Organic compound and application thereof in organic electroluminescent device

Abstract

The invention relates to an organic compound, an organic material adopting the organic compound and application of the organic compound and the organic material in an organic electroluminescent device. The invention also relates to an organic electroluminescent device using the organic compound, and an electronic device using the organic electroluminescent device. The organic compound provided by the invention has a chemical structure as shown in a formula (I): # imgabs0. The organic compound provided by the invention can be applied to an organic functional layer of an OLED (Organic Light Emitting Diode) device, in particular to a hole transport layer; on one hand, good molecular stability is achieved, the working voltage of a device can be reduced, and the service life of the device is prolonged or guaranteed; and on the other hand, unnecessary transmission of electrons among molecules can be reduced, the mobility of the material can be improved, the efficiency of the device can be improved, and the material has a relatively strong application space in OLED devices as a hole transport layer material.

Description

Technical Field

[0001] The present invention relates to an organic compound, an organic material using the organic compound, and their application in an organic electroluminescent device; the present invention also relates to an organic electroluminescent device using the organic compound, and an electronic device using the organic electroluminescent device; the present invention belongs to the technical field of organic electroluminescent materials. Background Art

[0002] Electroluminescence (EL) refers to the phenomenon that luminescent materials emit light under the action of electric field and are stimulated by current and electric field. It is a luminescence process that directly converts electrical energy into light energy.

[0003] Organic Light Emission Diode (OLED) devices have the characteristics of high brightness, wide range of material selection, low driving voltage and fully solidified active luminescence. They also have the advantages of high clarity, wide viewing angle and high-speed response for smooth display of animations. They have been a hot research field in the past decade.

[0004] Generally, an OLED device is mainly composed of three parts: an anode, a cathode, and an organic layer between the anode and the cathode.

[0005] Functionalized organic materials commonly used in OLED devices include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as luminescent host materials and luminescent guests (dyes).

[0006] Currently, the industrial development of OLED is limited by the performance of the above-mentioned functionalized organic materials. Those skilled in the art hope to develop new organic materials that can be applied to OLED devices to improve the luminous efficiency of OLED devices and / or extend the life of the devices. Summary of the invention

[0007] In order to solve the above technical problems, the first aspect of the present invention provides an organic compound, wherein the organic compound has the following structural formula (I):

[0008]

[0009] In the formula (I), L 1 , L 2 and L 3 Each is independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C1-C30 heteroarylene group;

[0010] Ar 1 and Ar2 The same or different groups are independently selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C1-C30 heteroaryl groups, or they are bonded to adjacent atoms to form a ring.

[0011] A second aspect of the present invention provides an organic material, wherein the organic material comprises the aforementioned organic compound.

[0012] The third aspect of the present invention provides use of the aforementioned organic compound or the aforementioned organic material in an organic electroluminescent device.

[0013] A fourth aspect of the present invention provides an organic electroluminescent device, which comprises a first electrode, a second electrode and at least one organic functional layer located between the first electrode and the second electrode, wherein the organic functional layer comprises the aforementioned organic compound.

[0014] A fifth aspect of the present invention provides an electronic device, wherein the electronic device comprises the aforementioned organic electroluminescent device.

[0015] The organic compound provided by the present invention, from the perspective of molecular structure, on the one hand, introduces two aromatic amine systems into the core benzene ring structure, thereby increasing the molecular conjugation, improving the stability of the molecule, reducing the operating voltage of the device, and increasing or ensuring the life of the device; on the other hand, two dibenzofuran structures are introduced, the molecular planarity is increased, and the stacking between molecules is better, which can reduce unnecessary transmission of electrons between molecules, improve the mobility of the material, and improve the efficiency of the device; the organic compound provided by the present invention can be applied to the organic functional layer of an OLED device, and in particular, has a strong application space as a hole transport layer material in an OLED device. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] 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:

[0017] Figure 1 This is a schematic diagram of the structure of device embodiments 1-15 of the present application. DETAILED DESCRIPTION

[0018] Unless otherwise specified, the following words, phrases and symbols used in this specification generally have the meanings described below.

[0019] Generally, the nomenclature used herein (e.g., IUPAC nomenclature) and the laboratory procedures described below (including for organic chemistry, analytical chemistry, etc.) are those well-known and commonly used in the art. Unless otherwise defined, all scientific and technical terms used herein in conjunction with the present disclosure described herein have the same meanings as commonly understood by those skilled in the art. In addition, in the claims and / or the specification, when the term "one" or "an" is used in conjunction with the term "comprising" or a noun, its meaning may be "one", but it is also consistent with the meaning of "one or more", "at least one" and "one or more than one". Similarly, the term "another" or "other" can mean at least a second or more.

