CN110003019B - High-mobility organic compound with mesitylene as core and application thereof - Google Patents

High-mobility organic compound with mesitylene as core and application thereof Download PDF

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CN110003019B
CN110003019B CN201910279263.3A CN201910279263A CN110003019B CN 110003019 B CN110003019 B CN 110003019B CN 201910279263 A CN201910279263 A CN 201910279263A CN 110003019 B CN110003019 B CN 110003019B
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梁丽
王芳
谢丹丹
吴秀芹
张兆超
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Jiangsu Sunera Technology Co Ltd
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Abstract

The organic compound provided by the invention takes the pyromellitic benzene as the core and is connected with a pyrene branched chain, the organic compound has good thermal stability and higher glass transition temperature, and simultaneously has a proper HOMO energy level, and a device adopting the organic compound provided by the invention can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through structural optimization.

Description

High-mobility organic compound with mesitylene as core and application thereof
Technical Field
The invention relates to the technical field of semiconductors, in particular to an organic compound with high mobility and taking pyromellitic dianhydride as a core and application thereof.
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 like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and various different functional materials are mutually overlapped together according to purposes to form the OLED light-emitting device. When voltage is applied to electrodes at two ends of the OLED light-emitting device and positive and negative charges in the organic layer functional material film layer are acted through an electric field, the positive and negative charges are further compounded in the electron blocking layer, and OLED electroluminescence is generated.
Current research into improving the performance of OLED light emitting devices includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only the innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the photoelectric functional material of the OLED are required to create the functional material of the OLED with higher performance.
In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, etc. are required, and as a host material of an electron blocking layer, good bipolar property, appropriate HOMO/LUMO energy level, etc. are required.
Therefore, aiming at the industrial application requirements of the current OLED device and the requirements of different functional film layers and photoelectric characteristics of the OLED device, a more suitable OLED functional material or material combination with higher performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. In terms of the actual demand of the current OLED display lighting industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and it is very important to develop a higher-performance organic functional material as a material enterprise.
Disclosure of Invention
One of the purposes of the present invention is to provide an organic compound with high mobility, which takes the pyromellitic dianhydride as the core, and has good thermal stability, higher glass transition temperature and appropriate HOMO energy level.
The technical scheme for solving the technical problems is as follows: an organic compound with high mobility taking pyromellitic dianhydride as a core, wherein the structure of the organic compound is shown as a general formula (1):
Figure BDA0002021126380000021
in the general formula (1), Ar 1 -Ar 5 Respectively represent substituted or unsubstituted C 6- C 30 Aryl, substituted or unsubstituted C 2- C 30 A heteroaryl group;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: adamantyl, cyano, fluorine atom, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, carbazolyl, or furanyl;
the hetero atom in the heteroaryl is selected from one or more of nitrogen, oxygen or sulfur.
As a further improvement of the invention, Ar is 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Respectively expressed by a structure represented by a general formula (2), a general formula (3), a general formula (4) or a general formula (5):
Figure BDA0002021126380000022
in the general formula (2), X 1 And X 2 Each independently represents a single bond, O, S, -C (R) 1 R 2 ) -or-NR 3 -, and X 1 And X 2 Is not simultaneously represented as a single bond;
R 1 、R 2 、R 3 are each independently represented by C 1- C 10 Alkyl of (C) 3- C 10 Cycloalkyl of, C 6- C 30 Aryl radical, C 2 -C 30 A heteroaryl group;
in the general formula (2), the general formula (3), the general formula (4), the general formula (5) and the general formula (6), Y represents a nitrogen atom, a carbon atom or C-R 4 Each occurrence of Y, which is the same or different, when bonded to other groups, is represented by C; r 4 Represented by hydrogen atom, halogen atom, cyano group, C 1- C 20 Alkyl of (C) 3- C 20 Cycloalkyl of, C 1- C 20 Alkoxy group of (C) 6- C 30 Aryl radical, C 2 -C 30 A heteroaryl group.
As a further improvement of the invention, Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 At least one of the structures is represented by a general formula (2) or a general formula (3).
As a further improvement of the invention, R 1 、R 2 、R 3 Each independently represents methyl, isopropyl, tert-butyl, adamantyl, phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, carbazolyl, dibenzothienyl, pyridyl, naphthyridinyl, or carbazolinyl; the R is 4 Represented by a hydrogen atom, a fluorine atom, a cyano group, a methoxy group, a methyl group, an isopropyl group, a tert-butyl group, an adamantyl group, a phenyl group, a biphenyl group, a naphthyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spirofluorenyl group, a dibenzofuranyl group, a carbazolyl group, a dibenzothienyl group, a pyridyl group, a naphthyridinyl group or a carbazolinyl group.
As a further improvement of the present invention, the specific structure of the organic compound is represented by any one of the following structures:
Figure BDA0002021126380000031
Figure BDA0002021126380000041
Figure BDA0002021126380000051
Figure BDA0002021126380000061
Figure BDA0002021126380000071
Figure BDA0002021126380000081
Figure BDA0002021126380000091
Figure BDA0002021126380000101
Figure BDA0002021126380000111
Figure BDA0002021126380000112
any one of the above.
