CN115572303A - Organic light-emitting compound and application thereof - Google Patents

Organic light-emitting compound and application thereof Download PDF

Info

Publication number
CN115572303A
CN115572303A CN202211154996.2A CN202211154996A CN115572303A CN 115572303 A CN115572303 A CN 115572303A CN 202211154996 A CN202211154996 A CN 202211154996A CN 115572303 A CN115572303 A CN 115572303A
Authority
CN
China
Prior art keywords
layer
organic
organic light
substituted
unsubstituted
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
CN202211154996.2A
Other languages
Chinese (zh)
Inventor
甘国月
孙加宝
黄雪明
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.)
EverDisplay Optronics Shanghai Co Ltd
Original Assignee
EverDisplay Optronics Shanghai 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 EverDisplay Optronics Shanghai Co Ltd filed Critical EverDisplay Optronics Shanghai Co Ltd
Priority to CN202211154996.2A priority Critical patent/CN115572303A/en
Publication of CN115572303A publication Critical patent/CN115572303A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention relates to an organic electroluminescent compound, the structure of which is shown as formula (I) or formula (II); wherein X is selected from O or S; a. The 1 ‑A 2 Each independently selected from substituted or unsubstituted C 6 ‑C 60 Aryl or substituted or unsubstituted C 3 ‑C 60 The heteroaryl group of (a); ar (Ar) 1 And Ar 2 Each independently selected from substituted or unsubstituted C 6 ‑C 60 Aryl or substituted or unsubstituted C 3 ‑C 60 The heteroaryl group of (a). The organic electroluminescent compound is benzo heterocyclic pyrazine derivatives, such as benzofuran/thiophene pyrazine structures, which have good electron withdrawing capability and form structures with electron donating groups and electron withdrawing groups by combining with triarylamine structures with electron donating capability. In addition, the organic electroluminescent compounds of the present invention contain a stable polycyclic structure to stabilize the materialGreatly improves the glass transition temperature of the material due to larger molecular weight, thereby ensuring that the material is not decomposed after long-time evaporation.

