Organic compound, organic layer and application thereof, and organic electroluminescent device

Abstract

The invention discloses an organic compound, an organic layer, application of the organic layer and an organic electroluminescent device, and relates to the technical field of organic electroluminescent materials.The general formula of the organic compound is shown in a formula I-1 or a formula I-2. The organic compound has a large plane conjugated structure, has good charge transfer capacity, is stable in molecular structure and can be used for preparing organic electroluminescent materials. When the compound is applied to an organic electroluminescent device, the efficiency of the device can be improved, the service life of the device can be prolonged, and the working voltage of the device can be reduced.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescent materials technology, specifically to an organic compound, an organic layer and its uses, and an organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are a class of self-emissive electronic devices that convert electrical energy into light energy. They have attracted widespread attention from academia and industry because they can emit light with high brightness at low driving voltage and can emit multiple colors by selecting light-emitting materials.

[0003] Currently, many OLED functional materials have been developed to improve device performance, but they still cannot meet market demand. Therefore, there is a continuous need to develop functional materials with low voltage drive, high efficiency and long lifespan. Summary of the Invention

[0004] The technical problem addressed by this application is to improve the performance of organic electroluminescent devices.

[0005] To solve the above-mentioned technical problems, this application provides the following technical solution:

[0006] In a first aspect, this application provides an organic compound, the general formula of which is shown in Formula I-1 or Formula I-2:

[0007]

[0008] Wherein: A is absent, or when A is present, A is selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C5-C18 heteroaryl groups; n is selected from 1, 2, or 3; Rp1, Rq1, Rp2, and Rq2, each time appearing, are selected from the same or different groups or combinations thereof: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, thiocyanate (-SCN), isocyanate (-OCN), pentafluorosulfonyl (-SF5), sulfinyl, sulfonyl, phosphoxy, hydroxyl, mercapto, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C1-C2... 0 is a heteroalkyl group, a substituted or unsubstituted C3-C20 heterocyclic group, a substituted or unsubstituted C7-C30 aralkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C3-C20 silyl group, a substituted or unsubstituted C6-C20 arylsilyl group, a substituted or unsubstituted C3-C20 alkylgermanium group, a substituted or unsubstituted C6-C20 arylgermanium group; and Rp2 and Rq2 can form rings.

[0009] In a second aspect, this application provides an organic layer comprising any of the organic compounds described above.

[0010] In a third aspect, this application provides the use of any of the organic compounds or organic layers described above in organic electroluminescent devices.

[0011] In a fourth aspect, this application provides an organic electroluminescent device, including a first electrode, a second electrode, and the aforementioned organic layer located between the first electrode and the second electrode.

[0012] The organic compound of this application comprises dicyanopyrazine and thiophene sulfone structural fragments, resulting in a large planar conjugated structure that facilitates charge transport. Furthermore, the molecular structure of this organic compound is stable. When applied to organic electroluminescent devices, it can improve device efficiency and lifespan while reducing operating voltage. Moreover, when the dicyanopyrazine and thiophene sulfone structural fragments are distributed around an aryl or heteroaryl group, the operating voltage of the device can be further reduced, and the device efficiency and lifespan extended. Attached Figure Description

[0013] The following accompanying drawings describe in detail the exemplary embodiments disclosed in this application. The same reference numerals denote similar structures in several views of the drawings. Those skilled in the art will understand that these embodiments are non-limiting and exemplary, and the drawings are for illustrative purposes only and are not intended to limit the scope of this application. Other embodiments may similarly fulfill the inventive intent of this application. It should be understood that the drawings are not drawn to scale. Wherein:

[0014] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device prepared in Example 20 of this application;

[0015] Figure 2 This is a schematic diagram of the structure of the organic electroluminescent device prepared in Example 39 of this application. Detailed Implementation

[0016] The following description provides specific application scenarios and requirements for this application, intended to enable those skilled in the art to make and use the content of this application. Various partial modifications to the disclosed embodiments will be apparent to those skilled in the art, and the general principles defined herein can be applied to other embodiments and applications without departing from the spirit and scope of this application. Therefore, this application is not limited to the embodiments shown, but rather to the widest scope consistent with the claims.

[0017] The following is a detailed explanation of some terms used in this application:

[0018] Substituted or unsubstituted: refers to substitution with one or more substituents, or no substitution at all. Substituents may be selected from the following: deuterium, halogen, fluorine, trifluoromethyl, cyano, nitro, hydroxyl, carbonyl, ester, imide, amino, phosphoxy, alkoxy, aryloxy, sulfone, sulfoxide, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, heteroaryl, aralkyl, arylenyl, alkylaryl, alkylamine, aralkylamine, heteroarylamine, arylamine, arylphosphinyl, heterocyclic, carboxyl derivative groups; or substitution with a substituent that connects to two or more substituents listed above. For example, "a substituent that connects to two or more substituents" may include biphenyl, i.e., biphenyl may be aryl, or a substituent that connects to two phenyl groups. When substituted with two or more substituents, adjacent substituents may also bond to form a ring. As an example, cyclization can be achieved through chemical bonding or through fusion.

[0019] Aryl group: Not particularly limited, it can be monocyclic or polycyclic aryl. In some embodiments, monocyclic aryl includes, but is not limited to, phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, etc. Polycyclic aryl includes, but is not limited to, naphthyl, anthracene, phenanthryl, pyrene, perylene, fluorene, etc. The fluorene group can be substituted, such as 9,9'-dimethylfluorenel, 9,9'-dibenzofluorenel, etc. In addition, two of the substituents can combine with each other to form a spirocyclic structure, such as 9,9'-spirodifluorenel, etc.

[0020] The above description of aryl groups can be applied to aryl groups in the following categories: aryloxy, arylsilyl, arylgermanium, arylthio, arylsulfonyl, arylphosphinyl, arylalkyl, arylalkylamine, arylenyl, alkylaryl, arylamine, and arylheteroarylamine.

