CN111362959A - Compound with olefinic bond-containing fluorene as core and application thereof - Google Patents

Compound with olefinic bond-containing fluorene as core and application thereof Download PDF

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CN111362959A
CN111362959A CN201811593668.6A CN201811593668A CN111362959A CN 111362959 A CN111362959 A CN 111362959A CN 201811593668 A CN201811593668 A CN 201811593668A CN 111362959 A CN111362959 A CN 111362959A
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李崇
吴秀芹
王芳
张兆超
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Jiangsu Sunera Technology Co Ltd
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Abstract

The invention discloses a compound taking ethylenic fluorene as a core, a preparation method and application thereof, and the structure of the organic compound provided by the invention is shown as a general formula (1). The compound provided by the invention has higher glass transition temperature and molecular thermal stability, proper HOMO and LUMO energy levels and higher Eg, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization. The general formula (1) is specifically shown below:
Figure DDA0001920857530000011

Description

Compound with olefinic bond-containing fluorene as core and application thereof
Technical Field
The invention relates to the technical field of semiconductor materials, in particular to a compound taking ethylenic fluorene as a core, a preparation method thereof 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 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 light-emitting layer, and OLED electroluminescence is generated.
Currently, the OLED display technology is already applied in the fields of smart phones, tablet computers, and the like, and is further expanded to the large-size application field of televisions, and the like, but compared with the actual product application requirements, the performance of the OLED device, such as light emitting efficiency, service life, and the like, needs to be further improved. 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.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two categories from the aspect of application, namely charge injection transmission materials and luminescent materials. Further, the charge injection transport material may be classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the light emitting material may be classified into a host light emitting material and a doping material.
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, as a host material of a light-emitting layer, good bipolar, appropriate HOMO/LUMO energy level, etc. are required.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, the OLED device structure applied in industry comprises a hole injection layer, a hole transmission layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transmission 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 transmission material, a light emitting material, an electron transmission 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 material has stronger selectivity, and the performance of the same material in the devices with different structures can be completely different.
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
In view of the above problems in the prior art, the applicant of the present invention provides a compound with an ethylenic fluorene as a core and an application thereof. The compound takes fluorene containing olefinic bond as a core, has higher glass transition temperature and molecular thermal stability, proper HOMO and LUMO energy levels and higher Eg, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization.
The technical scheme of the invention is as follows: a compound taking ethylenic fluorene as a core is disclosed, and the structure of the compound is shown as a general formula (1):
Figure BDA0001920857510000021
in the general formula (1), the dotted line represents that two groups are linked or not linked by a single bond;
Z、Z1each independently represents a nitrogen atom or C-H; z, Z at the connection site1Represented as a carbon atom;
a. b, c and d are integers which are not less than 0 respectively, and a + b + c + d are not less than 1;
R1、R2、R3、R4each independently represents a hydrogen atom, protium, deuterium, tritium, cyano group, halogen, C1-20Alkyl group of (A) or (B),The structure shown in the general formula (2) or the general formula (3), and at least one of the structures is shown in the general formula (2) or the general formula (3);
Figure BDA0001920857510000031
in the general formulae (2) and (3), Ar1、Ar2Each independently represents a single bond, substituted or unsubstituted C6-30Arylene, 5-30 membered heteroarylene substituted or unsubstituted with one or more heteroatoms;
in the general formula (3), X1Represented by-O-, -S-, -C (R)10)(R11) -or-N (R)12)-；
In the general formula (2) and the general formula (3), R5、R6、R7Each independently represents a hydrogen atom, a structure represented by general formula (4), general formula (5) or general formula (6);
Figure BDA0001920857510000032
in the general formula (4), X2、X3Each independently represents a single bond, -O-, -S-, -C (R)13)(R14) -or-N (R)15) -; and X2、X3Not simultaneously represent a single bond;
in the general formula (5), R8、R9Each independently represents substituted or unsubstituted C6-30Aryl, 5-30 membered heteroaryl, substituted or unsubstituted with one or more heteroatoms;
Y1、Y2、Y3and Y4Each independently represents a nitrogen atom or C (R)16) And at least one of which is represented by N; and connect Y at the site1、Y2、Y3And Y4Represented as a carbon atom;
the two adjacent positions marked by x in the general formula (4) and the general formula (6) are connected with the two adjacent positions marked by x in the general formula (2) or the general formula (3) in a ring-by-ring manner;
the R is10～R15Each independently is represented by C1-20Alkyl, substituted or unsubstituted C6-30Aryl, 5-30 membered heteroaryl, substituted or unsubstituted with one or more heteroatoms; and R is10And R11、R13And R14Do not form a ring or bond to each other to form a ring;
the R is16Expressed as hydrogen atom, protium, deuterium, tritium, cyano, halogen, C1-20Alkyl, substituted or unsubstituted C6-30Aryl, 5-30 membered heteroaryl, substituted or unsubstituted with one or more heteroatoms;
the substituent for the substitution of each of the above groups is optionally selected from protium, deuterium, tritium, cyano, halogen atom, cyano, C1-20Alkyl of (C)6-30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the hetero atom in the heteroarylene group or the heteroaryl group is any one or more selected from N, O or S.
As a further improvement of the invention, a, b, c and d are respectively 0 or 1; the R is1、R2、R3、R4Each independently represents a hydrogen atom, protium, deuterium, tritium, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, a structure represented by general formula (2) or general formula (3), and at least one of the structures is represented by general formula (2) or general formula (3).
Further preferably, R5And R6Not simultaneously represented as a hydrogen atom, R7Not represented as hydrogen atoms.
Further preferably, the dotted line indicates that two groups are connected by a single bond, Z is carbon, and Y is1、Y2、Y3And Y4With only one being represented as a nitrogen atom.
More preferably, the dotted line represents a single bond linking two groups, a + b + c + d being 2, R1、R2、R3Or R4One group is represented by a structure shown in a general formula (2) or a general formula (3), and the other group is tert-butyl.
As a further improvement of the invention, Ar is1、Ar2Are respectively and independentlyRepresents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthyridine group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group;
the R is8、R9Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted 9, 9-diphenylfluorenyl, substituted or unsubstituted 9, 9-spirofluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted phenanthryl and substituted or unsubstituted anthryl;
the R is10～R15Each independently represents one of methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, pentyl, hexyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl and substituted or unsubstituted pyridyl;
the R is16Represented by hydrogen atom, protium, deuterium, tritium, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted biphenyl group;
the substituent when each of the above groups is substituted is optionally one or more selected from protium, deuterium, tritium, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, naphthyl, naphthyridinyl, pyridyl, biphenylyl, terphenylyl, carbazolyl, or dibenzofuranyl.
Further, the general formula (1) is any one of the following specific compounds:
Figure BDA0001920857510000051
Figure BDA0001920857510000061
Figure BDA0001920857510000071
Figure BDA0001920857510000081
Figure BDA0001920857510000091
Figure BDA0001920857510000101
Figure BDA0001920857510000111
Figure BDA0001920857510000121
Figure BDA0001920857510000131
Figure BDA0001920857510000132
any one of the above.
The invention also relates to an organic electroluminescent device, wherein a plurality of organic thin film layers are arranged between an anode and a cathode of the organic electroluminescent device, and at least one organic thin film layer contains the compound taking the ethylenic fluorene as the core.
Further, the multilayer organic thin film layer comprises a light-emitting layer, an electron blocking layer and/or a hole transport layer, and the light-emitting layer, the electron blocking layer and/or the hole transport layer contain the compound with the ethylenic fluorene as a core.
The invention also relates to a lighting or display element comprising said organic electroluminescent device.
The invention also relates to application of the compound taking the ethylenic fluorene as the core in preparing organic electroluminescent devices.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) the compound of the invention takes the ethylenic fluorene as a core, is connected with an electron-donating group, has high triplet state energy level (T1), can effectively prevent exciton energy of a luminescent layer from being transferred to a hole transfer layer when being used as a material of an electron blocking layer and/or the hole transfer layer of an OLED luminescent device, improves the recombination efficiency of excitons in the luminescent layer, improves the energy utilization rate, and thus improves the luminescent efficiency of the device.
(2) The compound of the invention ensures that the distribution of electrons and holes in the luminescent layer is 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 the luminescent layer; the exciton utilization rate and the high fluorescence radiation efficiency can be effectively improved, the voltage of the device is reduced, the current efficiency of the device is improved, and the service life of the device is prolonged; thereby making it easier to obtain high efficiency of the device. The compound has good application effect in OLED luminescent devices and good industrialization prospect.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in 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, a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is an electron transport layer, 8 is an electron injection layer, and 9 is a cathode reflective electrode layer.
Fig. 2 is a graph of the current efficiency of the device of the present invention as a function of temperature.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings and examples.
All the raw materials in the following examples were purchased from cigarette Taiwangrun Fine chemical Co., Ltd.
Example 1 synthesis of compound 3:
Figure BDA0001920857510000141
0.01mol of the raw material A-1 and 0.012mol of the raw material B-1 were dissolved in 150mL of a mixed solution of toluene and ethanol (V toluene: V ethanol: 5: 1), deoxygenated, and then 0.0002mol of Pd (PPh) was added3)4And 0.02mol of K2CO3Reacting at 110 ℃ for 24 hours in the atmosphere of introducing nitrogen, sampling a sample, cooling and filtering after the raw materials react completely, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain a compound 3; elemental analysis Structure (molecular formula C)49H28N2O): theoretical value: c, 89.07; h, 4.27; n, 4.24; o, 2.42; test values are: c, 89.08; h, 4.27; n, 4.24; o, 2.41. ESI-MS (M/z) (M +): theoretical value is 660.78, found 660.75.
Example 2 synthesis of compound 12:
Figure BDA0001920857510000151
compound 12 was prepared as in example 1, except that the starting material A-1 was replaced with the starting material A-2 and the starting material B-1 was replaced with the starting material B-2; elemental analysis Structure (molecular formula C)49H28N2O): theoretical value: c, 89.07; h, 4.27; n, 4.24; o, 2.42; test values are: c, 89.07; h, 4.27; n, 4.25; o, 2.41. ESI-MS (M/z) (M +): theoretical value is 660.78, found 660.75.
Example 3 synthesis of compound 24:
Figure BDA0001920857510000152
compound 24 was prepared in the same manner as in example 1 except that the starting material A-1 was replaced with the starting material A-2 and the starting material B-1 was replaced with the starting material B-3; elemental analysisStructure (molecular formula C)55H33N3): theoretical value: c, 89.77; h, 4.52; n, 5.71; test values are: c, 89.77; h, 4.53; and N, 5.70. ESI-MS (M/z) (M +): theoretical value is 735.89, found 735.80.
Example 4 synthesis of compound 32:
Figure BDA0001920857510000153
a250 ml three-necked flask was charged with 0.01mol of the raw material C-1, 0.012mol of the raw material A-3, 0.03mol of potassium tert-butoxide, 1 × 10 under 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 a compound 32; elemental analysis Structure (molecular formula C)55H33N3): theoretical value: c, 89.77; h, 4.52; n, 5.71; test values are: c, 89.77; h, 4.53; and N, 5.70. ESI-MS (M/z) (M +): theoretical value is 735.89, found 735.81.
Example 5 synthesis of compound 40:
Figure BDA0001920857510000161
compound 40 was prepared as in example 1, except that starting material B-4 was used in place of starting material B-1; elemental analysis Structure (molecular formula C)66H43N5): theoretical value C, 87.49; h, 4.78; n, 7.73; test values are: c, 87.20; h, 4.78; n, 7.73. ESI-MS (M/z) (M +): theoretical value is 906.11, found 906.15.
Example 6 synthesis of compound 49:
Figure BDA0001920857510000162
compound 49 is prepared as in example 1, except that starting material A-3 is used in place of starting material A-1 and starting material B-5 is used in place of starting material B-1; elemental analysis Structure (molecular formula C)55H30N2O2): theoretical value C, 87.98; h, 4.03; n, 3.73; o, 4.26; test values are: c, 87.99; h, 4.03; n, 3.72; and O, 4.26. ESI-MS (M/z) (M +): theoretical value is 750.86, found 750.82.
Example 7 synthesis of compound 61:
Figure BDA0001920857510000171
compound 61 can be prepared by the same method as in example 1, except that starting material A-4 is used instead of starting material A-1, and starting material B-6 is used instead of starting material B-1; elemental analysis Structure (molecular formula C)58H38N2): theoretical value C, 91.31; h, 5.02; n, 3.67; test values are: c, 91.32; h, 5.02; and N, 3.66. ESI-MS (M/z) (M +): theoretical value is 762.96, found 762.90.
Example 8 synthesis of compound 75:
Figure BDA0001920857510000172
compound 75 was prepared as in example 1, except that the starting material A-1 was replaced with starting material A-3 and the starting material B-1 was replaced with starting material B-7; elemental analysis Structure (molecular formula C)61H39N3): theoretical value: c, 90.01; h, 4.83; n, 5.16; test values are: c, 90.01; h, 4.84; and N, 5.16. ESI-MS (M/z) (M +): theoretical value is 814.00, found 814.05.
Example 9 synthesis of compound 86:
Figure BDA0001920857510000173
compound 86 is prepared as in example 1, except that starting material B-8 is used in place of starting material B-1; elemental analysis Structure (molecular formula C)53H28N4O4): theoretical value: c, 89.29; h, 5.20; n, 1.68; o, 3.84; test values are: c, 89.30; h, 5.20; n, 1.68; and O, 3.83. ESI-MS (M/z) (M +): theoretical value is 784.43, found 784.51.
Example 10 synthesis of compound 103:
Figure BDA0001920857510000181
compound 103 is prepared as in example 1, except that starting material A-5 is used in place of starting material A-1 and starting material B-9 is used in place of starting material B-1; elemental analysis Structure (molecular formula C)52H36N2): theoretical value C, 90.67; h, 5.27; n, 4.07; test values are: c, 90.67; h, 5.27; and N, 4.07. ESI-MS (M/z) (M +): theoretical value is 688.87, found 688.87.
Example 11 synthesis of compound 121:
Figure BDA0001920857510000182
the compound 121 was prepared in the same manner as in example 4 except that the starting material A-3 was replaced with the starting material A-6 and the starting material C-1 was replaced with the starting material C-2; elemental analysis Structure (molecular formula C)55H35N3): theoretical value: c, 89.52; h, 4.78; n, 5.69; test values are: c, 89.52; h, 4.77; and N, 5.69. ESI-MS (M/z) (M +): theoretical value is 737.91, found 737.90.
Example 12 synthesis of compound 131:
Figure BDA0001920857510000191
the preparation method of the compound 131 is the same as that of example 1, except that the raw material A-5 is used instead of the raw material A-1, and the raw material B-10 is used instead of the raw material B-1; elemental analysis Structure (molecular formula C)50H31N3): theoretical value: c, 89.13; h, 4.64; n, 6.24; test values are: c, 89.13; h, 4.64; and N, 6.23. ESI-MS (M/z) (M +): theoretical value is 673.82, found 673.78.
Example 13 synthesis of compound 144:
Figure BDA0001920857510000192
compound 144 is prepared as in example 4, except that starting material A-7 is used in place of starting material A-3 and starting material C-3 is used in place of starting material C-1; elemental analysis Structure (molecular formula C)55H35N3O): theoretical value: c, 87.62; h, 4.68; n, 5.57; o, 2.12; test values are: c, 87.61; h, 4.68; n, 5.57; o, 2.13. ESI-MS (M/z) (M +): theoretical value is 753.90, found 753.95.
Example 14 synthesis of compound 154:
Figure BDA0001920857510000193
compound 154 was prepared as in example 1, except that starting material A-7 was used in place of starting material A-1 and starting material B-11 was used in place of starting material B-1; elemental analysis Structure (molecular formula C)58H40N2): theoretical value: c, 91.07; h, 5.27; n, 3.66; test values are: c, 91.06; h, 5.27; and N, 3.66. ESI-MS (M/z) (M +): theoretical value is 764.97, found 764.90.
Example 15 synthesis of compound 166:
Figure BDA0001920857510000201
the preparation method of the compound 166 is the same as that of example 1, except that the raw material A-5 is used instead of the raw material A-1, and the raw material B-12 is used instead of the raw material B-1; elemental analysis Structure (molecular formula C)53H34N2): theoretical value: c, 91.09; h, 4.90; n, 4.01; test values are: c, 91.08; h, 4.91; and N, 4.01. ESI-MS (M/z) (M +): theoretical value is 698.87, found 698.84.
Example 16 synthesis of compound 180:
Figure BDA0001920857510000202
the compound 180 was prepared in the same manner as in example 1 except that the starting material A-1 was replaced with the starting material A-8 and the starting material B-1 was replaced with the starting material B-13; elemental analysis Structure (molecular formula C)60H43N3O2): theory of thingsTheoretical value: c, 86.00; h, 5.17; n, 5.01; o, 3.82; test values are: c, 86.01; h, 5.18; n, 5.01; and O, 3.80. ESI-MS (M/z) (M +): theoretical value is 838.02, found 838.0.
Example 17 synthesis of compound 185:
Figure BDA0001920857510000203
compound 185 is prepared as in example 1, except that starting material A-9 is used in place of starting material A-1 and starting material B-14 is used in place of starting material B-1; elemental analysis Structure (molecular formula C)63H47N3): theoretical value: c, 89.43; h, 5.60; n, 4.97; test values are: c, 89.44; h, 5.60; and N, 4.96. ESI-MS (M/z) (M +): theoretical value is 846.09, found 846.07.
The organic compound of the present invention is used in a light-emitting device, and can be used as a material for a light-emitting layer, an electron-blocking layer, and/or a hole-transporting layer. Compounds 3, 12, 24, 32, 40, 49, 61, 75, 86, 103, 121, 131, 144, 154, 166, 180 and 185 of the present invention were tested for T1 level, thermal properties, and HOMO level, respectively, and the results are shown in table 1.
TABLE 1
Compound (I) T1(eV) Tg(℃) Td(℃) HOMO energy level (eV)
Compound 3 2.75 142 403 -5.81
Compound 12 2.76 143 403 -5.82
Compound 24 2.74 146 405 -5.82
Compound 32 2.75 147 406 -5.83
Compound 40 2.75 152 412 -5.68
Compound 49 2.76 148 409 -5.82
Compound 61 2.75 148 408 -5.83
Compound 75 2.77 149 409 -5.65
Compound 86 2.75 150 410 -5.84
Compound 103 2.73 145 405 -5.82
Compound 121 2.74 146 406 -5.81
Compound 131 2.75 144 405 -5.84
Compound 144 2.76 147 407 -5.80
Compound 154 2.77 149 408 -5.85
Compound 166 2.74 145 405 -5.84
Compound 180 2.76 150 410 -5.83
Compound 185 2.75 148 409 -5.64
Note: the triplet energy level T1 was measured by Hitachi F4600 fluorescence spectrometer under the conditions of 2X 10-5A toluene solution of (4); 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 highest occupied molecular orbital HOMO energy level was tested by the ionization energy testing system (IPS3) in an atmospheric environment.
As can be seen from the data in table 1, the organic compound of the present invention has a suitable HOMO energy level and can be applied to an electron blocking layer, and the organic compound containing ethylenic fluorene as a core has a higher triplet state energy level and a higher thermal stability, so that the efficiency and the lifetime of the manufactured OLED device containing the organic compound of the present invention are both improved.
The effect of the synthesized compound of the present invention as an electron blocking layer material in a device is explained in detail by device examples 1 to 17 and device comparative example 1 below. Device examples 2-17 and device comparative example 1 compared with device example 1, 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 hole transport layer material in the devices was changed. The device stack structure is shown in table 2, and the performance test results of each device are shown in tables 3 and 4.
Device example 1
As shown in fig. 1, a method for manufacturing an electroluminescent device includes the following steps:
a) cleaning the ITO anode layer 2 on the transparent substrate layer 1, respectively ultrasonically cleaning the ITO anode layer 2 with deionized water, acetone and ethanol for 15 minutes, and then treating the ITO anode layer 2 in a plasma cleaner for 2 minutes;
b) evaporating a hole injection layer material HAT-CN on the ITO anode layer 2 in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 10nm, and the hole injection layer material HAT-CN is used as a hole injection layer 3;
c) evaporating a hole transport material HT-1 with the thickness of 60nm on the hole injection layer 3 in a vacuum evaporation mode, wherein the layer is a hole transport layer 4;
d) the compound 3 prepared in the embodiment of the invention is evaporated on the hole transport layer 4 in a vacuum evaporation mode, the thickness is 20nm, and the layer is an electron blocking layer 5;
e) a light-emitting layer 6 is evaporated on the electron blocking layer 5, the main materials are GH-1 and GH-2, the doping materials are GD-1, the mass ratio of GH-1, GH-2 and GD-1 is 45:45:10, and the thickness is 40 nm;
f) an electron transport material ET-1 and Liq are evaporated on the luminescent layer 6 in a vacuum evaporation mode according to the mass ratio of 1:1, the thickness is 35nm, and the organic material of the layer is used as an electron transport layer 7 (also can be understood as a hole blocking layer);
g) vacuum evaporating an electron injection layer LiF with the thickness of 1nm on the electron transport layer 7, wherein the electron injection layer is an electron injection layer 8;
h) vacuum evaporating cathode Al (100nm) on the electron injection layer 8, which is a cathode reflection electrode layer 9;
after the electroluminescent device was fabricated according to the above procedure, IVL data and light decay life of the device were measured, and the results are shown in table 3. The molecular structural formula of the related material is shown as follows:
Figure BDA0001920857510000231
TABLE 2
Figure BDA0001920857510000232
Figure BDA0001920857510000241
Figure BDA0001920857510000251
The efficiency and lifetime data for each device example and device comparative example 1 are shown in table 3.
TABLE 3
Numbering Current efficiency (cd/A) Color(s) LT97 Life (Hr) @5000nits
Device example 1 65.7 Green light 126.5
Device example 2 66.5 Green light 124.0
Device example 3 65.0 Green light 117.1
Device example 4 67.3 Green light 119.3
Device example 5 68.4 Green light 126.1
Device example 6 69.9 Green light 123.7
Device example 7 66.2 Green light 122.5
Device example 8 65.7 Green light 125.3
Device example 9 65.8 Green light 124.2
Device example 10 67.5 Green light 115.6
Device example 11 65.2 Green light 121.2
Device example 12 66.7 Green light 123.0
Device example 13 65.6 Green light 122.9
Device example 14 65.5 Green light 120.8
Device example 15 67.0 Green light 124.0
Device example 16 65.8 Green light 117.8
Device example 17 66.0. Green light 123.7
Device example 18 64.1 Green light 125.7
Device example 19 70.7 Green light 124.1
Device example 20 69.8 Green light 121.8
Device example 21 71.4 Green light 126.7
Device example 22 68.7 Green light 123.4
Device example 23 72.5 Green light 125.2
Device comparative example 1 50 Green light 80.5
Note: LT97 refers to a current density of 10mA/cm2In the case, the time taken for the luminance of the device to decay to 97%;
the life test system is a Korean pulse science M600 type OLED device life tester.
As can be seen from the device data results of table 3, the organic light emitting device of the present invention achieves a greater improvement in both efficiency and lifetime over OLED devices of known materials.
Further, the efficiency of the OLED device prepared by the material is stable when the OLED device works at low temperature, the efficiency test is carried out on the device examples 2, 10 and 16 and the device comparative example 1 at the temperature of-10-80 ℃, and the obtained results are shown in the table 4 and the figure 2.
TABLE 4
Figure BDA0001920857510000271
As can be seen from the data in table 4 and fig. 2, device examples 2, 10, and 16 are device structures in which the material of the present invention and the known material are combined, and compared with device comparative example 1, the efficiency is high at low temperature, and the efficiency is smoothly increased during the temperature increase process.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (10)

1. A compound with ethylenic fluorene as a core is characterized in that the structure of the compound is shown as a general formula (1):
Figure FDA0001920857500000011
in the general formula (1), the dotted line represents that two groups are linked or not linked by a single bond;
Z、Z1each independently represents a nitrogen atom or C-H; z, Z at the connection site1Represented as a carbon atom;
a. b, c and d are integers which are not less than 0 respectively, and a + b + c + d are not less than 1;
R1、R2、R3、R4each independently represents a hydrogen atom, protium, deuterium, tritium, cyano group, halogen, C1-20The alkyl group of (a), a structure represented by general formula (2) or general formula (3), and at least one of the alkyl group is represented by general formula (2) or general formula (3);
Figure FDA0001920857500000012
in the general formulae (2) and (3), Ar1、Ar2Each independently represents a single bond, substituted or unsubstituted C6-30Arylene, 5-30 membered heteroarylene substituted or unsubstituted with one or more heteroatoms;
in the general formula (3), X1Represented by-O-, -S-, -C (R)10)(R11) -or-N (R)12)-；
In the general formula (2) and the general formula (3), R5、R6、R7Each independently represents a hydrogen atom, a structure represented by general formula (4), general formula (5) or general formula (6);
Figure FDA0001920857500000013
in the general formula (4), X2、X3Each independently represents a single bond, -O-, -S-, -C (R)13)(R14) -or-N (R)15) -; and X2、X3Not simultaneously represent a single bond;
in the general formula (5), R8、R9Each independently represents substituted or unsubstituted C6-30Aryl, 5-30 membered heteroaryl, substituted or unsubstituted with one or more heteroatoms;
Y1、Y2、Y3and Y4Each independently represents a nitrogen atom or C (R)16) Wherein at least one is represented by N; and connect Y at the site1、Y2、Y3And Y4Represented as a carbon atom;
the two adjacent positions marked by x in the general formula (4) and the general formula (6) are connected with the two adjacent positions marked by x in the general formula (2) or the general formula (3) in a ring-by-ring manner;
the R is10～R15Each independently is represented by C1-20Alkyl, substituted or unsubstituted C6-30Aryl, 5-30 membered heteroaryl, substituted or unsubstituted with one or more heteroatoms; and R is10And R11、R13And R14Do not form a ring or bond to each other to form a ring;
the R is16Expressed as hydrogen atom, protium, deuterium, tritium, cyano, halogen, C1-20Alkyl, substituted or unsubstituted C6-30Aryl, 5-30 membered heteroaryl, substituted or unsubstituted with one or more heteroatoms;
the substituent for the substitution of each of the above groups is optionally selected from protium, deuterium, tritium, cyano, halogen atom, cyano, C1-20Alkyl of (C)6-30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the hetero atom in the heteroarylene group or the heteroaryl group is any one or more selected from N, O or S.
2. The compound having an ethylenic fluorene as a core according to claim 1, wherein a, b, c, d are each 0 or 1; the R is1、R2、R3、R4Each independently represents a hydrogen atom, protium, deuterium, tritium, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, a structure represented by general formula (2) or general formula (3), and at least one of the structures is represented by general formula (2) or general formula (3).
3. The compound having an ethylenic fluorene as a core according to claim 1, wherein R is5And R6Not simultaneously represented as a hydrogen atom, R7Not represented as hydrogen atoms.
4. A compound having an ethylenic fluorene as a core according to claim 1, wherein the dotted line represents that two groups are connected by a single bond, Z represents a carbon atom, Y represents1、Y2、Y3And Y4With only one being represented as a nitrogen atom.
5. An ethylenically fluorene-containing core compound according to claim 1, wherein the dotted line represents two groups connected by a single bond, and a + b + c + d is 2, R1、R2、R3Or R4One group is represented by a structure shown in a general formula (2) or a general formula (3), and the other group is tert-butyl.
6. The ethylenic fluorene-containing core compound according to claim 1, wherein Ar is Ar1、Ar2Each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthyridine group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranylene group;
the R is8、R9Each independently represents substituted orOne of unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted 9, 9-diphenylfluorenyl, substituted or unsubstituted 9, 9-spirofluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted phenanthryl, and substituted or unsubstituted anthracyl;
the R is10～R15Each independently represents one of methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, pentyl, hexyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl and substituted or unsubstituted pyridyl;
the R is16Represented by hydrogen atom, protium, deuterium, tritium, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted biphenyl group;
the substituent when each of the above groups is substituted is optionally one or more selected from protium, deuterium, tritium, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, naphthyl, naphthyridinyl, pyridyl, biphenylyl, terphenylyl, carbazolyl, or dibenzofuranyl.
7. The ethylenic fluorene-containing core compound according to claim 1, wherein the general formula (1) is any one of the following specific compounds:
Figure FDA0001920857500000031
Figure FDA0001920857500000041
Figure FDA0001920857500000051
Figure FDA0001920857500000061
Figure FDA0001920857500000071
Figure FDA0001920857500000081
Figure FDA0001920857500000091
Figure FDA0001920857500000101
Figure FDA0001920857500000111
Figure FDA0001920857500000121
Figure FDA0001920857500000122
any one of the above.
8. An organic electroluminescent device comprising a plurality of organic thin film layers between an anode and a cathode, wherein at least one of the organic thin film layers contains the compound having an ethylenic fluorene as a core according to any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, wherein the organic thin film layer comprises a light-emitting layer, an electron-blocking layer and/or a hole-transporting layer, and the light-emitting layer, the electron-blocking layer and/or the hole-transporting layer contain the compound having the ethylenic fluorene as a core.
10. A lighting or display element, characterized in that the display element comprises the organic electroluminescent device according to any one of claims 8 or 9.
CN201811593668.6A 2018-12-25 2018-12-25 Compound with olefinic bond-containing fluorene as core and application thereof Pending CN111362959A (en)

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CN115710186A (en) * 2022-10-27 2023-02-24 上海八亿时空先进材料有限公司 Fluorene derivative and application thereof

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