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 meanwhile, the compound disclosed by the invention can adjust the stability of a material, so that the photoelectric property of a device prepared from the compound disclosed by the invention is finally ensured to be obviously improved. # imgabs0 #

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 in an organic electroluminescent device. 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 an organic compound having a specific structure of formula (1) and its derivatives, which have good photoelectric properties when applied to OLED devices.

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

[0008]

[0009] In formula (1), X represents O or S;

[0010] R1 and R2 are each independently selected from one of hydrogen, deuterium, halogen, cyano, 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 aryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;

[0011] a represents an integer from 0 to 4, and b represents an integer from 0 to 4;

[0012] In formula A and formula B, represents the junction site;

[0013] In formula A, Ar1 and Ar2 each independently represent one of hydrogen, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;

[0014] L1, L2, and L3 each independently represent a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group;

[0015] In formula B, R3 represents a monosubstituted group or a maximum allowed number of substituted groups, and R3 is independently selected from one of hydrogen, deuterium, halogen, cyano, 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 aryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;

[0016] The substituents substituted in the above-mentioned Ar1, Ar2, L1, L2, L3, R1, R2, and R3 are each independently selected from at least one of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0017] It should be noted that, for the sake of convenience, the possible effects of each group / feature are described separately in the present invention, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between various groups and structures, rather than the effect of a single group or structure.

[0018] 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 without special explanation, and the selection range of the substituent is as shown above and will not be repeated one by one.

[0019] 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.

[0020] In the present invention, the heteroatom of the heteroaryl group is selected from atoms or atomic groups of N, O, S, P, B, Si or Se, preferably N, O or S.

[0021] In the present invention, Represents the connection site. The expression of a ring structure with a “—” crossed out indicates that the connection site is at any position on the ring structure that can form a bond.

[0022] In the present invention, the expression of Ca-Cb represents that the number of carbon atoms in the group is ab. Unless otherwise specified, the number of carbon atoms in the group generally 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 halogen includes fluorine, chlorine, bromine or iodine.

[0025] In the present invention, the C6-C30 (e.g., C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28) aromatic ring includes a single aromatic ring and a condensed aromatic ring; the single aromatic ring includes a benzene ring, a biphenyl ring or a terphenyl ring, and the condensed aromatic ring means that the ring contains at least two aromatic rings, and the aromatic rings share two adjacent carbon atoms and are condensed with each other, exemplarily including but not limited to: naphthalene ring, anthracene ring, phenanthrene ring, indene ring, fluorene ring and its derivatives (9,9-dimethylfluorene ring, benzofluorene ring, etc.), fluoranthene ring, triphenylene ring, pyrene ring, perylene ring, Ring or tetracene ring, etc.

[0026] The C3-C30 (e.g., C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28) heteroaromatic ring includes a single heteroaromatic ring or a condensed heteroaromatic ring. The single heteroaromatic ring exemplarily includes, but is not limited to, a pyrrole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a furan ring, a thiophene ring, a carbazole ring, and the like. The fused heteroaromatic ring means that the ring structure contains at least one heteroaromatic ring and one aromatic ring (heteroaromatic ring or aromatic ring), and the two share two adjacent atoms to condense each other, and exemplary examples include but are not limited to: quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, benzofuran ring, benzothiophene ring, isobenzofuran ring, isobenzothiophene ring, indole ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring and its derivatives (N-phenylcarbazole ring, benzocarbazole ring, dibenzocarbazole ring, indolecarbazole ring, azacarbazole ring, etc.), acridine ring, phenothiazine ring, phenoxazine ring, hydroacridine ring, etc.

[0027] In the present invention, the C1-C20 chain alkyl group includes C1-C20 straight chain alkyl group and C1-C20 branched chain alkyl group. For example, it can be a chain alkyl group of C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.; preferably a C1-C16 chain alkyl group; more preferably a C1-C10 chain alkyl group; illustratively including but not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl or n-decyl, etc.

[0028] In the present invention, the C2-C10 alkenyl groups can all be C2, C3, C4, C5, C6, C7, C8, C9, C10 alkenyl groups, which contain at least one C=C, illustratively including but not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0029] Specific examples of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy groups described in the present invention include monovalent groups obtained by connecting the above-mentioned chain alkyl groups to O.