[0021] Heteroaryl groups: Containing one or more of B, N, O, P, S, Si, and Se as heteroatoms. Heteroaryl groups include, but are not limited to, pyridinyl, pyrrolyl, pyrimidinyl, pyridazinyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, azole, isozolyl, thiazolyl, isothiazolyl, triazolyl, diazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiaranyl, pyrazinyl, azinyl, thiazolyl, dioxazinyl, dioxazinyl, triazinyl, tetraazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphridinyl, acridineyl, xanthyl, phenanthridineyl, diazanaphthyl, triazaindenyl, indoleyl, dihydroindoleyl, nitro-indenyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl Pyrazinyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzothiophene, benzofuranyl, dibenzothiophene, dibenzofuranyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, indocarbazoleyl, phenazinyl, imidazopyridyl, phenazinyl, phenanthrinyl, phenthiazolyl, imidazopyridyl, imidazophenanthrinyl, benzoimidazoquinazolinyl, benzoimidazophenanthrinyl, spiro[fluorene-9,9'-oxazanthracene], phenylbinaphthyl, dinaphthofuranyl, naphthobenzofuranyl, dinaphthiophene, naphthobenzothiophene, triphenylphosphine oxide, triphenylborane, etc.

[0022] The above description of heteroaryl groups can be applied to heteroaryl groups in heteroaryl amines and aryl heteroaryl amines.

[0023] Alkyl groups: may be straight-chain 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.

[0024] The above description of alkyl groups can also be used for alkyl groups in aralkyl, alkylgermanium, aralkylamine, alkylaryl, and alkylamine groups.

[0025] Heteroalkyl: can be a straight-chain or branched alkyl group containing heteroatoms, and the number of carbon atoms is not particularly limited. In some embodiments, heteroalkyl includes, but is not limited to, alkoxy, alkylthio, alkylsulfonyl, etc. Alkoxy may include, for example, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc. Alkylthio groups can include, for example, methylthio, ethylthio, n-propylthio, isopropylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, n-hexylthio, 3,3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio, etc.

[0026] Cycloalkyl groups: also known as cyclic saturated hydrocarbon groups, 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.

[0027] Heterocyclic alkyl groups: cycloalkyl groups containing heteroatoms, for example: wait.

[0028] Through extensive research, the inventors of this application have discovered that when dicyanopyrazine and thiophene sulfone structures appear simultaneously in the same compound molecule, the compound can possess excellent charge transport properties and good thermal stability, which can significantly improve device performance when used to prepare organic electroluminescent devices.

[0029] Based on this, this application provides an organic compound in a first aspect, the organic compound having a structural formula including a dicyanopyrazine structural fragment and a thiophene sulfone structural fragment, having a general formula as shown in Formula I-1 or Formula I-2:

[0030]

[0031] Wherein: A is absent, or when A is present, A is selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C5-C18 heteroaryl groups; n is selected from 1, 2, or 3; Rp1, Rq1, Rp2, and Rq2, each time appearing, are selected from the same or different groups or combinations thereof: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, thiocyanate, isocyanate, pentafluorosulfonyl, sulfinyl, sulfonyl, phosphoxy, hydroxyl, mercapto, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or Unsubstituted C3–C20 heterocyclic groups, substituted or unsubstituted C7–C30 aralkyl groups, substituted or unsubstituted C1–C20 alkoxy groups, substituted or unsubstituted C6–C30 aroxy groups, substituted or unsubstituted C2–C20 alkenyl groups, substituted or unsubstituted C2–C20 alkynyl groups, substituted or unsubstituted C6–C30 aryl groups, substituted or unsubstituted C3–C30 heteroaryl groups, substituted or unsubstituted C3–C20 silyl groups, substituted or unsubstituted C6–C20 arylsilyl groups, substituted or unsubstituted C3–C20 alkylgermanium groups, substituted or unsubstituted C6–C20 arylgermanium groups; and Rp2 and Rq2 can form rings.

[0032] In some preferred embodiments, in Formula I-1, at least one of Rp1 and Rq1 is a group having an electron-withdrawing group.

[0033] In some preferred embodiments, in Formula I-2, at least one of Rp2 and Rq2 is a group having an electron-withdrawing group.

[0034] Electron-withdrawing groups, also known as electron-withdrawing groups, are groups that can attract electrons, thereby reducing the electron cloud density of the atoms or groups attached to them. Examples include cyano groups and trifluoromethyl groups.

[0035] In some preferred embodiments, the general formula of the organic compound is as shown in Formula I-1, where A is absent and n is 1; the organic compound is represented by Formula II: R1 is defined the same as Rp1 mentioned above, and R2 is defined the same as Rq1 mentioned above.

[0036] More preferably, the structural formula of the organic compound is selected from the group consisting of:

[0037]

[0038] R2 is selected from

[0039] More preferably, the organic compound is selected from the group consisting of:

[0040]

[0041] In some preferred embodiments, the general formula of the organic compound is shown in Formula I-2, and in Formula I-2, A is selected from phenyl, phenanthrene, phenanthrene and cyclosulfonyl fused groups; n is 2.

[0042] In some preferred embodiments, the organic compound is represented by any of the following structural formulas:

[0043]

[0044]

[0045] Among them, R3~R 35 Each time it appears, it is selected from the same or different groups or combinations thereof: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, thiocyanate, isocyanate, pentafluorosulfonyl, sulfinyl, sulfonyl, phosphoxy, hydroxyl, mercapto, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C3-C20 heterocyclic, substituted or unsubstituted C7-C30 aralkyl. Substituted or unsubstituted C1–C20 alkoxy groups, substituted or unsubstituted C6–C30 aryloxy groups, substituted or unsubstituted C2–C20 alkenyl groups, substituted or unsubstituted C2–C20 alkynyl groups, substituted or unsubstituted C6–C30 aryl groups, substituted or unsubstituted C3–C30 heteroaryl groups, substituted or unsubstituted C3–C20 silyl groups, substituted or unsubstituted C6–C20 arylsilyl groups, substituted or unsubstituted C3–C20 alkylgermanium groups, and substituted or unsubstituted C6–C20 arylgermanium groups.