[0020] It should be understood that whenever various aspects are described herein with the terms "including" or "comprising," other similar aspects described by "consisting of" and / or "consisting essentially of" are also provided.

[0021] In this article, the term "single bond" means that the group mentioned is a bond linker, and the two groups adjacent to the group are directly connected. For example, the phrase "L1 is a single bond" means that L1 is a bond linker, in other words, the N atom in the compound of formula (I) is directly connected to the core phenyl group.

[0022] As used herein, the term "substituted or unsubstituted" refers to a hydrogen atom in a functional group being replaced by another atom or functional group (i.e., a substituent), for example, by one or more of the following substituents: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, a linear or branched alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphino group, a heterocyclic group; or by a combination of two or more of the substituents listed above, for example, diphenyl and terphenyl.

[0023] Herein, the "straight or branched alkyl" is preferably a "straight or branched alkyl having 1 to 10 carbon atoms", wherein the number of carbon atoms is preferably 1 to 8, the number of carbon atoms is further preferably 1 to 6, and more preferably 1 to 4. In some embodiments, the alkyl group may include, but is not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, and the like.

[0024] Herein, the "cycloalkyl" is preferably a "cycloalkyl having 3 to 10 carbon atoms", more preferably a mono- or polycyclic hydrocarbon having 3 to 10 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 9, the number of carbon atoms is preferably 3 to 8, and more preferably 3 to 7. In some embodiments, the cycloalkyl may include, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like.

[0025] In this article, the term "alkoxy" refers to -O (alkyl). Optionally, the alkyl portion of the alkoxy group may contain 1-10 carbon atoms, 1-6 carbon atoms, or 1-4 carbon atoms, etc. In some embodiments, the alkoxy group may include, but is not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, etc.

[0026] In this article, the term "aryl", preferably a substituted or unsubstituted (sub)aryl having 6 to 30 carbon atoms, refers to a monocyclic or condensed ring group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, wherein the number of ring skeleton carbon atoms is preferably 6 to 25, 6 to 20, 6 to 15, 6 to 12, and more preferably 6 to 10. In some embodiments, monocyclic (sub)aryl includes but is not limited to phenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, etc. In some embodiments, condensed ring (sub)aryl includes but is not limited to naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, fluorenyl, etc. In some embodiments, condensed ring (sub)aryl can be substituted, such as substituted fluorenyl, optionally, methylfluorenyl, dimethylfluorenyl (optionally, 9,9-dimethylfluorenyl), phenylfluorenyl, diphenylfluorenyl (optionally, 9,9-diphenylfluorenyl), benzofluorenyl. In other embodiments, the fused ring (lene)aryl group may also contain a spiro structure; for example, 9,9'-spirobifluorenyl.

[0027] The above description of the aryl group can be applied to the aryl groups in the aryloxy group, aryloxythio group, aryloxysulfonyl group, arylphosphino group, arylalkyl group, arylalkylamino group, arylalkenyl group, alkylaryl group, arylamino group and the like.

[0028] In this article, the term "heteroaryl", preferably a substituted or unsubstituted (sub) heteroaryl having 1 to 30 carbon atoms, is an aryl having a ring skeleton atom, wherein the ring skeleton atom includes at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se and Ge, preferably at least one heteroatom selected from N, O and S, wherein the number of ring skeleton carbon atoms is preferably 1 to 30, 1 to 25, 1 to 20, 1 to 15, 1 to 12, 1 to 6. The number of heteroatoms in the heteroaryl is preferably 1 to 4. The above heteroaryl can be a monocyclic ring or a condensed ring condensed with at least one benzene ring. In addition, herein, the above heteroaryl can be a heteroaryl formed by connecting at least one heteroaryl or aryl to a heteroaryl via one or more single bonds. In some embodiments, monocyclic heteroaryl includes but is not limited to furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyl, azinyl, oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc. In other embodiments, the fused ring heteroaryl groups include but are not limited to benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, dinaphthofuranyl, naphthiobenzofuranyl, dinaphthothiophenyl, naphthiobenzothienyl, naphthrydinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyrazinyl, triazaindenyl, indolyl, indolizinyl, phthalazinyl, benzocarbazolyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzocarbazolyl, benzopyrazinyl, pyrimidoindolyl, pyrazinoindolyl, imidazopyridinyl, spirofluoreneoxanthryl, spirofluoreneazaanthryl and the like.

[0029] The above description of the heteroaryl group applies to the heteroaryl group in the heteroarylamine group and the arylheteroarylamine group.

[0030] In the present specification, the expression "bonds to adjacent atoms to form a ring" means a case where adjacent atoms can bond to each other to form a ring.

