CN112442035A - Compound for organic light emitting material and organic electroluminescent device containing the same - Google Patents
Compound for organic light emitting material and organic electroluminescent device containing the same Download PDFInfo
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Abstract
A compound for an organic light-emitting material, characterized by having a structure shown in (1):
wherein R is1～R5Each independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C60 heteroaryl; x1～X7Each independently selected from C or N atoms, and the total number of N atoms is 3, wherein X6～X7At most one is an N atom; l is1And L2Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group orSubstituted or unsubstituted C3-C30 heteroarylene; ar (Ar)1And Ar2Each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C60 heteroaryl; when the above groups have substituents, the substituents are respectively and independently selected from one or more of halogen, C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, monocyclic aryl or fused ring aryl of C6-C30, monocyclic heteroaryl or fused ring heteroaryl of C3-C60.
Description
Technical Field
The invention relates to a novel organic compound, in particular to a compound for an organic light-emitting material and application thereof in an organic electroluminescent device.
Background
Organic Light Emission Diodes (OLED) devices are a kind of devices with sandwich-like structure, which includes positive and negative electrode films and Organic functional material layers sandwiched between the electrode films. And applying voltage to the electrodes of the OLED device, injecting positive charges from the positive electrode and injecting negative charges from the negative electrode, and transferring the positive charges and the negative charges in the organic layer under the action of an electric field to meet for composite luminescence. Because the OLED device has the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the field of novel display technology and novel illumination technology. At present, the technology is widely applied to display panels of products such as novel lighting lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with fast development and high technical requirements.
With the continuous advance of OLEDs in both lighting and display areas, much attention has been paid to the research on their core materials. This is because an efficient, long-lived OLED device is generally the result of an optimized configuration of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like.
In order to prepare an OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device need to be innovated, and photoelectric functional materials in the OLED device need to be continuously researched and innovated, so that functional materials with higher performance can be prepared. Based on this, the OLED material industry has been working on developing new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.
In current OLED screen manufacturers, a technical means of doping Liq (lithium octahydroxyquinoline) into an Electron Transport (ET) material layer is widely used to achieve low voltage and high efficiency of a device, and to improve the lifetime of the device. Liq mainly has the effect that a small amount of metal lithium can be reduced under the action of electrons injected from the cathode, so that the N-doping effect of the electron transport material is achieved, the injection effect of electrons is remarkably improved, and on the other hand, lithium ions can achieve the effect of improving the electron mobility of the ET material through the coordination effect of N atoms in the electron transport material, so that a device with the Liq doped with the ET has low working voltage and high luminous efficiency. The electron transport materials commonly used at present comprise single oxazole, thiazole, imidazole, triazole or triazine structures and the like.
Disclosure of Invention
Problems to be solved by the invention
In order to further satisfy the continuously increasing demand for the photoelectric properties of OLED devices and the energy saving demand of mobile electronic devices, new and efficient OLED materials need to be continuously developed, wherein the development of new electron transport materials with high electron injection capability and high mobility is of great significance.
Means for solving the problems
In order to solve the above problems in the prior art, the inventors have made intensive studies and found that the structure in which benzene/N hetero six-membered ring and N hetero five-membered ring are fused with each other is advantageous for electron injection, and has a good planar structure capable of improving electron transfer ability.
Specifically, the present invention provides a compound for an organic light emitting material, characterized by having a structure shown in (1):
wherein R is1～R5Each independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C60 heteroaryl; xl～X7Each independently selected from C or N atoms, and the number of N atoms is 3, wherein X6～X7At most one is an N atom; l is1And L2Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene; ar (Ar)1And Ar2Each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C60 heteroaryl; when the above groups have substituents, the substituents are respectively and independently selected from one or more of halogen, C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, monocyclic aryl or fused ring aryl of C6-C30, monocyclic heteroaryl or fused ring heteroaryl of C3-C60.
