CN111116602B - OLED material and application thereof in organic electroluminescent device - Google Patents

OLED material and application thereof in organic electroluminescent device Download PDF

Info

Publication number
CN111116602B
CN111116602B CN201911194872.5A CN201911194872A CN111116602B CN 111116602 B CN111116602 B CN 111116602B CN 201911194872 A CN201911194872 A CN 201911194872A CN 111116602 B CN111116602 B CN 111116602B
Authority
CN
China
Prior art keywords
compound
oled material
oled
hole transport
layer
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
CN201911194872.5A
Other languages
Chinese (zh)
Other versions
CN111116602A (en
Inventor
段陆萌
范洪涛
黄春雪
杭德余
梁现丽
李仲庆
曹占广
刘阳
班全志
李继响
罗忠林
呼建军
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.)
Beijing Yanhua Jilian Optoelectronic Technology Co ltd
Original Assignee
Beijing Yanhua Jilian Optoelectronic Technology 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 Beijing Yanhua Jilian Optoelectronic Technology Co ltd filed Critical Beijing Yanhua Jilian Optoelectronic Technology Co ltd
Priority to CN201911194872.5A priority Critical patent/CN111116602B/en
Publication of CN111116602A publication Critical patent/CN111116602A/en
Application granted granted Critical
Publication of CN111116602B publication Critical patent/CN111116602B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/06—Peri-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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • 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
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Landscapes

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

Abstract

The invention relates to an OLED material which has any one structure shown in general formulas I to III. The OLED material provided by the invention is a compound which takes tonne-to-tonne as a center and has a high T1 energy level, a narrow band gap and a shallow Highest Occupied Molecular Orbital (HOMO) energy level. The perixanthenoxanthene is easily sublimable, stable in air, and does not undergo oxidative decomposition. Has high thermal stability and high glass transition temperature in air. By introducing a group with larger steric hindrance, the luminescent material is not easy to crystallize and quench and has good film-forming property. In a preferred embodiment of the present invention, the OLED material is used as a hole transport material for a hole transport layer.

