Heterocyclic organic compound and application thereof

Abstract

The invention provides a heterocyclic organic compound and application thereof.The heterocyclic organic compound is of a structure shown in the formula I. The heterocyclic organic compound comprises an oxa or thia fused heterocycle structure, a specific site is connected with a triazine structure, and through design of the molecular structure, the heterocyclic organic compound has excellent molecular axial property and molecular planarity and can be used for preparing a high-molecular-weight polymer. The glass-transition temperature Tg can be increased, and excellent molecular film-forming property, physical and thermodynamic properties and photoelectric properties are shown. The heterocyclic organic compound is used for the organic electroluminescent device, is suitable for being used as a main body material of a luminescent layer, can effectively improve the luminescent effect of the device, and especially enables the service life of the device to be obviously prolonged based on the improvement of Tg and molecular film-forming property.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a heterocyclic organic compound and application thereof. Background Art

[0002] In recent years, optoelectronic devices based on organic materials have developed rapidly and become a research hotspot in the field; examples of such optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLED devices have developed particularly rapidly and have achieved commercial success in the field of information display. OLED devices can provide highly saturated red, green, and blue colors. Full-color display devices made of OLED devices 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 multilayer thin film structure containing a variety of functionalized organic 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 materials (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] At present, OLED devices can be divided into fluorescent luminescence, phosphorescent luminescence, thermally excited delayed fluorescence and thermally excited sensitized fluorescence according to the luminescence mechanism. Common fluorescent luminophores mainly use singlet excitons generated when electrons and holes combine to emit light, and are still widely used in various OLED products. Some metal complexes (such as iridium complexes and platinum complexes) can simultaneously use triplet excitons and singlet excitons for luminescence, and are called phosphorescent luminophores. Their energy conversion efficiency can be increased by up to four times that of traditional fluorescent luminophores. Thermally excited delayed fluorescence (TADF) 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 luminophore by energy transfer, which can also achieve higher luminescence efficiency.

[0005] Although products using OLED technology have been commercialized, the device's lifespan, efficiency and other performance still need to be continuously improved to meet people's pursuit of high-quality display effects. Therefore, the field is in urgent need of developing more types of higher-performance organic materials, which can be applied to organic electroluminescent devices to make the devices have better luminous effects. Summary of the invention

[0006] In view of the deficiencies of the prior art, the object of the present invention is to provide a heterocyclic organic compound and its application. Through the design of molecular structure, the heterocyclic organic compound has excellent photoelectric properties and thermodynamic properties, and the glass transition temperature of the material is high. It is applied to organic electroluminescent devices, and is particularly suitable as the main material of the light-emitting layer, which can effectively improve the life of the device.

[0007] In order to achieve the purpose of the invention, the present invention adopts the following technical solutions:

[0008] In a first aspect, the present invention provides a heterocyclic organic compound having a structure as shown in Formula I:

[0009]

[0010] In formula I, X is S or O.

[0011] In Formula I, Y1, Y2, Y3, Y4, Y5, Y6, and X7 are each independently selected from CR 1 or N; multiple (e.g. 2, 3, 4, 5, 6, 7) CR 1 R 1 are the same or different groups.

[0012] R 1 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'substituted C6-C20 arylamino, unsubstituted or R'substituted C3-C20 heteroarylamino, unsubstituted or R'substituted C6-C20 aryloxy, unsubstituted or R'substituted C3-C20 heteroaryloxy, unsubstituted or R'substituted C6-C20 aryl, and unsubstituted or R'substituted C3-C20 heteroaryl;

[0013] In Formula I, X1, X2, X3, and X4 are each independently selected from CR 2 or N; multiple (e.g. 2, 3, 4) CR 2 R 2 are the same or different groups.

[0014] R 2Each is independently selected from any one of hydrogen, halogen, unsubstituted or R"-substituted C1-C20 straight or branched alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C2-C20 alkenyl, unsubstituted or R"-substituted C1-C20 alkoxy, unsubstituted or R"-substituted C1-C20 alkylsilyl, unsubstituted or R"-substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R"-substituted C6-C30 arylamino, unsubstituted or R"-substituted C3-C30 heteroarylamino, unsubstituted or R"-substituted C6-C30 aryloxy, unsubstituted or R"-substituted C3-C30 heteroaryloxy, unsubstituted or R"-substituted C6-C60 aryl, and unsubstituted or R"-substituted C3-C60 heteroaryl.

