Organic compounds and their uses

Abstract

The present invention provides an organic compound and its use, which has improved molecular packing density through molecular structure design, has excellent hole transport properties, and can also adjust and improve the HOMO energy level of the compound, which is more compatible with anode materials, improves the hole injection and transport ability of the compound, contributes to achieving low voltage, and also greatly improves the stability of carrier transport under electric field environment. When used as an organic electroluminescence device material, the organic compound has good film-forming properties and is suitable for use in organic electroluminescence devices, especially as a hole transport layer material and / or an electron blocking layer material, which can effectively improve the luminous efficiency and stability of the device, extend the life, reduce the voltage, and achieve a better luminous effect.

Description

[Technical field]

[0001] The present invention is in the technical field of organic electroluminescent materials, specifically organic compounds and their uses. [Background technology]

[0002] In recent years, optoelectronic devices based on organic materials have become increasingly popular. Compared with inorganic materials, organic materials are suitable for manufacturing on flexible substrates due to their inherent flexibility, making it possible to design and produce a variety of optoelectronic products according to needs. Currently known organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic solar cells, organic sensors, etc. Among them, OLEDs have the advantages of self-luminescence, high contrast, wide color gamut, flexibility, low power consumption, etc., and have developed particularly rapidly and are widely used in many fields such as flexible displays, flat displays and solid-state lighting.

[0003] An OLED device includes a cathode, an anode, and an organic thin film structure between the two electrodes, and the core of the device is a thin film structure containing various organic functional materials. Common organic functional materials include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, emissive host materials, emissive guests (dyes), etc. When electricity is applied, electrons and holes are injected and transported to the emissive region, respectively, where they recombine to generate excitons and emit light. In an OLED device, the organic functional materials directly affect the emissive properties of the device.

[0004] Hole transport materials, which are common layer materials in OLED devices, affect important indicators such as device voltage, efficiency, and lifespan by adjusting the hole injection and transport properties. Currently, the hole transport materials used in commercial mass production are mainly arylamine-based materials. Due to the different material combinations used in the devices, the currently used materials and device structures cannot fully solve the problems of efficiency, lifespan, cost, etc. of OLED products.

[0005] Therefore, there is an urgent need in this field to develop organic electroluminescent materials that can improve the luminous efficiency, reduce the driving voltage, and extend the service life of the devices. Summary of the Invention [Problem to be solved by the invention]

[0006] In view of the shortcomings of the prior art, the object of the present invention is to provide an organic compound and its use, which has good optoelectronic properties and is suitable for use in organic electroluminescent devices, in particular as a hole transport material and / or electron blocking material, and can effectively reduce the driving voltage, improve the efficiency and extend the life of the device. [Means for solving the problem]

[0007] In order to achieve the object of the present invention, the present invention adopts the following technical solutions. A first object of the present invention is to provide an organic compound having the structure shown in Formula I: JPEG2025501127000002.jpg57170

[0008] In formula I, R1, R2, R3, and R4 are each independently any one selected from substituted or unsubstituted C1 to C30 linear or branched alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C3 to C30 heteroaryl, wherein R1 and R2 are not linked together or are linked together by a chemical bond to form a ring, and R3 and R4 are not linked together or are linked together by a chemical bond to form a ring.

[0009] In formula I, R5 and R6 are each independently any one selected from substituted or unsubstituted C1 to C30 linear or branched alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C3 to C30 heteroaryl.

[0010] In formula I, L1 and L2 are each independently any one selected from a single bond, a substituted or unsubstituted C6 to C30 alkylene, and a substituted or unsubstituted C3 to C30 heteroarylene. When L1 and L2 are single bonds, this indicates that the fluorene structure is directly linked to the N atom via a single bond.

[0011] The substituents for substitution in R1, R2, R3, R4, R5, R6, L1, and L2 are each independently at least one selected from C1 to C20 linear or branched alkyl, C3 to C20 cycloalkyl, C6 to C30 arylamino, C3 to C30 heteroarylamino, C6 to C30 aryl, and C3 to C30 heteroaryl.

[0012] In formula I, Cy is any one selected from substituted or unsubstituted C6 to C30 aryl and substituted or unsubstituted C3 to C30 heteroaryl.

[0013] The substituents for substitution in Cy are each independently at least one selected from C3 to C20 cycloalkyl, C6 to C30 arylamino, C3 to C30 heteroarylamino, C6 to C30 aryl, and C3 to C30 heteroaryl.

[0014] In formula I, n1 and n2 are each independently selected from integers of 0 to 4, and may be, for example, 0, 1, 2, 3, or 4.

[0015] When n1≧2, multiple (at least two) R5s are the same or different, and adjacent R5s are not linked; when n2≧2, multiple (at least two) R6s are the same or different, and adjacent R6s are not linked.

[0016] The organic compound according to the present invention is a triarylamine-based compound having a structure shown in formula I and containing at least two fluorene structures. The triarylamine group in the core can effectively adjust the three-dimensional structure of the molecule and improve the density of molecular packing. In addition, the triarylamine structure and the fluorene structure cooperate to give the organic compound excellent hole transport and hole injection properties, effectively adjust and improve the HOMO energy level of the compound, increase the compatibility with the anode material, and improve the hole injection and hole injection transport capabilities of the material, which contributes to the achievement of low voltage and greatly improves the stability of carrier transport in an electric field environment. In addition, the special tetrahedral structure of the organic compound allows a good amorphous film to be obtained, so that the organic compound shows good film formation properties when used as an organic electroluminescence device material. When the organic compound is used in an organic electroluminescence device, especially when used as a hole transport layer material and / or an electron blocking layer material, it can effectively improve the efficiency and stability of the device, extend the life, lower the voltage, and obtain better light emission results.

[0017] In the present invention, the "adjacent R5 is not connected" means that R5 is connected to the adjacent aryl by a single bond and does not form a condensed ring with the adjacent aryl. The "adjacent R6 is not connected" means that R6 is connected to the adjacent aryl by a single bond and does not form a condensed ring with the adjacent aryl.

