CN111377914A - Compound, application thereof and organic electroluminescent device comprising compound - Google Patents
Compound, application thereof and organic electroluminescent device comprising compound Download PDFInfo
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- CN111377914A CN111377914A CN201811621012.0A CN201811621012A CN111377914A CN 111377914 A CN111377914 A CN 111377914A CN 201811621012 A CN201811621012 A CN 201811621012A CN 111377914 A CN111377914 A CN 111377914A
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Abstract
The invention provides a compound, application thereof and an organic electroluminescent device comprising the compound, wherein the compound has a structure shown in a formula (I), E is selected from one of substituted or unsubstituted C3-C30 heteroaryl, D has a structure shown in a formula (II), and L1And L2Each independently selected from one of single bond, substituted or unsubstituted C6-C30 arylene and substituted or unsubstituted C3-C30 heteroarylene, the compound is used as an electron transport material in an organic electroluminescent device, and the electron transport material has stronger electron transport capability and lower injection energy barrier, and can effectively reduce the driving voltage of the organic electroluminescent device, improve the luminous efficiency and reduce the efficiency roll-off.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound, application thereof and an organic electroluminescent device comprising the compound.
Background
The famous chinese scientist dunqing cloud professor reported in 1987 for the first time that the electroluminescent phenomenon based on tris (8-hydroxyquinoline) aluminum (Alq3) opened the hot tide of organic electroluminescent diode (OLEDs) research. OLEDs have many advantages such as self-luminescence, high contrast, low power consumption, etc., and thus have attracted extensive attention in the chemical and industrial fields.
Common organic electroluminescent devices have a typical sandwich structure and are often composed of a plurality of functional layers such as a hole transport layer, a light emitting layer, an electron transport layer and the like. In the organic electroluminescent device, the higher exciton injection energy barrier tends to result in high voltage, and the injection energy barrier of the current electron transport material is still to be further improved. In addition, the carrier mobility of the existing electron transport material is often lower than that of the hole transport material, so that the phenomenon of unstable electroluminescence spectrum, serious efficiency roll-off and the like caused by deviation of an exciton recombination region is caused.
CN108822114A discloses an OLED electron transport material and application thereof, the material takes electron-deficient 2, 7-diphenyl-1, 3,6, 8-tetraazapyrene as a core, and proper substituent groups are introduced into the electron-deficient center to form a micromolecule OLED functional layer material with excellent electron transport performance, the molecular weight is 510-820, the material has a closed-loop structure and excellent thermal stability, and can be suitable for an evaporation process for manufacturing micromolecule organic electroluminescent devices, but the electron transport capacity and the electron injection capacity of the material need to be further optimized.
CN108409730A discloses an organic small molecule electron transport material and a preparation method thereof. The preparation method of the organic micromolecule electron transport material comprises the following steps: (1) carrying out coupling reaction on 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 3-bromo-phenylboronic acid, and carrying out subsequent treatment to obtain a bromine-containing intermediate; (2) carrying out Suzuki reaction on the bromine-containing intermediate and diboron pinacol ester, and carrying out subsequent treatment to obtain a borate intermediate; (3) and (3) carrying out coupling reaction on the borate intermediate and 3-bromo-1, 10-phenanthroline, and carrying out subsequent treatment to obtain the organic micromolecule electron transport material. The organic micromolecule electron transport material has a simple structure and good thermal stability and morphology stability; an n-doped electron transport layer formed by n-doping is used for an organic electroluminescent device and has high luminous efficiency and high stability, but the electron transport capability and the electron injection capability of the organic electroluminescent device are required to be further optimized.
CN108475735A discloses an organic electron transport material comprising a phosphine oxide derivative substituted with one or both of aryl and heteroaryl groups, and optionally having one or more atomic groups of phosphine oxide groups, and further substituted with atoms or atomic groups of hydrogen atoms, halogen atoms, cyano groups, nitro groups, carboxyl groups, formyl groups, carbonyl groups, alkoxycarbonyl groups, and trifluoromethyl groups, which is a novel organic electron transport material having excellent stability and durability due to high chemical stability of C — P bond in an anionic state, but its electron transport ability and electron injection ability are still to be further optimized.
