Amino compound and organic light-emitting device

Abstract

The invention relates to a novel organic electroluminescent material, which ingeniously combines deuterated modification and alkyl substitution through the elaborate design of the molecular structure, and realizes the synergistic improvement of various excellent properties. By introducing deuterium, the chemical stability and thermal stability of the material and a doped material are improved, the luminous efficiency and stability of a device are further greatly improved, and energy loss caused by vibration relaxation can be reduced by performing deuteration on phenyl on a 9, 9-diphenylfluorene unit, so that the efficiency of the device is improved. Alkyl substitution can optimize the energy level structure of the material and promote carrier injection and transmission, thereby improving the current efficiency of the device.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, specifically to an amine compound and an organic light-emitting device. Background Technology

[0002] OLEDs are current-driven organic light-emitting devices that emit light through the injection and recombination of charge carriers. The luminous intensity is directly proportional to the injected current. Under the influence of an electric field, holes generated at the anode and electrons at the cathode move and are injected into the hole transport layer and electron transport layer, respectively, migrating to the emissive layer. When these two electrons meet in the emissive layer, they generate excitons, which excite the light-emitting molecules to ultimately produce visible light.

[0003] In organic light-emitting devices (OLEDs), the biggest challenges are lifetime and efficiency, and these issues must be addressed as display areas increase. Efficiency, lifetime, and driving voltage are interrelated; as efficiency improves, the driving voltage relatively decreases, leading to an increase in lifetime. However, efficiency cannot be maximized simply by improving the organic material layers. This is because long lifetime and high efficiency can be achieved simultaneously when the energy levels and T1 values ​​between each organic layer are optimally combined with the inherent properties of the material (mobility, interface properties, etc.).

[0004] In addition, in order to solve the light emission problem of the hole transport layer in recent organic electroluminescent devices, a light emission auxiliary layer must exist between the hole transport layer and the light emission layer. Depending on each light emission layer (R, G, B), it is time to develop different light emission auxiliary layers.

[0005] In terms of the actual needs of the current organic electroluminescent industry, the development of organic electroluminescent materials is far from sufficient and lags far behind the requirements of panel manufacturers. Moreover, the research progress of domestic companies is also far behind that of American, Japanese and Korean companies. Therefore, developing organic electroluminescent materials that provide more options is the top priority for domestic panel manufacturers. Summary of the Invention

[0006] The purpose of this invention is to address the above-mentioned technical problems by providing an amine compound and an organic electroluminescent device.

[0007] The objective of this invention can be achieved through the following measures:

[0008] An amino compound with the structure shown in Formula 1:

[0009]

[0010] in,

[0011] L1 and L2 are each independently a single bond, a substituted or unsubstituted C6-C20 aryl group, and the substituent is selected from one or more of deuterium, fluorine, cyano, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl.

[0012] Ar1 and Ar2 are substituted or unsubstituted groups of the following: C6-C30 aryl or C5-C30 heteroaryl, wherein the substituent is selected from one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl;

[0013] R is a deuterium, fluorine, cyano, or a deuterated or undeuterated group of the following: one of C1-C10 alkyl groups or C4-C8 cycloalkyl groups;

[0014] A1-A5 are each independently hydrogen or deuterium, and at least one of A1-A5 is deuterium.

[0015] More preferably, Ar1 and Ar2 are substituted or unsubstituted groups of the following: C6-C18 aryl or C5-C24 heteroaryl, wherein the substituent is selected from one or more of deuterium, fluorine, cyano, C1-C6 alkyl, C1-C6 deuterated alkyl, C6-C18 aryl, C6-C18 deuterated aryl, and C5-C24 heteroaryl;

[0016] L1 and L2 are independently single-bonded, substituted or unsubstituted phenyl, naphthyl, or biphenyl groups, respectively, and their substituents are selected from one or more of deuterium, fluorine, cyano, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl.

[0017] R is a deuterated or undeuterated group of the following: one of C1-C10 alkyl groups or C5-C8 cycloalkyl groups.

