CN109004102A - A kind of application of compound - Google Patents
A kind of application of compound Download PDFInfo
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- CN109004102A CN109004102A CN201810598648.1A CN201810598648A CN109004102A CN 109004102 A CN109004102 A CN 109004102A CN 201810598648 A CN201810598648 A CN 201810598648A CN 109004102 A CN109004102 A CN 109004102A
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
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- H—ELECTRICITY
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- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
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- 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
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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- H—ELECTRICITY
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- 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
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- H—ELECTRICITY
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- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- 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
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
Abstract
The present invention provides a kind of application of compound, formula (I) compound represented provided by the invention after preparing organic electroluminescence device, can effectively improve the light extraction efficiency of device as CPL layers.
Description
Technical field
The present invention relates to organic photoelectrical material technical fields, more particularly, to a kind of application of compound.
Background technique
The correlative study of organic electroluminescence device is initiated at the sixties in 19th century, until the end of the eighties OLED just vigorously send out
Exhibition is got up.There is OLED all solid state, low-voltage driving, active to shine, response quickly, wide viewing angle, light-emitting area are big, emission wavelength covers
Cover entire visible region and it is rich in color the advantages that, realizing that panchromatic large-area displays field has very big advantage, becoming
The flat-panel display device of great prospect.The light emission luminance of organic electroluminescence device is proportional to the concentration and exciton of hole and electronics
The probability of recombination product, it is desirable to obtain higher luminous efficiency, not only need hole and electronics that can be efficiently injected into, transmit and
It is compound and hole and electron injection is required to reach balance.Therefore, in organic electroluminescence device, between organic layer and organic layer
It is matched with the energy band of two electrodes extremely important to device recombination luminescence.
In order to optimize the properties with balancing device, people introduce the functional layer of a variety of different roles, such as hole
Implanted layer, hole blocking layer etc..The effect that hole injection layer is added between ito anode and hole transmission layer is mainly manifested in drop
Low interface potential barrier, the Adhering capacity for increasing hole transmission layer and ITO electrode improve its stability and balance electronic and hole note
Enter etc..
Further, since greatly being constrained between the external quantum efficiency and internal quantum efficiency of OLED there are huge gap
The development of OLED, therefore, the light extraction efficiency for how improving OLED also have become a hot topic of research.Ito thin film and glass substrate
The interface of interface and glass substrate and air can be totally reflected, and be accounted for about before being emitted to OLED device to the light of exterior space
The 20% of organic material film EL total amount, it is thin that remaining about 80% light is mainly limited in organic material film, ITO in the form of guided wave
In film and glass substrate, the development and application of OLED are seriously constrained, the total reflection effect in OLED device how is reduced, improves
The performance drawn optically coupling to before device to the ratio of exterior space, and then improve device has played the extensive concern of people.
Summary of the invention
In view of this, technical problem to be solved by the present invention lies in a kind of application of compound is provided, the present invention is provided
Compound can be improved the efficiency of device as the CPL layer material in OLED device.
The present invention provides a kind of formula (I) compounds represented as CPL layers in preparing organic electroluminescence device
Using,
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20
Base；
The A is formula (A-1), formula (A-2) or formula (A-3),
The R1、R2、R3、R4、R5、R6The independent aryl selected from hydrogen, the alkyl of C1~C3 or C6~C10,
Or the R1And R2The condensed ring radical of C10~C20 is formed with the carbon where it.
Preferably, the Ar1Selected from hydrogen, the alkyl of C1~C5, phenyl, C1~C5 alkyl-substituted phenyl, C10~20
The nitrogenous heteroaryl of fused ring aryl or C3~C15.
Preferably, the Ar2Selected from hydrogen, the alkyl of C1~C5, phenyl, the alkyl-substituted phenyl of C1~C5, C10~20
Fused ring aryl or C3~C15 nitrogenous heteroaryl.
/ 4, application according to claim 1, which is characterized in that the Ar1Selected from hydrogen, methyl, ethyl, propyl, just
Butyl, tert-butyl, amyl, trifluoromethyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3-
N-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl,
4- isopropyl phenyl, 4- aminomethyl phenyl, 3,5- 3,5-dimethylphenyl, pyridyl group, pyridazinyl, pyrazinyl, triazine radical or acridinyl.
Preferably, the Ar2Selected from hydrogen, methyl, ethyl, propyl, normal-butyl, tert-butyl, amyl, trifluoromethyl, phenyl,
Anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- methylbenzene
Base, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl, 4- aminomethyl phenyl, 3,5- diformazan
Base phenyl, pyridyl group, pyridazinyl, pyrazinyl, triazine radical or acridinyl.
