CN113735870B - Compound with nitrogen-containing hetero-structure and application thereof - Google Patents
Compound with nitrogen-containing hetero-structure and application thereof Download PDFInfo
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Abstract
The invention relates to a compound containing a nitrogen-containing hetero-structure, which belongs to the field of organic electroluminescence and has a molecular general formula shown in a structural formula I]Shown in the specification:
wherein [ structural formula I ]]In the formula, R represents one of phenyl, biphenyl, substituted or unsubstituted C10-C14 condensed ring aryl or furyl, thienyl, anthryl, phenanthryl, naphthyl, phenylcarbazole, pyrene, methylfluorene and phenylfluorene. The compound containing the azepine structure is applied to an organic electroluminescent device. The compound is a derivative formed by connecting an azepine-containing structure with fluorene and the like, and the nitrogenous seven-membered ring mechanism blocks the conjugation of a benzene ring, so that the triplet state of molecules is maintained, the triplet state energy level is higher, the energy transfer is more sufficient, the transfer of electrons and holes is more balanced, and the efficiency and the service life of the device are higher.
Description
Technical Field
The invention relates to a compound containing a nitrogen-containing hetero-structure and application thereof, belonging to the technical field of organic electroluminescence.
Background
Organic light-emitting devices (OLEDs) have become a research focus in the field of flat panel information display. The OLED has the advantages of being flat, self-luminous, rich in colors, fast in response, wide in visual field, easy to realize ultrathin, light and the like, is considered as a new technology which is most likely to replace liquid crystal displays and plasma displays in the future, and can be used as lighting and backlight sources. However, the disadvantages of high manufacturing cost and low yield are to be solved. The OLED display technology is different from the conventional LCD display mode in that a backlight is not required, and a very thin organic material coating and a glass substrate are used, and when a current flows, the organic material emits light. Moreover, the OLED display screen can be made lighter and thinner, the visual angle is larger, and the electric energy can be obviously saved.
The basic structure of OLED is a sandwich structure composed of a thin and transparent Indium Tin Oxide (ITO) with semiconductor characteristics, which is connected to the positive electrode of power, and another metal cathode. The whole structure layer comprises: a Hole Transport Layer (HTL), an Emission Layer (EL), and an Electron Transport Layer (ETL). When power is supplied to a proper voltage, positive holes and negative charges combine in the light-emitting layer to generate light, which generates three primary colors of red, green and blue RGB according to different formulas to form basic colors. The OLED has the characteristics of self-illumination, unlike the TFT LCD that requires a backlight, and thus has high visibility and brightness, and the advantages of low voltage requirement, high power saving efficiency, fast response, light weight, thin thickness, simple structure, low cost, etc., and is considered to be one of the most promising products in the 21 st century. However, when an OLED device is operated by applying a voltage, joule heat is generated, so that organic materials are easily crystallized, which affects the lifetime and efficiency of the device. Therefore, development of stable and efficient organic electroluminescent materials is also required.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a compound containing a nitrogen and azepine structure and application thereof, wherein the compound containing the nitrogen and azepine structure can improve the efficiency and prolong the service life of an organic electroluminescent device.
The technical scheme for solving the technical problems is as follows: a compound containing a nitrogen-containing hetero-structure, wherein the molecular general formula of the compound is shown as [ structural formula I ]:
in the structural formula I, R represents one of phenyl, biphenyl, substituted or unsubstituted C10-C14 condensed ring aryl or furyl, thienyl, anthryl, phenanthryl, naphthyl, phenylcarbazole, pyrene, methylfluorene and phenylfluorene.
Preferably, the compound is selected from any one of the following chemical formulas [2-1] to [2-10 ]:
wherein X is selected from H or CN, and Y is independently selected from O or S.
Preferably, the compound is selected from any one of the following chemical formulas [3-1] to [3-35 ]:
the invention also discloses an application of the compound containing the azepine structure, which comprises the following steps: the compound containing the azepine structure is applied to an organic electroluminescent device, one compound can be used as the compound represented by the structural formula I, and two or more compounds in the structural formula I can also be used at the same time.
