CN114437023B - Organic electroluminescent compound and application thereof - Google Patents
Organic electroluminescent compound and application thereof Download PDFInfo
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Abstract
The invention provides an organic electroluminescent compound and application thereof, wherein the structure of the organic electroluminescent compound is shown as a formula I: therein L, L 1 、L 2 Independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; ar (Ar) 1 、Ar 2 Independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl. The organic electroluminescent device prepared from the organic electroluminescent compound provided by the invention has the characteristics of high current efficiency and long service life.
Description
Technical Field
The invention belongs to the field of organic electroluminescent materials, in particular to an organic electroluminescent compound and application thereof, and particularly relates to an organic electroluminescent compound with high current efficiency and application thereof.
Background
Recently, as the size of displays increases, flat display elements occupying less space are increasingly interesting. In the art, technology of an organic light emitting display including an Organic Light Emitting Diode (OLED) as a flat display element has been rapidly developed. The organic light emitting diode emits light by annihilating a pair of holes and electrons generated by injecting holes and electrons from a hole injection electrode (anode) and an electron injection electrode (cathode) into an emission layer interposed between the anode and the cathode. Such an organic light emitting diode can be formed on a flexible transparent substrate such as plastic, can be operated at a low voltage, consumes relatively low power, and has good color reproduction.
CN105849107B discloses a novel organic electroluminescent compound and an organic electroluminescent device comprising said compound. The organic electroluminescent compounds according to the invention can be used in a light emitting layer and have excellent light emitting efficiency; and the organic electroluminescent device comprising the organic electroluminescent compounds according to the invention has a long service life and improved current efficiency and power efficiency.
CN111471062a discloses a diboron-containing organic electroluminescent compound and application thereof in organic electroluminescent devices, and belongs to the technical field of semiconductors. The diboron-containing organic electroluminescent compounds are selected from structures represented by the general formula (1): the invention also discloses application of the diboron-containing organic electroluminescent compound in an organic electroluminescent device. The compound consists of boron groups, has high rigidity, and has the characteristics of difficult crystallization, difficult aggregation and good film forming property among molecules. When the compound is used as a luminescent layer material of an organic electroluminescent device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; at the same time, the life of the device is obviously prolonged.
As the demands of people for organic electroluminescent devices are gradually increased, the demands for materials for novel organic electroluminescent devices are more urgent. Therefore, how to provide a material for an organic electroluminescent device with high efficiency and long service life becomes a problem to be solved urgently.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide an organic electroluminescent compound and application thereof, in particular to an organic electroluminescent compound with high current efficiency and application thereof. The organic electroluminescent device prepared from the organic electroluminescent compound provided by the invention has the characteristics of high current efficiency and long service life.
In order to achieve the aim of the invention, the invention adopts the following technical scheme:
in a first aspect, the present invention provides an organic electroluminescent compound having a structure according to formula I:
therein L, L 1 、L 2 Independent and independentIs selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C3-C30 heteroarylene.
Ar 1 、Ar 2 Independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl.
The organic electroluminescent device made of the organic electroluminescent compound with the specific structure has the characteristics of high current efficiency and long service life.
Preferably, the organic electroluminescent compound has a general structural formula as shown in any one of the following:
Preferably L, L 1 、L 2 Independently selected from a single bond or phenylene.
Preferably Ar 1 、Ar 2 Independently selected from hydrogen, deuterium, halogen or any of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl (selected from
) Dimethylfluorenyl (9, 9-dimethylfluorenyl)Self->
) Diphenyl fluorenyl (9, 9-diphenyl fluorenyl, selected from +.>
) Spirobifluorenyl, dibenzofuran substituted phenyl, dibenzothiophene substituted phenyl, dimethylfluorenyl substituted phenyl, benzocarbazolyl, benzonaphthofuranyl, and benzonaphthothiophenyl.
Preferably, the substituted substituent is selected from any one of deuterium, halogen, cyano, methyl or phenyl.
Preferably, the organic electroluminescent compound is selected from any one of the following structures:
the above organic electroluminescent compounds can be exemplarily prepared by a method comprising the steps of:
when L is selected from single bond
Coupling to obtain the organic electroluminescent compound;
l is selected from the group consisting of substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene
And->
Coupling, then with->
Coupling to obtain the organic electroluminescent compound
In a second aspect, the present invention provides the use of an organic electroluminescent compound as described above in the preparation of an organic electroluminescent diode.
In a third aspect, the present invention provides an organic light emitting diode comprising a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, the material of the organic layer comprising at least one organic electroluminescent compound as described above.
