A compound, preparation method and application thereof

Abstract

The present invention provides a compound, a preparation method, and an application thereof. The compound has a structural formula as shown in Formula I. It can be used to prepare the first host material of the light-emitting layer in an organic electroluminescent device. When used in combination with a specific second host material, the prepared organic electroluminescent device can have high luminous efficiency, low driving voltage, and long life. According to research, at a brightness of 5000 cd / m 2 The organic electroluminescent device was tested under the conditions of , the luminous efficiency was higher than 34cd / A, the driving voltage was lower than 4.5V, and the T95 life was higher than 240h.

Description

Technical Field

[0001] The present invention belongs to the field of organic photoelectric materials, and in particular relates to a compound, a preparation method and application thereof. Background Art

[0002] The phenomenon of organic electroluminescence was discovered as early as the early 20th century. Chinese-American professor Ching-Yun Tang, born in Hong Kong in 1947, discovered organic light-emitting diodes (OLEDs) in his laboratory, sparking research on them.

[0003] Organic light-emitting devices (OLEDs) typically consist of a cathode, an anode, and an organic layer inserted between them. Typically, a device consists of a transparent ITO anode, a hole injection layer (ETL), a hole transport layer (HTL), a light-emitting layer (EL), a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), and a cathode. One or two organic layers can be omitted as needed. The OLED mechanism of operation is that a voltage is applied between the two electrodes, electrons are injected from the cathode, and holes are injected from the anode. The electrons and holes recombine in the light-emitting layer to form an excited state, which is then excited back to a stable ground state, causing the device to emit light.

[0004] The inherent properties of organic materials, such as flexibility, make them well-suited for specialized applications, such as fabrication on flexible substrates. Organic optoelectronic devices include organic light-emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the performance of organic materials can offer advantages over conventional materials. For example, the wavelength of light emitted by the organic emissive layer can generally be more easily adjusted using appropriate dopants. When a voltage is applied to the device, the organic film emits light. OLEDs can also be used in flat-panel displays, lighting, and backlighting. Consequently, OLEDs have been extensively researched, developed, and used in various fields.

[0005] At present, the materials of organic light-emitting devices mainly have technical problems such as short lifespan, low luminous efficiency and power efficiency, and high driving voltage, which increases the cost of using such materials and poses a great obstacle to market development in the future.

[0006] Therefore, developing a new organic condensed ring compound to prepare an organic electroluminescent device with low driving voltage, high luminous efficiency and long service life is a technical problem that needs to be solved urgently by people in this field. Summary of the Invention

[0007] In view of this, the present invention aims to provide a compound, a preparation method, and applications thereof. The compound can be used to prepare a first host material for the light-emitting layer of an organic electroluminescent device. When used in combination with a specific second host material, the resulting device exhibits high luminous efficiency, low driving voltage, and long life.

[0008] To achieve this object, the present invention adopts the following technical solutions:

[0009] In a first aspect, the present invention provides a compound, the structural formula of which is shown in Formula I:

[0010]

[0011] wherein R1, R2, R3, and R4 are each independently selected from substituted or unsubstituted C1 to C8 alkyl, substituted or unsubstituted C3 to C 15 Cycloalkyl, substituted or unsubstituted C3~C 15 Heterocycloalkyl, substituted or unsubstituted C6~C 18 aryl or substituted or unsubstituted C4~C 12 heteroaryl;

[0012] The heteroatoms in the heterocycloalkyl or heteroaryl groups in R1, R2, R3, and R4 are selected from any one or more of N, O, S, Si, Se, and Ge;

[0013] a is selected from any integer between 0 and 3, b is selected from any integer between 0 and 2, c is selected from any integer between 0 and 2, and d is selected from any integer between 0 and 5;

[0014] The R5 is selected from substituted or unsubstituted C6 to C 30 aryl, substituted or unsubstituted C3~C 30 Heteroaryl, substituted or unsubstituted C3~C 30 Cycloalkyl, substituted or unsubstituted C3~C 30 Heterocycloalkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted tri(C1~C 30 ) alkylsilyl, substituted or unsubstituted di(C1~C 30 )alkyl (C6~C 30 ) arylsilyl, substituted or unsubstituted (C1~C 30 )alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6~C 30 ) arylsilyl, substituted or unsubstituted mono(C1~C 30 ) alkylamino, substituted or unsubstituted di(C1~C 30) alkylamino, substituted or unsubstituted mono- or di-(C6~C 30 ) arylamino, substituted or unsubstituted (C1~C 30 )alkyl (C6~C 30 )arylamino, -L1-NR6R7 or -R8-(L2-R9) e ;

[0015] Wherein, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted C6 to C 30 arylene or substituted or unsubstituted C3~C 30 R6 and R7 are each independently selected from substituted or unsubstituted C1 to C 30 Alkyl, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C6~C 30 aryl or substituted or unsubstituted C3~C 30 heteroaryl, R8 is substituted or unsubstituted C3~C 20 heteroaryl, R9 is selected from substituted or unsubstituted C1~C 30 Alkyl, substituted or unsubstituted C3~C 30 cycloalkyl, substituted or unsubstituted C3~C7 heterocycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C3~C 30 Heteroaryl, substituted or unsubstituted tri(C1~C 30 ) alkylsilyl, substituted or unsubstituted di(C1~C 30 )alkyl (C6~C 30 ) arylsilyl, substituted or unsubstituted (C1~C 30 )alkyldi(C6~C 30 ) arylsilyl or substituted or unsubstituted tri(C6~C 30 ) arylsilyl;

[0016] The heteroatom of the heteroarylene group in L1 or L2 is selected from any one or more of N, O, S, Si, Se or Ge;

[0017] The heteroatom in the heterocycloalkyl or heteroaryl group in R5 or R9 is selected from any one or more of N, O, S, Si, Se or Ge;

[0018] The heteroatom in the heteroaryl group in R6 or R7 is selected from any one or more of N, O, S, Si, Se or Ge;

[0019] The heteroatom in the heteroaryl group in R8 is selected from N;

[0020] e is selected from 1 or 2. When e is 2, two -(L2-R9) are the same or different.

