CN111662225A - Organic compound containing pyrene and application thereof - Google Patents
Organic compound containing pyrene and application thereof Download PDFInfo
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Abstract
The invention relates to a pyrene-containing organic compound and application thereof, belongs to the technical field of semiconductors, and provides a compound with a structure shown as a general formula (1)：
The compound provided by the invention has stronger hole transmission capability, and under the appropriate 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 light-emitting layer. When the compound is applied to an OLED device, high film stability can be kept through device structure optimization, and the photoelectric performance of the OLED device and the service life of the OLED device can be effectively improved.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to an organic compound containing pyrene 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 of a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and the various different functional materials are mutually overlapped together according to the application to form the OLED light-emitting device. When voltage is applied to two end electrodes of the OLED light-emitting device as a current device, positive and negative charges in the organic layer functional material film layer are acted through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, namely OLED electroluminescence is generated.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, and the OLED device structure applied in industry comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transport material, a light emitting material, an electron transport material and the like, and the material type and the matching form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional materials have stronger selectivity, and the performance of the same materials in the devices with different structures can also be completely different.
Therefore, aiming at the industrial application requirements of the current OLED device, different functional film layers of the OLED device and the photoelectric characteristic requirements of the device, a more suitable OLED functional material or material combination with high performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides an organic compound containing pyrene and application thereof in an organic electroluminescent device. The organic compound provided by the invention has good thermal stability, higher glass transition temperature and proper HOMO energy level, and the device adopting the organic compound provided by the invention can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through structure optimization.
The specific technical scheme is as follows: an organic pyrene-containing compound having a structure represented by general formula (1):
in the general formula (1), L, L1、L2Each independently represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted spirofluorenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted naphthyridinylene group, and L, L1May also represent a single bond;
the R represents substituted or unsubstituted C6-30Aryl, 5 to 30 membered heteroaryl containing one or more heteroatoms substituted or unsubstituted;
z is nitrogen atom or C-R1(ii) a Wherein Z at the attachment site is represented as a carbon atom;
z is1-Z8Each independently represents a nitrogen atom or C-R2；
The R is1、R2Each independently represents a hydrogen atom, protium, deuterium, tritium, cyano group, halogen, methoxy group, C1-20Alkyl of (C)2-20Alkenyl of (a), substituted or unsubstituted C6-30Aryl, substituted by one or more hetero atomsOr unsubstituted 5 to 30 membered heteroaryl; and two or more adjacent R2Can be connected with each other to form a ring;
the substituent of the substitutable group is selected from cyano, methoxy, halogen atom, C6-30One or more of aryl, 5-to 30-membered heteroaryl containing one or more heteroatoms;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
As a further improvement of the present invention, R represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted azapyrenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted azabenzophenanthrenyl group, a structure represented by general formula (2), general formula (3), or general formula (4);
said X1、X2、X3Independently represent-O-, -S-, -C (R)3)(R4) -or-N (R)5)-；X2、X3May also represent a single bond;
the Y, Y1、Y2Each independently represents a nitrogen atom or C-R6And Y is1And Y2Can also be connected into a ring;
wherein Y, Y at the site of attachment to another group1、Y2Represented as a carbon atom;
the R is3～R5Are each independently represented by C1-20Alkyl, substituted or unsubstituted C6-30One of an aryl group, a 5-to 30-membered heteroaryl group substituted or unsubstituted with one or more heteroatoms; r3And R4Can be connected with each other to form a ring;
the R is6Is represented by hydrogen atomProtium, deuterium, tritium, cyano, methoxy, halogen, C1-20Alkyl of (C)2-20Alkenyl of (a), substituted or unsubstituted C6-30Aryl, 5 to 30 membered heteroaryl containing one or more heteroatoms substituted or unsubstituted; two or more adjacent R6Can be connected with each other to form a ring;
the substituent of the substitutable group is selected from cyano, methoxy, halogen atom, C6-30One or more of aryl, 5-to 30-membered heteroaryl containing one or more heteroatoms;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
Preferably, the general formula (1) can be represented by a structure shown in a general formula (5), a general formula (6) or a general formula (7);
more preferably, the general formula (1) may be represented by a structure represented by general formula (8), general formula (9), general formula (10) or general formula (11);
even more preferably, said Y, Z1-Z8The number of nitrogen atoms is 0, 1 or 2.