[0031] On the one hand, the present application provides an organic compound having the following structural formula (I):

[0032]

[0033] In the formula (I), L 1 , L 2 and L 3 Each is independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C1-C30 heteroarylene group;

[0034] Ar 1 and Ar 2 The same or different groups are independently selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C1-C30 heteroaryl groups, or they are bonded to adjacent atoms to form a ring.

[0035] It should be noted that L 2 The connecting position of the dibenzofuran group connected thereto can be at any substitutable position of the connected benzene ring.

[0036] In some embodiments, the Ar 1 and Ar 2 The same as or different from each other, each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms. The substituted or unsubstituted aryl group having 6 to 30 carbon atoms may optionally have 6 to 28, 8 to 25, 10 to 22, 12 to 20, or 14 to 18 carbon atoms. The substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms may optionally have 1 to 28, 5 to 25, 8 to 22, 10 to 20, 12 to 18, or 14 to 16 carbon atoms.

[0037] Preferably, Ar 1 ,Ar 2 are the same as or different from each other, and are independently selected from one or a combination of substituted or unsubstituted phenyl, biphenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, spirofluorenyl, spirofluorenyl, spirofluorenyl, dibenzofuranyl, dibenzothienyl, naphthyl, phenanthryl, or a combination of several thereof, or are bonded to adjacent atoms to form a ring. In some embodiments, Ar 1 with Ar 2 Any two adjacent groups in the group may be bonded to form a ring, for example, they may be bonded to form a ring-shaped substituted or unsubstituted spirofluorene xanthracene or spirofluorene azaanthracene.

[0038] Preferably, the dimethylfluorenyl is 9,9-dimethylfluorenyl; preferably, the diphenylfluorenyl is 9,9-diphenylfluorenyl; preferably, the spirofluorenyl is 9,9'-spirobifluorenyl; preferably, the spirofluorenyloxanthracene is spiro[fluorene-9,9'-oxanthracene]yl; preferably, the spirofluorenylazaanthracenyl is spiro[fluorene-9,9'-azaanthracenyl].

[0039] In some embodiments, L 1 , L 2 , L 3The same as or different from each other, independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, and the arylene group does not include anthrylene, and the heteroarylene group does not include triazine group and carbazolyl group. Wherein, the substituted or unsubstituted arylene group having 6 to 30 carbon atoms may optionally have 6 to 28, 8 to 25, 10 to 22, 12 to 20 or 14 to 18 carbon atoms. Wherein, the substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms may optionally have 1 to 28, 5 to 25, 8 to 22, 10 to 20, 12 to 18 or 14 to 16 carbon atoms.

[0040] In some embodiments, the L 1 , L 2 , L 3 Each is independently selected from a single bond or a substituted or unsubstituted group: phenylene, biphenylene, naphthylene, dimethylfluorenylene, diphenylfluorenylene, spirofluorenylene, spirofluorenylene, spirofluorenylene oxanthracenylene, spirofluorenylene azaanthrylene or a combination thereof, or is bonded to adjacent atoms to form a ring, for example, L 1 and L 2 Any two groups in the group may be bonded to form a cyclic substituted or unsubstituted spirofluorene xanthracene or spirofluorene azaanthracene.

[0041] Preferably, the dimethylfluorenylene group is 9,9-dimethylfluorenylene; preferably, the diphenylfluorenylene group is 9,9-diphenylfluorenylene; preferably, the spirofluorenylene group is 9,9'-spirodifluorenylene; preferably, the spirofluorenylene oxygen anthracene group is spiro[fluorene-9,9'-oxyanthracene] group; preferably, the spirofluorenylene azaanthracene group is spiro[fluorene-9,9'-azaanthracene] group.

[0042] Preferably, the L 1 , L 2 and L 3 At least one of them is a single bond.

[0043] In this application, L 1 , L 2 , L 3 ,Ar 1 ,Ar 2 In the above, the substituent in the "substituted" is selected from a substituted or unsubstituted straight or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, and a heteroaryl group having 3 to 15 carbon atoms.

[0044] Preferably, the substituent in the "substituted" is selected from cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, phenyl, methylphenyl, tert-butylphenyl, naphthyl, biphenyl and the like.

