An organic compound and an organic electroluminescence device comprising the same

Abstract

The application provides an organic compound and an organic electroluminescent device containing the same, the organic compound has a structure as shown in formula I, by introducing a dibenzo five-membered ring fused unit at the meta position of aniline, the size of steric hindrance can be adjusted, the twist degree of the molecule can be effectively controlled, and the crystallinity of the molecule is reduced; meanwhile, an aromatic group is introduced at the ortho position, the packing density of the molecule can be effectively controlled, the LUMO and HOMO energy levels are optimized, the refractive performance of the molecule is improved, the diffusion of excitons to the hole layer is effectively blocked, and an organic electroluminescent material with a more optimal spatial structure and a better thin film stacking morphology is obtained. The organic compound is used in an organic electroluminescent device, as an electron blocking material, the driving voltage of the device can be reduced, the luminous efficiency is improved, and the comprehensive performance is significantly improved.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic electroluminescent materials, and particularly relates to an organic compound and an organic electroluminescent device comprising the same. BACKGROUND

[0002] In recent years, optoelectronic devices based on organic materials have attracted much attention. The inherent flexibility of organic materials makes them very suitable for manufacturing on flexible substrates, and they can be designed and produced as beautiful and cool optoelectronic products, which have incomparable advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLEDs have developed particularly rapidly and have achieved commercial success in the field of information display. OLEDs can provide high saturation of red, green and blue colors, and full-color display devices made of them do not require additional backlights, and have the advantages of colorful, thin and flexible.

[0003] OLED devices are usually of sandwich type structure, comprising two electrodes and an organic thin film layer sandwiched between the two electrodes; the core of the OLED device is an organic thin film layer containing various organic functional materials. Common organic functional materials include hole injection material, hole transport material, hole blocking material, electron injection material, electron transport material, electron blocking material, light-emitting host material and light-emitting guest (dye), etc. When a voltage is applied to the two electrodes of the OLED device, electrons and holes are injected and transported to the light-emitting region and recombine there, generating excitons and emitting light.

[0004] With the continuous development of organic optoelectronic technology, people have developed various organic materials, combined with various novel device structures, which can improve the carrier mobility, control the carrier balance, break through the electroluminescent efficiency, and delay the device decay. Due to quantum mechanics, common fluorescent emitters mainly utilize singlet excitons generated when electrons and holes combine to emit light, and are still widely used in various OLED products. Some metal complexes (such as iridium complexes) can emit light using both triplet and singlet excitons, known as phosphorescent emitters, which have up to 4 times higher energy conversion efficiency than traditional fluorescent emitters. The technology of thermally activated delayed fluorescence (TADF) promotes the transition of triplet excitons to singlet excitons, which can effectively utilize triplet excitons without using metal complexes to achieve high luminescent efficiency. The technology of thermally activated sensitized fluorescence (TASF) uses materials with TADF properties to sensitize emitters through energy transfer, which also achieves high luminescent efficiency.

[0005] As OLED products gradually enter the market, people have increasingly higher requirements for their performance. Current OLED materials and device structures cannot fully solve the problems related to efficiency, lifespan, and cost of OLED products.

[0006] Therefore, there is an urgent need in this field to develop an organic electroluminescent material that can improve the luminous efficiency of OLED devices, reduce the driving voltage, and extend their lifespan. Summary of the Invention

[0007] To address the shortcomings of existing technologies, the present invention aims to provide an organic compound and an organic electroluminescent device containing the same. The organic compound possesses excellent photoelectric properties and is suitable as an electron blocking layer material and / or hole transport layer material when applied to an organic electroluminescent device. This improves the luminous efficiency of the device, reduces the driving voltage, and comprehensively enhances the device's performance.

[0008] To achieve this objective, the present invention adopts the following technical solution:

[0009] One object of the present invention is to provide an organic compound having the structure shown in Formula I:

[0010]

[0011] In Formula I, Ar1 is selected from any one of substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C3-C30 heteroaryl groups.

[0012] In Formula I, Ar2 and Ar3 are each independently selected from any one of substituted or unsubstituted C6-C22 aryl and substituted or unsubstituted C3-C22 heteroaryl groups.

