An organic compound and its application and an organic electroluminescent device containing the same

Abstract

The present invention relates to a compound and its application and an organic electroluminescent device containing the compound, wherein the compound has a structure shown in the following formula. The core structure of the compound provided by the present invention is a naphthylamine mother core obtained by replacing the α position of the naphthyl group with a condensed aromatic ring. By adopting the combination of the condensed aromatic ring with good conjugation ability and the naphthyl group, it is beneficial to improve the charge mobility of the compound molecule. By introducing the condensed aromatic ring or condensed heterocyclic structure by bridging other aromatic groups in the mother core, it can be ensured that the compound molecule has a good conjugated planar structure and thermal stability. When the present invention is used in an organic electroluminescent device, the current efficiency can be effectively improved and the voltage can be reduced.

Description

Technical Field

[0001] The invention relates to a compound, belonging to the technical field of organic light-emitting materials, and also relates to the application of the compound and an organic electroluminescent device containing the compound. Background Art

[0002] In recent years, optoelectronic devices based on organic materials have developed rapidly and become a hot topic in the field. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLED has developed particularly rapidly and has achieved commercial success in the field of information display. OLED can provide highly saturated red, green, and blue colors. Full-color display devices made of OLED do not require additional backlight sources and have the advantages of brilliant colors, lightness, thinness, and softness.

[0003] The core of OLED devices is a multi-layer thin film structure containing a variety of organic functional materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, luminescent host materials and luminescent guest (dyes), etc. When power is turned on, electrons and holes are injected and transported to the luminescent area respectively and recombine there, thereby generating excitons and emitting light.

[0004] Common fluorescent emitters mainly emit light using singlet excitons generated when electrons and holes combine, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can simultaneously use triplet excitons and singlet excitons to emit light, and are called phosphorescent emitters. Their energy conversion efficiency can be increased by up to four times compared to traditional fluorescent emitters. Thermally excited delayed fluorescence (TADF) technology promotes the transformation of triplet excitons to singlet excitons. Without the use of metal complexes, triplet excitons can still be effectively utilized to achieve higher luminescence efficiency. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the emitter through energy transfer, which can also achieve higher luminescence efficiency.

[0005] Hole transport materials have a significant impact on the voltage of the device. On the other hand, hole transport materials also regulate the transport balance of carriers in the device. Improving the carrier mobility of hole transport materials can improve the luminous efficiency and delay the attenuation of the device. Although products using OLED display technology have been commercialized, there is still a need to continuously improve the life and efficiency of the device to meet people's pursuit of higher quality. Therefore, this field is in urgent need of developing more types of organic materials for use in organic electroluminescent devices, so that the devices have higher luminous efficiency, lower driving voltage and longer service life. Summary of the invention

[0006] In order to further meet the ever-increasing demand for the optoelectronic performance of OLED devices and the energy-saving needs of mobile electronic devices, it is necessary to develop new and efficient OLED materials, among which the development of new hole transport materials with high hole injection ability and high mobility is of great significance.

[0007] The object of the present invention is to provide a compound, which can be used as an organic thin layer material in an organic electroluminescent device, so that the device has high luminous efficiency and a long service life.

[0008] The inventor has devoted himself to research and found that an amine-based core compound with an α-position of a naphthyl group substituted with a condensed aromatic ring, which has excellent hole transport ability, can be used to obtain a class of excellent hole transport layer materials through a certain structural molecular structure design. The characteristic is that one of the substituents of the amine group introduces a condensed aromatic ring or condensed heterocyclic structure with good conjugated planar structure and thermal stability, and the other substituent is a phenyl structure with an ortho-substituted aromatic group. The above-mentioned material of the present invention can also be used as an electron blocking layer material, and the performance is also excellent.

[0009] Specifically, the present invention provides an organic compound having a structure as shown in formula (1):

[0010]

[0011] In formula (1),

[0012] The L1 is one of a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group;

[0013] The L2 is one of a substituted or unsubstituted C6-C60 arylene group and a substituted or unsubstituted C3-C60 heteroarylene group;

[0014] X is one of S, O, CR5R6, NR7, and SiR8R9;

[0015] The Y is S, O, CR 10 R 11 NR 12 、SiR 13 R 14 One of;

[0016] Ar1 is one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group;

[0017] The R1, R2, R3, and R4 are independently one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 arylamino, and substituted or unsubstituted C3-C60 heteroarylamino. The above R1, R2, R3, and R4 can be independently fused with the aromatic ring or heteroaromatic ring to which they are connected; when there are multiple substituents, these substituents can be connected to each other by chemical bonds to form a ring. For example, when there are multiple R1-R4 substituents, these R1-R4 can form a ring by chemical bonds.

[0018] R5, R6, R8, R9, R 10 , R 11 , R 13 , R 14 are independently selected from a substituted or unsubstituted C1-C30 chain alkyl, a substituted or unsubstituted C3-C30 cycloalkyl, a substituted or unsubstituted C1-C30 alkoxy, a substituted or unsubstituted C6-C60 aryl, or a substituted or unsubstituted C3-C60 heteroaryl; between R5 and R6, between R8 and R9, and R 10 and R 11 Between 13 and R 14 They can be independently connected to each other through chemical bonds to form a ring;

[0019] The R7 and R 12 Each is independently selected from a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group.

[0020] The m, n, p, and q are independently selected from 1 to the maximum possible integer value, i.e., the upper limit of each substitutable position; when m, n, p, and q are independently integer values ​​greater than 1, multiple R1s, multiple R2s, multiple R3s, and multiple R4s can be independently connected to each other through chemical bonds to form a ring, and multiple R1s, multiple R2s, multiple R3s, and multiple R4s are each the same or different groups;

[0021] When the above-mentioned substituted or unsubstituted groups have a substituent, the substituent is selected from one or a combination of at least two of hydrogen, halogen, cyano, nitro, hydroxyl, carboxyl, aldehyde, carbonyl, amino, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C30 alkoxy, C1-C30 silyl, C6-C60 aryloxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl.

[0022] Furthermore, the organic compound of the present invention has a structure as shown in formula (2):

[0023]

[0024] In formula (2), the definitions of L1, L2, X, Y, Ar1, R1, R2, R3, m, n, and p are the same as those in formula (1).

[0025] Furthermore, the organic compound of the present invention has a structure as shown in any one of formula (2-1), (2-2) or (2-3):

[0026]

[0027] In formula (2-1), formula (2-2) and formula (2-3), the definitions of L1, L2, X, Ar1, R1, R2, R3, m, n and p are the same as those in formula (1).

[0028] Furthermore, the organic compound of the present invention has a structure as shown in any one of formula (3-1), (3-2), (3-3) or (3-4):

[0029]

[0030] In formulas (3-1), (3-2), (3-3) and (3-4), the definitions of L1, L2, X, Y, Ar1, R1, R2, R3, R4, m, n, p and q are the same as those in formula (1).

[0031] Preferably, the organic compound of the present invention has a structure as shown in formula (3-2) or (3-3).

[0032] More preferably, the organic compound of the present invention has a structure as shown in formula (3-2), wherein X is CR5R6;

[0033] More preferably, the organic compound of the present invention has a structure as shown in formula (3-3), wherein X is S or O.