[0045] According to some embodiments, the organic compound is selected from any one of the following chemical structures:

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054] In the above formulas H1 to H180, wherein Ar 2 Independently selected from one or a combination of phenyl, biphenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, spirofluorenyl, spirofluorenyloxanthryl, spirofluorenylazaanthryl, dibenzofuranyl, dibenzothienyl, naphthyl, phenanthryl, or a combination of several thereof, or bonded to adjacent atoms to form a ring;

[0055] The L 1 A single bond or a substituted or unsubstituted group selected from the following groups: phenylene, biphenylene, naphthylene, dimethylfluorenylene, diphenylfluorenylene, spirofluorenylene, spirofluorenylene oxanthracenylene, spirofluorenylene azaanthrylene or a combination of several of them, or bonded to adjacent atoms to form a ring;

[0056] Preferably, the dimethylfluorenyl is 9,9-dimethylfluorenyl; preferably, the diphenylfluorenyl is 9,9-diphenylfluorenyl; preferably, the spirofluorenyl is 9,9'-spirobifluorenyl; preferably, the spirofluorenyloxanthracene is spiro[fluorene-9,9'-oxanthracene]yl; preferably, the spirofluorenylazaanthracenyl is spiro[fluorene-9,9'-azaanthracenyl].

[0057] In some preferred embodiments, the organic compound is selected from any one of the following structural formulas:

[0058]

[0059] Another aspect of the present application provides an organic material, which includes any one of the aforementioned organic compounds. Any one of the aforementioned organic compounds and the organic material can be applied to an organic electroluminescent device.

[0060] The present application also provides an organic electroluminescent device, comprising a first electrode, a second electrode and the aforementioned organic layer. As an example, the first electrode is an anode, the second electrode is a cathode, and the cathode can be one or more layers. The organic layer is located between the first electrode and the second electrode. The organic layer can be a single-layer structure or a multi-layer series structure in which two or more organic layers are laminated. The organic layer includes at least one layer of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer and an electron transport layer.

[0061] In some preferred embodiments, the organic compound of the present application (any of the aforementioned organic compounds) can be used as an electron blocking layer material and / or a light-emitting layer host material.

[0062] In some specific embodiments, the structure of the organic electroluminescent device can be selected from one of the following:

[0063] (1) An organic electroluminescent device comprises 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. The device structure will be expressed in this simplified manner below.

[0064] (2) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode.

[0065] (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.

[0066] (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.

[0067] (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.

[0068] (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.

[0069] (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.

[0070] (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.

[0071] (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.

[0072] (10) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode.

[0073] (11) anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode.

[0074] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode.

[0075] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode (device structure of an embodiment of the present application).

[0076] The light emission direction of the organic electroluminescent device can be emitted from the anode side or the cathode side. In some specific embodiments, if the light emission direction is from the cathode side, it is necessary to add another covering layer on the cathode side. The specific structure is as follows:

[0077] 1) Anode / hole injection layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode / covering layer.

[0078] 2) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode / covering layer.

[0079] 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 / covering layer.

[0080] 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 / covering layer.

[0081] 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 / covering layer.

[0082] 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 / covering layer.

[0083] 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 / covering layer.

[0084] 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 / covering layer.

[0085] 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 / covering layer.

[0086] 10) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode / covering layer.

[0087] 11) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode / covering layer.

[0088] 12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode / covering layer.

[0089] 13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode / covering layer.

[0090] Some specific functional layers in the organic electroluminescent device will be described below.

[0091] Substrate:

[0092] 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.

[0093] anode:

[0094] Organic EL (Organic Electro-Luminescence) components usually have requirements for the anode to have good conductivity, a flat surface, and not prone to cracks. At the same time, there are certain requirements for the work function, mainly to be able to match the hole injection layer and exert the hole injection effect.

[0095] 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.

[0096] When the bottom emission mode (light emitting from the negative 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.

[0097] The anode can be produced by forming an electrode material into a thin film by a method such as vapor deposition, sputtering, or coating.

[0098] Hole injection layer:

[0099] The thickness of the hole injection layer is generally 3nm to 20nm. 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.

[0100] 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.

[0101] Second hole transport layer:

[0102] The thickness of the second hole transport layer is generally 40nm to 150nm, and aromatic amine compounds are often used, which can be aromatic monoamines or aromatic polyamines. The hole transport material is required to have high hole mobility, be able to reduce the driving voltage, and have a glass transition temperature exceeding 100°C to avoid crystallization at high temperatures.

[0103] First hole transport layer:

[0104] The thickness of the first hole transport layer is generally 3nm to 220nm. 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 120nm. In general, red light, green light, blue light, yellow light, etc. need to be adjusted in thickness according to the "microcavity effect", and the thickness selection is also different. Taking the top-emitting light-emitting device as an example, the formula for the microcavity is as follows:

[0105]

[0106] Where n i ,d i Respectively indicate the refractive index and thickness of the i-th layer, m is an integer, which is the modulus of the microcavity, and is more commonly 1 or 2; θ 1 ,θ 2 They represent the phase shift of light at the anode interface and the cathode interface respectively.

