Organic compound and application thereof

Abstract

The invention relates to an organic compound, belongs to the technical field of organic electroluminescence, and also relates to an organic electroluminescence device adopting the organic compound. The compound provided by the invention has a structure shown in the specification. The compound disclosed by the invention is simple to prepare and relatively good in thermal stability, and when the compound is prepared and applied to an organic electroluminescent device, the transmission of carriers in the device can be improved and balanced, the voltage of the device is reduced, the luminous efficiency is improved and the service life is prolonged. # imgabs0 #

Description

Technical Field

[0001] The invention relates to an organic compound, in particular to a benzotriphenylene derivative bridged by dibenzothiophene, belonging to the technical field of organic light-emitting materials, and also 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] Although products using OLED display technology have been commercialized, the device's lifespan, efficiency and other performance still need to be continuously improved to meet people's pursuit of higher quality. Therefore, the 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 view of the shortcomings of the prior art, one of the objectives of the present invention is to provide a derivative of a benzotriphenylene group and a nitrogen-containing electron-deficient group bridged by dibenzothiophene, and the compound with this structure has good photoelectric properties when applied to OLED devices.

[0007] To achieve this object, the present invention provides an organic compound having a structure as shown in formula (1):

[0008]

[0009] In formula (1), R1 and R2 each independently represent a single substitution group to the maximum allowed number of substitution groups, and R1 and R2 each independently represent one selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryl;

[0010] X1, X2, X3, X4, and X5 are each independently selected from CR 1 or N, and at least one of them is N;

[0011] R 1 represents a substituent group connected by a single bond or fused connection, R 1 are each independently selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the R 1 The substituents substituted above are not connected or connected to form a ring through a single bond, S or O;

[0012] The above R1, R2, R 1 When there are substituents in , the substituents are each independently selected from at least one of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C30 chain alkyl, C1-C30 alkoxy, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, C1-C30 alkylsilyl, C6-C60 aryl, C6-C60 aryloxy, C6-C60 arylamino, C3-C60 heteroaryl, C3-C60 heteroaryloxy or C3-C60 heteroarylamino;

[0013] The expression of a ring structure crossed out by “—” indicates that the connection site is any position on the ring structure that can form a bond, and “*” indicates the connection site of a group.

[0014] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple substituents (at least 2), they may be selected from different substituents. When the same expressions are involved in the present invention, they have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0015] In the present invention, “the R 1 The expression "representing a substituent group connected by a single bond or a fused bond" means that the group can be connected to the C atom through a single bond, and can also be connected to the adjacent C atom in the connected ring structure through a chemical bond, thereby forming a ring structure fused to the ring.

[0016] In the present invention, “the substituted substituents are each independently not connected to the adjacent ring structure” means that the substituents are only connected to the C atom through a single bond; “the substituted substituents are each independently connected to the adjacent ring structure through a chemical bond to form a ring” means that in addition to being connected to the C atom through a chemical bond, the substituents are also connected to the adjacent ring through a chemical bond, thereby forming a fused ring structure.

[0017] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The following descriptions involving the same have the same meaning.

[0018] In the present invention, the expression of chemical elements, unless otherwise specified, includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1 H (hydrogen), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C. 13 C, etc.

[0019] In the present invention, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0020] In the present invention, 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.

[0021] In the present invention, "—*", "*", Both represent the attachment point of a group.

[0022] In the present invention, the expression of Ca-Cb means that the number of carbon atoms in the group is ab. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms in the substituent.

[0023] In the present invention, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0024] In the present invention, the C6-C30 may be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28.

[0025] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0026] The C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.

[0027] The C3-C20 can all be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.

[0028] The C2-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.

[0029] The C1-C30 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26 or C28, etc.

[0030] The C2-C30 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26 or C28, etc.

[0031] The C6-C60 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0032] The C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0033] The C2-C10 can all be C3, C4, C5, C6, C7, C8, C9, etc.