[0013] In Formula I, L is selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene.

[0014] In this invention, "L is a single bond" means that Ar1 is connected to the benzene ring by a single bond; the same description used below has the same meaning.

[0015] In Formula I, Y is selected from O, S, CR1R2 or SiR3R4.

[0016] R1, R2, R3, R4are each independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; R1and R2are not connected or connected by a chemical bond to form a ring, R3and R4are not connected or connected by a chemical bond to form a ring.

[0017] R f1 , R f2 , R f3 are each independently selected from any one of halogen, cyano, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0018] Ar1, Ar2, Ar3, L, R1, R2, R3, R4, R f1 , R f2 , R f3 are each independently selected from at least one of halogen, C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl or C3-C30 heteroaryl.

[0019] k1, k2 are each independently an integer from 0 to 3, for example, can be 0, 1, 2 or 3; k3 is an integer from 0 to 4, for example, can be 0, 1, 2, 3 or 4.

[0020] The organic compound provided by the present application has a structure shown in formula I, wherein a specific type of dibenzo five-membered ring fused unit is introduced at the meta position of the aniline structure Not only can the size of steric hindrance be adjusted, but also the twist degree of the molecule can be effectively controlled to reduce the crystallinity of the molecule; at the same time, the aromatic group Ar1 is connected at the ortho position (2-position), which can effectively control the packing density of the molecule, optimize the LUMO and HOMO energy levels, improve the refractive performance of the molecule, and effectively block the diffusion of excitons to the hole layer, so as to obtain an organic electroluminescent material with more optimal spatial structure and better thin film stacking morphology. The organic compound is used for an organic electroluminescent device, and is suitable as an electron blocking layer material and / or a hole transport layer material, which can effectively improve the luminous efficiency, reduce the driving voltage, and comprehensively improve the luminous performance of the device.

[0021] It should be noted that the possible effects of each group / characteristic are described separately in the present application for the sake of convenience of description, but this does not mean that these groups / characteristics act in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the whole molecule, which is the result of the synergistic effect between each group, rather than the effect of a single group.

[0022] In the present application, the halogen can be fluorine, chlorine, bromine or iodine. The same description is referred to below, which has the same meaning.

[0023] In the present application, the "substituted or unsubstituted" group can be substituted with one substituent or multiple substituents, and when the substituents are multiple (at least two), they can be the same or different substituents; the same expression is referred to below, which has the same meaning, and the selection range of the substituents is as shown above, which will not be described one by one.

[0024] In the present application, if no special description is given, the description of chemical elements contains the concept of isotopes with the same chemical properties, for example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0025] In the present application, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, Si or Se.

[0026] In the present application, the expression of the ring structure with a dash through it represents the connection site at any position on the ring structure that can form a bond.

[0027] In the present application, the expression of Ca-Cb represents that the number of carbon atoms of the group is a-b, and unless otherwise specified, in general, the number of carbon atoms does not include the number of carbon atoms of the substituent. For example, taking 9,9-diphenylfluorenyl as an example, it is a fluorenyl group substituted with two phenyl groups, and the number of carbon atoms of the group refers to the number of carbon atoms of the fluorenyl group, that is, C13 aryl.

[0028] In the present specification, "independently of each other" means that when the subject has multiple, they can be the same or different.

[0029] In the present application, the C6-C30 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0030] The C3-C30 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.

[0031] The C6-C22 can be C6, C9, C10, C12, C14, C16, C18, or C20, etc.

[0032] The C3-C22 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, or C20, etc.

[0033] The C1-C20 can be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, or C19, etc.

[0034] The C3-C20 can be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, or C19, etc.

[0035] The C2-C12 can be C3, C4, C5, C6, C7, C8, C9, C10, or C11, etc.

[0036] The C1-C10 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, or C10.

[0037] The C3-C10 can be C3, C4, C5, C6, C7, C8, C9, or C10.

[0038] The C2-C10 can be C2, C3, C4, C5, C6, C7, C8, C9, or C10.

