CN115490656A - Luminous auxiliary material and preparation method thereof, light-emitting device and light-emitting device - Google Patents

Luminous auxiliary material and preparation method thereof, light-emitting device and light-emitting device Download PDF

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CN115490656A
CN115490656A CN202211452628.6A CN202211452628A CN115490656A CN 115490656 A CN115490656 A CN 115490656A CN 202211452628 A CN202211452628 A CN 202211452628A CN 115490656 A CN115490656 A CN 115490656A
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light
luminescent
nitrogen
auxiliary material
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CN115490656B (en
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汪康
李贺
赵贺
王聪聪
黄悦
王士凯
顾鑫
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The luminescent auxiliary material is obtained by connecting groups such as triarylamine and the like with a dibenzofuran main body structure, on one hand, the triarylamine structure has a nitrogen atom containing lone pair electrons, the electrons on the nitrogen atom are transferred in a transition mode under the action of an external electric field, and the molecules generate holes, so that the reverse transfer of the holes is realized; on the other hand, the triarylamine has good hole transport capability, furan derivative groups are weak electron supply groups, the triarylamine compound provided by the application is formed by connecting furan derivative groups on a triarylamine main body structure, geometric structures are added on the basis of a non-planar molecular structure, a compound with a large space configuration is formed, and the unique structure of the triarylamine compound is beneficial to hole transport, so that high hole transport efficiency is obtained, the luminous efficiency and the service life of a device are improved, and the driving voltage is reduced.

Description

Luminous auxiliary material and preparation method thereof, light-emitting device and light-emitting device
Technical Field
The application belongs to the technical field of materials, and particularly relates to a luminous auxiliary material, a preparation method thereof, a luminous device and a luminous device.
Background
Small molecule green organic electroluminescent devices (OLEDs) were first developed in 1987 by Tang et al, of the Istman Kodak company (Eastman Kodak), by using a TPD/ALq3 bilayer consisting of a light-emitting layer and a charge transport layer. Since then, the development of OLEDs has been rapidly affected and OLEDs have been commercialized. An organic electroluminescent device converts electrical energy into light by applying power to an organic light emitting material, and generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layers of the OLED may include a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, an electron blocking layer, a light emitting layer (containing host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. Materials used in the organic layer may be classified into a hole injection material, a hole transport material, a hole assist material, a light emission assist material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, and the like according to functions.
The light-emitting auxiliary layer is arranged between the hole transport layer and the light-emitting layer, and can play a role in reducing potential barrier between the hole transport layer and the light-emitting layer and reducing the driving voltage of the organic electroluminescent device, so that the utilization rate of holes is further increased, the light-emitting efficiency and the service life of the device are improved, and the driving voltage is reduced. However, there are few functional materials that can form the light-emitting auxiliary layer, and particularly, the light-emitting auxiliary layer material is in the form of an amorphous disordered thin film in a vapor deposition device, and the form of the thin film formed by vapor deposition affects the vapor deposition temperature, the lifetime of the OLED device, and the light-emitting efficiency. Therefore, it is very important to develop organic functional materials with higher performance to meet the requirements of panel manufacturing enterprises in mass production of organic electroluminescent displays.
Disclosure of Invention
The application aims to provide a luminescent auxiliary material, and aims to solve the problems that the existing luminescent auxiliary material is low in hole mobility and influences the service life and the luminous efficiency of a device.
The application is realized by the following steps that the luminous auxiliary material has a structural formula shown in a chemical formula I:
Figure 755282DEST_PATH_IMAGE001
wherein L is selected from a single bond, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3-to 30-membered heteroaryl group, the heteroatoms of which are selected from oxygen, nitrogen, sulfur;
Ar 1 selected from the following groups or combinations thereof:
Figure 973774DEST_PATH_IMAGE002
；
n independently represents an integer of 1 to 4;
Ar 2 independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted (C10-C30) fused ring, substituted or unsubstituted 3-to 30-membered heteroaryl, wherein the heteroatoms are selected from oxygen, nitrogen, sulfur, or; wherein Ar is 2 When the N-substituted phenyl ring is connected with the benzene ring, the N-substituted phenyl ring is not connected with the ortho-position of the connection of the N-substituted phenyl ring and the benzene ring;
ring A is a substituent fused on a benzene ring, can be fused with 1, 2-position and 2, 3-position of the benzene ring, and is selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted 3-30-membered heteroaryl, and heteroatoms of the heteroaryl are selected from oxygen, nitrogen and sulfur;
the substituents include: hydrogen, deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl, C6-C12 heteroaryl, wherein the heteroatoms are selected from oxygen, nitrogen, sulfur; wherein said C1-C6 alkyl represents methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl; the aryl of C6-C12 represents phenyl, biphenyl and naphthyl; the heteroaryl of C6-C12 represents dibenzothiophene and dibenzofuran.
