Amino compound based on dimethyl fluorene-naphthalene substitution and organic electroluminescent device

Abstract

The invention discloses an amino compound based on dimethyl fluorene-naphthalene substitution and an organic electroluminescent device. The structure of the amino compound is shown as a formula (1). According to the invention, through connection of naphthyl, dimethyl fluorene with a deuterated benzene substituent group is combined with amido to form a core of the electroluminescent compound, and the core has good thermal stability, chemical stability and hole transport capability; the organic electroluminescent material prepared from the compound has good thermal stability and chemical stability, the stability of an electroluminescent device using the material can be effectively improved, the service life of the electroluminescent device using the material can be effectively prolonged, and meanwhile the luminescent efficiency of the device can be further improved due to the good hole transport performance of the organic electroluminescent material. The compound disclosed by the invention has high triplet state energy level and hole mobility, meanwhile, the compound disclosed by the invention has good solubility, and the problem that Mask is difficult to clean due to the solubility can be effectively avoided. # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to an amine compound based on dimethylfluorene-naphthalene substitution and an organic electroluminescent device. Background Art

[0002] Organic electroluminescence usually refers to an organic light-emitting diode (OLED) that uses electric current to drive an organic semiconductor film to emit light, thereby achieving the purpose of display.

[0003] The composition structure of an organic electroluminescent device includes a cathode, an anode, and an organic layer disposed between the cathode and the anode. The organic layer structure of the OLED device currently used in the industry is usually a multilayer structure, for example, including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and other film layers. For an OLED device including the above film layers, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When holes and electrons meet, excitons are formed, and when the excitons transition back to the ground state, light is emitted.

[0004] In existing OLED devices, the material types and matching forms of the organic layer are rich and diverse. In order to further improve the performance of OLED devices such as luminous efficiency and stability, the industry has been focusing on researching new materials for the organic layer. For example, the patent document with publication number KR1020210146820A discloses a new type of compound and an organic light-emitting device using the same. The compound is used as a material for the organic material layer of the organic light-emitting device to improve the performance of the organic light-emitting device. Summary of the invention

[0005] The technical purpose of the present invention is to develop new compounds based on existing materials so that they can be applied in the organic layer of electroluminescent devices, especially the hole transport layer, so that the devices have better performance.

[0006] In order to achieve the above technical objectives, the technical solution designed by the present invention is:

[0007] A dimethylfluorene-naphthalene substituted amino compound, characterized in that its structural formula is as shown in formula (1);

[0008]

[0009] In the formula (1):

[0010] L 1 and L 2 Each independently represents a direct bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C5-C30 heteroarylene group;

[0011] R 1 and R 2 Each independently represents a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C5-C30 heteroaryl group; m and n each independently represent 1 or 2;

[0012] X 1 , X 2 , X 3 , X 4 and X 5 Each independently represents hydrogen or deuterium, and X 1 , X 2 , X 3 , X 4 and X 5 At least one of them is deuterium;

[0013] L 1 and (R 1 ) m The group formed by the combination of 2 and (R 2 ) n The groups formed by the combination are the same or different as a whole;

[0014] L 1 , R 1 , L 2 and R 2 At least one of them is a naphthyl group, a dimethylfluorene group or a carbazolyl group, and the naphthyl group, the dimethylfluorene group or the carbazolyl group is substituted or unsubstituted, and L 1 With R 1 are not the naphthyl, dimethylfluorenyl or carbazolyl groups, L 2 With R 2 are not the naphthyl, dimethylfluorenyl or carbazolyl groups at the same time;

[0015] L 1 , R 1 , L 2 and R 2 The substituents in are each independently selected from any one or any combination of deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C6-C30 aryl, C6-C30 deuterated aryl, C7-C30 alkylaryl, C12-C30 phenylaryl, C5-C30 heteroaryl, C5-C30 deuterated heteroaryl, C6-C30 alkylheteroaryl, and C12-C30 phenylheteroaryl.

[0016] On the basis of the above scheme:

[0017] As a preferred embodiment, L 1 , R1 , L 2 and R 2 The substituents may be independently selected from any one or any combination of deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C6-C30 aryl, C6-C30 deuterated aryl, C5-C30 heteroaryl, and C5-C30 deuterated heteroaryl.

