Light-emitting auxiliary layer material, preparation method and organic electroluminescent device comprising light-emitting auxiliary layer material

Abstract

The invention belongs to the field of organic electroluminescence, and discloses a light-emitting auxiliary layer material, a preparation method and an organic electroluminescence device containing the light-emitting auxiliary layer material. The structure of the material of the light-emitting auxiliary layer is as shown in a chemical formula I: # imgabs0. The compound of the material of the light-emitting auxiliary layer provided by the invention takes a benzo-naphthofuran group and a triarylamine group as a parent nucleus main body through bridging of a naphthylene group, and the rigid benzo-naphthofuran structure can effectively enhance the structural stability; the hole transport efficiency of the material can be improved due to the existence of the triarylamine group, a more efficient conjugated system can be formed between the two main body structures through bridging naphthylene, the electron mobility of the whole material is improved, and the device has lower driving voltage, high luminous efficiency and long service life.

Description

Technical Field

[0001] The present invention belongs to the field of organic electroluminescence, and relates to a material applied to a blue light device, and in particular to a luminescent auxiliary layer material, a preparation method and an organic electroluminescent device comprising the same. Background Art

[0002] Organic light-emitting diodes (OLEDs) have a multi-layer "sandwich" structure, including electrode material layers and organic functional materials sandwiched between different electrode film layers, including: hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer. In order to reduce the potential barrier between the hole transport layer and the light-emitting layer and lower the driving voltage of the OLED, a light-emitting auxiliary layer is usually set between the two to improve the utilization rate of holes, thereby improving the OLED's luminous efficiency, stability, and lifespan.

[0003] The compounds that can be used as light-emitting auxiliary layer materials mainly include hydrazones, carbazoles, oxadiazoles, triarylamines, styrenes and butadiene, among which triarylamine materials can form ammonium ion radicals under the action of an electric field, have a high hole mobility and good photoelectric properties. Triarylamine compounds are centered on nitrogen atoms and connected to three substituents, with a propeller-like structure. The large steric hindrance and hyperconjugation effect make the nitrogen atom radicals have a high stability. This unique free radical property makes this type of compound have a high hole mobility.

[0004] At present, there are few materials that can be used as the light-emitting auxiliary layer in blue light devices and have excellent device performance. In particular, the device life and luminous efficiency are not significantly improved. Therefore, developing a light-emitting auxiliary material with high luminous efficiency, long service life and low driving voltage has always been an urgent problem to be solved by researchers in this field. Summary of the invention

[0005] In view of the deficiencies in the prior art, the present invention discloses a luminescent auxiliary layer material, a preparation method and an organic electroluminescent device comprising the same.

[0006] It should be noted that the light-emitting auxiliary layer material structure disclosed in the present invention is based on a benzonaphthofuran group and a triarylamine group connected by a naphthyl bridge as the main core body. The rigid benzonaphthofuran structure can effectively enhance the structural stability. The presence of the triarylamine group can improve the hole transport efficiency of the material. A more efficient conjugated system can be formed between the two main structures through the bridging naphthyl group, thereby improving the electron mobility of the entire material, so that the device has a lower driving voltage, high luminous efficiency and long service life.

[0007] In order to achieve the above objectives, the first objective of the present invention is to provide a luminescent auxiliary layer material, which adopts the following technical solution:

[0008] A light-emitting auxiliary layer material, the general structural formula of the light-emitting auxiliary layer material is shown in Chemical Formula I:

[0009]

[0010] in,

[0011] They are connected to a benzene ring of naphthalene. The connection position of the two can be selected from 1 or 2, and the two are connected in the ortho position. The connection position of the naphthalene group is as follows:

[0012] R 1 is selected from hydrogen, substituted or unsubstituted C6-C12 aryl;

[0013] Ar 1 ,Ar 2 They are independently selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C5-C30 heteroaryl groups; and their heteroatoms contain at least one of O, S, N, Si and Se.