Another object of the present application is a method for preparing a luminescence support material, comprising:
Figure 505249DEST_PATH_IMAGE003
dissolving a raw material A in anhydrous tetrahydrofuran, adding n-BuLi under the protection of nitrogen for reaction, continuing adding an iodine-containing tetrahydrofuran solution for reaction, and adding a sodium thiosulfate aqueous solution for liquid separation after the reaction is finished to obtain an intermediate 1;
dissolving the intermediate 1 and the raw material B in a mixed solution of toluene, ethanol and water, adding a palladium catalyst and salt under the protection of nitrogen, uniformly stirring, heating to 80-100 ℃, and refluxing for 5-7 hours to obtain an intermediate 2;
dissolving the intermediate 2 and the raw material C in a toluene solution, adding a palladium catalyst, a phosphorus ligand and a salt in a nitrogen atmosphere, heating to 90-115 ℃, and stirring for reacting for 4-12h to obtain an intermediate 3;
dissolving the intermediate 3 and the raw material D in a mixed solution of toluene, ethanol and water, adding a palladium catalyst and salt under the protection of nitrogen, and uniformly stirring to obtain an intermediate 4;
dissolving the intermediate 4 and the raw material E in a toluene solution, adding a palladium catalyst, a phosphorus ligand and a salt in a nitrogen atmosphere, heating to 90 ℃, and stirring for reacting for 4-12 hours to obtain an intermediate 5;
and dissolving the intermediate 5 and the raw material F in a toluene solution, adding a palladium catalyst, a phosphorus ligand and a salt in a nitrogen atmosphere, heating to 90-120 ℃, and stirring for reacting for 4-12h to obtain the luminescent auxiliary material shown in the chemical formula I.
Another object of the present application is a light emitting device comprising said luminescent auxiliary material.
Another object of the present application is a light emitting device comprising said light emitting device.
The luminescent auxiliary material is obtained by connecting groups such as triarylamine and the like with a dibenzofuran main body structure, on one hand, the triarylamine structure has a nitrogen atom containing lone pair electrons, and the electrons on the nitrogen atom are transferred in a transition mode under the action of an external electric field, so that the molecules generate holes, and the reverse transfer of the holes is realized; on the other hand, the triarylamine compound has good hole transport capacity, furan derivative groups are weak electron supply groups, the triarylamine compound is formed by connecting furan derivative groups on a triarylamine main body structure, geometric structures are added on the basis of a non-planar molecular structure, a compound with a large space configuration is formed, and the unique structure of the triarylamine compound is beneficial to hole transport, so that high hole transport efficiency is obtained, the luminous efficiency and the service life of a device are improved, and the driving voltage is reduced.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of Compound 1 provided in the examples herein;
figure 2 is a nuclear magnetic resonance hydrogen spectrum of compound 53 provided in the examples herein.
Detailed Description
In order to make the objects, technical solutions and advantages of the present application more apparent, the present application is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the present application and are not intended to limit the present application.
The application provides a luminescent auxiliary material, the structural formula of which is shown as chemical formula (I):
Figure 395976DEST_PATH_IMAGE004
l is selected from a single bond, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, the heteroatom of which is selected from oxygen, nitrogen, sulfur;
Ar 1 selected from the following groups or combinations thereof:
Figure 100627DEST_PATH_IMAGE005
；
n independently represents an integer of 1 to 4;
ar2 is independently selected from hydrogen, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl, the heteroatoms of which are selected from oxygen, nitrogen, sulfur; a substituted or unsubstituted (C10-C30) fused ring group; wherein, when Ar2 is connected with the benzene ring, the connection position of the benzene ring and N is not connected.
The ring A is a substituent fused on a benzene ring, can be fused with 1, 2-position and 2, 3-position of the benzene ring, and is selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted 3-to 30-membered heteroaryl, and the heteroatom of the heteroaryl is selected from oxygen, nitrogen and sulfur.
More preferably, ring a is phenyl.
Further preferably, L is selected from a single bond, and the following groups or combinations thereof:
Figure 908046DEST_PATH_IMAGE006
。
further preferably, ar 2 Selected from hydrogen, and the following groups or combinations thereof:
Figure 407160DEST_PATH_IMAGE007
；
wherein in the above formula, is represented as a connecting point.
More preferably, the structural formula of the luminescence auxiliary material is represented by chemical formulas I-1-I-2:
Figure 785183DEST_PATH_IMAGE008
；
wherein L and Ar in the above chemical formulas I-1 to I-2 1 、Ar 2 N is as defined above.
In the above-mentioned terms of the present application, "substituted" means that a hydrogen atom bonded to a carbon atom of a compound becomes another substituent, and the substituted position is not limited as long as the position is a position at which the hydrogen atom is substituted (i.e., a position at which the substituent may be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other. The substituent comprises: hydrogen, deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl, C6-C12 heteroaryl, wherein the heteroatoms are selected from oxygen, nitrogen, sulfur; wherein C1-C6 alkyl represents methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl; C6-C12 aryl represents phenyl, biphenyl, naphthyl; C6-C12 heteroaryl represents dibenzothiophene or dibenzofuran.