[0015] In Formula I, Ar1 and Ar2 are each independently selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group.

[0016] The substituents, R' and R" in Ar1 and Ar2 are independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. A combination of at least two.

[0017] 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 the same or different substituents. When the same expressions are mentioned below, they have the same meaning. Unless otherwise specified, the selection ranges of the substituted substituents, R', and R" are as shown above and will not be repeated.

[0018] In the present invention, the R' is not connected to the adjacent ring structure; the substituents and R" in Ar1 and Ar2 are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

[0019] In the present invention, "R" is independently not connected to the adjacent ring structure "means that R" is only connected to the C atom through a single bond; "R" is independently connected to the adjacent ring structure through a chemical bond to form a ring "means that R" is connected to the C atom through a chemical bond and is also connected to the adjacent ring through a chemical bond, thereby forming a fused ring structure. When the same description is involved below, it has the same meaning and will not be repeated one by one.

[0020] The heterocyclic organic compound provided by the present invention has a molecular structure shown in Formula I, wherein an aromatic condensed heterocyclic structure of oxygen or sulfur (X is S or O) is included, and a triazine structure is connected to a specific site of the condensed heterocyclic structure, so that the heterocyclic organic compound has excellent molecular axiality and molecular planarity, improves the glass transition temperature Tg, and exhibits excellent molecular film-forming properties, physical thermodynamic properties, and photoelectric properties. The heterocyclic organic compound is used for an organic electroluminescent device, is suitable as a main material of a light-emitting layer, can effectively improve the luminous effect of the device, and especially based on the improvement of Tg and molecular film-forming properties, the life of the device is significantly increased.

[0021] It should be noted that, in order to facilitate explanation, 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 essential reason for obtaining good performance is the optimized combination of the entire molecular structure, which is the result of the synergistic effect of each group, rather than the effect of a single group / feature.

[0022] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The following descriptions involving the same have the same meaning.

[0023] 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.

[0024] 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.

[0025] In the present invention, the expression of a ring structure crossed by “—” indicates that the connection site is at any position on the ring structure that can form a bond.

[0026] In the present invention, "-*" and "*" both represent the connection site of a group.

[0027] 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.

[0028] In the present invention, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0029] In the present invention, C1-C20 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0030] The C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0031] The C2-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0032] The C6-C20 can all be C6, C9, C10, C12, C14, C16, C18 or C20, etc.

[0033] 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.

[0034] 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.

[0035] The C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0036] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0037] In the present invention, the C1-C20 straight chain or branched alkyl group, preferably a C1-C16 straight chain or branched alkyl group, and further preferably a C1-C10 straight chain or branched alkyl group, illustratively includes but is 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, etc.

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

[0039] A specific example of the C1-C20 alkylsilyl group is a monovalent group in which at least one hydrogen in -SiH3 is replaced by the above-mentioned straight-chain or branched alkyl group; a specific example of the C1-C20 alkylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above-mentioned straight-chain or branched alkyl group.

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

[0041] The 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.

[0042] The C6-C60 aryl group (preferably a C6-C30 aryl group) and the C6-C20 aryl group include a monocyclic aryl group and a condensed aryl group; the monocyclic aryl group means that the group contains at least one phenyl group, and when the group 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, quaterphenyl, etc.; the condensed aryl group means that the group contains at least two aromatic rings, and the aromatic rings share two adjacent The groups in which carbon atoms are mutually fused include, but are not limited to, naphthyl, 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, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, perylene, It should be noted that the monocyclic aromatic groups and condensed aromatic groups connected by a single bond also belong to the scope of aromatic groups, such as phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenylnaphthylphenyl, etc.

[0043] The C3-C60 heteroaryl (preferably C6-C30 heteroaryl) and the C3-C20 heteroaryl include monocyclic heteroaryl or condensed ring heteroaryl. The monocyclic heteroaryl means that the molecule contains at least one heteroaryl. When the molecule contains one 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, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, 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, 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, dibenzofuranylphenyl, dibenzofuranylnaphthyl, dibenzothienylphenyl, dibenzothienylnaphthyl, and the like.

[0044] In the present invention, the C6-C30 aryloxy group and C6-C20 aryloxy group are monovalent groups formed by connecting the above-mentioned aryl groups and O, and the C3-C30 heteroaryloxy group and C3-C20 heteroaryloxy group are monovalent groups formed by connecting the above-mentioned heteroaryl groups and O.