[0014] Furthermore, the chemical formula I has the following structures of chemical formulas IA to IB:

[0015]

[0016] Furthermore, R 1 is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl.

[0017] Furthermore, Ar 1 ,Ar 2 Independently selected from the following structures:

[0018]

[0019] in,

[0020] R 2 -R 13 Each is independently selected from hydrogen, deuterium, deuterium-substituted or unsubstituted C1-C6 alkyl;

[0021] n 2 、n 10 are independently selected from integers from 1 to 5;

[0022] n 3 、n 7 are independently selected from integers from 1 to 9;

[0023] n 4 、n 5 、n12 are independently selected from integers from 1 to 13;

[0024] n 6 、n 8 are independently selected from integers from 1 to 7;

[0025] n 9 independently selected from integers from 1 to 8;

[0026] n 11 、n 13 are independently selected from integers from 1 to 11.

[0027] It should be noted that the "substituted" in the substituted or unsubstituted is selected from deuterium, halogen, cyano, TMS, trifluoromethyl, 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, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, 1-methylhexyl, cyclopentane, cyclohexane, phenyl, biphenyl, naphthyl, fluorenyl, dimethylfluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylene, pyrenyl, The invention relates to benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, benzothiadiazolyl, carbazolyl, benzocarbazolyl, or substituted with two or more of the substituents shown above which are linked together.

[0028] In the above technical solution, the light-emitting auxiliary layer material is any one of the following structures, but is not limited thereto:

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037] The second object of the present invention is to provide a method for preparing the light-emitting auxiliary layer material as described above.

[0038] It should be noted that the light-emitting auxiliary layer material in the present invention can be prepared by methods known to those skilled in the art. Alternatively, the following reaction process is preferred for preparation, and the specific operation is as follows:

[0039] (1) Add raw material A (1.0 eq), raw material B (1.0-1.3 eq), potassium carbonate (2.0-4.0 eq) and a mixed solution of toluene, ethanol and water (V:V:V=3:1:1) to a reaction flask, protect with nitrogen, then add tetrakis(triphenylphosphine)palladium (0.01-0.03 eq), then heat to 75-95° C. and stir to react for 1-14 h; detect the reaction by thin layer chromatography to confirm the completion of the reaction, cool, add water and dichloromethane for extraction and separation, combine the organic phases and concentrate, and purify by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=1:3-1:10) to obtain intermediate 1;

[0040] (2) Add intermediate 1 (1.0-1.3 eq), raw material C (1.0 eq), sodium tert-butoxide (2.0-4.0 eq) and toluene to a reaction flask, protect with nitrogen, then add tri(dibenzylideneacetone)dipalladium (0.01-0.05 eq) and tri-tert-butylphosphine (0.01-0.10 eq), then heat to 110-120° C. and stir to react for 4-24 h; detect the reaction by thin layer chromatography to confirm the completion of the reaction, cool, add water and dichloromethane for extraction and separation, combine the organic phases and concentrate, and purify by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=1:4-1:12) to obtain chemical formula I;

[0041] The specific synthetic route is as follows:

[0042]

[0043] In the formula, R 1 ,Ar 1 ,Ar 2 As defined in the above chemical formula I, X independently represents Where * is the attachment site.

[0045] In particular, for complex raw materials that are not disclosed, the classical Suzuki coupling reaction and Buchwald-Hartwig coupling reaction are used for synthesis and applied to the present invention.

[0046] The third object of the present invention is to provide an application of a luminescent auxiliary layer material, wherein the luminescent auxiliary layer material as described above is applied to an organic electroluminescent device.

[0047] Specifically, the organic electroluminescent device includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode.

[0048] It should be noted that the organic material layer of the organic electroluminescent device in the present invention can be formed into a single-layer structure or a multilayer structure having two or more organic material layers. For example, the organic electroluminescent device may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic material layers or a larger number of organic material layers.

