CN109004102B - Application of compound - Google Patents

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CN109004102B
CN109004102B CN201810598648.1A CN201810598648A CN109004102B CN 109004102 B CN109004102 B CN 109004102B CN 201810598648 A CN201810598648 A CN 201810598648A CN 109004102 B CN109004102 B CN 109004102B
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methylphenyl
propylphenyl
isopropylphenyl
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CN109004102A (en
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王辉
赵贺
毕岩
孙峰
李明
李文军
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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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
    • 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
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the devices
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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

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Abstract

The invention provides application of a compound, and the compound shown in the formula (I) can be used as a CPL layer to effectively improve the light extraction efficiency of an organic electroluminescent device after the organic electroluminescent device is prepared.

Description

Application of compound
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to application of a compound.
Background
The related research of organic electroluminescent devices began in the 60's of the 19 th century, and OLEDs were not developed vigorously until the end of the 80's. The OLED has the advantages of all solid state, low-voltage driving, active light emitting, quick response, wide viewing angle, large light emitting area, light emitting wavelength covering the whole visible light region, rich colors and the like, has great advantages in the field of realizing full-color large-area display, and becomes a flat panel display device with great prospect. The luminance of an organic electroluminescent device is proportional to the product of the concentration of holes and electrons and the recombination probability of excitons, and in order to obtain high luminous efficiency, it is required that not only the holes and the electrons can be effectively injected, transported and recombined, but also the holes and the electrons are required to be injected in balance. Therefore, in the organic electroluminescent device, energy band matching between organic layers and between the organic layers and both electrodes is very important for composite light emission of the device.
In order to optimize and balance the various properties of the device, functional layers with different functions, such as hole injection layers, hole blocking layers, etc., have been introduced. The effect of adding the hole injection layer between the ITO anode and the hole transport layer is mainly shown in the aspects of reducing the interface potential barrier, increasing the adhesion capability of the hole transport layer and the ITO electrode, improving the stability of the hole transport layer, balancing the injection of electrons and holes and the like.
In addition, since there is a great gap between the external quantum efficiency and the internal quantum efficiency of the OLED, the development of the OLED is greatly restricted, and therefore, how to improve the light extraction efficiency of the OLED also becomes a hot point of research. The total reflection can occur at the interface of the ITO film and the glass substrate and the interface of the glass substrate and the air, the light emitted to the front external space of the OLED device accounts for about 20% of the total EL of the organic material film, and the rest about 80% of the light is mainly limited in the organic material film, the ITO film and the glass substrate in a guided wave mode, so that the development and the application of the OLED are seriously restricted, the total reflection effect in the OLED device is reduced, the proportion of the light coupled to the front external space of the device is improved, and the performance of the device is further improved, thereby playing a wide role in people.
Disclosure of Invention
In view of the above, the present invention provides a compound for use as a CPL layer material in an OLED device, which can improve the efficiency of the device.
The invention provides an application of a compound shown as a formula (I) as a CPL layer in preparing an organic electroluminescence device,
Figure BDA0001691547560000021
wherein, Ar is1、Ar2Independently selected from hydrogen, alkyl of C1-C8, aryl of C6-C25 or heteroaryl of C2-C20;
a is a formula (A-1), a formula (A-2) or a formula (A-3),
Figure BDA0001691547560000022
the R is1、R2、R3、R4、R5、R6Independently selected from hydrogen, C1-C3 alkyl or C6-C10 aryl,
or said R is1And R2Forms a C10-C20 condensed ring group with the carbon on which the compound is arranged.
Preferably, Ar is1Selected from hydrogen, C1-C5 alkyl, phenyl, C1-C5 alkyl substituted phenyl, C10-20 condensed ring aryl or C3-C15 nitrogen-containing heteroaryl.
Preferably, Ar is2Selected from hydrogen, C1-C5 alkyl, phenyl, C1-C5 alkyl substituted phenyl, C10-20 condensed ring aryl or C3-C15 nitrogen-containing heteroaryl.
The method according to claim 1Use of, characterized in that said Ar1Selected from the group consisting of hydrogen, methyl, ethyl, propyl, n-butyl, t-butyl, pentyl, trifluoromethyl, phenyl, anthracenyl, naphthyl, phenanthryl, 3-t-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-t-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl, 4-methylphenyl, 3, 5-dimethylphenyl, pyridyl, pyridazinyl, pyrazinyl, triazinyl or acridinyl.