Description

Organic light-emitting compound and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic luminescent compound and application thereof.
Background
Researchers have synthesized a large number of organic light emitting materials and have been widely used in Organic Light Emitting Diodes (OLEDs), organic lasers, chemical sensors, biological detectors; however, in practical applications, since the OLED has unique characteristics in the new generation of full-color flat panel display, solid-state lighting, and light source saving, it is considered as the most competitive research focus of the new generation. The OLED based on the fluorescent material has the characteristic of high stability, but is limited by the quantum statistics law, and under the action of electric activation, the proportion of generated singlet excitons and triplet excitons is 1:3, so that the maximum internal quantum efficiency of the electroluminescent fluorescent material is only 25%. The phosphorescence material has the spin-orbit coupling effect of heavy atoms, and can comprehensively utilize singlet excitons and triplet excitons, the theoretical internal quantum efficiency can reach 100%, but the phosphorescence-based OLED has an obvious efficiency roll-off effect and has a certain obstruction in high-brightness application. The phosphorescent material can comprehensively utilize singlet excitons and triplet excitons, achieving 100% internal quantum efficiency. However, the triplet-triplet state (T1-T1) is quenched in the practical operation of the device due to the relatively long excited-state exciton lifetime of the transition metal complex. To overcome this problem, researchers often dope phosphorescent materials into organic host materials. Therefore, it is important to develop a host material and a guest material having high performance for a high-efficiency organic light emitting diode.
At present, the main material widely used in phosphorescent devices is CBP (4,4' -bis (9-carbazolyl) biphenyl), but the driving voltage required by the main material is higher, the glass transition temperature (Tg) is low (62 ℃), and the main material is easy to crystallize.
The invention provides an organic light-emitting compound and application thereof, aiming at the problems of higher driving voltage and the like required by the existing host material.
Disclosure of Invention
The invention aims to provide an organic light-emitting compound and application thereof, aiming at overcoming the defects in the prior art.
In order to achieve the purpose, the invention adopts the technical scheme that:
the first aspect of the present invention provides an organic light emitting compound, wherein the structure of the organic light emitting compound is represented by formula (I) or formula (II):
Figure BDA0003857484570000021
wherein R is 1 -R 4 Each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted C 6 -C 27 Aryl or substituted or unsubstituted C 12 -C 20 The heteroaryl group of (a).
Preferably, the organic light-emitting compound is selected from:
Figure BDA0003857484570000022
Figure BDA0003857484570000031
a second aspect of the present invention provides an organic light emitting material comprising: an organic light-emitting compound as described above.
A third aspect of the present invention is to provide a light emitting layer comprising: an organic light emitting material as described above.
A fourth aspect of the present invention provides an organic electroluminescent device comprising: a light emitting layer as described above.
Preferably, the method further comprises the following steps: the organic light emitting diode comprises an anode layer, a cathode layer and an organic functional layer arranged between the anode layer and the cathode layer, wherein the organic functional layer comprises the light emitting layer.
More preferably, the organic functional layer further comprises: at least one of an electron transport layer, an electron blocking layer, an electron injection layer, a hole blocking layer, or a hole transport layer.
By adopting the technical scheme, compared with the prior art, the invention has the following technical effects:
the invention provides an organic luminescent compound containing an S/N heterocyclic compound and a triarylamine structure, which can be used as a green main body material in an electroluminescent device; the organic luminescent compound can form a stable heterocyclic organic aromatic system, has proper HOMO and LUMO energy levels, can adjust the band gap and polarity of the system, has rich photoelectric properties, and can ensure that a device has the characteristics of higher luminous efficiency, lower voltage and the like.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
It should be noted that the embodiments and features of the embodiments may be combined with each other without conflict.
The present invention is further illustrated by the following examples, which are not to be construed as limiting the invention.
Example 1
Figure BDA0003857484570000041
Under nitrogen protection, a 200mL two-necked bottle containing a mixture of raw material A (5.0 mmol), raw material B (5.0 mmol), potassium carbonate (10.0 mmol) and tetrakistriphenylphosphine palladium (0.25 mmol) was charged with dry toluene (70 mL) and water (35 mL); refluxing the mixture at 100-120 deg.C for 12-24 hr; after cooling to room temperature, the mixture was extracted with DCM/water; the combined organic layers were dried over magnesium sulfate, filtered and rotary evaporated; the residue was purified by silica gel column chromatography followed by recrystallization from toluene to give a solid compound, which was purified by silica gel column chromatography to give intermediate 1 in 70% yield.
Figure BDA0003857484570000042
Dissolving the intermediate 1 in 40mL of triethyl phosphite, stirring for 3h at 160 ℃ under the protection of nitrogen, cooling to room temperature after the reaction is finished, flushing a silica gel funnel with petroleum ether to remove the triethyl phosphite, and continuously passing the silica gel funnel to obtain an intermediate 2 with the yield of 70%.
Figure BDA0003857484570000043
Intermediate 2 (5.0 mmol) and raw material R 3 dissolving-Br (5.0 mmol), sodium tert-butoxide, tris (dibenzylidene) acetone dipalladium and tri-tert-butylphosphine in 60mL of toluene, and stirring at 90 ℃ for 3 hours under the protection of nitrogen; after the reaction is finished, cooling to room temperature, extracting twice with dichloromethane and water, evaporating the organic phase to dryness with anhydrous magnesium sulfate, and carrying out column chromatography to obtain an intermediate 3, wherein the yield is 75%.
Figure BDA0003857484570000051
Dissolving a raw material C (5.0 mmol), a raw material D (5.0 mmol), sodium tert-butoxide, tris (dibenzylidene) acetone dipalladium and tri-tert-butylphosphine in 60mL of toluene, and stirring at 90 ℃ for 3 hours under the protection of nitrogen; after the reaction is finished, cooling to room temperature, extracting twice by using dichloromethane and water, evaporating the organic phase anhydrous magnesium sulfate to dryness, and carrying out column chromatography to obtain an intermediate 4, wherein the yield is 75%.
