Organic compound, application thereof and organic electroluminescent device

Abstract

The invention discloses an organic compound, application thereof and an organic electroluminescent device, and relates to the technical field of organic electroluminescent materials, the structural formula of the organic compound is as shown in the formula I: # imgabs0 # in the formula I, Ar1 is selected from aryl with the carbon atom number of 6-24 and heteroaryl with the carbon atom number of 5-24, and Ar2 is selected from aryl with the carbon atom number of 6-24 and heteroaryl with the carbon atom number of 5-24; ar2 is selected from aryl with the carbon atom number of 10-24 and heteroaryl with the carbon atom number of 7-24; r1-R16 are the same or different and are respectively and independently selected from hydrogen, deuterium, alkyl with the carbon atom number of 1-10, cycloalkyl with the carbon atom number of 3-10, cyano, fluorine atoms, aryl with the carbon atom number of 6-12 or heteroaryl containing a first heteroatom, wherein the first heteroatom is selected from an oxygen atom and a sulfur atom; the hydrogen in the organic compound may be substituted by deuterium. The organic compound enables the organic electroluminescent device to have low voltage, long service life and high efficiency.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescent materials, and in particular to an organic compound and its use, and an organic electroluminescent device. Background Art

[0002] Organic light-emitting diodes (OLEDs) have high-brightness solid-state light emission and can be made into various flexible displays, so they have attracted much attention. Blue fluorescent light-emitting devices are widely used because of their good light emission life. Since anthracene has high fluorescence quantum efficiency, suitable triplet and singlet energy levels, it can make good use of triplet and singlet energy and has high luminous efficiency. Therefore, blue fluorescent light-emitting host materials based on anthracene are widely used in OLED devices.

[0003] Among them, compounds in which phenanthrene is connected to anthracene at the 9-position are also widely used in OLED devices. However, a common problem with this type of device is that the voltage is too high. Summary of the invention

[0004] The purpose of the present application is to enable an organic electroluminescent device to have low voltage, long life and high efficiency.

[0005] To achieve the above objectives, this application provides the following technical solutions:

[0006] The first aspect of the present application provides an organic compound, whose structural formula is shown in Formula I:

[0007]

[0008] In Formula I, Ar1 is selected from an aryl group having 6 to 24 carbon atoms and a heteroaryl group having 5 to 24 carbon atoms; Ar2 is selected from an aryl group having 10 to 24 carbon atoms and a heteroaryl group having 7 to 24 carbon atoms; R1 to R 16 The same or different and each independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cyano group, a fluorine atom, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group containing a first heteroatom, wherein the first heteroatom is selected from an oxygen atom and a sulfur atom; the hydrogen in the organic compound may be replaced by deuterium, and the organic compound does not contain:

[0009] The second aspect of the present application provides use of the above-mentioned organic compound in preparing an organic electroluminescent device.

[0010] A third aspect of the present application provides an organic electroluminescent device, comprising a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer comprises the above-mentioned organic compound.

[0011] The organic compound of the present application is connected to an anthracene group at the 9-position of the phenanthryl group, and is substituted with an aryl or heteroaryl group of suitable size at the 10-position of the phenanthrene group. The substituent at the 10-position can produce a spatial conjugation effect of suitable size with the anthracene group, so that the conjugation center of the anthracene group changes, thereby effectively improving the hole mobility of the organic compound, thereby reducing the device voltage. At the same time, the organic compound also has high rotation resistance and good stability, so that the device can also have both high efficiency and long life. BRIEF DESCRIPTION OF THE DRAWINGS

[0012] The following drawings describe in detail the exemplary embodiments disclosed in this application. The same reference numerals represent similar structures in several views of the drawings. Those skilled in the art will understand that these embodiments are non-limiting, exemplary embodiments, and the drawings are only used for the purpose of illustration and description, and are not intended to limit the scope of this application. Other embodiments may also accomplish the inventive intent in this application. It should be understood that the drawings are not drawn to scale. Among them:

[0013] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device prepared in Example 16 of the present application. DETAILED DESCRIPTION

[0014] The following description provides specific application scenarios and requirements of the present application, with the purpose of enabling those skilled in the art to make and use the content in the present application. It will be apparent to those skilled in the art that various local modifications to the disclosed embodiments are apparent, and the general principles defined herein may be applied to other embodiments and applications without departing from the spirit and scope of the present application. Therefore, the present application is not limited to the embodiments shown, but to the widest scope consistent with the claims.

[0015] Compared with naphthyl and other groups, the structure of phenanthryl is more stable. In addition, when a ring structure is formed on phenanthrene, e.g. Due to the high tension of the ring structure, the stability of the molecule is not as good as that of phenanthrene. Therefore, when the compound connected with phenanthrene and anthracene is applied to OLED devices, the device life can be improved. With anthracene has higher rotational resistance energy, can preferably prevent the free rotation of molecules, make molecular energy reduction, so that device has high efficiency.But, because the planarity of anthracene is better, electron fully conjugated delocalization, therefore the hole mobility of compound is very poor.Meanwhile, after phenanthrene 9 position is connected with anthracene, cause the dihedral angle of phenanthrene plane and anthracene plane to be large (close to 90 degree), make phenanthrene base can not produce large influence to the conjugated delocalization of anthracene base, therefore make phenanthrene 9 position and the compound connected with anthracene have the problem of high voltage generally.

[0016] Compared with the compound in which phenanthrene is connected to anthracene at the 9 position, the voltage of the compound in which phenanthrene is connected to anthracene at the 2 or 3 position will be reduced by 0.2 to 0.4 V, but the efficiency will also be lower. There are also some phenanthrene derivatives, such as phenanthrene connected to anthracene at the 4 or 5 position through oxygen atoms, Sp3 carbon atoms, etc., which are far less stable than phenanthrene. There are also some compounds, such as The voltage was lowered by introducing a heteroatom at the 10-position of phenanthrene.

[0017] Significantly different from the above scheme, the inventors of the present application proposed for the first time that on the basis of connecting phenanthrene at position 9 to anthracene, the voltage can be reduced by generating a spatial conjugation effect between the substituent at position 10 of phenanthrene and anthracene. Specifically, by substituting a group of suitable size at position 10 of phenanthrene, a spatial conjugation effect is formed between the phenanthrene and anthracene, so that the conjugation center of anthracene changes, thereby improving the hole mobility of the compound, thereby effectively reducing the device voltage. Moreover, the inventors of the present application were pleasantly surprised to find that the device can also have both high efficiency and long life.