[0049] Specifically, except that the light-emitting auxiliary layer of the present invention contains chemical formula I, there is no special limitation on the materials of other layers in the OLED device.

[0050] Further, the organic electroluminescent device can be used in an organic electroluminescent device, which includes but is not limited to a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for internal or external lighting and / or signaling, a head-up display, a fully transparent or partially transparent display, a flexible display, a laser printer, a telephone, a mobile phone, a tablet, a photo album, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or venue screen, a light therapy device and a sign.

[0051] Compared with the prior art, the present invention provides a luminescent auxiliary layer material, a preparation method and an organic electroluminescent device containing the same, which have the following excellent effects:

[0052] The material compound disclosed in the present invention has a benzonaphthofuran group and a triarylamine group connected by a naphthyl bridge as a parent core main structure, and is used as a luminescent auxiliary layer material to enable the device to have a lower driving voltage, high thermal stability, high luminous efficiency and long service life.

[0053] Specifically, 1) the benzonaphthofuran group itself has strong rigidity and can withstand high temperatures without decomposition, which can effectively improve the electrochemical stability and thermal stability of the overall structure, making the material less likely to undergo structural changes under high-temperature evaporation, which is crucial for improving the long-term stability and life of OLED devices;

[0054] 2) Due to the presence of nitrogen atoms containing lone pairs of electrons in triarylamine, the electrons on the nitrogen atoms are transferred by transition under the action of an external electric field, so that holes are generated in the molecule, thereby realizing the reverse transfer of holes; and the triarylamine group itself has hole transport properties, which is conducive to the efficient transfer of holes from the anode to the light-emitting layer, and reduces the energy loss during the hole transfer process. Further connecting a group that matches its energy level to the triarylamine structure is to add a geometric structure to the non-planar molecular structure to form a compound with a larger spatial configuration, which is more conducive to the transfer of holes, obtains better hole transfer efficiency, and thus improves the luminous efficiency of the device;

[0055] 3) A bridging naphthylene group is introduced between the benzonaphthofuran group and the triarylamine group. The two are connected at the ortho position on the same benzene ring of the naphthylene group (located at the 1 and 2 positions of the naphthyl group). This connection method can effectively increase the packing density of the molecule, which is beneficial to the transfer of charge. It can form a longer and more effective conjugated system with it, improve the electron mobility of the entire material, and thus help to improve the luminous efficiency of the device; and the rigidity of the naphthylene group helps the orderly arrangement of the molecules, adjusts the energy level of the entire molecule, balances the transfer of electrons and holes, ensures the charge balance in the device, and can also improve the thermal stability of the molecule, making the material less likely to undergo structural changes and cracking during high-temperature evaporation, thereby increasing the service life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0056] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are only embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on the provided drawings without paying creative work.

[0057] Figure 1 is the H NMR spectrum of compound 1. DETAILED DESCRIPTION

[0058] The technical solution of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention and the related drawings. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0059] The invention specifically discloses a luminescent auxiliary layer material, a preparation method and an organic electroluminescent device containing the same.

[0060] It should be noted that the numerical values ​​given in the following examples are as accurate as possible, but due to inevitable measurement errors and experimental operation problems of those skilled in the art, each number should be understood as an approximate number rather than an absolutely accurate value.

[0061] The specific embodiments described below are only part of the embodiments of the present application, rather than all the embodiments.

[0062] The features and performance of the present invention will be further described in detail below with reference to the embodiments.

[0063] Example 1

[0064]

[0065] Step 1 specifically includes the following processes:

[0066] Raw material A-1 (1.0 eq, CAS number: 2261008-21-1), raw material B-1 (1.1 eq, CAS number: 71436-66-3), potassium carbonate (3.0 eq) and a mixed solution of toluene, ethanol and water (V:V:V = 3:1:1) were added to the reaction flask under nitrogen protection, and tetrakis(triphenylphosphine)palladium (0.01 eq) was added, and then the temperature was raised to 90°C and stirred for reaction for 5 hours; the reaction was detected by thin layer chromatography to confirm that the reaction was complete, the temperature was lowered, water and dichloromethane were added for extraction and separation, the organic phases were combined and concentrated, and a mixed solution of dichloromethane and petroleum ether (V:V = 1:5) was used for purification by column chromatography to obtain intermediate 1 (yield: 76.8%).