Furthermore, the organic electroluminescent device comprises a cathode layer, an anode layer and an organic layer, wherein the compound containing the azepine structure is applied to the organic layer, and the organic layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron injection layer and an electron transport layer.
Further, the organic layer comprises a light emitting layer, the compound containing the azepine structure is applied to the light emitting layer, the light emitting layer is a blue light emitting layer, and the compound containing the azepine structure is used as a blue main body, so that the organic electroluminescent device with high efficiency, high resolution, high brightness and long service life can be obtained.
Further, the organic layer comprises an electron transport layer, and the compound containing the azepine structure is applied to the electron transport layer.
Further, the organic layer comprises a light emitting layer and an electron transport layer, both the light emitting layer and the electron transport layer contain the compound, and the compounds with the nitrogen-containing hetero structure in the light emitting layer and the electron transport layer are the same or different.
Further, the compound containing the azepine structure is applied to an organic electroluminescent device, and the compound containing the azepine structure is used alone or mixed with other compounds.
The beneficial effects of the invention are:
the compound containing the azepine structure has the characteristics that the efficiency, the thermal stability and other performances of a device can be improved, the synthetic route of the compound containing the azepine structure is relatively simple, the reaction steps can be shortened, the reaction yield is improved, and the synthetic cost is reduced;
the compound containing the azepine structure is applied to a light-emitting layer in an OLED device and used as a blue light material, the compound is a derivative formed by connecting a nitrogen-containing azepine structure with fluorene and the like, and the nitrogen-containing heptatomic ring mechanism blocks the conjugation of a benzene ring, so that the triplet state of molecules is maintained, the triplet state energy level is higher, the energy transfer is more sufficient, the transfer of electrons and holes is more balanced, and the efficiency and the service life of the organic electroluminescent device are higher.
Drawings
FIG. 1 is a diagram of a structure layer of an organic electroluminescent device according to an embodiment;
in the figure, 1 substrate, 2 anode, 3 hole injection layer, 4 hole transport layer, 5 luminescent layer, 6 hole blocking layer, 7 electron transport layer, 8 electron injection layer, 9 cathode.
Detailed Description
The present invention will be described in detail with reference to the following embodiments in order to make the above objects, features and advantages of the present invention more comprehensible. In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein, as those skilled in the art will recognize without departing from the spirit and scope of the present invention.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
Synthesis example
1. Preparation of intermediate M-1:
under the protection of nitrogen, 10.0g of 2-bromo-3-fluoro dibenzofuran, 6.0g of carbazole, 18.4g of cesium carbonate and 60mL of N, N-dimethylformamide are added into a reaction bottle, and the mixture is heated, refluxed and insulated for 12 hours. After the reaction is completed, adding toluene to extract organic phase, after the reaction water phase is extracted by using toluene, combining organic phases, and washing by using purified water until the organic phase is identical. After the washing with water, the mixture was dried, passed through a column, desolventized, and recrystallized from toluene/ethanol to obtain 10g of a pale yellow solid with a yield of 65%. This pale yellow solid was identified as intermediate M-1 according to LC-MS analysis. LC-MS: M/Z412.28.
2. Preparation of intermediate M-2:
under the protection of nitrogen, adding M-110 g, 7.4g of diboronic acid pinacol ester, 7g of potassium acetate, 0.56g of [1, 1' -bis (diphenylphosphino) ferrocene ] palladium (II) dichloride and 100mL of xylene into a reaction bottle, and heating, refluxing and preserving heat for 10 hours. After the reaction is completed, standing and layering are carried out, the upper organic phase is washed to be neutral, and after the washing, the white solid 6g is obtained by drying, column passing, solvent removal and toluene/ethanol recrystallization, and the yield is 55%. This white solid was identified as intermediate M-2 according to LC-MS analysis. LC-MS M/Z459.34.