[0018] As a preferred embodiment, L 1 and L 2 is a direct bond or a substituted or unsubstituted phenyl group, R 1 and R 2 Each is independently a group consisting of any one or more substituted or unsubstituted groups selected from the following groups: phenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl; wherein the substituents are independently selected from any one or any combination of deuterium, fluorine, cyano, C1-C6 alkyl, C1-C6 deuterated alkyl, phenyl, deuterated phenyl, diphenyl, phenyl substituted with C1-C6 alkyl, naphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, carbazolyl substituted with phenyl.

[0019] As a preferred embodiment, L 1 and L 2 When it is a direct key, R 1 and R 2 Each independently is a group consisting of one or more combinations of the following groups:

[0020] Phenyl, phenyl substituted with methyl, phenyl substituted with methyl and phenyl, phenyl substituted with dibenzofuranyl, phenyl substituted with dibenzothienyl, dimethylfluorenyl, diphenyl, methyl-substituted biphenyl, terphenyl, dibenzofuranyl, dibenzofuranyl substituted with phenyl, naphthyl, phenyl substituted with naphthyl, naphthyl substituted with phenyl, dibenzothienyl, dibenzothienyl substituted with phenyl, carbazolyl, carbazolyl substituted with phenyl, or phenyl substituted with phenylcarbazolyl.

[0021] As a preferred embodiment, formula (1) is represented by the following formula I, formula II, formula III or formula IV:

[0022]

[0023] As a preferred embodiment, the structural formula of the amino compound is as follows:

[0024]

[0025] Wherein, D is deuterium.

[0026] As a preferred embodiment, formula (1) is represented by any one of the following formulas (1-1) to (1-12):

[0027]

[0028]

[0029] Among them, R 3 is hydrogen, deuterium or a C6-C20 aryl group, the C6-C20 aryl group is substituted or unsubstituted, wherein the substituent is selected from any one or any combination of deuterium, a C1-C6 alkyl group, and a phenyl group.

[0030] As a preferred embodiment, the amino compound is selected from one of the following compounds:

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043] An organic electroluminescent device, characterized in that it comprises a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode, wherein the organic layer contains the above-mentioned amino compound.

[0044] As a feasible embodiment, the organic layer includes a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, and at least one of the hole injection layer, the first hole transport layer, the second hole transport layer, the light-emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer contains the amino compound as described above, and further, at least the second hole transport layer contains the amino compound as described above.

[0045] The beneficial effects of the present invention are:

[0046] 1) The present invention combines dimethylfluorene with a deuterated benzene substituent and an amine group through the connection of a naphthalene substituent, and uses the combination as the core of an electroluminescent compound. The core has good thermal stability, chemical stability and hole transport ability. The organic electroluminescent material prepared using the compound has good thermal stability and chemical stability. The characteristics can effectively improve the stability and life of the electroluminescent device using the material. At the same time, the good hole transport performance can also further improve the luminous efficiency of the device.

[0047] 2) The compounds of the present invention effectively balance the injection and transmission of electrons and holes by finely adjusting the deuteration at special positions, broaden the recombination area of ​​excitons in the light-emitting layer, and thus improve the luminous efficiency of the device;

[0048] 3) The compound of the present invention has a high triplet energy level, which can effectively avoid the reverse transfer of energy from the light-emitting layer to the hole transport layer, thereby improving the efficiency of the device. In addition, the compound of the present invention has good solubility, which can effectively avoid the problem of difficult mask cleaning. BRIEF DESCRIPTION OF THE DRAWINGS

[0049] Figure 1 It is a schematic diagram of the structure of the organic electroluminescent device provided by the present invention;

[0050] Figure 2 It is the HPLC chart of the compound G2 of the present invention.

[0051] Figure 3 It is the DSC spectrum of compound G2 of the present invention.

[0052] Figure 4 It is the TGA spectrum of compound G2 of the present invention.

[0053] Figure 1 The reference numerals in the figures represent: 1-anode, 2-hole injection layer, 3-first hole transport layer, 4-second hole transport layer, 5-light-emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, 9-cathode. DETAILED DESCRIPTION

[0054] The following further illustrates and describes embodiments of various aspects of the present invention. It should be understood that the following description is not intended to limit the claims to the specific aspects described. On the contrary, it is intended to cover substitutions, modifications and equivalents that may be included within the scope defined by the appended claims.