[0046] More preferably, the organic compound is represented by Formula III, and the structural formula of the organic compound is selected from the group consisting of:

[0047]

[0048] Among them, R4 is selected from CN, R5 is selected from CN.

[0049] More preferably, the organic compound is represented by formula IV, and the structural formula of the organic compound is selected from the group consisting of:

[0050]

[0051] Among them, R 10 Selected from R7, R9, R 12 R 13 Selected independently from H and CN.

[0052] More preferably, the organic compound is represented by formula V, and the structural formula of the organic compound is selected from the group consisting of:

[0053]

[0054]

[0055] Among them, R 19 Selected from R 20 and R 21 Selected independently from H, F, and CN.

[0056] More preferably, the organic compound is represented by formula VII, and the structural formula of the organic compound is selected from the group consisting of:

[0057]

[0058] Among them, R 33 Selected from F, CN, NO2, H; R 34 Selected from CN.

[0059] More preferably, the organic compound is selected from the group consisting of:

[0060]

[0061] In a second aspect, this application provides an organic layer comprising the aforementioned organic compound.

[0062] In a third aspect, this application provides the use of the aforementioned organic compound or organic layer in an organic electroluminescent device, wherein the organic compound or organic layer can improve the performance of the organic electroluminescent device.

[0063] This application provides an organic electroluminescent device in a fourth aspect, comprising a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode. As an example, the first electrode is an anode, and the second electrode is a cathode; the cathode may be one or more layers. The organic layer may be a single-layer structure or a multilayer tandem structure with two or more organic layers laminated together. The organic layer may include at least one organic functional layer selected from the following: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; each organic functional layer may be a single layer or multiple layers.

[0064] When an organic electroluminescent device employs a single-layer light-emitting layer, holes and electrons are injected from the anode and cathode, respectively, eliminating the need for a charge-generating layer. As an example, the organic electroluminescent device can be constructed in one of the following ways:

[0065] (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.

[0066] (2) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode.

[0067] (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.

[0068] (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.

[0069] (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.

[0070] (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.

[0071] (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.

[0072] (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.

[0073] (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.

[0074] (10) Anode / hole injection layer / hole transport layer / electron blocking layer / light emission layer / electron transport layer / electron injection layer / cathode.

[0075] (11) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode.

[0076] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode.

[0077] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode.

[0078] (14) Anode / hole injection layer / hole transport layer / light emission layer / hole blocking layer / electron transport layer / electron injection layer / cathode.

[0079] (15) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode.

[0080] The light emission direction of the organic electroluminescent device can be either from the anode side or the cathode side. When emitting light from the cathode side, the difference from structures (1) to (15) is that a cover layer needs to be added to the cathode side.

[0081] When an organic light-emitting device uses two or more light-emitting layers, a charge-generating layer needs to be set between the light-emitting layers to achieve the effects of charge generation, injection, and transport. Taking two light-emitting layers as an example, the structure of the organic light-emitting device can be: anode / first hole injection layer / first hole transport layer / first electron blocking layer / first light-emitting layer / first hole blocking layer / first electron transport layer / charge-generating layer (n-type + p-type) / second hole transport layer / second electron blocking layer / second light-emitting layer / second hole blocking layer / second electron transport layer / cathode.

[0082] The following describes some specific functional layers in the organic electroluminescent device.

[0083] Substrate:

[0084] The substrate is generally located below the anode. The substrate can be made of plastic or glass, and can be rigid or flexible. The substrate has a driving unit that can drive the corresponding pixel to emit light.

[0085] anode:

[0086] Organic EL (Organic Electro-Luminescence) devices typically require the anode to have good conductivity, a smooth surface, and be resistant to cracking. They also have certain requirements for work function, mainly to match the hole injection layer and achieve the hole injection effect.

[0087] When using a top-emitting method (cathode-side light emission), the anode is a metal compound with a work function of 4.2 eV or higher, such as indium tin oxide, tin oxide, indium zinc oxide, gold, silver, platinum, copper, carbon nanotubes, carbon nanowires, graphene, etc. The thickness is 10 nm to 200 nm, preferably 10 nm to 50 nm. A reflective electrode is placed below the anode (near the substrate end). The reflective electrode is generally made of metal or metal alloy, such as silver, copper, aluminum, gold, or alloys of these metals with other metals. The reflective electrode has high reflectivity, requiring a reflectivity of over 90%, and its thickness is typically between 100 nm and 500 nm, preferably in the range of 80 nm to 150 nm.

[0088] When bottom-emitting (substrate-side light emission) is used, the anode is a metal compound with a work function of 4.2 eV or higher, such as indium tin oxide, tin oxide, indium zinc oxide, gold, silver, platinum, copper, carbon nanotubes, carbon nanowires, graphene, etc. The thickness is 10 nm to 1 μm, preferably 50 nm to 200 nm.

[0089] The anode can be made by forming a thin film from the electrode material using methods such as vapor deposition, sputtering, or coating.

[0090] Hole injection layer:

[0091] The thickness of the hole injection layer is typically 3 nm to 20 nm. The hole injection layer uses a mixture of P-type and hole transport materials. The purpose of using P-type materials is to accept holes from the anode and transfer them to the hole transport material. The weight percentage of P-type materials in the hole injection layer is typically 0.5% to 10%. When the weight percentage 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 must not exceed 0.3 eV. When the weight percentage 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 must not exceed 0.5 eV. When the weight percentage 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 must not exceed 1 eV.

[0092] P-type materials can be metal oxides, such as molybdenum oxide, vanadium oxide, tungsten oxide, etc.; or organic compounds, such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl) (PD1, CAS No.: 1224447-88-4), tetracyanoquinone dimethyl (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), and are not limited thereto. Compared with the above-mentioned existing materials, when the P-type material adopts the organic compound shown in Formula I-1 or Formula I-2 of this application, the performance of organic electroluminescent devices can be effectively improved.