As a further improvement of the invention, R is1、R2、R6Each independently represents one of a hydrogen atom, protium, deuterium, tritium, fluorine atom, methoxy group, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted furyl group, substituted or unsubstituted dibenzofuryl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted carbazolyl group, and substituted or unsubstituted naphthyridinyl group;
the R is3～R5Each independently represents methyl and ethylOne of phenyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, naphthyl, biphenyl, naphthyridinyl or pyridyl;
the substituent of the substitutable group is one or more selected from fluorine atom, methoxy group, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, amyl group, phenyl group, naphthyl group, biphenyl group, naphthyridinyl group or pyridyl group.
As a further improvement of the invention, the compound has a specific structure as follows:
The second aspect of the present invention is to provide a process for producing the above-mentioned organic compound, characterized in that,
the reaction equation for preparing the compound represented by the general formula (1) is shown below:
the specific preparation method of the reaction formula comprises the following steps: weighing a reactant A and an intermediate B, and dissolving the reactant A and the intermediate B by using toluene; then adding Pd2(dba)3、P(t-Bu)3Sodium tert-butoxide; reacting the mixed solution of the reactants at 95-110 ℃ for 10-24 hours under inert atmosphere, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain a product D; the molar ratio of the reactant A to the intermediate B is 1 (1.2-3.0), and Pd2(dba)3The molar ratio of the reactant A to the reactant A is (0.006-0.02) 1, P (t-Bu)3The molar ratio of the sodium tert-butoxide to the reactant A is (0.006-0.02) to 1, and the molar ratio of the sodium tert-butoxide to the reactant A is (1.0-3.0) to 1;
the preparation method of the intermediate B comprises the following steps:
the specific preparation method of the reaction comprises the following steps: weighing raw materials 1 and 2, dissolving with toluene, and adding Pd2(dba)3、P(Ph)3And sodium tert-butoxide; reacting the mixed solution of the reactants at the reaction temperature of 90-110 ℃ for 10-24 hours under the inert atmosphere, cooling, filtering the reaction solution, performing rotary evaporation on the filtrate, and passing through a silica gel column to obtain an intermediate B; the molar ratio of the raw material 1 to the raw material 2 is 1 (1.0-1.5); pd2(dba)3The molar ratio of the sodium tert-butoxide to the raw material 1 is (0.006-0.02):1, and the molar ratio of the sodium tert-butoxide to the raw material 1 is (2.0-3.0): 1; p (Ph)3The mol ratio of the raw material to 1 is (2.0-3.0) to 1;
the reaction mainly utilizes the substitution reaction between the amino compound and the halogen atom, the dosage of each substance is the dosage of one-time substitution reaction, and when multiple substitution reactions exist, the structure of the amino compound is changed according to one-time substitution reaction and the one-time substitution reaction is repeated for multiple times.
The third aspect of the present invention is to provide the use of the organic pyrene-containing compound described above for the preparation of an organic electroluminescent device.
A fourth aspect of the present invention is to provide an organic electroluminescent device having such a feature that the organic electroluminescent device includes at least one functional layer containing the organic compound containing pyrene.
A fifth aspect of the present invention is to provide an organic electroluminescent device comprising a hole transporting layer or an electron blocking layer having such a feature that the hole transporting layer or the electron blocking layer contains the organic compound containing pyrene.
A sixth aspect of the present invention is to provide an organic electroluminescent device comprising a light-emitting layer having such a feature that the light-emitting layer contains the pyrene-containing organic compound described above.
A seventh aspect of the present invention is to provide a lighting or display element having such features, including the organic electroluminescent device described above.
