrocarbon solvent such as carbon tetrachloride, chloroform, methylene chloride, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, a halogenated unsaturated hydrocarbon solvent such as chlorobenzene, dichlorobenzene, trichlorobenzene, an ether solvent such as tetrahydrofuran, tetrahydropyran, an ester solvent such as an alkyl benzoate, and the like, which are known to those skilled in the art, can be used.
The invention also provides a display or lighting device comprising one or more of the organic electroluminescent devices as described above.
Compared with the prior art, the invention has the beneficial effects that:
The boron-nitrogen compound has good thermal stability and good electron and hole transmission capability, and can improve the energy transmission performance and exciton utilization efficiency between a host and an object and the thermal stability; the boron-nitrogen compound is used as a functional layer, particularly used as a luminescent layer to manufacture an organic electroluminescent device, so that the current efficiency is improved, the service life of the device is also greatly prolonged, and the energy is effectively transferred to the boron-nitrogen compound for luminescent instead of heating after most of electrons and holes are compounded.
Detailed Description
The following describes the present invention in detail. The following description of the constituent elements may be based on the 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 may be understood more readily by reference to the following detailed description and the examples included therein. Before the present compounds, devices and/or methods are disclosed and described, it is to be understood that, unless otherwise indicated, they are not limited to specific synthetic methods or specific reagents as such may vary. It is also to be understood that the terminology used herein is for the purpose of describing particular aspects only and is not intended to be limiting. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing, the exemplary methods and materials are now described.
"Alkyl" as used herein refers to monovalent alkyl groups having 1 to 24 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms. Examples of this term are: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-hexyl and the like.
"Cycloalkyl" as used herein refers to a cyclic alkyl group having 3 to 24 carbon atoms and having a single or multiple ring fused, optionally substituted with 1 to 3 alkyl groups. Such cycloalkyl groups include, for example, monocyclic structures such as cyclopropyl, cyclobutyl, cyclopentyl, cyclooctyl, 1-methylcyclopropyl, and 2-methylcyclopentyl, 2-methylcyclooctyl, and the like, or polycyclic structures such as adamantyl and the like.
"Aryl" as used herein refers to an unsaturated aromatic carbocyclic ring having 6 to 30 carbon atoms and having a single ring (e.g., phenyl) or a multiple ring fused (e.g., naphthyl or anthracenyl). Preferred aryl groups include phenyl, naphthyl, and the like. Unless otherwise defined for the individual substituents, such aryl groups may be optionally substituted with 1 to 3 of the following substituents: hydroxy, acyl, acyloxy, alkyl, alkoxy, alkenyl, alkynyl, amino, aminoacyl, aryl, aryloxy, carboxyl ester, aminocarboxyl ester, cyano, halogen, nitro, heteroaryl, heterocycle, thioalkoxy, trihalomethyl, and the like. Preferred substituents include alkyl, alkoxy, halogen, cyano, nitro, trihalomethyl and thioalkoxy. But is not limited thereto.
The "heteroaryl" refers to a generic term for groups in which one or more aromatic nucleus carbons in the aryl group are replaced by heteroatoms including, but not limited to, oxygen, sulfur or nitrogen atoms, and the heteroaryl may be a monocyclic heteroaryl or a fused ring heteroaryl, examples of which may include, but are not limited to, pyridyl, pyrrolyl, pyridyl, thienyl, furyl, indolyl, quinolinyl, isoquinolinyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the like.
As used in this 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 indicated, all commercial reagents referred to in the following experiments were used directly after purchase.
In a preferred embodiment of the present invention, the OLED device of the present invention comprises a hole transporting layer, and the hole transporting material may preferably be selected from known or unknown materials, particularly preferably from the following structures, but does not represent 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 is comprised in the OLED device of the present invention. The preferred hole injection layer materials of the present invention are of the following structure, but do not represent the invention as limited to the following structure:
In a preferred embodiment of the present invention, the electron transport layer may be selected from at least one of the following compounds, but does not represent the present invention limited to the following structures:
The preparation method of the imidazole group-containing boron nitrogen compound, i.e., guest compound, and the light emitting performance of the device according to the present invention are explained in detail with reference to the following examples.
The OLED device of the present invention contains a host material, which may be selected from known or unknown materials, particularly preferably selected from the following structures, but does not represent the limitation of the present invention to the following structures:
example 1: synthesis of Compound 1
(1) Synthesis of Compounds 1-3
Compound 1-1 (248 mg,1 mmoL) and compound 1-2 (149 mg,1 mmoL) were dissolved in 50mL toluene solution. 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 under nitrogen atmosphere. 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 is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:4 to give the product 1-3 (170 mg, yield 54%). Mass spectrum m/z, theoretical value 315.18; actual measurement value M+H:316.22.
(2) Synthesis of Compounds 1-5