Description

OLED material and application thereof in organic electroluminescent device
Technical Field
The invention relates to the technical field of organic electroluminescent display, in particular to an OLED material and application thereof in an organic electroluminescent device.
Background
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements for the performance of flat panel display devices are higher and higher. The main display technologies at present are plasma display devices, field emission display devices, and organic electroluminescent display devices (OLEDs). The OLED has a series of advantages of self luminescence, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, and compared with a liquid crystal display device, the OLED does not need a backlight source, has a wider viewing angle and low power consumption, has the response speed 1000 times that of the liquid crystal display device, and has a wider application prospect.
The organic hole transport material reported at present has the defects that the molecular weight is generally small, the glass transition temperature of the material is low, the material is easy to crystallize after repeated charging and discharging in the use process of the material, and the uniformity of a thin film is damaged, so that the service life of the material is influenced. Therefore, the stable and efficient organic hole transport material is developed, so that the driving voltage is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the organic hole transport material has important practical application value.
The Peri-xanthoxanthene (PXX) is a condensed ring aromatic compound having 22 pi electrons in a divalent cation and a conjugated system of 22 atoms (20 carbon atoms and 2 oxygen atoms) and is very stable. The xanthenoxanthene is often used as an electron donor in charge transfer complexes and therefore has potential as a hole transport material.
Disclosure of Invention
The invention aims to provide an OLED hole transport material which is not easy to quench, crystallize and has good film forming property, and an OLED device using the compound.
Specifically, the invention provides an OLED material, which has any one of the structures shown in general formulas I-III:
Figure GDA0002988250860000021
in the general formulas I to III, R1By substitution of H atoms at any one or two positions on the phenyl ring in which it is located, R2By substitution of H atoms in any one, two or three positions of the phenyl ring in which they are located, R3By substitution of H atoms in any one, two or three positions of the phenyl ring in which they are located, R4Substituted with H atoms at any one, two or three positions on the phenyl ring on which it is located.
The R is1、R2、R3、R4Each independently represents-H, -F, -Cl, -Br, -I, -n (Ar), -C (═ O) Ar, -P (═ O) Ar, -S (═ O)2Ar、-OAr、-SAr、-CN、-NO2An alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms or a sulfoalkoxy group having 1 to 40 carbon atoms.
The alkyl group having 1 to 40 carbon atoms may be a straight-chain alkyl group having 1 to 40 carbon atoms, a branched-chain alkyl group having 3 to 40 carbon atoms, or a cyclic alkyl group having 3 to 40 carbon atoms.
The alkoxy group having 1 to 40 carbon atoms may be a linear alkoxy group having 1 to 40 carbon atoms, a branched alkoxy group having 3 to 40 carbon atoms, or a cyclic alkoxy group having 3 to 40 carbon atoms.
The thioalkoxy group having 1 to 40 carbon atoms may be a linear thioalkoxy group having 1 to 40 carbon atoms, a branched thioalkoxy group having 3 to 40 carbon atoms, or a cyclic thioalkoxy group having 3 to 40 carbon atoms.
The R is1、R2、R3、R4The groups represented by each may be different, any two of them may be the same and different from the remaining two, any three of them may be the same and different from the remaining one, or four of them may be the same.
As a specific embodiment of the present invention, R is1、R2、R3、R4All represent H atoms.
In the general formulas I to III of the present invention for Ar1、Ar2The respective substitution positions are preferably selected to enhance the overall performance of the compound. Specifically, the method comprises the following steps:
in the general formula II, Ar1、Ar2The respective specific substitution positions are preferably as shown in the general formulae II-1 to II-3.
Figure GDA0002988250860000022
In the general formula III, Ar1、Ar2The respective specific substitution positions are preferably as shown in the general formulae III-1 to III-6.
Figure GDA0002988250860000031
As a specific embodiment of the invention, the OLED material has a structure shown as a general formula II-1.
As a specific embodiment of the present invention, the OLED material has a structure shown in the general formula II-1'.
Figure GDA0002988250860000032
Ar of the invention1、Ar2Each independently represents a group having an N-phenylcarbazole parent nucleus or represents an H atom, and Ar1、Ar2Not being H atoms at the same time。
Preferably, Ar is1、Ar2Each independently selected from the group consisting of:
Figure GDA0002988250860000033
Figure GDA0002988250860000041
ar is1、Ar2The substituents represented by each may be the same or different.
In each of the above-mentioned substituent groups,
Figure GDA0002988250860000042
or "- - -" represents a substituted position.
As a particular embodiment of the present invention, the OLED material is selected from compounds of the following specific structures:
Figure GDA0002988250860000043
Figure GDA0002988250860000051
Figure GDA0002988250860000061
Figure GDA0002988250860000071
Figure GDA0002988250860000081
the invention also provides a preparation method of the OLED material.
When in formula I Ar1、Ar2The radicals being identical, i.e. Ar1、Ar2When all Ar is contained, the method for synthesizing the compound shown in the general formula I comprises the following steps: taking a compound P-I as a raw material, and carrying out a coupling reaction with Ar to obtain a compound I;
the reaction process is as follows:
Figure GDA0002988250860000082
when in formula I Ar1、Ar2When the groups are different, the method for synthesizing the compound shown in the general formula I comprises the following steps: taking a compound P-I' as a raw material, and sequentially reacting with Ar1、Ar2Carrying out coupling reaction to obtain a compound I;
the reaction process is as follows:
Figure GDA0002988250860000083
when in formula II Ar1、Ar2The radicals being identical, i.e. Ar1、Ar2When both are Ar, the method for synthesizing the compound shown in the general formula II comprises the following steps: taking a compound P-II as a raw material, and carrying out a coupling reaction with Ar to obtain a compound II;
the reaction process is as follows:
Figure GDA0002988250860000091