[0045] In the present invention, specific examples of the C6-C60 arylamino, C6-C30 arylamino, and C6-C20 arylamino are monovalent groups in which at least one hydrogen in -NH2 is replaced by the above aryl groups, including but not limited to phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, biphenylamino, etc. Specific examples of the C3-C60 heteroarylamino, C3-C30 heteroarylamino, and C3-C20 heteroarylamino are monovalent groups in which at least one hydrogen in -NH2 is replaced by the above heteroaryl groups, including but not limited to pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0046] Preferably, at most 3 (e.g. 0, 1, 2 or 3) of Y1, Y2, Y3, Y4, Y5, Y6 and X7 are N.

[0047] Preferably, at most one (0 or 1) of Y1 and X7 is N; and / or at most one (0 or 1) of Y2 and Y3 is N; and / or at most one (0 or 1) of Y4, Y5 and Y6 is N.

[0048] Preferably, Y1, Y2, Y3, Y4, Y5, Y6, and X7 are each independently selected from CR 1 .

[0049] Preferably, the R 1 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, unsubstituted or R'-substituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, cyano, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, unsubstituted or R'-substituted C3-C20 heteroaryl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.), and is more preferably hydrogen.

[0050] Preferably, at most one (0 or 1) of X1, X2, X3 and X4 is N.

[0051] Preferably, X1, X2, X3, and X4 are each independently selected from CR 2 .

[0052] Preferably, the R 2 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R" substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, unsubstituted or R" substituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, cyano, unsubstituted or R" substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and unsubstituted or R" substituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and is more preferably hydrogen.

[0053] Preferably, the heterocyclic organic compound has a structure as shown in Formula II:

[0054]

[0055] In formula II, X, Ar1, and Ar2 have the same defined ranges as those in formula I.

[0056] Preferably, X is O.

[0057] Preferably, Ar1 and Ar2 are each independently selected from any one of substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C25, C28, etc.) aryl groups and substituted or unsubstituted C3-C30 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C25, C28, etc.) heteroaryl groups.

[0058] Preferably, Ar1 and Ar2 are each independently selected from any one of the following substituted or unsubstituted groups:

[0059] Wherein, -* represents the attachment site of the group.

[0060] Z is selected from O, S, CR 11 R 12 or NR 13 Any one of .

[0061] R 11 , R 12 , R 13 Each is independently selected from any one or a combination of at least two of a C1-C20 straight or branched alkyl group, a C3-C20 cycloalkyl group, a C2-C20 alkenyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group; 11 and R 12 Not connected or connected to form a ring through chemical bonds.

[0062] Preferably, Z is selected from O, S or CR 11 R 12 Any one of .

[0063] Preferably, the R 11 , R 12 Each is independently selected from any one of C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, further preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl, further preferably methyl or phenyl.

[0064] Preferably, the substituents substituted in Ar1 and Ar2 are each independently selected from halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C any one or a combination of at least two of a C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl group, a C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl group, and more preferably a cyano group, a methyl group, a tert-butyl group, an isopropyl group, a cycloalkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, a dimethylfluorenyl group, Any one or a combination of at least two of the groups.

[0065] Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups:

[0066]

[0067] Wherein, -* represents the attachment site of the group.

[0068] Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups:

[0069]

[0070] -* represents the attachment site of the group.

[0071] In a preferred technical solution, Ar1 and Ar2 are each independently selected from Any one of the above, preferably -* represents the attachment site of the group.

[0072] Preferably, the heterocyclic organic compound has a structure shown in any one of N1-N144 below:

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] In a second aspect, the present invention provides a use of the heterocyclic organic compound as described in the first aspect, wherein the heterocyclic organic compound is used in an organic electronic device.

[0086] Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner or electronic paper.

[0087] Preferably, the heterocyclic organic compound is applied to an organic electroluminescent device, and more preferably applied to a red organic electroluminescent device.

[0088] Preferably, the heterocyclic organic compound is used as a light-emitting layer material in an organic electroluminescent device, and more preferably as a host material of the light-emitting layer.

[0089] In a third aspect, the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one heterocyclic organic compound as described in the first aspect.

[0090] Preferably, the organic layer comprises at least one heterocyclic organic compound having a structure represented by N1-N144.

[0091] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one heterocyclic organic compound as described in the first aspect.