Compounds 1 to 3 (316 mg,1 mmoL) and compounds 1 to 4 (269 mg,1 mmoL) were dissolved in 50 toluene solution mL. 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 under nitrogen atmosphere. After the reaction system was refluxed for 48 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 is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:5 to give the product 1-5 (256 mg, yield 57%). Mass spectrum m/z, theoretical value 447.18; actual measurement value M+H:448.26.
(3) Synthesis of Compounds 1-7
Compounds 1 to 5 (448 mg,1 mmoL) and compounds 1 to 6 (225 mg,1 mmoL) were dissolved in 50 toluene solution mL. 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 under nitrogen atmosphere. 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 is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:4 to give the product 1-7 (234 mg, yield 37%). Mass spectrum m/z, theoretical value 636.35; actual measurement value M+H:637.37.
(4) Synthesis of Compounds 1-10
Compounds 1 to 8 (250 mg,1 mmoL) and compounds 1 to 9 (409 mg,1 mmoL) were dissolved in 50 toluene solution mL. 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 under nitrogen atmosphere. After the reaction system was refluxed for 48 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 is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:5 to give the product 1-10 (302 mg, yield 57%). Mass spectrum m/z, theoretical value 529.98; actual measurement value M+H:530.99.
(5) Synthesis of Compounds 1-11
Compounds 1 to 7 (637 mg,1 mmoL) and compounds 1 to 10 (531 mg,1 mmoL) were dissolved in 50 toluene mL. 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 under nitrogen atmosphere. 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 is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:7 to give the product 1-11 (327 mg, yield 30%). Mass spectrum m/z, theoretical value 1094.49; actual measurement value M+H:1095.51.
(6) Synthesis of Compound 1
Compounds 1 to 11 (1.096 g,1 mmoL) were dissolved in 60 mL anhydrous tert-butylbenzene. The reaction was cooled to-78℃and BuLi (1 mL,2 mmoL,2M in hexane) was slowly added. After 4 hours of reaction at-78 ℃, BBr 3 (247 mg,1 mmoL) was slowly added. After 1 hour of reaction at-50 ℃, the temperature was raised to room temperature, then N, N-diisopropylethylamine (387 mg,3 mmoL) was added, followed by heating to 120℃for reaction for 12 hours. After cooling to room temperature, 5mL aqueous sodium acetate (1M) was added. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:7 to give product 1 (263 mg, 26% yield). Mass spectrum m/z, theoretical value 1024.56; actual measurement value M+H:1025.58.
Example 2: synthesis of Compound 126
/>
(1) Synthesis of Compound 126-3:
Compound 126-1 (194 mg,1 mmoL) and compound 126-2 (330 mg,1 mmoL) were dissolved in 50 mL toluene solution. 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 under nitrogen atmosphere. After the reaction system was refluxed for 48 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 is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:2, to give a product 126-3 (157 mg, yield 40%). Mass spectrum m/z, theoretical value 396.01; actual measurement value M+H:397.03.
(2) Synthesis of Compound 126-5:
Compound 126-3 (396 mg,1 mmoL) and compound 126-4 (225 mg,1 mmoL) were dissolved in 50 mL toluene solution. 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 under nitrogen atmosphere. 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 is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:3 to give product 126-5 (226 mg, yield 46%). Mass spectrum m/z, theoretical value 493.25; actual measurement value M+H:494.28.
(3) Synthesis of Compound 126-7
BuLi (0.5 mL,1 mmoL,2M in hexane) was slowly added to a solution of compound 126-6 (396 mg,1 mmoL) in tetrahydrofuran (50 mL) at-78 ℃. After 3 hours of reaction, triphenylchlorosilane (294 mg,1 mmoL) was slowly added. After slowly warming to room temperature, the reaction was allowed to proceed overnight, then allowed to react at 80℃for 6 hours. After cooling to room temperature, ice water 1mL was added. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:9, yield 126-7 (246 mg, 47% yield). Mass spectrum m/z, theoretical value 525.92; actual measurement value M+H:526.94.
(4) Synthesis of Compound 126-8:
Compound 126-7 (529 mg,1 mmoL) and compound 126-5 (494 mg,1 mmoL) were dissolved in 50mL toluene solution. 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 under nitrogen atmosphere. 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 is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:4 to give product 126-8 (314 mg, 33% yield). Mass spectrum m/z, theoretical value 939.24; actual measurement value M+H:940.26.
(5) Synthesis of Compound 126-11:
Compound 126-9 (212 mg,1 mmoL) and compound 126-10 (200 mg,1 mmoL) were dissolved in 50 mL toluene solution. 10 mL aqueous sodium carbonate (2M) and tetrakis (triphenylphosphine) palladium (57 mg,0.05 mmoL) were added under nitrogen. 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 is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:3 to give the product 126-11 (176 mg, yield 61%). Mass spectrum m/z, theoretical value 287.13; actual measurement value M+H:288.15.
(6) Synthesis of Compound 126-13:
Compound 126-11 (287 mg,1 mmoL) and compound 126-12 (269 mg,1 mmoL) were dissolved in 50mL toluene solution. 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 under nitrogen atmosphere. 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 is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:6 to give product 126-13 (224 mg, yield 47%). Mass spectrum m/z, theoretical value 475.20; actual measurement value M+H:476.22.
(7) Synthesis of Compounds 126-14:
Compound 126-13 (476 mg,1 mmoL) and compound 126-8 (941 mg,1 mmoL) were dissolved in 50 mL toluene solution. 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 under nitrogen atmosphere. 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 is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:7, yield 126-14 (336 mg, yield 25%). Mass spectrum m/z, theoretical value 1334.51; actual measurement value M+H:1335.53.
(8) Synthesis of Compound 126