[0021] Preferably, the R1, R2, R3, and R4 are each independently selected from substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C3-C 15 Cycloalkyl, substituted or unsubstituted C3~C 15 Heterocycloalkyl, substituted or unsubstituted C6~C 18 aryl or substituted or unsubstituted C4~C 12 wherein the heteroaryl group is a heteroaryl group, and the heteroatom in the heterocycloalkyl group or heteroaryl group in R1, R2, R3, and R4 is selected from any one or more of N, O, S, and Si.

[0022] More preferably, the C1-C4 alkyl group is selected from any one of methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl.

[0023] More preferably, the C3 to C 15 The cycloalkyl group is selected from any one of cyclopropyl, cyclopentyl, cyclohexyl and adamantyl.

[0024] More preferably, the C6~C 18 The aryl group is selected from any one of benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene or pyrene.

[0025] More preferably, the structural formula of the compound is selected from any one of the following formulas (C-1-001) to (C-2-175):

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039] In a second aspect, the present invention provides a method for preparing the above-mentioned compound, comprising the following steps:

[0040] Mixing raw material A, raw material B, an alkaline substance, a solvent, and a catalyst shown in Formula 1 and heating the mixture to react, cooling the mixture after the reaction is completed to obtain a precipitate, subjecting the precipitate to column chromatography, and concentrating the filtrate until a solid precipitates to obtain the target compound;

[0041] The raw material B includes an R5 group. When the R5 group contains an amino group, the chemical formula of the raw material B is R5-H. When the R5 group does not contain an amino group, the chemical formula of the raw material B is R5-B(OH)2;

[0042]

[0043] Preferably, the alkaline substance comprises potassium carbonate and / or sodium carbonate.

[0044] Preferably, the solvent is a mixed solution of toluene, ethanol and water.

[0045] Preferably, the catalyst is selected from tetrakis(triphenylphosphine)palladium.

[0046] Preferably, the molar ratio of the raw material A, raw material B, alkaline substance and catalyst is 1:(1.1-1.5):(1.1-2):(0.005-0.05).

[0047] Preferably, the ratio of the raw material A to the solvent is 50 mmol: (350-400) mL.

[0048] In a third aspect, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and an intermediate layer disposed between the anode and the cathode; the intermediate layer comprises a light-emitting layer, the light-emitting layer comprises a host material, the host material comprises a first host material and a second host material; the mass ratio of the first host material to the second host material is (1 to 99): (99 to 1); the first host material comprises the compound of the above technical solution; the structural formula of the second host material is selected from any one of the following formulas (H-2-1) to (H-2-145):

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055] Preferably, the light-emitting layer further comprises a dopant.

[0056] Preferably, the dopant includes a fluorescent dopant and / or a phosphorescent dopant.

[0057] Preferably, the mass ratio of the host material to the dopant is (90-99.5):(0.5-10).

[0058] Preferably, the intermediate layer further includes a functional layer.

[0059] Preferably, the functional layer includes any one or more of a hole injection layer, a hole transport layer, a hole injection-hole transport functional layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron transport-electron injection functional layer.

[0060] Compared with the prior art, the present invention has the following beneficial effects:

[0061] The compound provided by the present invention has a simple preparation method and is easy to achieve industrial production. When used in combination with a specific second host material to prepare the light-emitting layer in an organic electroluminescent device, the prepared device can have the characteristics of high luminous efficiency, low driving voltage and long life. 2 The device was tested under the conditions of 3.5V, the luminous efficiency was higher than 34cd / A, the driving voltage was lower than 4.5V, and the T95 life was higher than 240h. DETAILED DESCRIPTION

[0062] The following will clearly and completely describe the technical solutions of the present invention in conjunction with the embodiments of the present invention. Obviously, the embodiments described are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative efforts are within the scope of protection of the present invention.

[0063] In view of the problems of short lifespan, low luminous efficiency and high driving voltage of organic light-emitting devices in the prior art, the present invention provides a compound, the structural formula of which is shown in Formula I:

[0064]

[0065] wherein R1, R2, R3, and R4 are each independently selected from substituted or unsubstituted C1 to C8 alkyl, substituted or unsubstituted C3 to C 15 Cycloalkyl, substituted or unsubstituted C3~C 15 Heterocycloalkyl, substituted or unsubstituted C6~C 18 aryl or substituted or unsubstituted C4~C 12 heteroaryl;

[0066] The heteroatoms in the heterocycloalkyl or heteroaryl groups in R1, R2, R3, and R4 are selected from any one or more of N, O, S, Si, Se, and Ge;

[0067] a is selected from any integer from 0 to 3 (i.e., R1 is unsubstituted, mono-, di-, or tri-substituted), b is selected from any integer from 0 to 2 (i.e., R2 is unsubstituted, mono-, or di-substituted), c is selected from any integer from 0 to 2 (i.e., R3 is unsubstituted, mono-, or di-substituted), and d is selected from any integer from 0 to 5 (i.e., R4 is unsubstituted, mono-, di-, tri-, tetra-, or penta-substituted);

[0068] The R5 is selected from substituted or unsubstituted C6 to C 30 aryl, substituted or unsubstituted C3~C 30 Heteroaryl, substituted or unsubstituted C3~C 30 Cycloalkyl, substituted or unsubstituted C3~C 30 Heterocycloalkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted tri(C1~C 30 ) alkylsilyl, substituted or unsubstituted di(C1~C 30 )alkyl (C6~C 30 ) arylsilyl, substituted or unsubstituted (C1~C 30 )alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6~C 30 ) arylsilyl, substituted or unsubstituted mono(C1~C 30 ) alkylamino, substituted or unsubstituted di(C1~C 30 ) alkylamino, substituted or unsubstituted mono- or di-(C6~C 30 ) arylamino, substituted or unsubstituted (C1~C 30 )alkyl (C6~C 30 )arylamino, -L1-NR6R7 or -R8-(L2-R9) e ;