Preferably, the organic layer includes a hole transport layer, a light emission auxiliary layer, a light emitting layer, a hole blocking layer, and an electron transport layer, which are sequentially stacked.
Preferably, the hole transport layer comprises an organic electroluminescent compound as described above.
Preferably, the light-emitting auxiliary layer comprises an organic electroluminescent compound as described above.
In a fourth aspect, the present invention provides an organic electroluminescent device comprising an organic light emitting diode as described above.
In a fifth aspect, the present invention also provides an application of the organic electroluminescent device described above in preparing an optoelectronic device, a medical device, an optical fiber, an illumination device, an electrophotographic photoreceptor, a photoelectric converter, an organic solar cell, a switching element, an organic light emitting field effect transistor, an image sensor or a dye laser.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides an organic electroluminescent compound with a specific structure, and an organic electroluminescent device prepared from the organic electroluminescent compound has the characteristics of high current efficiency and long service life.
Drawings
Fig. 1 is a schematic view of the structure of an organic electroluminescent device in an application example, in which a 1-substrate, a 2-anode, a 3-hole injection layer, a 4-hole transport layer, a 5-light-emitting auxiliary layer, a 6-light-emitting layer, a 7-electron transport layer, an 8-electron injection layer, and a 9-cathode are used.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
As used in the present invention, the term "organic electroluminescent compound" means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device as needed.
As used in the present invention, the term "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent element and may contain at least one compound. The organic electroluminescent material may be contained in any layer constituting the organic electroluminescent element, if necessary. For example, the organic electroluminescent material may be a hole injecting material, a hole transporting material, an electron blocking material, a light emitting auxiliary material, a light emitting layer material (including a host material and a doping material), an electron buffer material, a hole blocking material, an electron transporting material, an electron injecting material, or the like.
The organic electroluminescent material disclosed in the present invention may comprise at least one compound represented by formula 1. Although not limited thereto, the compound having formula 1 may be included in the hole transport layer, and/or the compound having formula 1 may be included in the light emitting auxiliary layer, and is not limited thereto.
Hereinafter, each layer of the organic electroluminescent element comprising the compound of formula 1 according to the present invention will be described.
Substrate board
The organic EL element is generally fabricated on a light-transmitting substrate. The light-transmitting substrate is a substrate for supporting an organic EL element, and preferably has a transmittance of light in the visible region of 400 to 700nm of 50% or more, and more preferably a smooth substrate is used.
Examples of such a light-transmitting substrate include a glass plate and a synthetic resin plate. Examples of the glass sheet include a sheet formed of soda lime glass, barium strontium-containing glass, lead glass, aluminum silicate glass, borosilicate glass, barium borosilicate glass, quartz, and the like. Examples of the synthetic resin sheet include sheets of polycarbonate resin, acrylic resin, polyethylene terephthalate resin, polyether sulfide resin, polysulfone resin, and the like.
Anode
The anode functions to inject holes into the hole transport layer or the light emitting layer, and it is effective to have a work function of 4eV or more (preferably 4.45eV or more). Specific examples of the anode material include carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and the like, alloys thereof, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole.
Cathode electrode
As the cathode, a cathode having a metal, an alloy, a conductive compound, or a mixture thereof, which has a small work function (less than 4 eV), as an electrode material can be used. Specific examples of such electrode materials include magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, and alloys thereof, and are not particularly limited. Examples of the alloy include magnesium/silver, magnesium/indium, lithium/aluminum, and the like, and these are not particularly limited. The ratio of the alloy is controlled by the temperature, atmosphere, vacuum degree, etc. of the vapor deposition source, and an appropriate ratio is selected. The anode and the cathode may be formed by two or more layers, as required.
Light-emitting layer
The light-emitting layer has the functions of carrier injection, carrier transmission and light emission. The light emitting layer material includes a host material, a guest material including a phosphorescent guest material, a fluorescent guest material, a TADF guest material, and the like.
Hole injection layer/hole transport layer
The hole injection layer/hole transport layer is used for injecting into the light-emitting layerHoles, a layer that transports holes to the light emitting region, have a large hole mobility and an ionization energy of usually 5.7eV or less. As such a hole injection layer/hole transport layer, a material that transports holes to the light-emitting layer with a lower electric field strength is preferable, and it is further preferable that the hole mobility is, for example, 10 to 4cm when an electric field of 104 to 106V/cm is applied 2 and/V.sec or more. Examples of materials known as the hole transport layer material include bis (N- (1-naphthyl-N-phenyl)) benzidine (α -NPD), N '-bis (naphthalen-1-yl) -N, N' -biphenylbenzidine (NPB), or N, N '-biphenyl-N, N' -bis (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine (TPD), and the like.
