CN113461547B - Diamine derivative for organic electroluminescent device - Google Patents

Diamine derivative for organic electroluminescent device Download PDF

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CN113461547B
CN113461547B CN202010243469.3A CN202010243469A CN113461547B CN 113461547 B CN113461547 B CN 113461547B CN 202010243469 A CN202010243469 A CN 202010243469A CN 113461547 B CN113461547 B CN 113461547B
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diamine derivative
organic electroluminescent
electroluminescent device
hole
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CN113461547A (en
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王芳
张兆超
李崇
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Jiangsu Sunera Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
    • C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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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    • 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
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    • C09K2211/1007—Non-condensed systems
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The application relates to a diamine derivative for an organic electroluminescent device, which belongs to the technical field of semiconductors and has a structure shown in a general formula (1); the diamine derivative provided by the application has stronger hole injection capability and better hole transmission performance, can be applied as a hole transmission layer material to effectively reduce the driving voltage and the starting voltage of a device, has excellent film phase stability, and can be applied as a hole transmission layer material to effectively solve the problem of shorter service life caused by unstable film phase in the driving process of the device.

Description

Diamine derivative for organic electroluminescent device
Technical Field
The application relates to the technical field of semiconductors, in particular to a diamine derivative and application thereof in an organic electroluminescent device.
Background
The organic electroluminescent (OLED: organic Light Emission Diodes) device technology can be used for manufacturing novel display products and novel illumination products, is hopeful to replace the existing liquid crystal display and fluorescent lamp illumination, and has wide application prospect. The OLED light-emitting device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, wherein various functional materials are mutually overlapped together according to purposes to jointly form the OLED light-emitting device. When voltage is applied to two end electrodes of the OLED light-emitting device as a current device, positive and negative charges in the organic layer functional material film layer act through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, so that OLED electroluminescence is generated.
The OLED photoelectric functional material film layer forming the OLED device at least comprises more than two layers, and the industrially applied OLED device structure comprises a plurality of film layers such as a hole injection layer, a hole transmission layer, an electron blocking layer, a luminescent layer, a hole blocking layer, an electron transmission layer, an electron injection layer and the like, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transmission material, a luminescent material, an electron transmission material and the like, and the material types and collocation forms have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional materials have stronger selectivity, and the performance of the same materials in the devices with different structures can be completely different.
When the organic OLED device is applied to a display apparatus, the organic OLED device is required to have a long life and high efficiency, particularly, a blue light device (compared to red and green light emitting devices) of a blue pixel region, a driving voltage is high, and a lifetime is short. In order to prolong the service life of blue pixels and reduce driving voltage, the requirements on the film phase stability and the thermal stability of the hole transport materials are enhanced at present.
At present, the hole transmission side is mainly made of aromatic amine compounds, but devices prepared from the materials still have the problems of higher voltage and shorter service life, so that the service life of blue light devices is prolonged, and the problem that the voltage of the devices is reduced is still needed to be overcome.
Disclosure of Invention
In view of the foregoing problems of the prior art, the applicant of the present application provides a diamine derivative for an organic electroluminescent device. The diamine derivative provided by the application has excellent charge transmission performance, good thermal stability and higher glass transition temperature, and meanwhile has a proper HOMO energy level, and the device adopting the diamine derivative provided by the application can effectively reduce the voltage of an OLED device and prolong the service life of the OLED device to a certain extent through structural optimization.
The technical scheme of the application is as follows:
diamine derivative applied to organic electroluminescent devices, wherein the structure of the diamine derivative is shown as a general formula (1):
the R is 1 Represented by phenyl groupsA naphthyl or biphenyl group;
the L represents phenylene;
the L is 1 、L 2 、L 3 Each independently represents a single bond or phenylene;
the R is 2 、R 3 、R 4 Represented independently as a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, and when L 1 、L 2 、L 3 When they are all single bonds, R 2 、R 3 、R 4 Not simultaneously denoted as biphenyl;
the substituent for the substituted naphthyl, biphenyl or terphenyl group is optionally selected from deuterium atom, adamantyl, phenyl or naphthyl.
Preferably, the R 2 、R 4 Are all denoted as naphthyl.
Preferably, the R 2 、R 3 Are all denoted as naphthyl.
Preferably, the R 4 And R is R 3 Represented as the same group.
Preferably, the R 1 Represented by a naphthyl group, R 4 And R is R 3 Represented as the same group.
Preferably, the R 1 Represented by phenyl, R 4 And R is R 3 Represented as the same group.
Further preferably, the specific structure of the diamine derivative is:
any one of them.
An organic electroluminescent device comprising a cathode, an anode and an organic functional layer, said organic functional layer being located between said anode and cathode, said organic functional layer comprising said diamine derivative. Preferably, the organic functional layer includes a hole transport layer containing the diamine derivative.