In the above technical solution, it is further preferable that the luminescence auxiliary material is any one of the following structures, but not limited thereto:
Figure 27946DEST_PATH_IMAGE009
Figure 424292DEST_PATH_IMAGE010
Figure 828729DEST_PATH_IMAGE011
Figure 691118DEST_PATH_IMAGE012
Figure 471992DEST_PATH_IMAGE013
Figure 988424DEST_PATH_IMAGE014
Figure 829341DEST_PATH_IMAGE015
Figure 447535DEST_PATH_IMAGE016
Figure 32100DEST_PATH_IMAGE017
Figure 137460DEST_PATH_IMAGE018
Figure 414857DEST_PATH_IMAGE019
Figure 989189DEST_PATH_IMAGE020
。
the luminescence auxiliary materials of the present application can be prepared by synthetic methods known to those skilled in the art. For example, the following reaction scheme is preferred for preparation.
Figure 377445DEST_PATH_IMAGE021
Description of the invention: relative to the complex starting materials E and F, which are not disclosed, the synthesis will be carried out by classical Suzuki coupling and/or Buchwald-Hartwig coupling and will be applied to the present application.
In the above formula, rings A, L and Ar 1 、Ar 2 Hal is as defined in formula I above 1 -Hal 4 Each independently selected from fluorine, chlorine, bromine or iodine.
Dissolving the raw material A (1.0 eq) in anhydrous tetrahydrofuran 400ML, stirring at room temperature to completely dissolve, cooling to-72 ℃ under the protection of nitrogen, stirring for 30 minutes, adding n-BuLi (1.1 eq) to react for 2 hours, then heating to-40 ℃ to react for 1 hour, and cooling to-72 ℃. Iodine (2.0 eq) was dissolved in tetrahydrofuran solution, and the iodine-containing solution was added dropwise to the above solution, and the reaction solution was brown, gradually warmed to room temperature and left overnight. Adding (3.0 eq) sodium thiosulfate aqueous solution, stirring for 30 minutes, standing, separating liquid to obtain an organic layer, extracting a water layer once by using ethyl acetate, combining the organic layers, drying for 10 minutes by using anhydrous magnesium sulfate, filtering, spin-drying to obtain a white solid, passing through a silica gel column, washing the column by using petroleum ether, and finally obtaining a white product intermediate 1.
Dissolving an intermediate 1 (1.0 eq) in a mixed solution of toluene, ethanol and water (the volume ratio of toluene, ethanol and water is 3; after the organic phases were combined, dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic substance. And (3) completely dissolving the solid organic matter by using dichloromethane, slowly dripping the dissolved organic matter into a petroleum ether solution, uniformly stirring, separating out a precipitate, performing suction filtration to obtain a solid, sequentially leaching by using absolute ethyl alcohol and petroleum ether, and drying to prepare an intermediate 2.
Intermediate 2 (1.0 eq) was dissolved in toluene solution, starting material C (1.0 eq) was dissolved in toluene solution, and the solution of starting material C was slowly added to the solution of intermediate 2, in N 2 Adding palladium catalyst (0.01 eq), phosphorus ligand (0.05 eq) and salt (2.0 eq) under atmosphere, heating to 90-115 deg.C, stirring, reacting for 4-12h, vacuum-filtering with diatomite while hot after reaction, removing salt and catalyst, cooling filtrate to room temperature, adding distilled water into filtrate, washing, separating, retaining organic phase, and adding ethyl acetateThe aqueous phase was extracted, and the combined organic layers were dried over magnesium sulfate and the solvent was removed using a rotary evaporator. Finally the remaining material was purified by column chromatography using a mixture of dichloromethane and petroleum ether as eluent to give intermediate 3.
Dissolving an intermediate 3 (1.0 eq) in a mixed solution of toluene, ethanol and water (the volume ratio of toluene, ethanol and water is 3; after the organic phases were combined, dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic substance. And (3) completely dissolving the solid organic matter by using dichloromethane, slowly and dropwisely adding the dissolved solid organic matter into a petroleum ether solution, uniformly stirring, precipitating, carrying out suction filtration to obtain a solid, sequentially leaching by using absolute ethyl alcohol and petroleum ether, and drying to prepare an intermediate 4.
Intermediate 4 (1.0 eq) was dissolved in toluene solution, starting material E (1.0 eq) was dissolved in toluene solution, and then the solution of starting material E was slowly added to the solution of intermediate 4 in N 2 Adding a palladium catalyst (0.01 eq), a phosphorus ligand (0.05 eq) and salt (2.0 eq) under an atmosphere, heating to 90 ℃, stirring for reacting for 4-12 hours, carrying out suction filtration by using diatomite while hot after the reaction is finished, removing the salt and the catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, drying a combined organic layer by using magnesium sulfate, and removing the solvent by using a rotary evaporator. Finally the remaining material was purified by column chromatography using a mixture of dichloromethane and petroleum ether as eluent to give intermediate 5.
