CN112341375B - Application of carbazole diphenylamine N-N coupling derivative in luminescence - Google Patents

Application of carbazole diphenylamine N-N coupling derivative in luminescence Download PDF

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CN112341375B
CN112341375B CN201910730532.3A CN201910730532A CN112341375B CN 112341375 B CN112341375 B CN 112341375B CN 201910730532 A CN201910730532 A CN 201910730532A CN 112341375 B CN112341375 B CN 112341375B
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付红兵
周丹丹
刘鹏
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Abstract

The invention discloses an application of carbazole diphenylamine N-N coupling derivative in luminescence, wherein the structural formula of the carbazole diphenylamine N-N coupling derivative is any one of I-III, wherein R is1、R2、R3And R4Same or different, said R1、R2、R3And R4Each is hydrogen or C1～C60Alkyl, substituted or unsubstituted C1～C60Alkoxy, substituted or unsubstituted C1～C60Etheralkyl, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C10～C60Condensed ring radical, substituted or unsubstituted C5～C60Heterocyclic group, substituted or unsubstituted halogen atom, carbazole diphenylamine of the inventionThe N-N coupling derivative can be used for organic light-emitting devices, particularly as a main material of a light-emitting layer in the organic light-emitting devices, has the advantages of low starting voltage and high light-emitting efficiency, and is superior to the existing common OLED devices.

