CN110128416B - Compound of general formula and application thereof - Google Patents

Compound of general formula and application thereof Download PDF

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CN110128416B
CN110128416B CN201810105112.1A CN201810105112A CN110128416B CN 110128416 B CN110128416 B CN 110128416B CN 201810105112 A CN201810105112 A CN 201810105112A CN 110128416 B CN110128416 B CN 110128416B
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organic electroluminescent
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CN110128416A (en
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张松
杜倩
任雪艳
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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Guan Eternal Material Technology Co Ltd
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Abstract

The invention discloses a general formula compound with the following structure:wherein: z is selected from O, S or Se; l is selected from single bond, or from C 1 ‑C 12 Alkyl, C of (2) 1 ‑C 8 Alkoxy, C 5 ‑C 30 Substituted or unsubstituted arylene, C 3 ‑C 30 A substituted or unsubstituted heterocyclic arylene group; ar (Ar) 1 Selected from the following formula (1) or formula (2):Ar 2 selected from the following formula (3):wherein: x is X 1 ～X 8 Are independently selected from CR 3 Or N, and X 1 ～X 4 At least one of which is N, X 5 ～X 8 At least one of which is N, R 3 Selected from hydrogen, C 1 ‑C 12 Alkyl, C of (2) 6 ‑C 30 Aryl or condensed ring aryl, C 3 ‑C 30 A heterocyclic aryl or fused ring heteroaryl group; r is R 1 ～R 2 Are independently selected from hydrogen, C 1 ‑C 12 Alkyl, C of (2) 6 ‑C 30 Substituted or unsubstituted aryl or condensed ring aryl, C 3 ‑C 30 Substituted or unsubstituted heteroaryl or fused ring heteroaryl. The invention simultaneously protects and adopts the general purposeAn organic electroluminescent device of the compound of formula (I). The compounds of the present invention exhibit excellent device performance and stability when used as host materials in the light emitting layer of an OLED.

Description

Compound of general formula and application thereof
Technical Field
The invention relates to the field of organic electroluminescent materials, in particular to a novel general formula compound and an organic electroluminescent device adopting the general formula compound.
Background
Organic Light-Emitting Diodes (OLEDs) are also known as Organic laser display devices, organic Light-Emitting semiconductors. Is found in the laboratory in 1979 by professor Deng Qingyun of american chinese (child w.tang). The OLED display technology has the advantages of self-luminescence, wide viewing angle, high contrast, low power consumption, high response speed and the like. However, the high-end display screen is also expensive compared with the liquid crystal television. The OLED itself has the inherent property of utilizing an organic thin film and applying a voltage to a device formed by the organic thin film to emit light, so developing a suitable organic thin film material is always a research focus of the OLED industry, which is beneficial to accelerating the industrialization process of the OLED in the display technology.
Full color displays are important indicators to verify whether the display is competitive in the market, with phosphorescent materials being one of the most commonly used organic materials for full color displays. Industry standards for such displays need to be applicable to pixels with higher emission color purity. In particular, these standards require saturated red, green and blue pixels. The color may be measured using CIE coordinates well known in the art.
In a full color display, as described herein, one example of a green phosphorescent material is tris [ 2-phenylpyridine-C 2 ,N]Iridium (III), denoted Ir (ppy) 3 . Phosphorescent materials are generally doped in host materials to increase phosphorescent molecular spacing due to their longer lifetime of the excited state and triplet-triplet annihilation, which causes self-quenching at higher molecular concentrations. It appears that the choice of host material plays a vital role in improving the performance of the organic electroluminescent device. Since most phosphorescent materials generally have only unidirectional carrier transport capacity, this canThe balance of carrier recombination in the light emitting layer is reduced, and therefore, development of a host material having good carrier transport properties is one of the main tasks in the industry.
As used herein, and as understood by one of ordinary skill in the art, triplet-triplet annihilation is the interaction (typically mutual collision) of two atomic or molecular entities in a triplet state such that one of the atomic or molecular entities is in an excited state and the other is in a base state. Typically, but not necessarily, delayed fluorescence is then generated.