[0018] The following is a detailed description of some terms that appear in this application:

[0019] Substituted or unsubstituted: refers to being substituted with one or more substituents, or being unsubstituted. If not otherwise specified, the substituents in the case of substitution may be selected from the following: deuterium, halogen, fluorine, trifluoromethyl, cyano, nitro, hydroxyl, carbonyl, ester, imido, amino, phosphino, alkoxy, aryloxy, sulfone, sulfoxide, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, heteroaryl, aralkyl, aralkenyl, alkylaryl, alkylamino, aralkylamino, heteroarylamino, arylamino, arylphosphino, heterocyclic group, carboxyl derivative group, etc.; or substituted with a substituent connecting two or more of the substituents exemplified above.

[0020] Aryl: If not otherwise specified, the aryl group may be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, and the like. Polycyclic aryl groups include, but are not limited to, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, fluorenyl, and the like. Fluorenyl groups may be substituted, such as 9,9'-dimethylfluorenyl, 9,9'-dibenzofluorenyl, and the like, and two of the substituents may be combined with each other to form a spiro ring structure, such as 9,9'-spirobifluorenyl, and the like.

[0021] The above description of the aryl group may be applied to the aryl groups in the aryloxy group, arylsilyl group, arylgermanyl group, arylthio group, arylsulfonyl group, arylphosphino group, arylalkyl group, arylalkylamine group, arylalkenyl group, alkylaryl group, arylamine group and arylheteroarylamine group.

[0022] Heteroaryl: Unless otherwise specified, the heteroatom may be boron (B), nitrogen (N), oxygen (O), phosphorus (P), sulfur (S), silicon (Si) or selenium (Se). Heteroaryl includes, but is not limited to, pyridinyl, pyrrolyl, pyrimidinyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, azinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazaindenyl, indolyl, indolinyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazine

[0063] In some embodiments, the heteroaryl group may be substituted with 1,2-diphenyl-2-oxanthene, ...

[0023] Alkyl: If not otherwise specified, the alkyl group may be linear or branched, including but not limited to methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl. The above description of the alkyl group can also be applied to the alkyl groups in the aralkyl group, alkylgermanyl group, aralkylamino group, alkylaryl group and alkylamino group.

[0024] Cycloalkyl: a cyclic saturated hydrocarbon group, such as cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc.

[0025] Heteroalkyl: an alkyl group containing heteroatoms, such as oxygen, sulfur, nitrogen, fluorine, silicon, etc.

[0026] Heterocycloalkyl is a cycloalkyl group containing heteroatoms, such as oxygen, sulfur, nitrogen, fluorine, silicon, etc.

[0027] The first aspect of the present application provides an organic compound, the structural formula of the organic compound is shown in Formula I:

[0028]

[0029] In formula I, Ar1 is selected from an aryl group having 6 to 24 carbon atoms and a heteroaryl group having 5 to 24 carbon atoms.

[0030] In some preferred embodiments, Ar1 is selected from phenyl, naphthyl, biphenyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, phenanthryl, and phenyl-substituted biphenyl.

[0031] In Formula I, R1 to R 16 The same or different and each independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cyano group, a fluorine atom, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 6 to 12 carbon atoms containing a first heteroatom, and the first heteroatom is selected from an oxygen atom and a sulfur atom.

[0032] In some preferred embodiments, the R1 to R 16 In some other preferred embodiments, R1 to R 16 Some of the substituents are hydrogen and the rest are deuterium.

[0033] In Formula I, when the size or connection position of the 10-position substituent Ar2 of the phenanthryl group is different, the degree of spatial conjugation with anthracene is different, which in turn leads to different degrees of voltage reduction. For example, when Ar2 is small, such as phenyl, the spatial conjugation with anthracene is small, so the voltage reduction is small. When larger groups such as naphthyl, phenanthryl, biphenyl, benzofuranyl, benzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl are used, better spatial conjugation with anthracene can occur, so the device voltage can be effectively reduced. In the present application, Ar2 is selected from an aryl group with a carbon number of 10 to 24 and a heteroaryl group with a carbon number of 7 to 24 of a suitable size.

[0034] In some preferred embodiments, Ar2 is selected from the following groups or a combination of the following groups and phenyl: substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, and the substituent when substituted is selected from deuterium, an alkyl group having 1 to 10 carbon atoms, and a heteroalkyl group having 1 to 10 carbon atoms and containing a second heteroatom, wherein the second heteroatom is selected from oxygen, sulfur, nitrogen, fluorine, and silicon, and Ar2 does not contain: * represents the ligation site.

[0035] In some preferred embodiments, Ar2 is selected from the following groups: naphthyl, biphenyl, a combination of naphthyl and phenyl, phenanthryl, triphenylene, a combination of biphenyl and phenyl, 9,9'-dimethylfluorenyl, a combination of dibenzofuranyl and phenyl, a combination of dibenzothienyl and phenyl, carbazolyl, 9,9'-dibenzofluorenyl, spirobifluorenyl, a combination of 9,9'-dimethylfluorenyl and phenyl, benzonaphthofuranyl, benzonaphthothienyl, dibenzofuranyl, dibenzothienyl, dibenzofuranyl substituted naphthyl, dibenzothienyl substituted naphthyl, a combination of benzonaphthofuranyl and phenyl, pyrenyl, and Ar2 does not include:

[0036] In some more preferred embodiments, Ar2 is selected from the following groups:

[0037]

[0038]

[0039] Wherein, * represents a connection site, X is selected from an oxygen atom or a sulfur atom, and Ar2 does not contain:

[0040] It should be noted that the hydrogen in the organic compound of the present application may be replaced by deuterium, and the organic compound of the present application does not contain:

[0041] In some preferred embodiments, the structural formula of the organic compound is selected from the following group:

[0042]

[0043]

[0044] Wherein, X is selected from oxygen atom or sulfur atom. Dn represents n deuterium substitutions, and n is selected from 0 to the maximum number of deuterium substitutions. When partial deuteration is performed, there is no particular restriction on the position of deuteration. Of course, this preferred structural formula excludes

[0045] In some specific embodiments, the organic compound is selected from the group consisting of:

[0046]

[0047]

[0048] The organic compound of the present application can be prepared by the following synthetic route:

[0049]

[0050] The synthesis reactions of the above-mentioned compound MA, compound MB-3, and compound A are Suzuki aryl coupling reactions, and the reaction operations are similar, but the yields of specific compounds are slightly different. The reaction of compound MB-4 is a bromination reaction, and the formation reaction of MB is a borylation reaction.