[0018] Preferably, the structural formula of the compound of the present invention is shown in Formula 2 below:

[0019]

[0020] in,

[0021] Ar1 and Ar2 are substituted or unsubstituted groups of the following: phenyl, biphenyl, naphthyl, anthracene, dibenzofuranyl, dibenzothiophene, fluorenyl, phenanthrene, benzophenanthrenefuranyl, wherein the substituent is selected from one or more of deuterium, fluorine, cyano, methyl, C6-C12 aryl, C6-C12 deuterated aryl, and C5-C20 heteroaryl;

[0022] L1 and L2 are independently single bonds or phenyl, naphthyl, and biphenyl groups, respectively;

[0023] R is a deuterated or undeuterated group of the following: one of C1-C6 alkyl groups or C5-C8 cycloalkyl groups;

[0024] A1-A5 are each independently hydrogen or deuterium, with 3-5 of A1-A5 being deuterium.

[0025] More preferably, Ar1 and Ar2 are substituted or unsubstituted groups of the following: phenyl, biphenyl, naphthyl, anthracene, dibenzofuranyl, dibenzothiophene, fluorenyl, phenanthrene, benzophenanthrenefuranyl, wherein the substituent is selected from one or more of deuterium, fluorine, cyano, methyl, C6-C12 aryl, C6-C12 deuterated aryl, and C5-C20 heteroaryl;

[0026] L1 and L2 are independently single bonds, phenyl, and biphenyl, respectively.

[0027] Preferably, Ar1 is 9,9-dimethylfluorene;

[0028] Ar2 can be a substituted or unsubstituted group of the following: phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, wherein the substituent is selected from one or more of deuterium, methyl, and phenyl;

[0029] L1 and L2 are independently single bonds, phenyl, and biphenyl, respectively;

[0030] R is a deuterated or undeuterated group of the following: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, or cyclohexyl.

[0031] In a preferred embodiment, the compound of the present invention may be any one of the following compounds:

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040] An organic electroluminescent device includes 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 aforementioned organic electroluminescent compound.

[0041] Furthermore, the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; at least one of the hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, and electron injection layer contains the aforementioned organic electroluminescent compound.

[0042] Furthermore, the electron blocking layer contains the aforementioned organic electroluminescent compound.

[0043] The beneficial effects of this invention are:

[0044] This invention relates to a novel organic electroluminescent material that, through careful design of the molecular structure, cleverly combines deuteration modification and alkyl substitution to achieve a synergistic enhancement of multiple superior properties.

[0045] First, the introduction of deuterium improves the chemical and thermal stability of this type of material and the doped material, thereby significantly improving the luminous efficiency and stability of the device.

[0046] Second, deuteration of the phenyl group on the 9,9-diphenylfluorene unit can reduce energy loss caused by vibrational relaxation, thereby improving device efficiency.

[0047] Third, alkyl substitution can optimize the energy level structure of materials, promote carrier injection and transport, and thus improve the current efficiency of devices. Attached Figure Description

[0048] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device provided by the present invention;

[0049] The numbers in the diagram represent: 1-anode, 2-hole injection layer, 3-hole transport layer, 4-second hole transport layer, 5-light-emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, and 9-cathode.

[0050] Figure 2 This is the HPLC chromatogram of compound 37 of the present invention.

[0051] Figure 3 The TGA spectrum of compound 37 of this invention is shown below. Figure 4 It can be seen that the thermal weight loss temperature Td of compound 1 is 392.18℃.

[0052] Figure 4 This is the NMR spectrum of compound 37 of the present invention. Detailed Implementation

[0053] Embodiments of various aspects are further illustrated and described below. It should be understood that the description herein is not intended to limit the claims to the specific aspects described. Rather, it is intended to cover substitutions, modifications, and equivalents that may be included within the spirit and scope of this disclosure as defined by the appended claims.

[0054] As used herein, in the terms “deuterated” and “undeuterated,” the term “deuterated” means that at least one hydrogen in the group is recoordinated with deuterium. The term “undeuterated” means that none of the hydrogens in the group are recoordinated with deuterium.

[0055] In this document, "aromatic group," "aryl," or "aromatic group" refers to a group containing one or more aromatic rings, including but not limited to benzene, naphthalene, phenanthrene, fluorene, acenaphthene, pyridine, pyrrole, furan, and thiophene. In C5-C40 aromatic groups, C5-C40 means that the group contains 5-40 carbon atoms. Aromatic groups can be classified as monocyclic aryl and polycyclic aryl. Specific aromatic groups in this invention include, but are not limited to, phenyl, biphenyl, terphenyl, anthracene, naphthyl, phenanthrene, fluorene, dibenzofuranyl, dibenzothiophene, 9,9-spirodifluorenyl, 9,9-dimethylfluorenyl, or 9,9-diphenylfluorenyl. Aromatic groups can be substituted or unsubstituted.