Tert-butyllithium (1.25 mL, 1.6M pentane solution, 2 mmoL) was slowly added dropwise to a solution of compound 126-14 (1336 mg,1 mmoL) in tert-butylbenzene (100 mL) under nitrogen at zero degrees. After 4 hours of reaction at 60℃the system was cooled to-50℃and BBr 3 (494 mg,2 mmoL) was added. After 1 hour of reaction at room temperature, N-diisopropylethylamine (259 mg,2 mmoL) was added. Then the temperature is raised to 120 ℃ for reaction for 12 hours. After cooling to room temperature, 5 mL aqueous sodium acetate (1M) was added. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:8 to give product 126 (259 mg, yield 20%). Mass spectrum m/z, theoretical value 1308.54; actual measurement value M+H:1309.56.
Example 3: synthesis of Compound 5
Compound 5 was synthesized referring to the synthetic route of compound 1 or compound 126. The yield of the final product was 23%. Mass spectrum m/z, theoretical value 1156.66; actual measurement value M+H:1157.68.
Example 4: synthesis of Compound 9
Compound 9 was synthesized referring to the synthetic route of compound 1 or compound 126. The yield of the final product was 26%. Mass spectrum m/z, theoretical value 1202.64; actual measurement value M+H:1203.66.
Example 5: synthesis of Compound 10
Referring to the synthetic route for compound 1 or compound 126, compound 10 was synthesized. The yield of the final product was 28%. Mass spectrum m/z, theoretical value 1114.58; actual measurement value M+H:1115.61.
Example 6: synthesis of Compound 12
Compound 12 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 25%. Mass spectrum m/z, theoretical value 1130.55; actual measurement value M+H:1131.58.
Example 7: synthesis of Compound 13
Compound 13 was synthesized referring to the synthetic route of compound 1 or compound 126. The yield of the final product was 27%. Mass spectrum m/z, theoretical value 1084.57; actual measurement value M+H:1085.59.
Example 8: synthesis of Compound 19
Compound 19 was synthesized referring to the synthetic route of compound 1 or compound 126. The yield of the final product was 36%. Mass spectrum m/z, theoretical value 1184.60; actual measurement value M+H:1185.63.
Example 9: synthesis of Compound 26
Compound 26 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 32%. Mass spectrum m/z, theoretical value 1169.65; actual measurement value M+H:1170.67.
Example 10: synthesis of Compound 31
Compound 31 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 29%. Mass spectrum m/z, theoretical value 1058.51; actual measurement value M+H:1059.53.
Example 11: synthesis of Compound 38
Compound 38 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 30%. Mass spectrum m/z, theoretical value 1231.73; actual measurement value M+H:1232.75.
Example 12: synthesis of Compound 43
Compound 43 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 29%. Mass spectrum m/z, theoretical value 1122.58; actual measurement value M+H:1123.61.
Example 13: synthesis of Compound 47
Compound 47 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 25%. Mass spectrum m/z, theoretical value 1200.63; actual measurement value M+H:1201.66.
Example 14: synthesis of Compound 50
Compound 50 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 32%. Mass spectrum m/z, theoretical value 1260.67; actual measurement value M+H:1261.69.
Example 15: synthesis of Compound 52
Compound 52 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 30%. Mass spectrum m/z, theoretical value 1206.58; actual measurement value M+H:1207.61.
Example 16: synthesis of Compound 55
Compound 55 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 23%. Mass spectrum m/z, theoretical value 1226.59; actual measurement value M+H:1227.62.
Example 17: synthesis of Compound 58
Compound 58 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 23%. Mass spectrum m/z, theoretical value 1302.62; actual measurement value M+H:1303.64.
Example 18: synthesis of Compound 64
Compound 64 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 26%. Mass spectrum m/z, theoretical value 1246.56; actual measurement value M+H:1247.58.
Example 19: synthesis of Compound 66
Compound 66 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 29%. Mass spectrum m/z, theoretical value 1282.65; actual measurement value M+H:1283.67.
Example 20: synthesis of Compound 68
Compound 68 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 32%. Mass spectrum m/z, theoretical value 1094.61; actual measurement value M+H:1095.64.
Example 21: synthesis of Compound 70
Compound 70 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 24%. Mass spectrum m/z, theoretical value 1044.53; actual measurement value M+H:1045.56.
Example 22: synthesis of Compound 74
Compound 74 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 28%. Mass spectrum m/z, theoretical value 1316.73; actual measurement value M+H:1317.75.
Example 23: synthesis of Compound 78
Compound 78 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 25%. Mass spectrum m/z, theoretical value 1226.59; actual measurement value M+H:1227.62.
Example 24: synthesis of Compound 79
Compound 79 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 31%. Mass spectrum m/z, theoretical value 1134.54; actual measurement value M+H:1135.56.
Example 25: synthesis of Compound 85
Compound 85 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 31%. Mass spectrum m/z, theoretical value 1251.58; actual measurement value M+H:1252.61.
Example 26: synthesis of Compound 91
Compound 91 was synthesized referring to the synthetic route of compound 1 or compound 126. The yield of the final product was 26%. Mass spectrum m/z, theoretical value 1312.60; actual measurement value M+H:1313.62.
Example 27: synthesis of Compound 99
Compound 99 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 23%. Mass spectrum m/z, theoretical value 1250.71; actual measurement value M+H:1251.73.
Example 28: synthesis of Compound 102
Compound 102 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 28%. Mass spectrum m/z, theoretical value 1302.60; actual measurement value M+H:1303.63.
Example 29: synthesis of Compound 106