[0051] As an example, the operation method of the Suziki aryl coupling reaction can be: 1 molar equivalent of a halogen-containing compound and 1.1 molar equivalents of an aromatic boronic acid, 1% molar equivalent of a catalyst Pd2(dba)3 and 2% molar equivalent of S-phos (short for 2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl), 2 molar equivalents of K2CO3, 7 to 20 times the weight of the halide toluene, 1 to 3 times the weight of ethanol, 1 to 3 times the weight of water, the system is replaced with nitrogen 3 times, the reaction is heated to reflux, and the reaction is stirred for 4 to 8 hours. The reaction solution is cooled to room temperature, separated, and concentrated. Rapid silica gel column chromatography (hot toluene), the column liquid is concentrated, refluxed, and n-hexane is added dropwise during the cooling process. After complete cooling, it is stirred for 2 to 4 hours, the solid is filtered, and dried.

[0052] As an example, the operation method of the bromination reaction can be: add 1 molar equivalent of the raw material to a reaction bottle, add 1,2-dichloroethane of 20 to 50 times the weight of the raw material, heat to dissolve, slowly add 1.05 molar equivalent of N-bromosuccinimide (NBS) to the reaction solution in batches, react for 2 to 6 hours, cool the reaction solution, concentrate, and filter to obtain a solid.

[0053] As an example, the operation method of the borylation reaction can be: add 1 molar equivalent of bromination raw material (compound MB-4), 1.3 molar equivalents of (BPin)2, 2 molar equivalents of KOAc, 0.01 molar equivalents of Pd(dppf)Cl2 in a three-necked flask, and then add 10 to 20 times the weight of the bromination raw material (compound MB-4) of toluene, replace the system with nitrogen 3 times, heat the reaction to reflux, and stir the reaction for 2 to 10 hours. TLC detection reaction is complete. The reaction solution is cooled to room temperature, filtered, the filter cake is washed with ethyl acetate 2 to 3 times, the organic phase is dried, toluene and n-hexane are dissolved and cleared through a silica gel column (200 mesh to 300 mesh), and the solution is dried.

[0054] When R1~R 16 When at least one of is deuterium, a deuteration reaction is involved, and the reaction is schematically shown as follows:

[0055]

[0056] The operation method of the deuteration reaction can be: in the presence of a catalyst, placing the compound to be deuterated in a deuterated reagent to carry out the deuteration reaction.

[0057] As an example, the catalyst may include at least one of a proton acid, a Lewis acid, and a polymer bonded sulfonic acid. The proton acid may be selected from trifluoroacetic acid, trifluoromethanesulfonic acid, perfluorobutylsulfonic acid, etc., and the Lewis acid may be selected from aluminum chloride, zinc chloride, molybdenum chloride, etc. The mass of the catalyst may be 3% to 20% of the mass of the deuterated compound. The deuterated reagent may include deuterated benzene. The mass ratio of the deuterated reagent to the deuterated compound is (20 to 50): 1. The reaction temperature may be reflux temperature, and the reaction time may be 1 to 5 days. Generally, 2 to 3 repetitive deuterium substitutions are used, and the deuterium substitution rate can reach more than 90%. The higher the number of substitutions, the higher the deuterium substitution rate, the better the stability of the molecular structure, and the better the lifespan. Since the number of deuterium substitutions is related to cost, the most cost-effective deuterium substitution rate will appear. In the preparation of deuterated compounds, the present application uses two deuterations, and the deuterium substitution rates are all above 95%.

[0058] As an example, the specific operation of the deuterated reaction can be: in a three-necked flask, add 1 molar equivalent of the compound to be deuterated, 0.1 molar equivalent of perfluorobutanesulfonic acid, and 30 to 60 times the weight of the compound to be deuterated of deuterated benzene (deuterated degree 99%). The system is replaced with nitrogen 3 times, the reaction is heated to reflux, and the reaction is stirred for 1 to 5 days. The reaction solution is cooled to room temperature, and the deuterated benzene is removed by rotary evaporation. Dichloromethane and a sodium carbonate solution with a mass fraction of 10% are added, stirred for half an hour, and the liquids are separated. Wash with water again and dry. The organic phase is passed through a silica gel column and rinsed with dichloromethane. The organic phase is spin-dried, pulped with ethanol, filtered, and dried.

[0059] The second aspect of the present application provides use of the aforementioned organic compound in preparing an organic electroluminescent device.

[0060] A third aspect of the present application provides an organic electroluminescent device, comprising a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer comprises the aforementioned organic compound.

[0061] As an example, the first electrode is an anode and the second electrode is a cathode.

[0062] The cathode may be one layer or multiple layers. The organic layer may be a single layer structure or a multilayer series structure in which two or more organic layers are laminated.

[0063] In some embodiments, the organic layer includes a light-emitting layer, and the light-emitting layer includes the above-mentioned organic compound.

[0064] In some embodiments, in the light-emitting layer, the organic compound serves as a light-emitting host material, and the light-emitting layer further includes a light-emitting doping material.

[0065] In some preferred embodiments, the organic compound is used as a blue light-emitting host material to prepare a blue fluorescent light-emitting device.

[0066] In some embodiments, the organic layer may also include at least one organic functional layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and each organic functional layer may be a single layer or a multilayer.

[0067] In some specific embodiments, the structure of the organic electroluminescent device is selected from one of the following:

[0068] (1) An organic electroluminescent device includes an anode, a hole injection layer, a first hole transport layer, a light-emitting layer, a first electron transport layer, and a cathode stacked in sequence, that is, anode / hole injection layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode. Each device structure will be expressed in this simplified manner below.

[0069] (2) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode.

[0070] (3) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / cathode.

[0071] (4) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / electron injection layer / cathode.

[0072] (5) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / multilayer cathode.

[0073] (6) anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode.

[0074] (7) anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / second electron transport layer / cathode.

[0075] (8) anode / hole injection layer / second hole transport layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode.

[0076] (9) anode / hole injection layer / second hole transport layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / second electron transport layer / cathode.

[0077] (10) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode.

[0078] (11) anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode.

[0079] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode.

[0080] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode.

[0081] (14) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection material / cathode.

[0082] The light emission direction of the organic electroluminescent device can be from the anode side or the cathode side. When the light is emitted from the cathode side, the difference from structures (1) to (14) is that a covering layer needs to be added on the cathode surface.

[0083] Some specific functional layers in the organic electroluminescent device are described below.

