A light-emitting auxiliary material, a preparation method and application thereof, and an organic electroluminescent device comprising the same

Abstract

The application belongs to the field of organic photoelectric materials, and discloses a luminescent auxiliary material, a preparation method and application thereof, and an organic electroluminescent device containing the luminescent auxiliary material. A general structure of the luminescent auxiliary material is provided. The application provides a luminescent auxiliary material, and aims to solve the problems of reduced efficiency, poor stability, short service life and the like of existing luminescent devices, and is suitable for promotion and application.

Description

Technical Field

[0001] This invention belongs to the field of organic optoelectronic materials, specifically relating to a light-emitting auxiliary material, its preparation method and application, and an organic electroluminescent device containing the same. Background Technology

[0002] Organic light emission typically refers to the phenomenon of converting electrical energy into light energy using organic materials. Because organic light-emitting devices (OLEDs) utilize this phenomenon, they exhibit wide viewing angles, excellent contrast ratios, fast response times, and superior brightness, driving voltage, and response speed characteristics, leading to extensive research in this field.

[0003] Currently, many improvements have been made to enable the practical application of organic EL devices. For example, by further distributing the various functions of the laminated structure and forming the anode, high efficiency and high durability can be achieved by setting hole injection layer, hole transport layer, hole blocking layer, light-emitting layer, electron transport layer, electron injection layer and cathode on the substrate.

[0004] In this organic EL device, charges injected from both electrodes recombine in the emissive layer to produce light emission. In this case, efficiently transferring the charge of holes and electrons to the emissive layer is crucial, and the device requires excellent carrier balance. Furthermore, the luminescence efficiency is improved by enhancing the hole injection and electron blocking properties that impede electron injection from the cathode to increase the recombination probability, and by confining the excitons generated within the emissive layer. This demonstrates the critical role of the light-emitting auxiliary material.

[0005] Research on organic electroluminescent materials has been extensively carried out in academia and industry, but so far, stable and efficient organic layer materials for organic electrical components have not been fully developed, and the industrialization process of this technology still faces many key issues.

[0006] Therefore, developing a light-emitting auxiliary material to enable organic electroluminescent devices to have the advantages of low driving voltage, high luminous efficiency, and long lifespan is a technical problem that urgently needs to be solved by those skilled in the art. Summary of the Invention

[0007] In view of this, the present invention provides a light-emitting auxiliary material, which aims to solve the problems of reduced efficiency, poor stability and short lifespan of existing light-emitting devices.

[0008] To achieve the above objectives, the first objective of this invention is to provide a light-emitting auxiliary material. The following technical solution is adopted: A luminescent auxiliary material having the following general structural formula: ; Chemical Formula I in, X is independently selected from O, S, or NR8; R1 independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1~C10) alkyl, substituted or unsubstituted (C3~C8) cycloalkyl, substituted or unsubstituted (3-membered~10-membered) heterocycloalkyl; wherein the heteroatom is selected from N, O, S, Si, P or Se; R2 and R3 independently represent one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1~C10) alkyl, substituted or unsubstituted (C3~C10) cycloalkyl, substituted or unsubstituted (3-membered~10-membered) heterocycloalkyl, substituted or unsubstituted (C6~C30) aryl, substituted or unsubstituted (3-membered~30-membered) heteroaryl, wherein the heteroatom is N, O, S, Si, P or Se, and R2 and R3 cannot be linked together to form a ring; R4 and R5 independently represent one of the following: hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, sulfonic acid, phosphoric acid, boron alkyl, substituted or unsubstituted (C1~C25) alkyl, substituted or unsubstituted (C3~C20) cycloalkyl, substituted or unsubstituted (3-membered~20-membered) heterocycloalkyl, substituted or unsubstituted (C6~C30) aryl, substituted or unsubstituted (3-membered~30-membered) heteroaryl, wherein the heteroatom is N, O, S, Si, P or Se; R8 independently represents one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1~C20) alkyl, substituted or unsubstituted (C3~C20) cycloalkyl, substituted or unsubstituted (3-membered~20-membered) heterocycloalkyl, substituted or unsubstituted (C6~C30) aryl, substituted or unsubstituted (3-membered~30-membered) heteroaryl, wherein the heteroatom is N, O, S, Si, P or Se; Ar represents substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted 3- to 20-membered heteroaryl groups, wherein the heteroatom is selected from O, N, or S; Ar1 is independently represented as an aryl group with a total number of carbon atoms (C6~C18) and a heteroaryl group with a total number of atoms (3-membered~18-membered), wherein the heteroatoms are N, O, S, Si, P or Se; Ar2 can be independently represented as a substituted or unsubstituted (C6~C20) aryl or a substituted or unsubstituted (3-membered~20-membered) heteroaryl, wherein the heteroatom is N, O, S, Si, P or Se.

[0009] It is worth noting that cyclic Ar is a substituent fused to the benzene ring, and cyclic Ar can be fused to any position on the benzene ring.

[0010] Furthermore, the general structural formula of chemical formula I is: .

[0011] Among them, R1 to R5, Ar1, and Ar2 in the above chemical formulas -I-1 to -I-9 are as defined above.

[0012] Further optimization, R2 and R3 represent hydrogen; Further optimization, Ar1 indicates: .

[0013] The preferred structural formula of the above chemical formula I is: .