3. Preparation of intermediate M-3:
under the protection of nitrogen, adding M-213.8g, 10g of 1-bromo-4-chloro-2-iodobenzene, 3.5g of potassium hydroxide, 10.5g of purified water, 0.45g of tetrakis (triphenylphosphine) palladium and 80mL of toluene into a reaction bottle, heating to 70-80 ℃, keeping the temperature for 12 hours, after the reaction is finished, adding toluene for extraction and washing until an organic phase is neutral, and drying, passing through a column, removing a solvent and recrystallizing toluene/ethanol to obtain 7.8g of white-like solid, wherein the yield is as follows: 50 percent. According to LC-MS analysis, this white solid was identified as intermediate M-3, LC-MS: M/Z522.82.
4. Preparation of intermediate M-4:
under the protection of nitrogen, M-310 g, palladium acetate 0.1g, tricyclohexylphosphine tetrafluoroborate 0.3g, potassium carbonate 2.1g and N, N-dimethylformamide 80mL are added into a reaction bottle, and the temperature is raised to 130.0 ℃ and kept for 6 h. After the reaction is finished, adding toluene for extraction, washing with water to be neutral, drying, passing through a column, removing a solvent, and recrystallizing toluene/ethanol to obtain a white-like solid 3.4g, wherein the yield is as follows: 40 percent. According to LC-MS analysis, the white solid was identified as intermediate M-4, LC-MS: M/Z441.91.
Examples
1. Preparation of Compound 3-1
Under the protection of nitrogen, adding M-410 g, phenylboronic acid 2.7g, dichloro di-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (II)0.3g, potassium hydroxide 2.1g, purified water 6.3g and dioxane 80mL into a reaction bottle, heating to 70-80 ℃, keeping the temperature for 6 hours, standing for layering after the reaction is finished, washing an organic phase to be neutral, drying, passing through a column, removing a solvent, and recrystallizing toluene/ethanol to obtain white-like solid 6.4g, wherein the yield is as follows: 60 percent. According to LC-MS analysis, the white solidThe compound is identified as 3-1, LC-MS: M/Z483.56, and the NMR test result of the compound 3-1 is as follows:1HNMR(CDCl3):δ7.53-7.80(8H,7.59(tdd,J＝6.5,2.2,1.5Hz),7.65(ddd,J＝8.0,5.1,1.8Hz),7.66(dddd,J＝7.6,6.5,1.8,0.5Hz),7.71(ddd,J＝8.0,5.8,2.0Hz),7.72(t,J＝5.1Hz),7.74(ddd,J＝5.7,5.0,1.7Hz),7.73(d,J＝0.5Hz)),7.84-8.57(10H,7.91(dddd,J＝7.6,1.8,1.5,0.5Hz),7.95(ddd,J＝5.0,1.8,0.5Hz),8.04(ddd,J＝5.7,5.0,1.8Hz),8.13(ddd,J＝5.8,1.8,0.5Hz),8.25(ddd,J＝5.1,2.0,0.5Hz),8.27(dd,J＝5.1,2.0Hz),8.33(dd,J＝5.5,2.0Hz),8.42(ddt,J＝5.1,2.0,0.5Hz),8.51(ddt,J＝5.0,1.7,0.5Hz)),8.71(1H,dd,J＝5.5,0.5Hz),8.94(1H,dd,J＝2.0,0.5Hz),9.08(1H,t,J＝0.5Hz)。
2. preparation of Compounds 3-15
Under the protection of nitrogen, adding 4.7g of M-410 g, 4-boric acid dibenzofuran, 0.3g of dichloro-di-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (II), 2.1g of potassium hydroxide, 6.3g of purified water and 80mL of dioxane into a reaction bottle, heating to 70-80 ℃, preserving heat for 6 hours, standing for layering after reaction, washing an organic phase to be neutral, drying, passing through a column, removing a solvent, and recrystallizing toluene/ethanol to obtain 8.3g of white-like solid, wherein the yield is as follows: 65 percent. According to LC-MS