[0084] Substrate:

[0085] The substrate is generally located below the anode, and the substrate may be made of plastic or glass, and may be rigid or bendable. The substrate is provided with a driving unit, which may drive the corresponding pixel to emit light.

[0086] anode:

[0087] The anode is usually required to have good conductivity, a smooth surface, and be free of cracks. There are also certain requirements for the work function, mainly to be able to match the hole injection layer and exert the hole injection effect.

[0088] When the top emission mode (light emitting from the cathode side) is adopted, the anode adopts a metal compound with a work function of 4.2eV or more, such as indium tin oxide alloy, tin oxide, indium zinc oxide, gold, silver, platinum, copper, carbon nanotubes, carbon nanowires, graphene, etc. The thickness is 10nm to 200nm, preferably 10nm to 50nm. A reflective electrode is set under the anode (close to the substrate end). The reflective electrode is generally made of metal or metal alloy, such as silver metal, copper metal, aluminum metal, gold metal or alloys of these metals and other metals. The reflectivity of the reflective electrode is relatively high, and the reflectivity is required to be above 90%. The thickness is usually used at a thickness of 100nm to 500nm, preferably in the range of 80nm to 150nm.

[0089] When the bottom emission mode (light emitting from the substrate side) is adopted, the anode adopts a metal compound with a work function of 4.2eV or more, for example, indium tin oxide alloy, tin oxide, indium zinc oxide, gold, silver, platinum, copper, carbon nanotubes, carbon nanowires, graphene, etc. The thickness is 10nm to 1μm, preferably 50nm to 200nm.

[0090] The anode can be produced by forming an electrode material into a thin film by a method such as vapor deposition, sputtering, or coating.

[0091] Hole injection layer:

[0092] The thickness of the hole injection layer is generally 3nm to 30nm. The hole injection layer is a mixture of P-type materials and hole transport materials. The purpose of using P-type materials is to receive holes from the anode and transfer them to the hole transport material. The weight proportion of P-type materials in the hole injection layer is generally 0.5% to 10%. When the weight proportion is 0.5% to 3%, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the P-type material and the highest occupied molecular orbital (HOMO) energy level of the HTL material shall not be greater than 0.3eV. When the weight proportion is 3% to 5%, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the P-type material and the highest occupied molecular orbital (HOMO) energy level of the HTL material shall not be greater than 0.5eV. When the weight proportion is 5% to 10%, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the P-type material and the highest occupied molecular orbital (HOMO) energy level of the HTL material shall not be greater than 1eV.

[0093] The P-type material can be made of metal oxides, such as molybdenum oxide, vanadium oxide, tungsten oxide, etc.; it can also be made of organic matter, such as 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-trimethylene tris(cyanoformylidene))tris(2,3,5,6-tetrafluorobenzyl) (PD1, CAS No.: 1224447-88-4), tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), and is not limited thereto. The hole transport material matched with the P-type material can be selected from the material of the second hole transport layer, and can be the same as the material of the second hole transport layer or different.

[0094] First hole transport layer:

[0095] The thickness of the first hole transport layer is generally 3nm to 500nm. When there is no second hole transport layer, the thickness of the first hole transport layer is generally 40nm to 150nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 3nm to 500nm.

[0096] Second hole transport layer:

[0097] The thickness of the second hole transport layer is generally 5 nm to 150 nm, and an aromatic amine compound is often used, which may be an aromatic monoamine or an aromatic polyamine.

[0098] Electron blocking layer:

[0099] The electron blocking layer can have both hole transport and electron blocking functions. At the same time, the higher triplet excitation energy level of the electron blocking layer can lock the excitons generated in the light-emitting layer in the light-emitting layer, thereby improving the luminous efficiency of the device.

[0100] Luminous layer:

[0101] The material of the light-emitting layer generally includes a host material and a guest dopant material. The content of the host material is greater than that of the guest dopant material. Optionally, the mass percentage of the guest dopant material in the light-emitting layer is 1% to 20%.

[0102] The guest doping material as the luminescent material may include phosphorescent or fluorescent materials or thermally activated delayed fluorescent materials, and red light, green light, and blue light may be selected from the above three guest doping materials. For example, the guest doping material of the luminescent layer corresponding to the luminescent unit with a red luminescent color and the luminescent layer corresponding to the luminescent unit with a green luminescent color is a phosphorescent material, and the guest doping material of the luminescent layer corresponding to the luminescent unit with a blue luminescent color is a fluorescent material.

[0103] Or for example, the guest doping material of the light-emitting layer corresponding to the light-emitting unit with red light-emitting color and the light-emitting layer corresponding to the light-emitting unit with green light-emitting color is a phosphorescent material, and the guest doping material of the light-emitting layer corresponding to the light-emitting unit with blue light-emitting color is a phosphorescent material.

[0104] Or for example, the guest doping material of the light-emitting layer corresponding to the light-emitting unit with red light-emitting color and the light-emitting layer corresponding to the light-emitting unit with green light-emitting color is a thermally activated delayed fluorescent material, and the guest doping material of the light-emitting layer corresponding to the light-emitting unit with blue light-emitting color is a fluorescent material.

[0105] Or for example, the guest doping material of the light-emitting layer corresponding to the light-emitting unit with red light-emitting color and the light-emitting layer corresponding to the light-emitting unit with green light-emitting color is a thermally activated delayed fluorescent material, and the guest doping material of the light-emitting layer corresponding to the light-emitting unit with blue light-emitting color is a phosphorescent material.

[0106] As the light-emitting host material, one light-emitting host material or two light-emitting host materials may be selected.

[0107] Hole blocking layer:

[0108] In order to enhance the balance of hole and electron concentrations, a hole blocking layer is inserted to balance the carrier concentration and prevent exciton quenching. Generally, the hole blocking layer is located between the light-emitting layer and the electron transport layer. The hole blocking layer material must meet the conditions of strong stability, good film-forming properties, and a sufficiently high highest molecular occupied orbital.

[0109] First electron transport layer:

[0110] The thickness of the first electron transport layer can generally be 3nm to 40nm, 3nm to 10nm, 10nm to 20nm, 20nm to 30nm, 30nm to 40nm or 20nm to 40nm, etc. When there is no second electron transport layer, the thickness of the first electron transport layer is generally 20nm to 40nm, and when there is a second electron transport layer, the thickness of the first electron transport layer is generally 20nm to 30nm. The first electron transport layer is in direct contact with the light-emitting layer, so similar to the first hole transport layer, electronic changes will also occur during the electron transport process, resulting in increased molecular vibration and molecular deformation. The excitons of the light-emitting layer will also interact with the polarons of the electron transport material, which can easily produce active free radicals and destroy the electron transport material. The electron transport material can be a single compound or mixed with other metal compounds, such as Liq.