Therefore, there is a need in the art to develop a compound having a relatively strong electron transport ability and a relatively low injection energy barrier, so that when the compound is applied to an electron transport material in an organic electroluminescent device, the compound can further reduce the driving voltage, improve the luminous efficiency, and reduce the efficiency roll-off.
Disclosure of Invention
The invention aims to provide a compound, which has the structure of formula (I),
in the formula (I), R is1、R2、R3And R4Each independently selected from one of hydrogen, C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
in the formula (I), E is selected from one of substituted or unsubstituted C3-C30 heteroaryl;
in the formula (I), D has a structure shown in a formula (II),
wherein the dotted line represents an access position connected with other groups, the dotted line or the solid line is led out from the middle of the benzene ring, and represents that a substituent can be substituted at any substitutable position of the benzene ring, and the following relates to similar representation methods and has the same meaning;
in the formula (II), R is5Represents a mono-to maximum permissible substituent, said R5Each independently selected from one of hydrogen, C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, or the R5And the aromatic rings connected with the aromatic ring are condensed to form one of substituted or unsubstituted C10-C30 aryl and substituted or unsubstituted C9-C30 heteroaryl;
if condensation is carried out, R5One selected from substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
the maximum permissible substituent means that the number of the substituent is the maximum number of substitutions provided that the substituted group satisfies the chemical bond requirement, and illustratively, when the structure of the formula (II) is a phenylene group, R is5It may be one or more, but up to the maximum permissible substituents (i.e. 4) for the phenylene group. The same meanings apply hereinafter to the same descriptions (monosubstituted to the maximum permissible substituents);
the R is5And the aromatic rings to which they are attached are fused to each other means: the R is5The group may be one or more, and the one or more R5Between radicals, and optionally one or more R5Radicals and radicals with said one or more R5The aromatic rings connected with the groups can be arbitrarily fused to form a ring, and can be a plurality of adjacent R5The radicals condensed to one another may also be R5The group is fused to the attached aromatic ring to form a ring, and the present invention is not limited to the specific fusion mode, and the following description refers toThe same description has the same meaning;
in the formula (I), L is1And L2Each independently selected from a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
the substituted substituent groups are respectively and independently selected from one of halogen, cyano, C1-C10 alkyl, C1-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 cycloalkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 monocyclic aryl, C6-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C3-C30 fused ring heteroaryl.
The invention aims to provide a compound with electron transport performance, which selects a pyrido triazole group as a parent nucleus of the compound, and the parent nucleus has good electron deficiency and conjugation, so that the mobility of carriers is improved, higher electron transport capacity and lower charge injection energy barrier are obtained, and the aims of effectively reducing driving voltage, improving luminous efficiency and reducing efficiency roll-off when the compound is applied to an organic electroluminescent device are fulfilled.
Preferably, said L1And L2Each independently selected from a single bond or a structure having formula (L-1),
in the formula (L-1), p and q are independently selected from 0 or 1 and are not simultaneously 0, and in the formula (L-1), F and G are independently selected from any one of the following substituted or unsubstituted S1-S7 groups:
wherein the dotted line crosses two or three rings, and represents that the substituent may be substituted at any substitutable position of the two or three rings, and the same meanings apply hereinafter, if the same notations appear;
the substituted substituent groups are respectively and independently selected from one of halogen, cyano, C1-C10 alkyl, C1-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 cycloalkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 monocyclic aryl, C6-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C3-C30 fused ring heteroaryl.
Preferably, F and G are each independently selected from one of the following substituted or unsubstituted groups:
preferably, said E has the structure of formula (III),
said X1、X2、X3、X4、X5Each independently selected from nitrogen atom or CR7And said X1、X2、X3、X4、X5At least one of them is a nitrogen atom;
the R is7Each independently selected from one of hydrogen, C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, or the R7And the aromatic rings connected with the aromatic ring are condensed to form one of substituted or unsubstituted C9-C30 heteroaryl;
if condensed, the R7One selected from substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
the substituted substituent groups are respectively and independently selected from one of halogen, cyano, C1-C10 alkyl, C1-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 cycloalkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 monocyclic aryl, C6-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C3-C30 fused ring heteroaryl.
