CN113461547A - Diamine derivative for organic electroluminescent device - Google Patents

Diamine derivative for organic electroluminescent device Download PDF

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CN113461547A
CN113461547A CN202010243469.3A CN202010243469A CN113461547A CN 113461547 A CN113461547 A CN 113461547A CN 202010243469 A CN202010243469 A CN 202010243469A CN 113461547 A CN113461547 A CN 113461547A
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diamine derivative
layer
hole transport
naphthyl
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CN113461547B (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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    • 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
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    • 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
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    • 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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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K50/00—Organic light-emitting devices
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    • H10K50/14—Carrier transporting layers
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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Abstract

The invention 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 invention has stronger hole injection capability and excellent hole transport performance, can effectively reduce the driving voltage and the starting voltage of a device when being applied as a hole transport layer material, has excellent film phase stability, and can effectively solve the problem of short service life caused by unstable film phase in the driving process of the device when being applied as a hole transport layer material.

Description

Diamine derivative for organic electroluminescent device
Technical Field
The invention relates to the technical field of semiconductors, in particular to a diamine derivative and application thereof in an organic electroluminescent device.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. The OLED light-emitting device is of a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and the various different functional materials are mutually overlapped together according to the application to 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 are acted through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, namely OLED electroluminescence is generated.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, and the OLED device structure applied in industry comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transport material, a light emitting material, an electron transport material and the like, and the material type and the matching form 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 also be completely different.
When the organic OLED device is applied to a display device, the organic OLED device is required to have a long life and a high efficiency, and particularly, a blue device (compared to red and green light emitting devices) of a blue pixel region has a high driving voltage and a short life. In order to prolong the service life of the blue pixel and reduce the driving voltage, the requirements on the film phase stability and the thermal stability of the hole transport material are enhanced at present.
At present, arylamine compounds are mostly adopted at the hole transport side, but the devices prepared by the materials still have the problems of high voltage and short service life, so that the service life of a blue light device is prolonged, and the problem of reducing the voltage of the device still needs to be overcome.
Disclosure of Invention
In view of the above problems of the prior art, the present applicant provides a diamine derivative for use in an organic electroluminescent device. The diamine derivative provided by the invention has excellent charge transfer performance, good thermal stability, higher glass transition temperature and proper HOMO energy level, and the device adopting the diamine derivative can effectively reduce the voltage of an OLED device and prolong the service life of the OLED device to a certain extent through structure optimization.
The technical scheme of the invention is as follows:
a diamine derivative applied to an organic electroluminescent device, wherein the structure of the diamine derivative is shown as a general formula (1):
Figure BDA0002433319160000021
the R is1Represented by phenyl, naphthyl or biphenylyl;
l represents phenylene;
said L1、L2、L3Each independently represents a single bond or phenylene;
the R is2、R3、R4Each independently represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenyl group, and when L is1、L2、L3When all represent a single bond, R2、R3、R4Not simultaneously represented as a biphenylyl group;
the substituent substituted for naphthyl, biphenylyl or terphenyl is optionally selected from deuterium atom, adamantyl, phenyl or naphthyl.
In a preferred embodiment, the R group2、R4Are all represented as naphthyl.
In a preferred embodiment, the R group2、R3Are all represented as naphthyl.
In a preferred embodiment, the R group4And R3Are indicated as the same group.
In a preferred embodiment, the R group1Is represented by naphthyl, R4And R3Are indicated as the same group.
In a preferred embodiment, the R group1Is represented by a phenyl group, and is,R4and R3Are indicated as the same group.
More preferably, the specific structure of the diamine derivative is:
Figure BDA0002433319160000022
Figure BDA0002433319160000031
Figure BDA0002433319160000041
Figure BDA0002433319160000051
any one of the above.
An organic electroluminescent device comprising a cathode, an anode and an organic functional layer, said organic functional layer being located between said anode and said cathode, said organic functional layer comprising said diamine derivative. Preferably, the organic functional layer comprises a hole transport layer containing the diamine derivative.