[0056] As used herein, "cycloalkyl" refers to a monocyclic or fused ring group consisting entirely of carbon atoms (a "fused" ring means that each ring in the system shares an adjacent pair of carbon atoms with other rings in the system), wherein one or more rings are saturated alicyclic rings, generally having 3-20 carbon atoms, preferably 3-12 carbon atoms, and more preferably 3-10 carbon atoms. Cycloalkyl groups can be classified into monocyclic alkyl groups having only one ring and fused alkyl groups having multiple rings. Examples of monocyclic alkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, and cycloheptane. Cycloalkyl groups can be substituted or unsubstituted.

[0057] As used herein, "cycloalkenyl" refers to a monocyclic or fused ring group consisting entirely of carbon (a "fused" ring means that each ring in the system shares a pair of adjacent carbon atoms with other rings in the system), wherein one or more rings do not have a fully connected π-electron system and contain at least one alkenyl group, which generally has 3-20 carbon atoms, preferably 3-12 carbon atoms, more preferably 3-10 carbon atoms. Examples of cycloalkenyl groups include, but are not limited to, cyclopentene, cyclohexene, cyclohexadiene, and cycloheptanetriene. The cycloalkenyl group can be substituted or unsubstituted.

[0058] In this article, "deuterated aromatic group" refers to an aromatic group in which one or more hydrogen atoms are replaced by deuterium.

[0059] In this article, "deuterated phenyl" refers to a group in which one or more hydrogen atoms in a phenyl group are replaced by deuterium.

[0060] In this article, "heteroaryl" refers to a heteroaryl group obtained by replacing one or more C atoms in the structure of "aryl" with one or more heteroatoms (such as N, O or S).

[0061] Unless otherwise specified in the examples, the procedures should be performed under standard conditions or conditions recommended by the manufacturer. Reagents or instruments whose manufacturers are not specified are all commercially available products.

[0062] Example 1

[0063]

[0064] Compound 25 was prepared according to the following method:

[0065] Step 1:

[0066]

[0067] In a 2L three-necked flask, bromide 2-a (49.4 g, 0.2 mol, 1 eq), 2-b (41.8 g, 0.2 mol, 1 eq), sodium tert-butoxide (23.0 g, 0.24 mol, 1.2 eq), tri-tert-butylphosphine (16.2 mL, 8 mmol, 0.04 eq), and toluene (800 mL) were added. Under N2 protection, tris(2-benzylacetone)palladium (3.66 g, 4 mmol, 0.02 eq) was added. After the addition was complete, the mixture was heated to 100 °C and stirred. HPLC monitoring showed that 2-a ≤ 1%. The reaction was stopped, and the mixture was filtered through silica gel while hot. The filtrate was concentrated to dryness under reduced pressure, and 400 mL of ethanol was added. The mixture was stirred at 65 °C for 2 h, and a solid precipitated. The mixture was cooled to room temperature to allow crystals to crystallize. The crystals were filtered, and the filter cake was dried at 85 °C with forced air to give 61.2 g of off-white solid 2-c, with a yield of 81.6%.

[0068] Step 2:

[0069]

[0070] In a 1L three-necked flask, 2-d (37.5g, 0.1mol, 1eq), 2-c (43.2g, 0.1mol, 1eq), sodium tert-butoxide (11.5g, 0.12mol, 1.2eq), tritert-tert-butylphosphine (8.1ml, 4mmol, 0.04eq), and toluene (400ml) were added. Under N2 protection, tris(dibenzylacetone)palladium (1.83g, 2mmol, 0.02eq) was added. After the addition was complete, the mixture was heated to 100℃ and stirred. The reaction was monitored by HPLC, and 1-i ≤ 1%. The reaction was stopped, and the mixture was filtered through silica gel while hot. The filtrate was concentrated to dryness under reduced pressure. 100 ml of toluene was added and heated to dissolve the solid. 200 ml of ethanol was added, and the mixture was cooled to room temperature to allow crystals to form. The crystals were filtered, and the filter cake was recrystallized five times with toluene (150 ml * 5). The filter cake was dried at 85 °C with a forced air drying process to obtain 32.1 g of off-white solid 25, with an HPLC purity of 99.9627% and a yield of 44.2%.