The specific reason why the compound of the present invention is excellent as an electron transport layer material in an organic electroluminescent device is not clear, and the following reasons are presumed: the compound parent nucleus of the general formula is formed by mutually merging benzene or an N-hetero six-membered ring and two N-hetero five-membered rings, has good electron deficiency, and is favorable for injecting electrons; and, Ar is an aryl or heteroaryl group attached to a specified position of the parent nucleus1And Ar2The conjugated system of the parent nucleus is further expanded, and the compound of the general formula also has a good planar structure, so that the electron transfer capability is improved, the electron transfer rate of the whole newly-constructed molecule is improved, and the excellent effects of high luminous efficiency and low starting voltage of the device are ensured. Especially when Ar is1And Ar2When the electron-withdrawing group is added, the electron-injecting ability can be further improved. In addition, when Ar is1And Ar2When a substituent is present, the substituents are preferably independently selected from C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, monocyclic aryl or fused ring of C6-C30Aryl, monocyclic heteroaryl of C3-C60, or fused ring heteroaryl.
In the present specification, the expression of Ca to Cb represents that the group has carbon atoms a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified. In the present invention, the expression of chemical elements includes the concept of chemically identical isotopes, such as the expression of "hydrogen", and also includes the concept of chemically identical "deuterium" and "tritium".
In the present specification, examples of the C6-C30 aryl group include: phenyl, biphenyl, naphthyl, anthryl, phenanthryl, fluorenyl and the like, with phenyl and naphthyl being preferred, and phenyl being more preferred;
the heteroatom in the present invention generally refers to an atom or group of atoms selected from B, N, O, S, P, P (═ O), Si and Se, preferably selected from N, O, S.
In the present specification, examples of the heteroaryl group having from C3 to C60 include: nitrogen-containing heteroaryl, oxygen-containing heteroaryl, sulfur-containing heteroaryl, and the like, and specific examples thereof include: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, indolyl, benzimidazolyl, indazolyl, imidazopyridinyl, benzotriazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, benzisoxazolyl, benzisothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzofuranyl, dibenzothienyl, piperidyl, pyrrolidinyl, piperazinyl, morpholinyl, phenazinyl, phenothiazinyl, phenoxazinyl, and the like are preferred among them, pyridyl, dibenzofuranyl, piperidyl, pyrrolidinyl, piperazinyl, morpholinyl, phenazinyl, phenothiazinyl, phenoxazinyl, and the like, Dibenzothienyl radical.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, etc., preferably fluorine.
The compound of the present invention preferably has structures (a) to (e):
the above compound of the present invention is preferably R1～R5Each independently selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted pyrrolyl or substituted or unsubstituted pyridyl, R1～R4Hydrogen is preferred.
The above compound of the present invention is preferably L1And L2Each independently selected from a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group. L is1Or L2And more preferably biphenylene, so that the plane has a certain twisting angle, and the phenomenon that the efficiency of the device is influenced due to the fact that molecules are excessively accumulated to easily cause quenching is avoided.
The above compound of the present invention is preferably Ar1And Ar2Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted heterofluorenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, and substituted or unsubstituted heteroaquinonyl. More preferably Ar1And Ar2Each independently selected from substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl and substituted or unsubstituted triazinyl, so that the compound at least comprises two electron-deficient groups (including triaza fused aromatic ring), thereby being beneficial to regulating the energy level structure of molecules and improving the electron injection capability.
The above compound of the present invention is further preferably L1And L2When it is a single bond, Ar1And Ar2At least one has C6-C30 aryl substituent or C3-C60 heteroaryl substituent. Is beneficial to the expansion of molecular plane structure and can increase molecular weight, thereby improving the practicability and stability of the material.
The compounds of the present invention are preferably selected from the structures represented by C1 to C120 below, but these compounds are representative only:
the compound having the structure shown in (1) of the present invention has a high electron affinity, and therefore has a high electron-withdrawing ability, and is suitable for use as an electron transport material, and the application field is not limited to organic electroluminescent materials, and can be applied to the technical fields of large-area sensors such as optical sensors, solar cells, lighting devices, organic thin-film transistors, organic field-effect transistors, organic thin-film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners, and electronic paper.