[0034] In the present invention, the C6-C60 aryl group, C6-C30 aryl group, preferably C6-C20 aryl group, includes a monocyclic aryl group and a condensed ring aryl group; the monocyclic aryl group means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are connected by a single bond, and exemplary examples include but are not limited to: phenyl, biphenyl, terphenyl, quadriphenyl, etc. The fused ring aromatic group means a group containing at least two aromatic rings, and the aromatic rings share two adjacent carbon atoms and are fused to each other, including, but not limited to, naphthyl (1-naphthyl, 2-naphthyl), anthracenyl (1-anthracenyl, 2-anthracenyl, 9-anthracenyl), phenanthrenyl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, phenylmethylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl (1-pyrenyl, 2-pyrenyl, 4-pyrenyl), peryl, It should be noted that the monocyclic aromatic group and the condensed aromatic group connected by a single bond also belong to the scope of aromatic group, such as phenylnaphthyl, naphthylphenyl, etc.

[0035] The C3-C60 heteroaryl, C3-C30 heteroaryl, preferably C3-C20 heteroaryl, includes a monocyclic heteroaryl or a condensed ring heteroaryl. The monocyclic heteroaryl means that the molecule contains at least one heteroaryl. When the molecule contains a heteroaryl and other groups (such as aryl, heteroaryl, etc.), the heteroaryl and other groups are connected by a single bond, including but not limited to pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, pyrimidinylphenyl, etc. The fused ring heteroaryl group means a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two share two adjacent atoms that are fused to each other, including, but not limited to, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, naphthiobenzofuranyl, naphthiobenzothiophenyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolcarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc. It should be noted that heteroaryl and heteroaryl groups connected by a single bond, and aryl and heteroaryl groups connected by a single bond also fall within the scope of heteroaryl groups, for example, phenyldibenzofuranyl, phenyldibenzothienyl, and the like.

[0036] Specific examples of the C6-C60 arylene group and the C6-C30 arylene group include divalent groups obtained by removing a hydrogen atom from the above-mentioned aryl groups; specific examples of the C3-C60 heteroarylene group and the C3-C30 heteroarylene group include divalent groups obtained by removing a hydrogen atom from the above-mentioned heteroaryl groups.

[0037] The C1-C30 chain alkyl group (including straight chain alkyl group or branched chain alkyl group), C1-C20 chain alkyl group, preferably C1-C10 chain alkyl group, illustratively include but are not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl and the like.

[0038] Specific examples of the C1-C30 alkoxy group and the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned examples of the chain alkyl group to O.

[0039] The C2-C30 alkenyl, C2-C20 alkenyl, preferably C2-C10 alkenyl, contains at least one C=C, illustratively including but not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl and the like.

[0040] The C3-C30 cycloalkyl group, C3-C20 cycloalkyl group, preferably C3-C10 cycloalkyl group, includes a monocyclic alkyl group or a polycyclic alkyl group. A monocyclic alkyl group refers to an alkyl group containing a single cyclic structure, and a polycyclic alkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on the ring; examples include but are not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0041] Specific examples of the C2-C20 heterocycloalkyl group include groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (such as N, O, S, etc.), including but not limited to: epoxy, oxetanyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyrrolyl, tetrahydropyranyl, piperidinyl, piperazinyl, dioxane, morpholinyl, etc.

[0042] A specific example of the C1-C30 alkylsilyl group is a monovalent group formed by replacing at least one H on -SiH3 with the above-listed chain alkyl group. A specific example of the C6-C30 arylsilyl group is a monovalent group formed by replacing at least one H on -SiH3 with the above-listed aryl group. A specific example of the C1-C30 alkylC6-C30 arylsilyl group is a monovalent group formed by replacing at least one H on -SiH3 with the above-listed chain alkyl group and at least one H with the above-listed aryl group, which may be a di(C1-C30 alkyl)(C6-C30 aryl)silyl group or a (C1-C30 alkyl)di(C6-C30 aryl)silyl group.

[0043] A specific example of the C1-C30 alkylamino group is a monovalent group formed by replacing at least one H on -NH2 with the above-listed chain alkyl group. A specific example of the C2-C30 alkenylamino group is a monovalent group formed by replacing at least one H on -NH2 with the above-listed alkenyl group. A specific example of the C1-C30 alkyl C2-C30 alkenylamino group is a monovalent group formed by replacing at least one H on -NH2 with the above-listed chain alkyl group and at least one H with the above-listed alkenyl group.

[0044] The C6-C30 arylamino group is a monovalent group formed by replacing at least one H on -NH2 with the above-listed aryl group. The C3-C30 heteroarylamino group is a monovalent group formed by replacing at least one H on -NH2 with the above-listed heteroaryl group. The C6-C30 arylC3-C30 heteroarylamino group is a monovalent group formed by replacing at least one H on -NH2 with the above-listed aryl group and at least one H with the above-listed heteroaryl group.