[0071] Compounds 2, 5, 7, 10, 16, 22, 32, 40, 96, 102, 157, 160, 164, 167, 171, 177, 179, 186, 189, and 206 were obtained using a similar method. See Table 1 below for details.

[0072] Table 1

[0073]

[0074]

[0075]

[0076]

[0077]

[0078] Example 22

[0079]

[0080] Compound 37 was prepared according to the following method.

[0081] Step 1:

[0082]

[0083] Compound 1-a (101.74 g, 0.628 mol, 1 eq) and ultradry THF (500 ml) were added to a 2 L three-necked flask. The temperature was lowered to below -65 °C, and n-butyllithium (412 ml, 0.66 mol, 1.05 eq) was added dropwise. After the addition was complete, the mixture was kept at this temperature and stirred for 1 h. Then, 1-b (118.8 g, 0.6 mol, 0.95 eq) of ultradry THF (100 ml) solution was added dropwise. After the addition was complete, the mixture was stirred at room temperature overnight. The reaction was stopped, and 800 ml of saturated ammonium chloride aqueous solution was added to quench the reaction. The mixture was stirred and separated. The aqueous phase was extracted with DCM, and the organic phases were combined and dried over anhydrous sodium sulfate. The filtrate was concentrated to dryness under reduced pressure to obtain intermediate 1-c, which was used directly in the next reaction without purification.

[0084] In a 2L three-necked flask, 1-c (theoretical 169.3g, 0.6mol, 1eq), I2 (242g, 0.96mol, 1.6eq), potassium carbonate (248g, 1.8mol, 3eq), and tert-butanol (600ml) were added. Under N2 protection, the mixture was heated to 90℃ and stirred for 20-24 hours. The reaction was stopped, quenched with 800ml of 50% sodium thiosulfate aqueous solution, and extracted three times with EA (300ml*3). The organic phases were combined, washed twice with water, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to give 165g of a yellow oily substance 1-d, with a two-step yield of 98.2%.

[0085] Step 2:

[0086]

[0087] Add 1-d (144.55 g, 0.62 mol, 1 eq) and ultradry THF (500 ml) to a 2 L three-necked flask, cool to below -65 °C, and add n-butyllithium (407 ml, 0.651 mol, 1.05 eq) dropwise. After the addition is complete, keep warm and stir for 30 min. Then add 1-e (165 g, 0.589 mol, 0.95 eq) of ultradry THF (100 ml) dropwise. After the addition is complete, stir and react at room temperature overnight. Stop the reaction, quench with 800 ml of saturated ammonium chloride aqueous solution, stir and separate the layers. Extract the aqueous phase with DCM, combine the organic phases, dry with anhydrous sodium sulfate, and concentrate the filtrate to dryness under reduced pressure to obtain 1-f, which is used directly in the next reaction without purification.

[0088] In a 2L single-necked flask, 1-f (theoretical 255.8 g, 0.589 mol, 1 eq) and DCM (800 ml) were added. The mixture was cooled to below 0°C, and methanesulfonic acid (226 g, 2.356 mol, 4 eq) was added. After the addition was complete, the mixture was moved to room temperature and stirred for 1–2 h. HPLC monitoring showed that 1-f ≤ 5%. The reaction was stopped, and 200 ml of ethanol was added. The mixture was concentrated under reduced pressure at low temperature to remove most of the DCM until almost no droplets remained. The mixture was filtered, and the filter cake was washed with ethanol 3–4 times. The filter cake was dried at 85°C with forced air to obtain 173 g of gray solid 1-g. The two-step yield was 70.1%.