The present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, characterized in that the organic layer contains the compound of the present invention.
Specifically, the invention provides an organic electroluminescent device, which comprises a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer which are sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; wherein the electron transport layer contains the compound of the general formula of the present invention represented by the above formula (1).
Effects of the invention
The compound of the invention has higher electron affinity, thus having stronger electron-withdrawing ability and being suitable for being used as an electron transport material. As the benzene or N-heterocyclic six-membered ring and N-heterocyclic five-membered ring are mutually fused, compared with the common structures of single oxazole, thiazole, imidazole, triazole or triazine in the prior art, the structure of the compound has good electron deficiency, thereby being beneficial to the injection of electrons, and simultaneously having relatively better planar structure, improving the electron mobility and further being beneficial to improving the electron mobility of the whole newly-constructed molecule. Therefore, when the compound is used as an electron transport layer material in an organic electroluminescent device, the electron injection and migration efficiency in the device can be effectively improved, so that the excellent effects of high luminous efficiency and low starting voltage of the device are ensured.
Detailed Description
In order to make those skilled in the art better understand the present invention, the following will describe the specific preparation method of the above compound of the present invention by taking several synthetic examples as examples, but the preparation method of the present invention is not limited to these several synthetic examples, and those skilled in the art can make any modification, equivalent substitution, improvement, etc. without departing from the principle of the present invention, and extend the method to the scope of the technical scheme of the present invention as claimed in the claims.
Compounds of synthetic methods not mentioned in the present invention are all starting products obtained commercially. Solvents and reagents used in the present invention, such as petroleum ether, ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, dichloromethane, acetic acid, potassium carbonate, and the like, are commercially available from Shanghai Tantake technology, Inc. and Xiong chemical, Inc., and some of the intermediates are custom-synthesized and purchased by pharmaceutical intermediate manufacturers. In addition, they can be synthesized by a known method by those skilled in the art.
The method for synthesizing the organic compound of the present invention will be briefly described below by way of specific synthetic examples. The mass spectrometer used for determining the following compounds was a ZAB-HS type mass spectrometer measurement (manufactured by Micromass, UK).
Synthetic examples
Synthesis example 1: synthesis of Compound C1
Preparation of Compound 1-1
2-aminopyridine (9.4g, 100mmol) was dissolved in 100mL of methanol, and 10g of HClO was added4Then, 3-phenylpropionaldehyde (13.3g, 100mmol) was added dropwise thereto, and after the addition, 3-cyanopyridine (10.3g, 100mmol) was further added thereto under stirring at room temperature for 2 hours, followed by reaction at room temperature for 4 hours, and TLC showed completion of the reaction. Concentrating methanol, adjusting pH of the system to neutral with sodium carbonate solution, extracting with DCM, collecting and spin drying to obtain crude product, and separating by silica gel column chromatography to obtain compound 1-1(20.15g, 65%).
Preparation of Compounds 1-2
Compound 1-1(20.15g, 65mmol) was dissolved in 200mL of dichloromethane, and iodine (33g, 130mmol) was added thereto, followed by stirring at room temperature overnight. TLC monitored the end of the reaction. The solvent was concentrated, and then an appropriate amount of ethanol was added thereto, followed by washing with stirring and filtration to obtain compound 1-2(19.83g, yield 70%).