[0034] Furthermore, in the organic compounds of formula (1), (2), (3-1), (3-2), (3-3) and (3-4) of the present invention, Y is S, O, CR 10 R 11 or NR 12 ;

[0035] More preferably, Y is S, O, CR 10 R 11 One of;

[0036] More preferably, the R 10 , R 11 , R 12 Each is independently selected from a substituted or unsubstituted C1-C12 chain alkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group.

[0037] Furthermore, in the organic compounds of formula (1), formula (2), formula (3-1), formula (3-2), formula (3-3), and formula (3-4) of the present invention, X is one of S, O, CR5R6, and NR7;

[0038] More preferably, X is one of S, O, and CR5R6;

[0039] More preferably, R5, R6, and R7 are independently selected from a substituted or unsubstituted C1-C12 chain alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group.

[0040] Furthermore, in the organic compounds of formula (1), formula (2), formula (3-1), formula (3-2), formula (3-3) and formula (3-4) of the present invention, L1 is a single bond.

[0041] Furthermore, in the organic compounds of formula (1), (2), (2-1), (2-2), (2-3), (3-1), (3-2), (3-3) and (3-4) of the present invention, L2 is a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C3-C30 heteroarylene group; preferably, L2 is a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C3-C20 heteroarylene group; more preferably, L2 is a substituted or unsubstituted sub-group of the following sub-groups: phenylene, biphenylene or naphthylene; most preferably, L2 is a substituted or unsubstituted phenylene group.

[0042] Most preferably, L2 is a substituted or unsubstituted structure:

[0043]

[0044] When the above-mentioned substituted or unsubstituted groups have a substituent, the substituent is selected from one or a combination of at least two of hydrogen, halogen, cyano, nitro, hydroxyl, carboxyl, aldehyde, carbonyl, amino, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C30 alkoxy, C1-C30 silyl, C6-C60 aryloxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl.

[0045] Furthermore, in the organic compounds of formula (1), (2), (2-1), (2-2), (2-3), (3-1), (3-2), (3-3) and (3-4) of the present invention, Ar1 is a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group; preferably, Ar1 is a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C3-C20 heteroaryl group; more preferably, Ar1 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; most preferably, Ar1 is a substituted or unsubstituted phenyl group.

[0046] When the above-mentioned substituted or unsubstituted groups have a substituent, the substituent is selected from hydrogen, halogen, cyano, nitro, hydroxyl, carboxyl, aldehyde, carbonyl, amino, C1-C30 alkyl, C1-C30 alkoxy, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, or a combination of at least two of them.

[0047] Furthermore, in the organic compounds of formula (1), formula (2), formula (2-1), formula (2-2), formula (2-3), formula (3-1), formula (3-2), formula (3-3), and formula (3-4) of the present invention, R1 is hydrogen or phenyl; preferably, R1 is hydrogen;

[0048] The R2 is one of hydrogen, C1-C20 straight chain alkyl, C1-C20 branched chain alkyl or phenyl; preferably, R2 is hydrogen, C1-C10 straight chain alkyl or C1-C10 branched chain alkyl;

[0049] The R 3 For hydrogen.

[0050] In this type of organic compounds of the present invention, R2 in the general formula is most preferably an alkyl group. This is because the alkyl group has good electron donation ability and can increase the blocking ability for excitons, thereby ensuring that the compounds of the present invention have excellent performance when used as hole transport layer and electron blocking layer materials.

[0051] In this type of organic compound of the present invention, L2 in the general formula is preferably designed to be selected from arylene groups, more preferably phenylene groups, biphenylene groups or naphthylene groups, and Ar1 is preferably designed to be selected from aryl groups, more preferably phenyl groups or biphenylene groups, which can make the steric hindrance of the molecules of the compound of the present invention more appropriate, improve the hole transport ability of the molecules, thereby improving the charge transport and stability of the molecules, and prevent the organic electroluminescent device using the compounds of the present invention from experiencing efficiency roll-off problems.

[0052] The inventors have found that if the above-mentioned condensed aromatic ring or condensed heterocyclic structure is directly connected to the nitrogen atom (i.e., L2 is a single bond), even if all other conditions are met, the performance of the obtained material is reduced compared with the above-mentioned compounds of the present invention. In other words, condensed aromatic rings or condensed heterocyclic structures such as 9,9-dimethylfluorene, dibenzofuran, and dibenzothiophene must be bridged to the nitrogen atom through an aromatic group of a certain size. In addition to increasing the conjugation ability of the above-mentioned condensed aromatic ring or condensed heterocyclic structure by bridging with the aromatic group to improve the transmission efficiency, there may also be steric hindrance reasons. Specifically, because the benzene ring directly connected to the N atom on the parent nucleus needs to be connected to an aromatic group Ar1 with a certain steric hindrance at the ortho position of N, if the condensed aromatic ring or condensed heterocyclic structure is directly connected to the nitrogen atom, the steric hindrance between it and Ar1 may be too large. Therefore, it is necessary to simultaneously satisfy the two conditions that L2 is a subaromatic group as defined in the present invention and Ar1 is an aromatic group as defined in the present invention. The α position of naphthalene is replaced by a condensed aromatic ring, which further enhances the conjugation ability of the molecule. Based on their synergistic effect, the compound molecule of the present invention has excellent transmission efficiency and the size of steric hindrance is within an appropriate range.

[0053] It should be noted that, for the sake of convenience, the possible effects of each group / feature are described separately in this application, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between the various groups, rather than the effect of a single group.

[0054] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expressions are involved in the present invention, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0055] In the present specification, the expression of Ca to Cb represents that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in the substituent.

[0056] In the present specification, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0057] In the present specification, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0058] In the present invention, the expression of chemical elements, unless otherwise specified, generally includes the concept of isotopes thereof. For example, the expression "hydrogen (H)" includes its isotopes. 1 H (hydrogen or H), 2 The concept of H (deuterium or D); carbon (C) includes 12 C. 13 C, etc., no further details.

[0059] The heteroatom in the present invention generally refers to an atom or an atom group selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0060] In the present specification, examples of halogen include fluorine, chlorine, bromine, and iodine.

[0061] In the present invention, the substituted or unsubstituted C6-C60 aryl includes a monocyclic aryl and a condensed aryl, preferably a C6-C30 aryl, and more preferably a C6-C20 aryl. The so-called monocyclic aryl refers to a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as phenyl, biphenyl, terphenyl, etc. Specifically, the biphenyl includes 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. Condensed aryl refers to a molecule containing at least two aromatic rings, and the aromatic rings are not independent of each other but share two adjacent carbon atoms to condense each other. For example, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl, fluoranthenyl, triphenylene, pyrenyl, peryl, The naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthacenyl group is selected from 1-naphthacenyl, 2-naphthacenyl and 9-naphthacenyl. The fluorene derivative group is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirobifluorene and benzofluorenyl.

[0062] The C3-C60 heteroaryl mentioned in the present invention includes monocyclic heteroaryl and condensed ring heteroaryl, preferably C3-C30 heteroaryl, more preferably C4-C20 heteroaryl, and more preferably C5-C12 heteroaryl. Monocyclic heteroaryl refers to a molecule containing at least one heteroaryl. When the molecule contains one heteroaryl and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl include furanyl, thienyl, pyrrolyl, pyridyl, etc. Condensed ring heteroaryl refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but share two adjacent atoms and are fused to each other. Examples of fused ring heteroaryl groups include benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl and the like.

[0063] Specific examples of the arylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned aryl groups. Specific examples of the heteroarylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned heteroaryl groups.

[0064] The aryloxy group in the present invention includes a monovalent group composed of the above-mentioned aryl group and heteroaryl group and oxygen.

[0065] Examples of the C6-C30 arylamino group mentioned in the present invention include phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, and biphenylamino.

[0066] Examples of the C3-C30 heteroarylamino group mentioned in the present invention include pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.

[0067] The chain alkyl mentioned in the present invention, unless otherwise specified, includes straight chain alkyl and branched chain alkyl. Specifically, the substituted or unsubstituted C1-C30 chain alkyl is preferably a substituted or unsubstituted C1-C16 chain alkyl, and more preferably a substituted or unsubstituted C1-C10 chain alkyl. The substituted or unsubstituted C1-C10 chain alkyl includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.

[0068] In the present invention, the C3-C20 cycloalkyl group is preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0069] The substituted or unsubstituted C6-C30 aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and derivatives thereof, fluoranthenyl, triphenylene, pyrenyl, peryl, A combination of one or more groups consisting of a 1-anthracenyl group and a naphthyl group. Specifically, the biphenyl group includes 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl and 9-fluorenyl. The derivative group of fluorene is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirofluorenyl and benzofluorenyl; the pyrenyl is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthyl is selected from 1-naphthyl, 2-naphthyl and 9-naphthyl.

[0070] The above-mentioned substituted or unsubstituted C3-C30 heteroaryl group is preferably a furyl group, a thienyl group, a pyrrolyl group, a benzofuranyl group, a benzothienyl group, an isobenzofuranyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an acridinyl group, an isobenzofuranyl group, an isobenzothienyl group, an acridinyl group, a pyridyl group, a benzocarbazolyl group, an azacarbazolyl group, a phenothiazinyl group, or a phenazinyl group, or a combination of two or more of the group.

[0071] Furthermore, the general formula compound of the present invention is preferably the following specific compound, but the present invention is not limited to the specific compounds shown below:

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089] As another aspect of the present invention, there is also provided an application of the compound as described above in an organic electroluminescent device. Specifically, it is preferably used as a light-emitting layer material in an organic electroluminescent device, and more preferably as a hole transport layer material or an electron blocking layer material in an organic electroluminescent device.

[0090] In addition to organic electroluminescent devices, the compound of the present invention can be applied to lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners or electronic papers.

[0091] As another aspect of the present invention, an organic electroluminescent device is provided, comprising a first electrode, a second electrode and an organic layer inserted between the first electrode and the second electrode, characterized in that the organic layer contains a compound represented by formula (1) as described above, or contains a compound having a structure represented by at least one of C1 to C353 as described above.

[0092] Specifically, an embodiment of the present invention provides an organic electroluminescent device, comprising a substrate, and a first electrode, a plurality of light-emitting functional layers and a second electrode sequentially formed on the substrate; the light-emitting functional layers comprise a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is between the hole transport layer and the electron transport layer; wherein the organic layer contains a compound of the general formula (1) as described above, or contains a compound of the structure shown in at least one of C1 to C348 as shown above.

[0093] The present invention further discloses a display screen or a display panel, wherein the organic electroluminescent device as described above is adopted in the display screen or the display panel; preferably, the display screen or the display panel is an OLED display.

[0094] The present invention also discloses an electronic device, wherein the electronic device has a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device as described above.

[0095] In the above-mentioned compound of the present invention, the core structure is a naphthylamine mother core obtained by replacing the α position of the naphthyl with a condensed aromatic ring. By adopting the combination of such a condensed aromatic ring with good conjugation ability and the naphthyl, it is beneficial to improve the charge mobility of the compound molecule. At the same time, by introducing condensed aromatic rings or condensed heterocyclic structures such as 9,9-dimethylfluorene, dibenzofuran, dibenzothiophene, etc. through bridging of other aromatic groups in the mother core, it can be ensured that the compound molecule has a good conjugated planar structure and thermal stability, and the bridging with the aromatic group increases the conjugation ability of such molecules, improves the hole transport ability of the molecules, and thus improves the molecular charge transport and molecular stability.

[0096] On the other hand, the introduction of a group at the ortho position of the aniline group increases the triplet energy level of the molecule, and the high triplet energy level can inhibit the loss of excitons in the light-emitting layer, prevent the problem of charge imbalance in the light-emitting layer caused by the transfer of excitons to the hole transport layer, and thus prevent the efficiency of the device from rolling off. At the same time, since the ortho-substitution has a certain steric hindrance, it can prevent the molecule from being overly planarized and forming crystals at high temperatures.

[0097] When such organic compounds prepared by the molecular structure design and group combination design of the present invention are used as hole transport layer materials or electron blocking layer materials of organic electroluminescent devices, the devices can obtain lower starting voltage, higher luminous efficiency and longer service life. The reasons for their excellent performance are not clear, but are speculated as follows:

[0098] In the structure of this type of organic compound of the present invention, by introducing condensed aromatic hydrocarbons into the naphthyl group and bridging the dibenzofuran group, dibenzothiophene group and fluorene group through aromatic groups, the conjugated delocalization range of π electrons is increased, thereby improving the charge transfer ability of the molecule, which is conducive to reducing the voltage; secondly, the ortho-substitution has a certain steric hindrance, which can improve the crystallization tendency of the molecule at high temperature, avoid the formation of a crystalline state during evaporation, thereby causing local accumulation of heat, leading to device degradation, structural distortion caused by steric hindrance, and can also increase the triplet energy level of the molecule, thereby blocking the excitons generated in the light-emitting layer from migrating to the hole transport layer, and the utilization rate of the excitons is improved, thereby improving the efficiency. The OLED device prepared using the compound of the present invention can meet the requirements of current panel manufacturers for high-performance materials. DETAILED DESCRIPTION

[0099] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0100] In the present invention, the synthesis method of the above-mentioned compound is briefly described, and the representative synthesis route of the compound of formula 1 is as follows:

[0101]

[0102] The solvents and reagents used in the following synthesis examples in the present invention, such as aryl bromide, 4-bromobiphenyl, tris(dibenzylideneacetone)dipalladium, toluene, methanol, dichloromethane, acetone, ethyl acetate, ethanol, tri-tert-butylphosphine, 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride and other chemical reagents, can be purchased or customized from the domestic chemical product market, such as purchased from Sinopharm Group Reagent Company, Sigma-Aldrich Company, and J&K Reagent Company, and the compounds or intermediates involved in the experiment can be customized by the reagent company. In addition, those skilled in the art can also synthesize by known methods.

[0103] The mass spectrometry data in the following synthesis examples were obtained by testing with a ZAB-HS mass spectrometer manufactured by Micromass, UK.

[0104] Synthesis Example 1: Synthesis of Compound C1

[0105]

[0106] In a 250mL single-mouth bottle, add 15.0g (67.6mmol) 1-bromo-2-aminonaphthalene, 18.8g (81.1mmol) o-bromobiphenyl, 0.786g (0.680mmol) tetrakis (triphenylphosphine) palladium (i.e. Pd (PPh3) 4), 250mL toluene, 14.0g (101.4mmol) potassium carbonate (K2CO3), vacuum and replace nitrogen 3 times, and heat the reaction to 80°C for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1h, and filter to obtain 18g of light yellow powder M1-1, M / Z measured value: 310 (M+H).

[0107] In a 250mL single-mouth bottle, add 10.0g (32.4mmol) M1-1, 8.30g (35.6mmol) 2-(4-bromophenyl) dibenzofuran, 0.30g (0.324mmol) tris (dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.266g (0.648mmol) 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (i.e. SPhOS), 150mL toluene, 4.7g (48.6mmol) sodium tert-butoxide (NaOBu-t), evacuate and replace with nitrogen 3 times, and heat the reaction to 80°C for 4h. After the reaction is complete, stop the reaction. After cooling to room temperature, the reaction solution was passed through a short silica gel column and washed with toluene until no product was found. The toluene was concentrated to obtain a yellow oil. Methanol was added and stirred to slowly precipitate a solid. 11.5 g of light yellow powder M1-2 was obtained by suction filtration. The measured M / Z value was 462 (M+H).

[0108] In a 250mL three-necked flask, add 10.0g (21.7mmol) M1-2, 8.4g (26.0mmol) 4-(dibenzofuran-2-) bromobenzene, 0.20g (0.217mmol) tri(dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.3mL tri-tert-butylphosphine xylene solution, 3.2g (32.6mmol) sodium tert-butoxide (NaOBu-t), 150mL toluene (Toluene), evacuate and replace nitrogen 3 times, and heat the reaction to 100℃ for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized in toluene and ethanol, and filtered to obtain 10.2g of light yellow powder C1, M / Z measured value: 704 (M+H)

[0109] Synthesis Example 2: Compound C4

[0110]

[0111] In a 250mL three-necked flask, add 8.0g (17.4mmol) M1-2, 6.7g (20.8mmol) 4-(dibenzofuran-4-) bromobenzene, 0.20g (0.217mmol) tri(dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.3mL tri-tert-butylphosphine xylene solution, 2.6g (26.1mmol) sodium tert-butoxide (NaOBu-t), 110mL toluene (Toluene) in sequence, evacuate and replace with nitrogen 3 times, and heat the reaction to 100°C for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized in toluene and ethanol, and filtered to obtain 9.3g of light yellow powder C4, M / Z measured value: 704 (M+H)

[0112] Synthesis Example 3: Compound C23

[0113]

[0114] In a 250mL three-necked flask, add 10.0g (21.7mmol) M1-2, 9.67g (26.0mmol) sub-3, 0.20g (0.217mmol) tri(dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.3mL tri-tert-butylphosphine xylene solution, 3.25g (32.6mmol) sodium tert-butoxide (NaOBu-t), 110mL toluene (Toluene) in sequence, evacuate and replace with nitrogen 3 times, and heat the reaction to 100°C for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized in toluene and ethanol, and filtered to obtain 9.0g of light yellow powder C23, M / Z measured value: 754 (M+H)

[0115] Synthesis Example 4: Synthesis of Compound C61

[0116]

[0117] In a 250mL three-necked flask, add 10.0g (21.7mmol) M1-2, 8.79g (26.0mmol) sub-4, 0.20g (0.217mmol) tri(dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.3mL tri-tert-butylphosphine xylene solution, 3.25g (32.6mmol) sodium tert-butoxide (NaOBu-t), 110mL toluene (Toluene) in sequence, evacuate and replace with nitrogen 3 times, and heat the reaction to 100°C for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized in toluene and ethanol, and filtered to obtain 11.5g of light yellow powder C61, M / Z measured value: 720 (M+H)

[0118] Synthesis Example 5: Synthesis of Compound C76

[0119]

[0120] In a 250mL three-necked flask, add 10.0g (21.7mmol) M1-2, 10.0g (26.0mmol) sub-5, 0.20g (0.217mmol) tri(dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.3mL tri-tert-butylphosphine xylene solution, 3.25g (32.6mmol) sodium tert-butoxide (NaOBu-t), 110mL toluene (Toluene) in sequence, evacuate and replace with nitrogen 3 times, and heat the reaction to 100℃ for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized in toluene and ethanol, and filtered to obtain 13.0g of light yellow powder C76, M / Z measured value: 720 (M+H)

[0121] Synthesis Example 6: Synthesis of Compound C101

[0122]

[0123] In a 250mL single-mouth bottle, add 15.0g (67.6mmol) 1-bromo-2-aminonaphthalene, 18.5g (81.1mmol) dibenzothiophene-4-boric acid, 0.786g (0.680mmol) tetrakis (triphenylphosphine) palladium (i.e. Pd (PPh3) 4), 250mL toluene, 14.0g (101.4mmol) potassium carbonate (K2CO3), vacuum and replace nitrogen 3 times, and heat the reaction to 80°C for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1h, and filter to obtain 18g of light yellow powder M2-1, M / Z measured value: 326 (M+H).

[0124] In a 250mL single-mouth bottle, add 10.0g (30.8mmol) M2-1, 7.86g (33.9mmol) o-bromobiphenyl, 0.30g (0.324mmol) tris (dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.266g (0.648mmol) 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (i.e. SPhOS), 150mL toluene, 4.7g (48.6mmol) sodium tert-butoxide (NaOBu-t), vacuum and replace nitrogen 3 times, and heat the reaction to 80°C for 4h. After the reaction is complete, stop the reaction. After cooling to room temperature, the reaction solution was passed through a short silica gel column and washed with toluene until no product was found. The toluene was concentrated to obtain a yellow oil. Methanol was added and stirred to slowly precipitate a solid. 10.0 g of light yellow powder M2-2 was obtained by suction filtration. The measured M / Z value was 478 (M+H).

[0125] In a 250mL three-necked flask, add 10.0g (21.0mmol) M2-2, 10.4g (25.2mol) sub-6, 0.18g (0.20mmol) tri(dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.3mL tri-tert-butylphosphine xylene solution, 2.6g (27.3mmol) sodium tert-butoxide (NaOBu-t), 150mL toluene (Toluene) in sequence, evacuate and replace with nitrogen 3 times, and heat the reaction to 100°C for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized in toluene and ethanol, and filtered to obtain 13.5g of light yellow powder C101, M / Z measured value: 812 (M+H)

[0126] Synthesis Example 7: Synthesis of Compound C117

[0127]

[0128] In a 250mL single-mouth bottle, add 15.0g (67.6mmol) 1-bromo-2-aminonaphthalene, 19.3g (81.1mmol) 9,9-dimethylfluorene-1-boric acid, 0.786g (0.680mmol) tetrakis (triphenylphosphine) palladium (i.e. Pd (PPh3) 4), 250mL toluene, 14.0g (101.4mmol) potassium carbonate (K2CO3), vacuumize and replace nitrogen 3 times, and heat the reaction to 80°C for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1h, and filter to obtain 15g of light yellow powder M3-1, M / Z measured value: 336 (M+H).

[0129] In a 250mL single-mouth bottle, add 10.0g (29.9mmol) M3-1, 7.28g (31.4mmol) o-bromobiphenyl, 0.30g (0.324mmol) tris (dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.266g (0.648mmol) 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (i.e. SPhOS), 150mL toluene, 4.7g (48.6mmol) sodium tert-butoxide (NaOBu-t), vacuum and replace nitrogen 3 times, and heat the reaction to 80℃ for 4h. After the reaction is complete, stop the reaction. After cooling to room temperature, the reaction solution was passed through a short silica gel column and washed with toluene until no product was found. The toluene was concentrated to obtain a yellow oil. Methanol was added and stirred to slowly precipitate a solid. 8.5 g of light yellow powder M3-2 was obtained by suction filtration. The measured M / Z value was 488 (M+H).

[0130] In a 250mL three-necked flask, add 10.0g (20.5mmol) M3-2, 8.33g (24.6mol) sub-4, 0.18g (0.20mmol) tri(dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.3mL tri-tert-butylphosphine xylene solution, 2.6g (27.3mmol) sodium tert-butoxide (NaOBu-t), 150mL toluene (Toluene), evacuate and replace with nitrogen 3 times, and heat the reaction to 100℃ for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized in toluene and ethanol, and filtered to obtain 11g of light yellow powder C117, M / Z measured value: 746 (M+H)

[0131] Synthesis Example 8: Synthesis of Compound C123

[0132]

[0133] In a 250mL single-mouth bottle, add 15.0g (67.6mmol) 1-bromo-2-aminonaphthalene, 15.8g (74.7mmol) dibenzofuran-3-boric acid, 0.786g (0.680mmol) tetrakis (triphenylphosphine) palladium (i.e. Pd (PPh3) 4), 250mL toluene, 14.0g (101.4mmol) potassium carbonate (K2CO3), vacuum and replace nitrogen 3 times, and heat the reaction to 80°C for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1h, and filter to obtain 16g of light yellow powder M4-1, M / Z measured value: 310 (M+H).

[0134] In a 250mL single-mouth bottle, add 12.0g (38.8mmol) M4-1, 9.90g (42.7mmol) o-bromobiphenyl, 0.36g (0.388mmol) tris(dibenzylideneacetone)dipalladium (i.e. Pd2(dba)3), 0.27g (0.648mmol) 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (i.e. SPhOS), 150mL toluene, 4.9g (50.4mmol) sodium tert-butoxide (NaOBu-t), vacuum and replace nitrogen 3 times, and heat the reaction to 80℃ for 4h. After the reaction is complete, stop the reaction. After cooling to room temperature, the reaction solution was passed through a short silica gel column and washed with toluene until no product was found. The toluene was concentrated to obtain a yellow oil. Methanol was added and stirred to slowly precipitate a solid. 14 g of light yellow powder M4-2 was obtained by suction filtration. The measured M / Z value was 462 (M+H).

[0135] In a 250mL three-necked flask, add 14.0g (30.4mmol) M4-2, 12.7g (36.4mol) sub-8, 0.28g (0.30mmol) tri(dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.4mL tri-tert-butylphosphine xylene solution, 4.4g (45.6mmol) sodium tert-butoxide (NaOBu-t), 150mL toluene (Toluene) in sequence, evacuate and replace with nitrogen 3 times, and heat the reaction to 100℃ for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized to obtain 18g of light yellow powder C123, M / Z measured value: 730 (M+H)

[0136] Synthesis Example 9: Synthesis of Compound C142

[0137]

[0138] In a 250mL single-mouth bottle, add 15.0g (67.6mmol) 1-bromo-2-aminonaphthalene, 16.1g (74.7mmol) 9,9-dimethylfluorene-1-boric acid, 0.786g (0.680mmol) tetrakis (triphenylphosphine) palladium (i.e. Pd (PPh3) 4), 250mL toluene, 14.0g (101.4mmol) potassium carbonate (K2CO3), vacuum and replace nitrogen 3 times, and heat the reaction to 80°C for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1h, and filter to obtain 15g of light yellow powder M5-1, M / Z measured value: 336 (M+H).

[0139] In a 250mL single-mouth bottle, add 15.0g (44.8mmol) M5-1, 14.2g (49.3mmol) 2-bromo-4'-tert-butyl-1,1'-biphenyl, 0.41 (0.448mmol) tris(dibenzylideneacetone)dipalladium (i.e. Pd2(dba)3), 0.37g (0.896mmol) 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (i.e. SPhOS), 180mL toluene (Toluene), 5.6g (58.2mmol) sodium tert-butoxide (NaOBu-t), evacuate and replace with nitrogen 3 times, and heat the reaction to 80°C for 4h. After the reaction is complete, stop the reaction. After cooling to room temperature, the reaction solution was passed through a short silica gel column and washed with toluene until no product was found. The toluene was concentrated to obtain a yellow oil. Methanol was added and stirred to slowly precipitate a solid. 20 g of light yellow powder M5-2 was obtained by suction filtration. The measured M / Z value was 544 (M+H).

[0140] In a 250mL three-necked flask, add 10.0g (18.4mmol) M5-2, 7.68g (22.1mol) sub-8, 0.17g (0.18mmol) tri(dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.3mL tri-tert-butylphosphine xylene solution, 2.6g (27.6mmol) sodium tert-butoxide (NaOBu-t), 120mL toluene (Toluene) in sequence, evacuate and replace with nitrogen 3 times, and heat the reaction to 100°C for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized to obtain 10g of light yellow powder C142, M / Z measured value: 812 (M+H)

[0141] Synthesis Example 9: Synthesis of Compound 160

[0142]

[0143] In a 250mL single-mouth bottle, add 15.0g (67.6mmol) 1-bromo-2-aminonaphthalene, 16.1g (74.7mmol) 9,9-dimethylfluorene-2-boric acid, 0.786g (0.680mmol) tetrakis (triphenylphosphine) palladium (i.e. Pd (PPh3) 4), 250mL toluene, 14.0g (101.4mmol) potassium carbonate (K2CO3), vacuum and replace nitrogen 3 times, and heat the reaction to 80℃ for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1h, and filter to obtain 17g of light yellow powder M6-1, M / Z measured value: 336 (M+H).

[0144] In a 250mL single-mouth bottle, add 10.0g (29.8mmol) M6-1, 9.7g (29.8mmol) 4-tert-butyl-2-phenylbromobenzene, 0.27 (0.30mmol) tris(dibenzylideneacetone)dipalladium (i.e. Pd2(dba)3), 0.25g (0.60mmol) 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (i.e. SPhOS), 130mL toluene, 4.3g (44.7mmol) sodium tert-butoxide (NaOBu-t), vacuum and replace nitrogen 3 times, and heat the reaction to 80°C for 4h. After the reaction is complete, stop the reaction. After cooling to room temperature, the reaction solution was passed through a short silica gel column and washed with toluene until no product was found. The toluene was concentrated to obtain a yellow oil. Methanol was added and stirred to slowly precipitate a solid. 12 g of light yellow powder M6-2 was obtained by suction filtration. The measured M / Z value was 544 (M+H).

[0145] In a 250mL three-necked flask, add 10.0g (18.4mmol) M6-2, 7.12g (22.1mol) sub-9, 0.17g (0.18mmol) tri(dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.3mL tri-tert-butylphosphine xylene solution, 2.6g (27.6mmol) sodium tert-butoxide (NaOBu-t), 130mL toluene (Toluene) in sequence, evacuate and replace with nitrogen 3 times, and heat the reaction to 100℃ for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized to obtain 9g of light yellow powder C160, M / Z measured value: 786 (M+H)

[0146] Synthesis Example 10: Synthesis of Compound 325

[0147]

[0148] In a 250mL three-necked flask, add 12.0g (26.0mmol) M1-1, 12.4g (31.2mol) sub-10, 0.24g (0.26mmol) tri(dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.3mL tri-tert-butylphosphine xylene solution, 3.7g (39.0mmol) sodium tert-butoxide (NaOBu-t), 150mL toluene (Toluene) in sequence, evacuate and replace with nitrogen 3 times, and heat the reaction to 100℃ for 6h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate the toluene to obtain a brown solid. The solid is recrystallized to obtain 14g of light yellow powder C325, M / Z measured value: 779 (M+H)

[0149] Synthesis Example 11: Synthesis of Compound C227

[0150]

[0151] In a 250mL single-mouth bottle, add 15.0g (67.6mmol) 1-bromo-2-aminonaphthalene, 16.1g (74.7mmol) 9,9-dimethylfluorene-3-boric acid, 0.786g (0.680mmol) tetrakis (triphenylphosphine) palladium (i.e. Pd (PPh3) 4), 250mL toluene, 14.0g (101.4mmol) potassium carbonate (K2CO3), vacuumize and replace nitrogen 3 times, and heat the reaction to 80°C for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, add methanol and stir for 1h, and filter to obtain 15g of light yellow powder M6-1, M / Z measured value: 336 (M+H).

[0152] In a 250mL single-mouth bottle, add 10.0g (29.8mmol) M7-1, 9.2g (29.8mmol) 2,4-diphenylbromobenzene, 0.27 (0.30mmol) tris (dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.25g (0.60mmol) 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (i.e. SPhOS), 130mL toluene (Toluene), 4.3g (44.7mmol) sodium tert-butoxide (NaOBu-t), vacuum and replace nitrogen 3 times, and heat the reaction to 80°C for 4h. After the reaction is complete, stop the reaction. After cooling to room temperature, the reaction solution was passed through a short silica gel column and washed with toluene until no product was found. The toluene was concentrated to obtain a yellow oil. Methanol was added and stirred to slowly precipitate a solid. 10 g of light yellow powder M7-2 was obtained by suction filtration. The measured M / Z value was 564 (M+H).

[0153] In a 250mL three-necked flask, add 10.0g (17.8mmol) M7-2, 12.0g (21.3mol) sub-11, 0.17g (0.18mmol) tri(dibenzylideneacetone) dipalladium (i.e. Pd2(dba)3), 0.3mL tri-tert-butylphosphine xylene solution, 2.6g (27.6mmol) sodium tert-butoxide (NaOBu-t), 130mL toluene (Toluene) in sequence, evacuate and replace with nitrogen 3 times, and heat the reaction to 100°C for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized to obtain 12g of light yellow powder C227, M / Z measured value: 856 (M+H)

[0154] Device Embodiment

[0155] OLED includes a first electrode, a second electrode, and an organic material layer between the electrodes. The organic material can be divided into multiple regions. For example, the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.

[0156] In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) may also be provided on the substrate used as a display.

[0157] The first electrode can be formed by sputtering or depositing the material used as 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), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0158] The organic material layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic material layer can be organic small molecules, organic macromolecules and polymers, and combinations thereof.

[0159] The hole transport region is located between the anode and the light-emitting layer. The hole transport region 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 region can also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0160] The material of the hole transport region can be selected from, but not limited to, the compounds described in the present invention or phthalocyanine derivative groups such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, 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), aromatic amine derivative groups such as compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0161]

[0162]

[0163]

[0164] 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 use one or more compounds of HT-1 to HT-51 above, or one or more compounds of HI-1 to HI-3 below; or one or more compounds of HT-1 to HT-51 can be doped with one or more compounds of HI-1 to HI-3 below.

[0165]

[0166] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit light of different wavelength spectra, and may also include a host material (Host). The light-emitting layer may be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors may be arranged in a plane according to a pixel pattern, or may be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they may be separated from each other or may be 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.

[0167] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescent materials, etc. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0168] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0169]

[0170] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFD-1 to BFD-24 listed below.

[0171]

[0172]

[0173] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology, and the main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-85.

[0174]

[0175]

[0176]

[0177]

[0178] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of GPD-1 to GPD-47 listed below.

[0179]

[0180]

[0181] D stands for deuterium.

[0182] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.

[0183]

[0184] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of YPD-1 to YPD-11 listed below.

[0185]

[0186]

[0187] In one aspect of the present invention, the light-emitting layer adopts the technology of thermally activated delayed fluorescence luminescence. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of the above PH-1 to PH-85.

[0188] In one aspect of the present invention, the light-emitting layer adopts the technology of thermally activated delayed fluorescence luminescence. The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of TDE1-TDE37 listed below.

[0189]

[0190]

[0191] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described above; or a mixture of, but not limited to, one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

[0192] 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 also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0193] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0194]

[0195]

[0196]

[0197] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be, but not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0198] The device may further include an electron injection layer located between the electron transport layer and the cathode. Materials for the electron injection layer include, but are not limited to, one or more combinations of the following.

[0199] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg.

[0200] The preparation process of the organic electroluminescent device in this embodiment is as follows:

[0201] Example 1, the invented compound as hole transport material

[0202] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol, baked in a clean environment to completely remove the water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0203] Place the glass substrate with the anode in a vacuum chamber and evacuate to a vacuum of <1×10 -5 Pa, vacuum thermally evaporate 10nm of compound C1:HI-3 (97 / 3, w / w) mixture as hole injection layer, 60nm of compound C1 as hole transport layer, 5nm of compound HT-48 as electron blocking layer; 40nm of compound PH-34:RPD-10 (100:3, w / w) binary mixture as light emitting layer; 5nm of ET-23 as hole blocking layer, 25nm of compound ET-69:ET-57 (50 / 50, w / w) mixture as electron transport layer, 1nm of LiF as electron injection layer, and 150nm of metal aluminum as cathode on the above anode layer film in order. The total evaporation rate of all organic layers and LiF is controlled at 0.1nm / sec, and the evaporation rate of metal electrode is controlled at 1nm / sec.

[0204] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0205] At the same brightness, a digital source meter and a brightness meter were used to measure the driving voltage and current efficiency of the organic electroluminescent device prepared according to the above method. Specifically, the voltage was increased at a rate of 0.1 V per second, and the brightness of the organic electroluminescent device was measured when it reached 3000 cd / m 2 The voltage at this time is the driving voltage, and the current density at this time is measured at the same time; the ratio of brightness to current density is the current efficiency.

[0206] In Examples 2-18, Compound C1 in Example 1 was replaced by the compounds of the present invention listed in Table 1; in Comparative Examples 1-3, Compound C1 was replaced by the comparative compounds shown in Table 1, respectively.

[0207] Comparative Example compounds R-1 to R-3 are as follows:

[0208] R-1: The synthesis method of R-1 is as follows:

[0209]

[0210] In a 250mL single-mouth bottle, add 27.0g (0.1mol) 2-aminobinaphthyl, 32.2g (0.1mol) 2-(4-bromophenyl)dibenzofuran, 0.90g (0.001mol) tris(dibenzylideneacetone)dipalladium (i.e. Pd2(dba)3), 0.82g (0.002mmol) 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (i.e. SPhOS), 400mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumize and replace nitrogen 3 times, and heat the reaction to 80°C for 4h. After the reaction is complete, stop the reaction. After cooling to room temperature, the reaction solution was passed through a short silica gel column and washed with toluene until no product was found. The toluene was concentrated to obtain a yellow oil. Methanol was added and stirred to slowly precipitate a solid. 42 g of light yellow powder intermediate R-1-1 was obtained by suction filtration. The measured M / Z value was 512 (M+H).

[0211] In a 250mL three-necked flask, add 10.0g (19.6mmol) of intermediate R-1-1, 5.5g (23.5mmol) of o-bromobiphenyl, 0.20g (0.217mmol) of tri(dibenzylideneacetone)dipalladium (i.e. Pd2(dba)3), 0.3mL of tri-tert-butylphosphine dimethylbenzene solution, 2.8g (29.4mmol) of sodium tert-butoxide (NaOBu-t), 150mL of toluene (Toluene), evacuate and replace with nitrogen 3 times, and heat the reaction to 120℃ for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate the solid. The solid is recrystallized in toluene and ethanol, and filtered to obtain 8.2g of light yellow powder R-1, M / Z measured value: 664 (M+H).

[0212] R-2: The synthesis method of R-2 is as follows:

[0213]

[0214] In a 250mL single-mouth bottle, add 10.0g (29.8mmol) M2-1, 8.1g (29.8mmol) 2-bromo-9,9-dimethylfluorene, 0.27 (0.30mmol) tris(dibenzylideneacetone)dipalladium (i.e. Pd2(dba)3), 0.25g (0.60mmol) 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (i.e. SPhOS), 130mL toluene (Toluene), 4.3g (44.7mmol) sodium tert-butoxide (NaOBu-t), vacuum and replace nitrogen 3 times, and heat the reaction to 80°C for 8h. After the reaction is complete, stop the reaction. After cooling to room temperature, the reaction solution was passed through a short silica gel column and washed with toluene until no product was found. The toluene was concentrated to obtain a yellow oil. Petroleum ether was added and stirred to slowly precipitate a solid. 9.5 g of light yellow powder R-2-1 was obtained by suction filtration. The measured M / Z value was 528 (M+H).

[0215] In a 250mL three-necked flask, add 8.0g (15.2mmol) R-2-1, 6.1g (19.7mol) 2,4-diphenylbromobenzene, 0.14g (0.15mmol) tris (dibenzylideneacetone) palladium (i.e. Pd2 (dba) 3), 0.2mL tri-tert-butylphosphine dimethylbenzene solution, 2.2g (22.8mmol) sodium tert-butoxide (NaOBu-t), 100mL toluene (Toluene), vacuum and replace nitrogen 3 times, and heat the reaction to 100℃ for 4h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and elute toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized to obtain 5g white powder R-2, M / Z measured value: 690 (M+H).

[0216] R-3: The synthesis method of R-3 is as follows:

[0217]

[0218] In a 250mL single-mouth bottle, add 20g (64.7mmol) M3-1, 17.6g (64.7mmol) 2-bromo-9,9-dimethylfluorene, 0.60g (0.65mmol) tris(dibenzylideneacetone)dipalladium (i.e. Pd2(dba)3), 0.55g (1.30mmol) 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (i.e. SPhOS), 300mL toluene (Toluene), 7.5g (77.6mmol) sodium tert-butoxide (NaOBu-t), vacuumize and replace nitrogen 3 times, and heat the reaction to 80℃ for 8h. After the reaction is complete, stop the reaction. After cooling to room temperature, the reaction solution was passed through a short silica gel column and washed with toluene until no product was found. The toluene was concentrated to obtain a yellow oil. Methanol was added and stirred to slowly precipitate a solid. 22 g of light yellow powder R-3-1 was obtained by suction filtration. The measured M / Z value was 502 (M+H).

[0219] In a 250mL three-necked flask, add 10.0g (19.9mmol) R-3-1, 5.1g (21.9mol) 4-bromobiphenyl, 0.18g (0.20mmol) tri(dibenzylideneacetone)dipalladium (i.e. Pd2(dba)3), 0.2mL tri-tert-butylphosphine dimethylbenzene solution, 2.9g (29.9mmol) sodium tert-butoxide (NaOBu-t), 150mL toluene (Toluene), evacuate and replace nitrogen 3 times, and heat the reaction to 100℃ for 6h. After the reaction is complete, stop the reaction. Cool to room temperature, pass the reaction solution through a short silica gel column, and rinse with toluene until there is no product. Concentrate toluene to obtain a yellow oil, add methanol and stir, and slowly precipitate a solid. The solid is recrystallized to obtain 18g of light yellow powder R-3, M / Z measured value: 654 (M+H).

[0220] The properties of the organic electroluminescent devices prepared in the above Examples 1-18 and Comparative Examples 1-3 are shown in Table 1 below.

[0221] Table 1:

[0222] Example No. Hole transport layer materials <![CDATA[Brightness (cd / m 2 )]]> Voltage (V) Efficiency (cd / A) Comparative Example 1 R-1 3000 4.23 15.5 Comparative Example 2 R-2 3000 4.13 16.6 Comparative Example 3 R-3 3000 4.30 17.5 Example 1 C1 3000 3.97 19.2 Example 2 C2 3000 3.98 18.4 Example 3 C3 3000 3.95 18.7 Example 4 C4 3000 3.97 18.5 Example 5 C61 3000 4.05 19.5 Example 6 C117 3000 3.90 20.0 Example 7 C121 3000 3.88 19.3 Example 8 C123 3000 4.00 19.0 Example 9 C142 3000 3.80 21.1 Example 10 C160 3000 3.85 20.6 Embodiment 11 C181 3000 4.03 18.6 Example 12 C227 3000 3.95 19.3 Embodiment 13 C341 3000 3.92 19.6 Embodiment 14 C344 3000 4.02 18.5 Embodiment 15 C345 3000 4.06 17.8 Example 16 C346 3000 4.00 18.7 Embodiment 17 C347 3000 4.05 18.0 Embodiment 18 C348 3000 4.10 17.8

[0223] From the results in Table 1, it can be seen that when the compound described in the present invention is used as a hole transport material of a device, the current efficiency can reach above 17.0 cd / A, and the life span is greatly improved, and it is a hole transport material with good performance.

[0224] The only difference between the compound R-1 in comparative example 1 and the compound C1 in example 1 is that the substituent on the naphthalene in R-1 is α-naphthalene, while the substituent on the naphthalene in the compound C1 is dibenzofuran at the 4-position. From the performance data, the voltage of C1 is 0.26V lower than that of R-1, and the efficiency is 20% higher, both of which are better than R-1. This is because the dibenzofuranyl phenyl group has a better conjugated structure than the naphthyl group, which is conducive to improving the mobility of holes and making the charge transfer of the device more balanced, thereby obtaining a lower voltage and higher efficiency.

[0225] When the compounds of the present invention are used as electron blocking materials, Examples 19-24 replace C1 in the above preparation process with HT4 as the hole transport layer, and replace HT48 with the compounds of the present invention listed in Table 2 as the electron blocking layer; Comparative Examples 4-6 replace the HT-48 compound with the comparative compound shown in Table 2. The properties of the organic electroluminescent devices prepared in Examples 19-24 and Comparative Examples 4-6 are shown in Table 2 below.

[0226] Table 2:

[0227] Example No. Electron blocking layer materials <![CDATA[Brightness (cd / m 2 )]]> Voltage (V) Efficiency (cd / A) Comparative Example 4 R-1 3000 4.15 16.3 Comparative Example 5 R-2 3000 4.22 16.6 Comparative Example 6 R-3 3000 4.35 17.0 Embodiment 19 C1 3000 4.01 18.5 Embodiment 20 C4 3000 3.98 19.2 Embodiment 21 C23 3000 3.92 18.6 Embodiment 22 C76 3000 3.85 19.8 Embodiment 23 C101 3000 3.90 20.2 Embodiment 24 C325 3000 4.00 19.5

[0228] The only difference between the compound R-1 used in comparative example 4 and C1 in example 19 is that the substituent on naphthalene in R-1 is α-naphthalene, while the substituent on naphthalene in compound C1 is dibenzofuran at the 4-position. The device results show that when C1 is used as the electron blocking layer, the device performance is better than that of comparative example 4.

[0229] The compound of the present invention is formed by increasing the conjugated area of ​​the substituent on naphthalene, introducing a condensed aromatic ring or condensed heterocyclic structure with good conjugated planar structure and thermal stability through aromatic ring bridging, such as dibenzofuran, dibenzothiophene and fluorenyl, and introducing a specific aromatic group at the ortho position of anilino. Through specific structural combination, more excellent performance can be produced. When the present invention is used for organic electroluminescent device, current efficiency can be effectively improved and voltage can be reduced. As can be seen from this, the compound of the present invention is a hole transport material and an electron blocking material with good performance.

[0230] Although the present invention has been described in conjunction with the embodiments, the present invention is not limited to the above embodiments. It should be understood that under the guidance of the concept of the present invention, those skilled in the art may make various modifications and improvements. The appended claims summarize the scope of the present invention.

Claims

1. An organic compound having a structure as shown in formula (1): In formula (1): The L1 is a single bond; The L2 is one of a substituted or unsubstituted C6-C20 arylene group and a substituted or unsubstituted C3-C20 heteroarylene group; X is one of S, O, CR5R6, NR7, and SiR8R9; The Y is S, O, CR 10 R 11 NR 12 、SiR 13 R 14 One of; Ar1 is a substituted or unsubstituted C6-C60 aryl group; The R1, R2, and R3 are independently selected from hydrogen, a C1-C30 chain alkyl, a C6-C60 aryl, and a C3-C60 heteroaryl; R4 is hydrogen; and the R5, R6, R8, R9, and R 10 , R 11 , R 13 , R 14 Each is independently selected from one of a C1-C30 chain alkyl group, a C6-C60 aryl group, and a C3-C60 heteroaryl group; The R7 and R 12 Each is independently selected from one of a C6-C60 aryl group and a C3-C60 heteroaryl group; The m, n, p, and q are independently selected from 1; When the above-mentioned substituted or unsubstituted groups have a substituent, the substituent is selected from one of a C1-C30 chain alkyl group, a C6-C60 aryl group and a C3-C60 heteroaryl group.

2. The organic compound according to claim 1, having a structure as shown in formula (2): In formula (2), the definitions of L1, L2, X, Y, Ar1, R1, R2, R3, m, n, and p are the same as those in formula (1).

3. The organic compound according to claim 1, having a structure as shown in any one of formulas (2-1), (2-2) or (2-3): In formula (2-1), formula (2-2) and formula (2-3), the definitions of L1, L2, X, Ar1, R1, R2, R3, m, n and p are the same as those in formula (1).

4. The organic compound according to claim 1, having a structure as shown in any one of formulas (3-1), (3-2), (3-3) or (3-4): In formulas (3-1), (3-2), (3-3) and (3-4), the definitions of L1, L2, X, Y, Ar1, R1, R2, R3, R4, m, n, p and q are the same as those in formula (1).

5. The organic compound according to claim 4, having a structure as shown in formula (3-2) or (3-3).

6. The organic compound according to claim 4, having a structure as shown in formula (3-2), wherein X is CR5R6.

7. The organic compound according to claim 4, having a structure as shown in formula (3-3), wherein X is S or O.

8. The organic compound according to any one of claims 1, 2 or 4, wherein Y is S, O, CR 10 R 11 or NR 12 .

9. The organic compound according to any one of claims 1, 2 or 4, wherein Y is S, O, CR 10 R 11 One of them.

10. The organic compound according to any one of claims 1 to 4, wherein X is one of S, O, CR5R6, and NR7.

11. The organic compound according to any one of claims 1 to 4, wherein X is one of S, O, and CR5R6.

12. The organic compound according to claim 1, wherein L2 is a substituted or unsubstituted substituent group consisting of a phenylene group, a biphenylene group, or a naphthylene group.

13. The organic compound according to claim 1, wherein L2 is a substituted or unsubstituted phenylene group.

14. The organic compound according to claim 1, wherein L2 is one of the following substituted or unsubstituted structures: When the above-mentioned substituted or unsubstituted groups have a substituent, the substituent is selected from one of a C1-C30 chain alkyl group, a C6-C60 aryl group and a C3-C60 heteroaryl group. 15 . The organic compound according to claim 1 , wherein Ar 1 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group. The organic compound according to claim 1 , wherein Ar 1 is a substituted or unsubstituted phenyl group.

17. The organic compound according to claim 1, wherein R1 is hydrogen or phenyl; R2 is one of hydrogen, C1-C20 straight chain alkyl, C1-C20 branched chain alkyl or phenyl; The R 3 For hydrogen.

18. The organic compound according to claim 17, wherein R1 is hydrogen; and R2 is hydrogen, a C1-C10 straight-chain alkyl group, or a C1-C10 branched-chain alkyl group.

19. An organic compound having the structure shown below:

20. Use of the organic compound according to any one of claims 1 to 19, wherein the use is as a functional material in an organic electronic device, wherein the organic electronic device comprises an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper; The organic compound is used as a hole transport layer material or an electron blocking layer material in an organic electroluminescent device.

21. An organic electroluminescent device, comprising a first electrode, a second electrode and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains the compound according to any one of claims 1 to 19.

22. The organic electroluminescent device according to claim 21, wherein the light-emitting functional layer comprises a hole transport region, a light-emitting layer, and an electron transport region, wherein the hole transport region is formed on the first electrode layer, the second electrode layer is formed on the electron transport region, and the light-emitting layer is between the hole transport region and the electron transport region; wherein, The hole transport zone contains the compound according to any one of claims 1 to 19.

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