[0107] Red light, green light, blue light or other colors of light have different wavelengths, so each color has its optimal thickness. Taking the modulus of 2 as an example, for red light, when there is no second hole transport layer, the thickness of the first hole transport layer is generally 160nm~220nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 8nm~120nm. For green light, when there is no second hole transport layer, the thickness of the first hole transport layer is generally 100nm~180nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 30nm~70nm. For blue light, when there is no second hole transport layer, the thickness of the first hole transport layer is generally 80nm~130nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 3nm~30nm. When other colors are selected, there will be different optimal "microcavity adjustment thickness"

[0108] Electron blocking layer:

[0109] 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.

[0110] Luminous layer:

[0111] 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%.

[0112] 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.

[0113] 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.

[0114] 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.

[0115] 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.

[0116] In order to reduce the power consumption of the organic light-emitting display panel in the organic electroluminescent device, the guest doping material can be selected to have excellent light-emitting performance. Taking the top-emitting device as an example, optionally, the light-emitting unit with a red light-emitting color has a light-emitting brightness of 1000 cd / m 2 The current efficiency is greater than 30cd / A, and the green luminous unit has a luminous brightness of 6000cd / m 2 The current efficiency is greater than 100cd / A, and the light-emitting unit with fluorescent blue light color has a light brightness of 1000cd / m 2 The current efficiency is greater than 5cd / A as the standard, and the appropriate guest doping material is selected. The light-emitting unit with a phosphorescent blue light color has a light-emitting brightness of 1000cd / m 2 The current efficiency is greater than 10cd / A. When the current efficiency is higher, the power consumption can be reduced.

[0117] As the light-emitting host material, one light-emitting host material or two light-emitting host materials may be selected.

[0118] Hole blocking layer:

[0119] 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.

[0120] First electron transport layer:

[0121] 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 50nm, and when there is a second electron transport layer, the thickness of the first electron transport layer is generally 40nm to 20nm. 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. It will also be because the excitons of the light-emitting layer interact with the polarons of the electron transport material. This action is likely to produce active free radicals and destroy the electron transport material. The electron transport material can be a single compound or mixed with other metals or metal compounds. It can include a mixture of organic electron transport materials and metal compounds, or a mixture of organic electron transport materials and metals.

[0122] 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.

[0123] 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.

[0124] Second electron transport layer:

[0125] 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.

[0126] 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.

[0127] 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.

[0128] Charge generation layer:

[0129] 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.

[0130] cathode:

[0131] 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.

[0132] 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.

[0133] Overlay:

[0134] The refractive index n and absorption coefficient of the single-layer cover layer need to meet the following conditions:

[0135] The refractive index between the wavelengths of 450 and 650 nm is n(450-650nm)>1.8, and the extinction coefficient between the wavelengths of 450 and 650nm is below 0.1; the extinction coefficient at 380nm is greater than 0.2; the difference between the refractive index of 450nm and the refractive index of 530nm is n(450nm)-n(530nm)<0.5, more preferably n(450nm)-n(530nm)<0.3; the difference between the refractive index of 510nm and the refractive index of 620nm is n(510nm)-n(620nm)<0.4, more preferably the difference between the refractive index of 510nm and the refractive index of 620nm is n(510nm)-n(620nm)<0.2.

[0136] The material that can meet the requirements of the cover layer for the refractive index n can further achieve high luminous efficiency of the device, while the light output efficiency and viewing angle of red light, green light and blue light are more balanced.

[0137] In some specific embodiments, the thickness of the covering layer is 50nm to 90nm, for example, 50nm, 55nm, 57nm, 59nm, 62nm, 64nm, 67nm, 68nm, 70nm, 75nm, 77nm, 79nm, 80nm, 82nm, 85nm, 88nm, 90nm, etc.

[0138] The covering layer is formed after the semi-transparent cathode of the OLED display panel is away from the substrate, so that the light transmittance of the stacked layer formed by the covering layer and the semi-transparent cathode between 450nm and 650nm is ≥65%, for example, 68%, 69%, 73%, 77%, 79%, 83%, 88%, 93%, etc.

[0139] When two layers of cover are used, the refractive index n and the absorption coefficient need to meet the following conditions:

[0140] The covering layer close to the cathode side (the first covering layer) has a refractive index n450~650nm<1.8 between 450 and 650nm, and an extinction coefficient between 450 and 650nm below 0.1; the maximum coefficient at any wavelength between 250nm and 350nm is greater than 0.3, and optimally greater than 0.6.

[0141] The covering layer (second covering layer) away from the cathode side has a refractive index n450~650nm>1.8 between 450 and 650nm, and an extinction coefficient between 450 and 650nm is below 0.1; the extinction coefficient at 380nm is greater than 0.1, and more preferably greater than 0.2.