[0089] 1 g (95 g, 0.228 mol, 1 eq), sodium tert-butoxide (22 g, 0.228 mol, 1 eq), deuterated dimethyl sulfoxide (192 g, 2.28 mol, 10 eq), and THF (200 ml) were added to a 2 L three-necked flask. The mixture was heated to 80 °C and stirred for 48 h. The reaction was stopped, and 1000 ml of water was added to cool and stir for 1 h to precipitate crystals. A large amount of solid precipitated. The solid was filtered, and the filter cake was dissolved in 1 L of DCM. 100 g of 100-200 mesh silica gel was added to prepare silica gel precipitate. 800 g of 100-200 mesh silica gel was packed into a column for column chromatography. The PE / DCM ratio was 20 / 1 to 10 / 1 to 5 / 1 to 3 / 1. The product was collected, concentrated under reduced pressure until nearly dry, filtered, and the filter cake was dried at 85 °C with forced air to obtain 85 g of off-white solid for 1 h, with a yield of 85.3%.

[0090] Step 3

[0091]

[0092] The synthesis steps were as described in Example 1. The HPLC purity of compound 37 was 99.9582%, and the yield was 52.3%.

[0093] Compounds 8, 13, 14, 29, 30, 35, 36, 38, 43, 77, 83, 99, 109, and 115 were obtained using a similar method, as detailed in Table 2 below.

[0094] Table 2

[0095]

[0096]

[0097]

[0098]

[0099] Example 37

[0100]

[0101] Compound 75 was prepared according to the following method.

[0102] Step 1:

[0103]

[0104] In a 1L three-necked flask, 3-a (62.2 g, 0.2 mol, 1 eq), 3-b (26.9 g, 0.21 mol, 1 eq), potassium carbonate (55.3 g, 0.4 mol, 2 eq), Pd(PPd3)4 (4.62 g, 4 mmol, 0.02 eq), and toluene / ethanol / water (600 ml + 300 ml + 180 ml) were added. The mixture was heated to reflux under N2 protection, and HPLC monitoring was performed until 3-a ≤ 0.5%. The reaction was stopped, water was added, and the mixture was separated by stirring. The aqueous phase was extracted with DCM, the organic phases were combined, and the mixture was filtered through silica gel. The filtrate was concentrated to dryness under reduced pressure, and 150 ml of PE was added. A solid precipitated, and the mixture was stirred and filtered. The filter cake was dried at 85°C with forced air to obtain 40.3 g of off-white solid 3-c, with a yield of 75.5%.

[0105] Step 2:

[0106]

[0107] The synthesis steps were as described in Example 1. The HPLC purity of compound 75 was 99.9681%, and the yield was 35.9%.

[0108] Compounds 46, 51, 52, 54, 59, 67, 70, 128, 131, 134, 141, 144, 150, and 198 were obtained using a similar method. See Table 3 below for details.

[0109] Table 3

[0110]

[0111]

[0112]

[0113]

[0114] Example 52

[0115]

[0116] Compound 208 was prepared according to the following method.

[0117] Step 1:

[0118]

[0119] In a 1L single-necked flask, bromobenzene 4-a (50 g, 0.318 mol, 1 eq), silver carbonate (17.5 g, 0.06 mol, 0.2 eq), potassium carbonate (44 g, 0.318 mol, 1 eq), diphenylcyclohexylphosphine (42.7 g, 0.159 mol, 0.5 eq), heavy water (127.2 g, 6.36 mol, 20 eq), and toluene (25 mL) were added. The mixture was heated to T = 95 °C and refluxed for 48 h. After cooling, the mixture was filtered, and the filtrate was extracted with water and DCM by stirring. The aqueous phase was extracted twice with DCM. The organic phases were combined, and 85 g of 100-200 mesh silica gel was added to prepare silica gel precipitate. 800 g of 100-200 mesh silica gel was packed into a column for column chromatography. The product spot was collected and concentrated to dryness under reduced pressure to obtain 41.3 g of colorless oil 4-b, with a yield of 81.1%.

[0120] Step 2:

[0121]

[0122] The synthesis steps were as described in Example 2. The HPLC purity of compound 208 was 99.9725%, and the yield was 49.2%.

[0123] The results of the synthesis and identification of the compounds prepared in Tables 1-3 above are shown in Table 4 below:

[0124] Table 4

[0125]

[0126]

[0127] Basic performance tests were conducted on the above materials, including thermogravimetric temperature Td and melting point Tm. The test results are shown in Table 5 below.

[0128] Note: The thermogravimetric temperature Td is the temperature at which the mass loss is 5% in a nitrogen atmosphere, measured on a TGA N-1000 thermogravimetric analyzer at a nitrogen flow rate of 10 mL / min. Tg (glass transition temperature) is measured by differential scanning calorimetry (DSC, Shinco DSC N-650) at a heating rate of 10 °C / min.

[0129] Table 5

[0130]

[0131]

[0132] Based on the above data, it can be seen that the compounds synthesized in this invention have excellent thermal stability, indicating that compounds conforming to the general structural formula of this invention all have excellent thermal stability and can meet the requirements for use in organic electroluminescent materials.

[0133] Device performance testing:

[0134] Application Example 1:

[0135] ITO was used as the anode substrate material for the reflective layer, and its surface was treated sequentially with water, acetone, and N2 ions.

[0136] A hole injection layer (HIL) is formed by depositing 10 nm of HT-1 doped with 2% NDP-9 by mass on top of the ITO anode substrate.

[0137] A first hole transport layer (HTL) is formed by depositing 100 nm of HT-1 above the hole injection layer (HIL);

[0138] Compound 37 of the present invention was vacuum-deposited over the first hole transport layer (HTL) to form a second hole transport layer (GPL) with a thickness of 30 nm.

[0139] Compounds G1 and G2 were co-deposited as green light host materials in a 5:5 mass ratio, and GD-1 was deposited as a dopant material (GD-1 amount was 8% of the total mass of G1 and G2) on the second hole transport layer (GPL) to form a light-emitting layer with a thickness of 30 nm.

[0140] HB-1 was deposited onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0141] ET-1 and LiQ were co-deposited onto the hole blocking layer (HBL) at a mass ratio of 5:5 to obtain an electron transport layer (ETL) with a thickness of 30 nm.

[0142] Magnesium (Mg) and silver (Ag) are mixed in a mass ratio of 9:1 and vapor-deposited onto the electron transport layer (ETL) to form an electron injection layer (EIL) with a thickness of 50 nm.

[0143] Subsequently, silver (Ag) is vapor-deposited onto the electron injection layer to form a cathode with a thickness of 100 nm. A 50 nm thick DNTPD is then deposited on the cathode sealing layer. Furthermore, the cathode surface is sealed with a UV-curable adhesive and a sealing cap containing a desiccant to protect the organic electroluminescent device from the influence of atmospheric oxygen or moisture. Thus, an organic electroluminescent device is prepared.

[0144]

[0145] Application Example 2-52

[0146] Compounds 2, 4, 7, 8, 10, 13, 14, 16, 22, 25, 29, 30, 32, 35, 36, 38, 41, 43, 46, 51, 52, 54, 59, 67, 70, 75, 77, 83, 96, 99, 102, 109, 115, 128, 131, 134, 141, 144, 150, 157, 160, 164, 167, 171, 177, 179, 186, 189, 198, 206, and 208 from Examples 2-52 of the present invention were used as hole transport materials, with the other parts being the same as in Application Example 1. Based on this, organic electroluminescent devices of Application Examples 2-52 were fabricated.

[0147] Compare with Examples 1-3:

[0148] The difference from Application Example 1 is that compounds D1 and D2 in CN114975839A and compound D3 in KR1020230030513A are used as hole transport materials, respectively; otherwise, they are the same as in Application Example 1.

[0149] The characteristics of the organic electroluminescent devices manufactured in the above application examples and the organic electroluminescent devices manufactured in the control examples were measured under a current density of 10 mA / cm2, and the results are shown in Table 6 below.

[0150] Table 6

[0151]

[0152]

[0153]

[0154] As shown in the table above, when the compounds of the present invention are applied to organic electroluminescent devices, the luminous efficiency is significantly improved at the same current density, the device's start-up voltage is reduced, and the device's power consumption is relatively reduced.

[0155] The organic electroluminescent devices prepared in Comparative Examples 1-3, Application Examples 1-15, and 35-40 were subjected to luminescence lifetime tests to obtain the luminescence lifetime T97% data (the time for the luminous brightness to decrease to 97% of the initial brightness). The testing equipment was a TEO luminescent device lifetime testing system. The results are shown in Table 7.

[0156] Table 7

[0157]

[0158]

[0159] As shown in the table above, when the compounds of this invention are applied to organic electroluminescent devices, the lifespan is significantly improved at the same current density, indicating broad application prospects.

[0160] It should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not intended to limit it. Although the present invention has been described in detail with reference to preferred embodiments, those skilled in the art should understand that modifications or equivalent substitutions can be made to the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, and all such modifications or substitutions should be covered within the scope of the claims of the present invention.

Claims

1. An amino compound, characterized in that, Selected from the compounds shown in Formula 1: L1 and L2 are each independently a single bond, a substituted or unsubstituted C6-C20 aryl group, and the substituent is selected from one or more of deuterium, fluorine, cyano, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl. Ar1 and Ar2 are substituted or unsubstituted groups of the following: C6-C30 aryl or C5-C30 heteroaryl, wherein the substituent is selected from one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl; R is a deuterium, fluorine, cyano, or a deuterated or undeuterated group of the following: one of C1-C10 alkyl groups or C4-C8 cycloalkyl groups; A1-A5 are each independently hydrogen or deuterium, and at least one of A1-A5 is deuterium.

2. An amino compound as described in claim 1, characterized in that, Ar1 and Ar2 are substituted or unsubstituted groups of the following: aryl (C6-C18) or heteroaryl (C5-C24), wherein the substituent is selected from one or more of deuterium, fluorine, cyano, alkyl (C1-C6), deuterated alkyl (C1-C6), aryl (C6-C18), deuterated aryl (C6-C18), and heteroaryl (C5-C24); L1 and L2 are independently single-bonded, substituted or unsubstituted phenyl, naphthyl, or biphenyl groups, respectively, and their substituents are selected from one or more of deuterium, fluorine, cyano, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl. R is a deuterated or undeuterated group of the following: one of C1-C10 alkyl groups or C5-C8 cycloalkyl groups; A1-A5 are each independently hydrogen or deuterium, with 3-5 of A1-A5 being deuterium.

3. An amino compound as described in claim 1, characterized in that, Its structural formula is shown in Equation 2 below: Ar1 and Ar2 are substituted or unsubstituted groups of the following: phenyl, biphenyl, naphthyl, anthracene, dibenzofuranyl, dibenzothiophene, fluorenyl, phenanthrene, benzophenanthrenefuranyl, wherein the substituent is selected from one or more of deuterium, fluorine, cyano, methyl, C6-C12 aryl, C6-C12 deuterated aryl, and C5-C20 heteroaryl; L1 and L2 are independently single bonds, phenyl, naphthyl, and biphenyl, respectively; R is a deuterated or undeuterated group of the following: one of C1-C6 alkyl groups or C5-C8 cycloalkyl groups.

4. An amino compound as described in claim 1, characterized in that, Ar1 and Ar2 are substituted or unsubstituted groups of the following: phenyl, biphenyl, naphthyl, anthracene, dibenzofuranyl, dibenzothiophene, fluorenyl, phenanthrene, benzophenanthrenefuranyl, wherein the substituent is selected from one or more of deuterium, fluorine, cyano, methyl, C6-C12 aryl, C6-C12 deuterated aryl, and C5-C20 heteroaryl; L1 and L2 are independently single bonds, phenyl, and biphenyl, respectively.

5. An amino compound as described in claim 1, characterized in that, Ar1 is 9,9-dimethylfluorene; Ar2 can be a substituted or unsubstituted group of the following: phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, wherein the substituent is selected from one or more of deuterium, methyl, and phenyl; L1 and L2 are independently single bonds, phenyl, and biphenyl, respectively; R is a deuterated or undeuterated group of the following: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, or cyclohexyl.

6. An amino compound as described in claim 1, characterized in that, The amine compound is one of the following structural formulas:

7. An organic electroluminescent device comprising the compound of claim 1, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer contains an organic electroluminescent compound as described in any one of claims 1-6.

8. The organic electroluminescent device according to claim 7, characterized in that, The organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; at least one of the hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, and electron injection layer contains an organic electroluminescent compound as described in any one of claims 1-6.

9. The organic electroluminescent device according to claim 8, characterized in that, The electron blocking layer contains an organic electroluminescent compound as described in any one of claims 1-6.

10. The organic electroluminescent device according to claim 7, characterized in that, The compound of the present invention is applied in the organic electroluminescent device, which can be used in the manufacturing of electronic display devices or OLED lighting devices.

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