Disclosure of Invention
The present invention provides a compound of the general formula represented by formula (1):
wherein: z is selected from O, S or Se;
l is selected from single bond, or from C 1 -C 12 Alkyl, C of (2) 1 -C 8 Alkoxy, C 5 -C 30 Substituted or unsubstituted arylene, C 3 -C 30 A substituted or unsubstituted heterocyclic arylene group;
Ar 1 selected from the following formula (1) or formula (2):
Ar 2 selected from the following formula (3):
in the above formulas (1), (2) and (3):
X 1 ～X 8 are independently selected from CR 3 Or N, and X 1 ～X 4 At least one of which is N, X 5 ～X 8 At least one of which is N, R 3 Selected from hydrogen, C 1 -C 12 Alkyl, C of (2) 6 -C 30 Aryl or condensed ring aryl, C 3 -C 30 A heterocyclic aryl or fused ring heteroaryl group;
R 1 ～R 2 are independently selected from hydrogen, C 1 -C 12 Alkyl, C of (2) 6 -C 30 Substituted or unsubstituted aryl or condensed ring aryl, C 3 -C 30 A substituted or unsubstituted heteroaryl or fused ring heteroaryl group;
l and R as described above 1 ～R 2 The substituents on each are independently selected from halogen, C 1 ～C 10 Alkyl or cycloalkyl, alkenyl, C 1 ～C 6 Alkoxy or thioalkoxy groups, C 6 ～C 30 Monocyclic aromatic or condensed aromatic hydrocarbon group, C 3 ～C 30 A monocyclic heteroarene or a fused heteroarene group.
Further, the above formula (I) is preferably selected from the following formula (II) or formula (III):
in the formula (II) and the formula (III), Z is selected from O, S or Se; l is selected from single bond, or from C 5 -C 15 Substituted or unsubstituted arylene, C 3 -C 15 A substituted or unsubstituted heterocyclic arylene group.
X 1 ～X 8 Is as defined in formula (1) and formula (2), and when X 1 ～X 8 Are independently selected from CR 3 When R is 3 Selected from hydrogen, C 1 -C 8 Alkyl, C of (2) 6 -C 15 Aryl or condensed ring aryl, C 3 -C 15 A heterocyclic aryl group or a fused ring heteroaryl group of (a).
R 1 And R is 2 Are independently selected from hydrogen, C 1 -C 8 Alkyl, C of (2) 6 -C 15 Substituted or unsubstituted aryl or condensed ring aryl, C 3 -C 15 Substituted or unsubstituted heteroaryl or fused-ring heteroarylA base.
The L and R 1 And R is 2 The substituents on each are independently selected from halogen, C 1 ～C 6 Alkyl or cycloalkyl, alkenyl, C 1 ～C 6 Alkoxy or thioalkoxy groups, C 6 ～C 10 Monocyclic aromatic or condensed aromatic hydrocarbon group, C 3 ～C 10 A monocyclic heteroarene or a fused heteroarene group.
Still further, in the above-mentioned compound of the general formula, X is 1 ～X 8 Are independently selected from CR 3 Or N, and preferably X 1 ～X 4 At least two of which are N, preferably X 5 ～X 8 At least two of which are N.
Further, the above formula (II) and formula (III) are respectively the following formula (IV) and formula (V):
therein, Z, L, X 1 ～X 8 R is as follows 1 And R is 2 Is as defined in formulae (II) and (III).
Still further, in the above general structural formula, L is preferably a single bond, or is preferably a group of the following structure:
still further, in the general structural formula, R 1 ～R 2 Each independently is preferably hydrogen, phenyl, biphenyl, naphthyl, fluorenyl, spirofluorenyl, pyridyl, bipyridyl, pyrimidinyl, pyrrolyl, phenylpyridyl, pyrazinyl, quinolinocarbazolyl, 9-phenylcarbazolyl, 9-naphthylcarbazolocarbazolyl.
Still further, preferred among the compounds of the general formula of the present invention are the following structural compounds of 1 to 44:
the compound of the general formula can be applied to an organic electroluminescent device, an organic solar cell, an organic thin film transistor or an organic sensor. Preferably, the organic electroluminescent device can be applied to a light-emitting layer of the organic electroluminescent device as a host material.