Preparation of Compound C1
Compound 1-2(19.83g, 45.5mmol), 2- (4-pinacolato) phenyl-4, 6-diphenyl-1, 3, 5-triazine (23.8g, 54.6mmol) and potassium carbonate (18.83g, 136.5mmol) were charged into a flask containing tetrahydrofuran: water (200 mL: 40mL), nitrogen was replaced with stirring at room temperature, and Pd (dpp) was added2Cl2(0.99g, 1.36 mmol). After the addition was complete, the reaction was heated to reflux under nitrogen with stirring for 8 hours and TLC showed completion of the reaction. For treatingThe white solid that separated out was filtered. The resulting solution was dissolved in 2L of toluene under reflux, subjected to column chromatography under reduced pressure and filtered, and the filtrate was collected and concentrated to obtain Compound C1(14g, yield 50%) as a white solid. Calculated molecular weight: 617.23, found C/Z: 617.1.
synthesis example 2: synthesis of Compound C7
Preparation of Compound 2-1
2-bromo-9, 10-diphenyl-anthracene (40.8g, 100mmol), pinacol diboron (38.1g, 150mmol), potassium acetate (29.4g, 300mmol), Pd (dppf)2Cl2(2.19g, 3mmol) was added to a flask containing 500mL of 1, 4-dioxane, the reaction was heated to reflux under nitrogen for 4 hours and TLC indicated completion of the reaction. Cooling to room temperature, concentrating the solvent, washing with water and filtering to obtain a solid, and then washing with ethanol to obtain compound 2-1(41g, 90%).
Preparation of Compound C7
Compound 1-2(21.8g, 50mmol), compound 2-1(22.8g, 50mmol) and potassium carbonate (20.7g, 150mmol) which were synthesized repeatedly in accordance with the procedure in Synthesis example 1 were charged into a flask containing tetrahydrofuran: water (200 mL: 40mL), nitrogen gas was replaced under stirring at room temperature, and Pd (dpp) was added2Cl2(1.09g, 1.5 mmol). After the addition was complete, the reaction was heated to reflux under nitrogen with stirring for 8 hours and TLC showed completion of the reaction. The precipitated pale yellow solid was filtered. Dissolving with dichloromethane, drying over anhydrous sodium sulfate, column chromatography (eluent dichloromethane) gave compound C7 as a pale yellow solid (18.7g, 59% yield). Calculated molecular weight: 638.25, found C/Z: 638.3.
synthesis example 3: synthesis of Compound C12
Synthesized by a synthesis method similar to that of C1. Except that the first step 3-1 synthesis was performed using aniline instead of 2-amino-pyridine and the last step 2- (3-pinacol ester group) phenyl-4, 6-diphenyl-1, 3, 5-triazine instead of 2- (4-pinacol ester group) phenyl-4, 6-diphenyl-1, 3, 5-triazine; a white solid compound C12 was obtained by a similar synthetic method, calculated as molecular weight: 615.24, found C/Z: 615.2.
synthesis example 4: synthesis of Compound C15
The preparation method comprises the steps of custom-synthesizing 4-1 and 4-2 by a pharmaceutical intermediate manufacturer, taking 4-1(13.4g, 50mmol) and 4-2(25.5g, 50mmol), potassium carbonate (20.7g, 150mmol), Pd (dba)2)3(1.3g, 1.5mmol), S-phos (1.23g, 3mmol) was added to a three-necked flask containing 1, 4-dioxane: water (200 mL: 20mL) and the reaction was refluxed overnight under nitrogen. After the TLC detection, a large amount of white solid is separated out. The solid was filtered, heated and dissolved in 2L of toluene, and then subjected to column chromatography under reduced pressure, collected and concentrated to obtain compound C15(20.29g, yield 66%), calculated as molecular weight: 615.24, found C/Z: 615.2.
synthesis example 5: synthesis of Compound C20
The preparation method comprises the steps of custom-synthesizing 5-1 and 5-2 by a pharmaceutical intermediate manufacturer, taking 5-1(13.5g, 50mmol) and 5-2(25.6g, 50mmol), potassium carbonate (20.6g, 150mmol), Pd (dba)2)3(1.3g, 1.5mmol), S-phos (1.24g, 3mmol) was added to a three-necked flask containing 1, 4-dioxane: water (200 mL: 20mL) and the reaction was refluxed overnight under nitrogen. After the TLC detection, a large amount of white solid is separated out. The solid was filtered, heated and dissolved in 1L of toluene, and then subjected to column chromatography under reduced pressure, followed by collection and concentration to obtain compound C20(21.87g, yield 71%), calculated as molecular weight: 616.24, found C/Z: 616.2.