[0111] The thickness of the second electron transport layer is generally 10 nm to 40 nm, and the material of the second electron transport layer may include a mixture of an organic electron transport material and a metal compound, or a mixture of an organic electron transport material and a metal.

[0112] When the organic electron transport material is mixed with a metal compound material, for example, it is mixed with an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, and more specifically, it is mixed with a metal lithium compound, a metal calcium compound, a metal Mg compound, a metal samarium compound, a metal ytterbium compound, and more specifically, it is mixed with 8-hydroxyquinoline lithium, lithium fluoride, magnesium fluoride, ytterbium fluoride, calcium fluoride, etc. When mixed with a metal compound, the mass proportion of the organic electron transport material can be 20% to 80%, 20% to 40%, 40% to 60%, or 60% to 80%, etc.

[0113] When the organic electron transport material is mixed with a metal, for example, mixed with an alkali metal, an alkaline earth metal, or a rare earth metal, more specifically, mixed with lithium metal, magnesium metal, calcium metal, ytterbium metal, samarium metal, etc., when mixed with a metal, the mass proportion of the organic electron transport material can be 80% to 99%, 80% to 89%, 89% to 99%, 80% to 85%, 85% to 90%, 90% to 95%, or 95% to 99%, etc.

[0114] Electron injection layer:

[0115] The electron injection layer can reduce the barrier of electron injection from the cathode to the organic layer, improve the electron injection efficiency, and thus optimize the performance of the device. The material selection of the electron injection layer needs to consider its work function matching with the cathode material, and can be selected from alkali metals, alkaline earth metals, rare earth metals, or their inorganic substances or coordination compounds.

[0116] Charge generation layer:

[0117] When a single-layer light-emitting layer device is used, holes and electrons are injected from the anode and cathode respectively, and a charge generation layer is not required. When a double-layer or multi-layer light-emitting layer is used, a charge generation layer is required between the light-emitting layers to achieve the effect of charge generation, injection and transmission. The charge generation layer is located between the two light-emitting layers, and is generally composed of two layers of P / N type materials, wherein the P-type material is selected from the hole injection material mentioned above, and the N-type material is mixed with an organic electron transport material doped with a metal. The organic electron transport layer material is selected from the second electron transport layer mentioned above, and the metal is selected from alkali metals, alkaline earth metals, and rare earth metals, and more specifically, lithium metal, magnesium metal, calcium metal, ytterbium metal, samarium metal, etc. When the organic electron transport material is mixed with the metal, the mass proportion of the organic electron transport material can be 80% to 99%, 80% to 89%, 89% to 99%, 80% to 85%, 85% to 90%, 90% to 95%, or 95% to 99%, etc.

[0118] cathode:

[0119] The cathode requires a material with good electrical conductivity and good surface flatness. In order to improve the electron injection capability, a material with a small work function is usually selected. The cathode material can be a single-layer cathode, or a double-layer or multi-layer cathode, generally a metal or a metal alloy. For a single-layer cathode, silver, copper, aluminum, gold, or alloys of these metals with other metals, such as alloys with rare earth metals, alkali metals, and alkaline earth metals, can be used, which can be listed as magnesium-indium alloy, magnesium-aluminum alloy, aluminum-potassium alloy, aluminum-scandium-potassium alloy, magnesium-silver alloy, silver-ytterbium alloy, silver-samarium alloy, etc. If the cathode uses a double-layer metal, the cathode near the light-emitting layer can use alkali metals, alkaline earth metals, rare earth metals, etc., such as lithium, calcium, magnesium, ytterbium, etc., to increase the electron injection ability, and the cathode layer far from the light-emitting side is mainly used to improve the conductivity. Generally, silver, copper, aluminum, gold or alloys of these metals with other metals, such as alloys with rare earth metals, alkali metals, and alkaline earth metals can be used, which can be listed as magnesium-indium alloy, magnesium-aluminum alloy, aluminum-potassium alloy, aluminum-scandium-potassium alloy, magnesium-silver alloy, silver-ytterbium alloy, silver-samarium alloy, etc. The cathode can also be formed into a thin film by evaporation, sputtering, etc.

[0120] When light comes out from the anode side, the cathode is required to be light-proof, and a cathode with a thickness greater than 100nm can be evaporated. When light comes out from the cathode side, the cathode is required to be transparent, and the transmittance should be greater than 40% at this time, and the thickness should be 10nm to 20nm.

[0121] Overlay:

[0122] When light comes out from the cathode side, photons resonate with electrons in the cathode metal to reduce light extraction efficiency. Adding a covering layer on the cathode side away from the light-emitting layer can reduce this effect and effectively improve light efficiency. When adding a covering layer, a covering layer material with a high refractive index and a low absorption coefficient is directly used, for example, a material with a refractive index greater than 1.9 at a wavelength of 460nm and a material with an absorption rate less than 0.01%, preferably a material with a refractive index greater than 2.0 at a wavelength of 460nm and an absorption rate less than 0.01%, and more preferably a material with a refractive index greater than 2.1 at a wavelength of 460nm and an absorption rate less than 0.01%.

[0123] Below will be combined with the embodiment of the present application, the technical scheme of the present application is clearly and completely described. Unless otherwise specified, the reagents and raw materials used can be purchased through commercial channels. The experimental methods of the following examples that do not specify specific conditions are usually measured according to national standards. If there is no corresponding national standard, then according to general international standards, conventional methods and conditions, or according to the conditions recommended by the manufacturer, or according to the product specification selection. Unless otherwise specified, all parts are weight parts, and all percentages are weight percentages.

[0124] The starting materials and solvents of the following examples were purchased from Sinopharm, some commonly used OLED intermediates and other products were purchased from domestic OLED intermediate manufacturers, and various palladium catalysts were purchased from Sigma Aldrich. HPLC data were measured using a Shimadzu LC 20AD high performance liquid phase analyzer; LC-MS (liquid chromatography-mass spectrometry) was tested on an H-class+SQD2 instrument from Waters Corporation.