[0014] In the above technical solutions, the term "substituted or unsubstituted" means substituted by one, two or more substituents selected from the following: hydrogen; deuterium; halogen group; nitrile group; C1-C5 alkyl; C6-C20 aryl; C6-C18 heteroaryl; or substituted by substituents connected to two or more of the substituents shown above, or without substituents. For example, "substituents connected to two or more substituents" can include biphenyl. In other words, biphenyl can be aryl, or can be interpreted as substituents connected to two phenyl groups.

[0015] Furthermore, the luminescent auxiliary material is any one of the following structures, but is not limited thereto: .

[0016] A second objective of this invention is to provide a method for preparing the luminescent auxiliary material as described above, comprising the following reaction steps: (1) Preparation of intermediate 1 Raw material A (1.0 eq) and raw material B (1.0 eq) were dissolved in toluene solution. Then, the raw material B solution was slowly added dropwise to the raw material A solution. After three purgings, under nitrogen protection, tris(dibenzylacetone)dipalladium (0.01 eq), tri-tert-butylphosphine (0.05 eq), and sodium tert-butoxide (2.0 eq) were added, stirred until homogeneous, and heated to reflux for 5 hours. After the reaction was complete, the temperature was slightly lowered, and the mixture was filtered through diatomaceous earth to remove salts and catalyst. The filtrate was cooled to room temperature, washed three times with water, and the organic phase was retained. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The solid organic matter was completely dissolved using a small amount of dichloromethane, and then slowly added dropwise to a petroleum ether solution. After stirring until homogeneous, a precipitate formed. The precipitate was filtered to obtain a solid, which was then washed successively with 300 mL of anhydrous ethanol and 200 mL of petroleum ether, and dried to obtain intermediate 1. (2) Preparation of intermediate 2 Intermediate 1 (1.0 eq) was dissolved in toluene solution, and raw material C (1.0 eq) was dissolved in toluene solution. Then, the raw material C solution was slowly added dropwise to the intermediate 1 solution. After purging three times, tris(dibenzylacetone)dipalladium (0.01 eq), tri-tert-butylphosphine (0.05 eq), and sodium tert-butoxide (2.0 eq) were added under nitrogen protection. The mixture was stirred until homogeneous, heated to reflux, and reacted for 5 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The solid organic matter was completely dissolved with a small amount of dichloromethane and then slowly added dropwise to petroleum ether solution. After stirring until homogeneous, a precipitate formed. The precipitate was filtered to obtain a solid, which was washed successively with 300 mL of anhydrous ethanol and 200 mL of petroleum ether, and then dried to obtain intermediate 2. (3) Preparation of chemical formula I Intermediate 2 (1.0 eq) was dissolved in a mixed solution of toluene, ethanol, and water, and starting material D (1.0 eq) was dissolved in the same mixed solution. The solution of starting material D was then slowly added dropwise to the solution of intermediate 2. After three purgings, cesium carbonate (2.0 eq), phosphine ligand (0.05 eq), and palladium catalyst (0.05 eq) were added under nitrogen protection. The mixture was stirred thoroughly, heated to 90°C, and refluxed for 6 hours. After the reaction was complete, the temperature was slightly lowered, and the mixture was filtered through diatomaceous earth to remove salts and catalyst. The filtrate was cooled to room temperature, washed three times with water, and the organic phase was retained. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (Vdichloromethane:Vpetroleum ether = 10:4) to obtain chemical formula I. The specific synthesis route is shown below: ; X, Ar, Ar1, Ar2, and R1~R5 are as defined in the above chemical formula I.

[0017] A third objective of this invention is to provide the application of the light-emitting auxiliary material described above in the fabrication of organic light-emitting devices, organic solar cells, electronic paper, organic photoreceptors, or organic thin-film transistors.

[0018] A fourth object of the present invention is to provide an organic electroluminescent device, comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode; and The organic layer includes at least one of the following: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a capping layer; and, The organic layer includes at least one of the following: a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron injection and transport layer; and, As an anode material, a material with a high work function is generally preferred to facilitate hole injection into the organic material layer. Specific anode materials that can be used in this invention include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0019] Hole-injecting materials are materials that advantageously receive holes from the anode at low voltages, and the highest occupied molecular orbital (HOMO) of the hole-injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole-injecting materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, and conductive polymers based on polyaniline and polythiophene, and also include compounds capable of p-doping.

[0020] Hole transport materials are materials capable of receiving holes from the anode or hole injection layer and transporting them to the light-emitting layer, and possessing high hole mobility. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers possessing both conjugated and non-conjugated portions.

[0021] The luminescent layer can emit red, green, or blue light and can be formed from phosphorescent or fluorescent materials. The luminescent material is a material capable of emitting light in the visible light region by receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and by combining the holes with the electrons. It is preferably a material with favorable quantum efficiency for fluorescence or phosphorescence. Specific examples include: 8-hydroxyquinoline aluminum ligand (Alq3); carbazole-based compounds; dipolystyrene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds based on benzocarbazole, benzothiazole, and benzimidazole; polymers based on poly(p-phenylenevinylene) (PPV); spirocyclic compounds; polyfluorene; fluorene, etc., but not limited to these.

[0022] The main materials of the luminescent layer include fused aromatic ring derivatives and heterocyclic compounds. Specifically, fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited to these.