The present invention also provides 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, characterized in that the organic layers comprise at least one compound represented by the general formula (i):
wherein: z is selected from O, S or Se; l is selected from single bond, or from C 1 -C 12 Alkyl, C of (2) 1 -C 8 Alkoxy, C 5 -C 30 Substituted or unsubstituted arylene, C 3 -C 30 A substituted or unsubstituted heterocyclic arylene group;
Ar 1 selected from the following formula (1) or formula (2):
Ar 2 selected from the following formula (3):
in the above formulas (1), (2) and (3):
X 1 ～X 8 are independently selected from CR 3 Or N, and X 1 ～X 4 At least one of which is N, X 5 ～X 8 At least one of which is N, R 3 Selected from hydrogen, C 1 -C 12 Alkyl, C of (2) 6 -C 30 Aryl or condensed ring aryl, C 3 -C 30 A heterocyclic aryl or fused ring heteroaryl group;
R 1 ～R 2 are independently selected from hydrogen, C 1 -C 12 Alkyl, C of (2) 6 -C 30 Substituted or unsubstituted aryl or condensed ring aryl, C 3 -C 30 A substituted or unsubstituted heteroaryl or fused ring heteroaryl group;
l and R as described above 1 ～R 2 The substituents on each are independently selected from halogen, C 1 ～C 10 Alkyl or cycloalkyl, alkenyl, C 1 ～C 6 Alkoxy or thioalkoxy groups, C 6 ～C 30 Monocyclic aromatic or condensed aromatic hydrocarbon group, C 3 ～C 30 A monocyclic heteroarene or a fused heteroarene group.
Further, the above formula (I) is preferably selected from the following formula (II) or formula (III):
in the formula (II) and the formula (III), Z is selected from O, S or Se; l is selected from single bond, or from C 5 -C 15 Substituted or unsubstituted arylene, C 3 -C 15 A substituted or unsubstituted heterocyclic arylene group.
X 1 ～X 8 Is as defined in formula (1) and formula (2), and when X 1 ～X 8 Are independently selected from CR 3 When R is 3 Selected from hydrogen, C 1 -C 8 Alkyl, C of (2) 6 -C 15 Aryl or condensed ring aryl, C 3 -C 15 A heterocyclic aryl group or a fused ring heteroaryl group of (a).
R 1 And R is 2 Are independently selected from hydrogen, C 1 -C 8 Alkyl, C of (2) 6 -C 15 Substituted or unsubstituted aryl or condensed ring aryl, C 3 -C 15 Substituted or unsubstituted heteroaryl or fused ring heteroaryl.
The L and R 1 And R is 2 The substituents on each are independently selected from halogen, C 1 ～C 6 Alkyl or cycloalkyl, alkenyl, C 1 ～C 6 Alkoxy or thioalkoxy groups, C 6 ～C 10 Monocyclic aromatic or condensed aromatic hydrocarbon group, C 3 ～C 10 A monocyclic heteroarene or a fused heteroarene group.
Still further, in the above-mentioned compound of the general formula, X is 1 ～X 8 Are independently selected from CR 3 Or N, and preferably X 1 ～X 4 At least two of which are N, preferably X 5 ～X 8 At least two of which are N.
Further, the above formula (II) and formula (III) are respectively the following formula (IV) and formula (V):
therein, Z, L, X 1 ～X 8 R is as follows 1 And R is 2 Is as defined in formulae (II) and (III).
Still further, in the above general structural formula, L is preferably a single bond, or is preferably a group of the following structure:
still further, in the general structural formula, R 1 ～R 2 Are each independently preferably hydrogen, phenyl, biphenyl, naphthyl, fluorenyl, spirofluorenyl, pyridinyl, bipyridyl,Pyrimidinyl, pyrrolyl, phenylpyridyl, pyrazinyl, quinolinylcarbazolyl, 9-phenylcarbazolyl, 9-naphthylcarbazolocarbazolyl.
The novel general formula compound is designed based on stable rigid structures such as dibenzothiophene (or furan or selenophene) serving as a mother nucleus, and further designs a heteroaromatic ring group Ar containing N atoms connected with the compound 1 A bridging group L and a group Ar containing a triazine structure 2 。
The triazine structure-containing group is a good electron transport group, and the triazine group and dibenzothiophene (or furan or selenophene) are both groups with high triplet energy levels, so that the electron cloud overlapping degree between HOMO/LUMO of a compound molecule can be improved, the luminous efficiency of the compound is improved, meanwhile, the band gap caused by the Increase of Charge Transfer (ICT) in the molecule is reduced, and charges are easy to overflow into a dopant, so that the luminous efficiency is reduced; however, the introduction of electron withdrawing groups allows for the whole molecule. The HOMO energy level is pulled low, thereby improving the problems caused by ICT.