[0055] In the "substituted" or "unsubstituted" used herein, the term "substituted" refers to the re-coordination of at least one hydrogen of a group with a substituent group such as deuterium, cyano, alkyl, aryl, heteroaryl, etc. "Aryl" herein refers to a group containing one or more aromatic rings, including but not limited to benzene, naphthalene, phenanthrene, fluorene, acenaphthene, etc. "Heteroaryl" herein refers to a heteroaryl group obtained by replacing one or more C in the structure of "aryl" with one or more heteroatoms (such as N, O or S), including but not limited to pyridine, pyrimidine, pyrrole, furan, thiophene, dibenzofuran, dibenzothiophene, carbazole, etc.

[0056] The terms C6-C30, C5-C30, C1-C10, C6-C20, etc. herein respectively indicate that the modified groups contain 6-30, 5-30, 1-10, 6-20 carbon atoms. If the corresponding groups can be substituted, the C6-C30, C5-C30, C1-C10, C6-C20 herein do not necessarily include the number of carbon atoms of the substituents. For example, "C7-C30 alkylaryl" means that the entire group contains 7-30 carbon atoms, and "phenyl substituted with C1-C6 alkyl" means that the alkyl group contains 1-6 carbon atoms.

[0057] The "deuterium" in the present invention refers to a stable isotope of hydrogen, also known as heavy hydrogen, and its element symbol is D.

[0058] If the specific conditions are not specified in the examples, the experiments were carried out under conventional conditions or conditions recommended by the manufacturer. If the manufacturers of the reagents or instruments are not specified, they are all conventional products that can be purchased commercially.

[0059] Embodiment 1:

[0060]

[0061] The synthesis method of compound G2 is as follows:

[0062] Step S1:

[0063] Process: Add CP8562-SM2 (60g, 0.37mol, 1eq) and ultra-dry THF (300ml) into a 1L three-necked flask, cool to below -65°C, add 1.6M n-butyllithium (243ml, 0.39mol, 1.05eq) dropwise, stir for 1h, add CP8562-SM1 (64g, 0.6mol, 0.35eq) in ultra-dry THF (250ml), add dropwise, stir at room temperature overnight.

[0064] Post-treatment: stop the reaction, add 400 ml of saturated ammonium chloride aqueous solution to quench, stir and separate the liquids, extract the aqueous phase with DCM, combine the organic phases, dry over anhydrous sodium sulfate, and concentrate the filtrate to dryness under reduced pressure. Use it directly in the next reaction without purification.

[0065] Step S2:

[0066] Process: CP8562-ZJ1 (theoretical 92.8 g, 0.35 mol, 1 eq), I2 (142 g, 0.56 mol, 1.6 eq), potassium carbonate (145 g, 1.05 mol, 3 eq) and tert-butanol (500 ml) were added to a 1 L three-necked flask. Under N2 protection, the temperature was raised to 90 °C and stirred for reaction for 20 h to 24 h.

[0067] Post-treatment: stop the reaction, add 500 ml of 50% sodium thiosulfate aqueous solution to quench, add EA (150 ml*3) to extract 3 times, combine the organic phases, wash with water twice, dry the organic phase over anhydrous sodium sulfate, filter, and concentrate the filtrate to dryness under reduced pressure to obtain 89.7 yellow oil, with a two-step yield of 97.3%.

[0068] Step S3:

[0069] Process: Add CP8562-SM3 (48.3 g, 0.2 mol, 1 eq) and ultra-dry THF (300 ml) into a 1 L three-necked flask, cool to below -65°C, add 1.6 M n-butyl lithium (131 ml, 0.21 mol, 1.05 eq) dropwise, stir at this temperature for 30 min, add a solution of CP8562-ZJ2 (50 g, 0.19 mol, 0.95 eq) in ultra-dry THF (100 ml), add dropwise, stir at room temperature overnight.

[0070] Post-treatment: stop the reaction, add 400 ml of saturated ammonium chloride aqueous solution to quench, stir and separate the liquids, extract the aqueous phase with DCM, combine the organic phases, dry over anhydrous sodium sulfate, and concentrate the filtrate to dryness under reduced pressure. Use it directly in the next reaction without purification.

[0071] Step S4:

[0072] Process: Add CP8562-ZJ3 (theoretical 79g, 0.19mol, 1eq) and DCM (500ml) to a 1L single-necked bottle, cool to below 0°C, add methanesulfonic acid (73g, 0.76mol, 4eq), and after the addition, move to room temperature and stir for 1-2h. Monitor CP8562-ZJ3 ≤2% by HPLC.