In a further preferred embodiment, 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 represented by the general formula (1).
A lighting or display element comprising the organic electroluminescent device.
Preferably, a full-color display device, it includes base plate, first electrode, organic functional material layer and second electrode by lower supreme in proper order, organic functional material layer includes: a hole transport region over the first electrode; a light emitting layer on the hole transport 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 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, the hole injection layer comprises a P-type doping material, the red pixel unit, the green pixel unit and the blue pixel unit share the hole injection layer and the hole transport layer and respectively comprise the electron blocking layer, and the hole transport layer comprises diamine derivatives shown in a general formula (1).
The beneficial technical effects of the invention are as follows:
the diamine derivative provided by the invention has a proper HOMO energy level, can form a stable CT complex with a P doping material under a low doping proportion, improves the hole injection efficiency, and reduces Cross-talk risk (red, green and blue pixels are in color crosstalk 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 lighting an adjacent pixel point is generated when the blue pixel is lighted);
compared with the structure disclosed in patent EP0666298A2, the diamine derivative disclosed by the invention has more excellent film crystallization stability, and the hole transport material has a thickness of more than 130nm in the structure of a TOP device, so that the hole transport material is required to have excellent film phase stability in the driving process of the device (the film crystallization stability standard is not crystallized at 85 ℃ for 1000h and not crystallized at 115 ℃ for 200 h);
the diamine derivative has smaller reforming energy (energy generated by molecular configuration change and environmental polarization caused by electronic state change), so that the compound has excellent hole transport performance, and can obviously reduce the voltage of a device when being applied to an OLED device;
the diamine derivative has excellent hole injection capability and hole transmission performance, so that more holes can be injected into the light-emitting layer, the light-emitting layer recombination region is far away from the EB side, and the device has long service life.
Drawings
Fig. 1 is a schematic structural diagram of an OLED device according to the present invention.
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 for compound 1 of the present invention and a comparative compound.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings and examples.
Example 1: synthesis of Compound 1:
Figure BDA0002433319160000061
a250 ml three-necked flask was charged with 0.01mol of the raw material A-1, 0.012mol of the raw material B-1, 0.03mol of potassium tert-butoxide, and 1X 10 in a nitrogen atmosphere-4mol pd2(dba)3，1×10-4Heating and refluxing triphenylphosphine and 150ml toluene for 12 hours, sampling a sample, and completely reacting; naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain an intermediate D-1; elemental analysis Structure (molecular formula C)34H24ClN): theoretical value C, 84.72; h, 5.02; n, 7.35; cl, 2.91; test values are: c, 84.75; h, 5.01; n, 7.34; cl, 2.90. ESI-MS (M/z) (M)+): theoretical value is 481.16, found 481.32.
A250 ml 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 mol under an atmosphere of nitrogen gas-4mol pd2(dba)3，1×10-4Heating and refluxing triphenylphosphine and 150ml toluene for 12 hours, sampling a sample, and completely reacting; naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain a target compound 1; elemental analysis Structure (molecular formula C)56H40N2): theory of thingsTheoretical value C, 90.78; h, 5.44; n, 3.78; test values are: c, 90.75; h, 5.42; n, 3.77. ESI-MS (M/z) (M)+): theoretical value is 740.32, found 740.42.
The following compounds (all raw materials were purchased from Zhongjieyun Wan 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
Figure BDA0002433319160000071
Figure BDA0002433319160000081
The compound of the invention is used in a light-emitting device and can be used as a hole transport layer material. The compounds prepared in the above embodiments of the present invention were tested for thermal performance, T1 energy level, HOMO energy level, and mobility, respectively, and the test results are shown in table 2:
TABLE 2
Figure BDA0002433319160000091
Note: the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the thermogravimetric temperature Td is a temperature at which 1% of the weight loss is observed in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 mL/min; the triplet energy level T1 was measured by Hitachi F4600 fluorescence spectrometer under the conditions of 2X 10-5A toluene solution of mol/mL; the highest occupied molecular orbital HOMO energy level is tested by photoelectron spectroscopy (IPS3) under the atmospheric environment, the hole mobility is tested, the material is made into a single-charge device, and the single-charge device is tested by an SCLC method; eg was tested by uv spectroscopy.
As can be seen from the data in the table above, the compound of the present invention has a wider band gap (Eg), ensuring that the compound of the present invention does not absorb in the visible light field; the appropriate HOMO energy level can solve the problem of carrier injection and reduce the turn-on voltage of the device; the material has higher mobility, and can significantly reduce the voltage of the device when being used as a hole transport material. Therefore, after the diamine derivative is applied to a functional layer of an OLED device, the voltage of the device can be effectively reduced.