[0067] Step 2 specifically includes the following processes:

[0068] Intermediate 1 (1.0 eq), raw material C-1 (1.0 eq, CAS number: 955959-90-7), sodium tert-butoxide (3.0 eq) and toluene were added to the reaction flask under nitrogen protection, and tri(dibenzylideneacetone)dipalladium (0.03 eq) and tri-tert-butylphosphine (0.05 eq) were added, and then the temperature was raised to 120° C. and stirred for reaction for 18 h; the reaction was detected by thin layer chromatography to confirm that the reaction was complete, the temperature was lowered, water and dichloromethane were added for extraction and separation, the organic phases were combined and concentrated, and a mixed solution of dichloromethane and petroleum ether (V:V=1:5) was used for purification by column chromatography to obtain compound 1 (yield: 83.4%).

[0069] The obtained compound 1 was tested and analyzed, and the results were as follows:

[0070] HPLC purity: >99.8%.

[0071] Mass spectrometry test: The model is Waters XEVO TQD mass spectrometer, using ESI source.

[0072] Test value MS (ESI, m / Z): [M+H] + =727.49.

[0073] Elemental Analysis:

[0074] Calculated values: C, 89.11; H, 4.57; N, 1.92; O, 4.40;

[0075] The test values ​​are: C, 88.82; H, 4.68; N, 2.05; O, 4.52.

[0076] H NMR spectrum: Figure 1 (Compound 1) shown.

[0077] Example 2

[0078]

[0079] Step 1 specifically includes the following processes:

[0080] Raw material A-181 (1.0 eq, CAS number: 2025367-45-5), raw material B-181 (1.1 eq, CAS number: 692728-68-0), potassium carbonate (3.0 eq) and a mixed solution of toluene, ethanol and water (V:V:V = 3:1:1) were added to the reaction flask, protected by nitrogen, and tetrakis(triphenylphosphine)palladium (0.01 eq) was added, and then the temperature was raised to 90°C and stirred for reaction for 6 hours; the reaction was detected by thin layer chromatography to confirm that the reaction was complete, the temperature was lowered, water and dichloromethane were added for extraction and separation, the organic phases were combined and concentrated, and a mixed solution of dichloromethane and petroleum ether (V:V = 1:6) was used for purification by column chromatography to obtain intermediate 1 (yield: 75.7%).

[0081] Step 2 specifically includes the following processes:

[0082] Intermediate 1 (1.0 eq), raw material C-181 (1.0 eq, CAS number: 897921-59-4), sodium tert-butoxide (3.0 eq) and toluene were added to the reaction flask under nitrogen protection, and tri(dibenzylideneacetone)dipalladium (0.03 eq) and tri-tert-butylphosphine (0.05 eq) were added, and then the temperature was raised to 120°C and stirred for reaction for 16 hours; the reaction was detected by thin layer chromatography to confirm the completion of the reaction, the temperature was lowered, water and dichloromethane were added for extraction and separation, the organic phases were combined and concentrated, and a mixed solution of dichloromethane and petroleum ether (V:V=1:5) was used for purification by column chromatography to obtain compound 181 (yield: 82.8%).

[0083] The obtained compound 181 was tested and analyzed, and the results were as follows:

[0084] HPLC purity: >99.8%.

[0085] Mass spectrometry test: The model is Waters XEVO TQD mass spectrometer, using ESI source.

[0086] Test value MS (ESI, m / Z): [M+H] + =713.51.