Preferably, the R1、R2It is independent to be selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthrene
Base, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl
Phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl；
Or the R1And R2Fluorenyl is formed with the carbon where it.
Preferably, the R3、R4、R5、R6It is independent selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl,
Naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4-
Tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl.
Preferably, formula (I) compound represented is formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-5)
Or formula (I-6),
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20
Base.
Preferably, formula (I) compound represented is formula (001)~formula (159),
Compared with prior art, the present invention provides a kind of formula (I) compounds represented as CPL layers is preparing Organic Electricity
Application in electroluminescence device, the experimental results showed that, compound provided by the invention is used as the CPL layer (Cap of OLED device
Layer, light extraction coating) after material, the light extraction efficiency of device can be effectively improved.
Specific embodiment
The present invention provides a kind of formula (I) compounds represented as CPL layers in preparing organic electroluminescence device
Using,
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20
Base；
The A is formula (A-1), formula (A-2) or formula (A-3),
The R1、R2、R3、R4、R5、R6The independent aryl selected from hydrogen, the alkyl of C1~C3 or C6~C10,
Or the R1And R2The condensed ring radical of C10~C20 is formed with the carbon where it.
According to the present invention, the Ar1Selected from hydrogen, the alkyl of C1~C5, phenyl, the alkyl-substituted phenyl of C1~C5, C10~
20 fused ring aryl or the nitrogenous heteroaryl of C3~C15, more preferably hydrogen, methyl, ethyl, propyl, normal-butyl, tert-butyl, penta
Base, trifluoromethyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- are different
Propyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl, 4-
Aminomethyl phenyl, 3,5- 3,5-dimethylphenyl, pyridyl group, pyridazinyl, pyrazinyl, triazine radical or acridinyl；The Ar2Selected from hydrogen, C1
The alkyl-substituted phenyl of alkyl, phenyl, C1~C5, the fused ring aryl of C10~20 or the nitrogenous heteroaryl of C3~C15 of~C5,
More preferably hydrogen, methyl, ethyl, propyl, normal-butyl, tert-butyl, amyl, trifluoromethyl, phenyl, anthryl, naphthalene, phenanthryl, 3-
Tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl,
4- trifluoromethyl, 4- isopropyl phenyl, 4- aminomethyl phenyl, 3,5- 3,5-dimethylphenyl, pyridyl group, is rattled away at 4- n-propyl phenyl
Piperazine base, pyrazinyl, triazine radical or acridinyl.
The R1Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl benzene
Base, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- fluoroform
Base phenyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl；The R2Preferably hydrogen, methyl, ethyl, n-propyl,
Isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl
Phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- methyl
Phenyl；Or the R1And R2Fluorenyl is formed with the carbon where it.
The R3Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl benzene
Base, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- fluoroform
Base phenyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl.
The R4Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl benzene
Base, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- fluoroform
Base phenyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl.
The R5Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl benzene
Base, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- fluoroform
Base phenyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl.
The R6Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl benzene
Base, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- fluoroform
Base phenyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- aminomethyl phenyl.
Specifically, formula (I) compound represented is formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-5)
Or formula (I-6),
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20
Base.
More specifically, formula (I) compound represented is formula (001)~formula (159),
A kind of formula (I) compound represented provided by the invention is as CPL layers in preparing organic electroluminescence device
Using by selecting specific compound provided by the invention to be used as CPL layer (Cap layer, the light extraction covering of OLED device
Layer) after material, the light extraction efficiency of device can be effectively improved.And raw material sources are extensive, have wide prospects for commercial application.
In addition, in the present inventionRepresent the connecting key of group；In-N represent the key can be in any one of aryl
Position.
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common
Technical staff's every other embodiment obtained without making creative work belongs to the model that the present invention protects
It encloses.
Embodiment 1
It is applied to the preparation of OLED device using formula of the present invention (I) compound as CPL layers, wherein the present invention couple
The source of formula (I) compound does not have particular/special requirement, can buy or make by oneself, if when self-control, can be conventional according to this field
It is prepared by technological means.
It includes: substrate 1 that OLED device in the present embodiment, which is top radiation organic EL part structure, and in substrate 1
On successively plating formed reflecting layer 2, anode 3, hole injection layer (HIL) 4, hole transmission layer (HTL) 5, luminescent layer (EML) 6,
Electron transfer layer (ETL) 7, electron injecting layer (EIL) 8, cathode 9 and coating 10.
