CN107936949B - Fluorescent OLED material and application thereof in electroluminescent device - Google Patents

Fluorescent OLED material and application thereof in electroluminescent device Download PDF

Info

Publication number
CN107936949B
CN107936949B CN201711106007.1A CN201711106007A CN107936949B CN 107936949 B CN107936949 B CN 107936949B CN 201711106007 A CN201711106007 A CN 201711106007A CN 107936949 B CN107936949 B CN 107936949B
Authority
CN
China
Prior art keywords
layer
electroluminescent device
thickness
use according
oled material
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.)
Active
Application number
CN201711106007.1A
Other languages
Chinese (zh)
Other versions
CN107936949A (en
Inventor
廖良生
胡云
袁熠
蒋佐权
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.)
Suzhou University
Original Assignee
Suzhou University
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 Suzhou University filed Critical Suzhou University
Priority to CN201711106007.1A priority Critical patent/CN107936949B/en
Publication of CN107936949A publication Critical patent/CN107936949A/en
Application granted granted Critical
Publication of CN107936949B publication Critical patent/CN107936949B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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

Landscapes

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

Abstract

The invention provides a fluorescent OLED material and application thereof in an electroluminescent device. The material has high carrier mobility, small band gap and low HOMO value, and is beneficial to carrier injection. The synthesis yield is high, and the material has a simple synthesis route, is easy to operate and has good industrial prospects. The OLED material can be suitable for an organic electroluminescent device and used as a doped layer or a main body in a light-emitting layer or used as any one of the light-emitting layer and a transmission layer independently. The organic electroluminescent device prepared by the OLED material can realize the effects of deep red light, low voltage and high efficiency.