The beneficial effect of above-mentioned scheme is:
the pi conjugation effect in the compound provided by the invention enables the compound to have strong hole transmission capability, the high hole transmission rate can reduce the initial voltage of the device, and the efficiency of the organic electroluminescent device is improved; the asymmetric triarylamine structure can reduce the crystallinity of molecules, reduce the planarity of the molecules and prevent the molecules from moving on the plane, thereby improving the thermal stability of the molecules; meanwhile, the structure of the compound provided by the invention enables the distribution of electrons and holes in the luminescent layer to be more balanced, and under the appropriate HOMO energy level, the hole injection and transmission performance is improved; under a proper LUMO energy level, the organic electroluminescent device also plays a role in blocking electrons, improves the recombination efficiency of excitons in a light-emitting layer, can reduce the efficiency roll-off of the device under high current density, reduces the voltage of the device, improves the current efficiency of the device and prolongs the service life of the device.
The compound structure of the invention is radial, so that the distance between molecules is increased, the interaction force between molecules is weakened, and the evaporation temperature is lower, thereby widening the industrial processing window of the material.
When the compound is applied to an OLED device, high film stability can be kept through device structure optimization, and the photoelectric performance 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 luminescent devices.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
FIG. 2 is a graph of efficiency measured at different temperatures for a device made according to the present invention and a comparative device;
FIG. 3 is a UV absorption spectrum of inventive compound 328;
FIG. 4 is a UV absorption spectrum of compound 575 of the present invention;
in the drawings: 1 is a transparent substrate layer, 2 is an ITO anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is an electron transport or hole blocking layer, 8 is an electron injection layer, 9 is a cathode reflective electrode layer, and 10 is a light extraction layer.
Detailed Description
Example 1: synthesis of intermediate B1:
adding 0.01mol of raw material 1-1, 0.012mol of raw material 2-1, 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5 × 10-5molPd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, and sampling a point plate to show that no bromide is left and the reaction is complete; naturally cooling to room temperature, filtering, rotary evaporating the filtrate until no fraction is obtained, and passing through neutral silica gel columnObtaining a target product intermediate B1; HPLC purity 99.37%, yield 73.4%; elemental analysis Structure (molecular formula C)30H22N2): theoretical value C, 87.77; h, 5.40; n, 6.82; test values are: c, 87.79; h, 5.39; and N, 6.81. ESI-MS (M/z) (M +): theoretical value is 410.18, found 410.31.
The intermediates B required in the examples are synthesized as shown in table 1:
TABLE 1
Example 2: synthesis of Compound 1:
adding 0.01mol of reactant A1, 0.012mol of intermediate B1 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5 × 10-5molPd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, and sampling a point plate to show that no bromide is left and the reaction is complete; naturally cooling to room temperature, filtering, rotatably evaporating the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain the target product with the HPLC purity of 99.73% and the yield of 72.9%. Elemental analysis Structure (molecular formula C)46H30N2): theoretical value C, 90.46; h, 4.95; n, 4.59; test value C, 90.48; h, 4.94; n, 4.58. HPLC-MS: the molecular weight of the material is 610.24,the molecular weight was found to be 610.39.
Example 3: synthesis of Compound 6:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B2 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)50H32N2): theoretical value C, 90.88; h, 4.88; n, 4.24; test values are: c, 90.87; h, 4.87; and N, 4.26. HPLC-MS: the molecular weight of the material is 660.26, and the measured molecular weight is 660.34.
Example 4: synthesis of compound 12:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B3 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)52H32N2O): theoretical value C, 89.12; h, 4.60; n, 4.00; o, 2.28; test values are: c, 89.14; h, 4.58; n, 4.02; o, 2.26. HPLC-MS: the molecular weight of the material is 700.25, and the measured molecular weight is 700.36.
Example 5 Synthesis of Compound 19:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B4 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)59H36N2): theoretical value C, 91.68; h, 4.69; n, 3.62; test values are: c, 91.67; h, 4.68; and N, 3.64. HPLC-MS: the molecular weight of the material is 772.29, and the measured molecular weight is 772.41.
Example 6: synthesis of compound 23:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B5 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)56H34N2O): theoretical value: c, 89.57; h, 4.56; n, 3.73; o, 2.13; test values are: c, 89.56; h, 4.57; n, 3.74; o, 2.12. HPLC-MS: the molecular weight of the material is 750.27, and the measured molecular weight is 750.39.
