CN108947925B - 1,3, 4-oxadiazole derivative, material and organic electroluminescent device - Google Patents

1,3, 4-oxadiazole derivative, material and organic electroluminescent device Download PDF

Info

Publication number
CN108947925B
CN108947925B CN201810958658.1A CN201810958658A CN108947925B CN 108947925 B CN108947925 B CN 108947925B CN 201810958658 A CN201810958658 A CN 201810958658A CN 108947925 B CN108947925 B CN 108947925B
Authority
CN
China
Prior art keywords
layer
organic electroluminescent
oxadiazole derivative
electroluminescent device
organic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201810958658.1A
Other languages
Chinese (zh)
Other versions
CN108947925A (en
Inventor
曹建华
王士波
张建川
董梁
隋岩
唐永顺
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
Original Assignee
Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shijiazhuang Chengzhi Yonghua Display Material Co Ltd filed Critical Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
Priority to CN201810958658.1A priority Critical patent/CN108947925B/en
Publication of CN108947925A publication Critical patent/CN108947925A/en
Application granted granted Critical
Publication of CN108947925B publication Critical patent/CN108947925B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/155—Hole transporting layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H10K85/6565—Oxadiazole compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen

Landscapes

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

Abstract

The invention discloses a 1,3, 4-oxadiazole derivative, a material and an organic electroluminescent device. The structural general formula of the 1,3, 4-oxadiazole derivative is shown as a formula I:

Description

1,3, 4-oxadiazole derivative, material and organic electroluminescent device
Technical Field
The invention relates to the technical field of organic electroluminescent display. And more particularly, to a 1,3, 4-oxadiazole derivative, a material, and an organic electroluminescent device.
Background
Organic electroluminescence (abbreviated as OLED) and related research firstly discovered the electroluminescence phenomenon of organic compound single crystal anthracene in pope et al as early as 1963. Kodak company of the United states of 1987 made an amorphous film device by evaporating small organic molecules, and reduced the driving voltage to within 20V. The device has the advantages of ultra-light weight, full curing, self luminescence, high brightness, wide viewing angle, high response speed, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristic, soft display and the like, and can be widely applied to flat panel displays and surface light sources, so the device is widely researched, developed and used.
Through the development of twenty years, the organic EL material has comprehensively realized red, blue and green luminescence, and the application field has also been expanded from small molecules to the fields of high molecules, metal complexes and the like. In recent years, organic electroluminescent display technologies have become mature, and some products have entered the market, but in the process of industrialization, many problems still need to be solved, especially, many problems still remain unsolved, such as carrier injection, transport performance, material electroluminescent performance, service life, color purity, matching between various materials and between various electrodes, and the like, of various organic materials used for manufacturing devices.
Disclosure of Invention
The invention aims to provide a 1,3, 4-oxadiazole derivative, a synthesis method thereof and application thereof in an organic electroluminescent diode.
The invention provides a 1,3, 4-oxadiazole derivative, which has a structural general formula shown in formula I:
Figure BDA0001773284300000011
wherein: r1Any one selected from substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic aryl;
x is selected from any group from A to H, wherein a plurality of attachment sites on one group means that a Y group is attached to each attachment site;
Figure BDA0001773284300000023
in the present invention, a linking site or a substitution site is represented;
Figure BDA0001773284300000021
wherein R is2To R8Are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carbonyl group, an ester group, a thioimino group, a thioamino group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted alkyl groupAny one of substituted alkoxy, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic aryl.
Preferably, the substituted or unsubstituted heterocyclic aryl group is selected from the structures II-1 to II-22:
Figure BDA0001773284300000022
Figure BDA0001773284300000031
wherein Z is1、Z2、Z3Independently selected from any one of hydrogen, deuterium, a halogen atom, hydroxyl, cyano, nitro, ester group, carboxyl or carboxylate thereof, sulfonic acid group or sulfonate thereof, phosphoric acid group or phosphate thereof, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy and substituted or unsubstituted arylthio;
x1 is an integer of 1-4; x2 is an integer of 1-3; x3 is an integer of 1-2; x4 is an integer of 1-6; x5 is an integer of 1-5;
T1is an oxygen or sulfur atom.
Preferably, the substituent of the substituted alkyl group, the substituted alkoxy group, the substituted alkenyl group, the substituted aryl group, the substituted aryloxy group and the substituted arylthio group is selected from any one or more of deuterium, a halogen atom and a cyano group.
Preferably, the 1,3, 4-oxadiazole derivative is any one of the following structural formulas CJH 1-CJH 88:
Figure BDA0001773284300000032
Figure BDA0001773284300000041
Figure BDA0001773284300000051
Figure BDA0001773284300000061
Figure BDA0001773284300000071
Figure BDA0001773284300000081
in a second aspect, the present invention provides a material comprising the above 1,3, 4-oxadiazole derivative.
Preferably, the material is a light emitting material and/or a hole material in an organic electroluminescent device.
In a third aspect, the present invention provides an organic electroluminescent device, wherein the material of the organic electroluminescent device comprises the above 1,3, 4-oxadiazole derivative.
Preferably, the organic electroluminescent device comprises a transparent substrate, an anode layer, a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer and a cathode layer which are arranged in sequence from bottom to top.
Preferably, the material of the transparent substrate is glass or a flexible substrate;
the anode layer is made of inorganic materials or organic conducting polymers; wherein the inorganic material is indium tin oxide, zinc oxide, tin zinc oxide, gold, silver or copper; the organic conducting polymer is selected from at least one of polythiophene, sodium polyvinyl benzene sulfonate and polyaniline;
the material constituting the hole injection layer is the 1,3, 4-oxadiazole derivative of claim 1 or a doped 1,3, 4-oxadiazole derivative of claim 1;
the material constituting the hole transport layer is the 1,3, 4-oxadiazole derivative of claim 1 or a doped 1,3, 4-oxadiazole derivative of claim 1;
the material for forming the organic light-emitting layer comprises a host material and a doping material; wherein the doped material comprises red, green and blue doped materials; the main body material comprises the following materials:
Figure BDA0001773284300000091
the material constituting the electron transport layer comprises the 1,3, 4-oxadiazole derivative of claim 1 and a metal complex comprising:
Figure BDA0001773284300000092
the cathode layer is made of a material selected from one or two of lithium, magnesium, silver, calcium, strontium, aluminum, indium, copper, gold and silver, or a fluoride.
The blue-doped material is as follows, but not limited to the following materials:
Figure BDA0001773284300000101
Figure BDA0001773284300000111
the red-doped material is as follows, but not limited to the following materials:
Figure BDA0001773284300000112
the green doped material is as follows, but not limited to the following materials:
Figure BDA0001773284300000121
the material constituting the electron transport layer is a complex of a compound represented by formula I and other metals, and has the following structure, but is not limited to the following materials:
Figure BDA0001773284300000122
the cathode layer is made of a material selected from any one or two of the following elements: lithium, magnesium, silver, calcium, strontium, aluminum, indium, copper, gold, and silver.
Preferably, the hole injection layer has a thickness of 30-50nm, in particular 40 nm.
The thickness of the hole transport layer is 5-15nm, specifically 10 nm.
The thickness of the organic light-emitting layer is 10-100nm, specifically 40 nm.
The thickness of the electron transport layer is 10-30nm, specifically 20 nm.
The thickness of the cathode layer is 90-110nm, specifically 100 nm.
The invention has the following beneficial effects:
the organic electroluminescent material shown in the formula I has the capacity of blocking hole aggregation and the capacity of electron transmission, and the organic electroluminescent device prepared by using the material can reduce the starting voltage, improve the current efficiency and the electroluminescent efficiency of the device and prolong the service life of the device. The series of materials have good film-forming properties, and the methods for synthesizing and purifying the materials are simple and suitable for large-scale production, and the like, so that the series of materials are ideal choices for being used as P-type doped materials of organic electroluminescent devices.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
The method is a conventional method unless otherwise specified. The starting materials are commercially available from the open literature unless otherwise specified.
The following examples are provided for testing the performance of OLED materials and devices using the following test apparatus and method:
OLED device performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C.
Abbreviations used in the following examples are defined as follows:
THF tetrahydrofuran
DMSO dimethyl sulfoxide
LDA lithium diisopropylamide
Et3N-Triethylamine
Pd(PPh3)4Tetrakis (triphenylphosphine) palladium
Boc2Di-tert-butyl O dicarbonate
LiTMP 2,2,6, 6-tetramethylpiperidine-1-lithium
The following examples, the synthetic route is as follows:
Figure BDA0001773284300000141
EXAMPLE 1 preparation of Compound CJH1
The first step is as follows: preparation of intermediate int. -1-1
Figure BDA0001773284300000142
4.0g (40mmol) of cyanoacethydrazide is dissolved in 100mL of anhydrous THF, the temperature is reduced to 0 ℃ in an ice-water bath, 4.5g (44mmol) of triethylamine is added, 9.22g (40mmol) of 2,3,4,5, 6-pentafluorobenzoyl chloride is slowly added dropwise, the mixture is stirred and reacted for 1 hour, the mixture is heated to room temperature and stirred and reacted for 1 hour, 50mL of saturated aqueous ammonium chloride solution is added dropwise, the mixture is extracted with ethyl acetate, the organic phase is dried with anhydrous sodium sulfate, filtered, the filtrate is concentrated under reduced pressure and dried, and is recrystallized by ethanol, 9.6g of white solid is obtained, and the yield is 82%.
The second step is that: preparation of intermediate int. -2-1
Figure BDA0001773284300000143
Dispersing 9g (30.7mmol) of intermediate int. -1-1 and 50mL of phosphorus oxychloride, heating to reflux and stirring for reaction for 12 hours, concentrating under reduced pressure to dryness, adding 50mL of ice water, filtering, washing a filter cake with water, decoloring with a short silica gel column, concentrating under reduced pressure to dryness, and recrystallizing with ethanol to obtain 8.1g of white solid with the yield of 96%.
The third step: preparation of compound CJH1
Figure BDA0001773284300000151
8g (29mmol) of intermediate int. -2-1 was dissolved in 80mL of toluene, 2.6g (14.5mmol) of 2,3,5, 6-tetrafluoroterephthalquinone and 4.6g (58.2mmol) of pyridine were added, 0.55g (2.9mmol) of titanium tetrachloride was added with stirring at room temperature, the reaction was stirred for 1 hour, the temperature was raised to 60 ℃ and the reaction was stirred for 24 hours, 500mL of a saturated aqueous ammonium chloride solution was added, the mixture was filtered, the filter cake was washed with water, and the filtrate was washed with ethyl acetate-petroleum ether to obtain 8.9g of a white solid with a yield of 89%. MS: c26F14N6O2Test result 695[ M + H ]]+
EXAMPLE 2 preparation of Compound CJH8
The first step is as follows: preparation of intermediate int. -3-1
Figure BDA0001773284300000152
11.28g (40mmol) of intermediate int. -2-2 was dissolved in 100mL of dry THF, cooled to 0 ℃ under nitrogen, and 3.0g (60% oil dispersion, 72.8mmol) of sodium hydride was added in portions, stirred for reaction for 1 hour, 4.8g (17.6mmol) of perfluoronaphthalene was added, the mixture was heated to reflux and stirred for reaction for 24 hours, concentrated to dryness under reduced pressure, and 50g of an ice water solution was added, filtered, and the filter cake was washed with water to give 9.1g of a yellow solid with a yield of 65%.