Description

Fluorescent OLED material and application thereof in electroluminescent device
Technical Field
The invention belongs to the field of organic electroluminescent materials and devices, and particularly relates to a fluorescent OLED material and application thereof in an electroluminescent device.
Background
The red light irradiation with the wavelength of 630-700 nm has photochemical effect on organisms, so the red light therapeutic apparatus is widely applied to hospitals and families. The mitochondria absorb the red light most in the cell, and after the red light is irradiated, the catalase activity of the mitochondria is increased, so that the metabolism of the cell can be increased; increasing the content of glycogen, the synthesis of protein and the decomposition of adenosine triphosphate, thereby enhancing the regeneration of cells and promoting the healing of wounds and ulcers; meanwhile, the phagocytosis of white blood cells is increased, and the immune function of the body is improved. Therefore, the traditional Chinese medicine composition can be used for treating various diseases clinically.
The red light is the wave band which is transmitted furthest in the spectrum, has strong penetrating power, and is the farthest color which can be transmitted in the foggy and rainy days, so the red light is important for safety, and the steering lamp and the tail lamp adopt the relatively striking red light.
Currently, the main methods for obtaining red light are red LEDs, fluorescent lamps and filters. Organic Light Emitting Diodes (OLEDs) have the advantages of low operating voltage, low heat generation, thin panels, and the like, have the tendency to replace traditional light sources, and can customize spectral colors by designing novel light emitting materials. Organic electroluminescence is mainly divided into fluorescence and phosphorescence, with a probability of singlet and triplet excitons of 1:3, and a theoretical quantum yield of 100% for phosphorescence, while the theoretical limit of fluorescence has also been achieved by regulating the spacing of singlet and triplet states to achieve a quantum yield of 100%. However, fluorescent materials are more cost effective because they do not contain precious metals.
Disclosure of Invention
The invention mainly aims to provide a red organic fluorescent material and an OLED device applying the red organic fluorescent material.
In order to achieve the purpose, the structural formula of the fluorescent OLED material provided by the invention is shown as a formula (1),
formula (1)
The invention provides a method for preparing a compound shown as a formula (1), which comprises the following steps:
mixing 5-bromoacenaphthylene-1, 2-diketone and (4- (diphenylamine) phenyl) boric acid in a solvent, wherein the solvent is one of toluene, N-dimethylformamide and tetrahydrofuran. The reaction gas is inert gas, and the inert gas is nitrogen or argon. Adding catalyst of palladium acetate and palladium tetrakis (triphenylphosphine) (Pd (PPh)3)4) Bis (dibenzylideneacetone) palladium (Pd (dba)2) One kind of (1).
5-bromoacenaphthylene-1, 2-dione: (4- (diphenylamine) phenyl) boronic acid: the feeding molar using ratio of the catalyst is 2:2.4:0.092, 2.2:2.4:0.092, 2.3:2.4:0.092, 2.4:2.4:0.092, 2.5:2.4: 0.092.
After the mixed solution was heated at 50 ℃ for 10 minutes, Na was added thereto at a concentration of 2M2CO3An aqueous solution. Na (Na)2CO3The volume ratio of the aqueous solution to the tetrahydrofuran solvent is 1: 4. The reaction time is 12-24 hours, and the reaction temperature is 50-60 ℃.
The invention provides an application of the fluorescent OLED material in preparing an electroluminescent device, wherein the fluorescent OLED material is a material for forming an organic light-emitting layer.
Furthermore, the electroluminescent device is composed of a substrate, an anode layer, a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer and a cathode layer.
Preferably, the material of the substrate is glass or flexible plastic.
Preferably, the material of the anode layer is an inorganic material or an organic conductive polymer material; wherein the inorganic material is one of indium tin oxide, zinc tin oxide or silver; the organic conductive polymer is one of polythiophene, sodium polyvinylbenzene sulfonate and polyaniline.
Preferably, the hole injection material is 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-Hexaazatriphenylene (HATCN) with the thickness of 5-10 nm.
Preferably, the hole transport material is 1, 1-bis [4- [ N, N ' -bis (p-tolyl) amino ] phenyl ] cyclohexane (TAPC) or N ' -diphenyl-4, 4' -biphenyldiamine (NPB) with a thickness of 30-100 nm.
Preferably, the material of the organic light-emitting layer is a mixture consisting of the fluorescent OLED material and 3, 4-bis (4- (diphenylamine) phenyl) acenaphthopyrazine-8, 9-dicarbonitrile (TPBi), and the mass ratio of the two is 0.05-0.3; or the material of the organic light-emitting layer consists only of the fluorescent OLED material as claimed in claim 1, with a thickness of 10-30 nm.
Preferably, the electron transport material is 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi) or tris (8-hydroxyquinoline) aluminum (Alq 3) with a thickness of 35-100 nm.
Preferably, the electron injection material is 8-hydroxyquinoline-lithium (Liq) with a thickness of 2 nm.
Preferably, the cathode layer material is one or two combinations of gold, silver, copper, aluminum or magnesium, and has a thickness of 100-200 nm.
The chemical structure of the compound used in the invention is as follows:
has the advantages that: the invention provides a fluorescent OLED material consisting of electron withdrawing groups and electron donating groups. The material has high carrier mobility, small band gap and low HOMO value, and is beneficial to carrier injection. The synthesis yield is high, the cost can be reduced, and the material has a simple synthesis route, is easy to operate and has good industrial prospects. The OLED material can be suitable for an organic electroluminescent device and used as a doped layer or a main body in a light-emitting layer or used as any one of the light-emitting layer and a transmission layer independently. The organic electroluminescent device prepared by the OLED material can realize the effects of deep red light, low voltage and high efficiency.
Drawings
FIG. 1 is a schematic view of the structure of an OLED device employed in the present invention.
FIG. 2 Oxidation potential test of formula (1) prepared in example 1.
Fig. 3 an electro-luminescence spectrum of an electroluminescent device prepared in example 2.
Fig. 4 a graph of current versus voltage for an electroluminescent device prepared in example 2.
Fig. 5 an electro-luminescence spectrum of an electroluminescent device prepared in example 3.
Fig. 6 is a graph of voltage versus luminance for an electroluminescent device prepared in example 3.