Further preferably, the organic electroluminescent device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer and an electron transport region, wherein the electron blocking layer is adjacent to the light emitting layer, the hole injection layer comprises a P-doped material and an organic material, the hole transport layer comprises the same organic material as the hole injection layer, and the hole transport layer comprises a diamine derivative shown in a general formula (1).
An illumination or display element comprising said organic electroluminescent device.
Preferably, a full-color display device includes a substrate, a first electrode, an organic functional material layer and a second electrode from bottom to top in sequence, the organic functional material layer includes: a hole transport region located over the first electrode; a light emitting layer on the hole transporting region, the light emitting layer having a red light emitting layer, a green light emitting layer and a blue light emitting layer patterned in a red pixel region, a green pixel region and a blue pixel region, respectively; an electron transport region located over the light emitting layer; the hole transport region sequentially comprises a hole injection layer, a hole transport layer and an electron blocking layer from bottom to top, wherein the hole injection layer comprises a P-type doping material, the red pixel unit, the green pixel unit and the blue pixel unit are provided with the hole injection layer and the hole transport layer which are common, and the hole transport layer and the electron blocking layer are respectively arranged, and the hole transport layer comprises a diamine derivative shown in a general formula (1).
The beneficial technical effects of the application are as follows:
the diamine derivative provided by the application has a proper HOMO energy level, can form a stable CT complex with a P doped material under a low doping proportion, improves hole injection efficiency, and reduces risk of Cross-talk (red, green and blue pixels are Cross-colored due to different starting voltages of the red, green and blue pixels, wherein the starting voltage of the blue pixel is highest, and the risk of starting an adjacent pixel point is caused when the blue pixel is started;
compared with the structure disclosed in patent EP0666298A2, the diamine derivative has more excellent film crystallization stability, and the hole transport material has a thickness of more than 130nm in the TOP device structure, so that the hole transport material is required to have excellent film phase state stability in the device driving process (the film crystallization stability standard is that the film is not crystallized at 85 ℃ for 1000 hours and is not crystallized at 115 ℃ for 200 hours);
the diamine derivative has small reforming energy (energy generated by molecular configuration change and environmental polarization due to electronic state change), so that the compound has excellent hole transport property, and can obviously reduce the voltage of an OLED device when being applied to the device;
the diamine derivative has excellent hole injection capability and excellent hole transmission performance, so that more holes can be injected into the light-emitting layer, the composite region of the light-emitting layer is far away from the EB side, and the long service life of the device is facilitated.
Drawings
Fig. 1 is a schematic structural view of an OLED device to which the present application is applied.
In the figure: 1 is a transparent substrate layer, 2 is an ITO anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is an electron transport or hole blocking layer, 8 is an electron injection layer, 9 is a cathode reflective electrode layer, and 10 is a light extraction layer.
FIG. 2 shows the results of film crystallization experiments of the compound 1 of the present application and the comparative compound.
Detailed Description
The present application will be described in detail below with reference to the drawings and examples.
Example 1: synthesis of Compound 1:
250ml three-necked flask was charged with 0.01mol of raw material A-1,0.012mol of raw material B-1,0.03mol of potassium tert-butoxide, 1X 10 under an atmosphere of nitrogen -4 mol pd 2 (dba) 3 ，1×10 -4 mol triphenylphosphine, 150ml toluene, heating and refluxing for 12 hours, sampling the spot plate, and completely reacting; naturally cooling, filtering, steaming the filtrate, and passing through a silica gel column to obtain an intermediate D-1; elemental analysis structure (molecular formula C) 34 H 24 ClN): theoretical value C,84.72; h,5.02; n,7.35; cl,2.91; test value: c,84.75; h,5.01; n,7.34; cl,2.90.ESI-MS (M/z) (M) + ): theoretical 481.16 and measured 481.32.
250ml three-necked flask was charged with 0.01mol of intermediate D-1,0.012mol of raw material C-1,0.03mol of potassium tert-butoxide, 1X 10 under an atmosphere of nitrogen -4 mol pd 2 (dba) 3 ，1×10 -4 mol triphenylphosphine, 150ml toluene, heating and refluxing for 12 hours, sampling the spot plate, and completely reacting; naturally cooling, filtering, steaming filtrate, and passing through silica gel column to obtain target compound 1; elemental analysis structure (molecular formula C) 56 H 40 N 2 ): theoretical value C,90.78; h,5.44; n,3.78; test value: c,90.75; h,5.42; n,3.77.ESI-MS (M/z) (M) + ): theoretical 740.32 and measured 740.42.
The following compounds (raw materials used were purchased from Midson energy saving Wanchun Co., ltd.) were prepared in the same manner as in example 1, and the synthetic raw materials are shown in Table 1 below;
TABLE 1
The compound of the application is used in a light-emitting device and can be used as a hole transport layer material. The compounds prepared in the above examples of the present application were tested for thermal properties, T1 energy level, HOMO energy level, and mobility, respectively, and the test results are shown in table 2:
TABLE 2
Note that: the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, german fast Co., DSC204F1 differential scanning calorimeter) at a heating rate of 10 ℃/min; the thermal weight loss temperature Td is a temperature at which the weight loss is 1% in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, the nitrogen flow rate is 20mL/min; the triplet state energy level T1 is tested by a Hitachi F4600 fluorescence spectrometer, and the test condition of the material is 2 x 10 -5 A toluene solution of mol/mL; the highest occupied molecular orbital HOMO energy level is measured by an photoelectron spectroscopy (IPS 3) test, wherein the test is an atmospheric environment and a hole mobility test, the material is manufactured into a single-charge device, and the single-charge device is measured by an SCLC method; eg was tested by uv spectroscopy.
As can be seen from the above table data, the compounds of the present application have a wider band gap (Eg), ensuring that the compounds of the present application are not absorbed in the visible light range; the proper HOMO energy level can solve the problem of carrier injection and reduce the device starting voltage; the material has higher mobility, and can obviously reduce the voltage of a device when being applied as a hole transport material. Therefore, after the diamine derivative is applied to the functional layer of the OLED device, the voltage of the device can be effectively reduced.