synthesis example 6: synthesis of Compound C45
Synthesis of Compound 6-1
2- (4-bromo) phenyl-4, 6-diphenyl-1, 3, 5-triazine (38.7g, 100mmol), p-chlorobenzeneboronic acid (18.72, 120mmol), potassium carbonate (41.4g, 300mmol), Pd (PPh)3)4(1.15g, 1mmol) was added to a flask containing 400mL of toluene, 40mL of ethanol, and 40mL of water, and the reaction was heated under reflux for 4 hours under nitrogen atmosphere, and TLC showed completion of the reaction. After cooling to room temperature, a solid precipitated, which was filtered and washed with water, then rinsed with ethanol and dried to give compound 6-1(37.7g, 90%).
Synthesis of Compound 6-2
Mixing 6-1(37.7g, 90mmol), pinacol ester diboron (34.29g, 135mmol), potassium acetate (26.46g, 270mmol), Pd (OAc)2(0.6g, 2.7mmol), Sphos (2.22g, 5.4mmol) were added to a flask containing 400mL1, 4-dioxane, the reaction was heated to reflux under nitrogen for 4 hours and TLC indicated completion of the reaction. Cooled to room temperature, extracted with DCM, concentrated, washed with ethanol, filtered and dried to give compound 6-2(36.8g, 80%).
Synthesis of Compound C45
Preparing and synthesizing 6-3 by a pharmaceutical intermediate manufacturer, taking 6-3(13.4g, 50mmol) and 6-2(25.6g, 50mmol) obtained in the previous step, potassium carbonate (20.7g, 150mmol), Pd (dba)2)3(1.3g, 1.5mmol), S-phos (1.24g, 3mmol) was added to a three-necked flask containing 1, 4-dioxane: water (200 mL: 20mL) and the reaction was refluxed overnight under nitrogen. After the TLC detection, a large amount of white solid is separated out. The solid was filtered, heated and dissolved in 1.5L of toluene, and then subjected to column chromatography under reduced pressure, followed by collection and concentration to obtain compound C45(20.97g, yield 68%), calculated as molecular weight: 617.23, found C/Z: 617.2.
synthesis example 7: synthesis of Compound C105
The 7-1 and 7-2 are custom-synthesized by a pharmaceutical intermediate manufacturer, and 7-1(17.9g, 50mmol) and 7-2(20.95g, 50mmol), cesium carbonate (48.9g, 150mmol), CuI (4.7g, 25mmol), 1, 10-phenanthroline (4.5g, 25mol) are added into a three-neck flask containing 300mLDMF, and the reaction is refluxed overnight under the protection of nitrogen. The TLC detection shows that the reaction is finished. Cooling to room temperature, concentrating the solvent, washing with water, filtering, washing with ethanol, drying, dissolving a large amount of dichloromethane, performing column chromatography, collecting and concentrating to obtain a compound C105(20.19g, yield 63%), calculating molecular weight: 641.23, found C/Z: 641.2.
synthesis example 8: synthesis of Compound C102
The 8-1 is custom-made and synthesized by a pharmaceutical intermediate manufacturer, and 8-2 is obtained by purchase. Taking 8-1(15.4g, 50mmol), 8-2(19.35g, 50mmol), sodium tert-butoxide (14.41g, 150mmol), Pd2(dba)3(0.46g, 5mmol), tri-tert-butylphosphine (0.20g, 10mol) was added to a three-necked flask containing 150mL of xylene and the reaction refluxed overnight under nitrogen. The TLC detection shows that the reaction is finished. Cooling to room temperature, concentrating the solvent, washing with water, filtering, washing with ethanol, drying to obtain a solid, dissolving the solid with a large amount of dichloromethane, performing column chromatography, collecting and concentrating to obtain a compound C102(17.24g, yield 56%), calculated on molecular weight: 616.24, found C/Z: 616.2.
device embodiments
The present invention also provides an organic electroluminescent device comprising the compound of the above embodiment. An example of using an OLED as an embodiment of the organic electronic light emitting device is illustrated below. The OLED of the present embodiment includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-34; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI1-HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1-HI3 described below.