Fig. 7 an electro-luminescence spectrum of an electroluminescent device prepared in comparative example 1.
FIG. 8 is a graph of current versus voltage for the electroluminescent device prepared in comparative example 1.
Detailed Description
The present invention is further described below with reference to specific examples, which are only exemplary and do not limit the scope of the present invention in any way. The method is a conventional method unless otherwise specified. The starting materials are commercially available from the open literature unless otherwise specified.
Example 1
The structural formula of the fluorescent OLED material provided by the invention is shown as a formula (1),
formula (1)
The invention provides a method for preparing a compound shown as a formula (1), which comprises the following steps:
5-bromoacenaphthylene-1, 2-dione (0.52 g, 2.0 mmol), (4- (diphenylamine) phenyl) boronic acid (0.69 g, 2.4 mmol) was mixed in 60 mL of Tetrahydrofuran (THF) solvent. The reaction environment is inert gas, and the inert gas is argon. Adding catalyst Pd (PPh)3)4（0.092 mmol）。
After the mixed solution was heated at 50 ℃ for 10 minutes, Na was added thereto at a concentration of 2M2CO315 mL of the aqueous solution. The reaction time was 12 hours and the reaction temperature was 50 ℃. After waiting for the temperature of the mixed liquid to drop to room temperature, THF was removed under vacuum, and 100mL of methylene chloride was added to the residual solid, followed by washing with 100mL of water, which was repeated 3 times, and finally water was removed under vacuum. The resulting residue was purified by column on silica gel, eluting with petroleum ether/dichloromethane (1/1, v/v) to give a red solid. The yield thereof was found to be 84.71%.
The structure and performance detection results of the product are as follows:
（1）1H NMR (400 MHz, CD2Cl2): δ 8.48 (d, J = 8.5 Hz, 1H), 8.12 (d, J = 7.3 Hz, 1H), 8.07 (d,J = 6.9 Hz, 1H), 7.82 (d, J = 7.5 Hz, 2H), 7.50 (d, J = 8.5 Hz, 2H), 7.33 (t,J = 7.8 Hz, 4H), 7.21 (t, J = 7.0 Hz, 6H), 7.11 (t, J = 7.3 Hz, 2H).
（2）13C NMR (400 MHz, CD2Cl2): δ 189.15, 188.04, 149.07, 147.70, 147.04, 146.43, 132.02, 131.67, 130.76, 129.86, 129.65, 129.26, 129.00,128.70, 127.80, 125.49, 124.11, 122.89, 122.33, 122.06, 54.39, 54.12, 53.85,53.58 and 53.31.
(3) Mass Spectrometry MS (MALDI-TOF) M/z 425.12 [ M ] +.
(4) The glass transition temperature Tg is 90 ℃;
(5) ultraviolet absorption wavelength: 303nm, 422 nm;
(6) fluorescence emission wavelength: 645 nm;
(7) HOMO value: 5.3 eV, cyclic voltammetry, as shown in FIG. 2.
Example 2
And preparing an electroluminescent device. Use of the compound of formula (1) prepared in example 1 for the preparation of an electroluminescent device in which the compound of formula (1) of the present invention is a material constituting an organic light-emitting layer;
the first step is as follows: the ITO transparent conductive glass substrate is subjected to ultrasonic treatment in a commercial cleaning agent, washed in deionized water, repeatedly washed three times by using the deionized water, acetone and ethanol, and baked in a clean environment until water is completely removed. Then the ozone is ultraviolet for 10 minutes.
The second step is that: placing the treated ITO conductive glass in a vacuum chamber, and vacuumizing to 4.0 multiplied by 10-4Pa or so.
And thirdly, evaporating a hole injection material HATCN with the thickness of 10 nm, a hole transport material TAPC with the thickness of 50 nm and the evaporation rate of 2 Å/s in sequence.
And fourthly, evaporating a luminescent layer, namely the material with the thickness of 20 nm and the evaporation rate of 2 Å/s, of the formula (1).
And fifthly, vacuum evaporating a layer of TPBi on the organic light-emitting layer to be used as an electron transport layer, wherein the evaporation rate is 2 Å/s, and the thickness of a coating film is 50 nm.
Sixthly, vacuum evaporating Liq on the electron transport layer to form an electron injection layer with the thickness of 2nm and the evaporation rate of 0.2 Å/s,
the seventh step: and aluminum is evaporated on the electron transport layer in vacuum to serve as a cathode of the device, and the thickness of the device is 120 nm.
The chemical structure of the material used in example 2 is as follows:
the electroluminescent device prepared in example 2 has an electro-luminescence spectrum as shown in fig. 3.
The prepared device has a light-emitting peak value of 645nm, and the formula (1) is good as a light-emitting layer, the material has small band gap and low HOMO value, and is favorable for carrier injection, so that the device has low working voltage, and the current density reaches 100 mA/cm at 9V2. The current versus voltage curve for the device is shown in fig. 4. The device spectrum is suitable for being manufactured into a tail lamp and a prompt lamp, and practical application is met.
Example 3
The difference from the example 2 is that in the fourth step, the light-emitting layer is a doped layer, the structural material of the formula (1) is used as a host, the 3, 4-bis (4- (diphenylamine) phenyl) acenaphthopyrazine-8, 9-dicarbonitrile of the formula (2) is used as an object, double-source co-evaporation is carried out, the ratio of the mass of the object to the mass of the host is 1:4, the thickness of the layer is 20 nm, and the evaporation rate is 2 Å/s.
The structure of formula (2) is as follows:
the electroluminescent device prepared in example 3 has an electro-luminescence spectrum as shown in fig. 5, and a voltage-luminance relationship as shown in fig. 6.
The device thus prepared had an emission peak at 735 nm, indicating that the formula (1) is also excellent as a host. The material has small band gap and low HOMO value, is favorable for carrier injection, and can realize 38 cd/cm under the drive of 9V2Thereby meeting the practical application.
Comparative example 1
The difference from example 2 is that in the fourth step, the light-emitting layer uses 4,4' -bis (9H-carbazol-9-yl) biphenyl (CBP) which is commonly used as a host material, formula (2) is used as a guest material, and double-source co-evaporation is carried out, wherein the ratio of the guest mass to the host mass is 1:4, the thickness of the layer is 20 nm, and the evaporation rate is 2 Å/s.
The molecular structure of CBP is as follows:
the electroluminescent device prepared in comparative example 1 had an electro-luminescence spectrum as shown in fig. 7. The current versus voltage curve for the device is shown in fig. 8. At 9V, the current density is only less than 10 mA/cm2 。
The drive voltage required for example 3 is less than that for the device of comparative example 1 at the same current density. It is explained that formula (1) is more suitable for manufacturing deep red devices than CBP. And the luminous peak of the device manufactured by the formula (1) is more red-shifted (long wavelength and long propagation distance).