Compound 106 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 23%. Mass spectrum m/z, theoretical value 1160.60; actual measurement value M+H:1161.63.
Example 30: synthesis of Compound 110
Compound 110 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 28%. Mass spectrum m/z, theoretical value 1180.54; actual measurement value M+H:1181.56.
Example 31: synthesis of Compound 114
Compound 114 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 21%. Mass spectrum m/z, theoretical value 1095.49; actual measurement value M+H:1096.52.
Example 32: synthesis of Compound 123
Compound 123 was synthesized referring to the synthetic route of compound 1 or compound 126. The yield of the final product was 29%. Mass spectrum m/z, theoretical value 1238.59; actual measurement value M+H:1239.61.
Example 33: synthesis of Compound 137
Compound 137 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 20%. Mass spectrum m/z, theoretical value 1248.48; actual measurement value M+H:1249.51.
Example 34: synthesis of Compound 140
Compound 140 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 26%. Mass spectrum m/z, theoretical 1210.56; actual measurement value M+H:1211.58.
Example 35: synthesis of Compound 143
Compound 143 was synthesized referring to the synthetic route of compound 1 or compound 126. The yield of the final product was 25%. Mass spectrum m/z, theoretical value 1316.60; actual measurement value M+H:1317.62.
Example 36: synthesis of Compound 147
Compound 147 was synthesized with reference to the synthetic route for compound 1 or compound 126. The yield of the final product was 29%. Mass spectrum m/z, theoretical value 1322.59; actual measurement value M+H:1323.62.
Example 37: synthesis of Compound 152
Compound 152 was synthesized with reference to the synthetic route of compound 1 or compound 126. The yield of the final product was 22%. Mass spectrum m/z, theoretical value 1230.53; actual measurement value M+H:1231.55.
Manufacturing of OLED device:
As a reference preparation mode of an embodiment of a device, the invention comprises evaporating p-doped material on the surface or anode of ITO glass with the size of 2mm multiplied by 2mm or co-evaporating the p-doped material with a hole transport material at a concentration of 1% -50% to form a Hole Injection Layer (HIL) of 5-100nm, forming a Hole Transport Layer (HTL) of 5-200nm on the hole injection layer, then co-evaporating a host material on the hole transport layer with an imidazole-containing compound (guest material) prepared by the invention at a weight ratio of 97:3 to form a luminescent layer (EML) of 10-100nm, finally co-evaporating to form an Electron Transport Layer (ETL) of 35nm, and evaporating cathode Al of 70 nm, thereby manufacturing the organic electroluminescent diode.
In a preferred embodiment, the structure of the bottom-emitting OLED device provided by the present invention is: the glass containing ITO is used as an anode, HIL is HT-1:P-3 (weight ratio is 95:5) and the thickness is 10 nanometers; HTL is HT-1 and has a thickness of 90 nanometers; the EBL is HT-8, the thickness is 10 nanometers, the EML is a main material (H-1), the imidazole-containing compound 1 provided by the invention (weight ratio is 97:3), the thickness is 35 nanometers, and the ETL is ET-3: liQ (weight ratio 50:50), thickness 35 nm, then evaporation cathode Al 70 nm, and organic electroluminescent diode was prepared, which was designated as application example 1.
Referring to the method provided in application example 1, the prepared boron-nitrogen compound 126, compound 5, compound 9, compound 10, compound 12, compound 13, compound 19, compound 26, compound 31, compound 38, compound 43, compound 47, compound 50, compound 52, compound 55, compound 58, compound 64, compound 66, compound 68, compound 70, compound 74, compound 78, compound 79, compound 85, compound 91, compound 99, compound 102, compound 106, compound 110, compound 114, compound 123, compound 137, compound 140, compound 143, compound 147, compound 152 were used as the implementation object instead of compound 1, and the organic electroluminescent diode was prepared by co-evaporating the above compound and the host compound in a weight ratio of 3:97 to form a light-emitting layer, and application examples 2 to 37 were described.
Production of comparative example 1
Comparative example 1 was prepared with reference to the method provided in application example 1 described above, except that BN-1 was used as the guest material of the light-emitting layer in comparative example 1, respectively, instead of the imidazole-containing boron nitride compound of the present invention. The chemical structure of compound BN-1 of comparative example 1 is as follows:
The characteristics of the device examples and comparative examples prepared above, such as current efficiency, voltage and lifetime, were tested by standard methods, and the device luminescence characteristic data are shown in table 1.
TABLE 1 light emission characteristics data sheet for devices
/>
As can be seen from table 1, application examples 1 to 37 do not have a significant difference in FWHM compared to comparative example 1, but exhibit more prominent advantages in both current efficiency and lifetime, representing good device performance thereof. The improvement of the performance of each device in application examples is based on the boron-nitrogen compound with a specific substitution structure, particularly the addition of imidazole groups, so that the compound material has better carrier transmission capacity, and the compound is used as a guest material of a light-emitting layer to prepare an electronic device, so that the device has higher current efficiency and service life. The imidazole-containing compound provided by the invention has certain commercial application value.
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should make equivalent substitutions or modifications according to the technical scheme of the present invention and the inventive concept thereof, and should be covered by the scope of the present invention.