[0142] The difference between the refractive index at 450 nm and the refractive index at 530 nm is n(450 nm)-n(530 nm)<0.5, and more preferably, the difference between the refractive index at 450 nm and the refractive index at 530 nm is n(450 nm)-n(530 nm)<0.3;

[0143] The difference between the refractive index at 510 nm and the refractive index at 620 nm is n(510 nm)-n(620 nm)<0.4, and more preferably, the difference between the refractive index at 450 nm and the refractive index at 530 nm is n(450 nm)-n(530 nm)<0.2.

[0144] The total thickness of the double-layer covering layer is 50nm to 90nm, for example: 50nm, 55nm, 57nm, 59nm, 62nm, 64nm, 67nm, 68nm, 70nm, 75nm, 77nm, 79nm, 80nm, 82nm, 85nm, 88nm, 90nm, etc.

[0145] The thickness of the covering layer (first covering layer) close to the cathode side is 5nm to 40nm, for example: 5nm, 7nm, 10nm, 12nm, 15nm, 18nm, 20nm, 22nm, 25nm, 27nm, 30nm, 32nm, 34nm, 36nm, 38nm, 40nm, etc.

[0146] The thickness of the covering layer (second covering layer) away from the cathode side is 35nm to 85nm, for example: 35nm, 40nm, 43nm, 45nm, 48nm, 50nm, 55nm, 57nm, 59nm, 62nm, 64nm, 67nm, 68nm, 70nm, 75nm, 77nm, 79nm, 80nm, 82nm, 85nm, etc.

[0147] On the other hand, the present application further provides a display device, comprising the above-mentioned organic electroluminescent device.

[0148] 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.

[0149] Common measurement instruments and methods

[0150]

Mass Spectrometry and Nuclear Magnetic Resonance

[0151] In the present application, the mass spectrum was measured by a Waters Corporation single quadrupole mass spectrometer, and the nuclear magnetic resonance was measured by a 400 MHz nuclear magnetic resonance instrument (manufactured by Bruker, Germany).

[0152]

Life measurement

[0153] (If it involves life measurement, use Flustar)

[0154]

Raw materials and reagents

[0155] The initial raw materials and solvents of the present invention were purchased from Shanghai Titan Technology Co., Ltd., some commonly used OLED intermediates and other products were purchased from domestic OLED intermediate manufacturers; various palladium catalysts, ligands, etc. were purchased from Shaanxi Ruike New Materials Co., Ltd. 1H NMR data were measured using a (400 MHz) nuclear magnetic resonance instrument (manufactured by Bruker, Germany); HPLC data were measured using a Waters Corporation UPLC ultra-high performance liquid chromatograph. LC-MS (liquid chromatography-mass spectrometry) was tested on a UPLC+SQD2 instrument from Waters Corporation.

[0156]

Cross-coupling

[0157] The synthesis of the compound represented by the above formula (1) can be carried out using known methods. For example, a cross-coupling reaction using transition metals such as nickel and palladium. Other synthesis methods are CC, CN coupling reactions using transition metals such as magnesium or zinc. The above reactions are limited to the characteristics of mild reaction conditions and superior selectivity of various functional groups, and preferably Suzuki and Buchwald reactions. The cycloalkane and heterocycloalkane derivatives of the present invention are illustrated by the following examples, but are not limited to the cycloalkane and heterocycloalkane derivatives and synthesis methods illustrated in these examples.

[0158] In an inert atmosphere, reaction A and the reactants are heated in an organic solvent in the presence of a cross-coupling catalyst (catalytic amount), and reflux heating and stirring are performed during the reaction. After the desired reaction time, the reaction system is cooled and water is added, and the precipitated solid is washed and vacuum dried to obtain a crude product. The obtained crude product is refined (including but not limited to silica gel column chromatography) to obtain a product.

[0159] Implementation

[0160] Example 1

[0161] Synthesis of compound 1

[0162]

[0163] 1) Synthesis of intermediate 1-1

[0164] Under argon atmosphere, 64.2 g (100 mmol) of reactant 1-A, 20.9 g (100 mmol) of reactant 1-B, 23.4 g (240 mmol) of sodium tert-butoxide, 575 mg (1 mmol%) of bis(dibenzylideneacetonepalladium), 348 mg (1.2 mmol%) of tri-tert-butylphosphine tetrafluoroborate and 1000 mL of xylene were added to the reaction vessel, and heated and stirred at 140°C for 15 hours. The reaction mixture was cooled to room temperature, 1000 ml of water was added, filtered, the filter cake was washed with a large amount of water, vacuum dried, and the crude product was refined by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain 56.2 g of organic compound 1-1, HPLC purity 99.3%, yield 73%. LC MS: M / Z 769.30 (M+).