[0093] The hole transport material used in conjunction with the P-type material can be selected from the material of the second hole transport layer, and can be the same as or different from the material of the second hole transport layer.

[0094] First hole transport layer:

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

[0096] Second hole transport layer:

[0097] The thickness of the second hole transport layer is generally 10nm to 150nm, and it often uses aryl amine compounds, such as monoaryl amines or polyaryl amines.

[0098] Electron blocking layer:

[0099] The electron blocking layer can simultaneously possess both hole transport and electron blocking functions. Furthermore, the higher triplet excitation energy level of the electron blocking layer can confine excitons generated in the emissive layer within it, thereby improving the device's luminous efficiency.

[0100] Emissive layer:

[0101] The materials of the light-emitting layer generally include a host material and a dopant material, with the content of the host material being greater than that of the dopant material.

[0102] Cavity blocking layer:

[0103] To enhance the balance between hole and electron concentrations, a hole blocking layer is inserted to balance carrier concentration and prevent exciton quenching. Typically, the hole blocking layer is located between the emitting layer and the electron transport layer, and the hole blocking layer material must meet conditions such as high stability, good film-forming properties, and a sufficiently high highest molecular occupied orbital.

[0104] First electron transport layer:

[0105] The thickness of the first electron transport layer can typically be 3nm–40nm, 3nm–10nm, 10nm–20nm, 20nm–30nm, 30nm–40nm, or 20nm–40nm. When there is no second electron transport layer, the thickness of the first electron transport layer is typically 20nm–40nm; when there is a second electron transport layer, the thickness of the first electron transport layer is typically 30nm–20nm. The first electron transport layer is in direct contact with the emitting layer, and therefore, similar to the first hole transport layer, it also undergoes electronic changes during electron transport, leading to increased molecular vibration and deformation. Furthermore, the interaction between the excitons of the emitting layer and the polarons of the electron transport material can easily generate reactive free radicals, which can damage the electron transport material. Electron transport materials can be single compounds or mixtures with other metal compounds, such as Liq.

[0106] Second electron transport layer:

[0107] The thickness of the second electron transport layer is generally 10 nm to 40 nm. The material of the second electron transport layer may include a mixture of organic electron transport materials and metal compounds, or a mixture of organic electron transport materials and metals.

[0108] When organic electron transport materials are mixed with metal compound materials, such as alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds, more specifically, they can be mixed with lithium metal compounds, calcium metal compounds, Mg metal compounds, samarium metal compounds, ytterbium metal compounds, etc., and even more specifically, they can be mixed with lithium 8-hydroxyquinoline, lithium fluoride, magnesium fluoride, ytterbium fluoride, calcium fluoride, etc. When used in combination with metal compounds, the mass percentage of the organic electron transport material can be 20%–80%, 20%–40%, 40%–60%, or 60%–80%, etc.

[0109] When organic electron transport materials are used in combination with metals, such as alkali metals, alkaline earth metals, and rare earth metals, or more specifically, with lithium metal, magnesium metal, calcium metal, ytterbium metal, and samarium metal, the mass ratio of the organic electron transport material can be 80%–99%, 80%–89%, 89%–99%, 80%–85%, 85%–90%, 90%–95%, or 95%–99%, etc.

[0110] Electron injection layer:

[0111] The electron injection layer can lower the potential barrier for electrons to be injected from the cathode into the organic layer, improve electron injection efficiency, and thus optimize device performance. The selection of materials for 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 or coordination compounds.

[0112] Charge generation layer:

[0113] When using double or multiple light-emitting layers, a charge-generating layer is disposed between the two light-emitting layers. This layer is typically composed of two P / N type materials, where the P-type material can be selected from the hole injection materials mentioned earlier. In particular, when the P-type material of the charge-generating layer is an organic compound as shown in Formula I-1 or Formula I-2 of this application, the performance of the organic electroluminescent device can be effectively improved.

[0114] The N-type material of the charge generation layer is a mixture of organic electron transport material and metal. The organic electron transport layer material is selected from the second electron transport layer mentioned earlier, and the metal is selected from alkali metals, alkaline earth metals, rare earth metals, and more specifically, lithium, magnesium, calcium, ytterbium, and samarium. When the organic electron transport material is mixed with the metal, the mass ratio of the organic electron transport material can be 80%–99%, 80%–89%, 89%–99%, 80%–85%, 85%–90%, 90%–95%, or 95%–99%, etc.

[0115] cathode:

[0116] The cathode requires materials with good electrical conductivity and a smooth surface. To improve electron injection capability, materials with a low work function are typically chosen. Cathode materials can be single-layer, double-layer, or multi-layer cathodes, generally made of metals or metal alloys. For single-layer cathodes, silver, copper, aluminum, gold, or alloys of these metals with other metals, such as rare earth metals, alkali metals, and alkaline earth metals, can be used. Examples include magnesium-indium alloys, magnesium-aluminum alloys, aluminum-potassium alloys, aluminum-scandium-potassium alloys, magnesium-silver alloys, silver-ytterbium alloys, and silver-samarium alloys. If a double-layer metal cathode is used, the cathode layer closer to the light-emitting layer can be made of alkali metals, alkaline earth metals, or rare earth metals, such as lithium, calcium, magnesium, and ytterbium, to increase electron injection capability. The cathode layer farther from the light-emitting side is mainly used to improve conductivity, and generally uses silver, copper, aluminum, gold, or alloys of these metals with other metals, such as alloys with rare earth metals, alkali metals, or alkaline earth metals. Examples include magnesium-indium alloys, magnesium-aluminum alloys, aluminum-potassium alloys, aluminum-scandium-potassium alloys, magnesium-silver alloys, silver-ytterbium alloys, and silver-samarium alloys. The cathode can also be formed into a thin film using methods such as vapor deposition or sputtering.