Claims (10)

1. A fluorescent OLED material is characterized in that the structure of the material is shown as formula (1):
formula (1).
2. Use of the fluorescent OLED material of claim 1 in the preparation of an electroluminescent device, wherein: in the electroluminescent device, the fluorescent OLED material is a material for forming an organic light-emitting layer.
3. Use according to claim 2, characterized in that: the electroluminescent device comprises a substrate, an anode layer, a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer and a cathode layer.
4. Use according to claim 3, characterized in that: the substrate is made of glass or flexible plastic.
5. Use according to claim 3, characterized in that: the anode layer is made of an inorganic material or an organic conductive polymer material; wherein the inorganic material is one of indium tin oxide, zinc tin oxide or silver; the organic conductive polymer is one of polythiophene, sodium polyvinylbenzene sulfonate and polyaniline.
6. Use according to claim 3, characterized in that: the hole injection layer is made of 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene and has the thickness of 5-10 nm.
7. Use according to claim 3, characterized in that: the hole transport layer is made of 1, 1-bis [4- [ N, N ' -bis (p-tolyl) amino ] phenyl ] cyclohexane or N ' -diphenyl-4, 4' -biphenyldiamine and has the thickness of 30-100 nm.
8. Use according to claim 3, characterized in that: the organic light-emitting layer is made of a mixture of the fluorescent OLED material in the claim 1 and 3, 4-bis (4- (diphenylamine) phenyl) acenaphthopyrazine-8, 9-dicarbonitrile, and the mass ratio of the two is 0.05-0.3; or the material of the organic light-emitting layer consists only of the fluorescent OLED material as claimed in claim 1, with a thickness of 10-30 nm.
9. Use according to claim 3, characterized in that: the electron transport layer is made of 1,3, 5-tri (1-phenyl-1H-benzimidazole-2-yl) benzene or tri (8-hydroxyquinoline) aluminum, and the thickness is 35-100 nm.
10. Use according to claim 3, characterized in that: the material of the electron injection layer is 8-hydroxyquinoline-lithium with the thickness of 2nm, the material of the cathode layer is one or the combination of two of gold, silver, copper, aluminum or magnesium with the thickness of 100-200 nm.
CN201711106007.1A 2017-11-10 2017-11-10 Fluorescent OLED material and application thereof in electroluminescent device Active CN107936949B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201711106007.1A CN107936949B (en) 2017-11-10 2017-11-10 Fluorescent OLED material and application thereof in electroluminescent device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201711106007.1A CN107936949B (en) 2017-11-10 2017-11-10 Fluorescent OLED material and application thereof in electroluminescent device