Wherein, substrate 1 is glass substrate, quartz base plate or flexible macromolecule substrate (plastics or polyimides etc.)；
Reflecting layer 2 can be metallic silver or silver alloy, metal aluminum or aluminum alloy layer, for reflecting the light of incident orientation substrate
Line；
Anode layer 3 can be ITO (tin indium oxide), IZO (indium zinc oxide), high-work-function metal or alloy, C60 etc. organic half
Conductor material；It is able to achieve the purpose of the present invention, is belonged to the scope of protection of the present invention.
Hole injection layer 4 selects 4,4 ', 4 "-three (N-3- methylphenyl-N-phenyl amino) triphenylamines (MTDATA) and 2,
The mixture of 3,5,6- tetrafluoro Kui bismethanes (F4TCNQ), the mass ratio of the two are 25: 1.
Hole transmission layer 5 is N, N '-two-(1- naphthalene)-N, diphenyl -1 N ' -, 1 '-xenyl -4,4 '-diamines (NPB).
Luminescent layer 6 can be feux rouges, green light or blue light.Wherein, the main body RH of feux rouges is Bebq2 (bis- (10- hydroxy benzos
[h] quinoline) beryllium), doping RD be Ir (piq) 2 (acac), the main body GH of green light is CBP (4,4 '-bis- (N- carbazoles) -1,1 '-connection
Benzene), doping GD be Ir (ppy) 3, blue light main body BH be ADN, doping BD be DPAVB ([4- (diformazan aminophenyl) benzene second of Isosorbide-5-Nitrae-two
Alkenyl] benzene),
Electron transfer layer 7 is Bphen.Electron injecting layer 8 can be inorganic alkali metal compounds or organic alkali metal complex.
Preferred as alkali is that inorganic alkali metal compounds are LiF, and organic alkali metal complex is 8-hydroxy-quinoline lithium.
It is as follows specifically to prepare device:
Blue-light device
Substrate 1 is glass substrate, and sputtering sedimentation Ag sputters 10nm's as reflecting layer 2 with a thickness of 150nm on substrate 1
Anode 3 of the ITO as device, and required figure is etched, use O3Plasma treatment 3 minutes.Gained substrate 1 is placed in vacuum
In, by the mixture of the total MTDATA and F4TCNQ for steaming deposition 130nm as hole injection layer (HIL) 4, wherein F4TCNQ weight
Amount is the 4% of MTDATA weight.Then the NPB of 10nm is deposited as hole transmission layer (HTL) 5.Steam the ADN of deposition 30nm altogether again
Mixture with DPAVB is as luminescent layer 6, and wherein the molar ratio of DPAVB and ADN is 1: 20.Then the Bphen for depositing 20nm makees
For electron transfer layer (ETL) 7.The LiF of 1nm is deposited again as electron injecting layer 8.Cathode 9 is the alloy-layer of co-evaporation K and Ag
10nm, wherein K passes through KBH4The mode that (400 DEG C of temperature) is decomposed during vapor deposition is deposited, K and Ag molar ratio is 8: 1, then
Deposit the Ag of 25nm.The compounds of this invention 001 that 30nm is deposited is used as CPL layers.
Green device
It is consistent with the preparation method of blue-light device, the thickness of HIL is only changed to 170nm, the material of luminescent layer is changed to CBP
With the mixture of Ir (ppy) 3, the wherein molar ratio 1: 10 of Ir (ppy) 3 and CBP.
Red device
It is consistent with the preparation method of blue-light device, the thickness of HIL is only changed to 60nm, the material of luminescent layer is changed to
BeBq2With Ir (piq)2(acac) mixture, wherein Ir (piq)2(acac) and BeBq2Molar ratio be 1: 10.
Embodiment 2
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: K and Ag alloy-layer, molar ratio 2: 1 are thick
Degree is 7nm；Ag layers are 25nm；CPL layers prepare red device for the compounds of this invention 037 with a thickness of 50nm.
Embodiment 3
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: Mg and Ag alloy-layer, molar ratio 4: 1 are thick
Degree is 5nm；Ag layers are 20nm；CPL layers are the compounds of this invention 061, with a thickness of 60nm, prepare green device.
Embodiment 4
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: Mg and Ag alloy-layer, molar ratio 6: 1 are thick
Degree is 7nm；Ag layers are 25nm；CPL layers prepare red device for the compounds of this invention 085 with a thickness of 30nm.
Embodiment 5
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: Li and Ag alloy-layer, molar ratio 8: 1 are thick
Degree is 9nm；Ag layers are 30nm；CPL layers are the compounds of this invention 109, with a thickness of 50nm, prepare green device.