Dissolving the intermediate 5 (1.0 eq) in a toluene solution, dissolving the starting material F (1.0 eq) in a toluene solution, and slowly adding the solution of the starting material F to the toluene solutionSolution of intermediate 5 in N 2 Adding a palladium catalyst (0.01 eq), a phosphorus ligand (0.05 eq) and salt (2.0 eq) under an atmosphere, heating to 90-120 ℃, stirring and reacting for 4-12h, performing suction filtration by using diatomite while hot after the reaction is finished, removing the salt and the catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, drying the combined organic layer by using magnesium sulfate, and removing the solvent by using a rotary evaporator. Finally, the remaining material was purified by column chromatography using a mixture of dichloromethane and petroleum ether as eluent to give formula I.
Specifically, the raw material E and the raw material F can be prepared by C — C coupling reaction of Suzuki, for example, the raw material F is obtained by reacting Ar — X with p-phenylboronic acid/boric acid ester at a ratio of 1. The same applies to the starting material E.
The technical solutions in the embodiments of the present application will be clearly and completely described below in conjunction with the luminescent auxiliary material of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments.
Example 1
Figure 602890DEST_PATH_IMAGE022
Dissolving a raw material A-1 (1.0 eq) in a toluene solution, dissolving a raw material E-1 (1.0 eq) in the toluene solution, slowly adding the solution of the raw material E-1 into the solution of the raw material A-1, and adding the solution of the raw material E-1 into the solution of the raw material A-1 in N 2 Adding Pd under atmosphere 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.05 eq) and t-BuONa (2.0 eq), heating to 80 ℃ and stirring for reaction for 6h, after the reaction is finished, carrying out suction filtration by using diatomite while hot, removing salt and a catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, then drying the combined organic layer by using magnesium sulfate, and removing the solvent by using a rotary evaporator. Finally, using mixture of dichloromethane and petroleum ether as eluent, purifying the residue by column chromatographyThe remainder was purified to give intermediate 5 (yield: 88.9%).
Intermediate 5 (1.0 eq) was dissolved in toluene solution, starting material F-1 (1.0 eq) was dissolved in toluene solution, and then the solution of starting material F-1 was slowly added to the solution of intermediate 5 in N 2 Adding Pd under atmosphere 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.05 eq) and t-BuONa (2.0 eq), heating to 85 ℃ and stirring for reaction for 6h, after the reaction is finished, carrying out suction filtration by using diatomite while hot, removing salt and a catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, then drying the combined organic layer by using magnesium sulfate, and removing the solvent by using a rotary evaporator. Finally, the remaining material was purified by column chromatography using a mixture of dichloromethane and petroleum ether as an eluent to obtain compound 1 (yield: 85.3%, mw: 663.82).
The detection analysis of the compound 1 obtained was as follows:
HPLC purity: is more than 99 percent.
Mass spectrometry (mass spectrometry is carried out by using an ultra-high liquid mass spectrometer and an ESI source, and the following steps are carried out): the theoretical value is 663.82; the test value was 664.13.
Elemental analysis:
the calculated values are: c, 90.47, H, 5.01, N, 2.11 and O, 2.41.
The test values are: 90.11 percent of C, 5.23 percent of H, 2.30 percent of N and 2.57 percent of O.
The corresponding NMR spectrum of compound 1 is shown in FIG. 1.
Example 2
Figure 785610DEST_PATH_IMAGE023
Dissolving the raw material A-53 (1.0 eq) in a toluene solution, dissolving the raw material E-53 (1.0 eq) in the toluene solution, slowly adding the solution of the raw material E-53 into the solution of the raw material A-53, and dissolving the raw material E-53 in the toluene solution in N 2 Adding Pd under atmosphere 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.05 eq) and t-BuONa (2.0)eq), heating to 80 ℃, stirring and reacting for 6h, after the reaction is finished, carrying out suction filtration by using diatomite while hot, removing salt and a catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, drying the combined organic layer by using magnesium sulfate, and removing the solvent by using a rotary evaporator. Finally, the remaining material was purified by column chromatography using a mixture of dichloromethane and petroleum ether as eluent to give intermediate 5 (yield: 87.6%).