Figure BDA0003857484570000052
Dissolving intermediate 4 (5.0 mmol), intermediate 3 (5.0 mmol), sodium tert-butoxide, tris (dibenzylidene) acetondipalladium and tri-tert-butylphosphine in 60mL of toluene, and stirring at 90 ℃ for 3 hours under the protection of nitrogen; after the reaction is finished, cooling to room temperature, extracting twice with dichloromethane and water, evaporating the organic phase to dryness with anhydrous magnesium sulfate, and performing column chromatography to obtain a target structure, wherein the yield is 75%.
Example 2
Figure BDA0003857484570000053
Under nitrogen protection, a 200mL two-necked bottle containing a mixture of raw material A1 (5.0 mmol), raw material A2 (5.0 mmol), potassium carbonate (10.0 mmol) and tetrakistriphenylphosphine palladium (0.25 mmol) was charged with dry toluene (70 mL) and water (35 mL); refluxing the mixture at 100-120 deg.C for 12-24 hr; after cooling to room temperature, the mixture was extracted with DCM/water; the combined organic layers were dried over magnesium sulfate, filtered and rotary evaporated; the residue was purified by silica gel column chromatography followed by recrystallization from toluene to give a solid compound, which was purified by silica gel column chromatography to give intermediate B1 in 70% yield.
Dissolving the intermediate B1 in 40mL of triethyl phosphite, stirring for 3h at 160 ℃ under the protection of nitrogen, cooling to room temperature after the reaction is finished, flushing a silica gel funnel with petroleum ether to remove the triethyl phosphite, and then continuously passing through the silica gel funnel to obtain an intermediate B2 with the yield of 70%.
Dissolving the intermediate B2 (5.0 mmol), bromobenzene (5.0 mmol), sodium tert-butoxide, tris (dibenzylidene) acetone dipalladium and tri-tert-butylphosphine in 60mL of toluene, and stirring at 90 ℃ for 3 hours under the protection of nitrogen; after the reaction is finished, the reaction product is cooled to room temperature, dichloromethane and water are used for extraction twice, organic phase anhydrous magnesium sulfate is evaporated to dryness, and column chromatography is carried out to obtain an intermediate B3 (the yield is 75%, and the molecular weight is 453).
Dissolving raw material A4 (5.0 mmol), raw material A5 (5.0 mmol), sodium tert-butoxide, tris (dibenzylidene) acetone dipalladium and tri-tert-butylphosphine in 60mL of toluene, and stirring at 90 ℃ for 3 hours under the protection of nitrogen; after the reaction is finished, the reaction product is cooled to room temperature, dichloromethane and water are used for extraction twice, organic phase anhydrous magnesium sulfate is evaporated to dryness, and column chromatography is carried out to obtain an intermediate B4 (the yield is 75%, and the molecular weight is 321).
Dissolving intermediate B4 (5.0 mmol), intermediate 3 (5.0 mmol), sodium tert-butoxide, tris (dibenzylidene) acetondipalladium and tri-tert-butylphosphine in 60mL of toluene, and stirring at 90 ℃ for 3 hours under the protection of nitrogen; after the reaction, the reaction mixture was cooled to room temperature, extracted twice with dichloromethane and water, and the organic phase was evaporated to dryness over anhydrous magnesium sulfate and subjected to column chromatography to obtain compound 1 (yield 75%, molecular weight 694).
In a similar manner, compounds 2-10 were prepared, involving the main reactants/intermediates as shown in the following table:
TABLE 1
Figure BDA0003857484570000061
Figure BDA0003857484570000071
Figure BDA0003857484570000081
The compounds have higher HOMO energy level and can be used as a light-emitting layer material; the compound also has high thermal stability, and ensures the thermal stability of the material in the evaporation process.
Application examples
Cleaning an ITO anode layer on a transparent substrate layer, respectively ultrasonically cleaning the ITO anode layer for 15 minutes by using deionized water, acetone and ethanol, then treating the ITO anode layer in a plasma cleaner for 2 minutes, and evaporating the ITO anode layer in a vacuum evaporation mode to form the following layer structure: HAT-CN material with the thickness of 10nm is used as a hole injection layer; NPB material with the thickness of 70nm is used as a hole transport layer; NPB material with the thickness of 20nm is used as an electron blocking layer; organic light emitting Compound (host) of the present invention and Ir (ppy) at a thickness of 30nm 3 (doping material) as a light-emitting layer; TPBI material with the thickness of 40nm is used as a hole blocking/electron transporting layer; liF material with the thickness of 1nm is used as an electron injection layer; al with a thickness of 100nm was used as a cathode.
The structure of the relevant molecular formula is shown below:
Figure BDA0003857484570000082
TABLE 2
Figure BDA0003857484570000091
The OLEDs are characterized in a standard manner, with the electroluminescence spectrum, power efficiency (measured in cd/A) and voltage (at 1000 cd/m) determined from the current-voltage-luminance characteristics (JUL characteristics) 2 Lower measure, in V). For selected tests, the lifetime was determined. The lifetime is defined as the time after which the brightness has decreased from a certain starting brightness to a certain proportion. The numeral T95 indicates that the specified lifetime is that the luminance has dropped to 95% of the starting luminance, i.e. for example from 1000cd/m 2 Down to 950cd/m 2 The time of day. Different initial brightness is selected according to the light emission color. The lifetime value can be converted into other values of the starting brightness by means of conversion formulas known to the person skilled in the art. In this context, the starting luminance is 1000cd/m 2 The life of (b) is a standard value. As can be seen from Table 2, when the compound provided by the invention is used as a green light-emitting host material of an organic electroluminescent device, the device has higher device efficiency, lower working voltage and longer service life.
The invention provides an organic luminescent compound containing an S/N heterocyclic compound and a triarylamine structure, which can be used as a green main body material in an electroluminescent device; the organic luminescent compound can form a stable heterocyclic organic aromatic system, has proper HOMO and LUMO energy levels, can adjust the band gap and polarity of the system, has rich photoelectric properties, and can ensure that a device has the characteristics of higher luminous efficiency, lower voltage and the like.
While the invention has been described with reference to a preferred embodiment, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope of the invention.