Publications (2)

Publication Number Publication Date
CN107936949A CN107936949A (en) 2018-04-20
CN107936949B true CN107936949B (en) 2019-12-24

Family

ID=61934747

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201711106007.1A Active CN107936949B (en) 2017-11-10 2017-11-10 Fluorescent OLED material and application thereof in electroluminescent device

Country Status (1)

Country Link
CN (1) CN107936949B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111059512A (en) * 2019-12-24 2020-04-24 上海晶合光电科技有限公司 Automobile tail lamp based on OLED and preparation method thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101514262A (en) * 2009-03-19 2009-08-26 大连理工大学 Ethylene naphthalene and paradiazine dye and application thereof to dye-sensitized solar cells.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101514262A (en) * 2009-03-19 2009-08-26 大连理工大学 Ethylene naphthalene and paradiazine dye and application thereof to dye-sensitized solar cells.

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Over 10% EQE Near-Infrared Electroluminescence Based on a Thermally Activated Delayed Fluorescence Emitter;Yi Yuan et al.;《Adv. Funct. Mater》;20170502;第27卷;1700986 *
Tunable Dipolar Acenaphthopyrazine Derivatives Containing Diphenylamine;Tai-Hsiang Huang et al.;《Chem. Mater.》;20041118;第16卷;5387-5393 *

Also Published As

Publication number Publication date
CN107936949A (en) 2018-04-20

Similar Documents

Publication Publication Date Title
CN104844587A (en) Conjugated compound comprising phenoxathiin structure and preparation method thereof and organic electroluminescence light emitting diode device
CN110437081B (en) Organic compound containing tricycloheptane, preparation method thereof and organic electroluminescent device comprising the same
CN114649489B (en) Red light electroluminescent device based on bipyridine phenazine heat-activated delayed fluorescent material
WO2020211125A1 (en) Thermally-activated delayed fluorescent material and preparation method therefor, and organic light-emitting diode device
CN114436754B (en) Organic compound and application thereof
CN113549023A (en) Organic compound and application thereof
CN111793063A (en) Organic light-emitting molecules and application thereof in organic light-emitting diode
CN102786438B (en) Cyano anthraquinone derivatives, preparation method and organic electroluminescent devices thereof
CN112979616B (en) Benzimidazole compound and preparation method and application thereof
CN113999162A (en) Organic electroluminescent device and organic compound
CN107936949B (en) Fluorescent OLED material and application thereof in electroluminescent device
CN109503487B (en) Dihydrobenzandazole compound, organic electroluminescent device and display device
WO2020155525A1 (en) Thermally activated delayed fluorescent material, organic electroluminescent device, and display panel
CN112538049B (en) Blue fluorescent material with high exciton utilization rate and preparation and application thereof
CN112480077B (en) Compound for organic luminescence and application thereof
CN109678799B (en) Dihydrobenzandazole compound, organic electroluminescent device and display device
CN110372676B (en) Dibenzofuran main body material and preparation method and application thereof
CN111018874B (en) Hole transport material, preparation method thereof and organic light emitting diode device
CN106188024A (en) Luminescent material and preparation method thereof and the Organic Light Emitting Diode using this luminescent material
CN110028505B (en) Organic electroluminescent compound, preparation method thereof and organic electroluminescent device
CN103030596A (en) Dihydracridine material and application thereof
WO2022088113A1 (en) Doped electronic device based on green thermally activated delayed fluorescence material, and manufacturing method therefor
CN107325108B (en) Xanthene spiroazaanthrone organic electroluminescent material, preparation method and application thereof
CN110372683A (en) A kind of electroluminescent organic material and the preparation method and application thereof
CN110317187B (en) Organic main body material and preparation method and application thereof

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
GR01 Patent grant
GR01 Patent grant