CN110156612B - Organic compound with high mobility and application thereof - Google Patents

Organic compound with high mobility and application thereof Download PDF

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CN110156612B
CN110156612B CN201910536481.0A CN201910536481A CN110156612B CN 110156612 B CN110156612 B CN 110156612B CN 201910536481 A CN201910536481 A CN 201910536481A CN 110156612 B CN110156612 B CN 110156612B
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CN110156612A (en
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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 invention relates to an organic compound with high mobility and application thereof, belonging to the technical field of semiconductors. The organic compound provided by the invention has a structure shown as a general formula (1),
Figure DDA0002101328210000011
the organic compound of the invention has good thermal stabilityThe organic compound device provided by the invention can effectively improve the photoelectric property of the OLED device and the service life of the OLED device through structure optimization.

Description

Organic compound with high mobility and application thereof
Technical Field
The invention relates to the technical field of semiconductors, in particular to an organic compound with high mobility 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 has good thermal stability, higher glass transition temperature and appropriate HOMO level, and a device using the organic compound provided by the present invention can effectively improve the photoelectric performance of an OLED device and the lifetime of the OLED device through structure optimization.
The technical scheme for solving the technical problems is as follows: an organic compound having high mobility, the structure of the organic compound being represented by general formula (1):
Figure BDA0002101328190000011
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;
x represents-O-, -S-, -C (R) 1 )(R 2 ) or-N (R) 3 ) -one of the above;
z is C, N or C-R 4 ；
R 4 Represented by hydrogen atom, protium atom, deuterium atom, tritium atom, halogen, cyano group, C 1 -C 10 Alkyl of (C) 3 -C 10 Cycloalkyl of, C 1 -C 10 Alkoxy, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 2 -C 30 A heteroaryl group;
r represents a structure shown in a general formula (2), a general formula (3) or a general formula (4), the R is connected to the general formula (1) in a ring-merging mode, an asterisk represents a site for ring-merging connection,
m and n represent 0 or 1, and m + n is not less than 1;
Figure BDA0002101328190000021
in the general formulae (3) and (4), X 1 、X 2 And X 3 Respectively represented by-O-, -S-, -C (R) 5 )(R 6 ) or-N (R) 7 ) -one of the above;
R 1 、R 2 、R 3 、R 5 、R 6 、R 7 is represented as C 1 -C 10 Alkyl of (C) 3 -C 10 Cycloalkyl, 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: cyano radicals, halogen atoms, 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;
the heteroatom in the heteroaryl is one or more selected from nitrogen, oxygen or sulfur.
As a further improvement of the present invention, the general formula (1) is represented by a structure represented by general formula (1-1) or general formula (1-2):
Figure BDA0002101328190000022
as a further improvement of the invention, ar is 1 、Ar 2 、Ar 3 、Ar 4 、Ar 5 Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted naphthyridinyl; the R is 1 、R 2 、R 3 、R 5 、R 6 、R 7 Each independently represents methyl, isopropyl, tert-butyl, adamantyl, phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, carbazolyl, dibenzothienyl, pyridyl, naphthyridinyl, or carbazolinyl.
The substituent is one or more selected from cyano, fluorine atom, methyl, ethyl, propyl, isopropyl, tertiary butyl, amyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuryl, carbazolyl or furyl.
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 BDA0002101328190000031
Figure BDA0002101328190000041
Figure BDA0002101328190000051
Figure BDA0002101328190000061
Figure BDA0002101328190000071
Figure BDA0002101328190000081
Figure BDA0002101328190000091
Figure BDA0002101328190000101
Figure BDA0002101328190000111
Figure BDA0002101328190000121
Figure BDA0002101328190000131
Figure BDA0002101328190000132
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 producing an organic compound having high mobility, the method involving the reaction equation:
Figure BDA0002101328190000141
the preparation method comprises the following steps: a 250mL three-neck flask, under the atmosphere of introducing nitrogen, adding the intermediate C, the raw material D, potassium tert-butoxide and Pd 2 (dba) 3 Heating and refluxing triphenylphosphine and 150mL solvent toluene 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, 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 is to provide an organic electroluminescent device having such features, comprising an anode layer, a cathode layer, and an organic functional layer between the anode layer and the cathode layer, the organic functional layer containing the organic compound.
As a further improvement of the invention, the organic functional layer comprises an electron blocking layer or a hole transporting layer containing the organic compound
A fourth 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 energy-saving Wangrun Co Ltd.
Synthesis of intermediate C1:
Figure BDA0002101328190000151
the preparation method comprises the following steps: a250 ml three-necked flask was charged with 0.01mol of the raw material A1, 0.014mol of the raw material B1,0.03mol 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, and rotary steaming the filtratePassing through a silica gel column to obtain an intermediate C1; HPLC purity 98.7%, yield 86.8%; 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 503.22.
The intermediate C is prepared by a synthesis method of the intermediate C1, wherein specific structures of a raw material A and a raw material B are shown in a table 1.
TABLE 1
Figure BDA0002101328190000152
Figure BDA0002101328190000161
Preparation example 1: synthesis of Compound 1
Figure BDA0002101328190000162
The preparation method comprises the following steps: a250 ml three-necked flask was charged with 0.01mol of the intermediate C1, 0.014mol of the starting material D1,0.03mol of potassium tert-butoxide, and 1.4X 10 in a nitrogen gas 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) 55 H 43 N 3 ): theoretical value C,88.56; h,5.81; n,5.63; test values are: c,88.57; h,5.82; and N,5.63.ESI-MS (M/z) (M +): theoretical value is 745.35, found 745.32.
The types of reactions involved in the preparation of the remaining target compounds are the same as those involved in the preparation step of compound 1.
Preparation example 2 Synthesis of Compound 6
Figure BDA0002101328190000163
Preparation example 3 Synthesis of Compound 14
Figure BDA0002101328190000171
Preparation example 4 Synthesis of Compound 26
Figure BDA0002101328190000172
Preparation example 5 Synthesis of Compound 102
Figure BDA0002101328190000173
Preparation example 6 Synthesis of Compound 111
Figure BDA0002101328190000174
Preparation example 7 Synthesis of Compound 146
Figure BDA0002101328190000175
Preparation example 8 Synthesis of Compound 197
Figure BDA0002101328190000176
Preparation example 9 Synthesis of Compound 228
Figure BDA0002101328190000181
Preparation example 10 Synthesis of Compound 253
Figure BDA0002101328190000182
Preparation example 11 Synthesis of Compound 254
Figure BDA0002101328190000183
Preparation example 12 Synthesis of Compound 256
Figure BDA0002101328190000184
Preparation example 13 Synthesis of Compound 257
Figure BDA0002101328190000185
Preparation example 14 Synthesis of Compound 258
Figure BDA0002101328190000186
Preparation example 15 Synthesis of Compound 259
Figure BDA0002101328190000191
Preparation example 16 Synthesis of Compound 260
Figure BDA0002101328190000192
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 BDA0002101328190000193
Figure BDA0002101328190000201
Figure BDA0002101328190000211
The organic compound of the present invention is used in a light emitting device, has a high glass transition temperature (Tg) and a triplet level (T1), and suitable HOMO and LUMO levels, and is subjected to thermal performance, T1 level, HOMO level, hole mobility and Eg tests, respectively, with the results shown in table 3.
TABLE 3
Figure BDA0002101328190000212
Figure BDA0002101328190000221
Figure BDA0002101328190000231
Note: the triplet state energy level T1 is tested by an F4600 fluorescence spectrometer of Hitachi, and the test condition of the material is 2X 10 - 5 A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter of Germany Chi-resistant company), and 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: material single film based violetDrawing a tangent line between an external spectrophotometric (UV absorption) baseline and the rising side of a first absorption peak, and calculating by using the numerical value of the intersection of the tangent line and the baseline; meanwhile, the geometrical structure can be optimized by using Gaussian16 software, 6-31G (d) base group, B3lyp functional and TD-FDT algorithm to calculate the energy levels of HOMO and LUMO, and Eg = | 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 compound synthesized according to the present invention as a hole transport layer or an electron blocking layer in a device is described in detail below by device examples 1 to 51 and device comparative example 1. Device examples 2 to 51 and device comparative example 1 were compared with device example 1, and the manufacturing processes of the devices were completely the same, and the same substrate material and electrode material were used, and the film thicknesses of the electrode materials were also kept the same, except that the materials of the hole transport layers were changed in device examples 2 to 25; device examples 26 to 51 were obtained by changing the electron blocking layer material of the devices, 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 150 nm) 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 40nm. 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 15 nm-thick 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 BDA0002101328190000241
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 BDA0002101328190000242
Figure BDA0002101328190000251
Figure BDA0002101328190000261
Figure BDA0002101328190000271
TABLE 5
Figure BDA0002101328190000281
The device test performance is referred to comparative example 1; the current efficiency is all 10mA/cm 2 Measured under the conditions.
The results in table 5 show that the compounds of the present invention are applicable to OLED light emitting device fabrication as hole transport layer and electron blocking layer materials and that the efficiency is much improved over known OLED materials compared to comparative example 1.
Further, the efficiency of the OLED device prepared by the material of the invention is stable when the OLED device works at low temperature, and the results of the efficiency tests of the device examples 1, 15 and 28 and the device comparative example 1 at the temperature range of-10 to 80 ℃ are shown in the table 6 and the figure 2.
TABLE 6
Figure BDA0002101328190000291
As can be seen from the data in table 6, examples 1, 15 and 28 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 data application, the compound has good application effect as a hole transport layer or an electron blocking layer material in an OLED light-emitting device, and has good industrialization prospect.
While the invention has been disclosed by way of examples and preferred embodiments, it is to be understood that the invention is not limited to the disclosed embodiments. On the contrary, it is intended to cover various modifications and similar arrangements as would be apparent to those skilled in the art. The scope of the following claims is, therefore, to be accorded the broadest interpretation so as to encompass all such modifications and similar arrangements.

Claims (5)

1. An organic compound having a structure represented by general formula (1):
Figure FDA0003749701560000011
in the general formula (1), ar 1 -Ar 4 Are each represented by phenyl, ar 5 Represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group;
x represents-O-, -S-or-N (R) 3 ) -one of the above;
z is C or C-R 4 ；
R 4 Represented as a hydrogen atom;
r represents a structure shown in a general formula (2), a general formula (3) or a general formula (4), the R is connected to the general formula (1) in a ring-merging mode, an asterisk represents a site for ring-merging connection,
m and n represent 0 or 1, and m + n =1;
Figure FDA0003749701560000012
in the general formulae (3) and (4), X 1 、X 2 And X 3 Respectively represented by-O-, -S-, -C (R) 5 )(R 6 ) or-N (R) 7 ) -one of the above;
R 5 、R 6 represented as methyl;
R 3 、R 7 represented by phenyl, biphenyl or naphthyl;
by "substituted" is meant that at least one hydrogen atom is replaced by a substituent selected from the group consisting of: one or more of methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl and biphenyl.
2. The organic compound according to claim 1, wherein the general formula (1) is represented by a structure represented by general formula (1-1):
Figure FDA0003749701560000021
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 FDA0003749701560000022
Figure FDA0003749701560000031
Figure FDA0003749701560000041
Figure FDA0003749701560000051
Figure FDA0003749701560000061
Figure FDA0003749701560000071
Figure FDA0003749701560000081
Figure FDA0003749701560000082
any one of the above.
4. An organic electroluminescent device comprising an anode layer, a cathode layer and an organic functional layer, which is located between the anode layer and the cathode layer, characterized in that the organic functional layer comprises an organic compound according to any one of claims 1 to 3.
5. An organic electroluminescent device according to claim 4, 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 3.
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