when in formula II Ar1、Ar2When the groups are different, the method for synthesizing the compound shown in the general formula II comprises the following steps: taking a compound P-II 'as a raw material, and reacting the compound P-II' with Ar in sequence1、Ar2Carrying out coupling reaction to obtain a compound II;
the reaction process is as follows:
Figure GDA0002988250860000092
when in formula III Ar1、Ar2The radicals being identical, i.e. Ar1、Ar2When both are Ar, the method for synthesizing the compound shown in the general formula III comprises the following steps: taking a compound P-III as a raw material, and carrying out a coupling reaction with Ar to obtain a compound III;
the reaction process is as follows:
Figure GDA0002988250860000093
when in formula III Ar1、Ar2When the groups are different, the method for synthesizing the compound shown in the general formula III comprises the following steps: taking a compound P-III 'as a raw material, and reacting the compound P-III' with Ar in sequence1、Ar2Carrying out coupling reaction to obtain a compound III;
the reaction process is as follows:
Figure GDA0002988250860000094
Figure GDA0002988250860000101
the above steps can be carried out by a person skilled in the art by known and conventional means, such as selecting a suitable catalyst, solvent, determining a suitable reaction temperature, time, etc.
In the above process for preparing a compound represented by any one of the general formulae I to III, when Ar is Ar1、Ar2The radicals being identical, i.e. Ar1、Ar2When both are Ar, as a preferred embodiment of the present invention, the method comprises: and (2) taking xylene as a reaction solvent, cuprous chloride as a catalyst, potassium hydroxide as an alkali, controlling the temperature to be 75-85 ℃ under the protection of nitrogen, and performing a coupling reaction on the raw materials and Ar to obtain the target compound.
Any one of the above-mentioned preparation general formulas I to IIIIn the process of the compound (1), when Ar is1、Ar2When the groups are different, as a preferred embodiment of the present invention, the method comprises: firstly, dimethylbenzene is used as a reaction solvent, cuprous chloride is used as a catalyst, potassium hydroxide is used as alkali, nitrogen is used for protection, the temperature is controlled to be 75-85 ℃, and the raw material and Ar are mixed1Coupling reaction is carried out to obtain an intermediate product; and then taking toluene as a solvent, palladium acetate and tri-tert-butylphosphine as catalysts, potassium tert-butoxide as an alkali, protecting with nitrogen, controlling the temperature to be 90-120 ℃, and reacting the intermediate product and Ar2Coupling reaction is carried out to obtain the target compound.
The starting materials for the solvents, catalysts, bases, etc., used in the present invention can be synthesized by published commercial routes or methods known in the art.
The invention also protects the application of the OLED material in an organic electroluminescent device. Preferably, the OLED material is used as a hole transport material in a hole transport layer.
The invention also provides an organic electroluminescent device, and a hole transport layer of the organic electroluminescent device contains the OLED material. Specifically, the organic electroluminescent device protected by the invention sequentially comprises a transparent substrate, an anode layer, a hole transport layer, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer, wherein the hole transport layer, the electroluminescent layer, the electron transport layer, the electron injection layer and the cathode layer are formed by the OLED material.
The OLED material provided by the invention is a compound which takes tonne-to-tonne as a center and has a high T1 energy level, a narrow band gap and a shallow Highest Occupied Molecular Orbital (HOMO) energy level. The perixanthenoxanthene is easily sublimable, stable in air, and does not undergo oxidative decomposition. Has high thermal stability and high glass transition temperature in air. By introducing a group with larger steric hindrance, the luminescent material is not easy to crystallize and quench and has good film-forming property.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
According to some embodiments of the present invention, the preferred solvent for preparing the organic electroluminescent device according to the present invention is selected from toluene, DMF or a mixture of these solvents. The reagents are analytically pure reagents, and the intermediate is purchased from an online shopping mall or is custom-synthesized from outsourcing companies.
Example 1
Figure GDA0002988250860000111
Synthesis of (Compound II-1-4)
The synthetic route is as follows:
Figure GDA0002988250860000112
synthesis of Compound II-1-4
A1L three-necked flask was stirred with magnetic stirring and then charged with 40.07g (0.378mol) of sodium carbonate, 60.27g (99% purity, 0.21mol) of 4- (9H-carbazol-9-yl) phenyl) boronic acid and 100ml of toluene in this order after nitrogen substitution. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 44g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, the temperature being controlled between 75 and 90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, repeatedly boiling and washing the filter cake with DMF for several times, and filtering to obtain 60.36g of light yellow solid with purity of 99% and yield of 79%.
Product MS (m/e): 523; elemental analysis (C)38H21NO2): theoretical value C: 87.17%, H: 4.04%, N: 2.68%, O: 6.11 percent; found value C: 87.16%, H: 4.05%, N: 2.68%, O: 6.11 percent.
Example 2
Figure GDA0002988250860000113
Synthesis of (Compound II-1-14)
The synthetic route is as follows:
Figure GDA0002988250860000121
synthesis of Compound II-1-14
A1L three-necked flask is stirred by magnetic force, and added with 40.07g (0.378mol) of sodium carbonate, 70.77g (purity 99%, 0.21mol) of (5-phenyl-5H-benzo [ b ] carbazol-3-yl) boric acid and 100ml of toluene in sequence after nitrogen replacement. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 44g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, the temperature being controlled between 75 and 90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, repeatedly boiling and washing the filter cake with DMF for several times, and filtering to obtain 46.41g of light yellow solid with purity of 99% and yield of 81%.
Product MS (m/e): 573; elemental analysis (C)42H23NO2): theoretical value C: 87.94%, H: 4.04%, N: 2.44%, O: 5.58 percent; found value C: 87.93%, H: 4.05%, N: 2.44%, O: 5.58 percent.
Example 3
Figure GDA0002988250860000122
Synthesis of (Compound II-1-19)
The synthetic route is as follows:
Figure GDA0002988250860000123
synthesis of Compounds II-1-19