[0125] Synthesis Example

[0126] Example 1

[0127] Synthesis of compound 1

[0128]

[0129] 1) Synthesis of Compound MB1-3

[0130] In a clean reaction bottle, 1 molar equivalent of compound MB1-1 (40 g, 156.7 mmol) and 1.1 molar equivalent of phenylboric acid (21 g, 172 mmol), 1% molar equivalent of catalyst Pd2(dba)3 (1.4 g, 1.56 mmol) and 2% molar equivalent of S-phos (1.28 g, 3.12 mmol), 2 molar equivalents of K2CO3 (43 g, 312 mmol), 800 mL of toluene, 80 mL of ethanol, 80 mL of water were added in sequence. The system was replaced with nitrogen 3 times, and the reaction temperature was raised to reflux, and the reaction was stirred for 4 hours. The reaction solution was cooled to room temperature, separated, and concentrated. Rapid silica gel column chromatography (700 mL hot toluene) was performed, and the column liquid was concentrated to 200 mL, refluxed, and 150 mL of n-hexane was added dropwise while cooling. After complete cooling, it was stirred for 2 hours, the solid was filtered, and dried to obtain 35 g of compound MB1-3 with a yield of 87.8%.

[0131] 2) Synthesis of Compound MB1-4

[0132] 1 molar equivalent of compound MB1-3 (35 g, 13.7 mmol) was added to a reaction flask, 500 mL of 1,2-dichloroethane was added, and the mixture was heated to dissolve. 1.05 molar equivalents of NBS (25.6 g, 144.5 mmol) was slowly added to the reaction solution in batches and reacted for 3 hours. The reaction solution was cooled, concentrated, and filtered to obtain 40 g of solid compound MB1-4 with a yield of 87.6%.

[0133] 3) Synthesis of compound MB1

[0134] In a three-necked flask, add 1 molar equivalent of compound MB1-4 (40g, 13.4mmol), 1.3 molar equivalents of (BPin)2 (44g, 17.4mmol), 2 molar equivalents of KOAc (26.2g, 26.8mmol), 0.01 molar equivalent of Pd(dppf)Cl2 (0.98g, 0.134mmol), and then add 600mL of toluene. The system is replaced with nitrogen 3 times, the reaction temperature is raised to reflux, and the reaction is stirred for 3 hours. TLC detection shows that the reaction is complete. The reaction solution is cooled to room temperature, filtered, and the filter cake is washed with ethyl acetate 3 times. The organic phase is dried by rotation, and the toluene and n-hexane solution is passed through a silica gel column (200 mesh to 300 mesh). The solution is dried by rotation to obtain 32g of solid, with a yield of 80%.

[0135] 4) Synthesis of compound MA1

[0136] In a clean reaction bottle, add 1 molar equivalent of compound MA1-1 (40g, 119mmol) and 1.1 molar equivalent of 2-naphthaleneboric acid (22.5g, 130.9mmol), 1% molar equivalent of catalyst Pd2(dba)3 (1.09g, 1.19mmol) and 2% molar equivalent of S-phos (0.98g, 2.38mmol), and 2 molar equivalent of K2CO3 (32.8g, 238mmol), 600mL toluene, 60mL ethanol, 60mL water, the system nitrogen is replaced 3 times, the reaction is heated to reflux, and the reaction is stirred for 4 hours. The reaction solution is cooled to room temperature, separated, and concentrated. Rapid silica gel column chromatography (200mL hot toluene), the column liquid is concentrated to 100mL, reflux, and 50mL of n-hexane is added dropwise while the temperature is reduced. After complete cooling, stir for 2 hours, filter the solid, and dry to obtain 38g of compound MA1 with a yield of 83.3%.

[0137] 5) Synthesis of Compound 1

[0138] In a clean reaction bottle, add 1 molar equivalent of compound MA1 (35g, 91.3mmol) and 1.1 molar equivalent of compound MB1 (30g, 100.5mmol), add 1% molar equivalent of catalyst Pd2(dba)3 (0.083g, 0.091mmol) and 2% molar equivalent of S-phos (0.74g, 1.82mmol), 2 molar equivalent of K2CO3 (25g, 182mmol), 500mL toluene, 50mL ethanol, 50mL water, replace the system with nitrogen 3 times, heat the reaction to reflux, stir and react for 4 hours. The reaction solution is cooled to room temperature, separated and concentrated. Rapid silica gel column chromatography (1200mL hot toluene), the column liquid is concentrated to 300mL, reflux, 50mL n-hexane is added dropwise while cooling, and after complete cooling, it is stirred for 2 hours, the solid is filtered and dried to obtain 17.7g of compound 1, with a yield of 35%. The mass spectrum M / Z is 556.2.

[0139] Example 2

[0140] Synthesis of compound 2

[0141]

[0142] The difference from Example 1 is that the compound MA1-2 in step 4) is replaced by the compound MA2-2, and the yield is 78%; the compound MA1 in step 5) is replaced by the compound MA2, and the yield is 28%. The mass spectrum M / Z is 556.2.

[0143] Example 3

[0144] Synthesis of compound 3

[0145]

[0146] The difference from Example 1 is that the compound MA1-2 in step 4) is replaced by compound MA3-2, and the yield is 83%; the compound MA1 in step 5) is replaced by compound MA3, and the yield is 34%. The mass spectrum M / Z is 582.1.

[0147] Example 4

[0148] Synthesis of compound 8

[0149]

[0150] The difference from Example 1 is that the compound MA1-1 in step 4) is replaced by compound MA8-2, and the yield is 80%; the compound MA1 in step 5) is replaced by compound MA8, and the yield is 28%. The mass spectrum M / Z is 606.2.

[0151] Example 5

[0152] Synthesis of compound 9

[0153]

[0154] The difference from Example 1 is that the compound MA1-1 in step 4) is replaced by compound MA9-2, and the yield is 81%; the compound MA1 in step 5) is replaced by compound MA9, and the yield is 25%. The mass spectrum M / Z is 606.2.

[0155] Example 6

[0156] Synthesis of compound 19

[0157]

[0158] The difference from Example 1 is that the compound MA1-1 in step 4) is replaced by compound MA19-2, and the yield is 81%. The compound MA1 in step 5) is replaced by compound MA19, and the yield is 29%. The mass spectrum M / Z is 672.2.

[0159] Example 7

[0160] Synthesis of compound 20

[0161]

[0162] The difference from Example 1 is that the compound MA1-1 in step 4) is replaced by compound MA20-2, and the yield is 76%. The compound MA1 in step 5) is replaced by compound MA20, and the yield is 33%. The mass spectrum M / Z is 672.2.