[0073] Post-treatment: stop the reaction, add 200 ml of ethanol, concentrate under low temperature and reduced pressure to remove most of the DCM until there is almost no droplet, filter, rinse the filter cake with ethanol 3 to 4 times, and dry the filter cake at 85°C to obtain 55.3 g of gray solid, with a two-step yield of 71.3%.

[0074] Step S5:

[0075] Process: CP8562-ZJ4 (50g, 0.123mol, 1eq), CP8562-SM4 (44.3g, 0.123mol, 1eq), sodium tert-butoxide (14.2g, 0.148mol, 1.2eq), XPhos (2.35g, 4.92mmol, 0.04eq) and toluene (500ml) were added into a 1L three-necked flask. Palladium acetate (0.55g, 2.46mmol, 0.02eq) was added under N2 protection. After the addition was completed, the temperature was raised to 100℃ and the reaction was stirred. HPLC monitored CP8562-ZJ4≤1%.

[0076] Post-treatment: stop the reaction, filter through silica gel while hot, concentrate the filtrate to dryness under reduced pressure, add 150 ml of toluene and heat to dissolve, then add 300 ml of ethanol, cool to room temperature for crystallization, filter, recrystallize the filter cake with toluene (150 ml*5) 5 times, dry the filter cake at 85°C to obtain 46 g of off-white solid with HPLC purity of 99.9825% and a yield of 51%.

[0077] Compounds G1, G3, G4, G9, G12, G14, G33, G37, G45, G49, G56, G59, G84, G88, G100, G113, G141, G161, G162, G166, G189, G214, G219, G223, G231 and G235 obtained by a similar preparation method are shown in Table 1 below:

[0078] Table 1

[0079]

[0080]

[0081]

[0082]

[0083]

[0084] The synthesis and identification results of compounds G1, G2, G3, G4, G9, G12, G14, G33, G37, G45, G49, G56, G59, G84, G88, G100, G113, G141, G161, G162, G166, G189, G214, G219, G223, G231, and G235 are shown in Table 2 below:

[0085] Table 2

[0086]

[0087] Material property test:

[0088] The test results of thermal weight loss temperature Td and melting point temperature Tm of compounds G1, G2, G3, G4, G9, G12, G14, G33, G37, G45, G49, G56, G59, G84, G88, G100, G113, G141, G161, G162, G166, G189, G214, G219, G223, G231 and G235 are shown in Table 3 below:

[0089] Table 3

[0090] Test Materials Td / ℃ Tm / ℃ Test Materials Td / ℃ Tm / ℃ G1 416.53℃ 285.25℃ G88 425.70℃ 297.46℃ G2 414.48℃ 287.25℃ G100 419.68℃ 293.75℃ G3 420.86℃ 275.67℃ G113 416.88℃ 298.60℃ G4 418.86℃ 265.08℃ G141 424.63℃ 292.75℃ G9 412.32℃ 280.46℃ G161 428.76℃ 289.26℃ G12 426.76℃ 297.49℃ G162 417.56℃ 295.67℃ G14 422.49℃ 270.32℃ G166 420.76℃ 291.55℃ G33 405.57℃ 295.66℃ G189 430.68℃ 295.47℃ G37 408.69℃ 298.70℃ G214 405.86℃ 285.67℃ G45 431.55℃ 300.45℃ G219 420.05℃ 279.55℃ G49 428.76℃ 286.23℃ G223 416.59℃ 284.35℃ G56 424.68℃ 283.26℃ G231 417.10℃ 285.14℃ G69 414.46℃ 293.36℃ G235 420.55℃ 291.25℃ G84 409.58℃ 285.54℃

[0091] Note: The thermal weight loss temperature Td is the temperature at which the weight loss is 5% in a nitrogen atmosphere, and is measured on a TGAN-1000 thermogravimetric analyzer with a nitrogen flow rate of 10 mL / min. The melting point temperature Tm is measured by differential scanning calorimetry (DSC, Shinco DSC N-650) with a heating rate of 10°C / min.

[0092] It can be seen from the above data that the compound synthesized in the present invention has excellent thermal stability and can meet the requirements for use of organic electroluminescent materials.