Embodiment 6
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: Mg and Ag alloy-layer, molar ratio 4: 1 are thick
Degree is 11nm；Ag layers are 20nm；CPL layers prepare blue-light device for the compounds of this invention 139 with a thickness of 45nm.
Embodiment 7
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: Mg and Ag alloy-layer, molar ratio 4: 1 are thick
Degree is 11nm；Ag layers are 20nm；CPL layers prepare blue-light device for the compounds of this invention 013 with a thickness of 45nm.
Embodiment 8
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: Mg and Ag alloy-layer, molar ratio 4: 1 are thick
Degree is 3nm；Ag layers are 15nm；CPL layers prepare blue-light device for the compounds of this invention 050 with a thickness of 100nm.
Embodiment 9
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: Mg and Ag alloy-layer, molar ratio 4: 1 are thick
Degree is 3nm；Ag layers are 15nm；CPL layers prepare blue-light device for the compounds of this invention 059 with a thickness of 100nm.
Embodiment 10
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: Mg and Ag alloy-layer, molar ratio 6: 1 are thick
Degree is 7nm；Ag layers are 25nm；CPL layers prepare red device for the compounds of this invention 002 with a thickness of 30nm.
Embodiment 11
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: Mg and Ag alloy-layer, molar ratio 6: 1 are thick
Degree is 7nm；Ag layers are 25nm；CPL layers prepare red device for the compounds of this invention 003 with a thickness of 30nm.
Embodiment 12
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: Mg and Ag alloy-layer, molar ratio 6: 1 are thick
Degree is 7nm；Ag layers are 25nm；CPL layers prepare red device for the compounds of this invention 004 with a thickness of 30nm.
13~embodiment of embodiment 16
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: Li and Ag alloy-layer, molar ratio 8: 1 are thick
Degree is 9nm；Ag layers are 30nm；CPL layers are the compounds of this invention 005~008, with a thickness of 50nm, prepare green device.
17~embodiment of embodiment 20
Specific implementation step is unique the difference is that cathode 9 with embodiment 1 are as follows: Mg and Ag alloy-layer, molar ratio 4: 1 are thick
Degree is 3nm；Ag layers are 15nm；CPL layers prepare blue-light device for the compounds of this invention 009~012 with a thickness of 100nm.
Comparative example 1
This comparative example is OLED device preparation embodiment, and specific steps are as described in Example 1, unique the difference is that described
The transparent composite cathode 9 of OLED only includes the alloy-layer of the low workfunction metal and Ag that set gradually, Ag layers, does not include CPL layers, system
Standby red device, green device and blue-light device.
Comparative example 2
OLED device preparation step is with embodiment 1 in this comparative example, the difference is that the cathode 9 is a kind of compound yin of OLED
Pole structure, the OLED composite cathode structure include the alloy-layer of the low workfunction metal and Ag set gradually, Ag layers.Specific step
It is rapid as follows: under vacuum conditions, using hot evaporation technology, Mg/Ag alloy material to be deposited as the alloy-layer, Mg/Ag's rubs
You than be 1: 1, the alloy-layer with a thickness of 10nm；Under vacuum conditions, using hot evaporation technology, in the upper of the alloy-layer
One layer Ag layers of side's vapor deposition, with a thickness of 10nm, prepares red device, green device and blue-light device.
Embodiment 21
The performance for the OLED device that embodiment 2~8 and comparative example 1~2 obtain is tested, the results are shown in Table 1.
Table 1
As can be seen from the above table, the device of same type, electric current of the device provided by the invention than the device in comparative example
Efficiency, brightness service life are more preferable.
The above description of the embodiment is only used to help understand the method for the present invention and its core ideas.It should be pointed out that pair
For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out
Some improvements and modifications, these improvements and modifications also fall within the scope of protection of the claims of the present invention.
Claims (9)
1. a kind of formula (I) compound represented is preparing the application in organic electroluminescence device as CPL layers,
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20；
The A is formula (A-1), formula (A-2) or formula (A-3),
The R1、R2、R3、R4、R5、R6The independent aryl selected from hydrogen, the alkyl of C1~C3 or C6~C10,
Or the R1And R2The condensed ring radical of C10~C20 is formed with the carbon where it.
2. application according to claim 1, which is characterized in that the Ar1Selected from hydrogen, the alkyl of C1~C5, phenyl, C1~
The nitrogenous heteroaryl of the alkyl-substituted phenyl of C5, the fused ring aryl of C10~20 or C3~C15.