Preferably, Ar is2Selected from the group consisting of hydrogen, methyl, ethyl, propyl, n-butyl, t-butyl, pentyl, trifluoromethyl, phenyl, anthracenyl, naphthyl, phenanthryl, 3-t-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-t-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl, 4-methylphenyl, 3, 5-dimethylphenyl, pyridyl, pyridazinyl, pyrazinyl, triazinyl or acridinyl.
Preferably, said R is1、R2Independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl or 4-methylphenyl;
or said R is1And R2Form a fluorenyl group with the carbon on which it is located.
Preferably, said R is3、R4、R5、R6Independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl or 4-methylphenyl.
Preferably, the compound shown in the formula (I) is a compound shown in a formula (I-1), a formula (I-2), a formula (I-3), a formula (I-4), a formula (I-5) or a formula (I-6),
Figure BDA0001691547560000031
wherein, Ar is1、Ar2Independently selected from hydrogen, alkyl of C1-C8, aryl of C6-C25 or heteroaryl of C2-C20.
Preferably, the compound represented by the formula (I) is a compound represented by the formulae (001) to (159),
Figure BDA0001691547560000041
Figure BDA0001691547560000051
Figure BDA0001691547560000061
Figure BDA0001691547560000071
Figure BDA0001691547560000081
Figure BDA0001691547560000091
Figure BDA0001691547560000101
Figure BDA0001691547560000111
Figure BDA0001691547560000121
Figure BDA0001691547560000131
Figure BDA0001691547560000141
Figure BDA0001691547560000151
compared with the prior art, the invention provides the application of the compound shown in the formula (I) as a CPL layer in the preparation of an organic electroluminescent device, and experimental results show that the compound provided by the invention can effectively improve the light extraction efficiency of the device after being used as a CPL layer (Calayer) material of an OLED device.
Detailed Description
The invention provides an application of a compound shown as a formula (I) as a CPL layer in preparing an organic electroluminescence device,
Figure BDA0001691547560000161
wherein, Ar is1、Ar2Independently selected from hydrogen, alkyl of C1-C8, aryl of C6-C25 or heteroaryl of C2-C20;
a is a formula (A-1), a formula (A-2) or a formula (A-3),
Figure BDA0001691547560000162
the R is1、R2、R3、R4、R5、R6Independently selected from hydrogen, C1-C3 alkyl or C6-C10 aryl,
or said R is1And R2Forms a C10-C20 condensed ring group with the carbon on which the compound is arranged.
According to the invention, said Ar1Selected from hydrogen, C1-C5 alkyl, phenyl, C1-C5 alkyl substituted phenyl, C10-20 condensed ring aryl or C3-C15 nitrogen-containing heteroaryl, more preferably hydrogen, methyl, ethyl, propyl, n-butyl, tert-butyl, pentyl, trifluoroMethyl, phenyl, anthracenyl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl, 4-methylphenyl, 3, 5-dimethylphenyl, pyridyl, pyridazinyl, pyrazinyl, triazinyl or acridinyl; ar is2Selected from hydrogen, C1-C5 alkyl, phenyl, C1-C5 alkyl-substituted phenyl, C10-20 fused ring aryl or C3-C15 nitrogen-containing heteroaryl, more preferably hydrogen, methyl, ethyl, propyl, n-butyl, tert-butyl, pentyl, trifluoromethyl, phenyl, anthryl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl, 4-methylphenyl, 3, 5-dimethylphenyl, pyridyl, pyridazinyl, pyrazinyl, triazinyl or acridinyl.
The R is1Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl or 4-methylphenyl; the R is2Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl or 4-methylphenyl; or said R is1And R2Form a fluorenyl group with the carbon on which it is located.
The R is3Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl or 4-methylphenyl.
The R is4Preferably hydrogen, methyl,Ethyl, n-propyl, isopropyl, phenyl, anthracyl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl or 4-methylphenyl.
The R is5Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl or 4-methylphenyl.
The R is6Preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl or 4-methylphenyl.
Specifically, the compound shown in the formula (I) is shown in a formula (I-1), a formula (I-2), a formula (I-3), a formula (I-4), a formula (I-5) or a formula (I-6),
Figure BDA0001691547560000171
Figure BDA0001691547560000181
wherein, Ar is1、Ar2Independently selected from hydrogen, alkyl of C1-C8, aryl of C6-C25 or heteroaryl of C2-C20.