[0018] The reason is that the two fluorene ring structures in the present invention can achieve a suitable HOMO energy level very well, so when the fluorene ring is further condensed with another aromatic ring, the HOMO energy level of the whole molecule changes greatly.When the benzene ring on the fluorene ring is further connected to another non-aromatic ring structure, the theoretical HOMO calculation value is acceptable, but when actually used, it is found that the life characteristics are very poor.This is because the non-aromatic ring connected to the fluorene ring affects the extension direction of the two fluorene rings of the triaryl due to steric hindrance, changing the stacking behavior during film formation, and cannot obtain sufficient effect, which is undesirable.

[0019] In addition, in the present invention, for the convenience of explanation, the possible role of each group / characteristic is described separately, but this does not mean that these groups / characteristics function alone.In fact, the essential reason for obtaining excellent properties lies in the optimized combination of the whole molecule, which is the result of synergistic action between individual groups, not the effect of a single group.

[0020] In the present invention, for the convenience of explanation, the "substituted or unsubstituted" group may be substituted with one substituent, or may be substituted with multiple (at least two) substituents, and when there are multiple (at least two) substituents, they may be the same or different. Hereinafter, when the same expression is described, they all have the same meaning, and the selection range of the substituent is as described above, and will not be described in detail here.

[0021] In the present invention, unless otherwise specified, the expression of a chemical element includes the concept of an isotope having the same chemical properties. For example, hydrogen (H) has the following isotopes: 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T) and carbon (C) 12 C. 13 Includes C.

[0022] In the present invention, the heteroatom of a heteroaryl is an atom or group of atoms selected from N, O, S, P, B, Si or Se, with N, O and S being preferred.

[0023] In the present invention, an expression in which a ring structure is crossed with "-" or "----" means that the linking site is at any position on the ring structure where a bond can be formed.

[0024] In the present invention, the expressions Ca to Cb indicate that the number of carbon atoms in the group is a to b, but unless otherwise specified, this number of carbon atoms generally does not include the number of carbon atoms in the substituents.

[0025] In this specification, the term "independently" means that when there are multiple objects, they may be the same or different.

[0026] In the present invention, the C1-C30 linear or branched alkyl may be any linear or branched alkyl such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, or C28, but is preferably a C1-C20 linear or branched alkyl, preferably a C1-C16 linear or branched alkyl, and more preferably a C1-C10 linear or branched alkyl, and examples thereof include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl, or n-decyl.

[0027] In the present invention, the C3 to C20 cycloalkyl may be any cycloalkyl such as C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18, including, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0028] In the present invention, the C6-C30 aryl may be any of C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28 aryls, but preferably, the C6-C20 aryl includes a monocyclic aryl or a fused ring aryl. The monocyclic aryl refers to a group containing at least one phenyl, and when containing at least two phenyls, the phenyls are connected to each other by a single bond, and examples thereof include, but are not limited to, phenyl, biphenyl, and terphenyl. The fused ring aryl refers to a group containing at least two aromatic rings, which are fused to each other by sharing two adjacent carbon atoms, and examples thereof include, but are not limited to, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and its derivatives (9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, perylenyl, chrysenyl, naphthacenyl, etc. The above-mentioned groups include all possible linking forms thereof.

[0029] In the present invention, the C3-C30 heteroaryl may be any of C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28 heteroaryls, but is preferably C4-C20 heteroaryl, more preferably C4-C12 heteroaryl, including monocyclic heteroaryl or fused ring heteroaryl. The monocyclic heteroaryl refers to a ring containing at least one heteroaryl in the molecule, and when the ring contains one heteroaryl and another group (e.g., aryl, heteroaryl, alkyl, etc.), the heteroaryl and the other group are linked by a single bond, and examples thereof include, but are not limited to, furyl, thienyl, pyrrolyl, pyridyl, etc. The fused ring heteroaryl refers to a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, in which two adjacent atoms shared by both of the rings are fused to each other. Examples include, but are not limited to, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, azacarbazolyl, etc.), acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, hydrogenated acridinyl, etc., and the above-mentioned groups include all possible linking forms.

[0030] Specific examples of the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28) arylene of the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned aryl examples. Specific examples of the C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28) heteroarylene of the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned heteroaryl examples.

[0031] The C6 to C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) arylamino of the present invention includes, but is not limited to, phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino, etc.

[0032] The C3 to C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroarylamino of the present invention includes, but is not limited to, pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0033] Preferably, R1, R2, R3, and R4 are each independently any one selected from substituted or unsubstituted C1 to C30 linear or branched alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, and substituted or unsubstituted C6 to C30 aryl.

[0034] As a preferred technical solution of the present invention, R1 and R2 are not linked or are linked by a chemical bond to form a ring A1; R3 and R4 are not linked or are linked by a chemical bond to form a ring A2; The ring A1 and ring A2 are each independently any one selected from a C3 to C20 alicyclic ring or a C6 to C30 aromatic ring.

[0035] As a preferred technical solution of the present invention, the C3-C20 alicyclic ring may be an alicyclic ring such as C3, C4, C5, C6, C9, C10, C12, C14, C16, or C18, more preferably a C3-C12 alicyclic ring, more preferably a saturated alicyclic ring, such as an adamantane ring.

[0036] In a more preferred technical solution of the present invention, the C6 to C30 aromatic ring may be an aromatic ring such as C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, and more preferably is a C10 to C20 aromatic ring, examples of which include, but are not limited to, a fluorene ring, a benzofluorene ring, and a dibenzofluorene ring.

[0037] More preferably, R1, R2, R3, and R4 are each independently any one selected from substituted or unsubstituted C1 to C6 linear or branched alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, and substituted or unsubstituted C6 to C20 aryl.

[0038] As another preferred technical solution of the present invention, R1 and R2 are not linked or are linked by a chemical bond to form ring A1, and R3 and R4 are not linked or are linked by a chemical bond to form ring A2; The ring A1 and the ring A2 are each independently any one selected from a C3 to C12 alicyclic ring or a C10 to C20 aromatic ring, Preferably, the ring A1 and the ring A2 are each independently any one selected from an adamantane ring, a fluorene ring, or a benzofluorene ring.

[0039] Preferably, R5 and R6 are each independently any one selected from substituted or unsubstituted C1 to C6 linear or branched alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, and substituted or unsubstituted C6 to C20 aryl.

[0040] Preferably, R5 and R6 are each independently selected from phenyl, biphenyl, or naphthyl.

[0041] Preferably, n1 and n2 are each independently 0 or 1.