Example 7: synthesis of compound 25:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B6 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)52H34N2): theoretical value C, 90.93; h, 4.99; n, 4.08; test values are: c, 90.94; h, 4.98; and N, 4.10. HPLC-MS: the molecular weight of the material is 686.27, and the measured molecular weight is 686.32.
Example 8: synthesis of compound 29:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B7 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)48H33N3): theoretical value C, 88.45; h, 5.10; n, 6.45; test values are: c, 88.47; h, 5.09; n, 6.44. HPLC-MS: the molecular weight of the material is 651.27, and the measured molecular weight is 651.32.
Example 9: synthesis of compound 42:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B8 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)52H34N2): theoretical value C, 90.93; h, 4.99; n, 4.08; test values are: c, 90.94; h,4.97; and N, 4.09. HPLC-MS: the molecular weight of the material is 686.27, and the measured molecular weight is 686.34.
Example 10: synthesis of compound 95:
prepared according to the synthetic method of compound 1 in example 2, except that reactant a2 is used instead of reactant a1 and intermediate B9 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)58H38N2): theoretical value C, 91.31; h, 5.02; n, 3.67; test values are: c, 91.33; h, 5.01; and N, 3.66. HPLC-MS: the molecular weight of the material is 762.30, and the measured molecular weight is 762.41.
Example 11: synthesis of compound 202:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B10 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)50H32N2): theoretical value C, 90.88; h, 4.88; n, 4.24; test values are: c, 90.89; h, 4.87; and N, 4.23. HPLC-MS: the molecular weight of the material is 660.26, and the measured molecular weight is 660.35.
Example 12: synthesis of compound 219:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B11 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)54H37N3): a theoretical value; c, 89.10; h, 5.12; n, 5.77; test values are: c, 89.12; h, 5.11; and N, 5.76. HPLC-MS: the molecular weight of the material is 727.30, and the measured molecular weight is 727.41.
Example 13: synthesis of compound 301:
prepared according to the synthetic method of compound 1 in example 2, except that reactant A3 is used instead of reactant a1 and intermediate B12 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)56H36N2): theoretical value C, 91.27; h, 4.92; n, 3.80; test values are: c, 90.28; h, 4.93; n, 3.78. HPLC-MS: the molecular weight of the material is 736.29, and the measured molecular weight is 736.37.
Example 14: synthesis of compound 328:
prepared according to the synthetic method for compound 76 in example 2, except that reactant A3 is used instead of reactant a1 and intermediate B13 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)57H36N4): theoretical value C, 88.12; h, 4.67; n, 7.21; test values are: c, 88.14; h, 4.65; and N, 7.20. HPLC-MS: the molecular weight of the material is 776.29, and the measured molecular weight is 776.34.
Example 15: synthesis of compound 364:
prepared according to the synthetic method of compound 1 in example 2, except that reactant a4 is used instead of reactant a1 and intermediate B14 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)57H35N3O): theoretical value C, 88.01; h, 4.54; n, 5.40; o, 2.06; test values are: c, 88.02; h, 4.53; n, 5.39; and O, 2.07. HPLC-MS: the molecular weight of the material is 777.28, and the measured molecular weight is 777.35.
Example 16: synthesis of compound 390:
prepared by the synthetic method of the compound 1 in the example 2With the difference that reactant a4 is substituted for reactant a1 and intermediate B15 is substituted for intermediate B1; 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, 5.01; and N, 3.69. HPLC-MS: the molecular weight of the material is 762.30, and the measured molecular weight is 762.38.
Example 17: synthesis of compound 452:
prepared according to the synthetic method of compound 1 in example 2, except that reactant a2 is used instead of reactant a1 and intermediate B16 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)61H42N2): theoretical value C, 91.24; h, 5.27; n, 3.49; test values are: c, 91.23; h, 5.29; and N, 3.48. HPLC-MS: the molecular weight of the material is 802.33, and the measured molecular weight is 802.43.
Example 18: synthesis of compound 476:
prepared according to the synthetic method of compound 1 in example 2, except that reactant a2 is used instead of reactant a1 and intermediate B17 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)58H38N2): theoretical value C, 91.31; h, 5.02; n, 3.67; test values are: c, 91.30; h, 5.01; and N, 3.69. HPLC-MS: the molecular weight of the material is 762.30, and the measured molecular weight is 762.37.