A1 liter three-necked flask was stirred with magnetic stirring and then charged with 40.07g (0.378mol) of sodium carbonate, (81.27 g (purity 99%, 0.21mol) of 9-phenyl-9H-dibenzo [ a, c ] carbazol-11-yl) boronic acid and 100ml of toluene in this order after nitrogen substitution. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 44g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, the temperature being controlled between 75 and 90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, repeatedly boiling and washing the filter cake with DMF for several times, and filtering to obtain 49.84g of light yellow solid with purity of 99% and yield of 80%.
Product MS (m/e): 623; elemental analysis (C)46H25NO2): theoretical value C: 88.58 percent; h: 4.04 percent; n: 2.25 percent; o: 5.13 percent; found value C: 88.57 percent; h: 4.05 percent; n: 2.25 percent; o: 5.13 percent.
Example 4
Figure GDA0002988250860000131
Synthesis of (Compound II-1-21)
The synthetic route is as follows:
Figure GDA0002988250860000132
synthesis of Compound II-1-21
A1L three-necked flask is stirred by magnetic force, and added with 40.07g (0.378mol) of sodium carbonate, 60.27g (purity 99 percent, 0.21mol) of (9-phenyl-9H-carbazole-2-yl) boric acid and 100ml of toluene in turn after nitrogen replacement. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 44g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, the temperature being controlled between 75 and 90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, repeatedly boiling and washing the filter cake with DMF for several times, and filtering to obtain 60.36g of light yellow solid with purity of 99% and yield of 79%.
Product MS (m/e): 764; elemental analysis (C)56H32N2O2): theoretical value C: 87.94%, H: 3.66%, N: 3.66%, O: 4.18 percent; found value C: 87.93%, H: 3.67%, N: 3.66%, O: 4.18 percent.
Example 5
Figure GDA0002988250860000141
Synthesis of (Compound II-1-25)
The synthetic route is as follows:
Figure GDA0002988250860000142
synthesis of Compound II-1-25
A1L three-necked flask is stirred by magnetic force, and added with 40.07g (0.378mol) of sodium carbonate, (76.23 g (purity 99%, 0.21mol) of 9- ([1,1' -biphenyl ] -4-yl) -9H-carbazol-3-yl) boric acid and 100ml of toluene in turn after nitrogen replacement. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 44g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, the temperature being controlled between 75 and 90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, repeatedly boiling and washing the filter cake with DMF for several times, and filtering to obtain 71.45g of light yellow solid with purity of 99% and yield of 78%.
Product MS (m/e): 916; elemental analysis (C)68H40N2O2): theoretical value C: 89.06%, H: 4.40%, N: 3.05%, O: 3.49 percent; found value C: 89.05%, H: 4.41%, N: 3.05%, O: 3.49 percent.
Example 6
Figure GDA0002988250860000143
Synthesis of (Compound II-1-27)
The synthetic route is as follows:
Figure GDA0002988250860000151
synthesis of Compound II-1-27
A1L three-necked flask is stirred by magnetic force, and added with 40.07g (0.378mol) of sodium carbonate, (76.23 g (purity 99%, 0.21mol) of 9- ([1,1' -biphenyl ] -3-yl) -9H-carbazol-3-yl) boric acid and 100ml of toluene in turn after nitrogen replacement. After nitrogen replacement, 0.5g of Pd132 was added in this order. After the addition, the temperature was raised to 80 ℃. A solution consisting of 44g of compound P1 (purity 99%, 0.1mol) and 100ml of toluene was initially added dropwise, the temperature being controlled between 75 and 90 ℃. Cooling to room temperature, adding 100ml deionized water for hydrolysis, stirring for 10 min, filtering, repeatedly boiling and washing the filter cake with DMF for several times, and filtering to obtain 71.45g of light yellow solid with purity of 99% and yield of 78%.
Product MS (m-e) The method comprises the following steps 916; elemental analysis (C)68H40N2O2): theoretical value C: 89.06 percent; h: 4.40 percent; n: 3.05 percent; o: 3.49 percent; found value C: 89.05 percent; h: 4.41 percent; n: 3.05 percent; o: 3.49 percent.
According to the technical schemes of the examples 1 to 6, the compounds shown in II-1-1 to II-1-44 can be synthesized only by simply replacing the corresponding raw materials without changing any substantial operation.
Preparation of device examples
(1) Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3PP1, evaporating HATCN as a first hole injection layer on the anode layer film in vacuum, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 1 nm; then evaporating a second hole injection layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 40 nm;
Figure GDA0002988250860000152
(3) a layer II-1-4 is evaporated on the hole injection layer film to form a hole transmission layer, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20 nm;
(4) EML is evaporated on the hole transport layer in vacuum and used as a light emitting layer of the device, the EML comprises a main material and a dye material, the evaporation rate of the main material PRH01 is adjusted to be 0.1nm/s by using a multi-source co-evaporation method, and the dye material Ir (piq)2The acac concentration is 5%, and the total film thickness of evaporation plating is 30 nm;
Figure GDA0002988250860000161
(5) continuously evaporating a layer of compound BPhen 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 30 nm;
Figure GDA0002988250860000162
(6) continuously evaporating a layer of LiF on the electron transport layer to be used as an electron injection layer of the device, wherein the thickness of the evaporated film is 0.5 nm;
(7) continuously evaporating a layer of Al on the electron injection layer to be used as a cathode of the device, wherein the thickness of the evaporated film is 150 nm; the OLED device provided by the invention is obtained and is marked as a device OLED-1.
According to the same steps, replacing the compound II-1-4 in the step (3) with the compound prepared in the embodiment 2-6 of the invention to obtain the devices OLED-2-OLED-6 provided by the invention.
According to the same procedure as above, compound II-1-4 in step (3) was replaced with a comparative compound (structure shown below), to give a comparative device OLED-7.
Figure GDA0002988250860000163
The results of the performance tests of the obtained devices OLED-1 to OLED-7 are shown in Table 1.
Table 1: performance test results of OLED-1 to OLED-7
Figure GDA0002988250860000171
From the above results, the current efficiency of the devices OLED-1 to OLED-6 prepared by using the OLED material provided by the present invention is higher, and the operating voltage is significantly lower than that of the device OLED-7 using the comparative compound 1 as the hole transport material under the same brightness condition.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (7)