[0045] Further, in formula (1), the number of N in X1, X2, X3, X4 and X5 is 1-3;

[0046] Preferably, at least one of X1, X3 and X5 is N;

[0047] More preferably, two or three of X1, X3 and X5 are N, and X2 and X4 are each independently selected from CR 1 ; said R 1 Each is independently selected from any one of hydrogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;

[0048] Most preferably, X1, X3 and X5 are all N, and X2 and X4 are each independently selected from CR 1 ; said R 1 Each is independently selected from any one of hydrogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

[0049] Furthermore, the compound of the present invention has a structure as shown in the following formula (2):

[0050]

[0051] In formula (1), the definitions of A, R1, and R2 are the same as those in formula (1);

[0052] Preferably, it has a structure as shown in any one of formula (2-1), formula (2-2), formula (2-3), and formula (2-4);

[0053]

[0054] More preferably, in formula (2-1), formula (2-2), formula (2-3) and formula (2-4), R1 and R2 are each independently selected from one of hydrogen, deuterium, halogen, cyano, C1~C10 chain alkyl, C1~C10 alkoxy, C3~C10 cycloalkyl, C6~C30 aryl, C6~C30 aryloxy and C3~C30 heteroaryl.

[0055] Furthermore, in formula (1), A is selected from one of the following structures: Represents the connection site:

[0056]

[0057]

[0058] wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, and the substituents in Ar1 and Ar2 are each independently selected from a deuterium, a halogen, a cyano group, a C1-C30 chain alkyl group, a C1-C30 alkoxy group, a C3-C30 cycloalkyl group, a C2-C30 heterocycloalkyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylamino group, a C3-C60 heteroaryl group, a C3-C60 heteroaryloxy group or a C3-C60 heteroarylamino group;

[0059] R 1 The definition ranges of X1, X3, and X5 are the same as those in formula (1); R 2 , R 3 Each is independently selected from hydrogen, deuterium, halogen, cyano, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl; Y is selected from S or O.

[0060] Still more preferably, said A is selected from the following structures:

[0061]

[0062] Preferably, X1, X3, and X5 are N;

[0063] The Ar1 and Ar2 are each independently selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazine, triazolyl, pyridyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, indolecarbazolyl, azadibenzothiophenyl, azadibenzofuranyl or indenocarbazolyl;

[0064] The substituents substituted in Ar1 and Ar2 are each independently selected from at least one of deuterium, halogen, cyano, C1-C30 chain alkyl, C1-C30 alkoxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0065] Furthermore, the A is selected from one of the following structures:

[0066]

[0067] Wherein, X1, X3, and X5 are N;

[0068] R1 is selected from phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazine, triazolyl, pyridyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, indolecarbazolyl, azadibenzothiophenyl, azadibenzofuranyl or indenocarbazolyl;

[0069] R 2 , R 3 Each is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0070] Furthermore, in the general formula of the compound of the present invention, R1 and R2 are each independently selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0071] The substituents in R1 and R2 are each independently selected from any one or a combination of at least two of halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl;

[0072] Preferably, R1 and R2 are both hydrogen.

[0073] Furthermore, the compounds of the present invention are preferably the following specific compounds, but the present invention is not limited to the specific compounds shown below:

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090] The compound of the invention uses dibenzothiophene connected to benzotriphenylene as the mother core structure of the molecule, introduces electron-deficient groups into the structure, and constructs a novel molecular structure through molecular structural optimization design. The sulfur atom in dibenzothiophene contains a lone pair of electrons, so the dibenzothiophene group exhibits a certain electron donation ability, which can be used as a means to regulate electron mobility; the benzotriphenylene molecule has strong rigidity, good coplanarity, and a large π electron delocalization range. When combined with dibenzothiophene, it enhances the π electron transition ability and has a gain in the carrier transport ability; the nitrogen-containing electron-deficient group can enhance the electron transport ability; by synergistically constructing its substitution position in dibenzothiophene, finely adjusting the discrete area of ​​the π electron cloud in the molecule, and adjusting the LUMO energy level of the molecule, the electron injection can be improved, and the electron transport ability of the molecule can be adjusted, thereby achieving the purpose of carrier transport balance in the device, obtaining excellent device performance, improving the efficiency of the device, and extending the life of the device.