[0087] Elemental Analysis:

[0088] Calculated values: C, 90.85; H, 4.94; N, 1.96; O, 2.24;

[0089] The test values ​​are: C, 90.57; H, 5.06; N, 2.08; O, 2.35.

[0090] Example 3-57

[0091] The following compounds were synthesized by referring to the preparation methods of Examples 1 to 2, and tested using a Waters XEVOTQD mass spectrometer with low precision. The ESI source was used for testing, and the mass spectrometry test values ​​are shown in Table 1 below.

[0092] Table 1 Mass spectrometry test values ​​of Examples 3-57

[0093]

[0094]

[0095] In addition, it should be noted that other compounds of the present invention can be obtained by referring to the preparation methods of the above-mentioned embodiments, so they are not listed one by one here.

[0096] The organic electroluminescent device provided by the present invention is described below in conjunction with specific embodiments.

[0097] Device Example 1: Preparation of Blue Light Organic Electroluminescent Device

[0098] The structure of the prepared OLED device is: ITO anode / HIL / HTL / Prime / EML / HBL / ETL / EIL / cathode / CPL.

[0099] a. ITO anode: the coating thickness is The ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate was cleaned in distilled water for 3 times, ultrasonically cleaned for 40 minutes, and then repeatedly cleaned with distilled water for 3 times, ultrasonically cleaned for 20 minutes. After washing, it was ultrasonically cleaned with methanol, acetone, and isopropanol in sequence (5 minutes each time), dried, and then transferred to a plasma cleaning machine for washing for 5 minutes. It was then sent to a vapor deposition machine, and the substrate was used as the anode, and other functional layers were deposited thereon in sequence.

[0100] b. HIL (hole injection layer): The hole injection layer materials HT and P-dopant were vacuum evaporated at a deposition rate of 97:3, and the thickness was 10 nm. The chemical formula of the materials is shown below.

[0101] c. HTL (hole transport layer): At a deposition rate of , HT with a thickness of 125 nm was vacuum-deposited on the hole injection layer as a hole transport layer.

[0102] d. Prime (luminous auxiliary layer): At a deposition rate of , the compound 1 provided in the above embodiment is vacuum evaporated on the hole transport layer with a thickness of 5 nm as a light-emitting auxiliary layer.

[0103] e. EML (luminescent layer): At a evaporation rate of , a host material (Host) and a dopant material (Dopant) with a thickness of 25 nm are vacuum evaporated on the light-emitting auxiliary layer as a light-emitting layer. The chemical formulas of Host and Dopant are shown below, and the evaporation rate ratio of Host and Dopant is 98:2.

[0104] f. HBL (hole blocking layer): At a deposition rate of , a hole blocking layer HB with a thickness of 5 nm was vacuum-deposited on the light-emitting layer.

[0105] g. ETL (Electron Transport Layer): At a evaporation rate of , ET and Liq with a thickness of 30 nm were vacuum evaporated on the hole blocking layer as an electron transport layer. The chemical formula of ET is shown below, where the evaporation rate ratio of ET and Liq is 50:50.

[0106] h. EIL (electron injection layer): At a deposition rate of , a Yb film layer with a thickness of 1 nm is vacuum-deposited on the electron transport layer to form an electron injection layer.

[0107] i. Cathode: At a deposition rate of , magnesium and silver with a thickness of 13 nm were vacuum evaporated on the electron injection layer. The deposition rate ratio of magnesium to silver was 1:9, to obtain a cathode.

[0108] j. CPL (light extraction layer): At a deposition rate of , CPL with a thickness of 60 nm was vacuum-deposited on the cathode as a light extraction layer.

[0109] k. Package the vapor-deposited substrate: first, use the glue coating equipment to coat the cleaned cover with UV glue, then move the coated cover to the pressing section, place the vapor-deposited substrate on the upper end of the cover, and finally bond the substrate and cover with the bonding equipment, and complete the light curing of the UV glue at the same time.