Example 19: synthesis of compound 575:
prepared according to the synthetic method of compound 1 in example 2, except that reactant a4 is used instead of reactant a1 and intermediate B18 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)58H38N2): theoretical value of C,91.31; h, 5.02; n, 3.67; test values are: c, 91.30; h, 5.04; and N, 3.65. HPLC-MS: the molecular weight of the material is 762.30, and the measured molecular weight is 762.43.
Example 20: synthesis of compound 599:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B19 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)55H39N3): theoretical value C, 89.04; h, 5.30; n, 5.66; test values are: c, 89.06; h, 5.29; and N, 5.65. HPLC-MS: the molecular weight of the material is 741.31, and the measured molecular weight is 741.39.
Example 21: synthesis of compound 702:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B20 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)59H38N2): theoretical value C, 91.44; h, 4.94; n, 3.61; (ii) a Test values are: c, 91.43; h, 4.93; and N, 3.63. HPLC-MS: the molecular weight of the material is 774.30, and the measured molecular weight is 774.42.
Example 22: synthesis of compound 708:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B21 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)65H42N2): theoretical value C, 91.73; h, 4.97; n, 3.29; (ii) a Test values are: c, 91.74; h, 4.98; and N, 3.27. HPLC-MS: the molecular weight of the material is 850.33, and the measured molecular weight is 850.46.
Example 23: synthesis of compound 710:
prepared according to the synthetic method for compound 1 in example 2, except that intermediate B22 is used instead of intermediate B1; elemental analysis Structure (molecular formula C)46H28N2S): theoretical value C, 86.22; h, 4.40; n, 4.37; s, 5.00; test values are: c, 88.59; h, 5.21; n, 6.20; s, 5.00. HPLC-MS: the molecular weight of the material is 640.20, and the measured molecular weight is 640.37.
The compound of the invention can be used in a light-emitting device, can be used as an electron blocking layer material, and can also be used as a host-guest material of a light-emitting layer. The compounds prepared in the above examples of the present invention were tested for thermal performance, T1 energy level, Eg, HOMO energy level and hole mobility, respectively, and the test results are shown in table 2:
TABLE 2
Note: the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the thermogravimetric temperature Td is a temperature at which 1% of the weight loss is observed in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 mL/min; the triplet energy level T1 was measured by Hitachi F4600 fluorescence spectrometer under the conditions of 2X 10-5A toluene solution of (4); the highest occupied molecular orbital HOMO energy level is tested by photoelectron spectroscopy (IPS3) under the atmospheric environment, the hole mobility is tested, the material is made into a single-charge device, and the single-charge device is tested by an SCLC method; using Gaussian16, 6-31G (d) basis set, B3lyp functional and TD-FDT algorithm to optimize the geometrical structure, and calculating the energy levels of HOMO and LUMO, wherein Eg is | HOMO-LUMO |; eg was measured by uv spectroscopy.
The data in the table show that the organic compound has high glass transition temperature, can improve the phase stability of the material film, and further improves 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, can reduce the voltage of a device, has higher band gap width (Eg), and ensures that the material does not absorb in the range of visible light. Therefore, after the pyrene-containing compound is applied to 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 effect of the synthesized OLED material of the present invention in the application of the device is detailed below by device examples 1-57 and comparative example 1. Compared with the device example 1, the device examples 2 to 57 and the comparative example 1 of the present invention have the same manufacturing process, and adopt the same substrate material and electrode material, and the film thickness of the electrode material is also kept consistent, except that the hole transport layer or the electron blocking layer material in the device is replaced. The structural composition of the devices obtained in the respective examples is shown in table 3, and the results of the performance tests of the devices obtained in the respective examples are shown in table 4.
Device example 1
Transparent substrate layer 1/ITO anode layer 2/hole injection layer 3(HAT-CN, thickness 10 nm)/hole transport layer 4 (compound 1, thickness 60 nm)/electron blocking layer 5(EB-1, thickness 20 nm)/light emitting layer 6(GH1, GH2 and GD-1) doped at a weight ratio of 45:45:10, thickness 40 nm)/hole blocking/electron transport layer 7(ET-1 and Liq doped at a weight ratio of 1:1, thickness 40 nm)/electron injection layer 8(LiF, thickness 1 nm)/cathode layer 9(Mg and Ag doped at a weight ratio of 9:1, thickness 15nm)/CPL layer 10 (compound CP-1, thickness 70 nm).