[0039] In the present application, the C6-C30 aryl, preferably C6-C20 aryl, includes monocyclic aryl and fused ring aryl; the monocyclic aryl means a group containing at least one phenyl, and when containing at least two phenyls, the phenyls are connected by a single bond, and exemplarily includes but is not limited to phenyl, biphenyl, terphenyl, etc.; the fused ring aryl means a group containing at least two aromatic rings, and the aromatic rings are fused to each other by sharing two adjacent carbon atoms, and exemplarily includes but is not limited to naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthene, triphenylene, pyrene, perylene, etc. Group or naphthyl group, etc.

[0040] The C3-C30 heteroaryl group includes monocyclic heteroaryl group and fused ring heteroaryl group. The monocyclic heteroaryl group means a group having at least one heteroaryl group in the molecule, and when the molecule has one heteroaryl group and other groups (e.g., aryl group, heteroaryl group, alkyl group, etc.), the heteroaryl group and the other groups are connected by a single bond, and exemplarily includes, but is not limited to, furyl group, thienyl group, pyrrolyl group, pyridyl group, etc. The fused ring heteroaryl group means a group having at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) in the molecule, and the two rings are fused to each other by sharing two adjacent atoms, and exemplarily includes, but is not limited to, benzofuryl group, benzothienyl group, isobenzofuryl group, isobenzothienyl group, indolyl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group and its derivatives (N-phenylcarbazolyl group, N-naphthylcarbazolyl group, benzocarbazolyl group, diphenylcarbazolyl group, indolocarbazolyl group, azacarbazolyl group, etc.), acridyl group, phenothiazinyl group, phenoxazinyl group, hydrogenated acridyl group, etc.

[0041] Specific examples of the arylene group described below in the present application can be exemplified by bivalent groups obtained by removing one hydrogen atom from the examples of the aryl group described above; and specific examples of the heteroarylene group can be exemplified by bivalent groups obtained by removing one hydrogen atom from the examples of the heteroaryl group described above.

[0042] The C1-C20 straight chain or branched alkyl group exemplarily includes, but is not limited to, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, n-octyl group, n-heptyl group, n-nonyl group, n-decyl group, etc.

[0043] The C3-C20 cycloalkyl group exemplarily includes, but is not limited to, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, adamantyl group, etc.

[0044] Preferably, the Ar1 is selected from any one of the following groups which are substituted or unsubstituted:

[0045]

[0046] wherein the wavy line represents a connecting site of the group;

[0047] X1is selected from O, S, CR 11 R 12 , NR 13 or SiR 14 R 15 ;

[0048] R 11 , R 12 , R 13 , R 14 , R 15each independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; R 11 and R 12 are not connected or are connected by a chemical bond to form a ring, R 14 and R 15 are not connected or are connected by a chemical bond to form a ring.

[0049] Preferably, said R 11 , R 12 , R 13 , R 14 , R 15 are each independently methyl or phenyl.

[0050] Preferably, said Ar1is selected from any one of the following groups, which are substituted or unsubstituted: wherein the wavy line represents the point of attachment of the group.

[0051] Preferably, said L is selected from any one of a single bond, substituted or unsubstituted:

[0052]

[0053] wherein the wavy line represents the point of attachment of the group.

[0054] Preferably, said L is a single bond or a phenylene group.

[0055] Preferably, when said L is a single bond, said Ar1is not a phenyl group.

[0056] Preferably, said Ar2, Ar3are selected from any one of the following groups, which are substituted or unsubstituted:

[0057]

[0058] wherein the wavy line represents the point of attachment of the group;

[0059] L' is selected from any one of a single bond, C6-C10 arylene or C3-C10 heteroarylene;

[0060] X2is selected from O, S, CR 21 R 22 , NR 23 or SiR 24 R 25 ;

[0061] R 21 、R 22 、R 23 、R 24 、R 25 each independently is selected from any one of hydrogen, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; R 21 and R 22 are not connected or are connected by a chemical bond to form a ring, R 24 and R 25 are not connected or are connected by a chemical bond to form a ring.

[0062] Preferably, the L' is a single bond or a phenylene group.

[0063] Preferably, the R 21 , R 22 , R 23 , R 24 , R 25 each independently is a methyl group or a phenyl group.

[0064] Preferably, the Ar2, Ar3 each independently is selected from any one of substituted or unsubstituted:

[0065]

[0066]

[0067] wherein the wavy line represents the point of attachment of the group.