The application effect of the synthesized OLED material in the device is explained in detail through device examples 1-15 and device comparative example 1, device comparative example 2 and device comparative example 3. Compared with device example 1, the device examples 2-15, the device comparative example 1, the device comparative example 2 and the device comparative example 3 of the invention have the same manufacturing process, adopt the same substrate material and electrode material, and the film thickness of the electrode material is also kept consistent, except that the hole transport layer material in the device is replaced. The structural composition of the devices obtained in the respective examples is shown in table 3, and the results of the performance tests of the devices obtained in the respective examples 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, thickness 120 nm)/electron blocking layer 5(EB-1, thickness 10 nm)/light emitting layer 6(BH-1 and BD-1 were co-doped in a weight ratio of 97:3, thickness 20 nm)/hole blocking/electron transport layer 7(ET-1 and Liq, co-doped in a weight ratio of 1:1, thickness 30 nm)/electron injection layer 8(LiF, thickness 1 nm)/cathode reflective electrode layer 9(Mg and Ag, co-doped in a weight ratio of 1:9, thickness 16 nm)/light extraction layer 10 (compound CP-1, thickness 70 nm).
The preparation process comprises the following steps:
as shown in FIG. 1, the transparent substrate layer 1 is formed by washing the ITO anode layer 2 (having a film thickness of 10nm), that is, sequentially performing alkali washing, pure water washing, drying, and ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO. On the washed ITO anode layer 2, a compound 1: P1 having a film thickness of 10nm and a doping ratio of P1 of 3% was deposited by a vacuum deposition apparatus to be used as the hole injection layer 3. Then, compound 1 was deposited as a hole transport layer 4 to a thickness of 120 nm. Subsequently, compound EB-1 was evaporated to a thickness of 10nm as an electron blocking layer 5. And after the evaporation of the material of the electron blocking layer 5 is finished, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the OLED light emitting device comprises that BH-1 used by the OLED light emitting layer 6 is used as a main material, BD-1 is used as a doping material, the doping proportion of the doping material is 3% by weight, and the thickness of the light emitting layer is 20 nm. After the light-emitting layer 6, the electron transport layer materials ET-1 and Liq are continuously vacuum-evaporated. The vacuum evaporation film thickness of the material was 30nm, and this layer was a hole-blocking/electron-transporting layer 7. On the hole-blocking/electron-transporting layer 7, a lithium fluoride (LiF) layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron-injecting layer 8. On the electron injection layer 8, a vacuum deposition apparatus was used to produce a 16 nm-thick Mg: an Ag electrode layer, which is used as the cathode reflective electrode layer 9. CP-1 of 70nm was vacuum-deposited on the cathode reflective electrode layer 9, and a light extraction layer 10 was formed.
Device examples 2-15: the process is carried out according to the device example 1, except that the materials of the hole injection layer and the hole transport layer 4 are replaced, the specific device structure is shown in table 3, and the device performance test is shown in table 4;
devices comparative examples 1 to 3 were carried out following 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 material involved in the preparation process is as follows:
Figure BDA0002433319160000111
TABLE 3
Figure BDA0002433319160000112
Figure BDA0002433319160000121
Figure BDA0002433319160000131
The inspection data of the obtained electroluminescent device are shown in Table 4.
TABLE 4
Figure BDA0002433319160000132
Figure BDA0002433319160000141
Note: the life test system is a life tester of an OLED device of Korean pulse science M600 type, and the life of LT95 is defined as the time consumed when the brightness of the organic electroluminescent device is attenuated to 95% of the initial brightness; 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 (@10mA), ignition voltage using a CS-2000 spectroradiometer measuring unit (available from KONICAMINOLTA).
The results in table 4 show that the diamine derivative prepared by the present invention can be applied to the fabrication of OLED light emitting devices, and compared with the comparative device, the voltage of the device is reduced by more than 0.1V, the lifetime is improved by more than 10%, and the turn-on voltage of the device is reduced by about 0.04V.
To illustrate the stability of the phase state of the material film of the present application, compound 1 of the present application, a comparative compound, was subjected to a film accelerated crystallization experiment: different materials are evaporated on alkali-free glass in a vacuum evaporation mode, the alkali-free glass is packaged in a glove box (the water oxygen content is less than 0.1ppm), the packaged sample is placed at the temperature of 85 ℃ and 115 ℃, the surface appearance of the thin film is observed by a microscope (LEICA, DM8000M, 5 x 10 multiplying power) periodically, and the surface appearance of the material is shown in figure 2;
as can be seen from the results of the film crystallization experiments of the compound 1 of the present invention compared with the compounds D1, D2, and D3 in fig. 2, the surface morphology of the compound 1 thin film of the present invention is not changed no matter the compound 1 of the present invention is placed at 85 ℃ or 115 ℃, which indicates that the compound of the present invention has excellent film phase stability; the color of the D1 compound film becomes dark at 85 ℃, and the surface of the film cracks at 115 ℃ and is not a complete film any more; after the D2 compound is placed at 85 ℃ for experiment, the film is not changed, but the surface is crystallized after being placed at 115 ℃; the D3 compound film has the worst crystallization stability, and the surface of the film is cracked after the film is placed at 85 ℃; therefore, the compounds of the present invention can be judged to have more excellent film phase stability compared with D1, D2 and D3.