[0042] Preferably, L1 and L2 are each independently any one selected from a single bond, a substituted or unsubstituted C6 to C20 alkylene, and a substituted or unsubstituted C3 to C20 heteroarylene.

[0043] Preferably, L1 and L2 are both JPEG2025501127000003.jpg31170, where the dashed lines represent the sites of attachment of the groups.

[0044] Preferably, L1 and L2 each independently represent one selected from the following single bond, or a substituted or unsubstituted group: JPEG2025501127000004.jpg95170JPEG2025501127000005.jpg78170Here, the dashed lines represent the linkage sites of the groups.

[0045] Preferably, the Cy is any one selected from substituted or unsubstituted C6 to C20 aryl.

[0046] In the present invention, said Cy is not dimethylfluorenyl.

[0047] In the case of dimethylfluorenyl, the technical effect is insufficient, and the reason for this is believed to be that fluorenyl, as a strong electron donating group, affects the energy level distribution of the material.

[0048] Preferably, the Cy is any one selected from the following substituted or unsubstituted groups: JPEG2025501127000006.jpg81170 Here, the dashed lines represent the linking sites of the groups.

[0049] Preferably, when a substituent is present in the "substituted or unsubstituted" described above in the present invention, the substituent in R1, R2, R3, R4, R5, R6, L1, and L2 is each independently selected from the group consisting of C1 to C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10) straight-chain or branched alkyl, C3 to C10 (e.g., C3, C4, C5, C6, C7, C8, C9, C10) cycloalkyl, C6 to C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28) arylamino, C3 At least one selected from C3 to C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroarylamino, C6 to C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) aryl, or C3 to C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroaryl. The substituents in Cy are each independently selected from the group consisting of C3 to C10 (e.g., C3, C4, C5, C6, C7, C8, C9, and C10) cycloalkyl, C6 to C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, and C28) arylamino, C3 to C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, and C24, C26, C28, etc.) heteroarylamino; C6 to C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) aryl; and C3 to C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl.

[0050] Preferably, the organic compound has any one of the structures represented by the following C1 to C318. JPEG2025501127000007.jpg112170JPEG2025501127000008.jpg234170JPEG2025501127000009.jpg225170JPEG2025501127000010.jpg245170 JPEG2025501127000011.jpg246170JPEG2025501127000012.jpg242170JPEG2025501127000013.jpg243170JPEG2025501127000014.jpg237170 JPEG2025501127000015.jpg255166JPEG2025501127000016.jpg192170JPEG2025501127000017.jpg232170JPEG2025501127000018.jpg237170 JPEG2025501127000019.jpg237170JPEG2025501127000020.jpg226170JPEG2025501127000021.jpg211170JPEG2025501127000022.jpg225170

[0051] A second object of the present invention is to provide the use of an organic compound as described for the first object, said organic compound being used in an organic electroluminescent device.

[0052] Preferably, the organic compounds are used as electron blocking layer materials and / or hole transport layer materials in organic electroluminescent devices.

[0053] Preferably, the organic compound is used as a hole injection layer material in an organic electroluminescent device.

[0054] In addition to organic electroluminescent devices, the organic compounds of the present invention can also be used in other types of organic electronic devices, including lighting devices, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet scanners or electronic paper.

[0055] A third object of the present invention is to provide an arylamine-based organic compound, in which the orbital overlap integral between HOMO and LUMO is greater than 0.6, and may be, for example, 0.61, 0.62, 0.63, 0.64, 0.65, 0.66, 0.67, 0.68, 0.69, 0.70, 0.71, 0.72, or 0.73, in the ground state structure optimized at the B3LYP / 6-31G(d) calculation level.

[0056] JPEG2025501127000023.jpg51170

[0057] Among all the electron-filled orbitals in a compound, the orbital in which the electron has the highest energy is called the highest occupied molecular orbital (HOMO). Meanwhile, among all the electron-unfilled orbitals, the orbital in which the electron has the lowest energy is called the lowest unoccupied molecular orbital (LUMO). The transport of charge in a material is a process in which electrons are continuously removed from the HOMO and added to the LUMO, which involves a continuous change in the molecular configuration of the compound between the HOMO and LUMO. When the HOMO and LUMO orbitals of an organic material overlap in space, the change in the geometric configuration of the compound during the charge transfer process is reduced, which contributes to maintaining stability and extending the lifetime of the device. In quantum chemistry, the degree of spatial overlap between the HOMO and LUMO orbitals can be expressed as the orbital overlap integral, which ranges from 0 to 1 and is defined as follows: ∫|φH(r)||φL(r)|dr Eq.

[0058] In formula a, |φH(r)| is the mode of the HOMO orbital wave function, |φL(r)| is the mode of the LUMO orbital wave function, and r represents the position vector. The larger the value, the higher the degree of spatial overlap between the HOMO orbital and the LUMO orbital. The structure of the arylamine-based organic compound is optimized based on B3LYP / 6-31G(d) using Gaussian 09 software, and the orbital wave functions of the HOMO and LUMO are obtained, thereby calculating the orbital overlap integral of the HOMO and LUMO. Through many studies, the present invention has found that when the overlap integral between the HOMO orbital and the LUMO orbital of the ground state structure of the arylamine-based compound is greater than 0.6, it can show better stability during carrier transport.

[0059] Preferably, the arylamine-based organic compound comprises an organic compound as described in the first object.

[0060] A fourth object of the present invention is to provide a use of the arylamine-based organic compound according to the third object, wherein the arylamine-based organic compound is used in an organic electroluminescent device.

[0061] Preferably, the arylamine based organic compounds are used as electron blocking layer materials and / or hole transport layer materials in organic electroluminescent devices.

[0062] Preferably, the arylamine based organic compounds are used as hole injection layer materials in organic electroluminescent devices.

[0063] A fifth object of the present invention is to provide an organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, the organic layer comprising at least one organic compound according to the first object and / or an arylamine-based organic compound according to the third object.

[0064] Preferably, the organic layer contains at least one organic compound having a structure represented by C1 to C318 described in the first object.

[0065] Preferably, the organic layer comprises a hole transport layer, the hole transport layer comprising at least one organic compound as described in the first object and / or at least one arylamine-based organic compound as described in the third object.

[0066] Preferably, the organic layer includes an electron blocking layer, and the electron blocking layer includes at least one organic compound described in the first object and / or an arylamine-based organic compound described in the third object.