More specifically, the compounds represented by the formula (I) are represented by the formulae (001) to (159),
Figure BDA0001691547560000182
Figure BDA0001691547560000191
Figure BDA0001691547560000201
Figure BDA0001691547560000211
Figure BDA0001691547560000221
Figure BDA0001691547560000231
Figure BDA0001691547560000241
Figure BDA0001691547560000251
Figure BDA0001691547560000261
Figure BDA0001691547560000271
Figure BDA0001691547560000281
Figure BDA0001691547560000291
Figure BDA0001691547560000301
the compound shown in the formula (I) is used as a CPL layer in the preparation of an organic electroluminescence device, and the light extraction efficiency of the device can be effectively improved by selecting the specific compound provided by the invention as a CPL layer (Cap layer) material of an OLED device. And the raw materials are wide in source, and have wide industrial application prospect.
In addition, the present invention
Figure BDA0001691547560000303
A linkage representing a group;
Figure BDA0001691547560000302
wherein-N represents that the bond may be at any position of the aryl group.
The following will clearly and completely describe the technical solutions of the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The compound of formula (I) according to the present invention is applied to the preparation of OLED devices as CPL layer, wherein the present invention has no special requirement for the source of the compound of formula (I), and can be purchased or made by oneself, and if made by oneself, can be prepared according to the conventional technical means in the art.
The structure of the OLED device in this embodiment, which is a top-emission organic electroluminescent device, includes: the organic light emitting diode comprises a substrate 1, and a reflecting layer 2, an anode 3, a Hole Injection Layer (HIL)4, a Hole Transport Layer (HTL)5, an emitting layer (EML)6, an Electron Transport Layer (ETL)7, an Electron Injection Layer (EIL)8, a cathode 9 and a covering layer 10 which are sequentially formed on the substrate 1 in a plating mode.
Wherein, the substrate 1 is a glass substrate, a quartz substrate or a flexible polymer substrate (plastic or polyimide, etc.);
the reflecting layer 2 can be a metal silver or silver alloy layer, a metal aluminum or aluminum alloy layer and is used for reflecting light rays incident to the substrate direction;
the anode layer 3 may be an organic semiconductor material such as ITO (indium tin oxide), IZO (indium zinc oxide), a high work function metal or alloy, C60, or the like; all can achieve the aim of the invention and belong to the protection scope of the invention.
The hole injection layer 4 is a mixture of 4, 4' -tris (N-3-methylphenyl-N-phenylamino) triphenylamine (MTDATA) and 2, 3, 5, 6-tetrafluorotetracyanoquinodimethane (F4TCNQ) in a mass ratio of 25: 1.
The hole transport layer 5 is N, N '-di- (1-naphthyl) -N, N' -diphenyl-1, 1 '-biphenyl-4, 4' -diamine (NPB).
The light emitting layer 6 may be red, green or blue light. Wherein, the main body RH of red light is Bebq2 (bis (10-hydroxybenzo [ h ] quinoline) beryllium), the doped RD is Ir (piq)2(acac), the main body GH of green light is CBP (4, 4 '-bis (N-carbazole) -1, 1' -biphenyl), the doped GD is Ir (ppy)3, the main body BH of blue light is ADN, the doped BD is DPAVB (1, 4-bis [4- (dimethylamino phenyl) styryl ] benzene),
the electron transport layer 7 is Bphen. The electron injection layer 8 may be an inorganic alkali metal compound or an organic alkali metal complex. Preferably, the alkali metal is an inorganic alkali metal compound such as LiF, and the organic alkali metal complex is lithium octahydroxyquinoline.
The device is prepared specifically as follows:
blue light device
The substrate 1 is a glass substrate, Ag is sputtered and deposited on the substrate 1 as a reflecting layer 2, the thickness is 150nm, ITO with the thickness of 10nm is sputtered as an anode 3 of the device, a required pattern is etched, and O is used3Plasma treatment was carried out for 3 minutes. The resulting substrate 1 was placed in a vacuum and a mixture of MTDATA and F4TCNQ, where F is 130nm, was deposited as a Hole Injection Layer (HIL)4 by co-evaporation4The weight of TCNQ was 4% of the weight of MTDATA. Followed by deposition of 10nm of NPB as Hole Transport Layer (HTL) 5. A30 nm mixture of ADN and DPAVB was then co-evaporated as the light-emitting layer 6, with a molar ratio of DPAVB to ADN of 1: 20. Then 20nm of Bphen was deposited as Electron Transport Layer (ETL) 7. Then, LiF of 1nm was evaporated as an electron injection layer 8. The cathode 9 is an alloy layer of K and Ag which are evaporated together by 10nm, wherein K passes through KBH4The deposition was carried out in a decomposition mode during the deposition (temperature 400 ℃ C.) with a molar ratio of K to Ag of 8: 1, followed by the deposition of 25nm of Ag. A 30nm layer of compound 001 of the invention was evaporated as a CPL layer.