1. An OLED material, characterized in that it has a structure represented by the general formula II-1':
Figure FDA0002997191810000011
ar is1、Ar2Each independently of the others represents a group having a N-phenylcarbazole parent nucleus or represents a H atom, Ar1、Ar2May be the same or different, and Ar1、Ar2Not H atoms at the same time.
2. The OLED material of claim 1, wherein Ar is Ar1、Ar2Each independently selected from the group consisting of:
Figure FDA0002997191810000012
3. the OLED material of claim 1, wherein the compound is selected from the following specific structures:
Figure FDA0002997191810000021
Figure FDA0002997191810000031
Figure FDA0002997191810000041
Figure FDA0002997191810000051
4. use of the OLED material of any one of claims 1 to 3 in an organic electroluminescent device.
5. Use according to claim 4, wherein the OLED material is used as a hole transport material for a hole transport layer.
6. An organic electroluminescent device, characterized in that the hole transport layer contains the OLED material according to any one of claims 1 to 3.
7. An organic electroluminescent device, comprising a transparent substrate, an anode layer, a hole transport layer made of the OLED material according to any one of claims 1 to 3, an electroluminescent layer, an electron transport layer, an electron injection layer, and a cathode layer in this order from bottom to top.
CN201911194872.5A 2019-11-28 2019-11-28 OLED material and application thereof in organic electroluminescent device Active CN111116602B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201911194872.5A CN111116602B (en) 2019-11-28 2019-11-28 OLED material and application thereof in organic electroluminescent device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201911194872.5A CN111116602B (en) 2019-11-28 2019-11-28 OLED material and application thereof in organic electroluminescent device