Meanwhile, in the compound of the general formula designed by the invention, the heteroaryl ring group Ar containing N atoms 1 The dibenzothiophene (or furan or selenophene) group and the bridging group L are respectively connected at the meta position or the para position, and the structure is designed at the connection site of the meta position or the para position, so that a moderate twisted molecular structure can be ensured, the compound is ensured to have a higher triplet state energy level, the bond dissociation energy can be increased, and the risk of decomposing molecules in a device is reduced. Further, ar in the compound of the present invention is designed by specific optimization 1 Groups and L groups, e.g. Ar bridged by strong electron withdrawing groups such as pyrimidine groups, pyridine groups, etc. as azaaromatic hydrocarbons 1 The group can ensure that the novel compounds have very good intramolecular transmission capability.
When the novel general formula compound is used as a main material in a light-emitting layer of an organic electroluminescent device, the diffusion of excitons in the light-emitting layer of the device can be effectively inhibited, the mobility of electrons in the light-emitting layer of the organic electroluminescent device can be improved, the light-emitting efficiency of the device can be improved, and the stability of the device can be improved, so that the organic electroluminescent device with long service life can be obtained.
In addition, by introducing different electron donating groups and electron withdrawing groups to the parent nucleus structure of the compound for modification, bipolar host materials or electron transporting host materials with good performances can be obtained.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device according to the present invention;
wherein 110 represents a glass substrate, 120 represents an anode, 130 represents a hole injection layer, 140 represents a hole transport layer, 150 represents a light emitting layer, 160 represents an electron transport layer, 170 represents an electron injection layer, and 180 represents a cathode.
FIG. 2 is the Highest Occupied Molecular Orbital (HOMO) of Compound 2 of the present invention;
FIG. 3 is the Lowest Unoccupied Molecular Orbital (LUMO) of Compound 2 of the present invention.
Detailed Description
In order that those skilled in the art will better understand the present invention, the present invention will be described in further detail with reference to specific embodiments.
All compounds of the synthesis process not mentioned in the examples are commercially available starting products. Various chemicals used in the examples such as petroleum ether, ethyl acetate, toluene, tetrahydrofuran, methylene chloride, potassium phosphate, butyllithium, tris (dibenzylideneacetone) dipalladium, tetrakis (triphenylphosphine) palladium, dibenzothiophene-4-boronic acid; 5-bromo-2-iodopyridine; 2 (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine; 2-dicyclohexylphosphine-2 ',6' -dimethoxy biphenyl (spos); tripotassium bis (pinacolato) diboron phosphate; sodium carbonate; basic chemical raw materials such as 1, 4-dioxane and the like can be purchased in the domestic chemical product market.
Analytical testing of intermediates and compounds in the present invention used an absiex mass spectrometer (4000 QTRAP) and a bruk nuclear magnetic resonance (400M).
The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to these examples.
The compound shown in the general formula (I) can be synthesized by adopting dibenzofuran or dibenzothiophene compounds and aza arene through a palladium-catalyzed Suzuki coupling reaction to obtain an intermediate, and then the intermediate is subjected to Suzuki coupling with triazine compounds. A representative synthetic route is as follows:
wherein X is 1 ～X 5 At least one N, and N is not at the connection site; (L) m 、R 1 ～R 2 The meaning of Z in the general formula is the same.
Specific compound synthesis examples:
example 1
Synthesis of Compound 1
Synthesizing an intermediate 1-1;
to a 500mL four-necked flask equipped with a mechanical stirrer under nitrogen protection, dibenzothiophene-4-boronic acid (20 g,87.7mmol,1 eq), 5-bromo-2-iodopyridine (29.8 g,105.2mmol,1.2 eq), tetrakis triphenylphosphine palladium (2 g,1.75mmol,2% eq), sodium carbonate (28 g,263.1mmol,3 eq), toluene 300mL, ethanol 100mL, and water 100mL of the reaction mixture were added and the mixture was refluxed for 24 hours. After cooling to room temperature, 250mL of water was directly added, the aqueous phase was extracted three times with 200mL of dichloromethane, and the organic phases were combined and concentrated to give the crude product. The crude product was boiled in petroleum ether and filtered to give 23g of yellow powder in 80% yield.