[0068] Preferably, the R1, R2, R3, R4 each independently is selected from substituted or unsubstituted C1-C6 linear or branched alkyl, substituted or unsubstituted C6-C12 aryl.

[0069] Preferably, the R1, R2, R3, R4 each is a methyl group.

[0070] Preferably, the R f1 , R f2 , R f3 each independently is selected from any one of halogen, cyano, substituted or unsubstituted C1-C6 linear or branched alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl.

[0071] Preferably, the k1, k2, k3 each is 0.

[0072] When a substituent group is present in the "substituted or unsubstituted" mentioned above in this invention, each substituent group is independently selected from at least one of halogen, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, or C3-C30 heteroaryl.

[0073] Preferably, each of the substituents is independently selected from at least one of halogen, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C2-C10 heterocycloalkyl, C6-C30 aryl or C3-C30 heteroaryl.

[0074] Preferably, the organic compound has any one of the structures shown in P1-P984 below:

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

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[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117] The second object of the present application is to provide the organic compound according to the first object for use in an organic electroluminescence device.

[0118] Preferably, the organic compound is used as an electron blocking material and / or a hole transporting material in the organic electroluminescence device.

[0119] In addition to the organic electroluminescence device, the organic compound of the present application can also be applied to other types of organic electronic devices, including organic field effect transistors, organic thin film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners or electronic paper.

[0120] The third object of the present application is to provide an organic electroluminescence 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 comprises at least one organic compound according to the first object.

[0121] The organic compound provided by the present application is used in an organic electroluminescence device as an electron blocking layer material, which can effectively improve the luminous efficiency of the organic electroluminescence device and reduce the driving voltage, so that the device has better comprehensive performance, and is especially suitable for green light electron blocking layer materials.

[0122] Preferably, the organic layer comprises an electron blocking layer, and the electron blocking layer comprises at least one organic compound according to the first object.

[0123] Preferably, the organic layer comprises a hole transporting layer, and the hole transporting layer comprises at least one organic compound according to the first object.

[0124] In a specific technical solution, the organic electroluminescence device comprises a substrate, an anode layer, a plurality of light-emitting functional layers and a cathode layer formed in sequence on the substrate; the light-emitting functional layers comprise at least one of a hole injection layer, a hole transporting layer, a light-emitting layer, an electron blocking layer and an electron transporting layer; wherein the electron blocking layer and / or the hole transporting layer contain at least one organic compound according to the first object; preferably, the electron blocking layer contains at least one organic compound according to the first object.

[0125] In a specific technical solution, the organic electroluminescence device (OLED) comprises a first electrode and a second electrode, and an organic layer between the first electrode and the second electrode. The organic layer can be further divided into multiple regions, for example, comprising a hole transporting region, a light-emitting layer and an electron transporting region.

[0126] In the specific embodiments, a substrate can be used under the first electrode or on the second electrode. The substrates are glass or polymer materials having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) can be provided on the substrate for display.

[0127] The first electrode can be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (Sn02), zinc oxide (ZnO), and other oxide transparent conductive materials and any combination thereof can be used. When the first electrode is used as a cathode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and other metals or alloys and any combination thereof can be used.

[0128] The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, and other methods. The compounds used as the organic layer can be small organic molecules, large organic molecules, or polymers, and combinations thereof.

[0129] The hole transport zone is located between the anode and the light-emitting layer. The hole transport zone can be a single-layer hole transport layer (HTL) including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport zone can also be a multi-layer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer; the HTL and / or the EBL contain at least one organic compound having the structure of Formula I, and it is further preferred that the EBL contain at least one organic compound having the structure of Formula I.

[0130] The materials of the hole transport zone can also be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphor sulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0131]

[0132]

[0133]

[0134] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can employ one or more of the compounds described above as HT-1 to HT-51, or one or more of the compounds described below as HI-1 to HI-3; or one or more of the compounds described above as HT-1 to HT-51 doped with one or more of the compounds described below as HI-1 to HI-3.

