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

Abstract

The present invention relates to an organic compound, belonging to the technical field of organic light-emitting materials, and also relates to applications of the compound and an organic electroluminescent device containing the compound. The organic compound of the present invention has a structure as shown in formula (1). The organic compound of the present invention has excellent hole transport efficiency and injection capability. When the compound of the present invention is used in an organic electroluminescent device, the operating voltage of the device can be effectively reduced while improving the efficiency of the device.

Description

Technical Field

[0001] The invention relates to an organic compound, belonging to the technical field of organic luminescent 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, becoming a research hotspot in the field. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors (FETs), organic photovoltaic cells (OPTOs), and organic sensors. OLEDs have developed particularly rapidly, achieving commercial success in the information display field. OLEDs can produce highly saturated red, green, and blue colors, and full-color displays made from them require no additional backlight source, offering advantages such as vibrant colors, thinness, and flexibility.

[0003] The core of an OLED device is a multilayer thin-film structure containing a variety of organic functional materials. Common functional organic materials include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as luminescent host materials and luminescent guest materials (dyes). When power is applied, electrons and holes are injected and transported to the light-emitting region, where they recombine, 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 utilize 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 that of traditional fluorescent emitters. Thermally excited delayed fluorescence (TADF) technology promotes the conversion 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 device performance. On the one hand, hole transport materials need to have a suitable HOMO energy level and a suitable energy gap between the hole material and the anode to facilitate hole injection and help reduce the operating voltage. On the other hand, hole transport materials regulate the carrier transport balance within the device. Improving the carrier mobility of hole transport materials can improve luminous efficiency and delay device degradation. Although products using OLED display technology have been commercialized, there is still a demand for further improvement in device efficiency and service life. Therefore, this field urgently needs to develop more types of organic materials for application 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 demand for continuously improving optoelectronic performance of OLED devices and the demand for energy conservation in mobile electronic devices, it is necessary to develop new and efficient OLED materials. Among them, 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 an organic compound, which can be used as an organic thin layer material in an organic electroluminescent device, so that the device has lower voltage and higher luminous efficiency.

[0008] The present invention provides an organic compound having a structure as shown in formula (1):

[0009]

[0010] In formula (1),

[0011] The L1 and L2 are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group;

[0012] Said X is selected from S, O, SiR5R6 or CR7R8;

[0013] Ar1, Ar2, Ar3, and Ar4 are independently selected from a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group;

[0014] m and n are each independently 0 or 1, and m+n=1;

[0015] Said R1, R2, R3, and R4 are independently hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, ketone, ester, carbonyl substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C6 wherein the R1, R2, R3 and R4 are selected from the group consisting of a substituted or unsubstituted C3-C60 fused ring aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C3-C60 fused ring heteroaryl group, a substituted or unsubstituted C6-C60 arylamino group and a substituted or unsubstituted C3-C60 heteroarylamino group; the R1, R2, R3 and R4 can each independently be fused to the aromatic ring to which they are connected; when there are multiple substituents, these substituents can be linked to each other by chemical bonds to form a ring, for example, when there are multiple R1-R4 substituents, two adjacent ones of these R1-R4 can form a ring by chemical bonds.

[0016] R5, R6, R7, and R8 are independently selected from one of a substituted or unsubstituted C1-C30 chain alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a C3-C20 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; and R7 and R8 are not connected to each other by a chemical bond to form a ring;

[0017] The a, b, c, and d are independently selected from 1 to the maximum possible integer value, i.e., the upper limit of each substitutable position, and multiple R1, multiple R2, multiple R3, and multiple R4 are each the same or different groups; when a, b, c, and d are each independently an integer greater than 1, two adjacent groups in the multiple R1, multiple R2, multiple R3, or multiple R4 can be independently connected to each other by chemical bonds to form a ring;

[0018] 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, deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, ketone, ester, carbonyl, C1-C30 chain alkyl, C1-C30 alkoxy, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0019] 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 expression is involved in the present invention, it has the same meaning, and the selection range of the substituents is as shown above and will not be repeated one by one.

[0020] In this specification, the expression of Ca to Cb means that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms in the group generally does not include the number of carbon atoms in the substituent.

[0021] In this 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.

[0022] In this specification, “each independently” means that when there are multiple subjects, they may be the same or different.

[0023] In the present invention, the expression of chemical elements, unless otherwise specified, generally includes the concept of their isotopes. For example, the expression "hydrogen (H)" includes its isotopes. 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) includes 12 C. 13 C, etc., no further details.

[0024] The heteroatom in the heteroaryl group of 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.

[0025] In the present specification, examples of halogen include fluorine, chlorine, bromine, and iodine.

[0026] In the present invention, the substituted or unsubstituted C6-C60 aryl group includes a monocyclic aryl group and a condensed ring aryl group, preferably a C6-C30 aryl group, and more preferably a C6-C20 aryl group. The so-called monocyclic aryl group 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, for example, phenyl, biphenyl, terphenyl, etc. 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. A condensed ring aryl group refers to a molecule containing at least two aromatic rings, and the aromatic rings are not independent of each other but are fused to each other by sharing two adjacent carbon atoms. For example, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, 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 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, 9,9'-spirobifluorene and benzofluorenyl.

[0027] In the present invention, the substituted or unsubstituted C3 to C60 heteroaryl groups include monocyclic heteroaryl groups and fused ring heteroaryl groups, preferably C3-C30 heteroaryl groups, more preferably C4-C20 heteroaryl groups, and more preferably C5-C12 heteroaryl groups. A monocyclic heteroaryl group refers to a molecule containing at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl groups include furyl, thienyl, pyrrolyl, pyridyl, etc. A fused ring heteroaryl group 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 are fused to each other by sharing two adjacent atoms. 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, and indolocarbazolyl.

[0028] 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.

[0029] The aryloxy group in the present invention includes a monovalent group composed of the above-mentioned aryl group and heteroaryl group and oxygen.

[0030] Examples of the C6-C30 arylamino group mentioned in the present invention include phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrenylamino, and biphenylamino.

[0031] Examples of the C3-C30 heteroarylamino group mentioned in the present invention include pyridylamino, pyrimidinylamino, and dibenzofuranylamino.

[0032] The chain alkyl group mentioned in the present invention, unless otherwise specified, includes straight-chain alkyl groups and branched-chain alkyl groups. Specifically, the substituted or unsubstituted C1-C30 chain alkyl group is preferably a substituted or unsubstituted C1-C16 chain alkyl group, and more preferably a substituted or unsubstituted C1-C10 chain alkyl group. The substituted or unsubstituted C3-C30 cycloalkyl group is preferably a substituted or unsubstituted C3-C20 cycloalkyl group, and more preferably a substituted or unsubstituted C3-C10 cycloalkyl group, for example: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, tert-pentyl, cyclohexyl, adamantyl, etc.

[0033] Furthermore, in the organic compound of the present invention represented by formula (1), X is preferably O or CR7R8.

[0034] Furthermore, when X is O, the organic compound of the present invention preferably has a structure as shown in any one of Formula (2-1), Formula (2-2) or Formula (2-3):

[0035]

[0036] Wherein, the definitions of L1, L2, Ar1, Ar2, Ar3, Ar4, R1, R2, R3, R4, a, b, c, and d are the same as those in formula (1).

[0037] Preferably, in formula (2-1), formula (2-2), and formula (2-3), L1 and L2 are both single bonds.

[0038] And / or, preferably, in formula (2-1), formula (2-2), and formula (2-3), a, b, c, and d are all 0.

[0039] And / or, preferably, in formula (2-1), formula (2-2), and formula (2-3), Ar1, Ar2, Ar3, and Ar4 are independently selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups; preferably, r1, Ar2, Ar3, and Ar4 are independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, one of naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 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, benzofluorenyl, furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothienyl, acridinyl, pyridyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, and phenazinyl;

[0040] When the above-mentioned Ar1, Ar2, Ar3, and Ar4 have a substituent group, the substituent group is selected from one or a combination of at least two of deuterium, halogen, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0041] Furthermore, when X is CR7R8, the organic compound of the present invention preferably has a structure as shown in any one of Formula (3-1), Formula (3-2), Formula (3-3), Formula (3-4) or Formula (3-5):

[0042]

[0043] Wherein, the definitions of L1, Ar1, Ar2, R1, R2, R3, R4, R7, R8, a, b, c, and d are the same as those in formula (1).

[0044] Preferably, in formula (3-1), formula (3-2), formula (3-3), formula (3-4), and formula (3-5), L1 is a single bond.

[0045] And / or, preferably, in formula (3-1), formula (3-2), formula (3-3), formula (3-4) or formula (3-5), a, b, c, and d are all 0.

[0046] And / or, preferably, in formula (3-1), formula (3-2), formula (3-3), formula (3-4) or formula (3-5), Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups; preferably, Ar1 and Ar2 are independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, one of naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 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, benzofluorenyl, furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothienyl, acridinyl, pyridyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, and phenazinyl;

[0047] Further preferably, in formula (3-1), formula (3-2), formula (3-3), formula (3-4) or formula (3-5), R7 and R8 are each independently selected from a substituted or unsubstituted C1 to C18 chain alkyl group or a substituted or unsubstituted C6 to C24 aryl group; more preferably, R7 and R8 are each independently selected from the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, more preferably phenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, one of naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 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, benzofluorenyl, furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothienyl, acridinyl, pyridyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, and phenazinyl;

[0048] 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 deuterium, halogen, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0049] Furthermore, the organic compound of the present invention has a structure shown in any one of formula (2-1-1), formula (2-2-1), and formula (2-3-1), wherein the definitions of L1, Ar1, Ar2, L2, Ar3, and Ar4 are the same as those in formula (1):

[0050]

[0051] Furthermore, the organic compound of the present invention has a structure represented by any one of Formula (3-1-1), Formula (3-2-1), Formula (3-3-1), Formula (3-4-1), Formula (3-5-1), Formula (3-1-2), Formula (3-2-2), Formula (3-3-2), Formula (3-4-2) or Formula (3-5-2), wherein L1, Ar1, and Ar2 are defined the same as in Formula (1):

[0052]

[0053]

[0054] Furthermore, in the above general formulas of the organic compounds of the present invention, Ar1-Ar4 may further preferably be the following substituted or unsubstituted groups:

[0055]

[0056] 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 deuterium, halogen, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0057] The inventors of the present invention have discovered that the structure of chemical formula (A) has good planarity and planar conjugation ability, and thus has excellent charge transport ability. The triarylamine compound designed with it as the core has high hole mobility, improved injection ability, and increased device efficiency.

[0058]

[0059] In the present invention, a series of triarylamine compounds are designed using a unique core structure having a molecular core structure such as Formula (A). These compounds exhibit excellent hole mobility. These compounds can generally be used as carrier transport layer materials in organic electroluminescent devices, including but not limited to hole transport layer materials and electron blocking layer materials.

[0060] The general formula (1) structure of the present invention is specifically that the two naphthyl groups in the binaphthyl compound are connected by a divalent atom to form a planar six-membered ring structure. Since the naphthyl group itself has the characteristic of planar rigidity, the molecule of formula (1) can form a larger planar π-conjugated structure. This large planar conjugated structure further enhances the excellent charge transport capability of the binaphthyl compound, while improving the molecular orbital energy level. The molecule has a lower HOMO energy level, which can enhance the material's injection capability from the positive electrode. These structural features enable the compound of the present invention to have excellent hole transport efficiency and injection capability, thereby reducing the operating voltage of the device and improving the efficiency of the device.

[0061] It should be noted that, while the potential effects of various groups / features are described separately for ease of explanation, this does not imply that these groups / features function in isolation. In fact, the key to achieving good performance is the optimized combination of the entire molecule, resulting from the synergistic effects of the various groups, rather than the effects of any single group.

[0062] 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:

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075] As another aspect of the present invention, there is also provided a use of the compound as described above in an organic electroluminescent device. Specifically, the compound is preferably used as a light-emitting layer material in the organic electroluminescent device, and more preferably as a hole transport layer material or electron blocking layer material in the organic electroluminescent device.

[0076] In addition to organic electroluminescent devices, the compound of the present invention can also 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 paper.

[0077] 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 represented by at least one of the structures of C1 to C338 as described above.

[0078] Specifically, one 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 layer comprises a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, wherein 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 a light-emitting layer is formed 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 C338 as shown above.

[0079] The present invention further discloses a display screen or a display panel, wherein the organic electroluminescent device described above is adopted in the display screen or the display panel; preferably, the display screen or the display panel is an OLED display.

[0080] 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. DETAILED DESCRIPTION

[0081] The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the embodiments are merely to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0082] The mass spectrometry data in the following synthesis examples were obtained by using a ZAB-HS mass spectrometer manufactured by Micromass, UK.

[0083] Synthesis Example 1: Synthesis of Compound C1

[0084]

[0085] In a 500 mL single-necked flask, add 30.0 g (90.4 mmol) of 1-bromo-8-iodonaphthalene, 20.4 g (108.4 mmol) of 2-hydroxy-1-naphthaleneboronic acid, 1.00 g (0.900 mmol) of tetrakis(triphenylphosphine)palladium (i.e., Pd(PPh3)4), 300 mL of toluene, 50 mL of ethanol, 30 mL of water, and 16.2 g (117.6 mmol) of potassium carbonate (K2CO3). Vacuum and replace with nitrogen three times. The reaction temperature is raised to 90°C and the reaction is allowed to react for 7 h. After completion of the reaction, the reaction is stopped. Cool to room temperature, separate the reaction mixture, concentrate the organic phase, add methanol, stir for 1 h, and filter to obtain 20.0 g of yellow powder A-1, M / Z measured: 349 (M+H).

[0086] In a 500 mL single-necked flask, add 20.0 g (57.4 mmol) of A-1, 11.8 g (86.0 mmol) of potassium carbonate (K2CO3), and 400 mL of N,N-dimethylformamide (DMF). The reaction temperature was raised to 120°C for 16 h. Upon completion, the reaction was stopped. After cooling to room temperature, the reaction solution was poured into water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated to obtain a yellow oil. The solid precipitated by stirring in n-hexane was filtered to obtain 6.5 g of a light yellow powder A-2, M / Z found: 269 (M+H).

[0087] In a 250 mL three-necked flask, 6.5 g (24.3 mmol) of A-2 was dissolved in tetrahydrofuran. The reaction system was cooled to 0°C in an ice-salt bath. Then, 4.3 g (24.3 mmol) of N-bromosuccinimide was added to the reaction solution in batches. After the addition was complete, the system was allowed to react for 4 h. The solution was then poured into a sodium thiosulfate solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated to obtain a yellow solid. The product was recrystallized from toluene and ethanol and filtered to obtain 6.0 g of a light yellow powder A-3. Found M / Z: 347 (M+H)

[0088] In a 250mL three-necked flask, 6.0g (17.3mmol) A-3, 2.7g (15.6mmol) diphenylamine, 0.16g (0.173mmol) tris (dibenzylideneacetone) dipalladium (ie Pd2 (dba) 3), 0.1mL tri-tert-butylphosphine xylene solution, 2.5g (26.0mmol) sodium tert-butoxide (NaOBu-t), 80mL toluene (Toluene) were added in sequence, and the vacuum was replaced with nitrogen 3 times. The reaction temperature was raised to 100°C and the reaction was reacted for 4h. After the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction solution was passed through a short silica gel column and washed with toluene until there was no product. The toluene was concentrated to obtain a yellow oil. Methanol was added and stirred to slowly precipitate the solid. The solid was recrystallized in toluene and ethanol, and 5.2g of light yellow powder compound C1 was obtained by filtration. M / Z measured value: 436 (M+H)

[0089] The compounds in Synthesis Examples 2 to 15 were synthesized using A-3 as an intermediate according to the method of Synthesis Example 1. The specific structures are shown in Table 1:

[0090] Table 1:

[0091]

[0092]

[0093]

[0094]

[0095] Synthesis Example 16: Compound C113

[0096]

[0097] In a 500 mL single-necked flask, add 30.0 g (100.0 mmol) of 1,4-dibromo-2-naphthol, 25.0 g (100.0 mmol) of 8-bromo-1-naphthylboronic acid, 1.00 g (0.900 mmol) of tetrakis(triphenylphosphine)palladium (i.e., Pd(PPh3)4), 300 mL of toluene, 50 mL of ethanol, 50 mL of water, and 16.2 g (117.6 mmol) of potassium carbonate (K2CO3). Vacuum and replace with nitrogen three times. The reaction temperature was raised to 90°C and the reaction was allowed to react for 7 h. After completion of the reaction, the reaction was stopped. The reaction mixture was cooled to room temperature, separated, and the organic phase was concentrated. Methanol was added and stirred for 1 h. Filtered to obtain 27.0 g of a brown powder B-1, M / Z found: 427 (M+H).

[0098] In a 500 mL single-necked flask, add 21.0 g (50.0 mmol) of B-1, 19.3 g (70.0 mmol) of potassium carbonate (K2CO3), and 350 mL of N,N-dimethylformamide (DMF). The reaction temperature was raised to 120°C for 16 h. After completion, the reaction was stopped. After cooling to room temperature, the reaction solution was poured into water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated to obtain a yellow oil. Stir in n-hexane to precipitate a solid, which was filtered to obtain 10.6 g of a yellow powder, B-2. Found M / Z: 347 (M+H).

[0099] To a 250 mL three-necked flask, add 8.5 g (24.6 mmol) of B-2, 8.3 g (24.6 mmol) of N-(4-(tert-butyl)phenyl)-9,9-dimethyl-9H-fluoren-3-amine, 0.23 g (0.246 mmol) of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.1 mL of tri-tert-butylphosphine in xylene, 3.5 g (37.0 mmol) of sodium tert-butoxide (NaOBu-t), and 150 mL of toluene. Vacuum the mixture and replace the atmosphere with nitrogen three times. Raise the temperature to 100°C and allow the reaction to proceed for 4 h. After completion, stop the reaction. Cool to room temperature, pass the reaction mixture through a silica gel column, and elute with toluene until no product is present. Concentrate the toluene to obtain a yellow oil. Add methanol and stir, and a solid will slowly precipitate. The solid was recrystallized from toluene and ethanol, and filtered to obtain 7.3 g of light yellow powder compound C113, M / Z found: 608 (M+H)

[0100] The compounds in Synthesis Examples 17 to 26 were synthesized using B-2 as an intermediate according to the method of Synthesis Example 16. The specific structures are shown in Table 2:

[0101] Table 2:

[0102]

[0103]

[0104]

[0105] Synthesis Example 27: Compound C125

[0106]

[0107] In a 250 mL single-necked flask, 18.0 g (70.3 mmol) of 1-bromo-6-chloro-2-naphthol, 19.4 g (77.3 mmol) of 8-bromo-1-naphthylboronic acid, 0.80 g (0.700 mmol) of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), 180 mL of toluene, 20 mL of ethanol, 20 mL of water, and 11.6 g (84.5 mmol) of potassium carbonate (K2CO3) were added. The mixture was evacuated and replaced with nitrogen three times. The temperature was raised to 90°C and the reaction mixture was allowed to react for 7 h. After completion of the reaction, the reaction mixture was stopped. The mixture was cooled to room temperature, the reaction mixture was separated, and the organic phase was concentrated. Methanol was added and stirred for 1 h. Filtered to obtain 14.6 g of a khaki powder, C-1, with an M / Z value of 383 (M+H).

[0108] In a 250 mL single-necked flask, add 14.0 g (36.5 mmol) of C-1, 6.9 g (50.0 mmol) of potassium carbonate (K2CO3), and 200 mL of N,N-dimethylformamide (DMF). The reaction temperature was raised to 120°C for 16 h. Upon completion, the reaction was stopped. After cooling to room temperature, the reaction solution was poured into water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, concentrated, and passed through a silica gel column (petroleum ether / ethyl acetate, 10 / 1) to obtain a pale yellow solid and 7.8 g of C-2 as a yellow powder. Found M / Z: 303 (M+H).

[0109] To a 250 mL three-necked flask, add 5.0 g (16.5 mmol) of C-2, 6.0 g (16.5 mmol) of N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-9H-fluoren-2-amine, 0.16 g (0.170 mmol) of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.1 mL of tri-tert-butylphosphine in xylene, 3.0 g (22.0 mmol) of sodium tert-butoxide (NaOBu-t), and 80 mL of toluene. Vacuum the mixture and replace the atmosphere with nitrogen three times. Raise the temperature to 120°C and allow the reaction to proceed for 6 h. After completion, stop the reaction. Cool to room temperature, pass the reaction mixture through a silica gel column, and elute with toluene until no product is present. Concentrate the toluene to obtain a yellow oil. Add methanol and stir, and a solid will slowly precipitate. The solid was recrystallized from toluene and ethanol, and filtered to obtain 5.3 g of light yellow powder compound C125, M / Z found: 628 (M+H)

[0110] The compounds in Synthesis Examples 28 to 38 were synthesized using C-2 as an intermediate by referring to the method of Synthesis Example 27. The specific structures are shown in Table 3:

[0111] Table 3:

[0112]

[0113]

[0114]

[0115]

[0116] The synthesis method of intermediate D-3 required for formula (6-1) is as follows:

[0117]

[0118] In a 250 mL single-necked flask, 20.0 g (75.8 mmol) of methyl 8-bromo-1-naphthoate, 17.2 g (83.3 mmol) of 4-chloro-1-naphthoboric acid, 0.80 g (0.700 mmol) of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), 180 mL of toluene, 30 mL of ethanol, 30 mL of water, and 20.9 g (151.6 mmol) of potassium carbonate (K2CO3) were added. The mixture was evacuated and replaced with nitrogen three times. The temperature was raised to 90°C and the reaction mixture was allowed to react for 7 h. After completion of the reaction, the reaction mixture was stopped. The mixture was cooled to room temperature, the reaction mixture was separated, and the organic phase was concentrated. Methanol was added and stirred for 1 h. The mixture was filtered to obtain 20.6 g of a khaki powder D-1. M / Z found: 347 (M+H).

[0119] In a dry 500mL three-necked flask, a reflux condenser, a nitrogen conduit, and a constant pressure funnel were added. 15g (43.4mmol) of D-1 was dissolved in an anhydrous tetrahydrofuran solution dried over sodium, placed in a bottle, and cooled to -5°C by a cryosel bath. Under a nitrogen atmosphere, a tetrahydrofuran solution of methylmagnesium bromide (43.4mL, 130.2mmol, 3.0M in THF) was slowly added dropwise to the above solution by a constant pressure funnel. After dropwise addition, the reaction was incubated for half an hour, the cryosel bath was removed, and the mixture was stirred at room temperature overnight. The reaction solution was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and concentrated to remove the solvent to give a brown oil. The crude product was purified by column chromatography (petroleum ether / ethyl acetate, 10 / 1-5 / 1) to give 8.9g of light yellow solid D-2, M / Z measured value: 347 (M+H).

[0120] 8 g (23.1 mmol) of D-2 was dissolved in a mixture of 30 mL of acetic acid and 5 mL of concentrated hydrochloric acid. The mixture was heated to 100°C for 16 h and allowed to cool to room temperature to precipitate a solid. The solid was collected and washed with water and methanol to yield 7.0 g of product D-3, M / Z found: 329 (M+H).

[0121] Similarly, the intermediate E-3 required for formula (6-2) can be obtained by referring to the synthesis method of D-3:

[0122]

[0123] The 4-chloro-1-naphthaleneboronic acid in D-3 was replaced with 8-chloro-1-naphthaleneboronic acid, and the M / Z value was found to be 329 (M+H). Similarly, the intermediate F-3 required by formula (6-3) can be obtained by referring to the synthesis method of D-3:

[0124]

[0125] The 4-chloro-1-naphthaleneboronic acid in D-3 was replaced with 7-chloro-1-naphthaleneboronic acid, and the M / Z value was found to be 329 (M+H). Similarly, the intermediate G-3 required for formula (6-4) can be obtained by referring to the synthesis method of D-3:

[0126]

[0127] The 4-chloro-1-naphthaleneboronic acid in D-3 was replaced with 6-chloro-1-naphthaleneboronic acid, and the M / Z value was found to be 329 (M+H). Similarly, the intermediate H-3 required for formula (6-5) can be obtained by referring to the synthesis method of D-3:

[0128]

[0129] The 4-chloro-1-naphthaleneboronic acid in D-3 was replaced with 5-chloro-1-naphthaleneboronic acid, and the M / Z value was found to be 329 (M+H). The synthesis method of the intermediate I-3 required by formula (7-1) is as follows:

[0130]

[0131] In a 500 mL single-necked flask, 30.0 g (90.4 mmol) of 8-iodo-1-bromonaphthalene, 19.6 g (95.0 mmol) of 4-chloro-1-naphthaleneboronic acid, 1.1 g (0.900 mmol) of tetrakis(triphenylphosphine)palladium (i.e., Pd(PPh3)4), 300 mL of toluene, 50 mL of ethanol, 50 mL of water, and 20.9 g (151.6 mmol) of potassium carbonate (K2CO3) were added. The mixture was evacuated and replaced with nitrogen three times. The temperature was raised to 90°C and the reaction was allowed to proceed for 7 h. After completion of the reaction, the reaction was stopped. The mixture was cooled to room temperature, the reaction solution was separated, and the organic phase was concentrated. Methanol was added and stirred for 1 h. Filtered to obtain 26.5 g of a khaki powder I-1, M / Z found: 367 (M+H).

[0132] In a dry 500mL three-necked flask, a nitrogen conduit and a constant pressure dropping funnel are configured. 20g (54.6mmol) of I-1 are dissolved in a 250mL anhydrous tetrahydrofuran solution dried over sodium, placed in a bottle, and cooled to -78°C by a liquid nitrogen-acetone bath. Under nitrogen protection, n-butyllithium solution (26.0mL, 65.2mmol, 2.5M in hexane) is slowly added dropwise to the above solution through a constant pressure dropping funnel. After dripping, the reaction is incubated for half an hour, and then 11.9g (65.2mmol) of benzophenone is dissolved in 80mL anhydrous tetrahydrofuran, added dropwise to the above reaction solution, and stirred at room temperature overnight. The reaction solution is poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate, and the organic phase is dried over anhydrous sodium sulfate, concentrated to remove the solvent, and a brown oil is obtained. The crude product was purified by column chromatography (petroleum ether / ethyl acetate, 10 / 1-5 / 1) to give 18 g of light yellow solid I-2, M / Z found: 471 (M+H).

[0133] 18 g (38.2 mmol) of I-2 was dissolved in a mixture of 200 mL of acetic acid and 40 mL of concentrated hydrochloric acid. The mixture was heated to 100°C for 16 h and allowed to cool to room temperature to precipitate a solid. The solid was collected and washed with water and methanol to yield 10.0 g of product I-3, M / Z found: 453 (M+H).

[0134] The synthesis method of intermediate J-3 required for formula (7-2) is as follows:

[0135]

[0136] The 4-chloro-1-naphthaleneboronic acid in I-3 was replaced by 8-chloro-1-naphthaleneboronic acid, and the M / Z found was 453 (M+H).

[0137] The synthesis method of the intermediate K-3 required by formula (7-3) is as follows:

[0138]

[0139] The 4-chloro-1-naphthaleneboronic acid in I-3 was replaced by 7-chloro-1-naphthaleneboronic acid, and the M / Z found was 453 (M+H).

[0140] The synthesis method of the intermediate L-3 required for formula (7-4) is as follows:

[0141]

[0142] The 4-chloro-1-naphthaleneboronic acid in I-3 was replaced by 6-chloro-1-naphthaleneboronic acid, and the M / Z found was 453 (M+H).

[0143] The synthesis method of the intermediate M-3 required for formula (7-5) is as follows:

[0144]

[0145] The 4-chloro-1-naphthaleneboronic acid in I-3 was replaced by 5-chloro-1-naphthaleneboronic acid, and the M / Z found was 453 (M+H).

[0146] Synthesis Examples 38 to 60 can be obtained by referring to the last step of Synthesis Example 27. The required intermediates and raw materials are shown in Table 4:

[0147] Table 4:

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156] Device Examples

[0157] An OLED includes a first electrode, a second electrode, and an organic material layer between the electrodes. The organic material layer 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.

[0158] In a specific embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is made of glass or a polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, the substrate used for the display can also be provided with thin film transistors (TFTs).

[0159] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode serves as an anode, transparent conductive oxide materials 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 serves as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used, as well as any combination thereof.

[0160] 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.

[0161] 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 single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. The hole transport region can also be a multilayer structure comprising at least one of the following: 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.

[0162] 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.

[0163]

[0164]

[0165]

[0166] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound or a combination of multiple compounds. For example, the hole injection layer can use one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds HI-1 to HI-3 described below. Alternatively, one or more of the compounds HT-1 to HT-51 can be doped with one or more of the compounds HI-1 to HI-3 described below.

[0167]

[0168] The light-emitting layer includes a luminescent dye (i.e., a dopant) that can emit light at different wavelengths, and may also include a host material. The light-emitting layer can be a monochromatic light-emitting layer that emits a single color, such as red, green, or blue. Multiple monochromatic light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or they can be stacked together to form a multi-color light-emitting layer. When light-emitting layers of different colors 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 simultaneously emit different colors, such as red, green, and blue.

[0169] Depending on the technology, the light-emitting layer material can be made of fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescence materials, and other materials. An OLED device can use a single light-emitting technology or a combination of multiple technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0170] 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.

[0171]

[0172] 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.

[0173]

[0174]

[0175] 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.

[0176]

[0177]

[0178]

[0179]

[0180] 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.

[0181]

[0182]

[0183] D stands for deuterium.

[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 RPD-1 to RPD-28 listed below.

[0185]

[0186]

[0187] 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.

[0188]

[0189] The OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode. This region may be a single-layer electron transport layer (ETL), including those containing only one compound and those containing multiple compounds. The region may also be a multilayer structure comprising at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0190] 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.

[0191]

[0192]

[0193]

[0194]

[0195] 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.

[0196] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Yb, Li or Ca.

[0197] The preparation process of the organic electroluminescent device in this embodiment is as follows:

[0198] Example 1: Compounds of the present invention used as hole transport materials

[0199] Glass plates coated with an ITO transparent conductive layer were ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent, baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0200] Place the glass substrate with the anode in a vacuum chamber and evacuate to a vacuum of <1×10 -5 On the anode film, a 10nm hole-injection layer (HIL) of a mixture of compounds C3 and HI-3 (97 / 3, w / w) was vacuum-evaporated in this order: a 60nm hole-transport layer (HTL) of compound C3; a 5nm electron-blocking layer (EB) of compound HT-48; a 40nm luminescent layer of a binary mixture of compounds PH-34 and RPD-10 (100:3, w / w); a 5nm hole-blocking layer (HTL) of ET-23; a 25nm electron-transport layer (ETL) of a mixture of compounds ET-69 and ET-57 (50 / 50, w / w); a 1nm electron-injection layer of LiF; and a 150nm cathode layer of aluminum. The total deposition rate for all organic layers and LiF was controlled at 0.1nm / s, and the deposition rate for the metal electrode was controlled at 1nm / s.

[0201] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0202] At the same brightness, a digital source meter and a luminance 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 luminance of the organic electroluminescent device was measured when it reached 3000 cd / m 2 The voltage at which the luminance is at 10000cd / m 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. The life test of LT98 is as follows: Use a luminance meter at 10000cd / m 2 Under the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to be reduced to 9800cd / m 2 The time in hours.

[0203] In Examples 2-26, compound C3 in Example 1 was replaced by the compounds of the present invention listed in Table 1; in Comparative Examples 1-4, compound C3 was replaced by comparative compounds R-1, R-2, R-3, and R-4 shown in Table 1, respectively.

[0204] Comparative Example compounds R-1 to R-4 are as follows:

[0205] R-1:(CN111662188A)

[0206]

[0207] R-2:(CN101228250A)

[0208]

[0209] R-3:(KR1020190118514A)

[0210]

[0211] R-4:(KR1020170137976A)

[0212]

[0213] Table 5: Comparison of device performance when the compounds of the present invention and comparative compounds are used as hole transport materials.

[0214]

[0215]

[0216] From the results in Table 5, it can be seen that when the compound of the present invention is used as a hole transport material in a device, the current efficiency can reach above 16.0 cd / A, while the lifespan is greatly improved and the voltage is reduced, making it a hole transport material with good performance.

[0217] Compound R-1 in Comparative Example 1, which contains an electron-deficient fused aromatic ring-like phenanthridine structure, forms a trap for hole carriers, hindering hole transport and disrupting the carrier balance of the device, resulting in very short efficiency and lifespan. Compound R-4 in Comparative Example 4, whose fused aromatic ring structure exhibits significantly lower hole carrier transport mobility than aromatic amine structures, severely impacts device performance.

[0218] Compared with Comparative Examples 2 and 3, the compounds of the present invention also show obvious performance advantages. This is because the aromatic amine compounds of this type have strong carrier transport capabilities, which are conducive to meeting the charge transfer balance of the device, thereby significantly improving the voltage, luminous efficiency and device life.

[0219] The compounds of the present invention can also be used as electron blocking materials. Examples 27 to 45 were completed, whereby compound C3 in Example 1 was replaced with HT49, and HT-48 was replaced with the compounds shown in Table 6.

[0220] Table 6: Comparison of device performance when the compounds of the present invention and comparative compounds are used as electron blocking materials

[0221]

[0222]

[0223] As can be seen from Table 6, when the compounds of the present invention are used as electron blocking layers, the organic electroluminescent devices prepared using the compounds of the present invention also have significant improvements in voltage, luminous efficiency and device life compared to devices prepared using the comparative compounds.

[0224] The compound of the present invention uses an aromatic amine compound having formula (1) as a parent core, and introduces a planar large conjugated structure to increase the HOMO energy level of the material, facilitate hole injection, thereby reducing the operating voltage of the device; improving the carrier transport capability, enhancing the luminous efficiency of the device, and extending the operating life. Therefore, the compound of the present invention is a hole transport material and electron blocking material with good performance.

[0225] 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 invention.

Claims

1. An organic compound having a structure as shown in formula (1): In formula (1), Said L1 and L2 are independently selected from single bonds; Said X is selected from S, O or CR7R8; R7 and R8 are independently selected from one of a substituted or unsubstituted C1-C30 chain alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a C3-C20 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group, and R7 and R8 are not connected to each other by a chemical bond to form a ring; Ar1, Ar2, Ar3, and Ar4 are independently selected from a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group; m and n are each independently 0 or 1, and m+n=1; Said R1, R2, R3, and R4 are independently hydrogen or deuterium; The a, b, c, and d are independently selected from 1 to the maximum possible integer value, and multiple R1, multiple R2, multiple R3, and multiple R4 are each the same or different groups; 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, deuterium, halogen, C1-C30 chain alkyl, C1-C30 alkoxy, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

2. The organic compound according to claim 1, wherein in formula (1), X is O or CR7R8.

3. The organic compound according to claim 1, having a structure as shown in any one of Formula (2-1), Formula (2-2) or Formula (2-3): in, The definitions of L1, L2, Ar1, Ar2, Ar3, Ar4, R1, R2, R3, R4, a, b, c, and d are the same as those in formula (1).

4. The organic compound according to claim 3, wherein in formula (2-1), formula (2-2), and formula (2-3), L1 and L2 are both single bonds; And / or, in formula (2-1), formula (2-2), and formula (2-3), Ar1, Ar2, Ar3, and Ar4 are independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, one of naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, benzofluorenyl, furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, acridinyl, pyridyl, benzocarbazolyl, phenothiazinyl, and phenazinyl; When the above-mentioned Ar1, Ar2, Ar3, and Ar4 have a substituent group, the substituent group is selected from one or a combination of at least two of deuterium, halogen, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

5. The organic compound according to claim 1, having a structure as shown in any one of Formula (3-1), Formula (3-2), Formula (3-3), Formula (3-4) or Formula (3-5): in, The definitions of L1, Ar1, Ar2, Ar3, Ar4, R1, R2, R3, R4, R7, R8, a, b, c, and d are the same as those in formula (1).

6. The organic compound according to claim 5, wherein in formula (3-1), formula (3-2), formula (3-3), formula (3-4), and formula (3-5), L1 is a single bond; And / or, in formula (3-1), formula (3-2), formula (3-3), formula (3-4) or formula (3-5), Ar1 and Ar2 are independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, one of naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, benzofluorenyl, furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, acridinyl, pyridyl, benzocarbazolyl, phenothiazinyl, and phenazinyl; In formula (3-1), formula (3-2), formula (3-3), formula (3-4) or formula (3-5), R7 and R8 are each independently a substituted or unsubstituted C1 to C18 chain alkyl group or a substituted or unsubstituted C6 to C24 aryl group; 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 deuterium, halogen, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

7. The organic compound according to claim 5, wherein in formula (3-1), formula (3-2), formula (3-3), formula (3-4), and formula (3-5), R7 and R8 are independently selected from the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, one of naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, benzofluorenyl, furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, acridinyl, pyridyl, benzocarbazolyl, phenothiazinyl, and phenazinyl; 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 deuterium, halogen, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

8. The organic compound according to claim 1, having a structure as shown in any one of Formula (2-1-1), Formula (2-2-1), and Formula (2-3-1), wherein L1, Ar1, Ar2, L2, Ar3, and Ar4 are defined the same as in Formula (1): Alternatively, it has a structure represented by any one of Formula (3-1-1), Formula (3-2-1), Formula (3-3-1), Formula (3-4-1), Formula (3-5-1), Formula (3-1-2), Formula (3-2-2), Formula (3-3-2), Formula (3-4-2) or Formula (3-5-2), wherein the definitions of L1, Ar1, and Ar2 are the same as those in Formula (1):

9. An organic compound having the structure shown below:

10. Use of the organic compound according to any one of claims 1 to 9, 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, an organic thin film transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper; The organic compound is used as a hole transport layer material or an electron blocking layer material in an organic electroluminescent device.

11. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layer contains the organic compound according to any one of claims 1 to 9; The light-emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer. The hole transport layer or the electron blocking layer contains the organic compound described in any one of claims 1 to 9.

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