Another object of the present invention is to provide a process for producing the above organic compound. The preparation method is simple, has wide market prospect and is suitable for large-scale production.
The technical scheme for solving the technical problems is as follows: a method for preparing an organic compound with a core of benzene, wherein the method comprises the following reaction equation:
Figure BDA0002021126380000121
the preparation method comprises the following steps: a 250mL three-mouth bottle is filled with the intermediate C, the raw material D, the potassium tert-butoxide and the Pd under the atmosphere of introducing nitrogen 2 (dba)3, triphenylphosphine and 150mL solvent toluene, heating and refluxing for 12 hours, sampling a sample point plate, and completely reacting; naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain a target product;
wherein the molar ratio of the raw material D to the intermediate C is (1.0-3.0):1, the molar ratio of the potassium tert-butoxide to the intermediate C is (1-5):1, and Pd 2 (dba) 3 The molar ratio of the intermediate C to the intermediate C is (0.01-0.03):1, and the molar ratio of the triphenylphosphine to the intermediate C is (0.01-0.03): 1; the amount of toluene used was (100-150) mL of toluene per 1mol of intermediate C.
A third aspect of the present invention provides an organic electroluminescent device comprising a cathode and an anode with an organic functional layer interposed therebetween, characterized in that the organic functional layer contains the above-mentioned organic compound.
As a further improvement of the present invention, the organic functional layer includes a hole transport layer or an electron blocking layer, and has a feature that the hole transport layer or the electron blocking layer contains the organic compound.
A fifth aspect of the present invention is to provide a lighting or display element having such a feature, including the organic electroluminescent device described above.
The beneficial technical effects of the invention are as follows:
1. the structure of the organic compound enables the distribution of electrons and holes in the electron blocking layer to be more balanced, and under the proper HOMO energy level, the hole injection and transmission performance is improved; under a proper LUMO energy level, the organic electroluminescent material plays a role in blocking electrons, and improves the recombination efficiency of excitons in an electron blocking layer; when the material is used as an electron blocking layer material of an OLED light-emitting device, the exciton utilization rate and the fluorescence radiation efficiency can be effectively improved, the efficiency roll-off under high current density is reduced, the voltage of the device is reduced, the current efficiency of the device is improved, and the service life of the device is prolonged.
2. When the organic compound is applied to an OLED device, the structure of the device is optimized, so that high film stability can be kept, and the photoelectric property of the OLED device and the service life of the OLED device can be effectively improved. The compound has good application effect and industrialization prospect in OLED light-emitting devices.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention; the structure comprises a transparent substrate layer 1, a transparent substrate layer 2, an ITO anode layer 3, a hole injection layer 4, a hole transport layer 5, an electron blocking layer 6, an electron blocking layer 7, a hole blocking/electron transport layer 8, an electron injection layer 9, a cathode layer 10 and a CPL layer.
FIG. 2 is a graph of efficiency measured at different temperatures for a device made according to the present invention and a comparative device.
Detailed Description
The technical solution in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention.
All the raw materials in the following preparation examples were purchased from cigarette Taiwangrun Fine chemical Co., Ltd.
Figure BDA0002021126380000131
The preparation method comprises the following steps: a250 ml three-necked flask was charged with 0.01mol of A1 as a starting material, 0.014mol of B1 as a starting material, 0.03mol of potassium tert-butoxide, and 1.4X 10 in a nitrogen atmosphere -4 mol Pd 2 (dba) 3 ，1.3×10 -4 Heating triphenylphosphine and 150ml toluene to 100 ℃ for refluxing 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 C1; HPLC purity 98.6%, yield 86.5%; elemental analysis Structure (molecular formula C) 36 H 29 N 3 )：Theoretical value C, 85.85; h, 5.80; n, 8.34; test values are: c, 85.87; h, 5.81; n, 8.34. ESI-MS (M/z) (M +): theoretical value is 503.24, found 503.25.
Intermediate C was prepared by the synthetic method of intermediate C1, wherein the specific structures of starting material a and starting material B are shown in table 1.
TABLE 1
Figure BDA0002021126380000132
Figure BDA0002021126380000141
Figure BDA0002021126380000151
Preparation example 1: synthesis of Compound 1:
Figure BDA0002021126380000152
the preparation method comprises the following steps: a250 ml three-necked flask was charged with 0.01mol of intermediate C1, 0.014mol of raw material D1, 0.03mol of potassium tert-butoxide, and 1.4X 10 under a nitrogen atmosphere -4 mol Pd 2 (dba) 3 ，1.3×10 -4 Heating triphenylphosphine and 150ml toluene to 110 ℃ for refluxing 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 compound 1; HPLC purity 99.2%, yield 89.1%; elemental analysis Structure (molecular formula C) 52 H 37 N 3 ): theoretical value C, 88.73; h, 5.30; n, 5.97; test values: c, 88.74; h, 5.30; and N, 5.97.
ESI-MS (M/z) (M +): theoretical value is 703.30, found 703.32.
The types of reactions involved in the remaining target compounds are the same as those involved in the preparation step of compound 1.
Preparation example 2 Synthesis of Compound 3
Figure BDA0002021126380000153
Preparation example 3 Synthesis of Compound 6
Figure BDA0002021126380000154
Preparation example 4 Synthesis of Compound 7
Figure BDA0002021126380000161
Preparation example 5 Synthesis of Compound 10
Figure BDA0002021126380000162
Preparation example 6 Synthesis of Compound 12
Figure BDA0002021126380000163
Preparation example 7 Synthesis of Compound 15
Figure BDA0002021126380000164
Preparation example 8 Synthesis of Compound 22
Figure BDA0002021126380000165
Preparation example 9 Synthesis of Compound 31
Figure BDA0002021126380000171
Preparation example 10 Synthesis of Compound 37
Figure BDA0002021126380000172
Preparation example 11 Synthesis of Compound 51