The preparation process comprises the following steps:
as shown in fig. 1, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness of 150nm) is washed, i.e., washed with alkali, washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, HAT-CN having a film thickness of 10nm was deposited by a vacuum deposition apparatus to be used as the hole injection layer 3. Then, compound 1 was evaporated to a thickness of 60nm as a hole transport layer 4. Subsequently, compound EB-1 was evaporated to a thickness of 20nm as an electron blocking layer 5. 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 light emitting layer 6 comprises GH-1 and GH-2 used by the OLED light emitting layer 6 as main materials, GD-1 used as a doping material, the doping proportion of the doping material is 10% by weight, and the thickness of the light emitting layer is 40 nm. After the light-emitting layer 6, the electron transport layer materials ET-1 and Liq are continuously vacuum-evaporated. The vacuum evaporation film thickness of the material was 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 the cathode were connected by a known driving circuit, and the current efficiency of the device and the lifetime of the device were measured, and the results are shown in table 4.
TABLE 3
The inspection data of the obtained electroluminescent device are shown in Table 4.
TABLE 4
Note: LT97 refers to a current density of 10m/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.
From the results in table 4, it can be seen that the pyrene-containing compound prepared by the present invention can be applied to the fabrication of an OLED light-emitting device, and compared with the comparative device example, the efficiency and lifetime of the organic light-emitting device are greatly improved compared with the known OLED material, and especially the lifetime decay of the device is greatly improved.
Further, the efficiency of the OLED device prepared by the material is stable when the OLED device works at low temperature, the efficiency test is carried out on the device examples 3, 15, 35, 43, 53 and 57 and the device comparative example 1 at the temperature range of-10 to 80 ℃, and the obtained results are shown in Table 5 and FIG. 2.
TABLE 5
As can be seen from the data in table 5 and fig. 2, device examples 3, 15, 35, 43, 53, and 57 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.
In summary, the present invention is only a preferred embodiment, and not intended to limit the present invention, and any modifications, equivalents, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. An organic compound containing pyrene, characterized in that the structure of the organic compound is represented by general formula (1):
in the general formula (1), L, L1、L2Each independently represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted dimethylfluorenylene group, a substituted or unsubstituted spirofluorenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted diphenylfluorenylene group, a substituted or unsubstituted naphthyridinylene group, and L, L1May also represent a single bond;
the R represents substituted or unsubstituted C6-30Aryl, 5 to 30 membered heteroaryl containing one or more heteroatoms substituted or unsubstituted;
z is nitrogen atom or C-R1(ii) a Wherein Z at the attachment site is represented as a carbon atom;
z is1-Z8Each independently represents a nitrogen atom or C-R2；
The R is1、R2Each independently represents a hydrogen atom, protium, deuterium, tritium, cyano group, methoxy group, halogen, C1-20Alkyl of (C)2-20Alkenyl of (a), substituted or unsubstituted C6-30Aryl, 5 to 30 membered heteroaryl containing one or more heteroatoms substituted or unsubstituted; and two or more adjacent R2Can be connected with each other to form a ring;
the substituent of the substitutable group is selected from deuterium atom, methoxy group, cyano group, halogen atom, C6-30One or more of aryl, 5-to 30-membered heteroaryl containing one or more heteroatoms;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
2. The organic compound according to claim 1, wherein R represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted azapyrenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted azabenzophenanthryl group, a structure represented by general formula (2), general formula (3), or general formula (4);
said X1、X2、X3Independently represent-O-, -S-, -C (R)3)(R4) -or-N (R)5)-；X2、X3May also represent a single bond;
the Y, Y1、Y2Each independently represents a nitrogen atom or C-R6And Y is1And Y2Can also be connected into a ring;
wherein Y, Y at the connection site1、Y2Represented as a carbon atom;
the R is3～R5Are each independently represented by C1-20Alkyl, substituted or unsubstituted C6-30One of an aryl group, a 5-to 30-membered heteroaryl group substituted or unsubstituted with one or more heteroatoms; r3And R4Can be connected with each other to form a ring;
the R is6Represented by hydrogen atom, protium, deuterium, tritium, cyano, halogen, methoxy, C1-20Alkyl of (C)2-20Alkenyl of (a), substituted or unsubstituted C6-30Aryl, 5 to 30 membered heteroaryl containing one or more heteroatoms substituted or unsubstituted; two or more adjacent R6Can be connected with each other to form a ring;
the substituent of the substitutable group is selected from deuterium atom, methoxy group, cyano group, halogen atom, C6-30Aryl radicals containing one or moreOne or more of a 5 to 30 membered heteroaryl group of heteroatoms;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
3. The organic compound according to claim 2, wherein the general formula (1) can be represented by a structure represented by a general formula (5), a general formula (6), or a general formula (7);
4. the organic compound according to claim 1, wherein the general formula (1) can be represented by a structure represented by general formula (8), general formula (9), general formula (10), or general formula (11);
5. the organic compound of claim 2, wherein Y, Z is the compound1-Z8The number of nitrogen atoms is 0, 1 or 2.