[0030] In the present invention, the C3-C20 cycloalkyl group may be a cycloalkyl group of C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc., illustratively including but not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0031] A specific example of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkylsilyl group is a monovalent group in which at least one hydrogen in -SiH3 is replaced by the above-mentioned chain alkyl group; a specific example of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above-mentioned chain alkyl group.

[0032] Specific examples of the C2-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) heterocycloalkyl groups of the present invention include monovalent groups in which at least one ring C atom in the above-mentioned cycloalkyl groups is replaced by a heteroatom (e.g., O, S, N or P, etc.), including, but not limited to, epoxy, tetrahydropyrrolyl, tetrahydrofuranyl, tetrahydrothiophenyl, morpholinyl, piperidinyl, etc.

[0033] In the present invention, the C6-C60 aromatic group can be an aromatic group of 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, preferably a C6-C30 aromatic group, including a monocyclic aromatic group or a condensed ring aromatic group. The monocyclic aromatic group means that the group contains at least one phenyl group. When it contains at least two phenyl groups, the phenyl groups are connected by a single bond, and examples thereof include but are not limited to: phenyl, biphenyl, terphenyl, etc.; the condensed aromatic group means that the group contains at least two aromatic rings, and the aromatic rings share two adjacent carbon atoms and are fused to each other, and examples thereof include but are not limited to: naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, peryl, The aforementioned groups include all possible connection modes thereof.

[0034] In the present invention, the C3-C60 heteroaryl group can be a heteroaryl group of 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, preferably a C3-C30 heteroaryl group, and more preferably a C4-C20 heteroaryl group, including a monocyclic heteroaryl group or a condensed ring heteroaryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are connected by a single bond, exemplarily including but not limited to: furanyl, thienyl, pyrrolyl, pyridyl, 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: benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolcarbazolyl, azacarbazolyl, etc.), acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc.; the aforementioned groups include all feasible connection modes thereof.

[0035] Specific examples of the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) arylene group of the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned aryl groups; specific examples of the C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) heteroarylene group include divalent groups obtained by removing one hydrogen atom from the above-mentioned heteroaryl groups.

[0036] Specific examples of the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) aryloxy groups of the present invention include monovalent groups obtained by connecting the above-mentioned aryl groups to O; specific examples of the C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) heteroaryloxy groups include monovalent groups obtained by connecting the above-mentioned heteroaryl groups to O.

[0037] The C6-C60 (e.g., 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.) arylamino group described in the present invention, preferably the C6-C30 arylamino group, is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above aryl group, and illustratively includes but is not limited to phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, biphenylamino and the like.

[0038] The C3-C60 (e.g., 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.) heteroarylamino group described in the present invention, preferably the C3-C30 heteroarylamino group, is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above-mentioned heteroaryl group, and illustratively includes but is not limited to: pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0039] Furthermore, the compound of the present invention preferably has a structure as shown in formula (2-1) or formula (2-2):

[0040]

[0041] The definitions of A, B, R1, R2, a and b are the same as those in formula (1).

[0042] Furthermore, the compound of the present invention preferably has a structure as shown in any one of formulas (3-1), (3-2), (3-3), (3-4), (3-5), and (3-6):

[0043]

[0044]

[0045] Wherein, the definitions of X, A, B, R1, R2, a and b are the same as in formula (1);

[0046] Preferably, the organic compound has a structure as shown in any one of formulas (3-1), (3-2), (3-5) or (3-6).

[0047] More preferably, in the above general formula of the present invention, A is the structure of formula A:

[0048] 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, indenocarbazolyl;

[0049] The L3 is a single bond, and L1 and L2 are each independently selected from one of the following groups: phenylene, naphthylene, anthracene, phenanthrene, biphenylene, terphenylene, 9,9-dimethylfluorenylene, 9,9-diphenylfluorenylene, 9-methyl-9-phenylfluorenylene, spirofluorenylene, benzofluorenylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, carbazolylene, triazinylene, triazolylene, pyridylene, pyrimidylene, quinazolinylene, quinoxalinylene, benzimidazolylene, benzoindazolylene, benzocarbazolylene, benzofuranocarbazolylene, benzothiophenocarbazolylene, indolecarbazolylene, azadibenzothiophenylene, azadibenzofuranocarbazolylene;

[0050] The substituents substituted in the above Ar1, Ar2, L1, and L2 are each independently selected from one of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C3-C10 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0051] More preferably, in the above general formula of the present invention, B is a structure of formula B, and formula B is selected from one of the following substituted or unsubstituted structures:

[0052]

[0053] The substituent on the formula B is selected from one of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C3-C10 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl;

[0054] Preferably, the formula B is selected from one of the following structures:

[0055]

[0056] More preferably, in the above general formula of the present invention, R1 and R2 are each independently selected from one of hydrogen, deuterium, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl;

[0057] Preferably, R1 is selected from hydrogen, phenyl, biphenyl or naphthyl, and R2 is hydrogen.