Intermediate 5 (1.0 eq) was dissolved in toluene solution, starting material F-53 (1.0 eq) was dissolved in toluene solution, and then the solution of starting material F-53 was slowly added to the solution of intermediate 5 in N 2 Adding Pd under atmosphere 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.05 eq) and t-BuONa (2.0 eq), heating to 85 ℃ and stirring for reaction for 6h, after the reaction is finished, carrying out suction filtration by using diatomite while hot, removing salt and a catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, then drying the combined organic layer by using magnesium sulfate, and removing the solvent by using a rotary evaporator. Finally, the remaining material was purified by column chromatography using a mixture of dichloromethane and petroleum ether as an eluent to obtain compound 53 (yield: 85.0%, mw: 830.00).
The compound 53 obtained was subjected to detection analysis, and the results were as follows:
HPLC purity: is more than 99 percent.
Mass spectrum testing: theoretical value is 830.00; the test value was 830.25.
Elemental analysis:
the calculated values are: 89.72 percent of C, 4.74 percent of H, 1.69 percent of N, and 3.86 percent of O.
The test values are: 89.46 percent of C, 4.92 percent of H, 1.98 percent of N, and 4.02 percent of O.
The hydrogen spectrum of compound 53 by NMR is shown in FIG. 2.
Example 3
Figure 112817DEST_PATH_IMAGE024
Dissolving the raw material A-144 (1.0 eq) in a toluene solution, dissolving the raw material E-144 (1.0 eq) in the toluene solution, then slowly adding the solution of the raw material E-144 into the solution of the raw material A-144, and reacting in N 2 Adding Pd under atmosphere 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.05 eq) and t-BuONa (2.0 eq), heating to 85 ℃ and stirring for reaction for 6h, after the reaction is finished, carrying out suction filtration by using diatomite while hot, removing salt and a catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, then drying the combined organic layer by using magnesium sulfate, and removing the solvent by using a rotary evaporator. Finally, the remaining material was purified by column chromatography using a mixture of dichloromethane and petroleum ether as an eluent to give intermediate 5 (yield: 85.4%).
Intermediate 5 (1.0 eq) was dissolved in toluene solution, starting material F-144 (1.0 eq) was dissolved in toluene solution, and the solution of starting material F-144 was then added slowly to the solution of intermediate 5 in N 2 Adding Pd under atmosphere 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.05 eq) and t-BuONa (2.0 eq), heating to 85 ℃ and stirring for reaction for 6h, after the reaction is finished, carrying out suction filtration by using diatomite while hot, removing salt and a catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, then drying the combined organic layer by using magnesium sulfate, and removing the solvent by using a rotary evaporator. Finally, the remaining material was purified by column chromatography using a mixture of dichloromethane and petroleum ether as an eluent to obtain compound 144 (yield: 85.9%, mw: 896.12).
The compound 144 thus obtained was analyzed and found to have the following results:
HPLC purity: is more than 99 percent.
Mass spectrometry test: theoretical value is 896.12; the test value was 896.47.
Elemental analysis:
the calculated values are: 88.46 percent of C, 4.61 percent of H, 1.56 percent of N, 1.79 percent of O, and 3.58 percent of S.
The test values are: 88.11 percent of C, 4.80 percent of H, 1.73 percent of N, 1.96 percent of O, and 3.70 percent of S.
Example 4
Figure 39185DEST_PATH_IMAGE025
Dissolving the raw material A-156 (1.0 eq) in a toluene solution, dissolving the raw material C-156 (1.0 eq) in the toluene solution, and slowly adding the solution of the raw material C-156 into the solution of the raw material A-156 in N 2 Adding Pd under atmosphere 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.05 eq) and t-BuONa (2.0 eq), heating to 80 ℃ and stirring for reaction for 4h, after the reaction is finished, carrying out suction filtration by using diatomite while hot, removing salt and a catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, then drying the combined organic layer by using magnesium sulfate, and removing the solvent by using a rotary evaporator. Finally, the remaining material was purified by column chromatography using a mixture of dichloromethane and petroleum ether as eluent to give intermediate 3 (yield: 91.4%).
Dissolving the intermediate 3 (1.0 eq) in a mixed solution of toluene, ethanol and water (the volume ratio of toluene, ethanol and water is 3; after the organic phases were combined, dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. And (3) completely dissolving the solid organic matter by using dichloromethane, slowly and dropwisely adding the dissolved solid organic matter into a petroleum ether solution, uniformly stirring, precipitating, carrying out suction filtration to obtain a solid, sequentially leaching by using absolute ethyl alcohol and petroleum ether, and drying to prepare an intermediate 4 (yield: 57.3%).
Intermediate 4 (1.0 eq) was dissolved in toluene solution, starting material E-156 (1.0 eq) was dissolved in toluene solution, and then the solution of starting material E-156 was slowly added to the solution of intermediate 4 in N 2 Adding Pd under atmosphere 2 (dba) 3 (0.01 eq), X-phos (0.05 eq) and t-BuONa (2.0 eq), heating to 90 ℃ and stirring for reaction for 6h, after the reaction is finished, carrying out suction filtration with diatomite while hot, removing salts and catalyst, cooling the filtrate to room temperature, adding distilled water to the filtrate for washing, separating the liquid and retaining the organic phase, extracting the aqueous phase with ethyl acetate, then drying the combined organic layers with magnesium sulfate, and removing the solvent with a rotary evaporator. Finally, the remaining material was purified by column chromatography using a mixture of dichloromethane and petroleum ether as an eluent to give intermediate 5 (yield: 77.4%).