[0163] Example 8

[0164] Synthesis of compound 24

[0165]

[0166] The difference from Example 1 is that the compound MA1-1 in step 4) is replaced by compound MA24-2, and the yield is 77%. The compound MA1 in step 5) is replaced by compound MA24, and the yield is 25%. The mass spectrum M / Z is 744.2.

[0167] Example 9

[0168] Synthesis of compound 32

[0169]

[0170] The difference from Example 1 is that the compound MA1-1 in step 4) is replaced by compound MA32-2, and the yield is 81%. The compound MA1 in step 5) is replaced by compound MA32, and the yield is 27%. The mass spectrum M / Z is 646.2.

[0171] Example 10

[0172] Synthesis of compound 43

[0173]

[0174] The difference from Example 1 is that the compound MB1-2 in step 1) is replaced by compound MB43-2, and the compound MB1 in step 5) is replaced by MB43; wherein, the reaction yield of step 1) is 84%, the reaction yield of step 2) is 91%, the reaction yield of step 3) is 81%, the reaction yield of step 5) is 33%, and the mass spectrum M / Z is 606.2.

[0175] Embodiment 11

[0176] Synthesis of compound 52

[0177]

[0178] The difference from Example 9 is that the compound MA1 in step 5) is replaced by compound MA9, and the yield is 28%. The mass spectrum M / Z is 565.2.

[0179] Example 12

[0180] Synthesis of compound 56

[0181]

[0182] The difference from Example 1 is that the compound MB1-2 in step 1) is replaced by MB56-2, and the compound MB1 in step 5) is replaced by compound MB56. The reaction yield of step 1) is 86%, the reaction yield of step 2) is 88%, the reaction yield of step 3) is 83%, and the reaction yield of step 5) is 35%. The mass spectrum M / Z is 646.8.

[0183] Example 13

[0184] Synthesis of compound 67

[0185]

[0186] The difference from Example 1 is that the compound MB1-1 in step 1) is replaced by MB67-1, and the compound MB1 in step 5) is replaced by compound MB67. The reaction yield of step 1) is 87%, the reaction yield of step 2) is 86%, the reaction yield of step 3) is 80%, and the reaction yield of step 5) is 35%. The mass spectrum M / Z is 564.2.

[0187] Embodiment 14

[0188] Synthesis of compound 68

[0189]

[0190] The difference from Example 1 is that the compound MB1-1 in step 1) is replaced by the deuterated compound MB67-1, the compound MB1-2 is replaced by the deuterated compound MB68-2, and the compound MB1 in step 5) is replaced by the compound MB68. The reaction yield of step 1) is 88%, the reaction yield of step 2) is 87%, the reaction yield of step 3) is 81%, and the yield of step 5) is 35%. The mass spectrum M / Z is 569.3.

[0191] Embodiment 15

[0192] Synthesis of compound 69

[0193]

[0194] In a clean 1000mL three-necked flask, add compound 1 (10 grams, 17.9mmol), perfluorobutylsulfonic acid (1 gram, 2.21.8mmol), and 300mL of deuterated benzene (99% deuterated). The system was replaced with nitrogen three times, the reaction temperature was raised to reflux, and the reaction was stirred for 6 days. The reaction solution was cooled to room temperature and deuterated by rotary evaporation. Add 300mL of dichloromethane and 200mL of 10% sodium carbonate solution by mass, stir for half an hour, and separate the liquids. Wash with water again and dry. The organic phase was passed through a silica gel column and rinsed with dichloromethane. The organic phase was spin-dried, pulped with 400mL of ethanol, filtered, and dried to obtain 8.8 grams of product with a yield of 84%. The same method was used for the second deuteration, with a yield of 85%, a total yield of 71% for two times, and a mass spectrum of M / Z = 584.3.

[0195] The compound prepared in the above example was purified by sublimation and then used for the following device preparation.

[0196] Device Embodiment

[0197] Example 16

[0198] refer to Figure 1 This embodiment provides an organic electroluminescent device, and its preparation method includes the following steps:

[0199] (1) On a glass substrate 101, a transparent anode ITO film layer 102 with a thickness of 150 nm is formed by a magnetron sputtering process.

[0200] (2) A mixed material of compound M1 and compound M2 with a mass ratio of 97:3 is deposited on the surface of the transparent anode ITO film layer 102 by vacuum evaporation to form a hole injection layer 103 with a thickness of 100 angstroms.

[0201] (3) Compound M1 was evaporated on the surface of the hole injection layer 103 to form a first hole transport layer 104 with a thickness of 900 angstroms.

[0202] (4) Compound M3 is evaporated on the surface of the first hole transport layer 104 to form a second hole transport layer 105 with a thickness of 50 angstroms.

[0203] (5) Compound 1 of the present application and compound M4 were co-evaporated on the surface of the second hole transport layer 105 at a mass ratio of 98:2 to form a light-emitting layer 106 with a thickness of 200 angstroms.

[0204] (6) Compound M5 is evaporated on the surface of the light-emitting layer 106 to form a hole blocking layer 107 with a thickness of 50 angstroms.

[0205] (7) A mixed material of compound M6 and compound M7 in a mass ratio of 1:1 was evaporated on the surface of the hole blocking layer 107 to form an electron transport layer 108 with a thickness of 300 angstroms.

[0206] (8) Metal Yb was evaporated on the electron transport layer 108 to form an electron injection layer 109 with a thickness of 10 angstroms.

[0207] (9) Magnesium (Mg) and silver (Ag) are mixed and deposited on the electron injection layer 109 at a vapor deposition rate of 1:10 to form a cathode 110 with a thickness of 1000 angstroms, thereby completing the preparation of the organic electroluminescent device.

[0208] The structural formula of the compound involved in the above preparation method is shown in Table 1 below:

[0209] Table 1 Structural formula of related compounds Embodiments 17 to 30

[0210] An organic electroluminescent device was prepared by the same method as in Example 16, except that compound 2, 3, 8, 9, 19, 20, 24, 32, 43, 52, 56, 67, 68, and 69 of the present application were used to replace compound 1 when forming the light-emitting layer 106.

[0211] Comparative Examples 1 to 5

[0212] The organic electroluminescent device was prepared in the same manner as in Example 16, except that compounds D1 to D5 were used to replace compound 1 when forming the light-emitting layer 106. The structural formulas of compounds D1 to D5 are as follows:

[0213]

[0214] The Keithley 2400 test system controlled by a computer calculated the device's current at a test current of 10 mA / cm 2 The LT95 lifetime of the device was tested under dark conditions (ambient temperature was 25°C, constant current was 50 mA / cm 2 ), LT95 life refers to the time required for the brightness to decrease from the initial brightness to 95%.