analysis, this white solid was identified as compound 3-15, LC-MS: M/Z573.64. The results of NMR tests on the compounds 3-15 are as follows:1HNMR(CDCl3):δ7.59-8.08(12H,7.65(ddd,J＝7.9,5.1,1.8Hz),7.72(ddd,J＝7.9,5.9,1.9Hz),7.74(t,J＝5.1Hz),7.75(ddd,J＝6.9,5.1,1.7Hz),7.78(ddd,J＝5.2,5.0,1.7Hz),7.82(d,J＝0.5Hz),7.88(dd,J＝8.5,1.9Hz),7.92(dd,J＝8.5,5.1Hz),7.96(ddd,J＝6.9,5.1,1.6Hz),7.97(ddd,J＝5.1,1.6,0.5Hz),7.99(ddd,J＝5.0,1.9,0.5Hz),8.01(ddd,J＝5.2,5.0,1.9Hz)),8.09-8.33(3H,8.15(ddd,J＝5.9,1.8,0.5Hz),8.26(dd,J＝5.1,1.9Hz),8.27(ddd,J＝5.1,1.9,0.5Hz)),8.33-8.66(6H,8.39(dd,J＝5.5,2.0Hz),8.43(ddt,J＝5.1,1.9,0.5Hz),8.46(ddd,J＝5.1,1.9,0.5Hz),8.47(ddt,J＝5.1,1.7,0.5Hz),8.54(ddt,J＝5.0,1.7,0.5Hz),8.60(dd,J＝5.5,0.5Hz)),8.96(1H,dd,J＝2.0,0.5Hz),9.08(1H,t,J＝0.5Hz)。
3. preparation of Compounds 3 to 25
Under the protection of nitrogen, adding M-410 g, 8.2g of 9-phenyl-3-boric acid-9H-carbazole, 0.3g of dichloro di-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (II), 2.1g of potassium hydroxide, 3.6g of purified water and 80mL of dioxane into a reaction bottle, heating to 70-80 ℃, preserving heat for 6 hours, standing for layering after the reaction is finished, washing an organic phase to be neutral, drying, passing through a column, removing a solvent, and recrystallizing toluene/ethanol to obtain 8.6g of white-like solid, wherein the yield is as follows: 60 percent. According to LC-MS analysis, the white solid is identified as a compound 3-25, LC-MS: M/Z648.75, and the compound 3-25 has the following results after NMR test:1HNMR(CDCl3):δ7.46-7.89(10H,7.53(tdd,J＝6.7,1.9,1.5Hz),7.62(dddd,J＝7.7,6.7,1.7,0.4Hz),7.70(ddd,J＝7.0,5.1,1.8Hz),7.73(t,J＝5.1Hz),7.74(ddd,J＝7.0,5.1,1.9Hz),7.76(ddd,J＝7.9,5.9,1.9Hz),7.77(ddd,J＝7.9,5.1,1.9Hz),7.78(ddd,J＝5.3,5.0,1.7Hz),7.84(d,J＝0.5Hz)),7.93-8.08(3H,8.00(dtd,J＝7.7,1.7,0.4Hz),8.02(ddd,J＝5.3,5.1,1.9Hz)),8.15-8.72(13H,8.21(ddd,J＝5.9,1.9,0.5Hz),8.23(dd,J＝5.1,1.9Hz),8.24(ddd,J＝5.0,1.9,0.5Hz),8.25(ddd,J＝5.1,1.9,0.5Hz),8.27(dd,J＝5.5,2.0Hz),8.29(dd,J＝5.5,2.0Hz),8.30(ddd,J＝5.1,1.8,0.5Hz),8.41(dd,J＝5.5,0.4Hz),8.42(ddt,J＝5.1,1.9,0.5Hz),8.45(ddt,J＝5.1,1.9,0.5Hz),8.54(ddt,J＝5.1,1.7,0.5Hz),8.62(dd,J＝5.5,0.5Hz),8.67(dt,J＝2.0,0.5Hz)),8.89(1H,dd,J＝2.0,0.5Hz),9.07(1H,t,J＝0.5Hz)。
4. preparation of Compounds 3-1 to 3-35
The preparation method of the compound 3-1-3-35 is the same as the preparation method of the compound 3-15, and the used raw materials are the intermediate M-4 and other boric acid raw materials, and are specifically shown in the following table:
15 organic electroluminescent devices are prepared in a thermal evaporation mode, and each specific device structure is as follows:
device embodiment:
coating with a thickness of
The ITO glass substrate 1 of (1) was cleaned in distilled water for 2 times, ultrasonically cleaned for 30 minutes, and repeatedly cleaned with distilled water for 2 times, ultrasonically cleaned for 10 minutes, and after the cleaning with distilled water was completed, the substrate was ultrasonically cleaned with solvents of isopropyl alcohol, acetone, and methanol in this order, and then dried, and the dried substrate 1 was transferred to a plasma cleaning machine, and the substrate 1 was cleaned for 5 minutes and then transferred to an evaporation plating machine.