[0069] Wherein, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted C6 to C 30arylene or substituted or unsubstituted C3~C 30 R6 and R7 are each independently selected from substituted or unsubstituted C1 to C 30 Alkyl, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C6~C 30 aryl or substituted or unsubstituted C3~C 30 heteroaryl, R8 is substituted or unsubstituted C3~C 20 heteroaryl, R9 is selected from substituted or unsubstituted C1~C 30 Alkyl, substituted or unsubstituted C3~C 30 cycloalkyl, substituted or unsubstituted C3~C7 heterocycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C3~C 30 Heteroaryl, substituted or unsubstituted tri(C1~C 30 ) alkylsilyl, substituted or unsubstituted di(C1~C 30 )alkyl (C6~C 30 ) arylsilyl, substituted or unsubstituted (C1~C 30 )alkyldi(C6~C 30 ) arylsilyl or substituted or unsubstituted tri(C6~C 30 ) arylsilyl;

[0070] The heteroatom of the heteroarylene group in L1 or L2 is selected from any one or more of N, O, S, Si, Se or Ge;

[0071] The heteroatom in the heterocycloalkyl or heteroaryl group in R5 or R9 is selected from any one or more of N, O, S, Si, Se or Ge;

[0072] The heteroatom in the heteroaryl group in R6 or R7 is selected from any one or more of N, O, S, Si, Se or Ge;

[0073] The heteroatom in the heteroaryl group in R8 is selected from N;

[0074] e is selected from 1 or 2. When e is 2, two -(L2-R9) are the same or different.

[0075] The above-mentioned "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed into another substituent, and the position of substitution is not limited as long as the position is a position where a hydrogen atom is substituted, that is, a position where a substituent can replace, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0076] The term "substituted or unsubstituted" means deuterium, a halogen group, a nitrile group, a hydroxyl group, a carbonyl group, an ester group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, an alkylamino group, a heterocyclylamino group, an arylamino group, an aryl group or a heterocyclyl group, or a substituent in which two or more of the substituents shown above are linked together, or no substituent.

[0077] In some embodiments of the present invention, the structural formula of the compound is as shown in Formula I, wherein the C1-C8 alkyl in R1, R2, R3, and R4 can be a straight-chain alkyl or a branched alkyl, and the C3-C 15 The cycloalkyl group can be any of monocyclic alkyl, polycyclic alkyl or spiroalkyl, C6~C 18 The aromatic group may be a monocyclic group or a polycyclic group, wherein the polycyclic group has multiple rings with two carbon atoms shared by two adjacent rings, wherein at least one ring is an aromatic ring, and the other rings are at least one of cycloalkyl, cycloalkenyl, aryl or heteroaryl (the heteroatom is selected from any one or more of N, O, S, Si, Se or Ge), C4 to C 12 The heteroaryl group may be any of furan, thiophene, and pyridine.

[0078] In some embodiments of the present invention, the structural formula of the compound is as shown in Formula I, wherein R1, R2, R3, and R4 are each independently selected from substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C3-C 15 Cycloalkyl, substituted or unsubstituted C3~C 15 Heterocycloalkyl, substituted or unsubstituted C6~C 18 aryl or substituted or unsubstituted C4~C 12 wherein the heteroaryl group is a heteroaryl group, and the heteroatom in the heterocycloalkyl group or heteroaryl group in R1, R2, R3, and R4 is selected from any one or more of N, O, S, and Si.

[0079] In some embodiments of the present invention, the C1-C4 alkyl group is further selected from any one of methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl, and the C3-C 15 The cycloalkyl group is further selected from any one of cyclopropyl, cyclopentyl, cyclohexyl or adamantyl, and the C6 to C 18 The aryl group is further selected from any one of benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene or pyrene.

[0080] In some embodiments of the present invention, the structural formula of the compound is specifically selected from any one of Formulas (C-1-001) to (C-2-175). The specific chemical formulas are as described above in the present invention and are not repeated here. It should be noted that the chemical formulas shown in Formulas (C-1-001) to (C-2-175) are merely examples and are not intended to be limiting.

[0081] The compound provided by the present invention can be used as the first host material of the light-emitting layer in an organic electroluminescent device, and used in combination with a specific second host material. Compared with other host materials in the prior art, the prepared device can have the characteristics of low driving voltage, high luminous efficiency and long service life, which has great practical significance.

[0082] The present invention also provides a method for preparing the above compound, comprising the following steps:

[0083] Mixing raw material A, raw material B, an alkaline substance, a solvent, and a catalyst shown in Formula 1 and heating the mixture to react, cooling the mixture after the reaction is completed to obtain a precipitate, subjecting the precipitate to column chromatography, and concentrating the filtrate until a solid precipitates to obtain the target compound;

[0084] The raw material B includes an R5 group. When the R5 group contains an amino group, the chemical formula of the raw material B is R5-H. When the R5 group does not contain an amino group, the chemical formula of the raw material B is R5-B(OH)2;

[0085]

[0086] The R1, R2, R3, and R4 are as described in the above technical solution, and will not be described in detail here.

[0087] In the present invention, the raw material A, raw material B, alkaline substance, solvent and catalyst shown in formula 1 are mixed and heated to react. After the reaction is completed, the temperature is lowered to obtain a precipitate, the precipitate is chromatographed, and the filtrate is concentrated until a solid precipitates to obtain the target compound. The reaction is preferably carried out in an inert atmosphere, and the inert atmosphere is nitrogen or argon gas well known to those skilled in the art. In some embodiments of the present invention, first, under an inert atmosphere, raw material A, raw material B, alkaline substance and catalyst are mixed according to a molar ratio of 1: (1.1-1.5): (1.1-2): (0.005-0.05). The chemical formulas of raw material A and raw material B are as described above. The alkaline substance includes potassium carbonate and / or sodium carbonate, preferably potassium carbonate, and the catalyst is selected from tetrakis(triphenylphosphine) palladium. Then, a solvent is added to react according to a ratio of raw material A to solvent of 50mmol: (350-400)mL. The solvent is preferably a mixed solution of toluene, ethanol and water, and the volume ratio of toluene, ethanol and water is preferably 2: 1: 1; the catalyst is selected from tetrakis(triphenylphosphine) palladium. The reaction temperature is preferably 70-110°C, and the reaction time is 20-30 hours. In some embodiments of the present invention, the molar ratio of raw material A to the alkaline substance is preferably 1:1.5, the molar ratio of raw material A to raw material B is preferably 1:1.2, and the molar ratio of raw material A to the catalyst is preferably 1:0.01. After the heating reaction is completed, the temperature is cooled to room temperature to obtain a precipitate. In some embodiments of the present invention, the precipitate is preferably filtered and rinsed before chromatography. The reagent used for the rinse can be any one or more of water, anhydrous ethanol, or petroleum ether, and then dried at 70-80°C for at least 8 hours. In the present invention, the chromatography is preferably silica gel column chromatography, which is a technique well known to those skilled in the art. In some embodiments of the present invention, petroleum ether is first thoroughly stirred and added to the silica gel column. After the silica gel settles, the precipitate is added and purified using a mixed solution of dichloromethane and petroleum ether as the developing solvent and a mixed solution of dichloromethane and petroleum ether as the eluent to ultimately obtain the target compound.