[0067] The organic compound and / or arylamine-based organic compound according to the present invention, when used as an electron blocking layer material and / or a hole transport layer material, can significantly improve the luminous efficiency of an organic electroluminescence device, lower the driving voltage, reduce energy consumption, and optimize the stability of the device.

[0068] Preferably, the organic layer comprises a hole injection layer, the hole injection layer comprising at least one organic compound as described in the first object.

[0069] In a specific embodiment, the organic electroluminescent device includes a substrate, and a first electrode, an organic layer, and a second electrode sequentially stacked on the substrate, the organic layer including any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, or an electron injection layer, wherein the organic layer (e.g., any one or at least two of a hole injection layer, a hole transport layer, and an electron blocking layer) includes at least one organic compound having a structure represented by Formula I, more preferably an organic compound having a structure represented by any one of C1 to C318.

[0070] In certain embodiments, a substrate may be used under the first electrode or over the second electrode. The substrates are all glass or polymer materials with good mechanical strength, thermal stability, waterproofness, and transparency. In addition, thin film transistors (TFTs) can be provided on the substrate for display.

[0071] The first electrode can be formed by sputtering or depositing the material for the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof can be used. When the first electrode is used as a cathode, a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof can be used.

[0072] The organic layer can be formed on the electrode by methods such as vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer can be an organic small molecule, an organic macromolecule or polymer, and a combination thereof.

[0073] The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one type of compound and a single-layer hole transport layer containing multiple types of compounds. The hole transport region may be a multi-layer structure including at least one layer selected from a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL). Among these, the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light emitting layer, and the hole transport layer (HTL) and / or the electron blocking layer (EBL) include at least one organic compound having a structure represented by formula I, more preferably an organic compound having a structure represented by C1 to C318.

[0074] Preferably, the hole injection layer (HIL) contains at least one organic compound having a structure of formula I, more preferably an organic compound having a structure represented by C1 to C318.

[0075] The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers, or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), arylamine derivatives, etc. The arylamine derivatives include the compounds shown below as HT-1 to HT-51, or any combination thereof. JPEG2025501127000024.jpg87170JPEG2025501127000025.jpg255168JPEG2025501127000026.jpg231170

[0076] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of multiple compounds. For example, the hole injection layer may employ one or more compounds among the above HT-1 to HT-34, the organic compound described in the first objective (preferably, an organic compound having a structure represented by C1 to C318), or one or more compounds among the following HI-1 to HI-3, or may be one in which one or more compounds among the HT-1 to HT-34 and / or the organic compound described in the first objective (preferably, an organic compound having a structure represented by C1 to C318) are doped with one or more compounds among the following HI-1 to HI-3. JPEG2025501127000027.jpg55170

[0077] The light-emitting layer may include light-emitting dyes (i.e., dopants) capable of emitting different wavelength spectrums, and may also include a host material. The light-emitting layer may be a monochromatic light-emitting layer that emits a single color, such as red, green, or blue. A plurality of monochromatic light-emitting layers of different colors may be arranged on a plane according to a pixel pattern, or may be stacked to form a colored light-emitting layer. When stacking light-emitting layers of different colors, the light-emitting layers may be spaced apart from each other or connected to each other. The light-emitting layer may also be a single color light-emitting layer that can simultaneously emit different colors, such as red, green, and blue.

[0078] Depending on the technology, the light-emitting layer materials can be a variety of materials, such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescent luminescent materials, etc. In an OLED device, a single light-emitting technology can be used or several different light-emitting technologies can be used in combination. These different light-emitting materials, classified by technology, can emit the same color light or different colors of light.

[0079] In one embodiment of the present invention, the light-emitting layer employs fluorescent electroluminescence technology, and the fluorescent host material of the light-emitting layer may be one or a combination of materials selected from the following BFH-1 to BFH-17, but is not limited thereto. JPEG2025501127000028.jpg83170JPEG2025501127000029.jpg36170

[0080] In one embodiment of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology, and the fluorescent dopant of the light-emitting layer may be one or a combination of the following BFD-1 to BFD-24, but is not limited thereto. JPEG2025501127000030.jpg40170JPEG2025501127000031.jpg158170JPEG2025501127000032.jpg97170

[0081] In one embodiment of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology, and the host material of the light-emitting layer may be one or a combination of materials selected from PH-1 to PH-85, but is not limited thereto. JPEG2025501127000033.jpg118170JPEG2025501127000034.jpg248170JPEG2025501127000035.jpg255166JPEG2025501127000036.jpg115170

[0082] In one embodiment of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology, and the phosphorescent dopant of the light-emitting layer may be one or a combination of dopants selected from the following GPD-1 to GPD-47, but is not limited thereto. JPEG2025501127000037.jpg95170JPEG2025501127000038.jpg232170JPEG2025501127000039.jpg72170Here, D is deuterium.

[0083] In one embodiment of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology, and the phosphorescent dopant of the light-emitting layer may be one or a combination of the following RPD-1 to RPD-28, but is not limited thereto. JPEG2025501127000040.jpg149170JPEG2025501127000041.jpg77170

[0084] In one embodiment of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology, and the phosphorescent dopant of the light-emitting layer may be one or a combination of the following compounds: YPD-1 to YPD-11, but is not limited thereto. JPEG2025501127000042.jpg68170

[0085] The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may be a multi-layer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0086] In one embodiment of the present invention, the electron transport layer material may be one or a combination of materials selected from the following ET-1 to ET-73, but is not limited thereto. JPEG2025501127000043.jpg39170JPEG2025501127000044.jpg232170JPEG2025501127000045.jpg226170JPEG2025501127000046.jpg221170

[0087] The device may further include an electron injection layer located between the electron transport layer and the cathode, and the electron injection layer material may include, but is not limited to, one or more combinations selected from LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Yb, Li, or Ca. Effect of the Invention

[0088] Compared with the prior art, the present invention has the following beneficial effects:

[0089] The organic compound according to the present invention has a structure shown in formula I, and the triarylamine group in the core can effectively adjust the three-dimensional structure of the molecule and improve the density of molecular packing.In addition, the triarylamine structure and the fluorene structure cooperate to give the organic compound excellent hole transport properties, adjust and improve the HOMO energy level of the compound, and better match the energy level of the anode material, thereby improving the hole injection property and hole transport property of the compound, contributing to the achievement of low voltage, and greatly improving the stability of carrier transport in an electric field environment.In addition, the special tetrahedral structure of the organic compound can obtain a good amorphous film, so that it shows good film formation properties when used as a material for organic electroluminescence devices.