[0117] When light comes out from the anode side, the cathode must be opaque, and a cathode with a thickness greater than 100 nm can be deposited. When light comes out from the cathode side, the cathode must be transparent, with a transmittance greater than 40% and a thickness of 10 nm to 20 nm.

[0118] Overlay:

[0119] When light exits from the cathode side, photons resonate with electrons in the cathode metal, reducing the light extraction efficiency. Adding a capping layer on the side of the cathode furthest from the light-emitting layer can reduce this effect and effectively improve the light efficiency. When adding a capping layer, a capping layer material with high refractive index and low absorption coefficient should be used directly. For example, a material with a refractive index greater than 1.9 and an absorption rate less than 0.01% at a wavelength of 460 nm is preferred, a material with a refractive index greater than 2.0 and an absorption rate less than 0.01% at a wavelength of 460 nm is preferred, and a material with a refractive index greater than 2.1 and an absorption rate less than 0.01% at a wavelength of 460 nm is even more preferred.

[0120] The technical solution of this application will be clearly and completely described below with reference to the embodiments of this application. Unless otherwise specified, the reagents and raw materials used can be purchased commercially. Experimental methods in the following embodiments that do not specify specific conditions are generally determined according to national standards. If there is no corresponding national standard, then general international standards, conventional methods and conditions, or conditions recommended by the manufacturer, or the product instructions shall be followed. Unless otherwise stated, all parts are parts by weight, and all percentages are weight percentages.

[0121] The initial raw materials and solvents used in the following examples were purchased from Sinopharm, some commonly used OLED intermediates were purchased from domestic OLED intermediate manufacturers, and various ligands were purchased from Sigma-Aldrich. HPLC data were determined using a Shimadzu LC 20AD high-performance liquid chromatograph; LC-MS (liquid chromatography-mass spectrometry) was performed on a Waters Corporation H-class+SQD2 instrument.

[0122] Compound Examples

[0123] Example 1

[0124] Synthesis of Compound 1

[0125]

[0126] 1) Synthesis of intermediate 1-1

[0127] 27.2 g (100 mmol) of compound 1-A, 29.2 g (200 mmol) of compound 1-B, and 300 mL of anhydrous ethanol were added to a reaction vessel, and the mixture was heated under reflux at 90 °C for 24 hours. The reaction mixture was cooled to room temperature, and after concentrating to remove some of the solvent, crystals were precipitated by cooling. The crystals were filtered, dried under vacuum, and 27.6 g of intermediate 1-1 was obtained with an HPLC purity of 98.2% and a yield of 85%. LC-MS: M / Z 325.8 (M+).

[0128] 2) Synthesis of intermediates 1-2

[0129] 22.1 g (80 mmol) of intermediate 1-1 and 200 mL of trifluoroacetic acid were added to a reaction vessel. The mixture was cooled in an ice-water bath, and 27.2 g (400 mmol) of 50% hydrogen peroxide was slowly added dropwise. After the addition was complete, the mixture was gradually brought back to room temperature and stirred for 24 hours. 1000 mL of water was added, and the mixture was filtered. The filter cake was washed with plenty of water and dried under vacuum to obtain 20.0 g of intermediate 1-2 with an HPLC purity of 97.7% and a yield of 77%. LC-MS: M / Z 357.8 (M+).

[0130] 3) Synthesis of intermediates 1-3

[0131] 17.9 g (50 mmol) of intermediate 1-2, 31.6 g (105 mmol) of compound 1-C, 15.9 g (150 mmol) of sodium carbonate, 1.5 g (2.1 mmol) of Pd(PPh3)2Cl2, 300 mL of toluene, 100 mL of ethanol, and 100 mL of water were added to a reaction vessel. The reaction system was purged with nitrogen three times, heated to 85 °C under reflux for 5 hours, cooled, filtered, and the solid intermediate product was recrystallized, filtered, and the filter cake was dried under vacuum to obtain 23.8 g of intermediate 1-3 with an HPLC purity of 98.9% and a yield of 87%. LC-MS: M / Z 546.0 (M+).

[0132] 4) Synthesis of intermediates 1-4

[0133] 21.9 g (40 mmol) of intermediate 1-3, 11.1 g (105 mmol) of sodium carbonate, 25.8 g (80 mmol) of tetrabutylammonium bromide, 34.4 g (80 mmol) of phosphorus pentabromide, and 200 mL of xylene were added to a reaction vessel. The reaction system was purged with nitrogen three times, heated to 145 °C under reflux for 2 hours, cooled to room temperature, and saturated ammonium chloride aqueous solution was added dropwise. The mixture was filtered, and the crude solid intermediate was recrystallized, filtered, and the filter cake was dried under vacuum to give 16.1 g of intermediate 1-4 with an HPLC purity of 98.3% and a yield of 60%. LC-MS: M / Z 671.8 (M+).

[0134] 5) Synthesis of Compound 1

[0135] 16.1 g (24 mmol) of intermediate 1-4, 200 mL of acetonitrile, and 3.1 g (48 mmol) of potassium cyanide were added to a reaction vessel, and the mixture was stirred at room temperature for 24 hours. 500 mL of ice-cold brine was added, the mixture was cooled, filtered, the filter cake was washed with water, recrystallized, filtered again, and the filter cake was dried under vacuum to give 7.4 g of compound 1, with an HPLC purity of 99.5% and a yield of 55%. LC-MS: M / Z 564.2 (M+).

[0136] Examples 2-5

[0137] Compounds 2 to 5 shown in Table 1 were prepared according to the preparation method in Example 1.

[0138] Table 1. Raw materials and product compounds

[0139]

[0140]

[0141] Examples 6 to 12

[0142] Compounds 6–12 shown in Table 2 were prepared according to the preparation method in Example 13 below.