Light-emitting auxiliary layer
The light-emitting auxiliary layer is used for reducing potential barrier of hole transmission to the light-emitting layer, is also beneficial to blocking electrons, avoids electrons overflowing from the light-emitting layer to the hole transmission layer, and improves light-emitting efficiency.
Electronic buffer layer
The electron buffer layer helps to block holes in the light emitting layer and also helps to transport electrons to the light emitting layer so as to promote the combination of electrons and holes in the light emitting layer and improve the light emitting efficiency.
Electron injection layer/electron transport layer
The electron injection layer/electron transport layer is a layer that contributes to injection of electrons into the light-emitting layer and transport of electrons to the light-emitting region, and has high electron mobility. The adhesion-improving layer is an electron injection layer containing a material that adheres particularly well to the cathode.
Specific examples of the material used for the electron injection layer include LiF, liq, li 2 O, baO, naCl, csF, etc., and these are not particularly limited.
The function of the OLED may be achieved by combining the various layers described above, or some of the layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sublayers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In order to form each layer of the organic electroluminescent device disclosed in the present invention, a dry film forming method such as vacuum evaporation, sputtering, plasma, ion plating method, or the like, or a wet film forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating method, or the like may be used. The organic electroluminescent compounds disclosed in the present invention can be formed into a film by a co-evaporation method or a mixture evaporation method.
The product is applied to photoelectricity, medicine, biotechnology, optical fiber, lighting equipment, an electrophotographic photoreceptor, a photoelectric converter, an organic solar cell, a switching element, an organic light emitting field effect transistor, an image sensor or a dye laser.
Definition of terms for substituents
As used in the present invention, the term "halogen" may include fluorine, chlorine, bromine or iodine.
As used herein, the term "C1-C30 alkyl" refers to monovalent substituents derived from straight or branched chain saturated hydrocarbons having from 1 to 30 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.
As used herein, the term "C3-C30 cycloalkyl" refers to a mono-or polycyclic hydrocarbon derived from a hydrocarbon having from 1 to 30 ring backbone carbon atoms, which cycloalkanes may include cyclopropyl, cyclobutyl, adamantyl, and the like.
Aryl, arylene in the present invention includes monocyclic, polycyclic or fused ring aryl groups, which may be interrupted by short non-aromatic units, and may contain spiro structures including, but not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, and the like.
Heteroaryl, heteroarylene in the present invention includes monocyclic, polycyclic or fused ring heteroaryl groups, which rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, sulfur. Including, but not limited to, furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, derivatives thereof, and the like.
As used herein, the term "substituted" refers to a compound in which a hydrogen atom is replaced with another substituent. The position is not limited to a specific position as long as hydrogen at the position can be substituted with a substituent. When two or more substituents are present, the two or more substituents may be the same or different.
As used herein, unless otherwise indicated, hydrogen atoms include protium, deuterium, and tritium.
In the present invention, the definition of a group defines a range of carbon atoms, the number of carbon atoms being any integer within the defined range, for example, a C6-C60 aryl group, and the number of carbon atoms representing the aryl group may be any integer within the range of 6-60 inclusive, for example, 6, 8, 10, 15, 20, 30, 35, 40, 45, 50, 55, 60, or the like.
Example 1
The embodiment provides an organic electroluminescent compound, and the synthetic route is as follows:
the method comprises the following specific steps:
synthesis of intermediate 2-1: in a 250mL three-necked flask, add raw material 1 (10 mmol), raw material 2 (10 mmol), toluene 60mL, ethanol 20mL, water 20mL, tetraphenylphosphine palladium (0.4 mmol), potassium carbonate (20 mmol), heat to 80℃for 5 hours, cool to room temperature, and use ethyl acetate and H 2 The organic layer was extracted with O. The extracted organic layer was dried over MgSO 4 Dried and filtered. The filtrate was concentrated under reduced pressure, and purified by silica gel column chromatography (DCM/hexane) to give intermediate 2-1 (2.43 g, yield: 47%).
Synthesis of intermediate 2-2: to 250mL was N-charged 2 To a three-necked flask of (2-1) (10 mmol), 40mL of anhydrous methylene chloride, and iron chloride (0.1 mol) were added and stirred for 1 hour, followed by 20mL of methanol, and after completion of the reaction, cooled to room temperature, the organic layer was separated, concentrated under reduced pressure and purified by silica gel column chromatography (DCM/hexane) to give intermediate 2-2 (2.98 g, yield: 58%).