[0023] The electron transport layer facilitates electron transport. Electron transport materials are those that advantageously receive electrons from the cathode and transport them to the emitting layer; materials with high electron mobility are suitable. Specific examples include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavonoid-metal complexes, etc., but are not limited to these. The thickness of the electron transport layer can range from 1 nm to 50 nm. Electron transport layers with a thickness of 1 nm or greater have the advantage of preventing a decrease in electron transport properties, while thicknesses of 50 nm or less have the advantage of preventing an increase in the driving voltage required to enhance electron migration due to an excessively thick electron transport layer.

[0024] The electron injection layer can promote electron injection. Preferred electron injection materials are compounds that possess electron transport capabilities, exhibit an electron injection effect from the cathode, demonstrate excellent electron injection effects on the luminescent layer or luminescent material, prevent excitons generated in the luminescent layer from migrating to the hole injection layer, and, in addition, possess excellent thin film forming capabilities. Specific examples include, but are not limited to, fluorenones, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azoles, diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal complexes, and nitrogen-containing 5-membered ring derivatives.

[0025] As cathode materials, materials with low work functions are generally preferred to facilitate electron injection into the organic material layer. Specific examples of cathode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials, such as LiF / Al or LiO2 / Al; and so on, but are not limited to these.

[0026] The present invention does not limit the preparation method of the organic electroluminescent device. Preferredly, metals and conductive oxides and their alloys are deposited on a substrate by thin film evaporation, electron beam evaporation or physical vapor deposition to form an anode, and then an organic layer and a cathode are deposited thereon to obtain the organic electroluminescent device.

[0027] Compared with the prior art, the present invention provides a light-emitting auxiliary material, its preparation method and application, and an organic electroluminescent device containing the same, which has the following superior effects: 1) In the triarylamine molecule, which serves as the HT functional group, a dibenzofuran / thiophene or benzocarbazole group with aromatic or heteroaryl substituents is introduced on the basis of the benzo[a]fluorene group. The electronegativity of the polar atoms O, S, and N is used to adjust the HOMO / LUMO energy levels of the molecule, while the conjugated system is expanded through the on-side substituents. Ultimately, the energy levels of the material of this invention are more matched with the red light host and red light HT material compared to other materials without on-side substituents, fluorene groups, benzo[a]fluorene groups, etc., thereby improving luminescence efficiency. 2) For the third aryl group in triarylamines, the introduction of the first aryl benzo[a]fluorene group and the dibenzofuran / thiophene or benzo[a]carbazole group that is substituted on the second aryl side results in a larger molecular weight of the compound and limits it to a reasonable number of atoms, thereby balancing the overall molecular weight of the molecule and controlling the evaporation temperature so that it is not too high and affects the life of the device. Attached Figure Description

[0028] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are only embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on the provided drawings without creative effort.

[0029] Appendix Figure 1 This is the 1H NMR spectrum of compound-4. Detailed Implementation

[0030] The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative effort are within the scope of protection of the present invention.

[0031] The various embodiments in this specification are described in a progressive manner, with each embodiment focusing on its differences from other embodiments. Similar or identical parts between embodiments can be referred to interchangeably. For the apparatus disclosed in the embodiments, since they correspond to the methods disclosed in the embodiments, the description is relatively simple; relevant parts can be referred to the method section.

[0032] Example 1 ; Raw material A-4 (30.00 mmol) was dissolved in toluene solution, and raw material B-4 (30.00 mmol) was dissolved in toluene solution. Then, the raw material B-4 solution was slowly added dropwise to the raw material A-4 solution. After three purgings, under nitrogen protection, tris(dibenzylacetone)palladium (0.30 mmol), tri-tert-butylphosphine (1.50 mmol), and sodium tert-butoxide (60.00 mmol) were added, stirred thoroughly, heated to 90 °C, and refluxed for 5 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was purified using diatomaceous earth. The solution was filtered to remove salt and catalyst. After cooling the filtrate to room temperature, it was washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The solid organic matter was completely dissolved in a small amount of dichloromethane and then slowly added dropwise to a petroleum ether solution. After stirring until homogeneous, a precipitate formed. The precipitate was filtered to obtain a solid, which was then washed successively with 300 mL of anhydrous ethanol and 200 mL of petroleum ether, and dried to obtain intermediate 1 (7.47 g, yield: 74.28%). Intermediate 1 (20.87 mmol) was dissolved in toluene solution, and raw material C-4 (20.87 mmol) was dissolved in toluene solution. Then, the raw material C-4 solution was slowly added dropwise to the intermediate 1 solution. Next, after three venting cycles, tris(dibenzylacetone)dipalladium (0.21 mmol), tri-tert-butylphosphine (1.04 mmol), and sodium tert-butoxide (41.74 mmol) were added under nitrogen protection. The mixture was stirred until homogeneous, heated to 90 °C, and refluxed for 5 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered through diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The solid organic matter was completely dissolved in a small amount of dichloromethane and then slowly added dropwise to a petroleum ether solution. After stirring until homogeneous, a precipitate formed. The precipitate was filtered to obtain a solid, which was washed successively with 300 mL of anhydrous ethanol and 200 mL of petroleum ether, and then dried to obtain intermediate 2 (7.08 g, yield: 61.44%). Intermediate 2 (12.68 mmol) was dissolved in a mixed solution of toluene, ethanol, and water, and starting material D-4 (12.68 mmol) was dissolved in the same solution. The D-4 solution was then slowly added dropwise to the intermediate 2 solution. After three purgings, cesium carbonate (25.36 mmol), tri-tert-butylphosphine (0.63 mmol), and tris(dibenzylacetone)palladium (0.63 mmol) were added under nitrogen protection. The mixture was stirred thoroughly, heated to 90 °C, and refluxed for 6 h. After the reaction was complete, the temperature was slightly lowered, and the mixture was filtered through diatomaceous earth to remove salts and catalyst. The filtrate was cooled to room temperature, washed three times with water, and the organic phase was retained. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (Vdichloromethane:Vpetroleum ether = 10:4) to obtain compound-4. (3.98g, yield, 52.88%, Mw: 593.79) The obtained compound-4 was analyzed, and the results are as follows: HPLC purity: >99%.