Figure BDA0001691547560000321
Green light device
In accordance with the preparation method of the blue light device, the thickness of HIL is changed to 170nm, the material of the light emitting layer is changed to a mixture of CBP and Ir (ppy)3, wherein the molar ratio of Ir (ppy)3 to CBP is 1: 10.
Figure BDA0001691547560000322
Red light device
The method is the same as the preparation method of a blue light device, except that the thickness of the HIL is changed to 60nm, and the material of the luminescent layer is changed to BeBq2And Ir (piq)2(acac) mixtures of Ir (piq)2(acac) with BeBq2The molar ratio of (A) to (B) is 1: 10.
Figure BDA0001691547560000323
Example 2
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: k and Ag alloy layers with the molar ratio of 2: 1 and the thickness of 7 nm; the Ag layer is 25 nm; the CPL layer is the compound 037 of the invention, the thickness is 50nm, and a red light device is prepared.
Example 3
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: an Mg and Ag alloy layer with the molar ratio of 4: 1 and the thickness of 5 nm; the Ag layer is 20 nm; the CPL layer is the compound 061 of the invention, the thickness is 60nm, and a green light device is prepared.
Example 4
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: mg and Ag alloy layers with the mol ratio of 6: 1 and the thickness of 7 nm; the Ag layer is 25 nm; the CPL layer is the compound 085 of the invention, the thickness is 30nm, and a red light device is prepared.
Example 5
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: an Li and Ag alloy layer with the molar ratio of 8: 1 and the thickness of 9 nm; the Ag layer is 30 nm; the CPL layer is the compound 109 of the invention, the thickness is 50nm, and a green light device is prepared.
Example 6
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: an Mg and Ag alloy layer with the molar ratio of 4: 1 and the thickness of 11 nm; the Ag layer is 20 nm; the CPL layer is the compound 139 of the invention, the thickness is 45nm, and the blue light device is prepared.
Example 7
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: an Mg and Ag alloy layer with the molar ratio of 4: 1 and the thickness of 11 nm; the Ag layer is 20 nm; the CPL layer is the compound 013, the thickness is 45nm, and a blue light device is prepared.
Example 8
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: an Mg and Ag alloy layer with the mol ratio of 4: 1 and the thickness of 3 nm; the Ag layer is 15 nm; the CPL layer is the compound 050 of the invention, the thickness is 100nm, and a blue light device is prepared.
Example 9
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: an Mg and Ag alloy layer with the mol ratio of 4: 1 and the thickness of 3 nm; the Ag layer is 15 nm; the CPL layer is the compound 059 of the invention, the thickness is 100nm, prepare the blue light device.
Example 10
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: mg and Ag alloy layers with the mol ratio of 6: 1 and the thickness of 7 nm; the Ag layer is 25 nm; the CPL layer is the compound 002 of the invention, the thickness is 30nm, and the red light device is prepared.
Example 11
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: mg and Ag alloy layers with the mol ratio of 6: 1 and the thickness of 7 nm; the Ag layer is 25 nm; the CPL layer is the compound 003 of the invention, the thickness is 30nm, and the red light device is prepared.
Example 12
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: mg and Ag alloy layers with the mol ratio of 6: 1 and the thickness of 7 nm; the Ag layer is 25 nm; the CPL layer is the compound 004 of the invention, the thickness is 30nm, and the red light device is prepared.
Examples 13 to 16
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: an Li and Ag alloy layer with the molar ratio of 8: 1 and the thickness of 9 nm; the Ag layer is 30 nm; the CPL layer is 005-008 of the compound of the invention, has the thickness of 50nm, and is used for preparing a green light device.
Examples 17 to 20
The specific implementation steps are the same as those in example 1, except that the cathode 9 is: an Mg and Ag alloy layer with the mol ratio of 4: 1 and the thickness of 3 nm; the Ag layer is 15 nm; the CPL layer is a compound 009-012 of the invention, the thickness is 100nm, and a blue light device is prepared.
Comparative example 1
The comparative example is an OLED device preparation example, and specific steps are as described in example 1, except that the OLED transparent composite cathode 9 only includes an alloy layer of a low work function metal and Ag, an Ag layer, and a CPL layer, which are sequentially disposed, and a red light device, a green light device, and a blue light device are prepared.