In order to improve the electron transport performance of the compound, an electron-withdrawing substituent E containing nitrogen atoms is introduced into the compound, so that the electron-withdrawing substituent E plays a synergistic role with a pyridine triazole parent nucleus, and the intramolecular and intermolecular forces are enriched, thereby further improving the electron transport performance of the compound, reducing the electron injection energy barrier, improving the luminous efficiency of a device, and reducing the driving voltage and the efficiency roll-off.
Preferably, D has a structure of formula (2-1) or formula (2-2),
the R is5Represents a mono-to maximum permissible substituent, said R5Each independently selected from one of hydrogen, C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, or the R5And the aromatic rings connected with the aromatic ring are condensed to form one of substituted or unsubstituted C10-C30 aryl and substituted or unsubstituted C9-C30 heteroaryl;
if condensed, the R5One selected from substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl.
Preferably, said R is5Each independently selected from one of pyridyl, phenanthryl and triphenylene.
Preferably, D is selected from phenylene or one of the following groups:
the A, B, C is respectively and independently selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, preferably one of substituted or unsubstituted C6-C12 aryl and substituted or unsubstituted C3-C12 heteroaryl;
the R is5Represents a mono-to maximum permissible substituent, said R5Each independently selected from one of hydrogen, C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, or the R5And the aromatic rings connected with the aromatic ring are condensed to form one of substituted or unsubstituted C10-C30 aryl and substituted or unsubstituted C9-C30 heteroaryl;
if condensed, the R5One selected from substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
the substituted substituent groups are respectively and independently selected from one of halogen, cyano, C1-C10 alkyl, C1-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 cycloalkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 monocyclic aryl, C6-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C3-C30 condensed ring heteroaryl.
Preferably, D is selected from one of the following substituted or unsubstituted groups:
preferably, E is selected from one of the following groups:
z is1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、Z9、Z10、Z11、Z12、Z13Each independently selected from nitrogen atom or CR7；
The R is7Each independently selected from one of hydrogen, C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, or the R7And the aromatic rings connected with the aromatic ring are condensed to form one of substituted or unsubstituted C10-C30 aryl and substituted or unsubstituted C9-C30 heteroaryl;
if condensed, the R7One selected from substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
the substituted substituent is independently selected from one of halogen, cyano, C1-C10 alkyl, C1-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 cycloalkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 monocyclic aryl, C6-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C3-C30 fused ring heteroaryl;
z is1、Z2、Z3、Z4、Z5At least one of which is a nitrogen atom;
z is6、Z7、Z8、Z9、Z10、Z11、Z12、Z13At least one of which is a nitrogen atom.
In order to improve the electron transmission performance of the compound, the groups E have better electron-withdrawing ability of the formulas (3-1) and (3-2), have more obvious synergistic effect with a pyridine triazole parent nucleus, and the prepared organic electroluminescent device has higher luminous efficiency and lower driving voltage and efficiency roll-off.
Preferably, the E is selected from one of substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted quinoline, substituted or unsubstituted triazine, substituted or unsubstituted quinoxaline and substituted or unsubstituted quinazoline;
the substituted substituent groups are respectively and independently selected from one of halogen, cyano, C1-C10 alkyl, C1-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 cycloalkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 monocyclic aryl, C6-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C3-C30 condensed ring heteroaryl.
Preferably, the compound is selected from one of the following compounds:
the second purpose of the invention is to provide the application of the compound in the first purpose, wherein the application is used as an electron transport material in an organic electroluminescent device.
It is a further object of the present invention to provide an organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between said first and second electrodes, said organic layers comprising at least one compound according to one of the objects.
The organic electroluminescent device 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.
A substrate may be used under the first electrode or over 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, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used. 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 polyphenylenevinylenes, 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 the 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 to 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 organic electroluminescent 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.
When the luminescent layer adopts the technology of phosphorescence electroluminescence, the host material of the luminescent layer is selected from, but not limited to, one or more of GPH-1 to GPH-80.
When the light-emitting layer adopts the phosphorescent electroluminescence technology, the phosphorescent dopant of the light-emitting layer can be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
When the luminescent layer adopts the technology of thermal activation delayed fluorescence luminescence, the luminescent layer fluorescence dopant can be selected from, but is not limited to, one or more combinations of TDE-1 to TDE-39 listed below.