[0033] Mass spectrometry test: theoretical value 593.79; test value 593.54.

[0034] Elemental analysis: The calculated values ​​are: C, 86.98; H, 5.26; N, 2.36; S, 5.40.

[0035] The test values ​​are: C, 86.66; H, 5.41; N, 2.50; S, 5.63.

[0036] Nuclear magnetic resonance hydrogen spectrum: as shown Figure 1 As shown.

[0037] Example 2 ; Dissolve raw material A-261 (30.00 mmol) in toluene solution and raw material B-261 (30.00 mmol) in toluene solution. Then slowly add the raw material B-261 solution dropwise to the raw material A-261 solution. Next, after three venting cycles, tris(dibenzylacetone)dipalladium (0.30 mmol), tri-tert-butylphosphine (1.50 mmol), and sodium tert-butoxide (60.00 mmol) were added under nitrogen protection. The mixture was stirred until homogeneous, heated to 90 °C, and refluxed for 5 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered through diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The solid organic matter was completely dissolved in a small amount of dichloromethane and then slowly added dropwise to a petroleum ether solution. After stirring until homogeneous, a precipitate formed. The precipitate was filtered to obtain a solid, which was washed successively with 300 mL of anhydrous ethanol and 200 mL of petroleum ether, and then dried to obtain intermediate 1 (9.01 g, yield: 70.59%). Intermediate 1 (18.80 mmol) was dissolved in toluene solution, and raw material C-261 (18.80 mmol) was dissolved in toluene solution. Then, the raw material C-261 solution was slowly added dropwise to the intermediate 1 solution. Next, after three venting cycles, tris(dibenzylacetone)dipalladium (0.19 mmol), tri-tert-butylphosphine (0.94 mmol), and sodium tert-butoxide (37.60 mmol) were added under nitrogen protection. The mixture was stirred until homogeneous, heated to 90 °C, and refluxed for 5 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered through diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The solid organic matter was completely dissolved in a small amount of dichloromethane and then slowly added dropwise to a petroleum ether solution. After stirring until homogeneous, a precipitate formed. The precipitate was filtered to obtain a solid, which was washed successively with 300 mL of anhydrous ethanol and 200 mL of petroleum ether, and then dried to obtain intermediate 2 (7.37 g, yield: 61.10%). Intermediate 2 (10.90 mmol) was dissolved in a mixed solution of toluene, ethanol and water, and raw material D-261 (10.90 mmol) was dissolved in a mixed solution of toluene, ethanol and water. Then the raw material D-261 solution was slowly added dropwise to the intermediate 2 solution. After three purgings, cesium carbonate (21.80 mmol), tri-tert-butylphosphine (0.55 mmol), and tris(dibenzylacetone)palladium (0.55 mmol) were added under nitrogen protection. The mixture was stirred until homogeneous, heated to 90 °C, and refluxed for 6 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The organic phases were combined and dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (Vdichloromethane:Vpetroleum ether = 10:4) to obtain compound-261 (4.11 g, yield, 51.09%, Mw: 739.98).

[0038] The obtained compound -261 was analyzed, and the results are as follows: HPLC purity: >99%.

[0039] Mass spectrometry test: theoretical value 739.98; test value 739.81.

[0040] Elemental analysis: The calculated values ​​are: C, 86.03; H, 5.59; N, 1.89; O, 2.16; S, 4.33.

[0041] The test values ​​were: C, 85.71; H, 5.70; N, 2.09; O, 2.40; S, 4.57.