6. The organic compound of claim 2, wherein R is1、R2、R6Each independently represents a hydrogen atom, protium, deuterium, tritium, fluorine atom, cyano group, methoxy group, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted furyl group, substituted or unsubstituted dibenzofuryl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted naphthyridinyl groupOne of (1);
the R is3～R5Each independently represents one of methyl, ethyl, propyl, isopropyl, tert-butyl, amyl, phenyl, naphthyl, biphenyl, naphthyridinyl or pyridyl;
the substituent of the substitutable group is one or more selected from fluorine atom, methoxy group, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, amyl group, phenyl group, naphthyl group, biphenyl group, naphthyridinyl group or pyridyl group.
7. The organic compound of any one of claims 1-6, wherein the compound has the specific structure:
8. An organic electroluminescent element, characterized in that at least one functional layer of the organic electroluminescent element contains the pyrene-containing organic compound according to any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, comprising a hole transport layer or an electron blocking layer, wherein the hole transport layer or the electron blocking layer contains the pyrene-containing organic compound according to any one of claims 1 to 7.
10. A lighting or display element comprising the organic electroluminescent device according to any one of claims 8 or 9.
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| KR20200144482A (en) * | 2019-06-18 | 2020-12-29 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| KR102420146B1 (en) | 2019-06-18 | 2022-07-12 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| CN112142647A (en) * | 2020-09-30 | 2020-12-29 | 南京艾姆材料科技有限公司 | Asymmetric triarylamine |
| CN112961131A (en) * | 2021-02-04 | 2021-06-15 | 吉林奥来德光电材料股份有限公司 | Organic compound, preparation method and application thereof |
| CN115160272A (en) * | 2021-09-15 | 2022-10-11 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, and electronic element and electronic device using same |
| CN115160272B (en) * | 2021-09-15 | 2023-10-31 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, and electronic element and electronic device using same |
| CN116023353A (en) * | 2021-10-25 | 2023-04-28 | 奥来德(上海)光电材料科技有限公司 | Light-emitting auxiliary material, preparation method thereof, organic electroluminescent device and application thereof |
| WO2023085877A1 (en) * | 2021-11-15 | 2023-05-19 | 주식회사 엘지화학 | Compound and organic light-emitting element comprising same |
| CN114106001A (en) * | 2021-11-30 | 2022-03-01 | 武汉天马微电子有限公司 | Heterocyclic compound containing heteroatom substituted fluorene and application thereof in photoelectric device |
| CN114805373A (en) * | 2022-02-25 | 2022-07-29 | 京东方科技集团股份有限公司 | Hole transport material, light-emitting device, display panel and display device |
| CN114805373B (en) * | 2022-02-25 | 2023-10-24 | 京东方科技集团股份有限公司 | Hole transport material, light emitting device, display panel and display device |
| WO2023244000A1 (en) * | 2022-06-15 | 2023-12-21 | 주식회사 엘지화학 | Compound and organic light-emitting element comprising same |
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