The organic material layer may further include 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 layer material may be selected from, but is not limited to, combinations of one or more of ET-1 through 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 materials including, but not limited to, combinations of one or more of the following.
LiQ、LiF、NaCl、CsF、Li2O、Cs2CO3、BaO、Na、Li、Ca。
The electron transport functional layer of the present invention should also comprise the following compounds:
compared with the prior art, the invention has the following beneficial effects:
(1) the pyrido-triazole group is selected as the parent nucleus of the compound, and the parent nucleus has good conjugation and high carrier mobility, so that higher electron transport capacity and lower charge injection energy barrier are obtained, when the pyrido-triazole group is applied to an organic electroluminescent device, the driving voltage can be effectively reduced, the luminous efficiency is improved, the efficiency roll-off is reduced, and the maximum brightness is 46000cd/m2The starting voltage is 3.1V or below, and the maximum external quantum efficiency is more than 18%.
(2) In the preferred technical scheme, an electron-deficient substituent E containing nitrogen atoms is introduced to have a synergistic effect with a pyridine triazole parent nucleus, so that intramolecular and intermolecular acting force can be enriched, the electron transport capacity of the compound can be further improved, the electron injection energy barrier can be reduced, and when the compound is used for an organic electroluminescent device, the device has higher luminous efficiency, lower driving voltage and efficiency roll-off.
(3) In a further preferred scheme, substituents with stronger electron-withdrawing ability of pyridine, pyrimidine, triazine and quinoline are selected to act with a pyridyltriazole parent nucleus synergistically, so that intramolecular and intermolecular acting force can be further enriched, the electron transport capacity of the compound can be further improved, the electron injection energy barrier can be further reduced, and when the compound is used for an organic electroluminescent device, the organic electroluminescent device with higher luminous efficiency, lower driving voltage and efficiency roll-off can be obtained.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
A representative synthetic route for compounds of general formula (la) is as follows:
preparation example 1
The synthesis procedure of M1 is as follows:
(1) synthesis of intermediate M1-2
10.9g (100mmol) of 2-hydrazinopyridine is added into 100mL of absolute ethyl alcohol, after heating and refluxing, 100mL of absolute ethyl alcohol solution dissolved with 19.4g (105mmol) of p-bromobenzaldehyde is added dropwise, after about 20min, the dropwise addition is finished, and then the stirring and the refluxing are continued for 1 h. After the reaction is finished, the temperature is reduced to room temperature, the mixture is stirred for 30min in an ice water bath, and then the mixture is filtered and drained. The resulting solid sample (M73-1) was dissolved in 100mL of dichloromethane, and 43.0g of [ bis (trifluoroacetoxy) iodo ] benzene (BTA, 100mmol) was added and stirred at room temperature for 1 h. After 150mL of methylene chloride was added to the reaction system, the reaction system was washed with a 10% sodium hydrogen sulfite solution (400mL), a 10% sodium carbonate solution (400mL) and a large amount of water in this order. The organic phase was concentrated and recrystallized from absolute ethanol to yield a large amount of off-white solid, 21.9g, 80.1% yield.
The mass of the molecular ions determined by mass spectrometry was: 273.01 (calculated value: 272.99); theoretical element content (%) C12H8BrN3: c, 52.58; h, 2.94; br, 29.15; n, 15.33. Measured elemental content (%): c, 52.53; h, 2.95; n, 15.31.
The above analysis results show that the obtained product is the expected product.
(2) Synthesis of intermediate M1-3
A dry 1000mL three-necked flask is taken, 3.5g (10mmol) of the M1-2 intermediate obtained in the first step, 5.1g (20mmol) of pinacol diboron diboride and 1.46g (2mmol) of 1,1' -bis (diphenylphosphine) ferrocene palladium dichloride are sequentially added under the nitrogen condition, and finally 500mL of dry 1, 4-dioxane is added, and heating reflux reaction is carried out for 15 h. After the completion of the reaction, the solvent in the reaction system was removed by distillation under reduced pressure. Extraction with dichloromethane, washing with a large amount of water, combining organic phases and performing column chromatography. Column chromatography with dichloromethane to petroleum ether 1:2 as eluent gave a large amount of white solid, 4.5g, 86.5% yield.