[0143] Example 13

[0144] Synthesis of Compound 13

[0145]

[0146] 1) Synthesis of intermediate 13-1

[0147] 37.8 g (100 mmol) of compound 13-A and 500 mL of glacial acetic acid were added to a reaction vessel, and the mixture was heated to 60 °C. 86.3 g (500 mmol) of m-chloroperoxybenzoic acid was added in portions, and the reaction was continued for 2 hours after the addition was complete. The reaction mixture was cooled to room temperature, and 1000 mL of ice water was added to induce crystallization. The crystals were filtered, the filter cake was washed with water, and the product was dried under vacuum to give 36.7 g of intermediate 13-1, with an HPLC purity of 97.6% and a yield of 83%. LC-MS: M / Z 441.8 (M+).

[0148] 2) Synthesis of intermediate 13-2

[0149] 35.4 g (80 mmol) of compound 13-1, 9.5 g (88 mmol) of compound 13-B, 1000 mL of anhydrous ethanol, and 20 mL of glacial acetic acid were added to a reaction vessel, and the mixture was heated under reflux for 12 hours. Crystallization was observed upon cooling, followed by filtration. The filter cake was washed with glacial ethanol and dried under vacuum to give 35.0 g of intermediate 13-2, with an HPLC purity of 98.3% and a yield of 85%. LC-MS: M / Z 513.8 (M+).

[0150] 3) Synthesis of intermediate 13-3

[0151] 33.4 g (65 mmol) of intermediate 13-2, 41.1 g (136.5 mmol) of compound 1-C, 20.7 g (195 mmol) of sodium carbonate, 1.8 g (2.6 mmol) of Pd(PPh3)2Cl2, 1000 mL of dioxane, and 300 mL of water were added to a reaction vessel. The reaction system was purged with nitrogen three times, heated to 105 °C under reflux for 16 hours, cooled, filtered, and the filter cake was washed with dioxane and water. The filter cake was then vacuum dried to obtain 40.2 g of intermediate 13-3 with an HPLC purity of 98.5% and a yield of 88%. LC-MS: M / Z 702.2 (M+).

[0152] 4) Synthesis of intermediate 13-4

[0153] 38.7 g (55 mmol) of intermediate 13-3 and 800 mL of DMF were added to a reaction vessel, heated to 40 °C, and 25.7 g (143 mmol) of NBS was added in portions. The reaction was maintained at this temperature for 2 hours, then cooled to room temperature. The mixture was slowly poured into 1600 mL of ice water with stirring, and stirred to crystallize for 1 hour. The mixture was filtered, and the filter cake was washed successively with water and ethanol, and dried under vacuum to obtain 40.7 g of intermediate 13-4 with an HPLC purity of 99.1% and a yield of 86%. LC-MS: M / Z 859.8 (M+).

[0154] 5) Synthesis of Compound 13

[0155] 21.5 g (25 mmol) of intermediate 13-4, 8.3 g (25 mmol) of potassium ferricyanide, 5.8 g (60 mmol) of potassium acetate, 0.68 g (0.75 mmol) of Pd2(dba)3, 0.87 g (1.5 mmol) of XantPhos, 300 mL of dioxane, and 200 mL of water were added to a reaction vessel and stirred under reflux for 5 hours. The mixture was cooled, 500 mL of ice-cold brine was added, and the mixture was filtered. The filter cake was recrystallized to give 11.9 g of compound 13, with an HPLC purity of 99.5% and a yield of 63%. LC-MS: M / Z 752.0 (M+).

[0156] Examples 14-19

[0157] Compounds 14 to 19 shown in Table 2 were prepared according to the preparation method in Example 13 above.

[0158] Table 2. Raw materials and product compounds

[0159]

[0160]

[0161] Device Examples

[0162] Example 20

[0163] refer to Figure 1 This embodiment provides a single-layer organic electroluminescent device, the fabrication method of which includes the following steps:

[0164] (1) A transparent ITO film with a thickness of 150 nm is formed on a glass substrate 10 by magnetron sputtering process, which serves as the anode 11.

[0165] (2) A mixture of compound 1 and compound M1 of this application with a mass ratio of 3:97 is deposited on the surface of anode 11 by vacuum evaporation to form a hole injection layer 12 with a thickness of 100 angstroms.

[0166] (3) A compound M1 is deposited on the surface of the hole injection layer 12 to form a first hole transport layer 13 with a thickness of 1000 angstroms.

[0167] (4) A compound M2 is vapor-deposited on the surface of the first hole transport layer 13 to form a second hole transport layer 14 with a thickness of 400 angstroms.

[0168] (5) Compounds M3, M4 and M5 are co-deposited on the surface of the second hole transport layer 14 in a mass ratio of 45:45:10 to form a light-emitting layer 15 with a thickness of 300 angstroms.

[0169] (6) A hole blocking layer 16 with a thickness of 50 angstroms is formed by vapor deposition of compound M6 on the surface of the light-emitting layer 15.

[0170] (7) A mixture of compounds M7 and LiQ with a mass ratio of 98:2 is vapor-deposited on the surface of the hole blocking layer 16 to form an electron transport layer 17 with a thickness of 300 angstroms.

[0171] (8) Magnesium (Mg) and silver (Ag) are mixed and deposited on electron transport layer 17 at a vapor deposition rate of 1:10 to form cathode 18 with a thickness of 1000 angstroms, thus completing the fabrication of organic electroluminescent device.

[0172] Examples 21-38

[0173] Except that when forming the hole injection layer 12, compounds 2 to 19 of this application were used to replace compound 1, the organic electroluminescent device was prepared using the same method as in Example 20.

[0174] Comparative Example 1

[0175] Except that compound M8 was used instead of compound 1 when forming hole injection layer 12, the organic electroluminescent device was prepared using the same method as in Example 20.

[0176] The structural formulas of the compounds involved in the above preparation methods are shown in Table 3 below:

[0177] Table 3 Structural formulas of related compounds

[0178]

[0179] Device performance testing

[0180] The operating voltage and current efficiency of the device were measured using a computer-controlled Keithley 2400 test system (test current 10mA / cm). 2 Using a Fostar lifetime measurement system equipped with a power supply and photodiode as detection units, the LT95 lifetime of the device was tested under dark conditions (test temperature 25°C, test current 50mA / cm). 2 LT95 lifetime refers to the time required for the brightness to decrease from its initial brightness to 95%. Each set of examples and comparative examples was produced and tested in the same batch. With the operating voltage, current efficiency, and LT95 lifetime of the device in Comparative Example 1 set at 100%, the operating voltage, current efficiency, and LT95 lifetime are shown in Table 4.