[0215] Examples 16 to 24, Examples 28 to 30 and Comparative Examples 1 to 3 were produced and tested in the same batch. Taking the operating voltage, current efficiency and LT95 life of the device of Comparative Example 1 as 100%, the test results shown in Table 2-1 were obtained.

[0216] Table 2-1 Device performance test results

[0217]

[0218]

[0219] Example 25, Example 26 and Comparative Example 4 were produced and tested in the same batch. Taking the operating voltage, current efficiency and LT95 life of the device of Comparative Example 4 as 100%, the test results shown in Table 2-2 were obtained.

[0220] Table 2-2 Device performance test results

[0221] project Compound Voltage efficiency life Comparative Example 4 D4 100％ 100％ 100％ Embodiment 25 43 96％ 100％ 105％ Embodiment 26 52 95％ 101％ 107％

[0222] Example 27 and Comparative Example 5 were produced and tested in the same batch. Taking the operating voltage, current efficiency and LT95 life of the device of Comparative Example 5 as 100%, the test results shown in Table 2-3 were obtained.

[0223] Table 2-3 Device performance test results

[0224] project Compound Voltage efficiency life Comparative Example 5 D5 100％ 100％ 100％ Embodiment 27 56 97％ 100％ 102％

[0225] Referring to Table 2-1, according to the comparison results of Comparative Example 1 and Comparative Example 2, compared with the 9-position substitution of phenanthrene, when the 2-position substitution of phenanthrene is used, the voltage and life of the device are improved, but the device efficiency will also be significantly reduced. According to the comparison results of Comparative Example 1 and Comparative Example 3, the 9-position and 10-position substitution of phenanthrene at the same time can overcome the disadvantage of higher device voltage when the 9-position substitution is used, and the life can also be improved, and the efficiency will not be affected, but the overall improvement of various performances of Comparative Example 3 is small, because when a smaller phenyl group is used to replace the 10-position of phenanthrene, the spatial conjugation effect with anthracene is small, so the performance improvement is not good.

[0226] Combining Table 2-1 to Table 2-3, it can be seen that the present application selects an aromatic group with 10 to 24 carbon atoms or a heteroaromatic group with 7 to 24 carbon atoms to replace the 10th position of phenanthrene. The substituent can form a suitable spatial conjugation with anthracene, so that the conjugation center of anthracene changes, thereby greatly improving the hole mobility of the compound, effectively reducing the device voltage, and maintaining high device efficiency. At the same time, the spatial conjugation can also improve the stability of the compound, thereby improving the device life. Further, when the compound is deuterated, the life is significantly improved.

[0227] In summary, the organic compound of the present application is substituted with an anthracene group at the 9-position of the phenanthrene and with an aryl group with 10 to 24 carbon atoms or a heteroaryl group with 7 to 24 carbon atoms at the 10-position. When it is applied to the preparation of an organic electroluminescent device, the device can have low voltage, high life and high efficiency, and has good application prospects in the field of blue fluorescent light-emitting devices.

[0228] The above description of the embodiments is to facilitate those of ordinary skill in the art to understand and apply the present application. It is obvious that those familiar with the art can easily make various modifications to these embodiments and apply the general principles described herein to other embodiments without having to pay creative labor. Therefore, the present application is not limited to the embodiments herein, and improvements and modifications made by those skilled in the art based on the contents disclosed in the present application without departing from the scope and spirit of the present application are within the scope of the present application.

Claims

1. An organic compound, characterized in that Its structural formula is shown in Formula I: In Formula I, Ar1 is selected from an aryl group having 6 to 24 carbon atoms and a heteroaryl group having 5 to 24 carbon atoms; Ar2 is selected from an aryl group having 10 to 24 carbon atoms and a heteroaryl group having 7 to 24 carbon atoms; R1~R 16 the same or different and independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cyano group, a fluorine atom, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group containing a first heteroatom, wherein the first heteroatom is selected from an oxygen atom and a sulfur atom; The hydrogen in the organic compound may be substituted by deuterium, and the organic compound does not contain:

2. The organic compound according to claim 1, characterized in that The Ar2 is selected from the following groups or a combination of the following groups and phenyl: substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted peryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, and the substituent when substituted is selected from deuterium, an alkyl group having 1 to 10 carbon atoms, or a heteroalkyl group containing a second heteroatom, wherein the second heteroatom is selected from oxygen, sulfur, nitrogen, fluorine, and silicon, and the Ar2 does not contain: * represents the ligation site.

3. The organic compound according to claim 2, characterized in that The Ar2 is selected from the following groups: naphthyl, biphenyl, a combination of naphthyl and phenyl, phenanthryl, triphenylene, a combination of biphenyl and phenyl, 9,9'-dimethylfluorenyl, a combination of dibenzofuranyl and phenyl, a combination of dibenzothienyl and phenyl, carbazolyl, 9,9'-dibenzofluorenyl, spirobifluorenyl, a combination of 9,9'-dimethylfluorenyl and phenyl, benzonaphthofuranyl, benzonaphthothienyl, dibenzofuranyl, dibenzothienyl, dibenzofuranyl substituted naphthyl, dibenzothienyl substituted naphthyl, a combination of benzonaphthofuranyl and phenyl, pyrenyl, and the Ar2 does not include:

4. The organic compound according to claim 3, characterized in that The Ar2 is selected from the following groups: Wherein, * represents a connection site; X is selected from an oxygen atom or a sulfur atom; and Ar2 does not contain:

5. The organic compound according to any one of claims 1 to 4, characterized in that The Ar1 is selected from phenyl, naphthyl, biphenyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, benzonaphthothiophenyl, phenanthryl, and phenyl-substituted biphenyl.

6. The organic compound according to claim 5, characterized in that The structural formula of the organic compound is selected from the following group: Wherein, X is selected from an oxygen atom or a sulfur atom; Dn represents n deuterium substitutions, and n is selected from 0 to the maximum number of deuterium substitutions; And the structural formula of the organic compound does not contain:

7. The organic compound according to claim 6, characterized in that The organic compound is selected from the group consisting of:

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

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

10. The organic electroluminescent device according to claim 9, characterized in that: The organic layer includes a light-emitting layer, and the light-emitting layer includes the organic compound.

11. The organic electroluminescent device according to claim 10, characterized in that: In the light-emitting layer, the organic compound serves as a light-emitting host material, and the light-emitting layer further includes a light-emitting doping material.

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