Comparative example 2
The preparation steps of the OLED device in this comparative example are the same as those in example 1, except that the cathode 9 is an OLED composite cathode structure including an alloy layer of a low work function metal and Ag, and an Ag layer, which are sequentially disposed. The method comprises the following specific steps: under the vacuum condition, utilizing a thermal evaporation technology to evaporate and coat Mg/Ag alloy material as the alloy layer, wherein the molar ratio of Mg/Ag is 1: 1, and the thickness of the alloy layer is 10 nm; and (3) evaporating an Ag layer with the thickness of 10nm above the alloy layer by using a thermal evaporation technology under a vacuum condition to prepare a red light device, a green light device and a blue light device.
Example 21
The performance of the OLED devices obtained in examples 2-8 and comparative examples 1-2 was tested, and the results are shown in Table 1.
TABLE 1
Figure BDA0001691547560000341
Figure BDA0001691547560000351
As can be seen from the above table, the current efficiency and the luminance lifetime of the device provided by the present invention are better than those of the device in the comparative example for the same type of device.
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.

Claims (7)

1. The use of a compound of formula (I) as a CPL layer in the preparation of an organic electroluminescent device,
Figure FDA0002578642460000011
wherein, Ar is1、Ar2Independently selected from hydrogen, C1-C5 alkyl, phenyl, C1-C5 alkyl substituted phenyl, C10-20 condensed ring aryl or C3-C15 nitrogen-containing heteroaryl;
a is a formula (A-1), a formula (A-2) or a formula (A-3),
Figure FDA0002578642460000012
the R is1、R2、R3、R4、R5、R6Independently selected from hydrogen, C1-C3 alkyl or C6-C10 aryl,
or said R is1And R2Forms a C10-C20 condensed ring group with the carbon on which the compound is arranged.
2. Use according to claim 1, wherein said Ar is1Is selected fromHydrogen, methyl, ethyl, propyl, n-butyl, tert-butyl, pentyl, trifluoromethyl, phenyl, anthracenyl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl, 4-methylphenyl, 3, 5-dimethylphenyl, pyridyl, pyridazinyl, pyrazinyl, triazinyl or acridinyl.
3. Use according to claim 1, wherein said Ar is2Selected from the group consisting of hydrogen, methyl, ethyl, propyl, n-butyl, t-butyl, pentyl, trifluoromethyl, phenyl, anthracenyl, naphthyl, phenanthryl, 3-t-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-t-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl, 4-methylphenyl, 3, 5-dimethylphenyl, pyridyl, pyridazinyl, pyrazinyl, triazinyl or acridinyl.
4. Use according to claim 1, wherein R is1、R2Independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl or 4-methylphenyl;
or said R is1And R2Form a fluorenyl group with the carbon on which it is located.
5. Use according to claim 1, wherein R is3、R4、R5、R6Independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, phenyl, anthryl, naphthyl, phenanthryl, 3-tert-butylphenyl, 3-trifluoromethylphenyl, 3-n-propylphenyl, 3-isopropylphenyl, 3-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl or4-methylphenyl radical.
6. The use according to claim 1, wherein the compound of formula (I) is of formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-5) or formula (I-6),
Figure FDA0002578642460000021
Figure FDA0002578642460000031
wherein, Ar is1、Ar2Independently selected from hydrogen, alkyl of C1-C8, aryl of C6-C25 or heteroaryl of C2-C20.
7. The use according to claim 1, wherein the compound of formula (I) is of 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 (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 (085), formula (092), formula (095), formula (093), formula (094), formula (095), formula (094), formula (086), formula (097), formula (094), formula (09, 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 (112), formula (113), formula (114), formula (115), formula (116), formula (117), formula (118), formula (119), formula (121), formula (122), formula (123), formula (124), formula (125), formula (126), formula (127), formula (128), formula (129), formula (131), formula (132), formula (133), formula (134), formula (135), formula (136), formula (137), formula (138), formula (139), formula (141), formula (142), formula (143), formula (144), formula (145), formula (146), formula (147), formula (148), formula (149), or a mixture thereof, Formula (151), formula (152), formula (153), formula (154), formula (155), formula (156), formula (137), formula (158), or formula (159),
Figure FDA0002578642460000041
Figure FDA0002578642460000051
Figure FDA0002578642460000061
Figure FDA0002578642460000071
Figure FDA0002578642460000081
Figure FDA0002578642460000091
Figure FDA0002578642460000101
Figure FDA0002578642460000111
Figure FDA0002578642460000121
Figure FDA0002578642460000131
Figure FDA0002578642460000141
Figure FDA0002578642460000151
Figure FDA0002578642460000161
Figure FDA0002578642460000171
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