[0181] Table 4 Device Performance Test Results

[0182] Devices Hole injection layer material Operating voltage Current efficiency LT95 lifespan Comparative Example 1 Compound M8 100％ 100％ 100％ Example 20 Compound 1 95％ 106％ 116％ Example 21 Compound 2 97％ 106％ 112％ Example 22 Compound 3 93％ 110％ 116％ Example 23 Compound 4 96％ 112％ 128％ Example 24 Compound 5 97％ 108％ 113％ Example 25 Compound 6 95％ 108％ 115％ Example 26 Compound 7 98％ 106％ 113％ Example 27 Compound 8 97％ 105％ 118％ Example 28 Compound 9 98％ 108％ 123％ Example 29 Compound 10 96％ 109％ 118％ Example 30 Compound 11 95％ 115％ 113％ Example 31 Compound 12 94％ 106％ 110％ Example 32 Compound 13 95％ 118％ 128％ Example 33 Compound 14 99％ 105％ 110％ Example 34 Compound 15 98％ 105％ 115％ Example 35 Compound 16 97％ 106％ 111％ Example 36 Compound 17 98％ 105％ 114％ Example 37 Compound 18 96％ 107％ 111％ Example 38 Compound 19 98％ 105％ 112％

[0183] Example 39

[0184] refer to Figure 2 This embodiment provides a stacked organic electroluminescent device, the fabrication method of which includes the following steps:

[0185] (1) A transparent ITO film with a thickness of 150 nm is formed on a glass substrate 100 by magnetron sputtering process, which serves as the anode 110.

[0186] (2) A mixture of compound M1 and compound M8 with a mass ratio of 97:3 is deposited on the surface of anode 110 by vacuum evaporation to form a first hole injection layer 121 with a thickness of 100 angstroms.

[0187] (3) A compound M1 is vapor-deposited on the surface of the first hole injection layer 121 to form a first hole transport layer 131 with a thickness of 200 angstroms.

[0188] (4) A compound M2 is deposited on the surface of the first hole transport layer 131 to form a first electron blocking layer 141 with a thickness of 50 angstroms.

[0189] (5) On the surface of the first electron blocking layer 141, compounds M3, M4 and M5 are co-deposited in a mass ratio of 45:45:10 to form a first light-emitting layer 151 with a thickness of 300 angstroms.

[0190] (6) A first hole blocking layer 161 with a thickness of 50 angstroms is formed by vapor deposition of compound M6 on the surface of the first light-emitting layer 151.

[0191] (7) A mixture of compounds M7 and LiQ with a mass ratio of 1:1 is vapor-deposited on the surface of the first hole blocking layer 161 to form a first electron transport layer 171 with a thickness of 100 angstroms.

[0192] (8) A 200 angstrom n-type charge generation layer 181 is formed by vapor deposition of a mixture of compound M9 and metal Yb in a mass ratio of 98:2 on the first electron transport layer 171.

[0193] (9) A mixture of compound 1 and compound M1 of Example 1 of this application with a mass ratio of 3:97 is deposited on the surface of the n-type charge generation layer 181 to form a p-type charge generation layer 182 with a thickness of 100 angstroms.

[0194] (10) A second hole transport layer 132 of 4000 angstroms is formed by vapor deposition of compound M1 on the p-type charge generation layer 182.

[0195] (11) A second electron blocking layer 142 of 300 angstroms is formed by vapor deposition of compound M2 on the surface of the second hole transport layer 132.

[0196] (12) Compounds M3, M4 and M5 in a mass ratio of 45:45:10 are co-deposited on the surface of the second electron blocking layer 142 to form a second light-emitting layer 152 of 300 angstroms.

[0197] (13) A second hole blocking layer 162 with a thickness of 50 angstroms is formed by vapor deposition of compound M6 on the second light-emitting layer 152.

[0198] (14) A mixture of compound M7 and LiQ with a mass ratio of 1:1 of 300 angstroms is deposited on the second hole blocking layer 162, and then 10 angstroms of metal Yb is deposited to form the second electron transport layer 172.

[0199] (15) Magnesium (Mg) and silver (Ag) are mixed and deposited on the second electron transport layer 172 at a vapor deposition rate of 1:10 to form a cathode 180 with a thickness of 1000 angstroms, thus completing the fabrication of the organic electroluminescent device.

[0200] Examples 40-57

[0201] Except that when forming the p-type charge generation layer 182, compound 1 was replaced with compounds 2 to 19 of this application, the organic electroluminescent device was prepared using the same method as in Example 39.

[0202] Comparative Example 2

[0203] Except that compound M8 was used instead of compound 1 when forming the p-type charge generation layer 182, the organic electroluminescent device was prepared using the same method as in Example 39.

[0204] The structural formulas of the compounds involved in the above preparation methods are shown in Table 3.

[0205] The operating voltage, current efficiency, and LT95 lifetime of the devices prepared in Examples 39-57 and Comparative Example 2 were tested using the aforementioned device testing methods. Taking the operating voltage, current efficiency, and LT95 lifetime of the device in Comparative Example 2 as 100%, the operating voltage, current efficiency, and LT95 lifetime are shown in Table 5.