Publications (2)

Publication Number Publication Date
CN111116602A CN111116602A (en) 2020-05-08
CN111116602B true CN111116602B (en) 2021-05-14

Family

ID=70497007

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201911194872.5A Active CN111116602B (en) 2019-11-28 2019-11-28 OLED material and application thereof in organic electroluminescent device

Country Status (1)

Country Link
CN (1) CN111116602B (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101490208A (en) * 2006-07-28 2009-07-22 默克专利有限公司 Novel materials for organic electroluminescent devices
CN103087065A (en) * 2011-11-03 2013-05-08 三星显示有限公司 Ovel Heterocyclic Compound, Organic Light-emitting Device Including The Same And Flat Panel Display Device
CN103509032A (en) * 2013-08-06 2014-01-15 中国科学院苏州纳米技术与纳米仿生研究所 Batch green synthesis method of dioxaanthanthrene oxygenated fused ring compound
CN109503457A (en) * 2018-11-03 2019-03-22 浙江大学 Dinaphtho heterocycle small molecule hole transport material, synthetic method and its application

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5470935B2 (en) * 2008-05-26 2014-04-16 ソニー株式会社 Dioxaanthanthrene compound and semiconductor device
JP6016482B2 (en) * 2012-07-03 2016-10-26 キヤノン株式会社 Dibenzoxanthene compound, organic light emitting device, display device, image information processing device, and image forming device
KR102191995B1 (en) * 2013-10-22 2020-12-17 삼성디스플레이 주식회사 Condensed compound and organic light emitting diode comprising the same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101490208A (en) * 2006-07-28 2009-07-22 默克专利有限公司 Novel materials for organic electroluminescent devices
CN103087065A (en) * 2011-11-03 2013-05-08 三星显示有限公司 Ovel Heterocyclic Compound, Organic Light-emitting Device Including The Same And Flat Panel Display Device
CN103509032A (en) * 2013-08-06 2014-01-15 中国科学院苏州纳米技术与纳米仿生研究所 Batch green synthesis method of dioxaanthanthrene oxygenated fused ring compound
CN109503457A (en) * 2018-11-03 2019-03-22 浙江大学 Dinaphtho heterocycle small molecule hole transport material, synthetic method and its application

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Stable peri-Xanthenoxanthene Thin-Film Transistors with Efficient Carrier Injection;Norihito Kobayashi,et al.;《Chem. Mater.》;20090112;第21卷;第552-556页 *
迫呫吨并呫吨的快速合成及其光电性能;宋继国 等;《发光学报》;20060228;第27卷(第1期);第95-99页 *

Also Published As

Publication number Publication date
CN111116602A (en) 2020-05-08

Similar Documents

Publication Publication Date Title
CN111039954A (en) Novel organic material and application thereof in device
CN106220649B (en) Diaryl ketone-based compound and application thereof in organic electroluminescent device
CN107602601B (en) Boron-containing multi-heterocyclic organic compound and application thereof in organic electroluminescent device
CN109694328B (en) Triarylamine compound, preparation method thereof and application thereof in organic electroluminescent device
CN110563746B (en) Novel SO2 spiro-structure-containing compound and application thereof in OLED (organic light emitting diode) device
CN110467626B (en) Novel spiro-structure compound and application thereof in OLED (organic light emitting diode) device
CN106467458B (en) A kind of compound based on diaryl ketone and its application on organic electroluminescence device
CN103183711B (en) A kind of two-triaryl amine replaces phosphine oxygen base Benzophenanthrene compound, intermediate and preparation method and application
CN114560870B (en) Sulfur-containing polycyclic aromatic compound and application thereof
WO2012081541A1 (en) 1, 2, 4, 5-substituted phenyl derivative, production method for same, and organic electroluminescent element
CN111116602B (en) OLED material and application thereof in organic electroluminescent device
CN110511234B (en) Novel heterocyclic spiro-structure compound and application thereof in OLED (organic light emitting diode) device
CN110183361A (en) ' cross ' type thermal activities delayed fluorescence material being constructed and its applying
CN106467530B (en) A kind of compound based on diaryl ketone and its application in OLED device
CN111004248B (en) Novel organic material and application thereof
CN110903296B (en) OLED material and application thereof in device
CN111004249B (en) OLED material and application thereof
CN111004253B (en) OLED material and application thereof
CN111039953A (en) Xanthene organic material and application thereof in devices
CN108059615B (en) Organic material and application thereof in organic electroluminescent device
CN110511232B (en) Electron transport material and application thereof in device
CN111039955A (en) OLED material and application thereof in organic electroluminescent device
CN110903302A (en) Xanthene OLED material and synthetic method and application thereof
CN111087407A (en) OLED material and application thereof
CN109678730A (en) A kind of organic electroluminescent cavitation material and its preparation and application

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