Intermediate 5 (1.0 eq) was dissolved in toluene solution, starting material F-156 (1.0 eq) was dissolved in toluene solution, and then the solution of starting material F-156 was slowly added to the solution of intermediate 5 in N 2 Adding Pd under atmosphere 2 (dba) 3 （0.01eq）、P(t-Bu) 3 (0.05 eq) and t-BuONa (2.0 eq), heating to 85 ℃ and stirring for reaction for 6h, after the reaction is finished, carrying out suction filtration by using diatomite while hot, removing salt and a catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, then drying the combined organic layer by using magnesium sulfate, and removing the solvent by using a rotary evaporator. Finally, the remaining material was purified by column chromatography using a mixture of dichloromethane and petroleum ether as an eluent to obtain compound 156 (yield: 80.2%, mw: 892.11).
The compound 156 thus obtained was subjected to detection analysis, and the results were as follows:
HPLC purity: is more than 99 percent.
Mass spectrometry test: theoretical value is 892.11; the test value was 892.58.
Elemental analysis:
the calculated values are: 91.55 percent of C, 5.08 percent of H, 1.57 percent of N, and 1.79 percent of O.
The test values are: 91.21 percent of C, 5.34 percent of H, 1.81 percent of N and 1.93 percent of O.
The general formula is chemical formula I in the summary of the invention, and the synthetic routes and principles of other compounds are the same as those of the above-listed examples, so the description is not exhaustive. The luminescent auxiliary materials shown in the following table 1 can be obtained according to the preparation methods in examples 5 to 51 of the present application:
Figure 322399DEST_PATH_IMAGE026
Figure 941599DEST_PATH_IMAGE027
Figure 739790DEST_PATH_IMAGE028
Figure 217652DEST_PATH_IMAGE029
Figure 152110DEST_PATH_IMAGE030
Figure 738949DEST_PATH_IMAGE031
Figure 775169DEST_PATH_IMAGE032
Figure 43339DEST_PATH_IMAGE033
Figure 97883DEST_PATH_IMAGE034
Figure 58886DEST_PATH_IMAGE035
Figure 316823DEST_PATH_IMAGE036
Figure 388684DEST_PATH_IMAGE037
according to another aspect of the present invention, there is provided an organic electric element including a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, in which case the organic layer includes at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer, and at least one of the above-mentioned compounds is contained in such an organic layer. That is, the organic layer may be formed of one single compound or a mixture of two or more compounds represented by the above chemical formula I-1 and chemical formula I-2. Preferably, a single compound or a mixture comprising two or more compounds represented by the above chemical formula I-1 and chemical formula I-2 may be included in the luminescence auxiliary layer.
The present application is not limited to the method for manufacturing the organic electroluminescent device, and the organic electroluminescent device may be manufactured by a conventional method in the art, but preferably, the present application forms an anode by depositing metal, conductive oxide, or an alloy thereof on a substrate by using a method such as thin film evaporation, electron beam evaporation, or physical vapor deposition, and then forms an organic layer and a cathode thereon.
The organic electroluminescent device provided by the present application may be applied to an Organic Light Emitting Device (OLED), an Organic Solar Cell (OSC), an electronic paper (e-paper), an Organic Photoreceptor (OPC), or an Organic Thin Film Transistor (OTFT).
When the organic layer includes the light-emitting auxiliary layer, the light-emitting auxiliary layer includes the light-emitting auxiliary material provided in the above embodiment.