Synthesizing an intermediate 1-2;
in a four-necked flask equipped with mechanical stirring under nitrogen protection, 500mL of a condenser was charged with the intermediate 2 (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (30 g,77mmol,1 eq), pinacol biborate (39 g,22mmol,2 eq), tris (dibenzylideneandene acetone) dipalladium (2.2 g,2.3mmol,3% eq), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (Sphos, 3.8g,9.2mmol,12% eq), tripotassium phosphate (49 g,231mmol,3 eq) and dioxane (300 mL of the reaction mixture were refluxed for 24h. After cooling to room temperature, 250mL of water was directly added, the aqueous phase was extracted three times with 200mL of dichloromethane, and the organic phases were combined and concentrated to give the crude product. The crude product was boiled in petroleum ether and filtered to give 27g of white powder in 80% yield.
Synthesis of compound 1;
1-1 (15 g,44mmol,1 eq), 1-2 (20 g,53mmol,1.2 eq), tris (dibenzylideneacetone) dipalladium (1.2 g,1.3mmol,3% eq), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (spos, 4.9g,5.2mmol,12% eq), tripotassium phosphate (28 g,132mmol,3 eq) and dioxane 200mL were added to a 500mL four-necked flask equipped with mechanical stirring under nitrogen. After cooling to room temperature, 250mL of water was directly added, the aqueous phase was extracted three times with 200mL of dichloromethane, and the organic phases were combined and concentrated to give the crude product. The crude product was boiled in petroleum ether and filtered to give 9g of white powder in 40% yield. Mass spectral data for compound 1: MS (MALDI-TOF, m/z) calcd for Chemical Formula:C 38 H 24 N 4 S:568.7.Found:568.6[M] + ；
Similarly, we synthesized the compounds shown in the following table in a similar manner:
device example:
description of the embodiments
The organic light emitting diode includes a first electrode and a second electrode on a substrate, and an organic layer between the first electrode and the second electrode. The organic layer may have at least one light-emitting layer, and may have layers used in organic EL devices such as a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.
Preferably, the organic layer includes a hole injection layer and/or a hole transport layer, a light emitting layer, an electron transport layer, and/or an electron injection layer. The first electrode is an anode, and the second electrode is a cathode; or the first electrode is a cathode, and the second electrode is an anode.
The substrate used for the organic light emitting display is, for example: glass, polymer materials, glass with TFT components, polymer materials, and the like.
The anode material may be transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), or zinc oxide (ZnO), or metal material such as silver or its alloy, aluminum or its alloy, or organic conductive material such as PEDOT, or a multilayer structure of the above materials.
The cathode is magnesium-silver mixture, liF/Al, ITO and other metals, metal mixture and oxide
The hole transport layer or hole injection layer material may be selected from, but is not limited to, HT1-HT31 listed below.
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The "light-emitting layer" refers to an organic layer having a light-emitting function, and when a doping system is used, the organic layer contains a host material and a doping material. In this case, the host material mainly has a function of promoting recombination of electrons and holes and sealing excitons in the light-emitting layer, and the dopant material has a function of efficiently emitting light from excitons obtained by recombination. In the case of a phosphorescent element, the host material mainly has a function of enclosing excitons generated by a dopant in the light-emitting layer.
The host material of the light-emitting layer can be selected from one or more of the compounds of the general formula (1), or selected from the combination of the compounds of the general formula (1) and the materials listed in GPH1-GPH 80:
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the doping material may be selected from GPD1-GPD57, which may be, but is not limited to, listed below:
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the electron transport layer may be, but is not limited to, ET1-ET57 and the like listed below
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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, a combination of one or more of the following.
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
The compounds of the present invention can be used as host materials in the light-emitting layer of an organic electroluminescent device, and the following compounds R1, R2 and R3 are used as host materials in the light-emitting layer in the comparative examples designed according to the present invention, and the structure thereof (the following figures):
the organic electroluminescent device of comparative example 1 was prepared as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
placing the above glass substrate with anode in vacuum chamber, and vacuumizing to 1×10 -5 ～9×10 -3 Pa, vacuum evaporating HI-1 as a hole injection layer on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the thickness of the evaporation film is 10nm;
vacuum evaporation HT-2 is carried out on the hole injection layer to serve as a hole transmission layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 80nm;
vacuum evaporating a luminescent layer of the device on the hole transport layer, wherein the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material R1 is regulated to be 0.1nm/s by utilizing a multi-source co-evaporation method, the evaporation rate of the dye GPD-12 is set to be 3 percent, and the total evaporation film thickness is 30nm;
vacuum evaporating electron transport layer material ET-29 of the device on the luminescent layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 30nm;
LiF with the thickness of 0.5nm is vacuum evaporated on an Electron Transport Layer (ETL) to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
Comparative example 2
The compound of the invention is used as a luminescent main body material.