The effect of the inventive synthetic OLED materials in devices will be described in detail below by means of device examples 1 to 15 and device comparative example 1, device comparative example 2, device comparative example 3. The device examples 2 to 15, the device comparative example 1, the device comparative example 2 and the device comparative example 3 of the present application were identical in the manufacturing process of the device compared with the device example 1, and the same substrate material and electrode material were used, and the film thickness of the electrode material was also kept uniform, except that the hole transport layer material in the device was changed. The structural composition of the devices obtained in each example is shown in table 3, and the performance test results of the devices obtained in each example are shown in table 4.
Device example 1
Transparent substrate layer 1/ITO anode layer 2/hole injection layer 3 (compound 1: P1,3%10 nm)/hole transport layer 4 (compound 1, 120nm thick)/electron blocking layer 5 (EB-1, 10nm thick)/light emitting layer 6 (BH-1 and BD-1 blended in a weight ratio of 97:3, 20nm thick)/hole blocking/electron transport layer 7 (ET-1 and Liq blended in a weight ratio of 1:1, 30nm thick)/electron injection layer 8 (LiF, 1nm thick)/cathode reflective electrode layer 9 (Mg and Ag blended in a weight ratio of 1:9, 16nm thick)/light extraction layer 10 (compound CP-1, 70nm thick).
The preparation process comprises the following steps:
as shown in fig. 1, the transparent substrate layer 1 was washed with an ITO anode layer 2 (film thickness 10 nm), that is, alkali washing, pure water washing, drying, and ultraviolet-ozone washing in this order, to remove organic residues on the transparent ITO surface. On the ITO anode layer 2 after the washing, a compound 1:P1 having a film thickness of 10nm was vapor deposited by a vacuum vapor deposition apparatus, and a P1 doping ratio of 3% was used as the hole injection layer 3. Then, a 120nm thick compound 1 was evaporated as a hole transport layer 4. Subsequently, 10nm thick compound EB-1 was evaporated as an electron blocking layer 5. After the evaporation of the material of the electron blocking layer 5 is completed, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the light emitting layer comprises BH-1 used by the OLED light emitting layer 6 as a main material, BD-1 as a doping material, the doping proportion of the doping material is 3% by weight, and the film thickness of the light emitting layer is 20nm. After the light-emitting layer 6, vacuum evaporation of the electron transport layer materials ET-1 and Liq was continued. The vacuum evaporation film thickness of the material is 30nm, and the layer is a hole blocking/electron transport layer 7. On the hole blocking/electron transporting layer 7, a lithium fluoride (LiF) layer having a film thickness of 1nm, which is an electron injecting layer 8, was formed by a vacuum vapor deposition apparatus. On the electron injection layer 8, mg having a film thickness of 16nm was produced by a vacuum vapor deposition apparatus: an Ag electrode layer, which is used as the cathode reflection electrode layer 9. On the cathode reflection electrode layer 9, 70nm of CP-1 was vacuum deposited, and the light extraction layer 10 was formed.
Device examples 2-15: the procedure of device example 1 was followed, except that the materials of the hole injection layer and the hole transport layer 4 were replaced, the specific device structure was as shown in table 3, and the device performance test was as shown in table 4;
device comparative examples 1-3 were conducted in accordance with the procedure of device example 1, except that the materials of the hole injection layer and the hole transport layer 4 were replaced.
The structural formula of the materials involved in the preparation process is as follows:
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TABLE 3 Table 3
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The detection data of the obtained electroluminescent device are shown in table 4.
TABLE 4 Table 4
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Note that: the life test system is a korean pulse science M600 type OLED device life tester, defining LT95 life as the time consumed when the luminance of an organic electroluminescent device decays to 95% of its initial luminance; the organic electroluminescent devices prepared in examples 1 to 15 and device comparative examples 1 to 4 were evaluated for driving voltage, current efficiency, and color of emitted light (@ 10 mA), and on-luminance voltage using a CS-2000 spectroradiometer measurement unit (manufactured by KONICAMINOLTA).
As can be seen from the results of table 4, the diamine derivative prepared by the present application can be applied to the fabrication of OLED light emitting devices, and compared with the comparative examples of the devices, the device voltage is reduced by more than 0.1V, the lifetime is improved by more than 10%, and the device turn-on voltage is reduced by about 0.04V.
To illustrate the stability of the film phase of the materials of the present application, compound 1 of the present application, a comparative compound was subjected to a film accelerated crystallization experiment: evaporating different materials on alkali-free glass in a vacuum evaporation mode, packaging in a glove box (water oxygen content is less than 0.1 ppm), placing a packaged sample under the condition of (temperature is 85 ℃ and 115 ℃), and observing the surface morphology of the film by a microscope (LEICA, DM8000M and 5 x 10 multiplying power) periodically, wherein the surface morphology of the material is shown in figure 2;
as can be seen from the results of the crystallization experiments of the comparative compounds D1, D2 and D3 of the compound 1 of the present application in FIG. 2, the surface morphology of the thin film of the compound 1 of the present application is unchanged regardless of whether the compound 1 of the present application is subjected to the standing experiment at 85 ℃ or 115 ℃, which indicates that the compound of the present application has excellent film phase stability; d1 compound darkens at 85 ℃ and cracks appear on the surface of the film at 115 ℃ and is no longer a complete film; after the D2 compound is placed at 85 ℃, the film is unchanged, but the crystallization phenomenon appears on the surface after the compound is placed at 115 ℃; d3 compound film has the worst crystallization stability and the surface is cracked after being placed at 85 ℃; from this, it can be judged that the compound of the present application has more excellent film phase stability than D1, D2, D3.