[0090] The arylamine organic compound according to the present invention has a large orbital overlap integral between the HOMO and LUMO, and has high stability of carrier transport in an electric field environment.

[0091] The organic compounds and / or arylamine-based organic compounds are suitable for use in organic electroluminescence devices, particularly as hole transport layer materials and / or electron blocking layer materials, and can effectively improve the luminous efficiency and stability of the device, extend the device life, reduce the voltage, and achieve better luminous effect.

[0092] Furthermore, the process for producing organic compounds according to the present invention is easy to implement, has ready availability of raw materials and is amenable to scale-up. [Brief description of the drawings]

[0093] [Figure 1] FIG. 2 is a molecular orbital distribution diagram of the organic compound C1 according to the present invention. [Diagram 2] FIG. 2 is a molecular orbital distribution diagram of the organic compound C2 according to the present invention. [Diagram 3] FIG. 2 is a molecular orbital distribution diagram of the organic compound C5 according to the present invention. [Figure 4] FIG. 2 is a molecular orbital distribution diagram of the organic compound C7 according to the present invention. [Diagram 5] FIG. 2 is a molecular orbital distribution diagram of the organic compound C9 according to the present invention. [Figure 6] FIG. 2 is a molecular orbital distribution diagram of the organic compound C12 according to the present invention. [Figure 7] FIG. 2 is a molecular orbital distribution diagram of the organic compound C13 according to the present invention. [Figure 8] FIG. 1 is a molecular orbital distribution diagram of compound R1. [Figure 9] FIG. 2 is a molecular orbital distribution diagram of the comparative compound R2. [Figure 10] FIG. 2 is a molecular orbital distribution diagram of the comparative compound R3. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0094] The technical solution of the present invention will be further described below by means of specific embodiments. Those skilled in the art will understand that the above examples are merely for aiding in the understanding of the present invention, and are not to be construed as limiting the present invention.

[0095] General synthesis of the compounds of the present invention: In one particular embodiment, the organic compounds may be prepared according to the following representative synthetic scheme: JPEG2025501127000047.jpg99170

[0096] Here, R1, R2, R3, R4, R5, R6, L1, L2, Cy, n1, and n2 have the same limited range as that of Formula I. Pd2(dba)3 represents tris(dibenzylideneacetone)dipalladium(0), IPr.HCl represents 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride, NaOBu-t represents sodium tert-butoxide, and (t-Bu)3P represents tri-tert-butylphosphine; JPEG2025501127000048.jpg29170 may be produced by the following exemplary synthesis scheme: JPEG2025501127000049.jpg27170

[0097] It should be noted that the synthesis method and raw materials used in the present invention are not limited to the organic compounds. Those skilled in the art can also select other known methods or schemes to obtain the organic compounds provided by the present invention. The compounds for which the synthesis method is not described in the present invention are all commercially available raw materials or are self-made using these raw materials according to known methods.

[0098] Specifically, specific methods for producing the organic compounds described in the present invention will be described in detail below with reference to several synthesis examples, but the production methods of the present invention are not limited to these synthesis examples.

[0099] Mass spectrometry characteristic data (m / z) of the intermediates and organic compounds in the present invention are obtained by testing using a ZAB-HS mass spectrometer (Micromass, UK).

[0100] Synthesis example 1: Obtaining organic compound C1 JPEG2025501127000050.jpg37170JPEG2025501127000051.jpg67170

[0101] (1) Synthesis of intermediate C1-1 2,3-Dichloronitrobenzene (30g, 156.25mmol), phenylboronic acid (47.63g, 390.64mmol), tris(dibenzylideneacetone)dipalladium(0)Pd2(dba)3 (2.86g, 3.13mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl s-Phos (2.57g, 6.25mmol), potassium phosphate (66.33g, 312.51mmol) were added to a 1000mL one-neck flask equipped with a magnetic stirrer at room temperature, 500mL of dioxane and 50mL of water were added, stirring was started, nitrogen substitution was performed three times, the temperature was raised to 100°C, and the reaction was carried out overnight. As a result of monitoring by thin layer chromatography (TLC), the reaction of the raw materials was completed. The reaction mixture was cooled to room temperature and extracted with ethyl acetate. The upper supernatant was collected, spin-dried, and passed through a 100-200 mesh silica gel column with petroleum ether (PE):dichloromethane (DCM) = 10:1 to obtain 40.56 g of an oily liquid.

[0102] (2) Synthesis of intermediate C1-2 In a 2000 mL one-neck flask equipped with a magnetic stirrer, intermediate C1-1 (40.56 g, 147.33 mmol), ammonium formate (92.90 g, 1.47 mol), and Pd / C (20 g) were added at room temperature, 600 mL of ethanol (EtOH) was added, stirring was started, nitrogen replacement was performed three times, the temperature was raised to 80 ° C, and the reaction was performed for 2 h. As a result of monitoring by TLC, the reaction of the raw materials was completed. After filtration with diatomaceous earth, the solvent was removed by a rotary evaporator. PE:DCM = 10:1 was passed through a 100-200 mesh silica gel column to obtain 31.85 g of an oily liquid. Mass spectrometry m / z: 245.

[0103] (3) Synthesis of organic compound C1 Intermediate C1-2 (6.85 g, 27.92 mmol), 2-bromo-9,9-dimethylfluorene (17.54 g, 64.22 mmol), Pd2(dba)3 (1.28 g, 1.40 mmol), tri-tert-butylphosphine (t-Bu)3P (0.56 g, 2.79 mmol), sodium tert-butoxide NaOBu-t (8.05 g, 83.77 mmol) were added to 500 mL of toluene, stirred uniformly, and reacted overnight at 110 ° C under nitrogen protection. As a result of monitoring by TLC, the reaction of the raw material was completed. After cooling, it was passed through a silica gel short column, rinsed with toluene, and concentrated to obtain a brown oily product. 300 mL of ethanol was added, refluxed and stirred overnight, and filtered to obtain a white solid. It was washed by boiling with 200 mL of ethyl acetate for 4 h, and filtered to obtain a white solid. Recrystallization from toluene / ethanol gave 7.4 g of white solid product C1.