[0093] Device performance test:

[0094] Application Example 1:

[0095] ITO was used as the reflective layer anode substrate material, and its surface was treated with water, acetone, and N2 plasma in sequence;

[0096] On top of the ITO anode substrate, 10 nm of HT-1 doped with 2% by mass of NDP-9 was deposited to form a hole injection layer (HIL);

[0097] 100 nm of HT-1 was evaporated on the hole injection layer (HIL) to form the first hole transport layer (HTL);

[0098] Vacuum-evaporate the compound G2 synthesized in Example 1 on the first hole transport layer (HTL) to form a second hole transport layer (GPL) with a thickness of 30 nm;

[0099] Compounds T1 and T2 were co-evaporated at a mass ratio of 5:5 as green light host materials, and GD-1 was evaporated as a doping material (the amount of GD-1 was 8% of the total mass of T1 and T2) on the second hole transport layer (GPL) to form a light-emitting layer with a thickness of 30 nm;

[0100] HB-1 was evaporated onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0101] ET-1 and LiQ were co-evaporated onto the hole blocking layer (HBL) in a mass ratio of 5:5 to obtain an electron transport layer (ETL) with a thickness of 30 nm;

[0102] Magnesium (Mg) and silver (Ag) were mixed and evaporated on the electron transport layer (ETL) in a mass ratio of 9:1 to form an electron injection layer (EIL) with a thickness of 50 nm;

[0103] Thereafter, silver (Ag) is evaporated onto the electron injection layer to form a cathode with a thickness of 100 nm, and a DNTPD with a thickness of 50 nm is deposited on the cathode sealing layer. In addition, the cathode surface is sealed with a UV curable adhesive and a sealing film (seal cap) containing a dehumidifier to protect the organic electroluminescent device from being affected by oxygen or moisture in the atmosphere. Thus, an organic electroluminescent device is prepared.

[0104] In the organic electroluminescent device, the second hole transport layer is responsible for transporting holes and blocking electrons, and at the same time blocks the energy from being transferred back from the light-emitting layer to the hole transport layer.

[0105] The structural formula of the compound used in the above process is as follows:

[0106]

[0107] Application Example 2-27:

[0108] Compounds G1, G3, G4, G9, G12, G14, G33, G37, G45, G49, G56, G59, G84, G88, G100, G113, G141, G161, G162, G166, G189, G214, G219, G223, G231 and G235 were respectively used as the second hole transport layer of the green light device for vapor deposition, and the preparation of other organic layers was consistent with that in Application Example 1, and organic electroluminescent devices of Application Examples 2-27 were prepared accordingly.

[0109] Comparative Examples 1-8:

[0110]

[0111] The reference compounds J1-8 were respectively used as the second hole transport layer of the green light device for evaporation, and the preparation of other organic layers was consistent with that of Application Example 1, thereby preparing the organic electroluminescent devices of Reference Examples 1-8.

[0112] At a current density of 10 mA / cm 2 The characteristics of the organic electroluminescent device manufactured in the application example and the organic electroluminescent device manufactured in the control example were tested under the conditions of , and the test results are shown in Table 4 below:

[0113] Table 4

[0114]

[0115]

[0116] As can be seen from the above table, when the compounds of the present invention are applied to organic electroluminescent devices, compared with compounds that are not deuterated at special substituent positions, at the same current density, the luminous efficiency is greatly improved, the starting voltage of the device is reduced, and the power consumption of the device is relatively reduced.

[0117] The organic electroluminescent devices prepared by using the reference compounds J1-J8 and the example compounds G1-G4, G9, G12, G33, G56, G100, G162, G189, G214 and G231 were respectively subjected to luminescence lifetime tests, and the luminescence lifetime T97% data (the time for the luminescence brightness to decrease to 97% of the initial brightness) were obtained. The test results are shown in Table 5 (with the lifetime data of the J1 compound as a reference):

[0118] Table 5

[0119]

[0120]

[0121] It can be seen from the above table that when the compound of the present invention is applied to an organic electroluminescent device, under the same current density and other parameter conditions, the service life of the device is greatly improved, and it has broad application prospects.

[0122] In summary, compared with the reference compound without deuteration, the deuteration of the substituents at the special positions of the example compounds further improves the stability of the device, as well as the luminous efficiency and life of the device. At the same time, according to other tests, the compounds of the present invention have good solubility and are not prone to the problem of difficult mask cleaning due to solubility in the production line.