[0135]

[0136] The light emitting layer includes light emitting dyes (i.e., dopants) that can emit different wavelengths of light, and can also include host materials. The light emitting layer can be a single color light emitting layer that emits a single color such as red, green, blue, etc. Multiple different color single color light emitting layers can be arranged in a planar pattern according to a pixel pattern, or can be stacked together to form a color light emitting layer. When different color light emitting layers are stacked together, they can be separated from each other or connected to each other. The light emitting layer can also be a single color light emitting layer that can emit multiple different colors such as red, green, blue, etc.

[0137] Depending on the technology, the light emitting layer material can employ different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescent light emitting materials, etc. In an OLED device, a single light emitting technology can be employed, or a combination of multiple different light emitting technologies can be employed. These different light emitting materials classified by technology can emit the same color of light, or can emit different colors of light.

[0138] In an aspect of the present application, the light emitting layer employs a fluorescent electroluminescent technology. The fluorescent host material of the light emitting layer can be selected from, but not limited to, a combination of one or more of the following listed BFH-1 to BFH-17.

[0139]

[0140] In an aspect of the present application, the light emitting layer employs a fluorescent electroluminescent technology. The fluorescent dopant of the light emitting layer can be selected from, but not limited to, a combination of one or more of the following listed BFD-1 to BFD-24.

[0141]

[0142]

[0143] In an aspect of the present application, the light emitting layer employs a phosphorescent electroluminescent technology. The host material of the light emitting layer can be selected from, but not limited to, a combination of one or more of PH-1 to PH-85.

[0144]

[0145]

[0146]

[0147]

[0148] In an aspect of the application, the light-emitting layer employs phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, a combination of one or more of the following listed GPD-1 to GPD-47.

[0149]

[0150]

[0151]

[0152] In an aspect of the application, the light-emitting layer employs phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, a combination of one or more of the following listed RPD-1 to RPD-28.

[0153]

[0154]

[0155] In an aspect of the application, the light-emitting layer employs phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, a combination of one or more of the following listed YPD-1 to YPD-11.

[0156]

[0157] The OLED organic layer can also include an electron transport zone between the light-emitting layer and the cathode. The electron transport zone can be an electron transport layer (ETL) of a single layer structure, including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing multiple compounds. The electron transport zone can also 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).

[0158] In an aspect of the application, the electron transport layer material can be selected from, but not limited to, a combination of one or more of the following listed ET-1 to ET-73.

[0159]

[0160]

[0161]

[0162]

[0163] In one aspect of the present application, a hole blocking layer (HBL) is located between the electron transport layer and the light-emitting layer. The hole blocking layer can employ, but is not limited to, one or more compounds of ET-1 to ET-73 described above, or employ, but is not limited to, one or more compounds of PH-1 to PH-46; or employ, but is not limited to, a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0164] The device can further include an electron injection layer located between the electron transport layer and the cathode, and the electron injection layer material includes, but is not limited to, a combination of one or more of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Yb, Li, or Ca.

[0165] Compared with the prior art, the present application has the following beneficial effects:

[0166] The present application provides a novel organic compound, which can adjust the steric hindrance size, effectively control the twist degree of the molecule, and reduce the crystallinity of the molecule by introducing a dibenzo-pentacyclic ring fused unit at the meta position of aniline; meanwhile, the introduction of an aromatic group at the ortho position (2-position) can effectively control the packing density of the molecule, optimize the LUMO and HOMO energy levels, improve the refractive performance of the molecule, and effectively block the diffusion of excitons to the hole layer, so as to obtain an organic electroluminescent material with a more optimal spatial structure and a better thin film stacking morphology. The organic compound is used for an organic electroluminescent device, and as an electron blocking material, can significantly improve the performance of the device, mainly in terms of reducing the voltage and improving the luminous efficiency.

[0167] In addition, the preparation process of the organic compound provided by the present application is simple and easy to operate, the raw materials are easy to obtain, and is suitable for mass production. DETAILED DESCRIPTION

[0168] The technical solutions of the present application are further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only used to help understand the present application, and should not be regarded as a specific limitation on the present application.