The mass of the molecular ions determined by mass spectrometry was: 396.21 (calculated value: 396.20); theoretical element content (%) C18H20BN3O2: c, 67.31; h, 6.28; b, 3.37; n, 13.08; and O, 9.96. Measured elemental content (%): c, 67.29; h, 6.36; and N, 13.06.
The above analysis results show that the obtained product is the expected product.
(3) Synthesis of Compound M1
A dry 500mL two-necked flask was taken and charged with 2.6g (8.1mmol) of M1-3, 2.67g (10mmol) of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, 1.38g (10mmol) of anhydrous potassium carbonate and 230mg (2mmol) of palladium tetrakistriphenylphosphine in that order. After nitrogen substitution was carried out three times, 5mL of water, 5mL of ethanol and 300mL of toluene were added, and the mixture was refluxed for 12 hours. The solvent of the reaction system was distilled under reduced pressure, extracted with dichloromethane, and washed with a large amount of water. The organic phases were combined, concentrated and subjected to column chromatography using dichloromethane and petroleum ether at a ratio of 4:1 as eluent to give a white solid, 3.2g, 88.9% yield.
The mass of the molecular ions determined by mass spectrometry was: 426.19 (calculated value: 426.16); theoretical element content (%) C27H18N6: c, 76.04; h, 4.25; n, 19.71. Measured elemental content (%): c, 76.05; h, 4.22; n, 19.69.
The above analysis results show that the obtained product is the expected product.
Preparation example 2
The difference from preparation example 1 was that M-bromobenzaldehyde was replaced with p-bromobenzaldehyde in an equivalent amount to obtain compound M2 as a white solid (3.4 g, yield 94.5%)
The mass of the molecular ions determined by mass spectrometry was: 426.17 (calculated value: 426.16); theoretical element content (%) C27H18N6: c, 76.04; h, 4.25; n, 19.71. Measured elemental content (%): c, 76.03; h, 4.26; n, 19.68.
Preparation example 3
The difference from preparation example 1 was that 2-chloro-4, 6-diphenyl-1, 3, 5-triazine was replaced with an equivalent amount of 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine to give compound M4 as a white solid, 3.6g, in 71.7% yield.
The mass of the molecular ions determined by mass spectrometry was: 502.16 (calculated value: 502.19); theoretical element content (%) C33H22N6: c, 78.87; h, 4.41; n, 16.72. Measured elemental content (%): c, 73.85; h, 4.42; n, 16.73.
The above analysis results show that the obtained product is the expected product.
Example 1
The preparation process of the organic electroluminescent device comprises the following steps:
glass plates coated with indium tin oxide (ITO, thickness 150nm) transparent conductive layers were sonicated in 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 to 1 × 10-5～1×10-4Pa, performing vacuum evaporation on the anode layer film to obtain HI-2 and HT-2 which are respectively used as a hole injection layer and a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10nm and 40nm respectively;
vacuum evaporation of "GPH-77: TDE-7(30nm, 5% wt)' as the luminescent layer of the organic electroluminescent device, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm; wherein "5 wt%" means that the doping ratio of the dye, i.e., the weight ratio of the host material to TDE-7, is 95: 5.
Compound M1 is vacuum evaporated on the luminescent layer to be used as an electron transport layer of the organic electroluminescent device, the evaporation rate is 0.1nm/s, and the total thickness of the evaporation film is 25 nm;
and (3) evaporating LiF with the thickness of 0.5nm as an electron injection layer and Al with the thickness of 150nm as a cathode on the electron transport layer in vacuum.
The device structure is as follows:
ITO(150nm)/HI-2(10nm)/HT-2(40nm)/GPH-77：TDE-7(30nm,5％wt)/M1(25nm)/LiF(0.5nm)/Al(150nm)。
example 2
The difference from example 1 is that compound M1 was replaced by compound M2.
Example 3
The difference from example 1 is that compound M1 was replaced by compound M5.