[0058] The compound of the present invention uses benzonaphthofuran as the parent nucleus, selects the naphthalene ring as the connection site for molecular construction, and introduces a special coplanar large condensed aromatic group and a triazine group with electron-deficient properties to form a novel molecular structure. The good planarity of the specific aromatic group makes the molecules stacked tightly, improves the transition ability of π electrons, and its large conjugated property is connected with the naphthyl group to further improve the conjugated ability of the molecule as a whole, and has a gain in the carrier transmission ability; the triazine group is conducive to electron transmission. By collaboratively constructing the position of the substituent, the discrete area of ​​the π electron cloud in the molecule can be finely adjusted, the LUMO energy level of the molecule can be adjusted, the injection of electrons can be regulated, and the electron transmission ability of the molecule can be improved, thereby achieving the purpose of carrier transmission balance in the device, obtaining excellent device performance, reducing the device operating voltage, improving the efficiency of the device, and extending the life of the device.

[0059] More preferably, 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:

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083] The compound of the present invention uses a naphthobenzo five-membered ring as a parent core structure, and through the optimization design of the structure, two benzene rings of the naphthyl group are connected by The five-membered naphthobenzo ring and the electron-deficient group form a novel molecular structure. The molecules all have a large spatial planarity, and such a planar structure helps the molecules to stack during evaporation; secondly The naphthalene ring of the group and the parent nucleus form a large conjugated system, which enhances the delocalization range of π electrons. The synergistic effect of the two greatly improves the π-π electron transition ability and has a benefit on the carrier transmission ability; the nitrogen-containing electron-deficient group can improve the electron transmission ability; by designing triazine and The substitution position of the base on the naphthalene ring can precisely control the discrete area of ​​the π electron cloud in the molecule, adjust the LUMO energy level of the molecule, and regulate the injection of electrons. The electron-donating properties it contains can adjust the electron transport capacity of the molecule, 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.

[0084] 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.

[0085] 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.

[0086] 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.

[0087] 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.

[0088] 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.

[0089] 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.

[0090] 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

[0091] 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.

[0092] The preferred compounds of the present invention can be obtained by common coupling reactions, and the representative synthesis routes are as follows:

[0093]

[0094] or

[0095]

[0096] Wherein, L1, L2, L3, Ar1, Ar2 have the same meanings as those in formula (1);

[0097] Y and Z represent various groups that can react with boric acid or boric acid ester groups, such as chlorine, bromine, iodine, triflate, etc.

[0098] Pd2(dba)3 represents tris(dibenzylideneacetone)dipalladium(0), Pd(dppf)Cl2 represents (1,1'-bis(diphenylphosphine (2-(4-( ...nitrophenyl)ferrocene)palladium(II)chloride)) , NaOBu-t represents sodium tert-butoxide, Pd(PPh3)4 represents tetrakis(triphenylphosphine palladium), and SPhos represents 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl. 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.

[0099] More specifically, the following synthesis examples of the present invention provide a specific synthesis method of representative compounds, and the solvents and reagents used in the following synthesis examples, such as 1-bromo-3-chlorodibenzothiophene, 2-chloro-4,6-diphenyl-1,3,5-triazine, trifluoromethanesulfonate Chemical reagents such as pinacol borate, tris(dibenzylideneacetone)dipalladium(0), toluene, methanol, ethanol, etc. can all be purchased or customized from the chemical product market. In addition, those skilled in the art can also synthesize by known methods.

[0100] Synthesis example

[0101] Synthesis of compound A1:

[0102]

[0103] Synthesis of intermediate M1:

[0104] In a 250mL three-necked flask, add raw material 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 insoluble matter with silica gel short column, and concentrate to obtain a yellow solid. Stir the solid in methanol and collect by filtration to obtain an off-white solid as intermediate M1.

[0105] Synthesis of intermediate M2:

[0106] In a 250mL three-necked flask, add M1 (0.1mol), 2-chloro-4,6-diphenyl-1,3,5-triazine S2 (0.15mol), potassium carbonate (0.2mol), Pd(PPh3)4 (0.002mol), toluene (150mL), 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 to obtain gray-white solid M2.

[0107] Synthesis of intermediate M3:

[0108] 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 completed, 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.

[0109] Synthesis of compound A1:

[0110] In a 250 mL three-necked flask, add M1 (0.03 mol), 3-trifluoromethanesulfonate S2 (0.04 mol), potassium carbonate (0.06 mol), Pd (PPh3) 4 (0.0016 mol), 150 mL toluene, 10 mL ethanol, 10 mL water, the reaction system was evacuated and replaced with nitrogen three times, and the temperature was raised to 100 ° C for 8 hours. After the reaction, the temperature was lowered to precipitate a solid, which was collected by filtration and recrystallized in toluene to obtain an off-white solid A1. M / Z theoretical value: 675; ZAB-HS mass spectrometer (manufactured by Micromass, UK) measured value: 676 (M+1).

[0111] 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.

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] Device Embodiment

[0126] 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.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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).

[0131] 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.

[0132]

[0133]

[0134]

[0135] 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.

[0136]

[0137] 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.

[0138] 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.

[0139] 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.

[0140] 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 A326 of the present invention as described above.

[0141] 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 A326 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-85, but is not limited to a combination of one or more of PH-1 to PH-85.

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] 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.

[0148]

[0149]

[0150]

[0151] Where D is deuterium.

[0152] 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.

[0153]

[0154]

[0155] 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.

[0156]

[0157] 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).

[0158] 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.

[0159]

[0160]

[0161]

[0162]

[0163] 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.

[0164] The preparation process of the organic electroluminescent device in this embodiment is as follows:

[0165] 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;

[0166] Place the glass substrate with ITO anode in a vacuum chamber and evacuate to <1×10 -5 Pa, 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) 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.

[0167] According to the above preparation steps and testing methods, the device embodiments 1 to 50 of the present invention and comparative device embodiments 1 to 4 were completed. The main materials in embodiments 1 to 19 are the compounds of the present invention, and the main materials in comparative device embodiments 1 to 4 are the compounds B1, B2, B3, and B4 in the prior art. The comparative compounds B1, B2, B3, and B4 have the following structural formulas:

[0168]

[0169] It can be obtained by referring to the method in CN113316627A;

[0170]

[0171] It can be obtained by referring to the method in CN112313225A;

[0172]

[0173] Refer to the method in KR20230033786A to obtain

[0174]

[0175] Refer to the method in KR20200079980A to obtain

[0176] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0177] 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.

[0178] The performance data of the organic electroluminescent devices prepared in the above device embodiments and comparative embodiments are shown in Table 1 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.

[0179] Table 1:

[0180]

[0181]

[0182]

[0183]

[0184] As can be seen from Table 1 above, compared with devices prepared using prior art compounds B1, B2, B3, and B4, 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:

[0185] The structure of the comparison compound B1 is similar to that of A177 in Example 29, the main difference being that the comparison compound B1 is substituted with naphthyl and the compound A115 of the present invention is triphenylene. From the results, whether it is from voltage, life or device efficiency, A177 shows great performance excellence. Compared with the naphthalene ring, the triphenylene group has better molecular planarity, which is conducive to the close arrangement of molecules, and has a larger delocalization range of π electrons. The increase in the conjugation range can effectively reduce the LUMO energy level of the molecule and reduce the barrier of electron injection, thereby reducing 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 (2.41ev) of the molecule after the naphthyl substitution, the introduction of the triphenylene group improves the triplet energy level (2.30ev), and the lower triplet energy level is conducive to the transfer of the excited energy to the dye, thereby obtaining a higher device efficiency and life, thereby achieving a better performance than B1.

[0186] Similarly, the B2 compound in Comparative Example 2 contains only one triazine substituent, the π electron delocalization range of the molecule is small, the carrier transport capability is poor, and thus the device performance is poor.

[0187] Comparative Example 3 is compared with Example 1, the difference is that compound B3 is triphenylamine, and compound A1 of the present invention is Due to the presence of the aromatic amine group, compound B3 has a strong hole transport capability, which completely separates the HOMO and LUMO orbital energy levels of the molecule, and the LUMO energy level of the molecule is more concentrated on the triazine group, resulting in poor electron transport capability of the molecule and poor device performance. The base is connected to the naphthalene ring, which expands the π electron delocalization range of the molecule, overlaps the molecular energy levels, improves the electron transmission capacity, and has excellent performance.

[0188] Compound B4 in Comparative Example 4 is similar in structure to A521 in Example 51, except that the substituent of B4 is naphtho[2,3-b]benzofuran, while A521 is base. Compared with naphthoxy[2,3-b]benzofuran, the base has a stronger π electron delocalization ability, so compared with compound A521, the overall conjugation ability of the B4 molecule is weakened and the transmission performance is poor; the present invention enhances the carrier transmission ability, and the energy transfer between the host and the guest is more sufficient, so excellent performance is achieved.

[0189] In summary, the compounds of the present invention effectively improve the degree of conjugation of the material, adjust the LUNO 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 helpful for 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.

[0190] 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), X represents O or S; R1 and R2 are each independently selected from one of hydrogen, deuterium, halogen, cyano, 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 aryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; a represents an integer from 0 to 4, and b represents an integer from 0 to 4; In formula A and formula B, represents the junction site; In formula A, Ar1 and Ar2 are each independently selected from one of hydrogen, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; L1, L2, and L3 each independently represent a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; In formula B, R3 represents a monosubstituted group or a maximum allowed number of substituted groups, and R3 is independently selected from one of hydrogen, deuterium, halogen, cyano, 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 aryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; The substituents substituted in the above-mentioned Ar1, Ar2, L1, L2, L3, R1, R2, and R3 are each independently selected from at least one of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

2. The organic compound according to claim 1, characterized in that Having a structure as shown in formula (2-1) or formula (2-2): The definitions of A, B, R1, R2, a and b are the same as those in formula (1).

3. The organic compound according to claim 1, characterized in that Having a structure as shown in any one of formulas (3-1), (3-2), (3-3), (3-4), (3-5), and (3-6): Wherein, the definitions of X, A, B, R1, R2, a and b are the same as in formula (1); Preferably, the organic compound has a structure as shown in any one of formulas (3-1), (3-2), (3-5) or (3-6); More preferably, in formulas (3-1), (3-2), (3-3), (3-4), (3-5), and (3-6), b is 0.

4. The organic compound according to claim 3, characterized in that The A is a structure of formula A: 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, indenocarbazolyl; The L3 is a single bond, and L1 and L2 are each independently selected from one of the following groups: phenylene, naphthylene, anthracene, phenanthrene, biphenylene, terphenylene, 9,9-dimethylfluorenylene, 9,9-diphenylfluorenylene, 9-methyl-9-phenylfluorenylene, spirofluorenylene, benzofluorenylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, carbazolylene, triazinylene, triazolylene, pyridylene, pyrimidylene, quinazolinylene, quinoxalinylene, benzimidazolylene, benzoindazolylene, benzocarbazolylene, benzofuranocarbazolylene, benzothiophenocarbazolylene, indolecarbazolylene, azadibenzothiophenylene, azadibenzofuranocarbazolylene; The substituents substituted in the above Ar1, Ar2, L1, and L2 are each independently selected from one of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C3-C10 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

5. The organic compound according to claim 3 or 4, characterized in that The B is a structure of formula B, wherein formula B is selected from one of the following substituted or unsubstituted structures: The substituent on the formula B is selected from one of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C3-C10 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, the formula B is selected from one of the following structures:

6. The organic compound according to claim 3, characterized in that The R1 and R2 are each independently selected from one of hydrogen, deuterium, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, R1 is selected from hydrogen, phenyl, biphenyl or naphthyl, and R2 is hydrogen.

7. The organic compound according to claim 1, characterized in that Selected from the following compounds:

8. Use of the organic compound according to any one of claims 1 to 7, wherein the use is as a functional material in an organic electronic device, wherein the organic electronic device is selected from an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper; Preferably, the organic compound is used as a light-emitting host material in an organic electroluminescent device.

9. An organic electroluminescent device, comprising a first electrode, a second electrode and one or more light-emitting functional layers inserted between the first electrode and the second electrode, characterized in that: The light-emitting functional layer contains the organic compound according to any one of claims 1 to 7; Preferably, the light-emitting functional layer includes a light-emitting layer and at least one of an electron blocking layer, a hole injection layer, a hole transport layer, and an electron transport layer. The light-emitting layer includes a main material and a doping material, and the main material includes the organic compound described in any one of claims 1 to 7.

10. An electronic device having a display screen or a display panel, characterized in that: The display screen or display panel adopts the organic electroluminescent device according to claim 9.

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