[0104] Organic compound C1: m / z theoretical: 629.85; measured: 630.83.

[0105] Synthesis example 2: Obtaining organic compound C2 JPEG2025501127000052.jpg58170

[0106] (1) Synthesis of intermediate C2-2 Intermediate C1-2 (15 g, 61.14 mmol), 2-bromo-9,9-dimethylfluorene (16.70 g, 61.14 mmol), Pd2(dba)3 (0.56 g, 0.61 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride IPr.HCl (0.52 g, 1.22 mmol), NaOBu-t (11.75 g, 122.29 mmol) were added to 500 mL of toluene, stirred uniformly, heated to 110 ° C under nitrogen protection, and reacted overnight. As a result of monitoring by TLC, the reaction of the raw materials was completed. After cooling, the solvent was removed by rotation using a high-speed silica gel column, and then 100 mL of ethanol was added, and a solid was precipitated. The solid was collected, separated through a column, and washed with PE:DCM=20:1 and boiled with ethanol to obtain 12.85 g of intermediate C2-2.

[0107] (2) Synthesis of organic compound C2 Intermediate C2-2 (12.85 g, 29.37 mmol), 2-bromo-9,9-diphenylfluorene (14 g, 35.24 mmol), Pd2(dba)3 (0.54 g, 0.59 mmol), (t-Bu)3P (0.24 g, 1.17 mmol), NaOBu-t (5.64 g, 58.73 mmol) were added to 500 mL of toluene, stirred uniformly, and reacted overnight at 110 ° C under nitrogen protection. As a result of monitoring by TLC, the reaction of the raw material was completed. After cooling, it was passed through a silica gel short column, rinsed with toluene, and concentrated to obtain a brown oily substance. It was washed by boiling with 200 mL of petroleum ether, filtered to obtain a white solid, and recrystallized with N,N-dimethylformamide (DMF) to obtain 8.8 g of white solid C2.

[0108] Organic compound C2: m / z theoretical: 753.99; observed: 754.33.

[0109] Synthesis Examples 3 to 14: Obtaining other compounds of the present invention by changing the raw materials JPEG2025501127000053.jpg48170JPEG2025501127000054.jpg33170 [Table 1] JPEG2025501127000056.jpg235170JPEG2025501127000057.jpg201170

[0110] Quantum chemical calculations of compounds: Among all the orbitals filled with electrons in a compound, the orbital with the highest energy is called the highest occupied molecular orbital (HOMO). On the other hand, among all the orbitals unfilled with electrons, the orbital with the lowest energy is called the lowest unoccupied molecular orbital (LUMO). The transport of electrons in a material is a process in which electrons are continually removed from the HOMO and added to the LUMO. In quantum chemistry, the degree of overlap between the HOMO and LUMO can be expressed as the orbital overlap integral. The overlap integral is the total spatial integral of the mode product of the two orbital wave functions, its range is 0 to 1, and is defined as follows: ∫|φH(r)||φL(r)|dr Eq. a;

[0111] In formula a, |φH(r)| is the mode of the HOMO orbital wave function, |φL(r)| is the mode of the LUMO orbital wave function, and r represents the position vector. Quantitative calculations were performed on the organic compounds according to the present invention, and the ground state HOMO / LUMO orbital wave functions of the organic compounds were calculated based on DFT / B3LYP / 6-31G(d) using Gaussian 09 software, the orbital overlap integrals of the HOMO and LUMO were calculated, and the HOMO / LUMO energy levels were obtained. As an example, quantitative calculations were performed on organic compounds C1, C2, C5, C7, C9, C12, C13, R1, R2, and R3, and the HOMO / LUMO energy levels and orbital overlap integrals of the compounds are shown in Table 2. Molecular orbital distribution diagrams of organic compounds C1, C2, C5, C7, C9, C12, C13, R1, R2, and R3 are shown in Figures 1 to 10, respectively. JPEG2025501127000058.jpg55170 [Table 2]

[0112] From the molecular orbital distribution diagrams of Table 2 and Figures 1 to 10, it can be seen that in the organic compounds according to the present invention, the group connection site is controlled so that the HOMO and LUMO of the compounds are effectively overlapped on the fluorenyl; compared with the compounds R1, R2, and R3, the orbital overlap integral between the HOMO and LUMO of the compounds C1, C2, C5, C7, C9, C12, and C13 is large, which improves the stability of the organic compounds when transporting carriers in an electric field environment; when the organic compounds are used in organic electroluminescence devices, the stability of the devices can be effectively improved and the operating life of the devices can be extended; on the other hand, the HOMO and LUMO orbital distribution of the comparative compounds shows obvious separation, which may lead to a decrease in stability during charge transport.

[0113] Example 1 An organic electroluminescent device comprising an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (Al) in that order was fabricated according to the following method.

[0114] (1) A glass plate coated with an ITO transparent conductive layer (anode) was ultrasonically treated with a commercially available cleaning agent, rinsed with deionized water, ultrasonically removed oil in an acetone / ethanol mixed solvent, baked in a clean environment until moisture was completely removed, cleaned with ultraviolet light and ozone, and irradiated with a low-energy positive ion beam on the surface.

[0115] (2) Place the above glass substrate with an anode in a vacuum chamber and measure 1×10 -5 The vacuum was drawn to less than Pa, and a mixture of HT-4:HI-3 (97 / 3, w / w) was vacuum-deposited in order to 10 nm on the anode layer as a hole injection layer.

[0116] (3) As a hole transport layer, compound HT-4 was vacuum-deposited on the hole injection layer to a thickness of 60 nm.

[0117] (4) As an electron blocking layer, the organic compound C2 according to the present invention was vacuum-deposited on the hole transport layer to a thickness of 5 nm.

[0118] (5) The light-emitting layer containing the host material and dye material of the device was vacuum-deposited on the electron-blocking layer using a multi-source co-evaporation method, where the deposition rate of the host material BFH-4 was adjusted to 0.1 nm / s, the deposition rate of the dye BFD-16 was set to 3% of the host material, and the total deposition thickness was 20 nm.

[0119] (6) 5 nm of ET-23 was vacuum-deposited on the light-emitting layer as a hole-blocking layer.

[0120] (7) A 25 nm thick mixture of compounds ET-69:ET-57 (50 / 50, w / w) was vacuum deposited on the hole blocking layer as an electron transport layer.