Synthesis of Compound 2: to 250mL was N-charged 2 To a two-necked flask of (a) was added intermediate 2-2 (10 mmol), starting material 3 (10 mmol), sodium t-butoxide (15 mmol), tris (dibenzylideneacetone) dipalladium (0) (0.2 mmol), (8% eq) S-phos (0.8 mmol), and toluene 80mL, followed by stirring under reflux. After cooling to room temperature, the mixture was taken up with ethyl acetate and H 2 The organic layer was extracted with O. The extracted organic layer was dried over MgSO 4 Dried and filtered. The filtrate was concentrated under reduced pressure, and purified by silica gel column chromatography (DCM/hexane), followed by recrystallization from a DCM/acetone mixture, to give compound 2 (5.50 g, yield: 81%).
Characterization data are as follows:
MS(APCI)m/z[M+H] + ：680.44。
example 2
The embodiment provides an organic electroluminescent compound, and the synthetic route is as follows:
the method comprises the following specific steps:
synthesis of Compound 4, synthesis of Compound 2, except that raw material 4 was used instead of raw material 3, compound 4 was obtained (6.00 g, yield: 78%).
Characterization data are as follows:
MS(APCI)m/z[M+H] + ：770.38。
example 3
The embodiment provides an organic electroluminescent compound, and the synthetic route is as follows:
the method comprises the following specific steps:
synthesis of Compound 13, synthesis of Compound 2, was repeated except that raw material 5 was used instead of raw material 3 to obtain Compound 13 (6.28 g, yield: 79%).
Characterization data are as follows:
MS(APCI)m/z[M+H] + ：796.67。
example 4
The embodiment provides an organic electroluminescent compound, and the synthetic route is as follows:
the method comprises the following specific steps:
synthesis of intermediate 20-1: the synthesis of intermediate 2-1 is different in that raw material 6 is used for replacing raw material 2, intermediate 2-2 is used for replacing raw material 1, and intermediate 20-1 (2.84 g, yield: 52%);
synthesis of Compound 20 and Synthesis of Compound 2, except that raw material 7 was used instead of raw material 3, intermediate 20-1 was used instead of intermediate 2-2, to give Compound 20 (4.96 g, yield: 73%).
Characterization data are as follows:
MS(APCI)m/z[M+H] + ：680.47。
application examples 1-4 and comparative application example 1
The following application examples 1 to 4 and comparative application example 1 respectively provide an OLED having the following structure in which: the structure of the substrate (indium tin oxide (ITO) coated glass substrate)/Hole Injection Layer (HIL)/hole transport layer (HTL-1)/light emitting auxiliary layer (HTL-2)/light emitting layer (EML)/Electron Transport Layer (ETL)/optional Electron Injection Layer (EIL), and finally the cathode is shown in figure 1, wherein 1 is the substrate, 2 is the anode, 3 is the hole injection layer, 4 is the hole transport layer, 5 is the light emitting auxiliary layer, 6 is the light emitting layer, 7 is the electron transport layer, 8 is the electron injection layer, and 9 is the cathode.
The materials used are as follows:
the preparation method comprises the following steps:
1) Cleaning a substrate:
ultrasonic treating the glass substrate coated with the ITO transparent electrode in an aqueous cleaning agent (the components and the concentration of the aqueous cleaning agent are 10wt% of glycol solvent and 1wt% of triethanolamine), flushing in deionized water, ultrasonic degreasing in an acetone-ethanol mixed solvent (volume ratio is 1:1), baking in a clean environment until the water is completely removed, and then cleaning with ultraviolet light and ozone;
2) Vapor deposition:
placing the above glass substrate with anode in vacuum chamber, and vacuumizing to 1×10 -6 Up to 2X 10 -4 Vacuum evaporating a Hole Injection Layer (HIL) material on the anode layer film in a co-evaporation mode, wherein the mass ratio of PD to NPB is adjusted to be 0.1nm/s, and the evaporation thickness is 10nm;
3) Evaporating a hole transport layer (HTL-1) on the hole injection layer, wherein the evaporation rate is 0.1nm/s, and the thickness of the evaporated film is 60nm;
4) Evaporating a light-emitting auxiliary layer (HTL-2, respectively using the organic electroluminescent compounds provided in examples 1-4 and REF-1) on the hole transport layer at a deposition rate of 0.1nm/s and an evaporated film thickness of 20nm;
5) Evaporating an emitting layer (EML) on the emitting auxiliary layer, and evaporating a light emitting host material and a guest material in a co-evaporation mode, wherein the evaporation rate of the host material and the guest material is adjusted according to the mass ratio, the total evaporation rate is 0.1nm/s, and the total evaporation film thickness is 30nm;
6) Vacuum evaporating an Electron Transport Layer (ETL) on the luminescent layer, and adjusting the evaporating speed according to the mass ratio of the compound ET to LiQ, wherein the evaporating total speed is 0.1nm/s, and the evaporating total film thickness is 30nm;
7) Vacuum evaporating an Electron Injection Layer (EIL) on the electron transport layer, wherein the evaporation rate is 0.05nm/s, and the total film thickness of the evaporation is 1nm;
8) And evaporating a cathode on the electron injection layer, wherein the total evaporation rate is 0.1nm/s according to metal Al, and the total evaporation film thickness is 100nm.