The light emitting layer includes a light emitting dye (i.e., Dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but is not limited to, the combination of one or more of BFH-1 through BFH-16 listed below.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent dopant may be selected from, but is not limited to, combinations of one or more of BFD-1 through BFD-12 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light emitting layer is selected from, but not limited to, one or more of GPH-1 to GPH-80.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer can be selected from, but is not limited to, one or more of GPD-1 to GPD-47 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but is not limited to, one or more of YPD-1 to YPD-11 listed below.
The organic EL light-emitting device of the present invention further includes an electron transport region between the light-emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
The electron transport region may also be formed using the compound of the present invention for a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL), although the material of the electron transport region may also be combined with one or more of ET-1 to ET-57 listed below.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, combinations of one or more of the following: LiQ, LiF, NaCl, CsF, Li2O、Cs2CO3BaO, Na, Li and/or Ca.
The technical effects and advantages of the present invention are demonstrated and verified by testing practical use performance by specifically applying the compound of the present invention to an organic electroluminescent device.
Example 1
The preparation process of the organic electroluminescent device of the embodiment is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing until the pressure is less than 10-5Pa, regulating the evaporation rate of a hole transport material HT-4 to be 0.1nm/s, setting the evaporation rate of a hole injection material HI-3 to be 7% in proportion, and setting the total thickness of the evaporation film to be 10nm by using a multi-source co-evaporation method on the anode layer film;
evaporating HT-4 on the hole injection layer in vacuum to serve as a first hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 80 nm;
evaporating HT-14 on the first hole transport layer in vacuum to serve as a second hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 10 nm;
a luminescent layer of the device is vacuum evaporated on the second hole transport layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material BFH-4 is adjusted to be 0.1nm/s, the evaporation rate of the dye BFD-4 is set in a proportion of 5%, and the total film thickness of evaporation is 20nm by using a multi-source co-evaporation method;
vacuum evaporating ET-17 on the luminescent layer to be used as a hole blocking layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 5 nm;
on the hole blocking layer, the evaporation rate of the C1 compound of the electron transport material is adjusted to be 0.1nm/s by a multi-source co-evaporation method, the evaporation rate is set to be 100% of the evaporation rate of ET-57, and the total film thickness of evaporation is 23 nm;
LiF with the thickness of 1nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 80nm is used as a cathode of the device.
Examples 2 to 8 and comparative examples 1 to 2
The processes of examples 2 to 8 and comparative examples 1 to 2 were the same as in example 1 except that the electron transporting material C1 was replaced with C7, C12, C15, C20, C45, C105, C102 and the compounds ET-6 and ET-42, respectively.
Wherein, the structural formula of the comparative compound used in comparative examples 1-2 is shown below:
the organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples 1 to 8 and comparative examples 1 to 2 and the lifetime of the devices were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 1000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the luminance to the current density is the current efficiency. The results are shown in Table 1.
TABLE 1
In the case of examples 1 to 8 and comparative examples 1 and 2, in the case where the organic electroluminescent device structure is the same as the other materials, the voltage of the compound in the example of the present invention is lower than that of the electron transport material ET-42 in comparative example 1 and the efficiency is greatly improved as compared with that of the electron transport material ET-6 in comparative example 1. The reason is presumably that the radical structure of the triaza fused aromatic ring contained in the compound of the invention has strong electron-withdrawing capability and is beneficial to the injection of electrons. The compounds in examples 1-8 contain at least 2 electron-deficient groups (such as triaza fused aromatic ring, pyridine, pyrimidine, cyano, triazine and the like), and compared with the electron transport materials ET-42 and ET-6 containing only one electron-deficient group, the electron injection capability is remarkably improved.