Example 4
The difference from example 1 is that compound M1 was replaced by compound M10.
Example 5
The difference from example 1 is that compound M1 was replaced by compound M80.
Example 6
The difference from example 1 is that compound M1 was replaced by compound M89.
Example 7
The difference from embodiment 1 is that, by replacing TDE-7 with GPD-1, the device structure is as follows:
ITO(150nm)/HI-2(10nm)/HT-2(40nm)/GPH-77：GPD-1(30nm,5wt％)/M1(25nm)/LiF(0.5nm)/Al(150nm)。
example 8
The difference from example 7 is that compound M1 was replaced by compound M22.
Example 9
The difference from example 7 is that compound M1 was replaced by compound M65.
Example 10
The difference from example 7 is that compound M1 was replaced by compound M70.
Example 11
The difference from example 7 is that compound M1 was replaced by compound M84.
Example 12
The difference from example 7 is that compound M1 was replaced by compound M91.
Example 13
The difference from example 7 is that compound M1 was replaced by compound M44.
Example 14
The difference from example 7 is that compound M1 was replaced by compound M100.
Example 15
The difference from example 7 is that compound M1 was replaced by compound M33.
Comparative example 1
Differs from example 1 in that Compound M1 is replaced by Compound R-1
Comparative example 2
Differs from example 7 in that Compound M1 is replaced by Compound R-1
And (3) performance testing:
the organic electroluminescent devices prepared in examples and comparative examples were measured for turn-on voltage, maximum luminance and maximum external quantum efficiency 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 1cd/m2The voltage is the starting voltage, the current density at the moment is measured, and the maximum external quantum efficiency is calculated according to data such as spectrum and the like.
The results of the performance tests are shown in tables 1 and 2.
TABLE 1
| Maximum luminance/cd/m2 | Turn-on voltage/V | Maximum external quantum efficiency/%) | |
| Example 1 | 53562 | 2.9 | 21.2 |
| Example 2 | 50608 | 3.0 | 20.4 |
| Example 3 | 49694 | 2.9 | 19.7 |
| Example 4 | 46397 | 3.0 | 18.9 |
| Example 5 | 47734 | 3.1 | 18.6 |
| Example 6 | 49519 | 3.0 | 19.2 |
| Comparative example 1 | 40295 | 3.6 | 14.4 |
TABLE 2
| Maximum luminance/cd/m2 | Turn-on voltage/V | Maximum external quantum efficiency/%) | |
| Example 7 | 51482 | 3.0 | 20.3 |
| Example 8 | 51020 | 3.0 | 19.6 |
| Example 9 | 53500 | 3.1 | 21.2 |
| Example 10 | 52212 | 2.9 | 20.1 |
| Example 11 | 52297 | 3.0 | 18.4 |
| Example 12 | 52194 | 3.1 | 19.4 |
| Example 13 | 52500 | 3.0 | 20.5 |
| Example 14 | 51056 | 2.9 | 21.6 |
| Example 15 | 52205 | 3.0 | 20.6 |
| Comparative example 2 | 42648 | 3.7 | 13.1 |
It can be seen from tables 1 and 2 that, when the compound of the present invention is used as an electron transport material for Thermally Activated Delayed Fluorescence (TADF) and phosphorescent dyes, the turn-on voltage, the maximum brightness and the maximum external quantum efficiency are all improved compared to the comparative examples, and excellent device performance is shown, wherein, as can be seen from comparative examples 1 to 6, comparative example 1, examples 7 to 15 and comparative example 2, the introduction of the pyrido-triazole group plays a crucial role in improving the performance of the device, because the pyrido-triazole group is used as the parent nucleus of the electron transport material, the parent nucleus has good conjugation property and high carrier mobility, so as to obtain high electron transport capability and low charge injection energy barrier, and when the compound is applied to an organic electroluminescent device, the driving voltage can be effectively reduced, the light emitting efficiency can be improved, and the charge injection energy barrier can be effectively improved, The efficiency roll-off is reduced, and excellent device performance is embodied. And the conjugation degree of R-1 is larger, the triplet state energy level of the whole molecule is obviously reduced, and the diffusion energy of blocking the excitons of the light emitting layer is deteriorated, so that the turn-on voltage is increased and the efficiency is reduced.