The second step is that: preparation of compound CJH8
Figure BDA0001773284300000161
8g (10.0mmol) of the intermediate int. -3-1 is dissolved by 100mL of dichloromethane, the temperature is raised to reflux, 3.2g (20.0mmol) of bromine is slowly added dropwise under the irradiation of a 125W high-pressure mercury lamp, the reaction is continuously stirred for 1 hour after the dropwise addition, the reaction is cooled to room temperature, 100mL of sodium carbonate aqueous solution is added dropwise, the pressure is reduced, the filtration is carried out, and a filter cake is washed by water, so that 4.1g of light yellow green solid is obtained, and the yield is 52%. MS: c32F14N8O2Test results 795[ M + H ]]+
EXAMPLE 3 preparation of Compound CJH13
Figure BDA0001773284300000162
11g (40mmol) of intermediate int. -2-1 was dissolved in 100mL of dry dichloromethane, cooled to-30 ℃ under nitrogen protection, 3.6g (20mmol) of tetrachlorocyclopropene was added, the mixture was stirred for reaction for 1 hour, 13.2g (130mmol) of triethylamine was slowly added dropwise, the mixture was stirred for reaction for 24 hours after warming to room temperature, 100mL of ice-water solution was added, the mixture was filtered, and the filter cake was washed with water to obtain 7.8g of yellow solid with a yield of 46%. MS: c33F15N9O3Test result 856[ M + H ]]+
Example 4 preparation of Compounds CJH 2-CJH 6, CJH 10-CJH 11, CJH 17-CJH 56, CJH 60-CJH 67, CJH 70-CJH 88
Referring to the synthesis method of example 1, compounds CJH 2-CJH 6, CJH 10-CJH 11, CJH 17-CJH 56, CJH 60-CJH 67 and CJH 70-CJH 88 were prepared, i.e., the method steps were the same as example 1 except that different reactants were used according to actual needs to replace SM-0-0 in the first step of example 1 and 2,3,5, 6-tetrafluoro-p-benzoquinone in the third step of example 1 according to molar amounts and the mass amounts of the compounds were changed according to molar amounts.
Example 5 preparation of Compounds CJH7, CJH9, CJH12, CJH68, CJH69
Referring to the synthesis process of example 2, compounds CJH7, CJH9, CJH12, CJH68 and CJH69 were prepared, i.e., the process steps were the same as example 2, except that int. -2-2 of the first step of example 2 was replaced with different reactants according to actual needs according to the desired products, and the mass amounts of the compounds were changed according to molar amounts.
Example 6 preparation of Compounds CJH 14-CJH 16, CJH 57-CJH 59
Referring to the synthesis method of example 3, compounds CJH 14-CJH 16 and CJH 57-CJH 59 were prepared, i.e., the method steps were the same as example 3, except that int. -2-1 in example 3 was replaced with different reactants according to actual needs according to the difference of the desired products, and the mass amounts of the compounds were changed according to molar amounts.
Example 7 preparation of devices OLED-1 to OLED-6
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, washed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked to be completely dry in a clean environment, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, evaporating a compound NPB on the anode layer film to form a hole injection layer, wherein the obtained hole injection layer is doped with the compound (formula I) of the invention by 25 percent by weight, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40 nm;
3) continuously evaporating NPB on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
4) continuously evaporating AND plating an AND (host material) AND a DPVBi (doping material) on the hole transport layer, wherein the AND is DPVBi (98: 2) AND is used as an organic light-emitting layer of the device, the evaporation rate is 0.1nm/s, AND the thickness of the organic light-emitting layer obtained by evaporation is 40 nm;
5) continuously evaporating a layer of Alq3 on the organic light-emitting layer to be used as an electron transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20 nm;
6) and sequentially evaporating a magnesium/silver alloy layer on the electron transport layer to serve as a cathode layer of the device, wherein the evaporation rate of the magnesium/silver alloy layer is 2.0-3.0 nm/s, the evaporation film thickness is 100nm, and the mass ratio of magnesium to silver is 1: and 9, obtaining the OLED device provided by the invention.
Selecting the compound (formula I) in the step 2) as a compound CJH1 according to the same procedure as above to obtain the OLED-1 provided by the invention;
selecting the compound (formula I) in the step 2) as a compound CJH7 according to the same procedure as above to obtain the OLED-2 provided by the invention;
selecting the compound (formula I) in the step 2) as a compound CJH13 according to the same procedure as above to obtain the OLED-3 provided by the invention;
selecting the compound (formula I) in the step 2) as a compound CJH20 according to the same procedure as above to obtain the OLED-4 provided by the invention;
selecting the compound (formula I) in the step 2) as a compound CJH41 according to the same procedure as above to obtain the OLED-5 provided by the invention;
replacing the compound (formula I) in the step 2) with HATCN according to the same steps as above to obtain a comparative device OLED-6;
the results of the performance tests of the obtained devices OLED-1 to OLED-6 are shown in Table 1.
TABLE 1 Performance test results of OLED-1 to OLED-6
Figure BDA0001773284300000181
From the above, the device prepared from the organic material of the present invention has low lighting voltage, and under the same current density, the efficiency is obviously higher than that of the device doped with HATCN as P, and the half-life period of the device is prolonged by 3 times.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.