[0042] Example 3 ; Raw material A-607 (30.00 mmol) was dissolved in toluene solution, and raw material B-607 (30.00 mmol) was dissolved in toluene solution. Then, the raw material B-607 solution was slowly added dropwise to the raw material A-607 solution. Next, after three venting cycles, tris(dibenzylacetone)dipalladium (0.30 mmol), tri-tert-butylphosphine (1.50 mmol), and sodium tert-butoxide (60.00 mmol) were added under nitrogen protection. The mixture was stirred until homogeneous, heated to 90 °C, and refluxed for 5 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered through diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The solid organic matter was completely dissolved in a small amount of dichloromethane and then slowly added dropwise to a petroleum ether solution. After stirring until homogeneous, a precipitate formed. The precipitate was filtered to obtain a solid, which was washed successively with 300 mL of anhydrous ethanol and 200 mL of petroleum ether, and then dried to obtain intermediate 1 (9.72 g, yield: 70.21%). Intermediate 1 (19.50 mmol) was dissolved in toluene solution, and raw material C-607 (19.50 mmol) was dissolved in toluene solution. Then, the raw material C-607 solution was slowly added dropwise to the intermediate 1 solution. Next, after three venting cycles, tris(dibenzylacetone)dipalladium (0.20 mmol), tri-tert-butylphosphine (1.00 mmol), and sodium tert-butoxide (39.00 mmol) were added under nitrogen protection. The mixture was stirred until homogeneous, heated to 90 °C, and refluxed for 5 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered through diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The solid organic matter was completely dissolved in a small amount of dichloromethane and then slowly added dropwise to a petroleum ether solution. After stirring until homogeneous, a precipitate formed. The precipitate was filtered to obtain a solid, which was washed successively with 300 mL of anhydrous ethanol and 200 mL of petroleum ether, and then dried to obtain intermediate 2 (7.75 g, yield: 60.03%). Intermediate 2 (10.57 mmol) was dissolved in a mixed solution of toluene, ethanol, and water, and starting material D-607 (10.57 mmol) was dissolved in the same mixed solution. The D-607 solution was then slowly added dropwise to the intermediate 2 solution. After three purgings, cesium carbonate (21.14 mmol), tri-tert-butylphosphine (0.53 mmol), and tris(dibenzylacetone)palladium (0.53 mmol) were added under nitrogen protection. The mixture was stirred thoroughly, heated to 90 °C, and refluxed for 6 h. After the reaction was complete, the temperature was slightly lowered, and the mixture was filtered through diatomaceous earth to remove salts and catalyst. The filtrate was cooled to room temperature, washed three times with water, and the organic phase was retained. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (Vdichloromethane:Vpetroleum ether = 10:4) to obtain compound-607. (3.66g, yield, 49.16%, Mw: 703.89) The obtained compound -607 was analyzed, and the results are as follows: HPLC purity: >99%.

[0043] Mass spectrometry test: theoretical value 703.89; test value 703.52.

[0044] Elemental analysis: The calculated values ​​are: C, 90.44; H, 5.30; N, 1.99; O, 2.27.

[0045] The test values ​​were: C, 90.18; H, 5.62; N, 2.22; O, 2.51.

[0046] Example 4 ; Dissolve raw material A-630 (30.00 mmol) in toluene solution and raw material B-630 (30.00 mmol) in toluene solution. Then slowly add the raw material B-630 solution dropwise to the raw material A-630 solution. Next, after three venting cycles, tris(dibenzylacetone)dipalladium (0.30 mmol), tri-tert-butylphosphine (1.50 mmol), and sodium tert-butoxide (60.00 mmol) were added under nitrogen protection. The mixture was stirred until homogeneous, heated to 90 °C, and refluxed for 5 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The solid organic matter was completely dissolved with a small amount of dichloromethane and then slowly added dropwise to a petroleum ether solution. After stirring until homogeneous, a precipitate formed. The precipitate was filtered to obtain a solid, which was washed successively with 300 mL of anhydrous ethanol and 200 mL of petroleum ether, and then dried to obtain intermediate 1 (8.87 g, yield: 69.47%). Intermediate 1 (18.80 mmol) was dissolved in toluene solution, and raw material C-630 (18.80 mmol) was dissolved in toluene solution. Then, the raw material C-630 solution was slowly added dropwise to the intermediate 1 solution. Next, after three venting cycles, tris(dibenzylacetone)dipalladium (0.19 mmol), tri-tert-butylphosphine (0.94 mmol), and sodium tert-butoxide (37.60 mmol) were added under nitrogen protection. The mixture was stirred until homogeneous, heated to 90 °C, and refluxed for 5 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered through diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The solid organic matter was completely dissolved in a small amount of dichloromethane and then slowly added dropwise to a petroleum ether solution. After stirring until homogeneous, a precipitate formed. The precipitate was filtered to obtain a solid, which was washed successively with 300 mL of anhydrous ethanol and 200 mL of petroleum ether, and then dried to obtain intermediate 2 (6.92 g, yield: 58.77%). Intermediate 2 (9.58 mmol) was dissolved in a mixed solution of toluene, ethanol, and water, and starting material D-630 (9.58 mmol) was dissolved in the same mixed solution. The D-630 solution was then slowly added dropwise to the intermediate 2 solution. Under nitrogen protection, cesium carbonate (19.16 mmol), tri-tert-butylphosphine (0.48 mmol), and tris(dibenzylacetone)palladium (0.48 mmol) were added, stirred until homogeneous, heated to 90 °C, and refluxed for 6 h. After the reaction was complete, the temperature was slightly lowered, and the mixture was filtered through diatomaceous earth to remove salts and catalyst. The filtrate was cooled to room temperature, washed three times with water, and the organic phase was retained. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (Vdichloromethane:Vpetroleum ether = 10:4) to obtain compound-630. (3.37g, yield, 47.22%, Mw: 743.91) The obtained compound -630 was analyzed, and the results are as follows: HPLC purity: >99%.

[0047] Mass spectrometry test: theoretical value 743.91; test value 743.68.

[0048] Elemental analysis: The calculated values ​​are: C, 88.80; H, 5.01; N, 1.88; O, 4.30.

[0049] The test values ​​were: C, 88.57; H, 5.32; N, 2.04; O, 4.56.