Claims (10)

1. A diamine derivative for an organic electroluminescent device, characterized in that the diamine derivative has a structure represented by the general formula (1):
Figure FDA0002433319150000011
the R is1Represented by phenyl, naphthyl or biphenylyl;
l represents phenylene;
said L1、L2、L3Each independently represents a single bond or phenylene;
the R is2、R3、R4Each independently represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenyl group, and when L is1、L2、L3When all represent a single bond, R2、R3、R4Not simultaneously represented as a biphenylyl group;
the substituent substituted for naphthyl, biphenylyl or terphenyl is optionally selected from deuterium atom, adamantyl, phenyl or naphthyl.
2. Diamine derivative according to claim 1, characterized in that R is2、R4Are all represented as naphthyl.
3. Diamine derivative according to claim 1, characterized in that R is2、R3Are all represented as naphthyl.
4. Diamine derivative according to claim 1, characterized in that R is4And R3Are indicated as the same group.
5. Diamine derivative according to claim 1, characterized in that R is1Is represented by naphthyl, R4And R3Are indicated as the same group.
6. Diamine derivative according to claim 1, characterized in that R is1Is represented by phenyl, R4And R3Are indicated as the same group.
7. Diamine derivative according to claim 1, characterized in that it has the specific structure:
Figure FDA0002433319150000012
Figure FDA0002433319150000021
Figure FDA0002433319150000031
Figure FDA0002433319150000041
Figure FDA0002433319150000042
any one of the above.
8. 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 as claimed in any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, wherein the organic functional layer comprises a hole transport layer, and wherein the hole transport layer contains the diamine derivative according to any one of claims 1 to 7.
10. A lighting or display element comprising the organic electroluminescent device according to any one of claims 8 to 9.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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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