An organic electroluminescent device was prepared in the same manner as in comparative example, except that R1 was replaced with the compound R2 synthesized in the present invention.
Comparative example 3
The compound of the invention is used as a luminescent main body material.
An organic electroluminescent device was prepared in the same manner as in comparative example, except that R1 was replaced with the compound R3 synthesized in the present invention.
Inventive example 1
The compound of the invention is used as a luminescent main body material.
An organic electroluminescent device was prepared in the same manner as in comparative example, except that R1 was replaced with Compound 1 synthesized in the present invention
Inventive example 2
The compound of the invention is used as a luminescent main body material.
An organic electroluminescent device was prepared in the same manner as in comparative example, except that R1 was replaced with the compound 2 synthesized in the present invention.
Inventive example 3
The compound of the invention is used as a luminescent main body material.
An organic electroluminescent device was prepared in the same manner as in comparative example, except that R1 was replaced with compound 3 synthesized in the present invention.
Inventive example 4
The compound of the invention is used as a luminescent main body material.
An organic electroluminescent device was prepared in the same manner as in comparative example, except that R1 was replaced with the compound 11 synthesized in the present invention.
Inventive example 5
The compound of the invention is used as a luminescent main body material.
An organic electroluminescent device was prepared in the same manner as in comparative example, except that R1 was replaced with the compound 13 synthesized in the present invention.
Inventive example 6 the compounds of the present invention were used as light-emitting host materials.
An organic electroluminescent device was prepared in the same manner as in comparative example, except that R1 was replaced with the compound 25 synthesized in the present invention.
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving voltage and current efficiency of the organic electroluminescent devices and the lifetime of the devices prepared in examples 1 to 6 and comparative examples 1 to 3 were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the luminance of the organic electroluminescent device was measured to reach 10000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time and the current density at the time are measured; the ratio of brightness to current density is the current efficiency.
The device performance detection data of the specific preferred structural compounds disclosed in the device examples of the present invention applied to the organic electroluminescent device are shown in the following table:
device example Host Voltage(V) CE(cd/A)
Comparative example 1 Compound R1 5.2 33
Comparative example 2 Compound R2 5.5 26
Comparative example 3 Compound R3 5.0 28
Device example 1 Compound 1 4.0 65
Device example 2 Compound 2 4.1 53
Device example 3 Compound 3 4.0 68
Device example 4 Compound 11 4.3 50
Device example 5 Compound 13 4.6 51
Device implementationExample 6 Compound 25 5.1 46
In the case where other materials are the same in the structure of the organic electroluminescent device, the compounds of the general formula of the present invention were used instead of the compounds R1, R2 and R3 of the prior art in examples 1 to 3 of the comparative device as the host material of the light-emitting layer, the operating voltage of the devices prepared in examples 1 to 6 of the present invention was reduced compared to the voltage value of the devices prepared by using the comparative compound as the host material of the light-emitting layer, and the devices prepared in examples 1 to 6 were 10000cd/m 2 The current efficiency measured under the brightness is also improved obviously compared with the current efficiency value of the device prepared by the comparative example.
Therefore, when the compound with the general formula is applied to an organic electroluminescent device, compared with devices prepared by materials in the prior art, the prepared OLED device has very good improving effect on both service life and luminous efficiency, so that the organic electroluminescent device has better performance.
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.
Moreover, any combination of the various embodiments of the invention can be made without departing from the spirit of the invention, which should also be considered as disclosed herein.

Claims (5)

1. An organic light-emitting layer general formula compound having a structure represented by formula (v):
wherein Z is selected from O, S or Se;
said X 5 ～X 8 Independently selected from CH or N, X 5 ～X 8 At least two of which are N; l is selected from the following groups:
R 1 ～R 2 and each is independently selected from one of phenyl, biphenyl, naphthyl, fluorenyl and spirofluorenyl.
2. A compound having the following specific structural formula:
3. use of a compound of the general formula according to claim 1 as host material in the light-emitting layer of an organic electroluminescent device.
4. Use of a compound according to claim 2 as host material in the light emitting layer of an organic electroluminescent device.
5. 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, characterized in that one of the compounds described in claim 1 or one of the compounds described in claim 2 is included in the organic layer.
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