[0050] Since the general structural formula is Chemical Formula I as described in the invention, the synthetic routes and principles of other compounds are the same as those listed in the examples above. Specifically, Examples 5-85 of this invention, prepared according to the above method, yield the luminescent auxiliary materials shown in Table 1 below: Table 1: Example compound Molecular formula theoretical value of mass spectrometry Mass spectrometry test values Device Example 5 1 <![CDATA[C 43 H 31 NS]]> 593.79 593.55 Device Example 6 2 <![CDATA[C 43 H 31 NS]]> 593.79 593.67 Device Example 7 3 <![CDATA[C 43 H 31 NS]]> 593.79 593.70 Device Example 8 10 <![CDATA[C 43 H 31 NS]]> 593.79 593.63 Device Example 9 20 <![CDATA[C 43 H 31 NS]]> 593.79 593.74 Device Example 10 24 <![CDATA[C 47 H 39 NS]]> 649.90 649.81 Device Example 11 30 <![CDATA[C 47 H 33 NS]]> 643.85 643.69 Device Example 12 34 <![CDATA[C 47 H 33 NS]]> 643.85 643.58 Device Example 13 37 <![CDATA[C 47 H 33 NS]]> 643.85 643.55 Device Example 14 46 <![CDATA[C 47 H 33 NS]]> 643.85 643.61 Device Example 15 79 <![CDATA[C 49 H 35 NS]]> 669.89 669.70 Device Example 16 94 <![CDATA[C 49 H 35 NS]]> 669.89 669.71 Device Example 17 95 <![CDATA[C 49 H 35 NS]]> 669.89 669.80 Device Example 18 103 <![CDATA[C 49 H 35 NS]]> 669.89 669.74 Device Example 19 137 <![CDATA[C 54 H 38 N2S]]> 746.97 746.69 Device Example 20 138 <![CDATA[C 54 H 38 N2S]]> 746.97 746.72 Device Example 21 139 <![CDATA[C 54 H 38 N2S]]> 746.97 746.83 Device Example 22 140 <![CDATA[C 54 H 38 N2S]]> 746.97 746.77 Device Example 23 144 <![CDATA[C 55 H 39 NS]]> 745.98 745.82 Device Example 24 147 <![CDATA[C 55 H 39 NS]]> 745.98 745.90 Device Example 25 168 <![CDATA[C 55 H 39 NS]]> 745.98 745.83 Device Example 26 177 <![CDATA[C 53 H 37 NS]]> 719.95 719.86 Device Example 27 181 <![CDATA[C 57 H 39 NS]]> 770.01 769.77 Device Example 28 195 <![CDATA[C 55 H 41 NS]]> 748.00 747.89 Device Example 29 234 <![CDATA[C 53 H 37 NS]]> 719.95 719.67 Device Example 30 238 <![CDATA[C 53 H 37 NS]]> 719.95 719.74 Device Example 31 242 <![CDATA[C 57 H 37 WE]]> 783.99 783.87 Device Example 32 245 <![CDATA[C 55 H 37 WE]]> 759.97 759.73 Device Example 33 246 <![CDATA[C 55 H 37 WE]]> 759.97 759.82 Device Example 34 247 <![CDATA[C 57 H 37 WE]]> 783.99 783.85 Device Example 35 248 <![CDATA[C 57 H 37 WE]]> 783.99 783.77 Device Example 36 250 <![CDATA[C 49 H 33 WE]]> 683.87 683.69 Device Example 37 251 <![CDATA[C 49 H 33 WE]]> 683.87 683.72 Device Example 38 257 <![CDATA[C 49 H 33 WE]]> 683.87 683.76 Device Example 39 275 <![CDATA[C 49 H 33 NS2]]> 699.93 699.73 Device Example 40 284 <![CDATA[C 53 H 35 NS2]]> 749.99 749.83 Device Example 41 288 <![CDATA[C 49 H 33 NS2]]> 699.93 699.67 Device Example 42 291 <![CDATA[C 49 H 33 WE]]> 683.87 683.68 Device Example 43 292 <![CDATA[C 49 H 33 WE]]> 683.87 683.76 Device Example 44 317 <![CDATA[C 55 H 37 NS2]]> 776.03 775.90 Device Example 45 320 <![CDATA[C 55 H 37 NS2]]> 776.03 775.84 Device Example 46 386 <![CDATA[C 43 H 31 NO]]> 577.73 577.51 Device Example 47 391 <![CDATA[C 45 H 35 NO]]> 605.78 605.49 Device Example 48 392 <![CDATA[C 43 H 31 NO]]> 577.73 577.55 Device Example 49 394 <![CDATA[C 43 H 31 NO]]> 577.73 577.61 Device Example 50 418 <![CDATA[C 47 H 33 NO]]> 627.79 627.54 Device Example 51 425 <![CDATA[C 47 H 33 NO]]> 627.79 627.63 Device Example 52 429 <![CDATA[C 47 H 33 NO]]> 627.79 627.70 Device Example 53 442 <![CDATA[C 47 H 33 NO]]> 627.79 627.59 Device Example 54 466 <![CDATA[C 49 H 35 NO]]> 653.83 653.67 Device Example 55 509 <![CDATA[C 55 H 39 NO]]> 729.92 729.84 Device Example 56 524 <![CDATA[C 54 H 38 N2O]]> 730.91 730.66 Device Example 57 528 <![CDATA[C 55 H 39 NO]]> 729.92 729.78 Device Example 58 531 <![CDATA[C 55 H 39 NO]]> 729.92 729.80 Device Example 59 533 <![CDATA[C 55 H 39 NO]]> 729.92 729.79 Device Example 60 538 <![CDATA[C 55 H 39 NO]]> 729.92 729.81 Device Example 61 548 <![CDATA[C 55 H 39 NO]]> 729.92 729.84 Device Example 62 552 <![CDATA[C 55 H 39 NO]]> 729.92 729.67 Device Example 63 570 <![CDATA[C 59 H 41 NO]]> 779.98 779.81 Device Example 64 571 <![CDATA[C 59 H 41 NO]]> 779.98 779.85 Device Example 65 579 <![CDATA[C 55 H 41 NO]]> 731.94 731.85 Device Example 66 603 <![CDATA[C 57 H 45 NO]]> 759.99 759.84 Device Example 67 626 <![CDATA[C 57 H 37 NO2]]> 767.93 767.83 Device Example 68 629 <![CDATA[C 55 H 37 NO2]]> 743.91 743.69 Device Example 69 634 <![CDATA[C 49 H 33 NO2]]> 667.81 667.59 Device Example 70 635 <![CDATA[C 49 H 33 NO2]]> 667.81 667.72 Device Example 71 638 <![CDATA[C 49 H 33 NO2]]> 667.81 667.59 Device Example 72 639 <![CDATA[C 49 H 33 NO2]]> 667.81 667.65 Device Example 73 642 <![CDATA[C 49 H 33 NO2]]> 667.81 667.76 Device Example 74 757 <![CDATA[C 55 H 38 N2O]]> 742.92 742.81 Device Example 75 758 <![CDATA[C 55 H 38 N2O]]> 742.92 742.77 Device Example 76 759 <![CDATA[C 55 H 38 N2O]]> 742.92 742.80 Device Example 77 760 <![CDATA[C 55 H 38 N2O]]> 742.92 742.73 Device Example 78 769 <![CDATA[C 49 H 36 N2]]> 652.84 652.61 Device Example 79 772 <![CDATA[C 49 H 36 N2]]> 652.84 652.71 Device Example 80 786 <![CDATA[C 49 H 36 N2]]> 652.84 652.65 Device Example 81 810 <![CDATA[C 53 H 38 N2]]> 702.90 702.83 Device Example 82 937 <![CDATA[C 49 H 35 NS]]> 669.89 669.83 Device Example 83 938 <![CDATA[C 49 H 35 NS]]> 669.89 669.75 Device Example 84 963 <![CDATA[C 49 H 35 NO]]> 653.83 653.69 Device Example 85 964 <![CDATA[C 49 H 35 NO]]> 653.83 653.74 When the organic electroluminescent device prepared using the light-emitting auxiliary material provided in the above embodiments includes a light-emitting auxiliary layer, the light-emitting auxiliary layer includes the light-emitting auxiliary material provided in the above embodiments.