[0091] As another aspect of the present invention, there is also provided an application of the above-mentioned compound in an organic electroluminescent device. Specifically, it is preferably used as a light-emitting layer material in an organic electroluminescent device, and more preferably used in a red light organic electroluminescent device. More preferably, the compound of the present invention is used as a host material of the organic electroluminescent device, preferably as a red light host material.

[0092] 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.

[0093] 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, wherein the organic layer contains the compound represented by formula (1) as described above.

[0094] 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 a light-emitting layer is formed between the hole transport layer and the electron transport layer; wherein the light-emitting layer comprises a main material and a doping material, and the main material comprises at least one compound represented by formula (1) as described above.

[0095] In the organic electroluminescent device of the present invention, the luminescent layer may also adopt a plurality of luminescent host materials and / or a plurality of luminescent dyes. When multiple luminescent hosts are used, the luminescent host material may include a first compound and a second compound, the first compound using at least one compound as shown in formula (1) of the present invention, and the second compound may be selected to match the energy level relationship, carrier transport performance, etc. of the first compound. The specific embodiments of the present invention list preferred device implementation schemes.

[0096] 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.

[0097] 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

[0098] 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.

[0099] The preferred compounds of the present invention can be obtained by common coupling reactions, and the representative synthesis routes are as follows:

[0100]

[0101] Among them, Ar1 and Ar2 have the same meanings as the symbols in the above text; Pd2(dba)3 represents tris(dibenzylideneacetone)dipalladium(0), Pd(dppf)Cl2 represents (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium, NaOBu-t represents sodium tert-butoxide, Pd(PPh3)4 represents tetrakis(triphenylphosphinepalladium), and SPhos represents 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl.

[0102] The preparation method of the compound of formula (1) of the present invention includes the above method, but is not limited to the above method. The compound of formula (1) synthesized by other methods by those skilled in the art also belongs to the protection scope of the present invention.

[0103] More specifically, the present invention provides a specific synthesis method of a representative compound in the following synthesis example, and the solvent and reagent used in the following synthesis example, such as 1-bromo-3-chlorodibenzothiophene, 2-chloro-4,6-diphenyl-1,3,5-triazine, trifluoromethanesulfonate benzotriphenylene, pinacol borate, tris(dibenzylideneacetone)dipalladium(0), toluene, methanol, ethanol and the like chemical reagents, can be purchased or customized from the chemical product market. In addition, those skilled in the art can also synthesize by known methods.

[0104] Synthesis Example

[0105] Synthesis of compound A1:

[0106]

[0107] Synthesis of intermediate M1:

[0108] In a 250mL three-necked flask, add 1-bromo-3-chlorodibenzothiophene S1 (0.1mol), pinacol borate (0.15mol), potassium acetate (0.2mol) and dioxane (400mL), Pd(dppf)Cl2 (0.002mol), evacuate and replace nitrogen three times, then heat to 100℃ and react for 4h. After the reaction is completed, extract with ethyl acetate and water, dry the organic phase with anhydrous sodium sulfate, dissolve the crude product in toluene after concentration, filter out the insoluble matter with a silica gel short column, and concentrate to obtain a yellow solid. The solid is stirred in methanol and filtered to obtain a gray solid as intermediate M1.

[0109] Synthesis of intermediate M2:

[0110] In a 250mL three-necked flask, add M1 (0.08mol), 6-trifluoromethanesulfonate benzotriphenylene S2 (0.96mol), potassium carbonate (0.10mol), Pd(PPh3)4 (0.0016mol), 250mL toluene, 30mL ethanol, 30mL water, evacuate the reaction system to replace nitrogen three times, heat to 100℃ and react for 8h. After the reaction, cool down to precipitate solid, collect the solid by suction, and stir the solid in petroleum ether and toluene overnight to obtain white solid M2.

[0111] Synthesis of intermediate M3:

[0112] In a 250mL three-necked flask, add M2 (0.05mol), pinacol borate (0.1mol), potassium acetate (0.15mol), Pd2(dba)3 (0.0005mol), SPhos (0.001mol) and dioxane (200mL), stir the reaction system evenly, evacuate and replace nitrogen three times, then heat to 100℃ and react for 5h. After the reaction is complete, cool down to precipitate the firmware, filter and collect the solid, stir the solid in petroleum ether and methanol for 3 hours, and collect the grayish white solid as intermediate M3.

[0113] Synthesis of compound A1:

[0114] In a 250mL three-necked flask, add M3 (0.01mol), 2-chloro-4,6-diphenyl-1,3,5-triazine S3 (0.013mol), potassium carbonate (0.015mol), Pd(PPh3)4 (0.0002mol), toluene (120mL), ethanol (15mL), water (15mL), evacuate the reaction system and replace nitrogen three times, then heat to 90℃ and react for 8h. After the reaction is completed, cool down and let stand, precipitate solid, and collect the solid. The obtained crude product is purified with toluene, and the off-white solid A1 is obtained. M / Z theoretical value: 692; measured value by ZAB-HS mass spectrometer (manufactured by Micromass, UK): 693 (M+1).

[0115] The synthesis and preparation of other compounds of the present invention can refer to the synthesis method of compound A1. By replacing different reaction raw materials S1, S2, and S3, other compounds of the present invention can be obtained, as shown in Table 1 below.

[0116] Table 1

[0117]

[0118]

[0119]

[0120]

[0121] Device Embodiment

[0122] 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.

[0123] 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.

[0124] 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), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0125] 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.

[0126] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a hole transport layer (HTL) of a single-layer structure, 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 multi-layer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0127] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives 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 derivatives, wherein the aromatic amine derivatives include compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0128]

[0129]

[0130]

[0131] 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.

[0132]

[0133] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a host material (Host). The light-emitting layer can 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 can be arranged in a plane according to a pixel pattern, or they can be stacked together to form a 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.

[0134] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. 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.

[0135] Specifically, the host material in the light-emitting layer may include a single host compound or two host compounds, and the light-emitting dye in the light-emitting layer may include one type of dye compound or two types of dye compounds. When two host compounds are included, the energy level relationship and carrier transport performance of the two compounds can be matched, designed and selected according to requirements. When two types of dye compounds are included, the light-emitting wavelengths of the two compounds and the energy level relationship with the host material can be matched, designed and selected according to requirements.

[0136] The host material in the light-emitting layer is a compound represented by formula (1) of the present invention, or a compound represented by at least one of A1 to A336 of the present invention as described above.

[0137] Specifically, in an organic electroluminescent device provided by the present invention, the main material of the light-emitting layer can only use the organic compound of the present invention as a single light-emitting main material, or the main treatment of the light-emitting layer can also adopt a technical solution of multiple light-emitting main materials and / or multiple light-emitting dyes. When multiple light-emitting main bodies are used, the light-emitting main material may include a first compound and a second compound, and the first compound uses at least one compound as shown in formula (1) of the present invention, or uses a compound with a structure shown in at least one of A1 to A336 as described above. The second compound can be selected to match the energy level relationship, carrier transport performance, etc. of the first compound, or the second compound can include a combination of one or more of the following PH-1 to PH-89, but is not limited to a combination of one or more of PH-1 to PH-89.

[0138]

[0139]

[0140]

[0141]

[0142] 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.

[0143]

[0144]

[0145] Where D is deuterium.

[0146] 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.

[0147]

[0148]

[0149] 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.

[0150]

[0151]

[0152] 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).

[0153] 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-69 listed below.

[0154]

[0155]

[0156]

[0157]

[0158] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes but is not limited to one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Yb, Li or Ca.

[0159] The preparation process of the organic electroluminescent device in this embodiment is as follows:

[0160] 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;

[0161] Place the glass substrate with ITO anode in a vacuum chamber and evacuate to <1×10 -5Pa, vacuum thermally evaporate 10nm of HT-4:HI-3 (97 / 3, w / w) mixture as hole injection layer on the above anode layer film in order; 60nm of compound HT-4 as hole transport layer; 5nm of compound HT-47 as electron blocking layer material of the device on the hole transport layer, with a total film thickness of 60nm; 40nm of main material: binary mixture of compound of the present invention: RPD-8 (97:3, w / w / w) as light emitting layer; 5nm of ET-17 as hole blocking layer of the device on the light emitting layer; 25nm of compound ET-69:ET-57 (50 / 50, w / w) mixture as electron transport layer; 1nm of LiF as electron injection layer; 150nm of metal aluminum as cathode. 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.

[0162] According to the above preparation steps and testing methods, device examples 1 to 19 of the present invention and comparative device examples 1 to 2 were completed. The main materials in examples 1 to 19 were the compounds of the present invention, and the main materials in comparative device examples 1 to 2 were the compounds B1 and B2 in the prior art.

[0163] The structural formulas of the comparative compounds B1 and B2 are as follows:

[0164] It can be obtained by referring to the method in CN108463456A; It can be obtained by referring to the method in CN112313225A;

[0165] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0166] At the same brightness, the driving voltage and current efficiency of the organic electroluminescent devices prepared in the examples and comparative examples and the life of the devices were measured. Specifically, the voltage was increased at a rate of 0.1 V per second, and the brightness of the organic electroluminescent device was measured to be 3000 cd / m 2 The voltage at which the light is on 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 LT97 is as follows: use a brightness meter at 10000cd / m 2 At the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to drop to 9700cd / m 2 The time in hours.

[0167] The performance data of the organic electroluminescent devices prepared in the above device embodiments and comparative embodiments are shown in Table 2 below. In order to better reflect the performance advantages of the present invention, the test data of comparative example 1 is set to 1, and the data in the following table are all ratios thereto.

[0168] Table 2:

[0169]

[0170]

[0171] As can be seen from Table 2 above, compared with devices prepared using prior art compounds B1 and B2, organic electroluminescent devices prepared using the compounds of the present invention as luminescent host materials have higher luminous efficiency and longer life. The inventors speculate that the reasons are as follows:

[0172] The structure of the comparison compound B1 and the A213 in Example 11 is similar, the main difference is that the 8-position of dibenzothiophene in the comparison compound B1 is connected to the 10-substituted benzotriphenylene, while A213 in Example 11 is connected to the 1-substituted benzotriphenylene at the 4-position of dibenzothiophene. A213 shows great performance excellence in terms of both life span and device efficiency. This is because the substituents of A213 are located at the 2nd and 4th positions of dibenzothiophene, that is, on the benzene ring on the same side. For the structure of the B1 compound, the LUMO energy level of the molecule is mainly distributed on the 4,6-diphenyl-1,3,5-triazine group, and the compound A213 of the present invention is under the influence of the conjugation of the benzene ring, and the LUMO orbital overlaps partially with the benzotriphenylene, and the compound structure of the present invention is more conducive to the discrete distribution of molecular orbitals, has a lower LUMO energy level, and improves the injection transmission ability and transmission ability of electrons, thereby improving device performance.

[0173] The main difference between the B2 compound in Comparative Example 1 and the A4 compound in Example 2 is the different substituent groups at the 1st position of dibenzothiophene. The B2 compound is triphenylene, and the A4 compound is benzotriphenylene. Compared with triphenylene, benzotriphenylene has a larger delocalization range of π electrons, and the increase in the conjugation range can effectively reduce the LUMO energy level of the molecule, reduce the barrier of electron injection, and thus reduce the operating voltage of the device; on the other hand, a larger conjugation range also contributes to the transition of electrons, and the enhanced electron transfer ability makes the carriers in the device body more balanced, which can increase the recombination ability of excitons; and compared with the triplet energy level (2.61ev) of triphenylene-type compounds, the introduction of benzotriphenylene improves the triplet energy level of the compound (2.30ev), and the lower triplet energy level is conducive to the transfer of energy by the dye, thereby obtaining higher device efficiency and life, thereby achieving better performance than B2.

[0174] In summary, the compounds of the present invention effectively improve the degree of conjugation of the material, adjust the LUMO energy level of the molecule, enhance the injection and transmission capacity of electrons, and make the transmission of carriers more balanced. At the same time, the material has a suitable triplet energy level, which is conducive to the transfer of exciton energy to the dye and improves the utilization rate of the excitons. At the same time, the higher triplet energy level blocks the loss of energy transfer caused by the back transfer of excitons from the dye. The compounds of the present invention can also adjust the stability of the material, and ultimately ensure that the photoelectric performance of the device prepared using the compounds of the present invention is significantly improved.

[0175] The present invention uses the above-mentioned embodiments to illustrate the compounds of the present invention and their application in OLED devices, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that It has the structure shown in the following formula (1): In formula (1), R1 and R2 each independently represent a single substitution group to the maximum permissible number of substitution groups, and R1 and R2 each independently represent one selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, and substituted or unsubstituted C3-C60 heteroaryl; X1, X2, X3, X4, and X5 are each independently selected from CR 1 or N, and at least one of them is N; R 1 represents a substituent group connected by a single bond or fused connection, R 1 are each independently selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the R 1 The substituents substituted above are not connected or connected to form a ring through a single bond, S or O; The above R1, R2, R 1 The substituents substituted in the above-mentioned substitution are each independently selected from at least one of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C30 chain alkyl, C1-C30 alkoxy, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, C1-C30 alkylsilyl, C6-C60 aryl, C6-C60 aryloxy, C6-C60 arylamino, C3-C60 heteroaryl, C3-C60 heteroaryloxy or C3-C60 heteroarylamino; The expression of a ring structure with "—" crossed out indicates that the connection site is any position on the ring structure that can form a bond, and "*" indicates the connection site of a group.

2. The organic compound according to claim 1, characterized in that The number of N in X1, X2, X3, X4 and X5 is 1-3; Preferably, at least one of X1, X3 and X5 is N; More preferably, two or three of X1, X3 and X5 are N, and X2 and X4 are each independently selected from CR 1 ; said R 1 Each is independently selected from any one of hydrogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; Most preferably, X1, X3 and X5 are all N, and X2 and X4 are each independently selected from CR 1 ; said R 1 Each is independently selected from any one of hydrogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

3. The organic compound according to claim 1, characterized in that It has the structure shown in the following formula (2): In formula (1), the definitions of A, R1, and R2 are the same as those in formula (1); Preferably, it has a structure as shown in any one of formula (2-1), formula (2-2), formula (2-3), and formula (2-4); More preferably, in formula (2-1), formula (2-2), formula (2-3) and formula (2-4), R1 and R2 are each independently selected from one of hydrogen, deuterium, halogen, cyano, C1~C10 chain alkyl, C1~C10 alkoxy, C3~C10 cycloalkyl, C6~C30 aryl, C6~C30 aryloxy and C3~C30 heteroaryl.

4. The organic compound according to claim 1, characterized in that The A is selected from one of the following structures, Represents the connection site: wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, and the substituents in Ar1 and Ar2 are each independently selected from a deuterium, a halogen, a cyano group, a C1-C30 chain alkyl group, a C1-C30 alkoxy group, a C3-C30 cycloalkyl group, a C2-C30 heterocycloalkyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylamino group, a C3-C60 heteroaryl group, a C3-C60 heteroaryloxy group or a C3-C60 heteroarylamino group; R 1 , X1, X3, and X5 have the same definition range as in formula (1); R 2 , R 3 Each is independently selected from one of hydrogen, deuterium, halogen, cyano, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl; Y is selected from S or O.

5. The organic compound according to claim 4, characterized in that The A is selected from the following structures: Preferably, X1, X3, and X5 are N; The Ar1 and Ar2 are each independently selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazine, triazolyl, pyridyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, indolecarbazolyl, azadibenzothiophenyl, azadibenzofuranyl or indenocarbazolyl; The substituents substituted in Ar1 and Ar2 are each independently selected from at least one of deuterium, halogen, cyano, C1-C30 chain alkyl, C1-C30 alkoxy, C6-C60 aryl, and C3-C60 heteroaryl.

6. The organic compound according to claim 4, characterized in that The A is selected from one of the following structures: Wherein, X1, X3, and X5 are N; R 1 is selected from phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazine, triazolyl, pyridyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, indolecarbazolyl, azadibenzothiophenyl, azadibenzofuranyl or indenocarbazolyl; R 2 , R 3 Each is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

7. The organic compound according to claim 1 or 3, characterized in that R1 and R2 are each independently selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; The substituents in R1 and R2 are each independently selected from any one or a combination of at least two of halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, R1 and R2 are both hydrogen.

8. The organic compound according to claim 1, characterized in that The compound has the following description:

9. The organic compound according to claim 1, characterized in that: The compound is used in organic electronic devices; Preferably, the organic electronic device comprises an organic electroluminescent device; Preferably, the boron-nitrogen-containing organic compound is used as a light-emitting layer material in an organic electroluminescent device.

10. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one organic compound according to any one of claims 1 to 8; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one organic compound according to any one of claims 1 to 8; Preferably, the light-emitting layer comprises a host material and a dye, and the host material comprises at least one organic compound as claimed in any one of claims 1 to 8.

11. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 10.

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