Each of the application examples and comparative application examples was composed as follows
The drive voltage, current efficiency and lifetime of the OLEDs in the above examples were then tested using a PR 650 spectroscan luminance meter and a Keithley K2400 digital source meter system, with opto-electronic property test conditions: the current density was 10mA/cm 2 The method comprises the steps of carrying out a first treatment on the surface of the Life test: the current density was 10mA/cm 2 The time (in hours) for which the device brightness was reduced to 95% of the original brightness was recorded. The results were as follows:
the results show that the organic electroluminescent device prepared from the organic electroluminescent compound provided by the invention has the characteristics of high current efficiency and long service life compared with the conventional material.
The applicant states that the organic electroluminescent compounds according to the invention and their use are illustrated by the above examples, but the invention is not limited to, i.e. it is not meant that the invention must be practiced in dependence on the above examples. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited to the specific details of the above embodiments, and various simple modifications can be made to the technical solution of the present invention within the scope of the technical concept of the present invention, and all the simple modifications belong to the protection scope of the present invention.
In addition, the specific features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described further.
Claims (8)
1. An organic electroluminescent compound, wherein the structure of the organic electroluminescent compound is shown as formula I:
a formula I;
wherein L is selected from phenylene, L 1 、L 2 Selected from single bonds;
Ar 1 、Ar 2 independently selected from any one of substituted or unsubstituted phenyl, biphenyl, naphthyl, pyridyl, dibenzothienyl, dibenzofuranyl or dimethylfluorenyl;
the substituted substituent group is selected from any one of deuterium, halogen, cyano or methyl.
2. The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound has a general structural formula as shown in any one of the following:
3. The organic electroluminescent compound according to claim 2, wherein the organic electroluminescent compound has the following structural formula:
therein, L, L 1 、L 2 、Ar 1 、Ar 2 Is in accordance with claim 1.
4. The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is selected from any one of the following structures:
5. use of an organic electroluminescent compound according to any of claims 1 to 4 for the preparation of an organic electroluminescent diode.
6. An organic light-emitting diode comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer comprising a hole transporting layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, and an electron transporting layer, which are sequentially stacked, the light-emitting auxiliary layer comprising the organic electroluminescent compound according to any one of claims 1 to 4.
7. An organic electroluminescent device comprising the organic light emitting diode of claim 6.
8. Use of an organic electroluminescent device according to claim 7 for the preparation of a photovoltaic device, a medical device, an optical fiber, an illumination device, an electrophotographic photoreceptor, a photoelectric converter, an organic solar cell, a switching element, an organic light emitting field effect transistor, an image sensor or a dye laser.
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| CN105849107A (en) * | 2013-12-27 | 2016-08-10 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN111471062A (en) * | 2019-01-07 | 2020-07-31 | 江苏三月科技股份有限公司 | Organic electroluminescent compound containing double boron and application thereof in organic electroluminescent device |
| CN112430239A (en) * | 2019-08-26 | 2021-03-02 | 广州华睿光电材料有限公司 | Seven-membered ring structure-based compound, high polymer, mixture, composition, and organic electronic device |
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| US20160211456A1 (en) * | 2015-01-19 | 2016-07-21 | Luminescence Technology Corp. | PHENANTHRO[9,10-b]TETRAPHENYLENE DERIVATIVE AND USE THEREOF |
| KR101934470B1 (en) * | 2015-09-16 | 2019-03-25 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| KR20170141987A (en) * | 2016-06-16 | 2017-12-27 | 에스에프씨 주식회사 | An electroluminescent compound and an electroluminescent device comprising the same |
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| CN105849107A (en) * | 2013-12-27 | 2016-08-10 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN111471062A (en) * | 2019-01-07 | 2020-07-31 | 江苏三月科技股份有限公司 | Organic electroluminescent compound containing double boron and application thereof in organic electroluminescent device |
| CN112430239A (en) * | 2019-08-26 | 2021-03-02 | 广州华睿光电材料有限公司 | Seven-membered ring structure-based compound, high polymer, mixture, composition, and organic electronic device |
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