Claims (13)

1. A boron nitrogen compound containing imidazole and derivative groups is characterized in that the boron nitrogen compound has a structure shown in a formula (I),
；
In formula (I), ar 1 is absent or present, when present, said Ar 1 is fused to an attached imidazole group, ar 1 is selected from substituted or unsubstituted C6-C36 aryl;
Each R 1-R5 is independently selected from hydrogen, deuterium, C1-C24 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, the heteroatoms in the heteroaryl being selected from O, S; when substituted, the substituent is selected from any one or more of deuterium, C1-C24 alkyl, C3-C24 cycloalkyl and substituted or unsubstituted C6-C30 aryl.
2. The boron nitride according to claim 1, wherein Ar 1 is selected from one of absent or phenyl, methyl substituted indenyl, phenanthryl, and R 2 is selected from hydrogen, deuterium, methyl, ethyl, propyl, t-butyl, phenyl, t-butylphenyl.
3. The boron nitride compound according to claim 1, wherein each R 1、R4 is independently selected from hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, pyridinyl, adamantyl, phenyl, tert-butylphenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, triphenylsilyl, substituted or unsubstituted indenyl, substituted or unsubstituted benzimidazolyl; when substituted, the substitution is selected from any one or more of deuterium, C1-C10 alkyl, C3-C14 cycloalkyl, C6-C36 aryl.
4. The boronitrogen compound according to claim 1, wherein R 3 is selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, t-butyl, phenyl, t-butylphenyl, di-t-butylphenyl, biphenyl, t-butyl substituted biphenyl, adamantyl, dibenzofuranyl, dimethylfluorenyl.
5. The boronitride of claim 1, wherein R 5 is selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, t-butyl, diphenylamino, methoxyphenyl, triphenylsilyl, dibenzofuranyl, dimethylfluorenyl, phenyl-substituted benzimidazolyl.
6. The boron nitride according to claim 1, wherein the boron nitride is selected from any one of the following chemical structures, wherein "D" represents deuterium:
/>
/>
/>
/>
。
7. Use of a boron nitride compound according to any one of claims 1 to 6 in the manufacture of an electronic device.
8. The use according to claim 7, wherein the boron-nitrogen compound is used as a light-emitting layer material for an organic electroluminescent device.
9. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises a cathode, an anode and at least one organic functional layer interposed therebetween; the boron-nitrogen compound according to any one of claims 1 to 6 is contained in the organic functional layer.
10. An organic optoelectronic device, comprising: a substrate layer; a first electrode; a second electrode facing the first electrode; and a luminescent material layer disposed between the first electrode and the second electrode; wherein the luminescent material layer comprises the boron nitrogen compound according to any one of claims 1 to 6.
11. A composition comprising a boron nitrogen compound according to any one of claims 1 to 6.
12. A formulation comprising a boron nitrogen compound according to any one of claims 1 to 6 and at least one solvent.
13. A display or lighting device, characterized in that it comprises one or more of the organic electroluminescent devices of claim 9.
CN202410353804.3A 2024-03-27 2024-03-27 Boron-nitrogen compound containing imidazole and derivative group, organic electroluminescent device and application Pending CN117946146A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202410353804.3A CN117946146A (en) 2024-03-27 2024-03-27 Boron-nitrogen compound containing imidazole and derivative group, organic electroluminescent device and application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202410353804.3A CN117946146A (en) 2024-03-27 2024-03-27 Boron-nitrogen compound containing imidazole and derivative group, organic electroluminescent device and application