Claims (7)

1. An organic light-emitting compound, wherein the structure of the organic light-emitting compound is represented by formula (I) or formula (II):
Figure FDA0003857484560000011
wherein R is 1 -R 4 Each independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted C 6 -C 27 Aryl or substituted or unsubstituted C 12 -C 20 The heteroaryl group of (a).
2. The organic light-emitting compound of claim 1, wherein the organic light-emitting compound is selected from the group consisting of:
Figure FDA0003857484560000012
Figure FDA0003857484560000021
3. an organic light-emitting material, comprising: an organic light-emitting compound as claimed in any one of claims 1 to 2.
4. A light-emitting layer, comprising: the organic light-emitting material according to claim 3.
5. An organic electroluminescent device, comprising: the light-emitting layer according to claim 4.
6. The organic electroluminescent device according to claim 5, further comprising: the organic light emitting diode comprises an anode layer, a cathode layer and an organic functional layer arranged between the anode layer and the cathode layer, wherein the organic functional layer comprises the light emitting layer.
7. The organic electroluminescent device according to claim 6, wherein the organic functional layer further comprises: at least one of an electron transport layer, an electron blocking layer, an electron injection layer, a hole blocking layer, or a hole transport layer.
CN202211154996.2A 2022-09-21 2022-09-21 Organic light-emitting compound and application thereof Pending CN115572303A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202211154996.2A CN115572303A (en) 2022-09-21 2022-09-21 Organic light-emitting compound and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202211154996.2A CN115572303A (en) 2022-09-21 2022-09-21 Organic light-emitting compound and application thereof