[0051] Device Example 1: Fabrication of a Red Organic Light Emitting Device The structure of the fabricated OLED device is as follows: ITO anode / HIL / HTL / light-emitting auxiliary layer / EML / HBL / ETL / EIL / cathode / light extraction layer a. ITO anode: The ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate with a coating thickness of 1500 Å was cleaned twice in distilled water and ultrasonically washed for 30 min. Then it was cleaned twice more in distilled water and ultrasonically washed for 10 min. After washing, it was ultrasonically washed sequentially with methanol, acetone and isopropanol (5 min each time). After drying, it was transferred to a plasma cleaner for 5 min and then sent to a vapor deposition machine. Using this substrate as the anode, other functional layers were sequentially vapor deposited on it.

[0052] b. HIL (Hole Injection Layer): Hole injection layer materials HT-1 and P-dopant, with chemical formulas shown below, are vacuum-deposited at a deposition rate of 1 Å / s. The deposition rate ratio of HT-1 to P-dopant is 97:3, and the thickness is 10 nm. c. HTL (hole transport layer): HT-1 of 130 nm was vacuum-deposited on the hole injection layer at a deposition rate of 1.5 Å / s as a hole transport layer. d. Light-emitting auxiliary layer: Compound 4 provided in the above embodiment was vacuum-deposited on the hole transport layer at a deposition rate of 0.5 Å / s for 10 nm as a light-emitting auxiliary layer; e. EML (Emitting Layer): Then, on the above-mentioned emitting auxiliary layer, a host material (Host-1) and a dopant material (Dopant-1) with a thickness of 20 nm are vacuum-deposited at a deposition rate of 1 Å / s as the emitting layer. The chemical formulas of Host-1 and Dopant-1 are shown below. The deposition rate ratio of the two Host-1 and Dopant-1 is 98:2.

[0053] f. HBL (hole blocking layer): A hole blocking layer HB with a thickness of 5.0 nm is vacuum-deposited at a deposition rate of 0.5 Å / s.

[0054] g. ETL (Electron Transport Layer): ET-1 and Liq with a thickness of 35 nm were vacuum-deposited at a deposition rate of 1 Å / s as the electron transport layer. The chemical formula of ET-1 is shown below. The deposition rate ratio of ET-1 to Liq is 50:50.

[0055] h. EIL (Electron Injection Layer): A 1.0 nm Yb film is deposited at a deposition rate of 0.5 Å / s to form an electron injection layer.

[0056] i. Cathode: Magnesium and silver are deposited at a deposition rate of 1 Å / s for 18 nm, with a deposition rate ratio of 1:9, to obtain the OLED device.

[0057] j. Optical extraction layer: CPL-1 with a thickness of 70 nm was vacuum-deposited on the cathode at a deposition rate of 1 Å / s as the optical extraction layer.