Description

Application of carbazole diphenylamine N-N coupling derivative in luminescence
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to an application of carbazole diphenylamine N-N coupling derivatives in luminescence.
Background
Since an OLED (Organic Light-Emitting Diode) has characteristics of being Light and thin, saving power, and the like, such a display device has been widely used in an MP3 player since 2003. An OLED refers to a diode in which an organic light emitting material emits light under the action of current or an electric field, and can directly convert electric energy into light energy. The research work of organic electroluminescence began in the 20 th 60 s, but until the year 1987, the Duncong cloud et al of Kodak company adopted the multilayer film structure, and the organic light emitting diode with high quantum efficiency, high luminous efficiency, high brightness and low driving voltage was obtained for the first time. Compared with the traditional light-emitting and displaying technology, the OLED has the advantages of low driving voltage, small volume, light weight, abundant material types and the like, and is easy to realize large-area preparation, wet preparation and preparation of flexible devices.
Under the action of an electric field, electron holes respectively pass through the electrode and the transmission layer and then are combined in the light-emitting layer to form excitons to excite the light-emitting layer to emit light, and the material of the light-emitting layer is particularly important in an OLED device. In general, light-emitting materials should have high luminous efficiency, preferably have electron or hole transport properties or both, be able to be formed into stable and uniform thin films after vacuum evaporation, and have properties such that their HOMO and LOMO energies should be matched with corresponding electrodes. The organic semiconductor material has various types, different structures and performances and can be adjusted through group molecule cutting. Therefore, the search for the development of new light-emitting organic semiconductor materials with more excellent performance has been a goal pursued by those skilled in the art.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide the application of carbazole diphenylamine N-N coupling derivatives in luminescence.
Another object of the present invention is to provide a light-emitting layer, which is one of applications of carbazole diphenylamine N-N coupling derivatives in light emission.
It is another object of the present invention to provide an organic light emitting device which is a form of application of the light emitting layer.
The invention also aims to provide application of the carbazole diphenylamine N-N coupling derivative in reducing the turn-on voltage and improving the luminous efficiency of the organic light-emitting device.
The purpose of the invention is realized by the following technical scheme.
The application of carbazole diphenylamine N-N coupling derivative in luminescence is disclosed, wherein the structural formula of carbazole diphenylamine N-N coupling derivative is any one of I-III, wherein R is1、R2、R3And R4Same or different, said R1、R2、R3And R4Each is hydrogen or C1～C60Alkyl, substituted or unsubstituted C1～C60Alkoxy, substituted or unsubstituted C1～C60Etheralkyl, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C10～C60Condensed ring radical, substituted or unsubstituted C5～C60A heterocyclic group, a substituted or unsubstituted halogen atom,
Figure BDA0002160384350000021
in the above technical solution, R is1、R2、R3And R4Each is hydrogen or C1～C30Alkyl, substituted or unsubstituted C1～C30Alkoxy, substituted or unsubstituted C1～C30Etheralkyl, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C10～C30Condensed ring radical, substituted or unsubstituted C5～C30Heterocyclic group, substituted or unsubstituted halogen atom.
In the technical scheme, the structural formula of the carbazole diphenylamine N-N coupling derivative is one of the following 1-32:
Figure BDA0002160384350000031
Figure BDA0002160384350000041
a light-emitting layer comprising the carbazole diphenylamine N-N coupling-type derivative.
In the above technical solution, the method further comprises: and (3) guest materials.
In the technical scheme, the guest material is FIrpic, and the mass fraction of carbazole diphenylamine N-N coupling derivatives in the light-emitting layer is 4-10%
An organic light-emitting device comprising an anode, a cathode and 1 or more light-emitting layers between the anode and cathode.
In the above technical solution, an electron injection layer and an electron transport layer are disposed between the light emitting layer and the cathode.
In the above technical solution, the electron injection layer is close to the cathode.
In the above technical solution, the material of the electron transport layer is TPBi.
In the above technical solution, the material of the electron injection layer is Liq.
In the above technical solution, a hole transport layer is disposed between the light emitting layer and the anode.
In the above technical solution, the material of the hole transport layer is NPB.
The carbazole diphenylamine N-N coupling derivative is applied to the organic light-emitting device to reduce the starting voltage and improve the light-emitting efficiency.
The carbazole diphenylamine N-N coupling derivative can be used for organic light-emitting devices, particularly as a main material of a light-emitting layer in the organic light-emitting devices, has the advantages of low starting voltage and high light-emitting efficiency, and is superior to the conventional common OLED devices.
Drawings
Fig. 1 is a schematic structural diagram of a device obtained in comparative example and application example.
Detailed Description
The technical scheme of the invention is further explained by combining specific examples.
The carbazole diphenylamine N-N coupling derivative can be prepared through a Suzuki coupling reaction, and the carbazole diphenylamine N-N coupling derivative can be obtained through the following reaction, and the method is cited in an article J.Am.chem.Soc.2018,140,29, 9074-containing 9077.