[0165] Synthesis of compound 1

[0166] Except that the starting materials were replaced with intermediate 1-1 and reactant 1-C, the other operating conditions of the synthesis reaction were the same as those of the synthesis of intermediate 1-1. LC MS: M / Z 921.36 (M+). HPLC purity: 99.9%, yield: 58%.

[0167] Example 2-15

[0168] Compound 2-15 was prepared using the corresponding reactants A, B and C in Table 1 below, respectively, and referring to the synthesis method of the above compound 1. The corresponding yields and LC MS: M / Z results are shown in Table 1 below.

[0169] Table 1

[0170]

[0171]

[0172]

[0173]

[0174] Preparation of organic electroluminescent devices

[0175] Device Example 1

[0176] refer to Figure 1 , the preparation process of the device embodiment 1 of the present application is:

[0177] (1) A transparent ITO film layer (thickness 150 nm) is formed on a glass substrate 101 by magnetron sputtering to obtain a first electrode 102 as an anode.

[0178] (2) vapor depositing a mixed material of compound D-1 and compound D-2 on the surface of the anode as a hole injection layer 103, with a mixing ratio of 3:97 (mass ratio) and a thickness of 10 nm;

[0179] (3) Compound D-2 (thickness 100 nm) and compound 1 (thickness 40 nm) obtained in Example 1 were then sequentially deposited on the surface of the hole injection layer to obtain a first hole transport layer 104 and a second hole transport layer 105, respectively.

[0180] (4) Next, compound D-3, compound D-4 and compound D-5 were co-evaporated on the surface of the second hole transport layer 105 at a mass ratio of 45:45:10 to form an organic light emitting layer 106 (thickness 40 nm).

[0181] (5) Subsequently, compound D-6 was sequentially evaporated on the surface of the organic light-emitting layer to form a hole blocking layer 107 (thickness 10 nm), and compound D-7 and LiQ with a mixing ratio of 4:6 (mass ratio) were formed into an electron transport layer 108 (thickness 30 nm).

[0182] (6) Finally, magnesium (Mg) and silver (Ag) are mixed and deposited on the surface of the electron transport layer 108 at an evaporation rate of 1:9 to form a second electrode 109 with a thickness of 10 nm as a cathode, thereby completing the manufacture of the organic light-emitting device.

[0183] Device Examples 2-15

[0184] Organic electroluminescent device Example 2-15 was prepared in the same manner as in Device Example 1, except that Compound 2-15 prepared in Example 2-15 was used instead of Compound 1 when forming the second hole transport layer 105 .

[0185] Device Comparison Examples 1-4

[0186] Organic electroluminescent device comparative examples 1-4 were prepared in the same manner as device example 1, except that compound HT-A, HT-B, HT-C and HT-D were used to replace compound 1 when forming the second electron transport layer 105.

[0187] The compounds involved in the preparation process of device examples 1-15 and device comparative examples 1-4 are shown in Table 2 below.

[0188] Table 2

[0189]

[0190]

[0191] The operating voltage and efficiency of the organic electroluminescent device prepared above were calculated by a computer-controlled Keith ley 2400 test system. The device life under dark conditions was obtained using a Foster life measurement system equipped with a power supply and a photodiode as a detection unit. Each group of device embodiments and device comparative example 1 were produced and tested in the same batch as the device of device embodiment 1, and the operating voltage, efficiency and life of the device of device comparative example 1 were recorded as 1, and the ratios of the corresponding indicators of device embodiments 1 to 15, device comparative examples 1-4 and device comparative example 1 were calculated, as shown in Table 3.

[0192] The device test results are shown in Table 3 below.

[0193] Table 3

[0194]

[0195]

[0196] As can be seen from Table 3, the structures of the device embodiments and the device comparative examples are consistent except for the different hole transport materials. Compared with the comparative examples, the voltage of device embodiments 1-15 is significantly reduced, and the device efficiency and life are greatly improved. The inventors of the present application believe that the reason behind this is caused by the molecular structure of the organic compound of the embodiment of the present application. From the molecular structure point of view, on the one hand, two aromatic amine systems are introduced into the core benzene ring structure, and the molecular conjugation increases, which can improve the stability of the molecule, can reduce the operating voltage of the device, and improve or ensure the life of the device; on the other hand, two dibenzofuran structures are also introduced, the molecular planarity increases, and the intermolecular stacking is better, which can reduce the unnecessary transmission of electrons between molecules and improve the mobility of the material, especially as a hole transport layer, which can significantly increase the hole mobility of the device and improve the efficiency of the device.