[0206] Table 5 Device Performance Test Results

[0207] Devices Charge generation layer material Operating voltage Current efficiency LT95 lifespan Comparative Example 2 Compound M8 100％ 100％ 100％ Example 39 Compound 1 96％ 107％ 105％ Example 40 Compound 2 96％ 105％ 102％ Example 41 Compound 3 94％ 108％ 112％ Example 42 Compound 4 96％ 112％ 115％ Example 43 Compound 5 94％ 106％ 105％ Example 44 Compound 6 95％ 112％ 109％ Example 45 Compound 7 97％ 106％ 104％ Example 46 Compound 8 98％ 110％ 115％ Example 47 Compound 9 96％ 109％ 116％ Example 48 Compound 10 95％ 108％ 118％ Example 49 Compound 11 97％ 105％ 105％ Example 50 Compound 12 99％ 102％ 101％ Example 51 Compound 13 94％ 106％ 110％ Example 52 Compound 14 98％ 105％ 104％ Example 53 Compound 15 99％ 105％ 110％ Example 54 Compound 16 97％ 102％ 103％ Example 55 Compound 17 98％ 102％ 103％ Example 56 Compound 18 96％ 110％ 104％ Example 57 Compound 19 97％ 106％ 107％

[0208] As shown in Table 4, compared with compound M8 of Comparative Example 1, when the organic compound of this application is used as the hole injection layer material, the operating voltage of the device is reduced by at least 2%, the current efficiency is increased by at least 5%, and the LT95 lifetime is increased by at least 10%, with an improvement rate as high as 28%. As shown in Table 5, compared with compound M8 of Comparative Example 2, when the organic compound of this application is used as the charge generation layer material, the operating voltage of the device decreases, and the efficiency and lifetime of the device are also improved.

[0209] Therefore, the organic compound of this application has good charge transport capability, which can ensure that the device has a high hole mobility, thereby reducing the operating voltage of the device and improving the device efficiency. At the same time, the organic compound molecule has high stability, which can further improve the device efficiency and service life.

[0210] The above description of the embodiments is intended to enable those skilled in the art to understand and apply this application. It will be apparent to those skilled in the art that various modifications can be easily made to these embodiments, and the general principles described herein can be applied to other embodiments without creative effort. Therefore, this application is not limited to the embodiments described herein, and any improvements and modifications made by those skilled in the art based on the disclosure of this application without departing from the scope and spirit of this application are within the scope of this application.

Claims

1. An organic compound, characterized in that, The general formula of the organic compound is shown in Formula I-1 or Formula I-2: in: A is absent, or when A is present, A is selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C5-C18 heteroaryl groups; n is selected from 1, 2, or 3; Rp1, Rq1, Rp2, and Rq2, each time appearing, are selected from the same or different groups or combinations thereof: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, thiocyano, isocyanate, pentafluorosulfonyl, sulfinyl, sulfonyl, phosphoxy, hydroxyl, mercapto, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C3-C20 heterocyclic, substituted or unsubstituted C7-C3 0% aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aroxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 silyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C3-C20 alkylgermanium, substituted or unsubstituted C6-C20 arylgermanium; and Rp2 and Rq2 may form rings.

2. The organic compound according to claim 1, characterized in that, In Formula I-1, at least one of Rp1 and Rq1 is a group having an electron-withdrawing group; in Formula I-2, at least one of Rp2 and Rq2 is a group having an electron-withdrawing group.

3. The organic compound according to claim 1 or 2, characterized in that, In formula I-1, A is none and n is 1; the organic compound is represented by the following formula II: R1 is defined the same as Rp1, and R2 is defined the same as Rq1.

4. The organic compound according to claim 3, characterized in that, The structural formula of the organic compound is selected from the following group: R2 is selected from 5. The organic compound according to claim 4, characterized in that, The organic compounds are selected from the following group:

6. The organic compound according to claim 1 or 2, characterized in that, In Formula I-2, A is selected from phenyl, phenanthrene, phenanthrene and cyclosulfonyl fused groups; n is 2.

7. The organic compound according to claim 6, characterized in that, The organic compound is represented by any of the following structural formulas: Among them, R3~R 35 Each time it appears, it is selected from the same or different groups or combinations thereof: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, thiocyanate, isocyanate, pentafluorosulfonyl, sulfinyl, sulfonyl, phosphoxy, hydroxyl, mercapto, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C3-C20 heterocyclic, substituted or unsubstituted C7-C30 aralkyl. Substituted or unsubstituted C1–C20 alkoxy groups, substituted or unsubstituted C6–C30 aryloxy groups, substituted or unsubstituted C2–C20 alkenyl groups, substituted or unsubstituted C2–C20 alkynyl groups, substituted or unsubstituted C6–C30 aryl groups, substituted or unsubstituted C3–C30 heteroaryl groups, substituted or unsubstituted C3–C20 silyl groups, substituted or unsubstituted C6–C20 arylsilyl groups, substituted or unsubstituted C3–C20 alkylgermanium groups, and substituted or unsubstituted C6–C20 arylgermanium groups.

8. The organic compound according to claim 7, characterized in that, The structural formula of the organic compound is selected from the following group: Among them, R4 is selected from CN, R5 is selected from CN; Alternatively, the structural formula of the organic compound is selected from the following group: Among them, R 10 Selected from R7, R9, R 12 R 13 Independently selected from H and CN; Alternatively, the structural formula of the organic compound is selected from the following group: Among them, R 19 Selected from R 20 and R 21 The organic compound is independently selected from H, F, and CN; or, the structural formula of the organic compound is selected from the group consisting of: Among them, R 33 Selected from F, CN, NO2, H; R 34 Selected from CN.

9. The organic compound according to claim 8, characterized in that, The organic compounds are selected from the following group:

10. An organic layer, characterized in that, It includes the organic compound according to any one of claims 1 to 9.

11. Use of the organic compound according to any one of claims 1 to 9 or the organic layer according to claim 10 in an organic electroluminescent device.

12. An organic electroluminescent device, characterized in that, It includes a first electrode, a second electrode, and an organic layer as described in claim 10 located between the first electrode and the second electrode.

13. The organic electroluminescent device according to claim 12, wherein the organic layer comprises a hole injection layer and / or a charge generation layer, wherein the hole injection layer and / or charge generation layer comprises an organic compound according to any one of claims 1 to 9.

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