Claims (7)

1. A1, 3, 4-oxadiazole derivative having the structural formula:
Figure FDA0002672837320000011
2. a material comprising the 1,3, 4-oxadiazole derivative of claim 1.
3. The material according to claim 2, wherein the material is a light-emitting material and/or a hole material in an organic electroluminescent device.
4. An organic electroluminescent element, characterized in that the material of the organic electroluminescent element comprises the 1,3, 4-oxadiazole derivative according to claim 1.
5. The organic electroluminescent device according to claim 4, wherein the organic electroluminescent device comprises a transparent substrate, an anode layer, a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer and a cathode layer, which are sequentially arranged from bottom to top.
6. The organic electroluminescent device according to claim 5, wherein the transparent substrate is made of glass or a flexible substrate;
the anode layer is made of inorganic materials or organic conducting polymers; wherein the inorganic material is indium tin oxide, zinc oxide, tin zinc oxide, gold, silver or copper; the organic conducting polymer is selected from at least one of polythiophene, sodium polyvinyl benzene sulfonate and polyaniline;
the material constituting the hole injection layer is the 1,3, 4-oxadiazole derivative of claim 1 or a doped 1,3, 4-oxadiazole derivative of claim 1;
the material constituting the hole transport layer is the 1,3, 4-oxadiazole derivative of claim 1 or a doped 1,3, 4-oxadiazole derivative of claim 1;
the material for forming the organic light-emitting layer comprises a host material and a doping material; wherein the doped material comprises red, green and blue doped materials; the main body material comprises the following materials:
Figure FDA0002672837320000021
the material constituting the electron transport layer comprises the 1,3, 4-oxadiazole derivative of claim 1 and a metal complex comprising:
Figure FDA0002672837320000022
the cathode layer is made of a material selected from one or two of lithium, magnesium, silver, calcium, strontium, aluminum, indium, copper, gold and silver, or a fluoride.
7. The organic electroluminescent device according to claim 6,
the thickness of the hole injection layer is 30-50 nm;
the thickness of the hole transport layer is 5-15 nm;
the thickness of the organic light-emitting layer is 10-100 nm;
the thickness of the electron transmission layer is 10-30 nm;
the thickness of the cathode layer is 90-110 nm.
CN201810958658.1A 2018-08-22 2018-08-22 1,3, 4-oxadiazole derivative, material and organic electroluminescent device Active CN108947925B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810958658.1A CN108947925B (en) 2018-08-22 2018-08-22 1,3, 4-oxadiazole derivative, material and organic electroluminescent device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810958658.1A CN108947925B (en) 2018-08-22 2018-08-22 1,3, 4-oxadiazole derivative, material and organic electroluminescent device

Publications (2)

Publication Number Publication Date
CN108947925A CN108947925A (en) 2018-12-07
CN108947925B true CN108947925B (en) 2020-12-01

Family

ID=64473516

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810958658.1A Active CN108947925B (en) 2018-08-22 2018-08-22 1,3, 4-oxadiazole derivative, material and organic electroluminescent device

Country Status (1)

Country Link
CN (1) CN108947925B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110437103B (en) * 2019-08-01 2021-01-26 宁波卢米蓝新材料有限公司 Cyclic compound, application thereof and electronic device
CN112679503B (en) * 2020-12-14 2022-08-23 阜阳欣奕华材料科技有限公司 P-type dopant, intermediate thereof and application thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102192692B1 (en) * 2015-06-30 2020-12-17 (주)피엔에이치테크 An electroluminescent compound and an electroluminescent device comprising the same

Also Published As

Publication number Publication date
CN108947925A (en) 2018-12-07

Similar Documents

Publication Publication Date Title
EP1499624B1 (en) Electroluminescent materials
KR101041642B1 (en) Compound for organic electroluminescent device and organic electroluminescent device
CN107021956B (en) Benzoxazole derivative and application thereof
CN107722062B (en) Metal iridium or platinum complex and organic electroluminescent device containing metal iridium or platinum complex
JP2015029117A (en) Organic electroluminescent device arranged by use of organic electroluminescent compound
WO2019056932A1 (en) Imidazole derivative, and material and organic light-emitting device comprising same
KR20090093688A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN109942637B (en) Metal complex and organic electroluminescent device
JP7458483B2 (en) Metal complexes and their uses
CN107573925B (en) Organic electroluminescent compound
CN111675718A (en) Compound, organic light-emitting device comprising compound, display panel and display device
CN109400590A (en) Thermal activation delayed fluorescent material and application thereof in organic light-emitting diode
CN113201027A (en) Metal complex and application thereof
CN105481672A (en) Series of fluorescent OLED materials
CN110903301A (en) Phosphorescent compound and organic light emitting diode device using the same
JP2024510953A (en) Neutral iridium complex coordinated with biphenyl derivative, and its production method and use
CN111072677A (en) Organic compound and application thereof
CN108947925B (en) 1,3, 4-oxadiazole derivative, material and organic electroluminescent device
CN103739607A (en) Tri-carbazole multi-arm structural red-light--emitting material and preparation method and application thereof
CN109912564B (en) Compound with cyano-group aza-benzene as core and application of compound in OLED device
CN101504972B (en) Electroluminescent device made from rare-earth terbium complex
CN111471450A (en) Organic light-emitting compound, preparation method thereof and organic electroluminescent device
CN108821934B (en) Compound, organic electroluminescent device containing compound and material thereof
CN114560870B (en) Sulfur-containing polycyclic aromatic compound and application thereof
CN107573328B (en) Indenoimidazole compound, material containing same and organic electroluminescent device

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant