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CN111253410A - Compound with fluorene as core and application thereof - Google Patents

Compound with fluorene as core and application thereof Download PDF

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CN111253410A
CN111253410A CN201910536973.XA CN201910536973A CN111253410A CN 111253410 A CN111253410 A CN 111253410A CN 201910536973 A CN201910536973 A CN 201910536973A CN 111253410 A CN111253410 A CN 111253410A
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李崇
吴秀琴
王芳
谢丹丹
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Jiangsu Sunera Technology Co Ltd
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Abstract

The invention discloses a compound taking fluorene as a core and application thereof, and the structure of the organic compound provided by the invention is shown as a general formula (1).
Figure DDA0002101479800000011
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.

Description

Compound with fluorene as core and application thereof
Technical Field
The invention relates to the technical field of semiconductor materials, in particular to a compound taking fluorene as a core 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 present applicant provides a fluorene-based compound and applications thereof. The compound takes fluorene as a core, has higher glass transition temperature and molecular thermal stability and proper HOMO energy level, 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 fluorene as a core has a structure shown as a general formula (1):
Figure BDA0002101479780000021
in the general formula (1), L1、L2Each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthyridine group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridylene group, or a substituted or unsubstituted terphenylene group;
ar is1、Ar2Each independently represents a hydrogen atom, C1-10Alkyl, substituted or unsubstituted C6-60An aryl group of (a), a substituted or unsubstituted 5-60 membered heteroaryl group containing one or more heteroatoms;
the R is1And R independently represents substituted or unsubstituted C6-60An aryl group of (a), a substituted or unsubstituted 5-60 membered heteroaryl group containing one or more heteroatoms; the R is2Represented by a structure represented by the general formula (2);
Figure BDA0002101479780000022
in the general formula (2), R3、R4Each independently represents a hydrogen atom, a structure represented by the general formula (3) or the general formula (4), and R3、R4Not simultaneously represented as a hydrogen atom;
Figure BDA0002101479780000031
X、X1、X2each independently represents a single bond, -O-, -S-, -C (R)5)(R6) -or-N (R)7) -; and X1、X2Not simultaneously represent a single bond;
the two adjacent positions marked by the star mark in the general formula (3) and the general formula (4) are connected with the two adjacent positions L1-L2, L2-L3, L3-L4, L '1-L'2, L '2-L'3 or L '3-L'4 in the general formula (2) in a ring-by-ring manner;
the R is5～R7Each independently represents C1-20Alkyl, substituted or unsubstituted C6-30Aryl, 5-30 membered heteroaryl, substituted or unsubstituted with one or more heteroatoms; and R is5And R6Can be bonded to each other to form a ring;
the substituent is halogen atom, cyano, C1-20Alkyl of (C)6-30Aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom in the heteroaryl group is selected from N, O or S.
As a further improvement of the invention, the compound is selected from the structures shown in the general formula (5), the general formula (6), the general formula (7), the general formula (8) or the general formula (9):
Figure BDA0002101479780000032
as a further improvement of the invention, Ar is1、Ar2Each independently represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthracyl group, a substituted or unsubstituted pyranyl group, a substituted or unsubstituted triphenylene group, a phenyl group, a naphthyl group,substituted or unsubstituted pyridyl, substituted or unsubstituted azacarbazolyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted thienyl;
the R is1R independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted thienyl group;
the R is5～R7Each independently represents one of methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, amyl, hexyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl and substituted or unsubstituted pyridyl;
the substituent is selected from one or more of fluorine atoms, cyano groups, phenyl groups, biphenyl groups, naphthyl groups, furyl groups, carbazolyl groups, thienyl groups or pyridyl groups.
As a further improvement of the invention, the specific compound of the general formula (1) is:
Figure BDA0002101479780000041
Figure BDA0002101479780000051
Figure BDA0002101479780000061
Figure BDA0002101479780000071
Figure BDA0002101479780000081
Figure BDA0002101479780000091
Figure BDA0002101479780000101
Figure BDA0002101479780000111
Figure BDA0002101479780000121
the compound provided by the invention can be applied to the preparation of organic electroluminescent devices.
Specifically, 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 fluorene-based compound.
Specifically, the hole transport layer material or the electron blocking layer material of the organic electroluminescent device is the compound taking fluorene as the core.
Specifically, the material of the light-emitting layer of the organic electroluminescent device is the compound taking fluorene as the core.
The invention also provides a lighting or display element comprising the organic electroluminescent device.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) the compound takes fluorene as a core, is connected with an electron-donating group, has high triplet state energy level (T1), can effectively block exciton energy of a light-emitting layer from being transferred to a hole transport layer when being used as an electron blocking layer material of an OLED light-emitting device, improves the recombination efficiency of excitons in the light-emitting layer, improves the energy utilization rate, and thus improves the light-emitting efficiency of the device.
(2) The compound structure of the invention is distributed in a star structure, and all branched chains are mutually crossed and separated to avoid free rotation of groups, so that the compound has higher Tg temperature and smaller intermolecular force. The compound has lower evaporation temperature due to smaller intermolecular force, thereby not only ensuring that the evaporation material is not decomposed for a long time in mass production, but also reducing the deformation influence of heat radiation of the evaporation temperature on the Mask.
(3) 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 is hole transport, 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 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.
The synthesis of starting material a in the following examples is as follows:
taking the synthesis example of the raw material A-1:
Figure BDA0002101479780000131
0.01mol of the raw material a1 and 0.012mol of the raw material b1 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 2mL K2CO3Reacting the solution (0.01mol/mL) at 110 ℃ for 24 hours in the atmosphere of introducing nitrogen, sampling a sample, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain a raw material A-1; elemental analysis Structure (molecular formula C)31H20Br2): theoretical value: c, 67.42; h, 3.65; br, 28.93; test values are: c, 67.44; h, 3.64; br, 28.92. ESI-MS (M/z) (M +): theoretical value is 552.31, found 552.30.
Synthesis of starting material A analogously to the Synthesis of starting material A-1, starting materials a and b were used as indicated in the following Table:
Figure BDA0002101479780000132
Figure BDA0002101479780000141
example 1 synthesis of compound 1:
Figure BDA0002101479780000151
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 2mL K2CO3Reacting the solution (0.01mol/mL) at 110 ℃ for 24 hours in the atmosphere of introducing nitrogen, sampling a sample, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain an intermediate 1;
further, 0.01mol of the raw material C-1 was charged in an atmosphere of nitrogen gas0.012mol of intermediate 1, 0.03mol of potassium tert-butoxide, 1X 10-4mol Pd2(dba)3，1×10-4Adding 150ml of toluene and 150ml of triphenylphosphine into a 250ml three-necked bottle, 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 compound 1; elemental analysis Structure (molecular formula C)55H35NO): theoretical value: c, 91.01; h, 4.86; n, 1.93; o, 2.20; test values are: c, 91.0; h, 4.86; n, 1.93; o, 2.21. ESI-MS (M/z) (M +): theoretical value is 725.89, found 725.91.
Example 2 synthesis of compound 12:
Figure BDA0002101479780000152
compound 12 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, the starting material B-1 was replaced with the starting material B-2, and the starting material C-1 was replaced with the starting material C-2; elemental analysis Structure (molecular formula C)61H37NO2): theoretical value: c, 89.79; h, 4.57; n, 1.72; o, 3.92; test values are: c, 89.79; h, 4.58; n, 1.72; and O, 3.91. ESI-MS (M/z) (M +): theoretical value is 815.97, found 815.95.
Example 3 synthesis of compound 21:
Figure BDA0002101479780000161
compound 21 was prepared as in example 1, except that the starting material C-1 was replaced with the starting material C-3; elemental analysis Structure (molecular formula C)58H41N): theoretical value: c, 92.64; h, 5.50; n, 1.86; test values are: c, 92.65; h, 5.51; n, 1.84. ESI-MS (M/z) (M +): theoretical value is 751.97, found 751.93.
Example 4 synthesis of compound 30:
Figure BDA0002101479780000162
preparation of Compound 30Example 1 except that the raw material A-1 was replaced with the raw material A-2, the raw material B-1 was replaced with the raw material B-3, and the raw material C-1 was replaced with the raw material C-4; elemental analysis Structure (molecular formula C)57H40N2): theoretical value: c, 90.92; h, 5.35; n, 3.72; test values are: c, 90.93; h, 5.35; and N, 3.71. ESI-MS (M/z) (M +): theoretical value is 752.96, found 752.93.
Example 5 synthesis of compound 40:
Figure BDA0002101479780000171
a250 ml three-necked flask was charged with 0.01mol of the raw material C-5, 0.012mol of the raw material A-3, 0.03mol of potassium tert-butoxide, and 1X 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 40; elemental analysis Structure (molecular formula C)54H35N3): theoretical value C, 89.35; h, 4.86; n, 5.79; test values are: c, 89.36; h, 4.85; n, 5.79. ESI-MS (M/z) (M +): theoretical value is 725.89, found 725.92.
Example 6 synthesis of compound 54:
Figure BDA0002101479780000172
compound 54 can be prepared by the same method as in example 1, except that the starting material A-1 is replaced with starting material A-4 and the starting material C-1 is replaced with starting material C-6; elemental analysis Structure (molecular formula C)67H44N2): theoretical value C, 91.75; h, 5.06; n, 3.19; test values are: c, 91.76; h, 5.06; and N, 3.18. ESI-MS (M/z) (M +): theoretical value is 876.35, found 876.08.
Example 7 synthesis of compound 66:
Figure BDA0002101479780000173
Figure BDA0002101479780000181
compound 66 was prepared as in example 1, except that starting material A-5 was used in place of starting material A-1 and starting material C-7 was used in place of starting material C-1; elemental analysis Structure (molecular formula C)59H37NO): theoretical value C, 91.33; h, 4.81; n, 1.81; o, 2.06; test values are: c, 91.34; h, 4.80; n, 1.81; and O, 2.06. ESI-MS (M/z) (M +): theoretical value is 775.95, found 775.98.
Example 8 synthesis of compound 75:
Figure BDA0002101479780000182
intermediate 6 was prepared as in intermediate 1 of example 1, except that starting material a-6 was used in place of starting material a-1;
0.01mol of intermediate 6 and 0.012mol of starting material D-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 2mL of 0.01mol/mL K2CO3Reacting the solution at 110 ℃ for 24 hours in the atmosphere of introducing nitrogen, sampling a sample, cooling and filtering after the raw materials are completely reacted, removing the solvent from the filtrate by rotary evaporation, and passing the crude product through a silica gel column to obtain a compound 75; elemental analysis Structure (molecular formula C)61H39NO): theoretical value: c, 91.36; h, 4.90; n, 1.75; o, 1.99; test values are: c, 91.37; h, 4.90; n, 1.75; o, 1.98. ESI-MS (M/z) (M +): theoretical value is 801.99, found 801.96.
Example 9 synthesis of compound 83:
Figure BDA0002101479780000191
compound 83 is prepared as in example 7, except that the starting material C-7 is replaced with the starting material C-8; elemental analysis Structure (molecular formula C)55H35NO2): theoretical value: c, 89.04; h, 4.76; n, 1.89; o, 4.31; test value: c, 89.05; h, 4.76; n, 1.89; and O, 4.30. ESI-MS (M/z) (M +): theoretical value is 741.89, found 741.85.
Example 10 synthesis of compound 96:
Figure BDA0002101479780000192
compound 96 is prepared as in example 1, except that starting material A-1 is replaced with starting material A-2, starting material B-1 is replaced with starting material B-4, and starting material C-1 is replaced with starting material C-9; elemental analysis Structure (molecular formula C)62H43N): theoretical value C, 92.85; h, 5.40; n, 1.75; test values are: c, 92.86; h, 5.41; n, 1.73. ESI-MS (M/z) (M +): the theoretical value was 801.34, and the actual value was 801.11.
Example 11 synthesis of compound 114:
Figure BDA0002101479780000193
compound 114 was prepared as in example 7, except that the starting material C-7 was replaced with the starting material C-10; elemental analysis Structure (molecular formula C)61H37NO4): theoretical value: c, 86.40; h, 4.40; n, 1.65; o, 7.55; test values are: c, 86.41; h, 4.41; n, 1.65; o, 7.53. ESI-MS (M/z) (M +): theoretical value is 847.97, found 847.94.
Example 12 synthesis of compound 122:
Figure BDA0002101479780000201
compound 122 is prepared as in example 5, except that starting material A-7 is used in place of starting material A-3 and starting material C-11 is used in place of starting material C-5; elemental analysis Structure (molecular formula C)59H44N2): theoretical value: c, 90.73; h, 5.68; n, 3.59; test values are: c, 90.72; h, 5.69; and N, 3.59. ESI-MS (M/z) (M +): theoretical value is 780.35, found 780.09.
Example 13 synthesis of compound 137:
Figure BDA0002101479780000202
the compound 137 was prepared in the same manner as in example 1 except that the raw material A-8 was used in place of the raw material A-1 and the raw material C-12 was used in place of the raw material C-1; elemental analysis Structure (molecular formula C)66H43N3): theoretical value: c, 90.28; h, 4.94; n, 4.79; test values are: c, 90.29; h, 4.94; n, 4.78. ESI-MS (M/z) (M +): theoretical value is 877.35, found 877.05.
Example 14 synthesis of compound 151:
Figure BDA0002101479780000203
compound 151 was prepared as in example 2, except that the starting material C-2 was replaced with the starting material C-13; elemental analysis Structure (molecular formula C)61H37NOS): theoretical value: c, 88.06; h, 4.48; n, 1.68; o, 1.92; s, 3.85; test values are: c, 88.07; h, 4.48; n, 1.68; o, 1.91; and S, 3.85. ESI-MS (M/z) (M +): theoretical value is 831.26, found 831.12.
Example 15 synthesis of compound 163:
Figure BDA0002101479780000211
compound 163 was prepared in the same manner as in example 1 except that the raw material A-1 was replaced with the raw material A-2 and the raw material C-1 was replaced with the raw material C-14; elemental analysis Structure (molecular formula C)68H43N): theoretical value: c, 93.44; h, 4.96; n, 1.60; test values are: c, 93.45; h, 4.95; and N, 1.60. ESI-MS (M/z) (M +): theoretical value is 873.34, found 873.08.
Example 16 synthesis of compound 174:
Figure BDA0002101479780000212
compound 174 was prepared as in example 1, except that starting material B-1 was replaced with starting material B-2,the raw material C-15 replaces the raw material C-1; elemental analysis Structure (molecular formula C)64H43NO2): theoretical value: c, 89.59; h, 5.05; n, 1.63; o, 3.73; test values are: c, 89.60; h, 5.06; n, 1.63; and O, 3.71. ESI-MS (M/z) (M +): theoretical value is 857.33, found 857.0.
Example 17 synthesis of compound 197:
Figure BDA0002101479780000213
compound 197 is prepared as in example 15, except that the starting material C-14 is replaced with the starting material C-16; elemental analysis Structure (molecular formula C)70H50N2): theoretical value: c, 91.47; h, 5.48; n, 3.05; test values are: c, 91.48; h, 5.47; and N, 3.05. ESI-MS (M/z) (M +): theoretical value is 918.40, found 918.20.
The organic compound of the present invention is used in a light-emitting device, and can be used as a hole transporting, electron blocking or light-emitting layer material. Compounds 1, 6, 12, 21, 30, 40, 47, 54, 66, 74, 75, 83, 96, 114, 122, 126, 137, 151, 163, 174, 189, 197 and 210 of the present invention were tested for the T1 level, thermal properties and HOMO level, respectively, and the results of the tests are shown in table 1.
TABLE 1
Figure BDA0002101479780000221
Figure BDA0002101479780000231
Note: the triplet energy level T1 was measured by Hitachi F4600 fluorescence spectrometer under the conditions of 2X 10- 5A 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 thermogravimetric temperature Td was a temperature at which 1% of the weight loss was observed in a nitrogen atmosphere, and was measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate was20 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 high glass transition temperature, and can improve the phase stability of the material film, thereby further improving the service life of the device; the high T1 energy level can block the energy loss of the light-emitting layer, thereby improving the light-emitting efficiency of the device; the appropriate HOMO energy level can solve the problem of carrier injection and can reduce the voltage of the device. Therefore, after the organic compound containing fluorene is used for different functional layers of an OLED device, the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.
The arrangement mode and the interaction energy between two molecules are calculated by using Gaussian 16 software and adopting a B3LYP/6-31G (d) method, and the smaller the value of the interaction energy between the molecules is, the larger the energy released by the molecules is, the larger the interaction force between the molecules is, the more stable the molecules are, and the less separation is easy to occur. The results of the comparison of the compounds of the invention with the comparative structures are shown in table 2:
TABLE 2
Figure BDA0002101479780000232
Figure BDA0002101479780000241
The data in table 2 show that the comparative compound H1 has a large intermolecular interaction force, and when the comparative compound is used in an electroluminescent device, the display effect of the device is adversely affected, because when the comparative compound is used as an OLED device, the film formation method used is an evaporation method, and when an organic compound having an excessively large intermolecular interaction force is heated and evaporated, the evaporation temperature is significantly increased to overcome the intermolecular interaction force, and the excessively high evaporation temperature causes decomposition of organic molecules to generate impurities, thereby reducing the service life of the device; the compound of the invention has relatively small intermolecular interaction force, is easy to overcome the problem that intermolecular interaction force is evaporated onto a substrate, so that the evaporation temperature can be reduced, and the problem of organic molecule decomposition caused by overhigh evaporation temperature of the molecules of the contrast compound is solved.
The effect of the synthesized compound of the present invention as a hole transport layer material in a device is explained in detail below by device examples 1 to 23 and device comparative example 1. Compared with the device example 1, the device examples 2 to 23 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 luminescent layer material or the electron barrier layer material in the device is replaced. The device stack structure is shown in table 3, and the performance test results of each device are shown in tables 4 and 5.
Device example 1
Transparent substrate layer/ITO anode layer/hole injection layer (HAT-CN, thickness 10 nm)/hole transport layer (HT-1, thickness 60 nm)/electron blocking layer (Compound 1, thickness 20 nm)/light emitting layer (GH1, GH2 and GD-1) were co-doped in a weight ratio of 45:45:10, thickness 30 nm)/hole blocking/electron transport layer (ET-1 and Liq, co-doped in a weight ratio of 1:1, thickness 40 nm)/electron injection layer (LiF, thickness 1 nm)/cathode layer (Mg and Ag, co-doped in a weight ratio of 9:1, thickness 15nm)/CPL layer (Compound CP-1, thickness 70 nm).
The preparation process comprises the following steps:
as shown in fig. 1, 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, HT-1 was evaporated to a thickness of 60nm as a hole transport layer. Compound 1 was then evaporated to a thickness of 20nm as an electron blocking layer. After the evaporation of the hole transport material 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 GH-1 and GH-2 used by the OLED light emitting layer 6 are used as main body materials, GD-1 is 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 30 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 40nm, 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. 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 of the device and the lifetime of the device were measured.
Figure BDA0002101479780000251
TABLE 3
Figure BDA0002101479780000252
Figure BDA0002101479780000261
Figure BDA0002101479780000271
Figure BDA0002101479780000281
The current efficiencies of the respective device examples and device comparative example 1 are shown in table 4.
TABLE 4
Figure BDA0002101479780000282
Figure BDA0002101479780000291
The current efficiency is at a current density of 10m/cm2Tested under the circumstances.
As can be seen from the device data results of table 4, the efficiency of the organic light emitting device of the present invention is greatly improved compared to the OLED device of the known material.
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, 8 and 15 and the device comparative example 1 at the temperature of-10-80 ℃, and the obtained results are shown in the table 5 and the figure 2.
TABLE 5
Figure BDA0002101479780000292
As can be seen from the data in table 5 and fig. 2, device examples 2, 8, and 15 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 (9)

1. A fluorene-core compound, characterized in that the structure of the compound is represented by general formula (1):
Figure FDA0002101479770000011
in the general formula (1), L1、L2Each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthyridine group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenylthio group, a substituted,Substituted or unsubstituted pyridylene, substituted or unsubstituted terphenylene;
ar is1、Ar2Each independently represents a hydrogen atom, C1-10Alkyl, substituted or unsubstituted C6-60An aryl group of (a), a substituted or unsubstituted 5-60 membered heteroaryl group containing one or more heteroatoms;
the R is1And R independently represents substituted or unsubstituted C6-60An aryl group of (a), a substituted or unsubstituted 5-60 membered heteroaryl group containing one or more heteroatoms; the R is2Represented by a structure represented by the general formula (2);
Figure FDA0002101479770000012
in the general formula (2), R3、R4Each independently represents a hydrogen atom, a structure represented by the general formula (3) or the general formula (4), and R3、R4Not simultaneously represented as a hydrogen atom;
Figure FDA0002101479770000013
X、X1、X2each independently represents a single bond, -O-, -S-, -C (R)5)(R6) -or-N (R)7) -; and X1、X2Not simultaneously represent a single bond;
the two adjacent positions marked by the star mark in the general formula (3) and the general formula (4) are connected with the two adjacent positions L1-L2, L2-L3, L3-L4, L '1-L'2, L '2-L'3 or L '3-L'4 in the general formula (2) in a ring-by-ring manner;
the R is5～R7Each independently represents C1-20Alkyl, substituted or unsubstituted C6-30Aryl, 5-30 membered heteroaryl, substituted or unsubstituted with one or more heteroatoms; and R is5And R6Can be bonded to each other to form a ring;
the substituent is halogen atom, cyano, C1-20Alkyl of (C)6-30Aryl, 5-30 membered heteroaryl containing one or more heteroatoms；
The heteroatom in the heteroaryl group is selected from N, O or S.
2. The compound of claim 1, wherein the compound is selected from the group consisting of structures represented by formula (5), formula (6), formula (7), formula (8), and formula (9):
Figure FDA0002101479770000021
3. the compound of claim 1, wherein Ar is Ar1、Ar2Each independently represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted thienyl group;
the R is1R independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted thienyl group;
the R is5～R7Each independently represents methyl, ethyl, propyl, isopropyl, butyl, tert-butylOne of butyl, pentyl, hexyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyridyl;
the substituent is one or more of fluorine atom, cyano, phenyl, biphenyl, naphthyl, furyl, carbazolyl, thienyl or pyridyl.
4. A compound according to claims 1-3, characterized in that the specific compound of general formula (1) is:
Figure FDA0002101479770000031
Figure FDA0002101479770000041
Figure FDA0002101479770000051
Figure FDA0002101479770000061
Figure FDA0002101479770000071
Figure FDA0002101479770000081
Figure FDA0002101479770000091
Figure FDA0002101479770000101
Figure FDA0002101479770000111
5. use of a fluorene-based compound according to any one of claims 1 to 4 for the preparation of organic electroluminescent devices.
6. 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 fluorene-based compound according to any one of claims 1 to 4.
7. An organic electroluminescent device, characterized in that an electron blocking material or a hole transporting material of the organic electroluminescent device contains the fluorene-based compound according to any one of claims 1 to 4.
8. An organic electroluminescent device, characterized in that a luminescent layer material of the organic electroluminescent device contains the fluorene-based compound according to any one of claims 1 to 4.
9. A lighting or display element comprising the organic electroluminescent device according to any one of claims 6 to 8.
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Publication number Priority date Publication date Assignee Title
CN111689946A (en) * 2020-06-17 2020-09-22 深圳大学 Carbazole aromatic ring thermal activation delayed fluorescent material and organic electroluminescent device thereof
WO2022196749A1 (en) * 2021-03-18 2022-09-22 出光興産株式会社 Organic electroluminescent element, compound, and electronic device

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