ITO cleaned is used as a substrate 1, the substrate 1 is provided with an anode 2 surface, and a hole injection layer 3 is sequentially evaporated on the anode 2 surface (2-TNATA evaporation thickness is
) Hole transport layer 4(a-NPD vapor deposition thickness of
) A light-emitting layer 5(ADN (9, 10-di (2-naphthyl) anthracene) and 5% of EGl-EG 3 or any of the compounds of the present invention deposited to a thickness of
) A hole blocking layer 6 and an electron transport layer 7(TPBi of vapor deposition thickness of
) An electron injection layer 8 (thickness of LiF vapor deposition
) And A1 is evaporated to a thickness of
Forming a cathode 9; the organic matter evaporation speed is maintained in the above process
The evaporation rate of LiF is
A1 vapor deposition rate of
The performance test results of the organic light emitting devices prepared in the device example and the comparative experiment example are as follows:
from the results in the table, when the compound for the organic electroluminescent device provided by the invention is used for preparing the organic electroluminescent device, the luminous efficiency and the service life of the organic electroluminescent device are obviously improved.
All possible combinations of the technical features of the above embodiments may not be described for the sake of brevity, but should be considered as within the scope of the present disclosure as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that various changes and modifications can be made by those skilled in the art without departing from the spirit of the invention, and these changes and modifications are all within the scope of the invention. Therefore, the protection scope of the present patent should be subject to the appended claims.
Claims (8)
1. A compound having a nitrogen-containing hetero-structure, wherein the compound is selected from any one of the following chemical formulas [2-1] to [2-10 ]:
wherein X is selected from H or CN, and Y is independently selected from O or S.
2. The compound having a nitrogen-containing azepine structure according to claim 1, wherein the compound is selected from any one of the following chemical formulas [3-1] to [3-35 ]:
3. use of a compound containing a nitrogen-containing azepine structure according to any one of claims 1-2 in an organic electroluminescent device.
4. The use of the compound containing an azepine structure as claimed in claim 3, wherein the organic electroluminescent device comprises a cathode layer, an anode layer and an organic layer, the compound containing an azepine structure is used in the organic layer, and the organic layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron injection layer and an electron transport layer.
5. The use of the compound containing the azepine structure according to claim 4, wherein the organic layer comprises a light-emitting layer, the compound containing the azepine structure is used in the light-emitting layer, the light-emitting layer is a blue light-emitting layer, and the compound containing the azepine structure is used as a blue host.
6. The use of the compound containing the azepine structure in the claim 4, wherein the organic layer comprises an electron transport layer, and the compound containing the azepine structure is applied to the electron transport layer.
7. The use of the compound containing a nitrogen-containing azepine structure as claimed in claim 4, wherein the organic layer comprises a light-emitting layer and an electron transport layer, the light-emitting layer and the electron transport layer both contain the compound, and the compound containing a nitrogen-containing azepine structure in the light-emitting layer and the electron transport layer is the same or different.
8. The use of the compound containing the azepine structure according to claim 3, wherein the compound containing the azepine structure is used in an organic electroluminescent device, and the compound containing the azepine structure is used alone or in a mixture with other compounds.
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