Publications (1)

Publication Number Publication Date
CN115572303A true CN115572303A (en) 2023-01-06

Family

ID=84581964

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202211154996.2A Pending CN115572303A (en) 2022-09-21 2022-09-21 Organic light-emitting compound and application thereof

Country Status (1)

Country Link
CN (1) CN115572303A (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210355142A1 (en) * 2021-04-23 2021-11-18 Shanghai Tianma AM-OLED Co., Ltd. Compound, material for an organic electroluminescent device and application thereof
CN114436942A (en) * 2022-02-18 2022-05-06 长春海谱润斯科技股份有限公司 Arylamine compound containing carbazole group and organic electroluminescent device thereof
CN114539270A (en) * 2021-12-09 2022-05-27 上海钥熠电子科技有限公司 Compound containing carbazole derivative and application thereof in organic electroluminescent device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210355142A1 (en) * 2021-04-23 2021-11-18 Shanghai Tianma AM-OLED Co., Ltd. Compound, material for an organic electroluminescent device and application thereof
CN114539270A (en) * 2021-12-09 2022-05-27 上海钥熠电子科技有限公司 Compound containing carbazole derivative and application thereof in organic electroluminescent device
CN114436942A (en) * 2022-02-18 2022-05-06 长春海谱润斯科技股份有限公司 Arylamine compound containing carbazole group and organic electroluminescent device thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ISABEL C. F. R. FERREIRA: "Tandem palladium-catalyzed borylation and Suzuki coupling (BSC) to thienocarbazole precursors", 《TETRAHEDRON LETTERS》, vol. 44, pages 4327 - 4329, XP004423972, DOI: 10.1016/S0040-4039(03)00952-3 *

Similar Documents

Publication Publication Date Title
KR101788793B1 (en) Pyridine derivative compound and organic electroluminescent devices comprising the same
JP2019501986A (en) Thermally activated delayed fluorescent material and its application in organic electroluminescent devices
KR101529878B1 (en) Organic Light Emitting Material and Organic Light Emitting Diode Having The Same
CN108276336B (en) Organic photoelectric functional material, light-emitting device, and preparation method and application thereof
CN112500410B (en) Spiro nitrogen-containing organic luminescent compound, and preparation method and application thereof
CN109755416B (en) Organic electroluminescent device containing carbazole and pyridine construction unit material
CN113549023A (en) Organic compound and application thereof
CN114773210B (en) Organic compound and application thereof
CN116391008A (en) Carbazole-containing compound and organic electroluminescent device
KR20140021294A (en) Novel compounds and organic light emitting device display using the same
WO2018166096A1 (en) Organic light-emitting device and method for manufacturing same
CN112574162A (en) Dibenzo-pyranyl compound, preparation method thereof and organic electroluminescent device
CN111848589B (en) Xanthone derivative, preparation method and application thereof, and light-emitting device comprising xanthone derivative
CN113999215A (en) Organic compound and application thereof
CN114106026A (en) Double-boron organic luminescent material and application of luminescent device
CN115572303A (en) Organic light-emitting compound and application thereof
CN109748913B (en) Electroluminescent material based on carbazole and pyridine building units
CN112079833A (en) Organic electroluminescent compound and preparation method and application thereof
CN112759571A (en) Organic electroluminescent compound, preparation method thereof and organic electroluminescent device comprising organic electroluminescent compound
CN111377904A (en) Organic electroluminescent material and device
CN111233840A (en) Quinoxaline derivative and application thereof in organic light-emitting device
CN111777609B (en) Anthracene-containing derivative and preparation method and application thereof
CN114621193B (en) Organic light-emitting material, method for manufacturing the same, and OLED device
CN109970732B (en) Electroluminescent material and application thereof in photoelectric device
CN112661701B (en) Pterenes electron transport material, preparation method thereof 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