Figure BDA0002021126380000173
Preparation example 12 Synthesis of Compound 58
Figure BDA0002021126380000174
Preparation example 13 Synthesis of Compound 74
Figure BDA0002021126380000175
Preparation example 14 Synthesis of Compound 87
Figure BDA0002021126380000176
Preparation example 15 Synthesis of Compound 102
Figure BDA0002021126380000181
The quantities of reactants and catalysts involved in the preparation of the target compounds, as well as the structural characterization of the target compounds obtained, are shown in table 2.
TABLE 2
Figure BDA0002021126380000182
Figure BDA0002021126380000191
Figure BDA0002021126380000201
The organic compound is used in a light-emitting device, has high glass transition temperature (Tg) and triplet energy level (T1), and suitable HOMO and LUMO energy levels, and can be used as a hole transport layer and an electron blocking layer material. The compounds of the present invention were tested for thermal properties, T1 energy level, HOMO energy level, hole mobility and Eg, respectively, and the results are shown in table 3.
TABLE 3
Figure BDA0002021126380000202
Figure BDA0002021126380000211
Note: the triplet energy level T1 was measured by Hitachi F4600 fluorescence spectrometer under the conditions of 2X 10 - 5 A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the highest occupied molecular orbital HOMO energy level is obtained by testing and calculating an ionization energy testing system (IPS-3) and an ultraviolet spectrophotometer (UV), the test is an atmospheric environment, the hole mobility is tested, the material is made into a single-charge device, and the SCLC method is used for measuring; eg energy level: drawing a tangent line based on an ultraviolet spectrophotometry (UV absorption) baseline of the single material film and the rising side of the first absorption peak, and calculating by using the numerical value of the intersection point of the tangent line and the baseline; meanwhile, the geometrical structure can be optimized by using Gaussian16, 6-31G (d) basis set, B3lyp functional and TD-FDT algorithm to calculate the energy levels of HOMO and LUMO, and Eg is | HOMO-LUMO |.
The data in the table show that the compound of the invention has proper HOMO energy level, Eg and higher hole mobility, and is suitable for being used as a hole transport layer and an electron blocking layer material; meanwhile, the compound has higher thermal stability, so that the service life of an OLED device using the compound is prolonged.
The effect of the synthesized compound of the present invention as a hole transport layer and an electron blocking layer in a device is described in detail below by device examples 1 to 37 and comparative example 1. Compared with the device embodiment 1, the device embodiments 2 to 37 and the device comparative example 1 have the same manufacturing process, adopt the same substrate material and electrode material, and keep the film thickness of the electrode material consistent, except that the material of the hole transport layer is changed in the device embodiments 2 to 17; in device examples 18 to 37, the electron blocking layer materials of the devices were changed, and the structures of the devices obtained in the respective examples are shown in table 4.
Device example 1
As shown in fig. 1, a method for manufacturing an electroluminescent device includes the following steps:
the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness of 150nm) is washed, i.e., washed with alkali, washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, HAT-CN having a film thickness of 10nm was deposited by a vacuum deposition apparatus to be used as the hole injection layer 3. Then, compound 1 was evaporated to a thickness of 60nm as a hole transport layer. EB-1 was then evaporated to a thickness of 20nm as an electron blocking layer. And then manufacturing a light emitting layer 6 of the OLED light emitting device, wherein the structure of the light emitting layer 6 comprises GH-1 and GH-2 used as main materials of the OLED light emitting layer 6, GD-1 used as a doping material, the doping proportion of the doping material is 10% by weight, and the thickness of the light emitting layer is 40 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, Mg: an Ag electrode layer, which is used as the cathode layer 9. On the cathode layer 9, 70nm of CP-1 was vacuum-deposited as a CPL layer 10.
The structure of the related prior art material is as follows:
Figure BDA0002021126380000221
after the OLED light emitting device was completed as described above, the anode and cathode were connected by a known driving circuit, and the current efficiency, the light emission spectrum, and the lifetime of the device were measured. The test results of the resulting devices are shown in Table 5.
TABLE 4
Figure BDA0002021126380000231
Figure BDA0002021126380000241
Figure BDA0002021126380000251
TABLE 5
Figure BDA0002021126380000252
Figure BDA0002021126380000261
The device test performance is referred to comparative example 1; the current efficiency is all 10mA/cm 2 Measured under the condition; the life test System is an OLED device life tester developed by LTD and having model number of EAS-62C.
The results in table 5 show that the compound of the present invention can be applied to the fabrication of OLED light emitting devices as a hole transport layer and an electron blocking layer material, and compared with comparative example 1, the efficiency and lifetime of the compound are greatly improved compared with those of known OLED materials, especially the driving lifetime of the device is greatly improved.
Further, the efficiency of the OLED device prepared by the material is stable when the OLED device works at low temperature, the efficiency tests are carried out on the device examples 1, 8 and 18 and the device comparative example 1 at the temperature range of-10-80 ℃, and the obtained results are shown in the table 6 and the figure 2.
TABLE 6
Figure BDA0002021126380000271
As can be seen from the data in table 6, examples 1, 8 and 18 are device structures in which the material of the present invention and the known material are combined, and compared with comparative device 1, the efficiency is high at low temperature, and the efficiency is steadily increased during the temperature increase process.
From the application of the data, the compound has good application effect as a hole transport layer or an electron blocking layer material in an OLED luminescent device, and has good industrialization prospect.

Claims (6)

1. An organic compound with a mesitylene core, wherein the structure of the organic compound is shown as a general formula (1):
Figure FDA0003425987270000011
in the general formula (1), Ar 1 Is represented by a structure shown in a general formula (2), a general formula (4) or a general formula (5);
Ar 2 、Ar 4 respectively represent a structure shown as a general formula (5);
Ar 3 、Ar 5 respectively represent a structure shown in a general formula (2), a general formula (4) or a general formula (5);
Figure FDA0003425987270000012
in the general formula (2), X 1 Is represented by a single bond, X 2 Denoted as O, S, -C (R) 1 R 2 ) -or-NR 3 -；
R 1 、R 2 Each independently represents a methyl group;
R 3 represented by phenyl;
in the general formulas (2) and (4), Y represents a carbon atom or C-R 4 Y represents C when bonded to other groups; r 4 Represented as a hydrogen atom;
in the general formula (5), Y represents a nitrogen atom, a carbon atom or C-R 4 Each occurrence of Y, which is the same or different, when bonded to other groups, is represented by C; r 4 Represented by a hydrogen atom or a phenyl group.
2. The organic compound of claim 1, wherein Ar is Ar 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 At least one of them is represented by the general formula (2).
3. The organic compound according to claim 1, wherein the specific structure of the organic compound is represented by any one of the following structures:
Figure FDA0003425987270000013
Figure FDA0003425987270000021
Figure FDA0003425987270000031
Figure FDA0003425987270000041
Figure FDA0003425987270000042
any one of the above.
4. An organic compound with a mesitylene core, wherein the structure of the organic compound is as follows:
Figure FDA0003425987270000051
5. an organic electroluminescent device comprising a cathode and an anode with an organic functional layer disposed therebetween, characterized in that the organic functional layer comprises an organic compound according to any one of claims 1 to 4.
6. An organic electroluminescent device according to claim 5, wherein the organic functional layer comprises an electron blocking layer or a hole transporting layer, wherein the electron blocking layer or the hole transporting layer contains the organic compound according to any one of claims 1 to 4.
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