3. application according to claim 1, which is characterized in that the Ar2Selected from hydrogen, the alkyl of C1~C5, phenyl, C1~
The nitrogenous heteroaryl of the alkyl-substituted phenyl of C5, the fused ring aryl of C10~20 or C3~C15.
4. application according to claim 1, which is characterized in that the Ar1Selected from hydrogen, methyl, ethyl, propyl, normal-butyl,
Tert-butyl, amyl, trifluoromethyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl
Phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl
Base phenyl, 4- aminomethyl phenyl, 3,5- 3,5-dimethylphenyl, pyridyl group, pyridazinyl, pyrazinyl, triazine radical or acridinyl.
5. application according to claim 1, which is characterized in that the Ar2Selected from hydrogen, methyl, ethyl, propyl, normal-butyl,
Tert-butyl, amyl, trifluoromethyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl
Phenyl, 3- isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl
Base phenyl, 4- aminomethyl phenyl, 3,5- 3,5-dimethylphenyl, pyridyl group, pyridazinyl, pyrazinyl, triazine radical or acridinyl.
6. application according to claim 1, which is characterized in that the R1、R2It is independent to be selected from hydrogen, methyl, ethyl, positive third
Base, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3- isopropyl
Base phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl or 4- first
Base phenyl；
Or the R1And R2Fluorenyl is formed with the carbon where it.
7. application according to claim 1, which is characterized in that the R3、R4、R5、R6It is independent selected from hydrogen, methyl, ethyl,
N-propyl, isopropyl, phenyl, anthryl, naphthalene, phenanthryl, 3- tert-butyl-phenyl, 3- trifluoromethyl, 3- n-propyl phenyl, 3-
Isopropyl phenyl, 3- aminomethyl phenyl, 4- tert-butyl-phenyl, 4- trifluoromethyl, 4- n-propyl phenyl, 4- isopropyl phenyl or
4- aminomethyl phenyl.
8. application according to claim 1, which is characterized in that formula (I) compound represented is formula (I-1), formula (I-
2), formula (I-3), formula (I-4), formula (I-5) or formula (I-6),
Wherein, the Ar1、Ar2The independent heteroaryl selected from hydrogen, the alkyl of C1~C8, the aryl of C6~C25 or C2~C20.
9. application according to claim 1, which is characterized in that formula (I) compound represented is formula (001), formula
(002), formula (003), formula (004), formula (005), formula (006), formula (007), formula (008), formula (009), formula (010), formula
(011), formula (012), formula (013), formula (014), formula (015), formula (016), formula (017), formula (018), formula (019), formula
(020), formula (021), formula (022), formula (023), formula (024), formula (025), formula (026), formula (027), formula (028), formula
(029), formula (030), formula (031), formula (032), formula (033), formula (034), formula (035), formula (036), formula (037), formula
(038), formula (039), formula (040), formula (041), formula (042), formula (043), formula (044), formula (045), formula (046), formula
(047), formula (048), formula (049), formula (050), formula (051), formula (052), formula (053), formula (054), formula (055), formula
(056), formula (037), formula (058), formula (059), formula (060), formula (061), formula (062), formula (033), formula (064), formula
(065), formula (066), formula (067), formula (038), formula (069), formula (070), formula (071), formula (072), formula (073), formula
(074), formula (075), formula (076), formula (077), formula (078), formula (079), formula (080), formula (081), formula (082), formula
(083), formula (084), formula (085), formula (086), formula (087), formula (088), formula (089), formula (090), formula (091), formula
(092), formula (093), formula (094), formula (095), formula (096), formula (097), formula (098), formula (099), formula (100), formula
(101), formula (102), formula (103), formula (104), formula (105), formula (106), formula (107), formula (108), formula (109), formula
(111), formula (111), formula (112), formula (113), formula (114), formula (115), formula (116), formula (117), formula (118), formula
(119), formula (121), formula (121), formula (122), formula (123), formula (124), formula (125), formula (126), formula (127), formula
(128), formula (129), formula (131), formula (131), formula (132), formula (133), formula (134), formula (135), formula (136), formula
(137), formula (138), formula (139), formula (141), formula (141), formula (142), formula (143), formula (144), formula (145), formula
(146), formula (147), formula (148), formula (149), formula (151), formula (151), formula (152), formula (153), formula (154), formula
(155), formula (156), formula (137), formula (158) or formula (159),
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| WO2023200195A1 (en) * | 2022-04-12 | 2023-10-19 | (주)피엔에이치테크 | Organic compound and organic light emitting diode comprising same |
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