[0169] The representative synthesis path of the organic compound of the structure shown in formula I provided by the present application is as follows:

[0170]

[0171] wherein, Ar1, Ar2, Ar3, L, Y, R f1 , Rf2 , R f3 , k1, k2, k3 have the same meaning as in formula I; Pd(PPh3)4 represents tetra-triphenylphosphine palladium, Pd2(dba)3 represents tris(dibenzylacetone)dipalladium(0), Sphos represents 2-dicyclohexylphospho-2',6'-dimethoxybiphenyl, IPr.HCl represents 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride, NaOBu-t represents sodium tert-butoxide, (t-Bu)3P represents tri-tert-butylphosphine.

[0172] The preparation of the organic compound of the structure shown in formula I of the present application includes the above-mentioned method, but is not limited to the above-mentioned method, and the organic compound synthesized by other methods by those skilled in the art also belongs to the protection scope of the present application.

[0173] More specifically, the present application exemplarily provides the specific synthesis method of the organic compound as follows: the solvents and reagents used in the following synthesis examples can be purchased or customized from the chemical product market. In addition, those skilled in the art can also synthesize by other known methods.

[0174] The mass spectrometry characterization data in the following synthesis examples is obtained by testing with a ZAB-HS mass spectrometer manufactured by Micromass Company in the United Kingdom.

[0175] Synthesis Example 1: Organic compound P6

[0176]

[0177] (1) In a 1000 mL single-neck flask, 15 g of M1, 16.8 g of 2-biphenyl boronic acid, 0.8 g of tetra-triphenylphosphine palladium Pd(PPh3)4, 20 g of potassium carbonate, 300 mL of 1,4-dioxane and 100 mL of water were added, vacuumed and replaced with nitrogen for 3 times, the reaction was heated to 90°C for 5 h. After the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction liquid was separated, the organic phase was purified by silica gel column twice, the organic phase was concentrated, methanol was added, refluxed and stirred for 1 h, and then filtered to obtain a light yellow powder M1-1, and then recrystallized with ethyl acetate to obtain a pure product.

[0178] (2) In a 1000 mL three-necked flask, 18.6 g of M1-1, 14.3 g of 9,9-dimethylfluorene-2-boronic acid, 0.5 g of tris(dibenzylideneacetone)dipalladium(0) Pd2(dba)3, 0.5 g of 2-bis(cyclohexylphosphino)-2',6'-dimethoxybiphenyl (Sphos), 19 g of anhydrous potassium phosphate, 300 mL of 1,4-dioxane and 30 mL of water were added, vacuum-nitrogen substitution was performed three times, the reaction was heated to 110°C and reacted for 5 h. After the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction liquid was separated, the organic phase was purified by silica gel column twice, the organic phase was concentrated, methanol was added, reflux stirring was performed for 1 h, and a light yellow powder M1-2 was obtained by filtration, followed by recrystallization with ethyl acetate to obtain a pure product.

[0179] (3) In a 1000 mL three-necked flask, 15.8 g of M1-2, 2 mL of hydrazine hydrate, 0.5 g of palladium on carbon (Pd / C) and 300 mL of ethanol were added, vacuum-nitrogen substitution was performed three times, the reaction was heated to 90°C and reacted for 5 h. After the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction liquid was separated, the organic phase was purified by silica gel column twice, the organic phase was concentrated, methanol was added, reflux stirring was performed for 1 h, and a white powder M1-3 was obtained by filtration, followed by recrystallization with ethyl acetate to obtain a pure product.

[0180] (4) In a 1000 mL single-necked flask, 13.1 g of M1-3, 9.7 g of 1-bromo-9,9-dimethylfluorene, 0.5 g of Pd2(dba)3, 0.5 g of 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPr.HCl), 500 mL of toluene, 12.4 g of sodium tert-butoxide NaOBu-t were added, vacuum-nitrogen substitution was performed three times, the reaction was heated to 90°C and reacted for 5 h. After the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction liquid was separated, the organic phase was purified by silica gel column twice, the organic phase was concentrated, methanol was added, reflux stirring was performed for 1 h, and a light yellow powder M1-4 was obtained by filtration, followed by recrystallization with ethyl acetate to obtain a pure product.