[0110] The structures of HT, P-dopant, Host, Dopant, HB, ET, and CPL used in the device embodiment 1 are as follows:

[0111]

[0112] Device Example 2-57:

[0113] Referring to the method provided in the above device embodiment 1, the corresponding compounds in Table 2 were selected to replace compound 1, and the luminescent auxiliary layer was evaporated to prepare the corresponding organic electroluminescent devices, which were respectively recorded as device embodiments 2-57.

[0114] Device Comparison Examples 1-9:

[0115] The comparative example provides an organic electroluminescent device, the preparation method of which is different from that of the device embodiment 1 in that the organic electroluminescent device uses the existing compound ai to replace the light-emitting auxiliary layer material (compound 1) in the device embodiment 1 for evaporation. The chemical structure of the compound ai is as follows:

[0116]

[0117] The driving voltage, luminous efficiency and life of the organic electroluminescent devices obtained from the device embodiments 1-57 and the device comparative examples 1-9 were characterized at a brightness of 1000 (nits). The test results are shown in Table 2 below:

[0118] Table 2 Device test results

[0119]

[0120]

[0121]

[0122]

[0123] Those skilled in the art know that in a blue top-emitting device, the luminous efficiency is greatly affected by chromaticity. Therefore, the influence of chromaticity on efficiency is taken into account, and the ratio of luminous efficiency to CIEy is defined as the BI value, that is, BI = (cd / A) / CIEy.

[0124] It can be seen from Table 2 that, compared with the organic electroluminescent device prepared using the light-emitting auxiliary layer material provided by the present invention and the organic electroluminescent device prepared using the comparative example compound, the luminous efficiency and service life of the device are effectively improved while maintaining a lower driving voltage.

[0125]

[0126] Compounds a, b, c and compounds 86, 30, 88 are parallel comparative examples, respectively, and the difference between them is that the triarylamine and the benzonaphthofuran group in compounds a, b, c are connected by chemical bonds, phenylene groups, and biphenylene groups, respectively, while the triarylamine and the benzonaphthofuran group in compounds 86, 30, 88 of the present invention are connected by a bridging naphthyl group. Compared with compound a, the introduction of the naphthyl group can effectively extend the conjugation length of the entire molecule, avoid localization of carrier migration, enhance the hole transport performance, and help improve the luminous efficiency and brightness of the device; compared with the phenylene and biphenylene groups between the triarylamine and the benzonaphthofuran group in compounds b and c, the naphthyl group in compounds 86, 30, 88 of the present invention has better rigidity, so that the material maintains structural stability during high-temperature evaporation, is not easy to degrade, and effectively improves the service life of the device.

[0127]

[0128] Compounds e and f and compounds 58 and 140 are parallel comparative examples, respectively. The difference between them is that in compounds e and f, the triarylamine is connected to a dibenzofuran group through a bridging naphthylene group, while in compounds 58 and 140 of the present invention, the triarylamine is connected to a benzonaphthofuran group through a bridging naphthylene group. The addition of an additional benzene ring to the dibenzofuran group effectively increases the conjugated area of ​​the overall structure, effectively improves the luminous efficiency of the device, and at the same time enhances the rigidity of the compound, so that the film-forming property and stability of the material during the evaporation process are better, thereby improving the service life of the device.

[0129]

[0130] Compounds g, h and compounds 142, 176 are parallel comparative examples, and the difference between them is that the triarylamine group and the benzonaphthofuran group in compounds g and h are respectively connected to the 1 and 4 positions of the naphthylene group serving as a bridging group in the middle, while the triarylamine group and the benzonaphthofuran group in compounds 142 and 176 of the present invention are connected to the 1 and 2 positions of the naphthylene group, which is an ortho-connection, making the overall structure of the molecule more tightly and orderly stacked, thereby improving the stability of the material and thus improving the life of the device.