[0197] It should be understood that although this specification is described according to implementation modes, not every implementation mode contains only one independent technical solution. This description of the specification is only for the sake of clarity. Those skilled in the art should regard the specification as a whole. The technical solutions in each implementation mode may also be appropriately combined to form other implementation modes that can be understood by those skilled in the art.

[0198] The series of detailed descriptions listed above are only specific descriptions of feasible implementation methods of the present invention. They are not intended to limit the scope of protection of the present invention. Any equivalent implementation methods or changes that do not deviate from the technical spirit of the present invention should be included in the scope of protection of the present invention.

Claims

1. An organic compound, wherein The organic compound has the following structural formula (I): In the formula (I), L1, L2 and L3 are each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C1-C30 heteroarylene group; Ar1 and Ar2 are the same or different, and are each independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C1-C30 heteroaryl group, or they are bonded to adjacent atoms to form a ring.

2. The organic compound according to claim 1, characterized in that: Ar1 and Ar2 are each independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, spirofluorenyl, spirofluorenyloxanthryl, spirofluorenylazaanthryl, dibenzofuranyl, dibenzothiophenyl, naphthyl, phenanthryl, or a combination of several thereof, or are bonded to adjacent atoms to form a ring; Preferably, the dimethylfluorenyl is 9,9-dimethylfluorenyl; preferably, the diphenylfluorenyl is 9,9-diphenylfluorenyl; preferably, the spirofluorenyl is 9,9'-spirobifluorenyl; preferably, the spirofluorenyloxanthracene is spiro[fluorene-9,9'-oxanthracene]yl; preferably, the spirofluorenylazaanthracenyl is spiro[fluorene-9,9'-azaanthracenyl].

3. The organic compound according to claim 1, characterized in that: The L1, L2 and L3 are each independently selected from a single bond or a substituted or unsubstituted group: phenylene, biphenylene, naphthylene, dimethylfluorenylene, diphenylfluorenylene, spirofluorenylene, spirofluorenylene oxanthracenylene, spirofluorenylene azaanthrylene or a combination thereof, or bonded to adjacent atoms to form a ring; Preferably, the dimethylfluorenylene is 9,9-dimethylfluorenylene; preferably, the diphenylfluorenylene is 9,9-diphenylfluorenylene; preferably, the spirofluorenylene is 9,9'-spirobifluorenylene; preferably, the spirofluorenylene xanthracene is spiro[fluorene-9,9'-xanthracene]yl; preferably, the spirofluorenylene azaanthryl is spiro[fluorene-9,9'-azaanthryl]yl; Preferably, at least one of L1, L2 and L3 is a single bond.

4. The organic compound according to any one of claims 1 to 3, characterized in that: The substituent in the "substituted" is selected from substituted or unsubstituted straight or branched alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, aryl groups having 6 to 15 carbon atoms, and heteroaryl groups having 3 to 15 carbon atoms.

5. The organic compound according to claim 1, characterized in that: The structural formula of the organic compound is selected from any one of the following structural formulas: Wherein, Ar2 is independently selected from one or a combination of phenyl, biphenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, spirofluorenyl, spirofluorenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, naphthyl, phenanthryl, or a combination of several thereof, or is bonded to adjacent atoms to form a ring; The L1 is selected from a single bond or a substituted or unsubstituted group: phenylene, biphenylene, naphthylene, dimethylfluorenylene, diphenylfluorenylene, spirofluorenylene, spirofluorenylene oxanthracenylene, spirofluorenylene azaanthrylene or a combination thereof, or bonds with adjacent atoms to form a ring; Preferably, the dimethylfluorenyl is 9,9-dimethylfluorenyl; preferably, the diphenylfluorenyl is 9,9-diphenylfluorenyl; preferably, the spirofluorenyl is 9,9'-spirobifluorenyl; preferably, the spirofluorenyloxanthracene is spiro[fluorene-9,9'-oxanthracene]yl; preferably, the spirofluorenylazaanthracenyl is spiro[fluorene-9,9'-azaanthracenyl].

6. The organic compound according to claim 5, characterized in that: The structural formula of the organic compound is selected from any one of the following structural formulas:

7. An organic material, characterized in that The organic material comprises the organic compound according to any one of claims 1 to 6.

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

9. An organic electroluminescent device, comprising a first electrode, a second electrode and at least one organic functional layer located between the first electrode and the second electrode, the organic functional layer comprising the organic compound as described in any one of claims 1 to 6 or the organic material as described in claim 7; preferably, the organic functional layer is selected from a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer or an electron transport layer; more preferably, the hole transport layer comprises the organic compound as described in any one of claims 1 to 6 or the organic material as described in claim 7.

10. An electronic device, characterized in that: The electronic device comprises the organic electroluminescent device as claimed in claim 9; preferably, the electronic device is a display or lighting device.

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