[0181] (5) In a 1000 mL three-necked flask, 16.5 g of M1-4, 10.2 g of bromobenzene, 0.5 g of Pd2(dba)3, 0.5 mL of tri-tert-butylphosphine (t-Bu)3P, 500 mL of toluene, 11.5 g of sodium tert-butoxide were added, vacuum-nitrogen substitution was performed three times, the reaction was heated to 110°C and reacted for 5 h. After the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction liquid was separated, the organic phase was purified by silica gel column twice, the organic phase was concentrated, methanol was added, reflux stirring was performed for 1 h, and a light yellow powder P6 was obtained by filtration, followed by recrystallization with ethyl acetate three times to obtain a pure product.

[0182] Organic compound P6: m / z theoretical value: 705; m / z actual value: 706.

[0183] Synthesis example 2-20

[0184] The process route of synthesis example 2-20 is the same as that of synthesis example 1, except that the raw materials are different, and the raw materials, target product and result characterization data are shown in Table 1.

[0185] Table 1

[0186]

[0187]

[0188]

[0189]

[0190] Example 1

[0191] An organic electroluminescent device comprises an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode (Al) arranged in sequence; the specific preparation method is as follows:

[0192] (1) The glass plate coated with ITO transparent conductive layer (as anode) is treated by ultrasonic in commercial cleaning agent, washed in deionized water, and deoiled in acetone / ethanol mixed solvent by ultrasonic, baked in clean environment until water is completely removed, washed by ultraviolet light and ozone, and the surface is bombarded by low-energy cation beam;

[0193] (2) The glass substrate with anode is placed in a vacuum chamber, vacuumized to <1×10 -5 Pa, and 10 nm of compound HT-4:HI-3 (97 / 3, w / w) mixture is vacuum evaporated on the anode layer film as a hole injection layer, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 10 nm;

[0194] (3) HT-4 is vacuum evaporated on the hole injection layer as a hole transport layer of the device, the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 60 nm;

[0195] (4) The organic compound P6 provided by the application is vacuum evaporated on the hole transport layer as an electron blocking layer of the device, the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 40 nm;

[0196] (5) The light-emitting layer of the device is vacuum evaporated on the electron blocking layer, the light-emitting layer comprises a host material and a dye material, a ternary mixture of host materials PH-61:PH-3:GPD-12 (100:100:20, w / w / w) is adjusted as the light-emitting layer by using the method of multi-source co-evaporation; the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 40 nm;

[0197] (6) Vacuum evaporating electron transport layer material ET-69: ET-57 (50 / 50, w / w) mixture on the light-emitting layer, the evaporation rate is 0.1 nm / s, and the total film thickness is 25 nm;

[0198] (7) Vacuum evaporating LiF with a thickness of 0.5 nm on the electron transport layer (ETL) as an electron injection layer, and evaporating aluminum with a thickness of 150 nm as a cathode of the device to obtain the organic electroluminescent device.

[0199] Examples 2-20 and Comparative Examples 1-3

[0200] An organic electroluminescent device, which is only different from Example 1 in that the electron blocking layer material organic compound P6 in step (4) is replaced by the compound in Table 2.

[0201] The structure of the electron blocking layer material of Comparative Examples 1-3 is as follows:

[0202]

[0203] The sources of Comparative Compounds R1, R2 and R3 can be referred to the prior arts CN110577510A, CN110903276A and WO2021101247A1 respectively.

[0204] Performance test:

[0205] The organic electroluminescent devices provided in Examples 1-20 and Comparative Examples 1-3 above are subjected to the following performance tests, and the specific method is as follows: the voltage is raised at a rate of 0.1 V per second, and when the brightness of the organic electroluminescent device reaches 10000 cd / m 2 , the voltage at this time is measured as the driving voltage; the current density at this time is tested, and the ratio of brightness to current density is the current efficiency; and the test results are shown in Table 2.

[0206] Table 2

[0207]

[0208]

[0209] As can be seen from the data in Table 2, the organic compound used as the electron blocking layer material of the organic electroluminescent device has a current efficiency as high as 62.2-67.4 cd / A, a driving voltage ≤4.2 V, and even as low as 3.9 V when the brightness of the device reaches 10000 cd / m 2 , which can effectively improve the current efficiency, reduce the driving voltage and energy consumption, and is a good electron blocking layer material.

[0210] In summary, compared with the prior art, the application introduces a specific dibenzo five-membered ring fused structure at the meta position of aniline, and introduces a phenyl, biphenyl, 9, 9-dimethylfluorenyl and other aromatic groups at the 2-position. This combination ensures that the molecular space has a certain degree of tortuosity, and a more optimal space structure can be obtained, so that the molecules have a more optimal arrangement when the film is stacked, thereby further improving the light-emitting efficiency of the device, which is at least 15% higher than the compound in the prior art. Changing any one of the aforementioned groups will reduce the light-emitting efficiency. Specifically, in R1 of Comparative Example 1, there is no group connected to the ortho position of aniline, which will affect the spatial structure and packing density of the molecule; in R2 of Comparative Example 2, the dibenzo five-membered ring fused structure at the meta position of aniline is an N-phenyl carbazole group, which has poorer hole transport performance than dibenzofuranyl and fluorenyl; in R3 of Comparative Example 3, the fluorene-9, 9-xanthene fused ring structure directly connected to aniline increases the rigidity of the molecular space, so the overall driving voltage of the three comparative examples is high and the current efficiency is low.

[0211] The applicant declares that the organic compound and the organic electroluminescent device comprising the same of the present application are illustrated by the above-mentioned examples, but the present application is not limited to the above-mentioned examples, i.e. it does not mean that the present application must rely on the above-mentioned examples to be implemented. It should be understood by those skilled in the art that any improvement of the present application, equivalent replacement of each raw material of the product of the present application, addition of auxiliary ingredients, selection of specific modes, etc. fall within the protection scope and disclosure scope of the present application.

Claims

1. An organic compound characterized in that, The organic compound has a structure as shown in Formula I: Formula I; Ar1 is selected from any one of the following groups: 、 、 、 、 、 、 、 、 ； The wavy line represents the connecting site of the group; X1is selected from CR 11 R 12 , NR 13 or SiR 14 R 15 ; R 11 , R 12 , R 13 , R 14 , R 15 each independently is selected from any one of hydrogen, C1-C20 straight chain or branched alkyl; Ar2 and Ar3 are each independently selected from any one of the following groups: 、 、 、 、 、 、 、 、 、 、 、 、 、 ； L' is selected from a single bond; L is selected from a single bond; Y is selected from O, S, CR1R2 or SiR3R4; R1, R2, R3 and R4 are each methyl; R f1 , R f2 , R f3 each independently is selected from any one of halogen, cyano, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; R f1 , R f2 , R f3 each of the substituents of the substituents described in R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, R35, R36, R37, R38, R39, R40, R41, R42, R43, R44, R45, R46, R47, R48, R49, R50, R51, R52, R53, R54, R55, R56, R57, R58, R59, R60, R61, R62, R63, R64, R65, R66, R67, R68, R69, R70, R71, R72, R73, R74, R75, R76, R77 k1, k2 and k3 are each 0.

2. The organic compound according to claim 1, characterized by R 11 , R 12 , R 13 , R 14 , R 15 each independently is methyl.

3. The organic compound according to claim 1, wherein The Ar1 is selected from any one of the following groups: 、 ； The wavy line represents the connecting site of the group.

4. The organic compound according to claim 1, wherein The Ar2 and Ar3 are each independently selected from any one of the following groups: 、 、 、 、 、 、 、 、 、 、 、 ； The wavy line represents the connecting site of the group.

5. The organic compound according to claim 1, wherein The organic compound has any one of the structures as shown below: ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； 。 6. Use of the organic compound according to any one of claims 1 to 5, wherein The organic compound is applied to an organic electroluminescence device.

7. The use of the organic compound according to claim 6, characterized by The organic compound is used as an electron blocking material and / or a hole transporting material in an organic electroluminescence device.

8. An organic electroluminescent device, characterized by The organic electroluminescence device comprises a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one organic compound as claimed in any one of claims 1-5.

9. The organic electroluminescent device according to claim 8, characterized in that The organic layer comprises an electron blocking layer, and the electron blocking layer comprises at least one organic compound as claimed in any one of claims 1-5.

10. The organic electroluminescent device according to claim 8, characterized in that, The organic layer comprises a hole transporting layer, and the hole transporting layer comprises at least one organic compound as claimed in any one of claims 1-5.

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