Device example 1
The preparation method of the organic electroluminescent device containing the luminescent auxiliary material specifically comprises the following steps:
a. an ITO anode: cleaning an ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, ultrasonically cleaning for 30min, repeatedly cleaning for 2 times by using distilled water, ultrasonically cleaning for 10min, transferring to a spin dryer for spin-drying after the cleaning is finished, finally baking for 2 hours at 220 ℃ by using a vacuum oven, and cooling after the baking is finished. Using the substrate as an anode, performing a device evaporation process by using an evaporation machine, and sequentially evaporating other functional layers on the substrate;
b. HIL (hole injection layer): vacuum evaporating the hole injection layer materials HT-1 and P-dots at the evaporation rate of 1 \ 8491/s, wherein the chemical formulas are shown as follows; wherein the evaporation rate ratio of HT-1 to P-dot is 97:3, the thickness is 10nm;
c. HTL (hole transport layer): performing vacuum evaporation on the HT-1 with the thickness of 120nm on the hole injection layer at the evaporation rate of 1.5 v 8491/s to form a hole transport layer;
d. a light-emitting auxiliary layer: vacuum evaporating 10nm of the compound 1 provided in example 1 on the hole transport layer at an evaporation rate of 0.5 v 8491/s as a light-emitting auxiliary layer;
e. EML (light-emitting layer): then, a main body material (Host) and a doping material (span) with the thickness of 20nm are vacuum-evaporated on the luminescence auxiliary layer at the evaporation rate of 1 \8491/s to be used as a luminescent layer, wherein the chemical formulas of the Host and the span are shown as follows; wherein, the evaporation rate ratio of Host to Dopant is 98:2;
f. HB (hole blocking layer): vacuum evaporating HB-1 with the thickness of 5.0nm at the evaporation rate of 0.5 v 8491/s;
g. ETL (electron transport layer): ET and Liq with the thickness of 35nm are subjected to vacuum evaporation at the evaporation rate of 1 \ 8491/s to serve as electron transport layers, and the chemical formula of the ET is shown as follows; wherein the evaporation rate ratio of ET to Liq is 50:50;
h. EIL (electron injection layer): evaporating Yb film layer at 1.0nm at the evaporation rate of 0.5 \8491/s to form an electron injection layer;
i. cathode: performing evaporation plating on magnesium and silver at 18nm according to an evaporation plating rate ratio of 1/8491s, wherein the evaporation plating rate ratio is 1;
j. light extraction layer: CPL with the thickness of 70nm is evaporated on the cathode in vacuum at the evaporation rate of 1/8491s to be used as a light extraction layer;
k. packaging the substrate subjected to evaporation: firstly, coating the cleaned back cover plate by using UV glue by using gluing equipment, then moving the coated cover plate to a pressing working section, placing the evaporated base plate on the upper end of the cover plate, finally, attaching the base plate and the cover plate under the action of attaching equipment, and simultaneously, finishing the illumination and curing of the UV glue.
The structural formula referred to above is as follows:
Figure 766576DEST_PATH_IMAGE038
with reference to the method provided in device example 1 above, compounds 2, 5, 6, 8, 9, 10, 17, 18, 29, 30, 32, 33, 37, 41, 42, 45, 49, 53, 57, 59, 61, 64, 65, 66, 70, 72, 73, 77, 80, 97, 101, 117, 120, 130, 131, 136, 138, 139, 144, 152, 155, 156, 160, 165, 169, 170, 178, 181, 186, 188 were selected respectively instead of compound 1, and evaporation of the light-emitting auxiliary layer was performed, and corresponding organic electroluminescent devices were prepared, and denoted as device examples 2 to 51, respectively.
Devices comparative examples 1-11:
this comparative example provides an organic electroluminescent device, which was fabricated by a method different from that of device example 1 only in that the organic electroluminescent device was fabricated by vapor deposition using the existing comparative compounds a, b, c, d, e, f, g, h, i, j, k, respectively, instead of the light-emitting auxiliary material (compound 1) in device example 1 above, to fabricate comparative devices 1 to 11. Wherein the chemical structural formulas of the comparative compounds a, b, c, d, e, f, g, h, i, j and k are as follows:
Figure 429639DEST_PATH_IMAGE039
Figure 892981DEST_PATH_IMAGE040
the organic electroluminescent devices obtained in the above-described device examples 1 to 51 and device comparative examples 1 to 11 were characterized for driving voltage, luminous efficiency, BI value and lifetime at a luminance of 1000 (nits). The test results are shown in table 2.
Figure 253686DEST_PATH_IMAGE041
Figure 282822DEST_PATH_IMAGE042
Figure 320048DEST_PATH_IMAGE043
Note: in a blue top-emitting device, current efficiency is greatly affected by chromaticity, so that the influence of chromaticity on efficiency is taken into consideration, and the ratio of luminous efficiency to CIEy is defined as a BI value, i.e., BI = (cd/a)/CIEy.
As can be seen from table 2, device examples 1 to 51 prepared using the light-emitting auxiliary material provided in the present application were improved in BI value and lifetime while reducing driving voltage, compared to the existing organic electroluminescent devices provided in device comparative examples 1 to 11.
Compared with a comparative compound, even if the compound has the same benzofuran parent nucleus, the spatial structure of the compound can be changed by changing the position of a fused benzene ring on dibenzofuran, so that the hole mobility of the compound is improved; on the other hand, the luminescent efficiency of the device is improved by connecting a substituent at a specific position of the dibenzofuran and appropriately extending the triarylamine group connected with the dibenzofuran to increase the conjugated surface of the compound.