[0088] The preparation method of the above-mentioned compound provided by the present invention is simple, convenient, easy to implement, and convenient for industrial or industrial preparation.

[0089] The present invention also provides an organic electroluminescent device comprising an anode, a cathode, and an intermediate layer disposed between the anode and the cathode. In the present invention, the anode is selected from indium tin oxide, tin oxide, zinc oxide, or indium oxide, and has a thickness of 10 to 500 nm; the cathode is selected from Al, Li, Na, K, Mg, Ca, Au, Ag, or Pb, and has a thickness of 100 to 1000 nm. The intermediate layer comprises a light-emitting layer, and the light-emitting layer has a thickness of 10 to 500 nm. The light-emitting layer comprises a host material, which includes a first host material and a second host material. The first host material may be composed of a single or at least one of the aforementioned compounds, and may further include conventional materials used in organic electroluminescent devices. The second host material can be composed of a single second host material or at least one second host material, and can further include conventional materials in organic electroluminescent devices, and its structural formula is selected from any one of the following formulas (H-2-1) to (H-2-145), and the mass ratio of the first host material to the second host material is (1 to 99): (99 to 1), preferably (10 to 90): (90 to 10), more preferably (30 to 70): (70 to 30), further preferably (40 to 60): (60 to 40), and most preferably 50:50.

[0090] The structural formulas shown in formulas (H-2-1) to (H-2-145) are as follows:

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] In some embodiments of the present invention, the light-emitting layer further includes a dopant, which can be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device of the present invention is not particularly limited, and can be selected from metallized complexes of iridium (Ir), (Os), copper (Cu) or platinum (Pt), preferably ortho-metallized complexes of iridium (Ir), (Os), copper (Cu) or platinum (Pt), more preferably ortho-metallized iridium complexes. In one embodiment of the present invention, the dopant uses the phosphorescent compound of European patent application 07102949.0, and the doping concentration of the dopant compound in the light-emitting layer is less than 20wt% relative to the main compound. In one embodiment of the present invention, the main material and the dopant are mixed and evaporated at a mass ratio of 90:10 for 30nm to form a light-emitting layer.

[0098] In some embodiments of the present invention, the intermediate layer further includes a functional layer, and the functional layer includes any one or more of a hole injection layer, a hole transport layer, a hole injection-hole transport functional layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron transport-electron injection functional layer.

[0099] The compound provided by the present invention is used as the first host material in the light-emitting layer in combination with a specific second host material, and the prepared organic electroluminescent device has the characteristics of low driving voltage, high luminous efficiency and long service life. 2 The device was tested under the conditions of 3.5V, the luminous efficiency was higher than 34cd / A, the driving voltage was lower than 4.5V, and the T95 life was higher than 240h.

[0100] To further illustrate the present invention, the following examples are provided for detailed description. The sources of the raw materials used in the following examples are not particularly limited and can be purchased from the market or prepared according to conventional preparation methods known to those skilled in the art.

[0101] Preparation Example 1

[0102] This preparation example provides a compound A, and the synthesis route is as follows:

[0103]

[0104] The specific steps are as follows:

[0105] (1) Synthesis of A-1: ​​120 mL of acetic acid was added to N-methyl-2-nitroaniline (CAS No.: 612-28-2) (10 g, 66 mmol) and N-bromosuccinimide (CAS No.: 128-08-5) (11.8 g, 66 mmol), and the mixture was refluxed for 12 h. After the reaction, 1 L of distilled water was added, the precipitate was filtered, dissolved in dichloromethane, and subjected to column chromatography using dichloromethane and petroleum ether as solvents. The product was concentrated, dried, and dried to obtain an orange substance A-1 (7.2 g, yield: 47.2%).

[0106] The mass spectrometry and hydrogen spectrum tests on the orange substance A-1 showed the following results:

[0107] Mass spectrometry test: theoretical value is 231.05; test value is 231.11;

[0108] 1HNMR (500MHz, Chloroform-d)

[0109] (1H,8.25-8.23)(1H.7.53-7.49)(1H,7.40-7.35)(1H,7.21-7.18)(3H,3.09-3.15)

[0110] (2) Synthesis of A-2: A-1 (6.8 g, 29 mmol) was dissolved in 25 mL of pyridine, and benzoyl chloride (5 g, 35 mmol) (CAS No.: 98-88-4) was added. The mixture was reacted at 100°C for 10 h under nitrogen protection. After the reaction, 500 mL of dichloromethane was added. The organic phase was then washed with 500 mL of saturated brine and dried. The organic phase was then subjected to silica gel column chromatography using dichloromethane as the solvent. The filtrate was concentrated until solids precipitated to obtain a white-green solid A-2 (5.6 g, yield: 57%).

[0111] The mass spectrometry test results of the green solid A-2 are as follows:

[0112] Mass spectrometry test: theoretical value is 335.16; test value is 334.11;

[0113] (3) Synthesis of A-3: A-2 (5 g, 14.7 mmol) was dissolved in 100 mL of tetrahydrofuran, and sodium bisulfite (13.1 g, 74.7 mmol) aqueous solution (100 mL) was added under nitrogen protection, and then 20 mL of methanol was added, and stirred for 5 h. 100 mL of ethyl acetate and sodium bicarbonate (6.3 g, 74.7 mmol) aqueous solution (100 mL) were added, and stirred at room temperature for 1 h. The mixture was extracted with 500 mL of DCM, and the organic phase was washed with 500 mL of saturated brine, and then dried. The organic phase was then subjected to silica gel column chromatography using dichloromethane as the solvent, and the filtrate was concentrated until solid precipitated to obtain white crystals A-3 (4 g, yield: 87.7%).

[0114] The mass spectrometry test results of the white crystal A-3 are as follows:

[0115] Mass spectrometry test: theoretical value is 305.18; test value is 304.02;

[0116] (4) Synthesis of A-4: A-3 (3.9 g, 13 mmol) was mixed with 50 mL of xylene and stirred for 1 h. Toluenesulfonic acid monohydrate (1.5 g, 7.7 mmol) was added and refluxed for 10 h. After the reaction was completed, the temperature was lowered and the mixture was filtered. The solid was dissolved in dichloromethane and subjected to silica gel column chromatography. The filtrate was concentrated until solid precipitated to obtain white crystals of A-4 (6 g, yield: 82.1%).

[0117] The mass spectrometry and hydrogen spectrum tests on the white crystal A-4 were performed, and the results were as follows:

[0118] Mass spectrometry test: theoretical value is 287.16; test value is 286.01;

[0119] (5) Synthesis of A-5: Compound A-4 (6 g, 21 mmol), 5-chloro-2-formylphenylboronic acid (CAS No.: 870238-36-1) (3.88 g, 21 mmol), tetrakis(triphenylphosphine)palladium (1.2 g, 1 mmol), sodium carbonate (5.3 g, 50.7 mmol), toluene (80 mL), ethanol (20 mL), and distilled water (20 mL) were added to a reaction vessel and refluxed at 100°C with stirring for 6 h. A precipitate was precipitated. The precipitate was filtered, rinsed with water, anhydrous ethanol, and petroleum ether in sequence, and dried. The precipitate was then subjected to silica gel column chromatography using dichloromethane as the solvent. The filtrate was concentrated until a solid precipitated to obtain intermediate A-5 (3.1 g, yield: 42.6%).

[0120] The mass spectrometry test results for intermediate A-5 are as follows:

[0121] Mass spectrometry test: theoretical value is 346.81; test value is 346.08;

[0122] (6) Synthesis of A-6: Compound A-5 (3 g, 8 mmol), (methoxymethyl)triphenylphosphonium chloride (5.1 g, 12 mmol) and tetrahydrofuran (100 mL) were introduced into a reaction vessel, and the reaction mixture was stirred for 15 min. The temperature was lowered to 0°C, and potassium tert-butoxide (1 M in THF, 15 mL) was slowly added dropwise. The mixture was slowly heated to 25°C and then stirred for 5 h. 15 mL of distilled water was added, and the system was extracted three times with 240 mL of dichloromethane. The organic phase was dried and subjected to silica gel column chromatography using dichloromethane as the solvent. The filtrate was concentrated until a solid precipitated to obtain intermediate A-6 (1.5 g, yield: 50%).

[0123] The mass spectrometry test results for intermediate A-6 are as follows:

[0124] Mass spectrometry test: theoretical value is 374.87; test value is 374.12;

[0125] (7) Synthesis of Compound A: Compound A-6 (1.5 g, 4 mmol), Eaton's reagent (0.2 mL) and chlorobenzene (675 mL) were introduced into a reaction vessel and the mixture was stirred under reflux for 3 h. After the reaction was completed, the mixture was cooled to room temperature and then extracted with dichloromethane. The organic phase was dried by rotary evaporation and then subjected to silica gel column chromatography using dichloromethane as the solvent. The filtrate was concentrated until a solid precipitated to obtain Compound A (1 g, yield: 73%).

[0126] The mass spectrometry test results for compound A are as follows:

[0127] Mass spectrometry test: theoretical value is 342.83; test value is 342.09;

[0128] 1HNMR (500MHz, Chloroform-d)

[0129] (1H,8.70-8.69)(2H.7.97-7.90)(1H,7.87-7.84)(2H7.83-7.80)(2H,7.73-7.66)(3H.7.51-7.42)(1H,7.39-7.36)(3H,3.97-3.94)

[0130] After a sufficient amount of compound A is prepared according to the above method, the preparation of the final product compound C is started.

[0131] Example 1

[0132] This embodiment provides a luminescent compound, the chemical formula of which is shown in C-1-013, and the synthesis route is as follows:

[0133]

[0134] The specific steps are as follows:

[0135] Under nitrogen, compounds A-1-013 (29.17 mmol, 10.0 g), B-1-013 (35 mmol, 8.68 g) (CAS No. 1922905-62-1), and potassium carbonate (43.75 mmol, 6.05 g) were weighed and placed into a reaction system. A mixed solution of 200 mL of toluene, 100 mL of ethanol, and 100 mL of purified water was added. Tetrakis(triphenylphosphine)palladium (0.029 mmol, 0.33 g) was added under nitrogen. The mixture was heated under reflux at 95°C for 24 hours. The mixture was then cooled to 25°C, whereupon a precipitate formed. The precipitate was filtered, rinsed with water, anhydrous ethanol, and petroleum ether, followed by drying. The precipitate was then purified by silica gel column chromatography using dichloromethane and petroleum ether as solvents. The filtrate was concentrated until a solid precipitated, yielding the bridged ligand C-1-013 as a yellow powder (7.8 g, 52.37% yield).

[0136] The conditions for silica gel column chromatography are as follows: dichloromethane and petroleum ether are selected as solvents, silica gel (200-300 mesh) is used as adsorbent, 500 g of silica gel is weighed, petroleum ether is added, stirred thoroughly until uniform, and then poured into the column, after the silica gel settles, the mixture is added, and the developing solvent is dichloromethane: petroleum ether = 1:10 (volume ratio), and the eluent is used for purification.

[0137] The yellow powdered bridging ligand compound was tested and analyzed, and the results were as follows:

[0138] PLC purity: >99%;

[0139] Mass spectrometry test: theoretical value is 510.64; test value is 510.21;

[0140] Elemental analysis:

[0141] Calculated values: C: 89.38%; H: 5.13%; N: 5.49%;

[0142] The test values ​​are: C:89.37%; H:5.12%; N:5.51%;

[0143] 1HNMR (500MHz, Chloroform-d)δ

[0144] (1H,7.57-7.66)(1H,8.33-8.30)(2H,8.01-7.95)(3H,7.95-7.82)(3H,7.82-7.72) (3H,7.70-7.62)(2H,7.62-7.56)(7H,7.52-7.43)(1H,7.43-4.34)(3H,4.00-3.95)

[0145] From the above test results, it can be seen that Example 1 prepared a high-purity compound as shown in the structure of C-1-013.

[0146] Example 2

[0147] This embodiment provides a luminescent compound, whose chemical formula is shown in C-1-005, and the synthesis route is as follows:

[0148]

[0149] The specific steps are as follows:

[0150] Under nitrogen, compounds A-1-005 (29.17 mmol, 10.0 g), B-1-005 (35 mmol, 6.02 g) (CAS No. 13922-41-3), and potassium carbonate (43.75 mmol, 6.05 g) were weighed and placed into a reaction system. A mixed solution of 200 mL of toluene, 100 mL of ethanol, and 100 mL of purified water was added. Tetrakis(triphenylphosphine)palladium (0.029 mmol, 0.338 g) was added under nitrogen. The mixture was heated under reflux at 95°C for 24 hours. The mixture was then cooled to 25°C, whereupon a precipitate formed. The precipitate was filtered, rinsed with water, anhydrous ethanol, and petroleum ether, sequentially, and dried. The precipitate was then purified by silica gel column chromatography using dichloromethane and petroleum ether as solvents. The filtrate was concentrated until a solid precipitated, yielding the bridged ligand C-1-005 (10.93 g, 51.13% yield) as a yellow powder.

[0151] The conditions for silica gel column chromatography are as follows: dichloromethane and petroleum ether are selected as solvents, silica gel (200-300 mesh) is used as the adsorbent, 500 g of silica gel is weighed, petroleum ether is added, stirred thoroughly until uniform, and then poured into the column, after the silica gel is settled, the mixture is added, the developing solvent ratio is dichloromethane: petroleum ether = 1:8 (volume ratio), and the eluent is used for purification.

[0152] The yellow powdered bridging ligand compound was tested and analyzed, and the results were as follows:

[0153] HPLC purity: >99%;

[0154] Mass spectrometry test: theoretical value is 434.18; test value is 434.54;

[0155] Elemental analysis:

[0156] Calculated values ​​are: C: 88.45%; H: 5.10%; N: 6.45%;

[0157] The test values ​​are: C:88.46%; H:5.11%; N:6.43%;

[0158] From the above test results, it can be seen that Example 2 prepared a high-purity compound as shown in the structure of C-1-005.

[0159] Example 3

[0160] This embodiment provides a luminescent compound, whose chemical formula is shown in C-1-131, and the synthesis route is as follows:

[0161]

[0162] The specific steps are as follows:

[0163] Under nitrogen protection, compound A-1-131 (29.17 mmol, 10.0 g), B-1-131 (35 mmol, 8.55 g) (CAS number: 201802-67-7), and potassium carbonate (43.75 mmol, 6.05 g) were weighed and placed in the reaction system. A mixed solution of 200 mL of toluene, 100 mL of ethanol, and 100 mL of purified water was added. Under nitrogen protection, tetrakis(triphenylphosphine)palladium (0.029 mmol, 0.338 g) was added. Under nitrogen protection, the mixture was heated under reflux at 95°C for 24 hours. Then, it was cooled to 25°C. A precipitate was precipitated. The precipitate was filtered, rinsed with water, anhydrous ethanol, and petroleum ether in sequence, and dried. Then, silica gel column chromatography was performed using dichloromethane and petroleum ether as solvents. The filtrate was concentrated until a solid precipitated to obtain the bridged ligand C-1-131 (8.41 g, 52.26% yield) as a yellow powder.

[0164] The conditions for silica gel column chromatography are as follows: dichloromethane and petroleum ether are selected as solvents, silica gel (200-300 mesh) is used as the adsorbent, 500 g of silica gel is weighed, petroleum ether is added, stirred thoroughly until uniform, and then poured into the column, after the silica gel is settled, the mixture is added, the developing solvent ratio is dichloromethane: petroleum ether = 1:8 (volume ratio), and the eluent is used for purification.

[0165] The yellow powdered bridging ligand compound was tested and analyzed, and the results were as follows:

[0166] HPLC purity: >99%;

[0167] Mass spectrometry test: theoretical value is 551.24; test value is 551.69;

[0168] Elemental analysis:

[0169] Calculated values: C: 87.08%; H: 5.30%; N: 7.62%;

[0170] The test values ​​are: C:87.07%; H:5.31%; N:7.62%;

[0171] From the above test results, it can be seen that Example 3 prepared a high-purity compound as shown in the structure of C-1-131.

[0172] Example 4

[0173] This embodiment provides a luminescent compound, whose chemical formula is shown in C-2-015, and the synthesis route is as follows:

[0174]

[0175] The specific steps are as follows:

[0176] Under nitrogen, compounds A-2-015 (29.17 mmol, 10.0 g), B-2-015 (35 mmol, 5.28 g) (CAS No. 1309982-36-2), and potassium carbonate (43.75 mmol, 6.05 g) were weighed and placed into a reaction system. A mixed solution of 200 mL of toluene, 100 mL of ethanol, and 100 mL of purified water was added. Tetrakis(triphenylphosphine)palladium (0.029 mmol, 0.33 g) was added under nitrogen. The mixture was heated under reflux at 95°C for 24 hours. The mixture was then cooled to 25°C, whereupon a precipitate formed. The precipitate was filtered, rinsed with water, anhydrous ethanol, and petroleum ether, sequentially, and dried. The precipitate was then purified by silica gel column chromatography using dichloromethane and petroleum ether as solvents. The filtrate was concentrated until a solid precipitated, yielding the bridged ligand C-2-015 as a yellow powder (7.24 g, 60.02% yield).

[0177] The conditions for silica gel column chromatography are as follows: dichloromethane and petroleum ether are selected as solvents, silica gel (200-300 mesh) is used as adsorbent, 500 g of silica gel is weighed, petroleum ether is added, stirred thoroughly until uniform, and then poured into the column, after the silica gel is settled, the mixture is added, the developing solvent ratio is dichloromethane: petroleum ether = 1:10 (volume ratio), and the eluent is used for purification.

[0178] The yellow powdered bridging ligand compound was tested and analyzed, and the results were as follows:

[0179] HPLC purity: >99%;

[0180] Mass spectrometry test: theoretical value is 413.19; test value is 413.53;

[0181] Elemental analysis:

[0182] Calculated values ​​are: C: 84.23%; H: 5.61%; N: 10.16%;

[0183] The test values ​​are: C:84.24%; H:5.62%; N:10.14%;

[0184] From the above test results, it can be seen that Example 4 prepared a high-purity compound as shown in the structure of C-2-015.

[0185] Example 5

[0186] This embodiment provides a luminescent compound, whose chemical formula is shown as C-2-053, and the synthesis route is as follows:

[0187]

[0188] The specific steps are as follows:

[0189] Under nitrogen protection, compounds A-2-053 (29.17 mmol, 10.0 g), B-2-053 (35 mmol, 15.83 g) (CAS No.: 2243760-57-6), and potassium carbonate (43.75 mmol, 6.05 g) were weighed and put into the reaction system. A mixed solution of 200 mL of toluene, 100 mL of ethanol and 100 mL of pure water was added. Under nitrogen protection, tetrakistriphenylphosphine palladium (0.029 mmol, 0.33 g) was added, and the reaction was heated to reflux at 95 ° C under nitrogen protection for 24 hours. The mixture was then cooled to 25°C, whereupon a precipitate was precipitated. The precipitate was filtered, rinsed with water, anhydrous ethanol, and petroleum ether in that order, and dried. The precipitate was then chromatographed on a silica gel column using dichloromethane and petroleum ether as solvents. The filtrate was concentrated until a solid precipitated to obtain the bridged ligand C-2-053 (10.71 g, 51.36% yield) as a yellow powder.

[0190] The conditions for silica gel column chromatography are as follows: dichloromethane and petroleum ether are selected as solvents, silica gel (200-300 mesh) is used as the adsorbent, 500 g of silica gel is weighed, petroleum ether is added, stirred thoroughly until uniform, and then poured into the column, after the silica gel is settled, the mixture is added, the developing solvent ratio is dichloromethane: petroleum ether = 1:7 (volume ratio), and the eluent is used for purification.

[0191] The yellow powdered bridging ligand compound was tested and analyzed, and the results were as follows:

[0192] HPLC purity: >99%;

[0193] Mass spectrometry test: theoretical value is 714.28; test value is 714.87;

[0194] Elemental analysis:

[0195] Calculated values ​​are: C: 87.37%; H: 4.79%; N: 7.84%;

[0196] The test values ​​are: C:87.38%; H:4.78%; N:7.84%;

[0197] From the above test results, it can be seen that Example 5 prepared a high-purity compound as shown in the structure of C-2-053.

[0198] Example 6

[0199] This embodiment provides a luminescent compound, the chemical formula of which is shown in C-2-071, and the synthesis route is as follows:

[0200]

[0201] The specific steps are as follows:

[0202] Under nitrogen protection, compounds A-2-071 (29.17 mmol, 10.0 g), B-2-071 (35 mmol, 16.46 g) (CAS No.: 2588220-43-1), and potassium carbonate (43.75 mmol, 6.05 g) were weighed and put into the reaction system. A mixed solution of 200 mL of toluene, 100 mL of ethanol and 100 mL of pure water was added. Under nitrogen protection, tetrakistriphenylphosphine palladium (0.029 mmol, 0.33 g) was added, and the reaction was heated at 95 ° C for 24 hours under nitrogen protection. The mixture was then cooled to 25°C, whereupon a precipitate formed. The precipitate was filtered, rinsed with water, anhydrous ethanol, and petroleum ether in that order, and dried. The precipitate was then chromatographed on a silica gel column using dichloromethane and petroleum ether as solvents. The filtrate was concentrated until a solid precipitated to obtain the bridged ligand C-2-071 (10.93 g, 51.13% yield) as a yellow powder.

[0203] The conditions for silica gel column chromatography are as follows: dichloromethane and petroleum ether are selected as solvents, silica gel (200-300 mesh) is used as adsorbent, 500 g of silica gel is weighed, petroleum ether is added, stirred thoroughly until uniform, and then poured into the column. After the silica gel settles, the mixture is added, and the developing solvent ratio is dichloromethane: petroleum ether = 1:8, and the eluent is used for purification.

[0204] The yellow powdered bridging ligand compound was tested and analyzed, and the results were as follows:

[0205] HPLC purity: >99%;

[0206] Mass spectrometry test: theoretical value is 732.30; test value is 732.89;

[0207] Elemental analysis:

[0208] Calculated values ​​are: C: 83.58%; H: 4.95%; N: 11.47%;

[0209] The test values ​​are: C:83.59%; H:4.93%; N:11.48%;

[0210] From the above test results, it can be seen that Example 6 prepared a high-purity compound as shown in the structure of C-2-071.

[0211] Examples 7 to 30

[0212] According to the preparation method of the above embodiment, compound A and compound B were replaced with compounds corresponding to the corresponding ligand structures in the target product, and the material amounts were adjusted accordingly according to the corresponding stoichiometric ratios to obtain the following series of luminescent compounds, as shown in Table 1 below. The products were detected and analyzed according to the detection method in Example 1, and the results showed that they were luminescent compounds of the corresponding structures.

[0213] Table 1

[0214]

[0215]

[0216] Application Example 1

[0217] This application example provides an organic electroluminescent device having a structure of ITO anode / HIL / HTL / EML / HBL / ETL / EIL / cathode, and a preparation method thereof is as follows;

[0218] a. ITO anode: the coating thickness is The ITO (indium tin oxide) glass substrate was cleaned twice in distilled water and ultrasonically washed for 30 minutes, then repeatedly cleaned twice with distilled water and ultrasonically washed for 10 minutes. After washing, it was ultrasonically washed in 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 other functional layers were sequentially vapor-deposited on it with the substrate as the anode;

[0219] b. HIL (hole injection layer): 60 nm of 2-TNATA (i.e., N1-(2-naphthyl)-N4,N4-di(4-(2-naphthyl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine) was evaporated to form a hole injection layer;

[0220] c. HTL (hole transport layer): 60 nm of NPB (i.e., N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine) was evaporated to form a hole transport layer;

[0221] d. EML (Emitting Layer): A 30 nm thick layer of host material and dopant was then deposited on the functional layer (mass ratio of host to dopant was 90:10) as the emissive layer. The host material was a first host compound of C-1-013 and a second host compound of H2-1 in a mass ratio of 50:50. The dopant was the phosphorescent compound described in European Patent Application 07102949.0 shown below.

[0222]

[0223] e. HBL (hole blocking layer): 10 nm of BAlq was evaporated to form a hole blocking layer;

[0224] f. ETL (electron transport layer): Alq3 40nm was evaporated to form an electron transport layer;

[0225] g. EIL (electron injection layer): 0.2 nm of LiF was evaporated to form an electron injection layer;

[0226] h. Cathode: Vapor-deposit Al 150nm to form a cathode to obtain an OLED device.

[0227] Application Example 2-29

[0228] This application example 2-29 provides 28 kinds of organic electroluminescent devices. Referring to the method of application example 1, the first luminescent compound of the structure such as C-1-013 is replaced by C-1-005, C-1-007, C-1-017, C-1-023, C-1-029, C-1-052, C-1-060, C-1-068, C-1-071, C-1-077, C-1-079, C-1-181, C-1-136, C-1-158, C-1-170, C-2-005, C-2-015, C-2-024, C-2-030, C-2-040, C-2-050, C-2-061, C-2-072, C-2-073, C-2-074, C-2-075, C-2-080, C-2-090, C-3-091, C-3-092, C-3-093, C-3-094, C-3-095, C-3-096, C-3-097, C-3-098, C-3-099, C-3-091, C-3-098, C-3-099, C-3-091, C-3-097, C-3-098, C-3-099, C-3-091, C-3-099, C-3-091, C-3-093, C-3-094, C-3-095, C-3-096, C-3-097, -2-038, C-2-039, C-2-043, C-2-049, C-2-053, C-2-056, C-2-063, C-2-065, C-2-071, C-2-074, and C-2-078, and the second main compound with a structure as shown in H2-1 is replaced by the compounds shown in H2-25, H2-46, H2-78, H2-101, and H2-139, respectively. The two are then mixed as main materials and doping materials for vapor deposition, and the corresponding organic electroluminescent devices are prepared, as shown in Table 2 below.

[0229] Table 2

[0230]

[0231]

[0232] Comparative Application Example 1

[0233] This comparative application example provides an organic electroluminescent device. Referring to the method of Application Example 1, the dual host material used in Application Example 1 is replaced with RH-1 as the host material and mixed with the dopant material for vapor deposition to prepare the corresponding organic electroluminescent device. The structural formula of RH-1 is:

[0234]

[0235] Comparative Application Example 2-16

[0236] This comparative application example provides 15 organic electroluminescent devices. Referring to the method of Application Example 1, the dual host material used in Application Example 1 is replaced with the compounds shown in D-1-1 and D-1-2 as the first host compound, and the compound shown in D-2-1 as the second host compound. The dual host material is mixed with the dopant material and evaporated to prepare the corresponding organic electroluminescent devices. The structural formulas of D-1-1, D-1-2, and D-2-1 are:

[0237]

[0238] See Table 3 below for details:

[0239] Table 3

[0240] Group First host compound Second host compound Comparative Application Example 2 D-1-1 D-2-1 Comparative Application Example 3 D-1-2 D-2-1 Comparative Application Example 4 D-1-1 H2-1 Comparative Application Example 5 D-1-1 H2-25 Comparative Application Example 6 D-1-2 H2-46 Comparative Application Example 7 D-1-2 H2-78 Comparative Application Example 8 C-1-013 D-2-1 Comparative Application Example 9 C-1-023 D-2-1 Comparative Application Example 10 C-1-131 D-2-1 Comparative Application Example 11 D-1-1 H2-1 Comparative Application Example 12 D-1-2 H2-1 Comparative Application Example 13 D-1-1 H2-25 Comparative Application Example 14 D-1-2 H2-25 Comparative Application Example 15 D-1-1 H2-46 Comparative Application Example 16 D-1-2 H2-46

[0241] Performance Testing

[0242] At a brightness of 5000cd / m 2 Under the conditions of , the luminescence performance of the organic electroluminescent devices obtained in the above application examples 1 to 30 and comparative application examples 1 to 7 was tested, and the driving voltage, luminescence life and luminous efficiency were tested using a KEITHLEY 2400 measurement unit and a CS-2000 spectroradiometer. The test results are shown in Table 4:

[0243] Table 4

[0244]

[0245]

[0246] As can be seen from Table 4, the use of the luminescent compound provided in the embodiment of the present invention as the first host material of the light-emitting layer of the organic electroluminescent device in combination with a specific second host material can significantly reduce the driving voltage of the organic electroluminescent device and improve the luminous efficiency and service life of the organic electroluminescent device compared to the host materials used in the prior art.

[0247] The above description of the disclosed embodiments will enable one skilled in the art to implement or use the present invention. Various modifications to these embodiments will be readily 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 is not limited to the embodiments shown herein but is to be construed in the widest manner consistent with the principles and novel features disclosed herein.

Claims

1. A compound, characterized in that The compound is selected from any one of the following formulae:

2. An organic electroluminescent device, characterized in that: comprising an anode, a cathode, and an intermediate layer disposed between the anode and the cathode; The intermediate layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes a first host material and a second host material; The mass ratio of the first host material to the second host material is (1-99):(99-1); The first host material comprises the compound of claim 1; The structural formula of the second host material is selected from any one of the following formulas (H-2-1) to (H-2-145):

3. The organic electroluminescent device according to claim 2, characterized in that: The light-emitting layer further includes a dopant; The dopant includes a fluorescent dopant and / or a phosphorescent dopant; The mass ratio of the main material to the dopant is (90-99.5):(0.5-10).

4. The organic electroluminescent device according to claim 2, characterized in that: The intermediate layer further comprises a functional layer; The functional layer includes any one or more of a hole injection layer, a hole transport layer, a hole injection-hole transport functional layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron transport-electron injection functional layer.

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