The present invention is illustrated in detail by the examples described above, but the present invention is not limited to the details described above, i.e., it is not intended that the present invention be implemented by relying on the details described above. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. A compound having the structure of formula (I),
in the formula (I), R is1、R2、R3And R4Each independently selected from one of hydrogen, C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
in the formula (I), E is selected from one of substituted or unsubstituted C3-C30 heteroaryl;
in the formula (I), D has a structure shown in a formula (II),
in the formula (II), R is5Represents a mono-to maximum permissible substituent, said R5Each independently selected from one of hydrogen, C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, or the R5And the aromatic rings connected with the aromatic ring are condensed to form one of substituted or unsubstituted C10-C30 aryl and substituted or unsubstituted C9-C30 heteroaryl;
in the formula (I), L is1And L2Each independently selected from a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
the substituted substituent groups are respectively and independently selected from one of halogen, cyano, C1-C10 alkyl, C1-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 cycloalkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 monocyclic aryl, C6-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C3-C30 fused ring heteroaryl.
2. The compound of claim 1, wherein L is1And L2Each independently selected from a single bond or a structure having formula (L-1),
in the formula (L-1), p and q are independently selected from 0 or 1 and are not simultaneously 0, and F and G are independently selected from any one of the following substituted or unsubstituted S1-S7 groups:
preferably, F and G are each independently selected from one of the following substituted or unsubstituted groups:
the substituted substituent groups are respectively and independently selected from one of halogen, cyano, C1-C10 alkyl, C1-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 cycloalkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 monocyclic aryl, C6-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C3-C30 fused ring heteroaryl.
3. The compound of claim 1, wherein E has the structure of formula (III),
said X1、X2、X3、X4、X5Each independently selected from nitrogen atom or CR7And said X1、X2、X3、X4、X5At least one of them is a nitrogen atom;
the R is7Each independently selected from one of hydrogen, C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, or the R7And the aromatic rings connected with the aromatic ring are condensed to form one of substituted or unsubstituted C9-C30 heteroaryl;
the substituted substituent groups are respectively and independently selected from one of halogen, cyano, C1-C10 alkyl, C1-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 cycloalkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 monocyclic aryl, C6-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C3-C30 fused ring heteroaryl.
4. A compound according to claim 1 or 3, wherein D has the structure of formula (2-1) or formula (2-2),
the R is5Having the same limits as in claim 1.
5. A compound according to claim 1 or 3, wherein D is selected from phenylene or one of the following groups:
the A, B, C is respectively and independently selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, preferably one of substituted or unsubstituted C6-C12 aryl and substituted or unsubstituted C3-C12 heteroaryl;
the R is5Having the same limits as in claim 1;
the substituted substituent is independently selected from one of halogen, cyano, C1-C10 alkyl, C1-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 cycloalkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 monocyclic aryl, C6-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C3-C30 fused ring heteroaryl;
preferably, D is selected from one of the following substituted or unsubstituted groups:
6. the compound of claim 1, wherein E is selected from one of the following groups:
z is1、Z2、Z3、Z4、Z5、Z6、Z7、Z8、Z9、Z10、Z11、Z12、Z13Each independently selected from nitrogen atom or CR7；
The R is7Having the same limits as in claim 3;
z is1、Z2、Z3、Z4、Z5At least one of which is a nitrogen atom;
z is6、Z7、Z8、Z9、Z10、Z11、Z12、Z13At least one of which is a nitrogen atom.
7. A compound according to any one of claims 1,3 or 6, wherein E is selected from one of substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted quinoline, substituted or unsubstituted triazine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline;
the substituted substituent groups are respectively and independently selected from one of halogen, cyano, C1-C10 alkyl, C1-C10 cycloalkyl, C2-C6 alkenyl, C2-C6 cycloalkenyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C30 monocyclic aryl, C6-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C3-C30 condensed ring heteroaryl.
8. The compound of claim 1, wherein the compound is selected from one of the following compounds:
9. use of a compound according to any one of claims 1 to 8 as an electron transport material in an organic electroluminescent device.
10. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layers comprise at least one compound according to any one of claims 1 to 8.
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