Claims (4)

1. A diamine derivative for an organic electroluminescent device, characterized in that the specific structure of the diamine derivative is:
any one of them.
2. An organic electroluminescent device comprising a cathode, an anode and an organic functional layer, the organic functional layer being located between the anode and the cathode, characterized in that the organic functional layer contains the diamine derivative according to claim 1.
3. The organic electroluminescent device according to claim 2, wherein the organic functional layer comprises a hole transport layer, wherein the hole transport layer contains the diamine derivative according to claim 1.
4. A lighting or display element comprising the organic electroluminescent device as claimed in any one of claims 2 to 3.
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WO2023237073A1 (en) * 2022-06-10 2023-12-14 浙江光昊光电科技有限公司 Aromatic amine organic compound and use thereof in organic electronic device

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CN108929234A (en) * 2018-07-05 2018-12-04 长春海谱润斯科技有限公司 A kind of preparation of aromatic amine derivatives and its organic electroluminescence device
CN109535012A (en) * 2018-12-17 2019-03-29 长春海谱润斯科技有限公司 A kind of organic electroluminescence device
CN109574857A (en) * 2018-11-29 2019-04-05 长春海谱润斯科技有限公司 A kind of organic electroluminescence device aromatic amine compound and its organic electroluminescence device

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CN108929234A (en) * 2018-07-05 2018-12-04 长春海谱润斯科技有限公司 A kind of preparation of aromatic amine derivatives and its organic electroluminescence device
CN109574857A (en) * 2018-11-29 2019-04-05 长春海谱润斯科技有限公司 A kind of organic electroluminescence device aromatic amine compound and its organic electroluminescence device
CN109535012A (en) * 2018-12-17 2019-03-29 长春海谱润斯科技有限公司 A kind of organic electroluminescence device

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