Publications (1)

Publication Number Publication Date
CN117946146A true CN117946146A (en) 2024-04-30

Family

ID=90801812

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202410353804.3A Pending CN117946146A (en) 2024-03-27 2024-03-27 Boron-nitrogen compound containing imidazole and derivative group, organic electroluminescent device and application

Country Status (1)

Country Link
CN (1) CN117946146A (en)

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112442055A (en) * 2019-08-30 2021-03-05 环球展览公司 Organic electroluminescent material and device
CN113135935A (en) * 2021-04-14 2021-07-20 吉林奥来德光电材料股份有限公司 Polycyclic aromatic compound and preparation method and application thereof
WO2021172965A1 (en) * 2020-02-28 2021-09-02 에스에프씨 주식회사 Polycyclic aromatic derivative compound and organoelectroluminescent device using same
CN113348171A (en) * 2019-11-29 2021-09-03 株式会社Lg化学 Compound and organic light-emitting element comprising same
CN115073502A (en) * 2021-03-12 2022-09-20 Sfc株式会社 Polycyclic compound and organic electroluminescent device using the same
CN115093437A (en) * 2022-06-17 2022-09-23 华中科技大学 Boron-nitrogen heterocyclic derivative based on fusion donor, preparation and application thereof
WO2023024445A1 (en) * 2021-08-23 2023-03-02 浙江华显光电科技有限公司 Spiro compound, preparation, organic electroluminescent diode, and display device
CN116003454A (en) * 2022-12-26 2023-04-25 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound and preparation method and application thereof
CN116217608A (en) * 2023-05-08 2023-06-06 浙江华显光电科技有限公司 Silicon-containing compounds and their use in organic light-emitting devices
CN117186139A (en) * 2023-07-26 2023-12-08 安徽省华显新材料科技有限公司 Boron nitrogen compound and organic electronic device using same