[0123] It should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention rather than to limit it. Although the present invention has been described in detail with reference to the preferred embodiments, those skilled in the art should understand that the technical solutions of the present invention may be modified or replaced by equivalents without departing from the spirit and scope of the technical solutions of the present invention, which should all be included in the scope of the claims of the present invention.

Claims

1. A dimethylfluorene-naphthalene substituted amino compound, characterized in that: Its structural formula is shown in formula (1); In the formula (1): L 1 and L 2 Each independently represents a direct bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C5-C30 heteroarylene group; R 1 and R 2 Each independently represents a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C5-C30 heteroaryl group; m and n each independently represent 1 or 2; X 1 , X 2 , X 3 , X 4 and X 5 Each independently represents hydrogen or deuterium, and X 1 , X 2 , X 3 , X 4 and X 5 At least one of them is deuterium; L 1 and (R 1 ) m The group formed by the combination of 2 and (R 2 ) n The groups formed by the combination are the same or different as a whole; L 1 , R 1 , L 2 and R 2 At least one of them is a naphthyl group, a dimethylfluorene group or a carbazolyl group, and the naphthyl group, the dimethylfluorene group or the carbazolyl group is substituted or unsubstituted, and L 1 With R 1 are not the naphthyl, dimethylfluorenyl or carbazolyl groups, L 2 With R 2 are not the naphthyl, dimethylfluorenyl or carbazolyl groups at the same time; L 1 , R 1 , L 2 and R 2 The substituents in are each independently selected from any one or any combination of deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C6-C30 aryl, C6-C30 deuterated aryl, C7-C30 alkylaryl, C12-C30 phenylaryl, C5-C30 heteroaryl, C5-C30 deuterated heteroaryl, C6-C30 alkylheteroaryl, and C12-C30 phenylheteroaryl.

2. The dimethylfluorene-naphthalene substituted amino compound according to claim 1, characterized in that: The L 1 and L 2 is a direct bond or a substituted or unsubstituted phenyl group, R 1 and R 2 Each is independently a group consisting of any one or more substituted or unsubstituted groups selected from the following groups: phenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl; wherein the substituents are independently selected from any one or any combination of deuterium, fluorine, cyano, C1-C6 alkyl, C1-C6 deuterated alkyl, phenyl, deuterated phenyl, diphenyl, phenyl substituted with C1-C6 alkyl, naphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, carbazolyl substituted with phenyl.

3. The dimethylfluorene-naphthalene substituted amino compound according to claim 1, characterized in that: The L 1 and L 2 is a direct key, R 1 and R 2 Each independently is a group consisting of one or more combinations of the following groups: Phenyl, phenyl substituted with methyl, phenyl substituted with methyl and phenyl, phenyl substituted with dibenzofuranyl, phenyl substituted with dibenzothienyl, dimethylfluorenyl, diphenyl, methyl-substituted biphenyl, terphenyl, dibenzofuranyl, dibenzofuranyl substituted with phenyl, naphthyl, phenyl substituted with naphthyl, naphthyl substituted with phenyl, dibenzothienyl, dibenzothienyl substituted with phenyl, carbazolyl, carbazolyl substituted with phenyl, or phenyl substituted with phenylcarbazolyl.

4. The dimethylfluorene-naphthalene substituted amino compound according to claim 1, characterized in that: Formula (1) is represented by the following formula I, formula II, formula III or formula IV:

5. The dimethylfluorene-naphthalene substituted amino compound according to claim 1, characterized in that: The structural formula of the amino compound is as follows:

6. The dimethylfluorene-naphthalene substituted amino compound according to claim 1, 2 or 3, characterized in that: Formula (1) is represented by any one of the following formulas (1-1) to (1-12): Among them, R 3 It is hydrogen, deuterium or a substituted or unsubstituted C6-C20 aryl group, wherein the substituent is selected from any one or any combination of deuterium, a C1-C6 alkyl group and a phenyl group.

7. The dimethylfluorene-naphthalene substituted amino compound according to claim 1, characterized in that: The amino compound is any one of the following compounds:

8. An organic electroluminescent device, characterized in that: The invention comprises a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode, wherein the organic layer contains the amino compound according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that: The organic layer includes a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, and at least one of the hole injection layer, the first hole transport layer, the second hole transport layer, the light-emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer contains an amino compound as described in any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, characterized in that: The organic layer comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, wherein the second hole transport layer contains the amino compound according to any one of claims 1 to 7.

Images