In the present specification, the embodiments are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present application. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the application. Thus, the present application is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (10)

1. A luminescent auxiliary material is characterized in that the structural formula of the luminescent auxiliary material is shown as chemical formula I:
Figure 149456DEST_PATH_IMAGE001
wherein L is selected from a single bond, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3-to 30-membered heteroaryl group, the heteroatoms of which are selected from oxygen, nitrogen, sulfur;
Ar 1 selected from the following groups or combinations thereof:
Figure 310922DEST_PATH_IMAGE002
；
n independently represents an integer of 1 to 4;
Ar 2 independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted (C10-C30) fused ring, substituted or unsubstituted 3-30 membered heteroaryl, wherein the heteroatoms are selected from oxygen, nitrogen, sulfur,or; wherein Ar is 2 When the N-substituted phenyl ring is connected with the benzene ring, the N-substituted phenyl ring is not connected with the ortho-position of the connection of the N-substituted phenyl ring and the benzene ring;
ring A is a substituent fused on a benzene ring, can be fused with 1, 2-position and 2, 3-position of the benzene ring, and is selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted 3-to 30-membered heteroaryl, and heteroatoms of the heteroaryl are selected from oxygen, nitrogen and sulfur;
the substituents include: hydrogen, deuterium, halogen, cyano, C1-C6 alkyl, C6-C12 aryl, C6-C12 heteroaryl, wherein the heteroatoms are selected from oxygen, nitrogen, sulfur; wherein said C1-C6 alkyl represents methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl; the aryl of C6-C12 represents phenyl, biphenyl and naphthyl; the heteroaryl of C6-C12 represents dibenzothiophene and dibenzofuran.
2. The luminescent assist material according to claim 1, wherein the ring a is a phenyl group.
3. A luminescent support material as claimed in claim 1, wherein L is selected from a single bond, the following groups or combinations thereof:
Figure 194565DEST_PATH_IMAGE003
。
4. the luminescent auxiliary material according to claim 1, wherein Ar is 2 Selected from hydrogen, and the following groups or combinations thereof:
Figure 668271DEST_PATH_IMAGE004
；
wherein in the formula, a is represented as a connecting point.
5. The luminescent auxiliary material according to claim 1, wherein the structural formula of the luminescent auxiliary material is represented by formulas I-1 to I-2:
Figure 637364DEST_PATH_IMAGE005
。
6. a luminescent auxiliary material as claimed in claim 1, wherein the luminescent auxiliary material is any one of the following structures:
Figure 339872DEST_PATH_IMAGE006
Figure 609179DEST_PATH_IMAGE007
Figure 722629DEST_PATH_IMAGE008
Figure 460909DEST_PATH_IMAGE009
Figure 216375DEST_PATH_IMAGE010
Figure 74610DEST_PATH_IMAGE011
Figure 890119DEST_PATH_IMAGE012
Figure 584537DEST_PATH_IMAGE013
Figure 878115DEST_PATH_IMAGE014
Figure 590856DEST_PATH_IMAGE015
Figure 842846DEST_PATH_IMAGE016
Figure 756051DEST_PATH_IMAGE017
。
7. a method of preparing a luminescent support material, comprising:
Figure 853320DEST_PATH_IMAGE018
；
dissolving a raw material A in anhydrous tetrahydrofuran, adding n-BuLi under the protection of nitrogen for reaction, continuing adding an iodine-containing tetrahydrofuran solution for reaction, and adding a sodium thiosulfate aqueous solution for liquid separation after the reaction is finished to obtain an intermediate 1;
dissolving the intermediate 1 and the raw material B in a mixed solution of toluene, ethanol and water, adding a palladium catalyst and salt under the protection of nitrogen, uniformly stirring, heating to 80-100 ℃, and refluxing for 5-7 hours to obtain an intermediate 2;
dissolving the intermediate 2 and the raw material C in a toluene solution, adding a palladium catalyst, a phosphorus ligand and a salt in a nitrogen atmosphere, heating to 90-115 ℃, and stirring for reacting for 4-12h to obtain an intermediate 3;
dissolving the intermediate 3 and the raw material D in a mixed solution of toluene, ethanol and water, adding a palladium catalyst and salt under the protection of nitrogen, and uniformly stirring to obtain an intermediate 4;
dissolving the intermediate 4 and the raw material E in a toluene solution, adding a palladium catalyst, a phosphorus ligand and a salt in a nitrogen atmosphere, heating to 90 ℃, and stirring for reacting for 4-12 hours to obtain an intermediate 5;
and dissolving the intermediate 5 and the raw material F in a toluene solution, adding a palladium catalyst, a phosphorus ligand and a salt in a nitrogen atmosphere, heating to 90-120 ℃, and stirring for reacting for 4-12h to obtain the luminescent auxiliary material shown in the chemical formula I.
8. A light-emitting device characterized in that it comprises a luminescent support material according to any one of claims 1 to 6.
9. The light-emitting device according to claim 8, wherein the light-emitting device comprises a light-emission auxiliary layer; the luminescent auxiliary layer comprises the luminescent auxiliary material according to any one of claims 1 to 6.
10. A light-emitting apparatus characterized by comprising the light-emitting device according to claim 8 or 9.
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