Further, the compound of the present invention is at a specific position of the triaza fused aromatic ring (specifically, X of the formula (1))6And/or X7) The upper extension connection conjugated group can improve the molecular weight on one hand, so that the Tg and the evaporation temperature meet the requirements of devices, and on the other hand, the upper extension connection conjugated group also has good plane conjugation, and the structural group of the triaza fused aromatic ring has a larger structural plane, thereby being beneficial to the transmission of electrons. In the structures of the compounds in examples 5, 6 and 7, the triazine structure is bridged by biphenyl to form a parent nucleus containing triaza fused aromatic ring, so that the planarity of the triazine structure is enhanced, and the triazine structure has better transmission performance compared with anthracene in ET-42, thereby improving the current efficiency. Compared with ET-6, the compound is connected with triazine through biphenyl meta-position, and compared with the compound directly connected with triazine through a spirofluorene structure, the plane has a certain torsion angle, so that the effect that molecules are stacked too much to cause quenching easily and influence the efficiency of a device can be avoided.
The applicants have also found that although the compound of example 8 has a lower driving voltage and a higher current efficiency than those of comparative examples 1 and 2, the driving voltage is slightly insufficient compared with those of examples 1 to 7, and the reason for this is not clear, and it is presumed that this is due to the presence of a triazine fused aromatic ringCorresponds to R1～R4Is linked to a conjugated group (i.e., R)1～R4One or more of them is a conjugated group such as phenyl), so that the compound represented by the formula (1) of the present invention is preferably R1～R4Is hydrogen.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (10)
1. A compound for an organic light-emitting material, characterized by having a structure shown in (1):
wherein R is1～R5Each independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C60 heteroaryl;
X1～X7each independently selected from C or N atoms, and the total number of N atoms is 3, wherein X6～X7At most one is an N atom;
L1and L2Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene;
Ar1and Ar2Each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C60 heteroaryl;
when the above groups have substituents, the substituents are respectively and independently selected from one or more of halogen, C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, monocyclic aryl or fused ring aryl of C6-C30, monocyclic heteroaryl or fused ring heteroaryl of C3-C60.
2. The compound of claim 1, having the structures (a) to (e):
3. a compound according to claim 1 or 2, wherein R is1～R5Each independently selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted pyrrolyl or substituted or unsubstituted pyridyl, R1～R4Hydrogen is preferred.
4. A compound according to claim 1 or 2, wherein L is1And L2Each independently selected from a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
5. The compound of claim 1 or 2, wherein Ar is Ar1And Ar2Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted heterofluorenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, and substituted or unsubstituted heteroaquinonyl.
6. A compound according to claim 1 or 2, wherein L is1And L2When it is a single bond, Ar1And Ar2At least one has C6-C30 aryl substituent or C3-C60 heteroaryl substituent.
7. The compound of claim 1, wherein said compound has a structure as shown in C1-C120:
8. use of a compound having a structure represented by (1) as an electron transport material in an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet type scanner or electronic paper,
wherein R is1～R5Each independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C60 heteroaryl;
X1～X7each independently selected from C or N atoms, and the total number of N atoms is 3, wherein X6～X7At most one is an N atom;
L1and L2Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 a heteroarylene group;
Ar1and Ar2Each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C60 heteroaryl;
when the above groups have substituents, the substituents are respectively and independently selected from one or more of halogen, C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, monocyclic aryl or fused ring aryl of C6-C30, monocyclic heteroaryl or fused ring heteroaryl of C3-C60.
9. An organic electroluminescent element comprising a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, wherein the compound according to any one of claims 1 to 7 is contained in the organic layer.
10. An organic electroluminescent device comprising an anode layer, a plurality of light emitting functional layers and a cathode layer; the plurality of light-emitting functional layers sequentially comprise a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, and the cathode layer is formed on the electron transport layer; wherein the electron transport layer contains the compound according to any one of claims 1 to 7.
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