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112442055A (en) * 2019-08-30 2021-03-05 环球展览公司 Organic electroluminescent material and device
CN113348171A (en) * 2019-11-29 2021-09-03 株式会社Lg化学 Compound and organic light-emitting element comprising same
WO2021172965A1 (en) * 2020-02-28 2021-09-02 에스에프씨 주식회사 Polycyclic aromatic derivative compound and organoelectroluminescent device using same
CN115073502A (en) * 2021-03-12 2022-09-20 Sfc株式会社 Polycyclic compound and organic electroluminescent device using the same
CN113135935A (en) * 2021-04-14 2021-07-20 吉林奥来德光电材料股份有限公司 Polycyclic aromatic compound and preparation method and application thereof
WO2023024445A1 (en) * 2021-08-23 2023-03-02 浙江华显光电科技有限公司 Spiro compound, preparation, organic electroluminescent diode, and display device
CN115093437A (en) * 2022-06-17 2022-09-23 华中科技大学 Boron-nitrogen heterocyclic derivative based on fusion donor, preparation and application thereof
CN116003454A (en) * 2022-12-26 2023-04-25 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound and preparation method and application thereof
CN116217608A (en) * 2023-05-08 2023-06-06 浙江华显光电科技有限公司 Silicon-containing compounds and their use in organic light-emitting devices
CN117186139A (en) * 2023-07-26 2023-12-08 安徽省华显新材料科技有限公司 Boron nitrogen compound and organic electronic device using same

Similar Documents

Publication Publication Date Title
CN116217608B (en) Silicon-containing compounds and their use in organic light-emitting devices
CN116514859B (en) Narrow-emission luminescent compound and application thereof in electronic device
CN108929234B (en) Aromatic amine derivative and organic electroluminescent device thereof
CN108101897B (en) Novel organic electroluminescent compound and organic electroluminescent device containing same
KR101165698B1 (en) Organic electronic element comprising a new compound, and a new compound and a composition for organic electronic element
Zhou et al. Benzoylpyridine-based TADF emitters with AIE feature for efficient non-doped OLEDs by both evaporation and solution process
CN116496308A (en) Condensed cyclic compound and organic light-emitting device comprising the same
CN114773286B (en) Nitrogen-containing heterocyclic organic compound and organic light-emitting device thereof
CN117209461B (en) Organic photoelectric compound, composition with same and organic light-emitting device
CN117209460B (en) Organic compound, OLED (organic light-emitting diode) with organic compound and organic light-emitting device
CN112920209A (en) Organic metal complex and organic photoelectric element containing same
CN109796449A (en) It is a kind of using pyridine as the compound of core and its application on organic electroluminescence device
Braveenth et al. Fluorene core with several modification by using donor type triphenylamine and carbazole derivatives for organic light emitting diodes
WO2014180037A1 (en) Sulphone-contained compound, organic electroluminescence device using same, and fabrication method thereof
US20220144862A1 (en) Organic compound and application thereof
Chen et al. Diphenylamino-substituted bicarbazole derivative: Hole-transporting material with high glass-transition temperature, good electron and triplet exciton blocking capabilities and efficient hole injection
CN117946146A (en) Boron-nitrogen compound containing imidazole and derivative group, organic electroluminescent device and application
CN117088920B (en) Pt complex and application thereof in organic light-emitting device
CN116874517B (en) Selenophene-containing compound and application thereof in organic light-emitting device
CN116903651B (en) Selenium-containing luminescent compound and application thereof in electronic device
CN117229328B (en) Pt complex with spirofluorene structure and application thereof in organic light-emitting device
CN114907322B (en) Electronic transmission material containing heterocyclic structure and preparation method and application thereof
KR102599321B1 (en) Novel organic electroluminescent materials and devices
EP4335846A1 (en) Organic electroluminescent material and device thereof
CN115353483B (en) Compound containing biscarbazole structure and organic electroluminescent device

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination