Organic electroluminescent compound and organic electroluminescent device containing the same

Abstract

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device as shown in formula I. The present invention provides an organic electroluminescent compound applied to an organic electroluminescent device, which has the characteristics of low driving voltage and high luminous efficiency.

Description

Technical Field

[0001] The invention relates to the field of organic electroluminescent devices, and in particular to an organic electroluminescent compound and application thereof and an organic electroluminescent device. Background Art

[0002] In 1987, Tang et al. of Kodak Company prepared a double-layer organic electroluminescent diode by vacuum evaporation, using aromatic diamine as the hole transport layer and 8-hydroxyquinoline aluminum as the light-emitting layer. The driving voltage was less than 10V, the luminous efficiency was 1.5lm / W, and the luminous brightness was as high as 1000cd / m 2 This makes organic light-emitting devices (OLED) practical. OLED has the characteristics of simple structure, low driving voltage, and flexible display, and has received extensive attention in the field of optoelectronic devices and flat panel displays. After continuous development, OLED technology has now been commercialized in fields such as flat panel displays and solid-state lighting.

[0003] However, organic electroluminescent devices or screens still have problems with high driving voltage and low luminous efficiency. Among them, blue light guest materials, especially deep blue light guest materials, are the shortcomings that affect the overall performance of OLED screens, including low exciton utilization, low color purity, and low luminous efficiency caused by concentration quenching. In order to improve these defects, on the one hand, the performance of the guest material needs to be improved, and on the other hand, the device structure and preparation process also need to be further optimized.

[0004] In OLED, the efficiency and brightness of the device are directly affected by the quality of the film. Usually, OLED can deposit a multi-layer device structure by vacuum evaporation, which is conducive to adjusting the balance of carriers in the light-emitting layer. Recently, the solution method for preparing small molecule organic light-emitting diodes has also attracted much attention. Solution methods such as spin coating and inkjet printing have simple film preparation processes, easy operation and large-scale production, and lower costs. Summary of the invention

[0005] The purpose of the present invention is to overcome the defects of low luminous efficiency and poor color purity of OLED provided by the prior art and to provide a new organic electroluminescent compound.

[0006] In order to achieve the above object, the first aspect of the present invention provides an organic electroluminescent compound having a structure shown in Formula I:

[0007]

[0008] In Formula I,

[0009] R1 to R4 are the same or different and are independently selected from hydrogen, deuterium and C1-C4 alkyl;

[0010] R5 and R6 are connected to each other to form an aliphatic ring, R7 and R8 are connected to each other to form an aliphatic ring or are independently selected from hydrogen, deuterium, C1-C4 alkyl; or, R5 and R6 are independently selected from hydrogen, deuterium and C1-C4 alkyl, R7 and R8 are connected to each other to form an aliphatic ring;

[0011] Ar1 to Ar4 are the same or different, and are each independently selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.

[0012] According to some embodiments of the present invention, the aliphatic ring is a C5-C6 aliphatic ring.

[0013] According to some embodiments of the present invention, the structure of the organic electroluminescent compound is as shown in Formula II or Formula III:

[0014]

[0015] In Formula II and Formula III,

[0016] R1 to R4 are the same or different and are independently selected from hydrogen, deuterium and C1-C4 alkyl;

[0017] Ar1 to Ar4 are the same or different, and are each independently selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.

[0018] According to some embodiments of the present invention, the structure of the organic electroluminescent compound is shown in Formula IIA, Formula IIB, Formula IIIA or Formula IIIB:

[0019]

[0020] In Formula IIA, Formula IIB, Formula IIIA and Formula IIIB,

[0021] Ar1 to Ar4 are the same or different, and are each independently selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.

[0022] According to some embodiments of the present invention, Ar1 to Ar4 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirobifluorenyl, substituted or unsubstituted substituted or unsubstituted benzo[9,10]phenanthryl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted isobenzothiophenyl, substituted or unsubstituted indolizinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted bicarbazolyl, substituted or unsubstituted azabenzo[9,10]phenanthryl, substituted or unsubstituted diazabenzo[9,10]phenanthryl, substituted or unsubstituted xanthenyl, substituted or unsubstituted azacarbazolyl, substituted or unsubstituted azadibenzofuranyl, substituted or unsubstituted azadibenzothiophenyl, substituted or unsubstituted diphenylphosphinoyl, substituted or unsubstituted triphenylsilyl and substituted or unsubstituted fluoranthenyl.

[0023] According to some embodiments of the present invention, Ar1 to Ar4 are the same or different, and are independently selected from the following groups:

[0024]

[0025]

[0026] wherein n is an integer of 1-3, such as 1, 2 or 3; each R is the same or different and is independently selected from halogen, cyano, C1-C20 alkyl, halogen-substituted C1-C20 alkyl, C1-C20 alkoxy, wherein R' is a C1-C6 alkyl group, and m is an integer of 1-3, such as 1, 2 or 3.

[0027] According to some embodiments of the present invention, Ar1 to Ar4 are the same or different, and are independently selected from the following groups:

[0028]

[0029] wherein each R is the same or different and is independently selected from halogen, cyano, C1-C20 alkyl, halogen-substituted C1-C20 alkyl, C1-C20 alkoxy, Wherein R' is a C1-C6 alkyl group, and m is an integer of 1-3.

[0030] According to some embodiments of the present invention, the structure of the organic electroluminescent compound is as shown in Formula IIA-1, IIA-2 or IIA-3:

[0031]

[0032] wherein n is an integer of 1-3, such as 1, 2 or 3; each R is the same or different and is independently selected from halogen, cyano, C1-C20 alkyl, halogen-substituted C1-C20 alkyl, C1-C20 alkoxy, wherein R' is a C1-C6 alkyl group, and m is an integer of 1-3, such as 1, 2 or 3.

[0033] According to some embodiments of the present invention, the structure of the organic electroluminescent compound is as shown in Formula IIA-11, IIA-12, IIA-21 or IIA-31:

[0034]

[0035] Wherein, R is selected from halogen, cyano, C1-C20 alkyl, halogen-substituted C1-C20 alkyl, C1-C20 alkoxy, Wherein R' is a C1-C6 alkyl group, and m is an integer of 1-3.

[0036] According to some embodiments of the present invention, the structure of the organic electroluminescent compound is as shown in Formula IIB-1 or IIB-2:

[0037]

[0038] wherein n is an integer of 1-3, such as 1, 2 or 3; each R is the same or different and is independently selected from halogen, cyano, C1-C20 alkyl, halogen-substituted C1-C20 alkyl, C1-C20 alkoxy, wherein R' is a C1-C6 alkyl group, and m is an integer of 1-3, such as 1, 2 or 3.

[0039] According to some embodiments of the present invention, the structure of the organic electroluminescent compound is shown in Formula IIB-11, Formula IIB-12, Formula IIB-21, Formula IIB-31 or Formula IIB-41:

[0040]

[0041] Wherein, R is selected from halogen, cyano, C1-C20 alkyl, halogen-substituted C1-C20 alkyl, C1-C20 alkoxy, and Wherein R' is a C1-C6 alkyl group, and m is an integer of 1-3.

[0042] According to some embodiments of the present invention, the structure of the organic electroluminescent compound is as shown in Formula IIIA-1, IIIA-2 or IIIA-3:

[0043]

[0044] wherein n is an integer of 1-3, such as 1, 2 or 3; each R is the same or different and is independently selected from halogen, cyano, C1-C20 alkyl, halogen-substituted C1-C20 alkyl, C1-C20 alkoxy, wherein R' is a C1-C6 alkyl group, and m is an integer of 1-3, such as 1, 2 or 3.

[0045] According to some embodiments of the present invention, the structure of the organic electroluminescent compound is as shown in Formula IIIA-11, IIIA-21, IIIA-22 or IIIA-31:

[0046]

[0047] wherein each R is the same or different and is independently selected from halogen, cyano, C1-C20 alkyl, halogen-substituted C1-C20 alkyl, C1-C20 alkoxy, wherein R' is a C1-C6 alkyl group, and m is an integer of 1-3, such as 1, 2 or 3.

[0048] According to some embodiments of the present invention, the structure of the organic electroluminescent compound is as shown in Formula IIIB-1, IIIB-2, IIIB-3, IIIB-4, IIIB-5 or IIIB-6:

[0049]

[0050] Wherein, n is an integer from 1 to 3, such as 1, 2 or 3;

[0051] Each R is the same or different and is independently selected from halogen, cyano, C1-C20 alkyl, halogen-substituted C1-C20 alkyl, C1-C20 alkoxy, wherein R' is a C1-C6 alkyl group, and m is an integer of 1-3, such as 1, 2 or 3.

[0052] According to some embodiments of the present invention, the structure of the organic electroluminescent compound is as shown in Formula IIIB-11, IIIB-21, IIIB-31, IIIB-41, IIIB-51 or IIIB-61:

[0053]

[0054]

[0055] wherein each R is the same or different and is independently selected from halogen, cyano, C1-C20 alkyl, halogen-substituted C1-C20 alkyl, C1-C20 alkoxy, wherein R' is a C1-C6 alkyl group, and m is an integer of 1-3, such as 1, 2 or 3.

[0056] According to some embodiments of the present invention, R is selected from halogen, cyano, C1-C15 alkyl, halogen-substituted C1-C15 alkyl, C1-C15 alkoxy, Wherein R' is a C1-C4 alkyl group, and m is an integer of 1-3.

[0057] According to some embodiments of the present invention, R is selected from halogen, cyano, C1-C3 alkyl, C4-C8 alkyl, C9-C10 alkyl, halogen-substituted C1-C6 alkyl, C1-C3 alkoxy, C4-C8 alkoxy, C9-C10 alkoxy, Wherein R' is methyl or ethyl, and m is 1, 2 or 3.

[0058] According to some embodiments of the invention, R is selected from fluorine, chlorine, bromine, iodine or trifluoromethyl.

[0059] According to some embodiments of the present invention, R is selected from C1-C3 alkyl, such as methyl, ethyl, n-propyl or isopropyl.

[0060] According to some embodiments of the invention, R is selected from C4-C8 alkyl, such as n-butyl, tert-butyl, isobutyl, n-pentyl, isopentyl, n-hexyl, isohexyl, n-heptyl and n-octyl.

[0061] According to some embodiments of the present invention, R is selected from C9-C10 alkyl, such as n-nonyl or n-decyl.

[0062] According to some embodiments of the invention, R is selected from C1-C3 alkoxy, such as methoxy, ethoxy, n-propoxy or isopropoxy.

[0063] According to some embodiments of the invention, R is selected from C4-C8 alkoxy, such as n-butoxy, tert-butoxy, isobutoxy, n-pentoxy, isopentoxy, n-hexoxy, isohexoxy, 2-ethylhexyloxy, n-heptyloxy and n-octyloxy.

[0064] According to some embodiments of the present invention, R is selected from C9-C10 alkoxy, such as n-nonyloxy or n-decyloxy.

[0065] According to some embodiments of the present invention, R is selected from R' is methyl or ethyl.

[0066] According to some embodiments of the present invention, R is selected from Wherein R' is methyl or ethyl, and m is 1 or 2.

[0067] In the present invention, the asterisk * on each group indicates the connection point between the group and other parts.

[0068] Unless otherwise indicated, in the present invention, term " aryl " refers to a polyunsaturated aromatic hydrocarbon substituent, which can be a monocyclic or polycyclic (preferably 1 to 3 rings), which are fused together or covalently linked.Term " heteroaryl " refers to a 5-14 yuan monocyclic-or bicyclic-or fused polycyclic-ring system with 1 to 8 heteroatoms selected from N, O, S or Se.Term " heteroaryl " also refers to a group in which a heteroaromatic ring is fused to one or more aryl, alicyclic or heterocycloalkyl rings, wherein the group or connection point is on a heteroaromatic ring.Non-limiting examples of aryl and heteroaryl include phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl etc.

[0069] Unless otherwise specified, the term "aliphatic ring" in the present invention refers to an alicyclic hydrocarbon having 3 to 10 carbon atoms, which may be a saturated alicyclic hydrocarbon (e.g., cycloalkane) and an unsaturated alicyclic hydrocarbon (e.g., cycloalkene and cycloalkyne). Non-limiting examples of alicyclic rings include cyclobutane, cyclopentane, cyclohexane, adamantyl, and the like.

[0070] The compounds provided by the present invention can be specifically selected from any one or more of the following compounds:

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] The present invention has at least the following specific advantages:

[0086] 1. The parent nucleus of the organic compound provided by the present invention is pyrene cyclopentane and cyclohexane / cyclopentane. Pyrene itself has excellent planarity and a high radiation transition rate, and is suitable for being a luminescent material. The addition of two cyclopentanes increases the rigidity of pyrene, and can effectively reduce vibration consumption relative to the parent pyrene, thereby reducing the half-peak width of the organic compound and improving the color purity of the organic compound on the one hand; on the other hand, it can also effectively improve the fluorescence quantum efficiency of the compound; on the basis of adding two cyclopentanes, two cyclohexanes / cyclopentanes are added, and there is an angle between the cyclohexane / cyclopentane and the pyrene five-membered ring, which mainly reduces the vibration consumption and increases the spatial structure of the organic compound, weakens the quenching effect of the dye concentration, and can increase the luminous efficiency when applied to an organic electroluminescent device.

[0087] 2. The organic compound provided by the present invention contains aromatic amine derivatives, which belong to chromophores, and the amine derivatives are on both sides of the mother nucleus, which increases the spatial structure of the organic compound and weakens the quenching effect of the dye concentration;

[0088] 3. The branched-chain substituted aromatic amine derivatives of the present invention increase the solubility of the compound.

[0089] 4. The half-width of the organic compound provided by the present invention is relatively narrow, which can improve the light extraction efficiency of the top-emitting device using the compound, thereby significantly improving the overall performance of the device without changing the electrical performance of the device.

[0090] 5. Furthermore, when the aforementioned organic compound of the present invention is applied to a device, it can reduce the current density and increase the life of the device while ensuring a certain brightness.

[0091] 6. The parent structure of the pyrene cyclopentane and cyclohexane / cyclopentane of the present invention has better solubility in conventional organic solvents than pyrene itself due to the presence of multiple aliphatic rings, and the corresponding derivatives also have better solubility. Further, through the substitution of polyethylene glycol chains or aliphatic chains, its organic solvent solubility can be further improved. Therefore, it can be effectively applied to solution-processed OLED systems and maintain the luminous efficiency to the maximum.

[0092] The second aspect of the present invention provides use of the organic electroluminescent compound described in the first aspect in an organic electroluminescent device.

[0093] Preferably, the compound is present in the light-emitting layer of the device.

[0094] Further preferably, the compound is a guest material in the light-emitting layer of the device.

[0095] A third aspect of the present invention provides an organic electroluminescent device, wherein the device contains at least one of the organic electroluminescent compounds.

[0096] The organic electroluminescent device comprises an anode, 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 a cathode which are stacked in sequence.

[0097] According to some embodiments of the present invention, the organic electroluminescent device includes an anode, a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode which are stacked in sequence.

[0098] According to some embodiments of the present invention, the organic electroluminescent device includes an anode, 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 a cathode stacked in sequence.

[0099] According to some embodiments of the present invention, the organic electroluminescent device includes an anode, a hole injection layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode which are stacked in sequence.

[0100] According to some embodiments of the present invention, the anode material forming the anode is generally preferably a material with a large work function. For example, the anode material used in the present invention is selected from one or more of the following materials: metals, such as vanadium, chromium, copper and gold, or other alloys: metal oxides, such as zinc oxide, indium oxide, indium tin oxide, indium zinc oxide and tin dioxide, combinations of metals and oxides, such as zinc oxide: aluminum, but not limited thereto.

[0101] According to some embodiments of the present invention, the material forming the hole injection layer has the ability to transport holes, so the material of the hole injection layer has the effect of injecting holes into the anode, has an excellent hole injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and has excellent thin film forming ability. The HOMO of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.

[0102] According to some embodiments of the present invention, the material forming the hole transport layer is a material that can receive holes from the anode or the hole injection layer, move the holes to the light emitting layer, and has high mobility for holes.

[0103] According to some embodiments of the present invention, the hole injection material and the hole transport material include at least one of aromatic amine derivatives (such as NPB, SqMA1), hexaazatriphenylene derivatives (such as HACTN), indolecarbazole derivatives, conductive polymers (such as PEDOT / PSS), phthalocyanine or porphyrin derivatives, dibenzoindenofluorene amine, and spirobifluorene amine, but are not limited thereto.

[0104] According to some embodiments of the present invention, the hole injection layer and the hole transport layer may be formed by, for example, an aromatic amine derivative of the following general formula:

[0105]

[0106] The groups R1 to R9 in the above general formula are each independently selected from a single bond, hydrogen, deuterium, alkyl, benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, dimethylfluorene, spirobifluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolecarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine.

[0107] According to some embodiments of the present invention, the material for forming the electron blocking layer is not particularly limited. Generally, compounds that meet the first and / or second conditions below can be considered for use:

[0108] First: It has a shallower LUMO energy level (smaller absolute value), the purpose of which is to reduce the number of electrons leaving the light-emitting layer, thereby increasing the probability of electrons and holes recombining in the light-emitting layer.

[0109] Second: It has a larger triplet energy, the purpose of which is to reduce the number of excitons leaving the light-emitting layer, thereby increasing the efficiency of exciton conversion to luminescence.

[0110] According to some embodiments of the present invention, the materials forming the electron blocking layer include but are not limited to aromatic amine derivatives (such as NPB) and spirobifluorenamine (such as SpMA2), wherein some electron blocking materials have structures similar to those of hole injection materials and hole transport materials.

[0111] According to some embodiments of the present invention, the light-emitting material of the light-emitting layer is a material that can emit light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer respectively and combining the holes and electrons, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence.

[0112] According to some embodiments of the present invention, the light emitting layer may include a host material and a guest material.

[0113] According to some embodiments of the present invention, the host material may include anthracene derivatives, carbazole derivatives, fluorene derivatives, aromatic amine derivatives, silicone derivatives, carbazole-triazine derivatives, phosphorus-oxygen derivatives, and phenanthroline derivatives, but is not limited thereto.

[0114] In some preferred embodiments of the present invention, the anthracene derivative has the general formula shown below:

[0115]

[0116] The phosphorus-oxygen derivatives have the general formula shown below:

[0117]

[0118] In the general formula of the above-mentioned anthracene derivatives and phosphine-oxy derivatives, R11, R12, R13, R14, R15 and R16 are each independently selected from a single bond, hydrogen, deuterium, alkyl, benzene, diphenyl, terphenyl, quaterphenyl, naphthalene, phenylnaphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolecarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine, and groups represented by their substituents.

[0119] According to some embodiments of the present invention, the guest material is the compound described in the first aspect.

[0120] According to some embodiments of the present invention, the material of the hole blocking layer may also preferably be a compound having the following first and / or second conditions:

[0121] First: It has a deeper HOMO energy level (larger absolute value), the purpose of which is to reduce the number of holes leaving the light-emitting layer, thereby increasing the probability of electrons and holes recombining in the light-emitting layer.

[0122] Second: It has a larger triplet energy, the purpose of which is to reduce the number of excitons leaving the light-emitting layer, thereby increasing the efficiency of exciton conversion to luminescence.

[0123] According to some embodiments of the present invention, the material forming the hole blocking layer may include, for example, phenanthroline derivatives (eg, Bphen, BCP), triphenylene derivatives, benzimidazole derivatives, but is not limited thereto.

[0124] According to some embodiments of the present invention, the electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the hole injection layer, and also has excellent film forming ability. The electron injection layer material includes, for example, LiF, CsF, Cs2CO3, LiQ, but is not limited thereto.

[0125] According to some embodiments of the present invention, the cathode material is preferably formed of a material with a small work function, which can smoothly inject electrons into the organic material layer. The cathode material that can be used in the present disclosure can be selected from one or more of the following materials, one or more of Al, Mg and Ag.

[0126] According to some embodiments of the present invention, the organic electroluminescent device of the present invention is preferably coated with one or more layers by means of vacuum evaporation. Before vacuum coating, the materials of different functional layers are placed in an evaporation boat and vacuumed using a mechanical pump to a vacuum degree of 10 -3 Pa or less, preferably less than 10 -4 Below Pa, vacuum evaporation of organic thin films begins. After sublimation by heating in a vacuum, small organic molecules detach from the material surface at a certain initial velocity and fly outward, moving to the surface of the substrate, cooling and depositing to form a thin film. Multiple layers are evaporated according to the above-mentioned vacuum coating method. During the thin film deposition process, a quartz crystal oscillator is used to monitor the film deposition thickness and rate on the substrate in real time.

[0127] According to some embodiments of the present invention, the organic electroluminescent device of the present invention is preferably a solution method, that is, the organic compound of the present invention is formulated into a solution, and a layer or a plurality of layer structures are formed by spin coating or by means of any printing method, such as screen printing, flexographic printing, inkjet printing, lithography. However, when multiple layers are made in this way, damage between layers is likely to occur, that is, when one layer is made, when another layer is made with a solution, the solvent in the solution will destroy the already formed layer, which is not conducive to device production. The organic compound provided by the present invention can be substituted by structural modification, so that the organic compound of the present invention undergoes cross-linking under heating or ultraviolet exposure, thereby maintaining a complete layer without being destroyed. The organic compound of the present invention can also be applied from a solution and fixed in the corresponding layer by subsequent cross-linking in a polymer network.

[0128] In some preferred embodiments of the present invention, the organic electroluminescent device of the present invention is manufactured by applying one or more layers from solution and applying one or more layers by a sublimation method.

[0129] According to some embodiments of the present invention, the preferred solvent for preparing the organic electroluminescent device of the present invention is selected from toluene, anisole, o-xylene, m-xylene, p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, THF, methyl-THF, THP, chlorobenzene, phenoxytoluene, in particular 3-phenoxytoluene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole , acetophenone, benzothiazole, butyl benzoate, isopropanol, isopropylbenzene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, methyl benzoate, NMP, p-methylisobenzoene, phenethyl ether, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dibutyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-heptanol, 3-heptanol, or a mixture of these solvents. DETAILED DESCRIPTION

[0130] The endpoints and any values ​​of the ranges disclosed in this article are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of each range, the endpoint values ​​of each range and the individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed in this article.

[0131] The present invention has no particular restrictions on the specific method for preparing the aforementioned compounds. Those skilled in the art can obtain the aforementioned compounds of the present invention according to the specific structural formula provided by the present invention in combination with the conventional process route in the field of organic synthesis, and the present invention hereinafter exemplarily lists several examples to illustrate the preparation method of the compounds of the present invention. Those skilled in the art can also obtain the specific preparation method of all the remaining compounds by replacing the type of raw materials according to the preparation method of the compounds in the following text of the present invention. The present invention no longer describes the preparation methods of all compounds in detail, and those skilled in the art should not be construed as limiting the present invention.

[0132] The present invention will be described in detail below by way of examples. In the following examples, unless otherwise specified, all the raw materials used are common commercial products. Unless otherwise specified, the room temperature described below means 25±1°C.

[0133] Preparation Example 1: Synthesis of Intermediate M1

[0134]

[0135] Synthesis of intermediate M1-1: In a 1L three-necked flask, 1,6-dibromopyrene (0.12 mol), 1-cyclohexeneboronic acid (0.24 mol), a mixed solution of toluene (300 ml) ethanol (200 ml) and water (100 ml), sodium carbonate (0.6 mol), tetrakis(triphenylphosphine)palladium (2.4 mmol) were added in sequence, and heated and stirred under nitrogen protection, and the temperature was raised to reflux. After 6 hours of reaction, the reaction was basically completed by HPLC detection. Deionized water (600 ml) was added to the reaction solution, stirred for 10 minutes, and the organic phase was washed three times with toluene solvent, the organic phases were combined, dried with anhydrous magnesium sulfate, the desiccant was filtered, the organic solvent was dried, and the residue was separated by silica gel column to obtain white intermediate M1-1 (yield: 76%).

[0136] Synthesis of intermediate M1-2: In a 500ml three-necked flask, add intermediate M1-1 (0.09mol), 1,2-dichloromethane (320ml), cool to 0°C, add trifluoromethanesulfonic acid (30ml) dropwise, after the addition is complete, heat and stir under nitrogen protection, raise the temperature to reflux, react for 5h, and HPLC detects that the raw material is basically reacted. Cool to room temperature, add sodium bicarbonate aqueous solution to adjust the solution to neutrality, dry with anhydrous magnesium sulfate, filter the desiccant, spin dry the organic solvent, and separate the residue through a silica gel column to obtain a white intermediate M1-2 (yield: 90%).

[0137] Synthesis of intermediate M1: In a 1L three-necked flask, add intermediate M1-2 (0.08 mol) and 1,2-dichloromethane (290 ml), stir to dissolve, cool to 0°C in an ice-water bath, slowly add NBS (0.16 mol), continue stirring for 45 hours after the addition is complete, TLC detection shows that the reaction is basically complete, and add sodium thiosulfate aqueous solution to quench the reaction. Add deionized water (300 ml), separate the organic phase, wash three times with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, filter the desiccant, and decompress and spin-dry the solvent to obtain a white solid. This solid is recrystallized twice from chloroform to obtain a white solid M1 (yield: 78%).

[0138] Mass spectrum: C28H24Br2, theoretical value: 518.02, found value: 518.2. Elemental analysis: theoretical value: C: 64.64%, H: 4.65%; found value: C: 64.67%, H: 4.68%.

[0139] Preparation Example 2: Synthesis of Intermediate M2

[0140]

[0141] Synthesis of intermediate M2: In a 500ml three-necked flask, add intermediate M1 (5.2g, 0.01mol), D6-DMSO (99% deuterated rate, 70ml), potassium tert-butoxide (1.1mol), under nitrogen protection, heat and stir, raise the temperature to reflux, react for 20h, and the reaction is basically complete when detected by HPLC. Cool to room temperature, add deionized water (60ml) and stir for 10min, extract the organic phase with dichloromethane three times, combine the organic phases, dry with anhydrous magnesium sulfate, filter the desiccant, decompress and spin-dry the solvent, and recrystallize to obtain a white solid (yield: 86%) with a deuterated rate of about 99%.

[0142] Mass spectrum: C28H20D4Br2, theoretical value: 522.05, found value: 522.1.

[0143] Preparation Example 3: Synthesis of Intermediate M3

[0144]

[0145] Synthesis of intermediate M3-1: The synthesis method is the same as that of intermediate M1-1 to obtain white solid M3-1 (yield: 82%).

[0146] Synthesis of intermediate M3-2: The synthesis method is the same as that of intermediate M1-2 to obtain white solid M3-2 (yield: 93%).

[0147] Synthesis of intermediate M3: The synthesis method is the same as that of intermediate M1 to obtain white solid M3 (yield: 76%).

[0148] Mass spectrum: C26H20Br2, theoretical value: 489.99, found value: 490.1. Elemental analysis: theoretical value: C: 63.44%, H: 4.10%; found value: C: 63.47%, H: 4.12%.

[0149] Preparation Example 4: Synthesis of Intermediate M4

[0150]

[0151] Synthesis of intermediate M4: The synthesis method is the same as that of intermediate M2, and white solid M4 is obtained (yield 88%) with a deuteration rate of about 98%.

[0152] Mass spectrum: C26H16D4Br2, theoretical value: 494.02, found value: 494.1.

[0153] Preparation Example 5: Synthesis of Compound 3

[0154]

[0155] Synthesis of compound 3: In a 500ml three-necked flask, add intermediate M1 (0.06mol), di(o-toluene)amine (0.12mol), sodium tert-butoxide (0.3mol), tri(dibenzylideneacetone)dipalladium (1.2mmol), tri-tert-butylphosphine (1.2mmol) and toluene (300ml), under nitrogen protection, heat and stir, raise the temperature to reflux for 5h, and the reaction is basically complete when detected by HPLC. The reaction solution is cooled to room temperature, diluted hydrochloric acid is added thereto to adjust it to neutrality, 300ml of deionized water is added, stirred for 10min, the organic phase is washed three times with toluene solvent, dried with anhydrous magnesium sulfate, the desiccant is filtered, the solvent is dried under reduced pressure, and the residue is separated by silica gel chromatography to obtain a white solid (yield: 83%).

[0156] Mass spectrum: C56H52N2, theoretical value: 752.41, measured value: 752.5. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 1.40 ~ 1.55 (8H, m), 1.86 ~ 1.95 (4H, m), 2.12 ~ 2.15 (16H, m), 3.12 ~ 3.19 (4H, m), 6.88 ~ 6.90 (2H, m), 6.92 ~ 6.93 (1H, m), 7.10 ~ 7.12 (1H, m), 7.13 ~ 7.15 (6H, m), 7.16 ~ 7.17 (4H, m), 7.19 ~ 7.20 (2H, m), 7.71 ~ 7.72 (2H, s), 7.87 ~ 7.87 (2H, s).

[0157] Preparation Example 6: Synthesis of Compound 5

[0158]

[0159] Synthesis of compound 5: The synthesis method was the same as that of compound 3 to obtain a white solid (yield: 81%).

[0160] Mass spectrum: C64H68N2, theoretical value: 864.54, measured value: 864.5. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.18 ~ 1.19 (12H, s), 1.21 ~ 1.22 (12H, s), 1.39 ~ 1.57 (8H, m), 1.84 ~ 1.97 (4H, m), 2.10 ~ 2.22 (4H, m), 2.81 ~ 2.92 (4H, m), 3.12 ~ 3.19 (4H, m), 7.03 ~ 7.04 (3H, m), 7.06 ~ 7.07 (5H , m), 7.15~7.17 (5H, m), 7.18~7.20 (3H, m), 7.77~7.79 (2H, s), 7.90~7.91 (2H, s).

[0161] Preparation Example 7: Synthesis of Compound 27

[0162]

[0163] Synthesis of compound 27: The synthesis method was the same as that of compound 3 to obtain a white solid (yield: 78%).

[0164] Mass spectrum: C70H60N2O2, theoretical value: 960.47, found value: 960.5. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.18 ~ 1.22 (12H, d), 1.40 ~ 1.57 (8H, m), 1.83 ~ 1.97 (4H, m), 2.09 ~ 2022 (4H, m), 2.81 ~ 2.93 (2H, m), 3.12~3.20(4H,m), 7.03~7.08(4H,m), 7.15~7.21(6H,m), 7.30~7.37(2H,m), 7.38~7.4 4(6H,m), 7.52~7.57(4H,m), 7.62~7.66(2H,d), 7.96~7.98(1H,m), 7.99~8.00(1H,m).

[0165] Preparation Example 8: Synthesis of Compound 40

[0166]

[0167] Synthesis of compound 40: The synthesis method was the same as that of compound 3 to obtain a white solid (yield: 82%).

[0168] Mass spectrum: C80H68N2, theoretical value: 1056.54, measured value: 1056.6. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.39 ~ 1.58 (8H, m), 1.82 ~ 2.00 (4H, m), 2.12 ~ 2.15 (14H, m), 3.09 ~ 3.23 (4H, m), 6.87 ~ 6.89 (3H, s), 7.30 ~ 7.34 (4H, m), 7.37 ~ 7.45 (7H, m), 7.45 ~ 7.47 (4H, m), 7.48 ~ 7.53 (6H, m), 7.73 ~ 7.77 (14H, m).

[0169] Preparation Example 9: Synthesis of Compound 52

[0170]

[0171] Synthesis of compound 52: The synthesis method was the same as that of compound 3 to obtain a white solid (yield: 85%).

[0172] Mass spectrum: C64H64D4N2, theoretical value: 868.56, measured value: 868.6. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.34~1.60 (8H, m), 1.91~2.06 (4H, m), 2.10~2.14 (24H, m), 2.24~2.36 (16H, m), 6.72~6.75 (8H, S), 6.63~6.65 (2H, S), 7.78~7.81 (2H, S).

[0173] Preparation Example 10: Synthesis of Compound 96

[0174]

[0175] Synthesis of Compound 96: The synthesis method was the same as that of Compound 3 to obtain a white solid (yield: 83%).

[0176] Mass spectrum: C58H56N2, theoretical value: 780.44, measured value: 780.6. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.62~1.91 (8H, m), 2.12~2.14 (24H, m), 2.15~2.35 (4H, m), 3.76~3.91 (4H, m), 7.02~7.07 (8H, m), 7.09~7.16 (4H, m), 7.60~7.62 (2H, s), 7.71~7.73 (2H, s).

[0177] Preparation Example 11: Synthesis of Compound 110

[0178]

[0179] Synthesis of Compound 110: The synthesis method was the same as that of Compound 3 to obtain a white solid (yield: 77%).

[0180] Mass spectrum: C64H48N2O2, theoretical value: 876.37, measured value: 876.5. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 1.62 ~ 1.95 (8H, m), 2.12 ~ 2.15 (6H, s), 2.23 ~ 2.42 (4H, m), 3.89 ~ 3.97 (4H, m), 6.86 ~ 6.94 (2H, m), 7.11 ~ 7.20 (8H, m), 7.28 ~ 7.43 (4H, m), 7.52 ~ 7.57 (4H, m), 7.61 ~ 7.62 (2H, s), 7.72 ~ 7.73 (2H, s), 7.96 ~ 8.00 (2H, m), 8.02 ~ 8.04 (2H, d).

[0181] Preparation Example 12: Synthesis of Compound 136

[0182]

[0183] Synthesis of Compound 136: The synthesis method was the same as that of Compound 3 to obtain a white solid (yield: 75%).

[0184] Mass spectrum: C62H68D4N2Si4, theoretical value: 960.50, measured value: 960.6. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.62~1.92 (8H, m), 2.13~2.21 (36H, m), 2.17~2.39 (4H, m), 3.74~3.93 (4H, m), 7.02~7.06 (8H, m), 7.09~7.18 (4H, m), 7.63~7.66 (2H, s), 7.76~7.77 (2H, s).

[0185] Preparation Example 13: Synthesis of Compound 162

[0186]

[0187] Synthesis of Compound 162: The synthesis method was the same as that of Compound 3 to obtain a white solid (yield: 76%).

[0188] Mass spectrum: C76H92N2, theoretical value: 1032.73, found value: 1032.8. 1H-NMR (400MHz, CDCl3) (ppm) δ = 0.86 ~ 0.92 (12H, m), 1.21 ~ 1.65 (40H, m), 1.84 ~ 1.97 (4H, m), 2.09 ~ 2.23 (4H, m), 2.48~2.49(2H,m), 2.51~2.52(4H,m), 2.54~2.56(2H,m), 3.12~3.20(4H,m), 7.00~7.05 (8H, m), 7.15~7.20 (8H, m), 7.78~7.79 (2H, m), 7.92~7.93 (2H, s).

[0189] Preparation Example 14: Synthesis of Compound 213

[0190]

[0191] Synthesis of compound 213: The synthesis method was the same as that of compound 3 to obtain a white solid (yield: 79%).

[0192] Mass spectrum: C84H104D4N2O4, theoretical value: 1212.86, measured value: 1212.9. 1H-NMR (400MHz, CDCl3) (ppm) δ = 0.83~0.95 (12H, m), 1.23~1.55 (48H, m), 1.65~1.83 (8H, m), 1.92~2.04 (4H, m), 2.25~2.43 (4H, m), 4.06~4.16 (8H, m), 6.76~6.81 (8H, m), 7.15~7.20 (8H, m), 7.79~7.80 (2H, s), 7.92~7.93 (2H, s).

[0193] Preparation Example 15: Synthesis of Compound 284

[0194]

[0195] Synthesis of intermediate 284-1: The synthesis method is the same as that of compound 3 to obtain a white solid (yield: 75%).

[0196] Synthesis of compound 284: The synthesis method was the same as that of compound 3 to obtain a white solid (yield: 73%).

[0197] Mass spectrum: C112H140D4N2, theoretical value: 1521.16, found value: 1521.2. 1H-NMR (400MHz, CDCl3) (ppm) δ = 0.83 ~ 0.95 (20H, m), 1.19 ~ 1.37 (72H, m), 1.59 ~ 1.77 (8H, m), 1.90 ~ 2.01 (14H, m), 7.00 ~ 7.05 (4H, m), 7.16 ~ 7.22 (4H, m), 7.23~7.28 (2H, m), 7.31~7.35 (2H, m), 7.37~7.40 (2H, s), 7.42~7.45 (2H, m), 7.47~7.50 (3H, m) ), 7.61~7.62(2H,m), 7.72~7.73(2H,m), 7.84~7.85(1H,m), 7.87~7.89(1H,d), 7.91~7.92(1H,d).

[0198] Preparation Example 16: Synthesis of Comparative Compound 3

[0199]

[0200] Synthesis of Compound 3: The synthesis method is the same as that of Compound 3 to obtain a white solid (yield: 75%).

[0201] Mass spectrum: C46H36N2, theoretical value: 616.29, measured value: 616.3. 1H-NMR (400MHz, CDCl3) (ppm) δ = 2.22~2.23 (4H, m), 3.38~3.44 (8H, m), 6.96~7.04 (4H, m), 7.05~7.10 (8H, m), 7.20~7.28 (8H, m), 7.66~7.68 (2H, s), 7.95~7.96 (2H, s).

[0202] Solubility Experiment Example:

[0203] Five compounds were tested respectively: the solubility of the comparative compounds Compound 1, Compound 2 and Compound 3 and the compound 5 and compound 162 of the present invention at room temperature, to illustrate the effect of the compounds having the structural characteristics described in the present invention on the solubility improvement:

[0204]

[0205] The specific test scheme is as follows: Take 0.5g of the above five compounds respectively, add a certain amount of toluene solvent at room temperature, fully dissolve by ultrasound, and then compare the volume of the solvent used. See the table below

[0206] Compound 1 Compound 2 Compound 3 5 162 Sample volume (g) 0.5 0.5 0.5 0.5 0.5 Toluene volume (ml) 95 43 48 28 3 Solubility Very bad Poor Poor Soluble Soluble

[0207] The experimental results show that the parent structure of the present invention can significantly improve the solubility of the derivative in organic solvents. After modification with long-chain alkyl groups, the solubility can be further improved. Such solubility can ensure that the material can be well applied in the preparation of solution-processed OLED devices.

[0208] Device Example 1

[0209] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol (volume ratio 1:1), baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0210] Place the glass substrate with the anode in a vacuum chamber and evacuate to 1×10 -5 Pa, vacuum evaporating HAT-CN as a hole injection layer on the above anode layer film, the evaporation rate is 0.1nm / s, and the total evaporation film thickness is 1nm; then evaporating the hole transport layer NPB, the evaporation rate is 0.1nm / s, and the thickness is 60nm;

[0211] The electron blocking layer TCTA of the device is vacuum evaporated on the hole transport layer, with an evaporation rate of 0.1nm / s and a total evaporation film thickness of 10nm;

[0212] The light-emitting layer of the device is vacuum-evaporated on the electron blocking layer. The light-emitting layer includes a main material and a guest material. The evaporation rate of the main material ADN is adjusted to 0.1nm / s, and the evaporation rate of the guest material compound 3 is set at 5% by using a multi-source co-evaporation method. The total film thickness of the evaporation is 30nm.

[0213] The hole blocking layer TPBi of the device was vacuum-deposited on the light-emitting layer at a rate of 0.1 nm / s and a thickness of 5 nm. Then, the electron transport layer was evaporated. The evaporation rates of ET-1 and ET-2 were adjusted to 0.1 nm / s by using a multi-source co-evaporation method, and the total evaporation film thickness was 30 nm.

[0214] LiF with a thickness of 0.5 nm was vacuum-evaporated on the electron transport layer (ETL) as an electron injection layer, and an Al layer with a thickness of 150 nm was used as the cathode of the device.

[0215] Device Examples 2-18

[0216] Organic light-emitting devices of device examples 2 to 18 were prepared by a method similar to that of device example 1, except that compound 3 in device example 1 was replaced with a compound shown in Table 1.

[0217] The molecular structures involved are as follows:

[0218]

[0219] Device Comparative Example 1-Comparative Example 3

[0220] An organic electroluminescent device of Device Comparative Example 1 was prepared by a method similar to that of Device Example 1, except that Compound 3 in Device Example 1 was replaced by Compound 1, Compound 2 and Compound 3, respectively.

[0221] Test Example 1

[0222] At brightness 1000cd / m 2 The driving voltage, current efficiency, half-peak width and color coordinates of the organic electroluminescent devices prepared in device examples 1-18 and device comparative examples 1-3 were measured. The results are shown in Table 1.

[0223] Table 1

[0224]

[0225] The above results show that the organic compound of the present invention is applied to the organic electroluminescent device, and compared with the comparative example, the half-peak width is narrower, so the device has better color purity, higher device luminous efficiency and lower driving voltage.

[0226] Device Example 19

[0227] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol (volume ratio 1:1), baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0228] PEDOT:PSS (CLEVIOS VP AI4083) was spin-coated on a glass substrate with ITO at a speed of 3000 r / min in air for 60 s, and then annealed at 120° C. for 10 min in a glove box to a thickness of 60 nm.

[0229] In a glove box, toluene was used as the solvent, the main material ADN with a solubility of 10 mg / mL and doped with 6% mass fraction of compound 162 as the light-emitting layer, and was spin-coated on the ITO / PEDOT:PSS substrate at a speed of 3000 r / min for 60 seconds and annealed at 90°C for 30 minutes to remove the residual organic solvent. The light-emitting layer was 40 nm.

[0230] The above-mentioned ITO / PEDOT:PSS / ADN:6% compound 162 substrate was placed in a vacuum chamber and evacuated to 1×10 - 5 Pa, vacuum evaporate the hole blocking layer TPBi of the device on the light-emitting layer, the evaporation rate is 0.1nm / s, and the thickness is 5nm; then evaporate the electron transport layer, using the multi-source co-evaporation method, adjust the evaporation rate of ET-1 and ET-2 to 0.1nm / s, and the total evaporation film thickness is 30nm;

[0231] LiF with a thickness of 0.5 nm was vacuum-evaporated on the electron transport layer (ETL) as an electron injection layer, and an Al layer with a thickness of 150 nm was used as the cathode of the device.

[0232] Device Examples 20-22

[0233] Organic light-emitting devices of device examples 20 to 22 were prepared by a method similar to that of device example 19, except that compound 162 in device example 8 was replaced by the compounds shown in Table 2.

[0234] Device Comparison Examples 4-5

[0235] Organic electroluminescent devices of device comparison examples 4-5 were prepared by a method similar to that of device example 19, except that compound 162 in device example 19 was replaced by compound 1 and compound 2, respectively.

[0236] Test Example 2

[0237] At brightness 1000cd / m 2 The driving voltage, current efficiency, half-peak width and color coordinates of the organic electroluminescent devices prepared in device examples 19-22 and device comparative examples 4-5 were measured. The results are shown in Table 2.

[0238] Table 2

[0239]

[0240] The above results show that the organic compound of the present invention is applied to an organic electroluminescent device. Compared with the comparative example, due to the increase in solubility, the light-emitting layer formed by the solution process is not prone to uneven precipitation of the light-emitting material, and a uniform and high-quality thin film can be obtained, thereby ensuring the photoelectric performance of the device. In addition, consistent with the above-mentioned evaporation method, the half-peak width is narrow, so that the device has better color purity, and at the same time has a higher device luminous efficiency and a lower driving voltage.

[0241] The preferred embodiments of the present invention are described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, the technical solution of the present invention can be subjected to a variety of simple modifications, including the combination of various technical features in any other suitable manner, and these simple modifications and combinations should also be regarded as the contents disclosed by the present invention and belong to the protection scope of the present invention.

Claims

1. An organic electroluminescent compound represented by formula II or formula III: In Formula II and Formula III, R1 to R4 are the same or different and are independently selected from hydrogen, deuterium and C1-C4 alkyl; Ar1 to Ar4 are the same or different and are independently selected from the following groups: in, n is an integer from 1 to 3; Each R is the same or different and is independently selected from halogen, cyano, C1-C20 alkyl, halogen-substituted C1-C20 alkyl, C1-C20 alkoxy, Wherein R' is a C1-C6 alkyl group, and m is an integer of 1-3.

2. The organic electroluminescent compound according to claim 1, characterized in that Ar1 to Ar4 are the same or different and are independently selected from the following groups: wherein each R is the same or different and is independently selected from halogen, cyano, C1-C20 alkyl, halogen-substituted C1-C20 alkyl, C1-C20 alkoxy, Wherein R' is a C1-C6 alkyl group, and m is an integer of 1-3.

3. The organic electroluminescent compound according to claim 1 or 2, characterized in that: The structure of the organic electroluminescent compound is shown in Formula IIA, Formula IIB, Formula IIIA or Formula IIIB: In Formula IIA, Formula IIB, Formula IIIA and Formula IIIB, Ar1 to Ar4 are as defined in claim 1 or 2.

4. The organic electroluminescent compound according to claim 1 or 2, characterized in that: Each R is the same or different and is independently selected from halogen, cyano, C1-C15 alkyl, halogen-substituted C1-C15 alkyl, C1-C15 alkoxy, Wherein R' is a C1-C4 alkyl group, and m is an integer of 1-3.

5. The organic electroluminescent compound according to claim 1 or 2, characterized in that: Each R is the same or different and is independently selected from halogen, cyano, C1-C3 alkyl, C4-C8 alkyl, C9-C10 alkyl, halogen-substituted C1-C6 alkyl, C1-C3 alkoxy, C4-C8 alkoxy, C9-C10 alkoxy, Wherein R' is methyl or ethyl, and m is 1, 2 or 3.

6. The organic electroluminescent compound according to claim 1 or 2, characterized in that: Selected from the following compounds:

7. Use of the organic electroluminescent compound according to any one of claims 1 to 6 in an organic electroluminescent device.

8. An organic electroluminescent device comprising the organic electroluminescent compound according to any one of claims 1 to 6.

9. The organic electroluminescent device according to claim 8, characterized in that: The organic electroluminescent compound is present in the light-emitting layer of the organic electroluminescent device.

10. The organic electroluminescent device according to claim 9, characterized in that: The organic electroluminescent compound serves as a guest material in the light-emitting layer.

11. The organic electroluminescent device according to claim 8, characterized in that: It contains an anode, a hole injection layer, an optional hole transport layer, an optional electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode.

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