[0121] (8) LiF was vacuum-deposited on the electron transport layer to a thickness of 0.5 nm as an electron injection layer, and a 150 nm thick aluminum metal was used as the cathode to obtain the organic electroluminescence device. The total deposition rate of all organic layers and LiF was controlled to 0.1 nm / s, and the deposition rate of the metal electrode was controlled to 1 nm / s.

[0122] Examples 2 to 20, Comparative Examples 1 to 4 Compared with Example 1, the following organic electroluminescence devices were manufactured, except that the organic compound C2, which is the material of the electron blocking layer in step (4), was changed to the organic compound in Table 3. Among them, the structures of the electron blocking layer materials of Comparative Examples 1 to 4 are as follows. JPEG2025501127000060.jpg50170

[0123] The organic electroluminescence devices according to the above Examples 1 to 20 and Comparative Examples 1 to 4 were subjected to the following characteristic tests.

[0124] (1) At the same luminance, the driving voltage, current efficiency, and device life of the organic electroluminescence device were measured. Specifically, the voltage was increased at a rate of 0.1 V per second until the luminance of the organic electroluminescence device reached 1000 cd / m 2The driving voltage at which the luminance reached 1000 mA was measured, and the current density at this time was measured. The ratio of the luminance to the current density is the current efficiency.

[0125] (2) The life test for LT97 is as follows: 40mA / cm 2 A constant current was maintained and the time (h) for the luminance of the organic electroluminescence device to decrease to 97% was measured.

[0126] The test results are shown in Table 3. [Table 3] JPEG2025501127000062.jpg79170

[0127] From the data in Table 3, it can be seen that the organic compound according to the present invention, when used as an electron blocking layer material in an organic electroluminescence device, has a high current efficiency of more than 9.1 cd / A and a maximum current efficiency of 40 mA / cm when the luminance of the device reaches 1000 cd / m2. 2 The LT97 lifetime at 1000K reaches 67h or more, and the better LT97 lifetime exceeds 72h and even exceeds 89h. Compared with Comparative Examples 1 to 4, it was found that the current efficiency can be effectively improved and the device lifetime can be extended. The reason is believed to be that the material of the present invention has better hole mobility, which makes the exciton recombination region of the device further away from the interface, effectively extending the device lifetime, and also increases the orbital overlap integral between the HOMO and LUMO of the material, improving the stability during charge transport. Among them, the organic compound C13 shows the highest efficiency reaching 9.82cd / A, which is believed to be because its adamantyl further improves the exciton blocking efficiency, increases the utilization rate of excitons, and improves the device efficiency.

[0128] Example 21 An organic electroluminescent device comprising an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (Al) in that order was fabricated according to the following method.

[0129] (1) A glass plate coated with an ITO transparent conductive layer (anode) was ultrasonically treated with a commercially available cleaning agent, rinsed with deionized water, ultrasonically removed oil in an acetone / ethanol mixed solvent, baked in a clean environment until moisture was completely removed, cleaned with ultraviolet light and ozone, and irradiated with a low-energy positive ion beam on the surface.

[0130] (2) Place the above glass substrate with an anode in a vacuum chamber and measure 1×10 -5 The vacuum was drawn to less than Pa, and a mixture of the organic compound C1 and HI-3 (97 / 3, w / w) according to the present invention was vacuum-deposited in order to form a hole-injecting layer on the anode layer film at a thickness of 10 nm.

[0131] (3) As a hole transport layer, the organic compound C1 was vacuum-deposited on the hole injection layer to a thickness of 60 nm.

[0132] (4) As an electron blocking layer, compound HT18 was vacuum-deposited on the hole transport layer to a thickness of 5 nm.

[0133] (5) The light-emitting layer containing the host material and dye material of the device was vacuum-deposited on the electron-blocking layer using a multi-source co-evaporation method, where the deposition rate of the host material BFH-4 was adjusted to 0.1 nm / s, the deposition rate of the dye BFD-16 was set to 3% of the host material, and the total deposition thickness was 20 nm.

[0134] (6) 5 nm of ET-23 was vacuum-deposited on the light-emitting layer as a hole-blocking layer.

[0135] (7) A 25 nm thick mixture of compounds ET-69:ET-57 (50 / 50, w / w) was vacuum deposited on the hole blocking layer as an electron transport layer.

[0136] (8) LiF was vacuum-deposited on the electron transport layer to a thickness of 0.5 nm as an electron injection layer, and a 150 nm thick aluminum metal was used as the cathode to obtain the organic electroluminescence device. The total deposition rate of all organic layers and LiF was controlled to 0.1 nm / s, and the deposition rate of the metal electrode was controlled to 1 nm / s.

[0137] Examples 22 to 32, Comparative Examples 5 to 8 The following organic electroluminescence devices were produced in the same manner as in Example 21, except that the material organic compound C1 of the hole transport layer was changed to an organic compound in Table 4 in step (5).

[0138] The structures of the hole transport layer materials of Comparative Examples 5 to 8 are as follows. JPEG2025501127000063.jpg52170

[0139] The organic electroluminescence devices according to the above-mentioned Examples 21 to 32 and Comparative Examples 5 to 8 were subjected to characteristic tests in the same manner as in Example 1, and the obtained test results are shown in Table 4. [Table 4] JPEG2025501127000065.jpg56170

[0140] From the characteristic data in Table 4, in comparison with Comparative Examples 5 to 8, the organic compound according to the present invention has a current density of 40 mA / cm when used as a hole transport layer material in an organic electroluminescence device. 2 It was found that the LT97 lifetime measured by the method of the present invention reaches more than 100h. This is believed to be because the material of the present invention has better hole mobility, which makes the exciton recombination region of the device further away from the interface, effectively extending the device lifetime, and the orbital overlap integral between the HOMO and LUMO of the material is larger, which results in improved stability during the charge transfer process, and the device lifetime shows obvious advantages.

[0141] As described above, the organic compound of the present invention has a specific molecular structure design, and thus has the advantages of suitable overall properties, particularly excellent stability, and is expected to be sufficiently used in practical production.