Figure BDA0002160384350000051
Comparative examples
An ITO glass substrate (Shenzhen south Hunan City science and technology Limited, 6 omega in resistance, 32 multiplied by 0.55mm in size) serving as an anode is sequentially and respectively placed in distilled water, acetone and ethanol for ultrasonic washing for 10min, dried for 2h at 120 ℃, then washed for 5min by a plasma cleaning machine, and placed in an evaporation machine. Firstly, evaporating a 60 nm-thick NPB layer as a hole transport layer at the evaporation rate of 0.05nm/s, and then evaporating mCP/FIrpic as a light-emitting layer, wherein the mCP/FIrpic is a mixture of mCP and FIrpic, the mass fraction of the FIrpic is 4%, the thickness of the light-emitting layer is 20nm, and the evaporation rate is 0.2 nm/s; then evaporating TPBi as an electron transport layer with the thickness of 50nm and the evaporation rate of 0.3 nm/s; finally, evaporating Liq with the thickness of 1.3nm as an electron injection layer, and then evaporating Al with the thickness of 100nm as a cathode at the speed of 0.01nm/s (Liq) and 0.5nm/s (Al), respectively. The structure of the resulting device is shown in fig. 1.
Application examples
An organic light-emitting device comprises an anode, a cathode and 1 light-emitting layer between the anode and the cathode, wherein an electron injection layer and an electron transport layer are arranged between the light-emitting layer and the cathode, and the electron injection layer is close to the cathode. The material of the electron transport layer is TPBi, and the material of the electron injection layer is Liq. A hole transport layer is arranged between the luminescent layer and the anode, and the material of the hole transport layer is NPB.
The specific preparation method of the organic light-emitting device is as follows:
an ITO glass substrate (Shenzhen south Hunan City science and technology Limited, 6 omega in resistance, 32 multiplied by 0.55mm in size) serving as an anode is sequentially and respectively placed in distilled water, acetone and ethanol for ultrasonic washing for 10min, dried for 2h at 120 ℃, then washed for 5min by a plasma cleaning machine, and placed in an evaporation machine. Firstly, evaporating a 60 nm-thick NPB layer as a hole transport layer at the evaporation rate of 0.05nm/s, then evaporating a mixture of carbazole diphenylamine N-N coupled derivatives and FIrpic in compounds 1-32 as a light emitting layer, wherein the thickness of the light emitting layer is 20nm, the evaporation rate is 0.2nm/s, the mass fraction of carbazole diphenylamine N-N coupled derivatives in the mixture of carbazole diphenylamine N-N coupled derivatives and FIrpic is 6%, and the adopted carbazole diphenylamine N-N coupled derivatives are shown in Table 1; then evaporating TPBi to form an electron transport layer with the thickness of 50nm and the speed of 0.3nm/s, finally evaporating Liq with the thickness of 1.3nm to form an electron injection layer, and then evaporating Al with the thickness of 100nm as a cathode with the speeds of 0.01nm/s (Liq) and 0.5nm/s (Al) respectively. The structure of the resulting device is shown in fig. 1.
The compounds referred to in the above examples (all purchased from Cimbalaite opto-electronic technology, Inc. at 99% purity) were as follows:
NPB (N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine);
mCP 1, 3-dicarbazole-9-ylbenzene
TPBi (1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene);
liq ((8-hydroxyquinoline) lithium);
FIrpic is bis (4, 6-difluorophenylpyridine-N, C2) picolinyliridium.
Figure BDA0002160384350000071
The test performance of the light emitting devices prepared in the comparative example and the application example using a luminance meter is shown in the following table:
the testing steps are as follows: the voltage (0-8V) is applied to the device by adopting a Kethely2400 direct current power supply, and meanwhile, the luminance information of the device is tested by adopting a luminance meter.
TABLE 1
Figure BDA0002160384350000072
Figure BDA0002160384350000081
In Table 1, the compound N/FIrpic represents a mixture of the Nth compound (carbazole diphenylamine N-N coupling type derivative) and FIripic. N compounds are as follows (N: the number below the compound):
Figure BDA0002160384350000091
Figure BDA0002160384350000101
the results show that the carbazole diphenylamine N-N coupling derivative is applied to organic light-emitting devices, particularly used as a light-emitting material, has the advantages of low starting voltage and high light-emitting efficiency, and is an organic light-emitting material with good performance.
The invention has been described in an illustrative manner, and it is to be understood that any simple variations, modifications or other equivalent changes which can be made by one skilled in the art without departing from the spirit of the invention fall within the scope of the invention.

Claims (1)

1. An organic light-emitting device is characterized by comprising an anode, a cathode and 1 or more light-emitting layers positioned between the anode and the cathode, wherein the light-emitting layers comprise carbazole diphenylamine N-N coupled derivatives and guest materials, the guest materials are FIrpic, the mass fraction of the carbazole diphenylamine N-N coupled derivatives in the light-emitting layers is 4-10%, an electron injection layer and an electron transport layer are arranged between the light-emitting layers and the cathode, a hole transport layer is arranged between the light-emitting layers and the anode, the electron injection layer is close to the cathode, the electron transport layer is made of TPBi, the electron injection layer is made of Liq, the hole transport layer is made of NPB, and the structural formula of the carbazole diphenylamine N-N coupled derivatives is one of the following 1-28:
Figure FDA0003490443280000011
Figure FDA0003490443280000021
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CN114213314A (en) * 2021-12-31 2022-03-22 维思普新材料（苏州）有限公司 Organic electroluminescent material based on carbazole-9-yl-diphenylamine derivatives and electronic device thereof

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