[0058] K. Subsequently, the vapor-deposited substrate is encapsulated. First, the cleaned cover plate is coated with UV adhesive using an adhesive coating equipment. Then, the coated cover plate is moved to the lamination section, and the vapor-deposited substrate is placed on the top of the cover plate. Finally, the substrate and cover plate are laminated under the action of the lamination equipment, while the UV adhesive is cured by light.

[0059] .

[0060] Referring to the method provided in Embodiment 1 of the above-mentioned device, the following compounds were selected respectively: 1, 2, 3, 10, 20, 24, 30, 34, 37, 46, 79, 94, 95, 103, 137, 138, 139, 140, 144, 147, 168, 177, 181, 195, 234, 238, 242, 245, 246, 247, 248, 250, 251, 257, 261, 275, 284, 288, 291, 292, 317, 320, 386, 391, 392, 394, 418, 4 Compound 4 was replaced by compounds 25, 429, 442, 466, 509, 524, 528, 531, 533, 538, 548, 552, 570, 571, 579, 603, 607, 626, 629, 630, 634, 635, 638, 639, 642, 757, 758, 759, 760, 769, 772, 786, 810, 937, 938, 963, and 964. A light-emitting auxiliary layer was deposited, and corresponding organic electroluminescent devices were prepared, which are referred to as Device Examples 2 to 85.

[0061] Device Comparison Example 1: This comparative example provides an organic electroluminescent device. The only difference between this organic electroluminescent device and device example 1 is that the organic electroluminescent device uses existing comparative compound a instead of the light-emitting auxiliary material (compound 4) in device example 1 for vapor deposition. The chemical structural formula of comparative compound a is as follows: Device Comparison Example 2: This comparative example provides an organic electroluminescent device. The only difference between this organic electroluminescent device and device example 1 is that the organic electroluminescent device uses existing comparative compound b instead of the light-emitting auxiliary material (compound 4) in device example 1 for vapor deposition. The chemical structural formula of comparative compound b is as follows: Device Comparison Example 3: This comparative example provides an organic electroluminescent device. The only difference between this organic electroluminescent device and device example 1 is that the organic electroluminescent device uses existing comparative compound c instead of the light-emitting auxiliary material (compound 4) in device example 1 for vapor deposition. The chemical structural formula of comparative compound c is as follows: Device Comparison Example 4: This comparative example provides an organic electroluminescent device. The only difference between this organic electroluminescent device and device example 1 is that the organic electroluminescent device uses existing comparative compound d instead of the light-emitting auxiliary material (compound 4) in device example 1 for vapor deposition. The chemical structural formula of comparative compound d is as follows: Device Comparison Example 5: This comparative example provides an organic electroluminescent device. The only difference between this organic electroluminescent device and device example 1 is that the organic electroluminescent device uses existing comparative compound e instead of the light-emitting auxiliary material (compound 4) in device example 1 for vapor deposition. The chemical structural formula of comparative compound e is as follows: Device Comparison Example 6: This comparative example provides an organic electroluminescent device. The only difference between this organic electroluminescent device and device example 1 is that the organic electroluminescent device uses existing comparative compound f instead of the light-emitting auxiliary material (compound 4) in device example 1 for vapor deposition. The chemical structural formula of comparative compound f is as follows: Device Comparison Example 7: This comparative example provides an organic electroluminescent device. The only difference between this organic electroluminescent device and device example 1 is that the organic electroluminescent device uses existing comparative compound f instead of the light-emitting auxiliary material (compound 4) in device example 1 for vapor deposition. The chemical structural formula of comparative compound g is as follows: .

[0062] The driving voltage, luminous efficiency, and lifetime of the organic electroluminescent devices obtained in Examples 1-85 and Comparative Examples 1-7 were characterized at a brightness of 6000 nits. The test results are shown in Table 2 below. Table 2: As shown in Table 2, changing the substituents and their positions alters the device performance. In dibenzothiophene, dibenzofuran, and dibenzocarbazole, the different electronegativity of carbon, oxygen, and nitrogen leads to varying HOMO and LUMO values. Furthermore, dibenzofuran exhibits relatively higher electrochemical stability. Compared to existing organic electroluminescent devices using the luminescent auxiliary materials provided in this invention, the organic electroluminescent devices prepared using these materials show improved lifetimes.

[0063] The above description of the disclosed embodiments enables those skilled in the art to make or use the invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the invention. Therefore, the invention is not 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

1. A luminescent auxiliary material, characterized in that, Specifically, it includes the following structure: 。 2. An application of the luminescent auxiliary material as described in claim 1, characterized in that, The application of the light-emitting auxiliary material in the preparation of organic light-emitting devices, organic solar cells, electronic paper, organic photoreceptors, or organic thin-film transistors.

3. An organic electroluminescent device, characterized in that, It includes a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode; and, The organic layer includes at least one of the following: a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron injection and transport layer; and, The hole injection layer is made of materials including metalloporphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and conductive polymers based on polyaniline and polythiophene. The hole transport layer is made of materials including arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions. The main material of the light-emitting layer includes fused aromatic ring derivatives and heterocyclic compounds; wherein, the fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. The electron transport layer is made of materials including Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, and hydroxyflavonoid-metal complexes; and the thickness of the electron transport layer is 1-50 nm. The materials of the electron injection layer include fluorenone, anthraquinone dimethane, biphenylquinone, thiam dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenemethane, anthrone and its derivatives, metal complexes, and nitrogen-containing 5-membered ring derivatives; Furthermore, the organic layer comprises one or more light-emitting auxiliary materials as described in claim 1.

Images