[0142] The present invention has been described in detail through the above examples, but the present invention is not limited to the above detailed methods, i.e., it does not mean that the present invention must be carried out depending on the above detailed methods. It is obvious to those skilled in the art that any improvements to the present invention, equivalent replacement of each raw material of the product of the present invention, addition of auxiliary ingredients, selection of specific methods, etc. are all within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound The organic compound has a structure according to Formula I: Here, R １ , R ２ , R ３ , and R ４ are each independently any one selected from a substituted or unsubstituted C1 to C30 linear or branched alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C6 to C30 aryl, and a substituted or unsubstituted C3 to C30 heteroaryl; The R １ and R ２ are not linked or are linked by a chemical bond to form a ring, ３ and R ４ are unlinked or linked by a chemical bond to form a ring; R ５ and R ６ are each independently any one selected from a substituted or unsubstituted C1 to C30 linear or branched alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C6 to C30 aryl, and a substituted or unsubstituted C3 to C30 heteroaryl; L １ and L ２ each independently represents one selected from a single bond, a substituted or unsubstituted C6 to C30 alkylene, and a substituted or unsubstituted C3 to C30 heteroarylene; R １ , R ２ , R ３ , R ４ , R ５ , R ６ , L １ , and L ２ The substituents for substitution in the formula (I) are each independently at least one selected from C1 to C20 linear or branched alkyl, C3 to C20 cycloalkyl, C6 to C30 arylamino, C3 to C30 heteroarylamino, C6 to C30 aryl, or C3 to C30 heteroaryl; Cy is any one selected from the group consisting of substituted or unsubstituted C6 to C30 aryl and substituted or unsubstituted C3 to C30 heteroaryl; The substituents for substitution in Cy are each independently at least one selected from a C3 to C20 cycloalkyl, a C6 to C30 arylamino, a C3 to C30 heteroarylamino, a C6 to C30 aryl, or a C3 to C30 heteroaryl; n １ , and n ２ are each independently selected from an integer of 0 to 4; n １ If ≧2, R ５ are the same or different, and adjacent R ５ is not connected, and n ２ If ≧2, R ６ are the same or different, and adjacent R ６ is not linked to the organic compound.

2. The R １ , R ２ , R ３ , and R ４ are each independently any one selected from a substituted or unsubstituted C1 to C30 linear or branched alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, and a substituted or unsubstituted C6 to C30 aryl; The R １ and R ２ is not connected or is connected to ring A by a chemical bond １ and R ３ and R ４ is not connected or is connected to ring A by a chemical bond ２ Forming The ring A １ , and ring A ２ are each independently any one selected from a C3 to C20 alicyclic ring or a C6 to C30 aromatic ring.

3. The R １ , R ２ , R ３ , and R ４ are each independently any one selected from substituted or unsubstituted C1 to C6 linear or branched alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, and substituted or unsubstituted C6 to C20 aryl; The R １ and R ２ is not connected or is connected to ring A by a chemical bond １ and R ３ and R ４ is not connected or is connected to ring A by a chemical bond ２ Forming The ring A １ and Ring A ２ are each independently any one selected from a C3 to C12 alicyclic ring or a C10 to C20 aromatic ring, Preferably, the ring A １ and Ring A ２ and each independently represent any one selected from the group consisting of an adamantane ring, a fluorene ring, and a benzofluorene ring.

4. The R ５ and R ６ are each independently any one selected from substituted or unsubstituted C1 to C6 linear or branched alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, and substituted or unsubstituted C6 to C20 aryl; Preferably, the R ５ and R ６ are each independently selected from phenyl, biphenyl, or naphthyl; Preferably, the n １ and n ２ The organic compound according to claim 1 , wherein each of the is independently 0 or 1.

5. Said L １ and L ２ are each independently any one selected from a single bond, a substituted or unsubstituted C6 to C20 alkylene, and a substituted or unsubstituted C3 to C20 heteroarylene; Preferably, the L １ and L ２ are each independently any one selected from a single bond and the following substituted or unsubstituted groups:

2. The organic compound according to claim 1, wherein the dashed lines represent linkage sites of groups.

6. Cy is any one selected from substituted or unsubstituted C6 to C20 aryl; Preferably, said Cy is selected from the following substituted or unsubstituted groups:

2. The organic compound according to claim 1, wherein the dashed lines represent linkage sites of groups.

7. The organic compound according to claim 1, characterized in that it has any one of the structures represented by C1 to C318 below:

8. Use of the organic compound according to any one of claims 1 to 7 The organic compound is used in an organic electroluminescent device, Preferably, the organic compound is used as an electron blocking layer material and / or a hole transport layer material in an organic electroluminescent device; Preferably, the use of said organic compound is characterized in that said organic compound is used as a hole injection layer material in an organic electroluminescent device.

9. An arylamine-based organic compound, The arylamine organic compound is characterized in that, in a ground state structure optimized at the B3LYP / 6-31G(d) calculation level, the orbital overlap integral between HOMO and LUMO is greater than 0.

6.

10. The arylamine-based organic compound according to claim 9, comprising the organic compound according to any one of claims 1 to 7.

11. Use of the arylamine organic compound according to claim 9 or 10, The arylamine-based organic compound is used in an organic electroluminescence device, Preferably, the arylamine-based organic compound is used as an electron blocking layer material and / or a hole transport layer material in an organic electroluminescent device; Preferably, the use of an arylamine-based organic compound according to claim 9 or 10, characterized in that the arylamine-based organic compound is used as a hole injection layer material in an organic electroluminescent device.

12. 1. An organic electroluminescent device comprising: The organic electroluminescence device includes a first electrode, a second electrode, and at least one organic layer provided between the first electrode and the second electrode, the organic layer including at least one organic compound according to any one of claims 1 to 7 and / or an arylamine-based organic compound according to claim 9 or 10.

13. The organic layer comprises a hole transport layer, and the hole transport layer comprises at least one organic compound according to any one of claims 1 to 7 and / or an arylamine-based organic compound according to claim 9 or 10. The organic electroluminescence device according to claim 12.

14. The organic layer includes an electron blocking layer, and the electron blocking layer includes at least one organic compound according to any one of claims 1 to 7 and / or at least one arylamine-based organic compound according to claim 9 or 10. The organic electroluminescence device according to claim 12.

15. The organic layer comprises a hole injection layer, and the hole injection layer comprises at least one organic compound according to any one of claims 1 to 7 and / or an arylamine-based organic compound according to claim 9 or 10. The organic electroluminescence device according to claim 12.

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