[0131] The above description of the disclosed embodiments enables one skilled in the art to implement or use the present invention. Various modifications to these embodiments will be apparent to one 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 present invention. Therefore, the present invention will not be limited to the embodiments shown herein, but rather to the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A light-emitting auxiliary layer material, characterized in that: The general structural formula of the light-emitting auxiliary layer material is shown in Chemical Formula I: in, The two are connected to a benzene ring of naphthalene, and the positions where the two are connected can be selected from 1 or 2, and the two are connected in the ortho position; R1 is selected from hydrogen, substituted or unsubstituted C6-C12 aryl; Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C5-C30 heteroaryl groups, wherein the heteroatom contains at least one of O, S, N, Si and Se.

2. The light-emitting auxiliary layer material according to claim 1, characterized in that: Chemical formula I has the following structures of chemical formulas IA to IB:

3. The light-emitting auxiliary layer material according to claim 2, characterized in that: R1 is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl.

4. The light-emitting auxiliary layer material according to claim 2, characterized in that: Ar1 and Ar2 are independently selected from the following structures: in, R2-R 13 Each is independently selected from hydrogen, deuterium, deuterium-substituted or unsubstituted C1-C6 alkyl; n2、n 10 are independently selected from integers from 1 to 5; n3 and n7 are independently selected from integers from 1 to 9; n4, n5, n 12 are independently selected from integers from 1 to 13; n6 and n8 are independently selected from integers from 1 to 7; n9 is independently selected from an integer from 1 to 8; n 11 、n 13 are independently selected from integers from 1 to 11.

5. The light-emitting auxiliary layer material according to claim 3 or 4, characterized in that: The "substituted" in the substituted or unsubstituted is selected from deuterium, halogen, cyano, TMS, trifluoromethyl, 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, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, 1-methylhexyl, cyclopentane, cyclohexane, phenyl, biphenyl, naphthyl, fluorenyl, dimethylfluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylene, pyrenyl, The invention relates to benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, benzothiadiazolyl, carbazolyl, benzocarbazolyl, or substituted with two or more of the substituents shown above which are linked together.

6. The light-emitting auxiliary layer material according to claim 5, characterized in that: The structure of the light-emitting auxiliary layer material is selected from any one of the following compounds:

7. A method for preparing the light-emitting auxiliary layer material according to claim 1, characterized in that: The method specifically comprises the following steps: (1) Add raw material A (1.0 eq), raw material B (1.0-1.3 eq), potassium carbonate (2.0-4.0 eq) and a mixed solution of toluene, ethanol and water (V:V:V=3:1:1) to a reaction flask, protect with nitrogen, then add tetrakis(triphenylphosphine)palladium (0.01-0.03 eq), then heat to 75-95° C. and stir to react for 1-14 h; detect the reaction by thin layer chromatography to confirm the completion of the reaction, cool, add water and dichloromethane for extraction and separation, combine the organic phases and concentrate, and purify by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=1:3-1:10) to obtain intermediate 1; (2) Add intermediate 1 (1.0-1.3 eq), raw material C (1.0 eq), sodium tert-butoxide (2.0-4.0 eq) and toluene to a reaction flask, protect with nitrogen, then add tri(dibenzylideneacetone)dipalladium (0.01-0.05 eq) and tri-tert-butylphosphine (0.01-0.10 eq), then heat to 110-120° C. and stir to react for 4-24 h; detect the reaction by thin layer chromatography to confirm the completion of the reaction, cool, add water and dichloromethane for extraction and separation, combine the organic phases and concentrate, and purify by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=1:4-1:12) to obtain chemical formula I; The specific synthetic route is as follows: Wherein, R1, Ar1, Ar2 are as defined in the chemical formula I of claim 1, and X independently represents Where * is the attachment site.

8. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises the light-emitting auxiliary layer material according to any one of claims 1 to 6.

9. The use according to claim 8, characterized in that: The organic electroluminescent device comprises an organic layer; the organic layer contains the light-emitting auxiliary layer material.

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