[0092] Preferably, the light-emitting layer comprises a host material and a doping material, and the host material comprises at least one heterocyclic organic compound as described in the first aspect.

[0093] As a preferred technical solution of the present invention, the heterocyclic organic compound is used as the main material of the light-emitting layer, which is an electronic main material with a low triplet energy difference, and is particularly suitable as the main material of the red light-emitting layer, and can improve the service life of the organic electroluminescent device.

[0094] Preferably, the host material comprises a combination of a first host material and a second host material, and the first host material comprises at least one heterocyclic organic compound as described in the first aspect.

[0095] Preferably, the second host material has a structure as shown in Formula III:

[0096]

[0097] Wherein, Ar3, Ar4, and Ar5 are each independently selected from any one of a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; Ar3, Ar4, and Ar5 are not connected or are connected to form a ring through chemical bonds.

[0098] The substituted substituents in Ar3, Ar4 and Ar5 are each independently selected from any one of halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-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; in Ar3, Ar4 and Ar5, the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

[0099] Preferably, the organic compound is used as the first host material in a dual-host device. It has excellent electron transport properties and is compounded with a second host material of aromatic amines to effectively regulate and achieve a transport balance between holes and electrons, further improve the luminescence effect of the device, increase efficiency and life, and give the device better overall performance.

[0100] Preferably, the mass ratio of the first host material to the second host material is (0.1-2):1, for example, it can be 0.2:1, 0.3:1, 0.4:1, 0.5:1, 0.6:1, 0.7:1, 0.8:1, 0.9:1, 1:1, 1.1:1, 1.2:1, 1.3:1, 1.4:1, 1.5:1, 1.6:1, 1.7:1, 1.8:1 or 1.9:1, and is further preferably (0.5-1.5):1.

[0101] Preferably, the doping material (also called "dye", "luminescent dye", "guest material") is a phosphorescent doping material.

[0102] Preferably, based on the mass of the main material being 100%, the mass of the doping material in the light-emitting layer is 0.1-10%, for example, 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8% or 9%.

[0103] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0104] Preferably, the hole transport region includes any one of a hole injection layer, a hole transport layer, and an electron blocking layer, or a combination of at least two of them.

[0105] Preferably, the electron transport region includes any one of an electron injection layer, an electron transport layer, and a hole blocking layer, or a combination of at least two of them.

[0106] In a preferred technical solution, the organic electroluminescent device (OLED device) comprises a first electrode, a second electrode, and an organic layer between the electrodes. The organic layer can be divided into multiple regions, for example, a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer comprises at least one heterocyclic organic compound as described in the first aspect, and further preferably comprises at least one heterocyclic organic compound with a structure shown in N1-N144.

[0107] In a preferred technical solution, the organic electroluminescent device includes a first electrode, a plurality of light-emitting functional layers (organic layers) and a second electrode arranged in sequence; the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer arranged in sequence, and the hole injection layer is in contact with the first electrode (anode). The organic layer (preferably the light-emitting layer) contains at least one heterocyclic organic compound as described in the first aspect, and further preferably contains at least one heterocyclic organic compound having a structure shown by N1-N144.

[0108] In a preferred technical solution, a substrate can be used below the first electrode or above the second electrode. The substrate is glass or polymer material with excellent mechanical strength, thermal stability, water resistance and transparency. In addition, a thin film transistor (TFT) can also be provided on the substrate used as a display.

[0109] 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.

[0110] The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer can be an organic small molecule, an organic macromolecule or a polymer, and a combination thereof.

[0111] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0112] 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 the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0113]

[0114]

[0115]

[0116] 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.

[0117]

[0118] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra and 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.

[0119] 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.

[0120] In the preferred technical solution of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The main material of the light-emitting layer includes a combination of a first main material and a second main material, wherein the first main material includes at least one heterocyclic organic compound described in Formula I.

[0121] The second host material has Specifically, the second host material can be selected from, but not limited to, one or more combinations of the following specific compounds H1-H28.

[0122]

[0123]

[0124]

[0125] 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.

[0126]

[0127]

[0128] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be one or more compounds of HT-1 to HT-51, but is not limited thereto.

[0129] The OLED organic 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 multi-layer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0130] 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.

[0131]

[0132]

[0133]

[0134]

[0135] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be one or more compounds of the above ET-1 to ET-73, but is not limited thereto.

[0136] 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, Li, Ca, Mg, and Yb.

[0137] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0138] Preferably, the display device includes a display screen or a display panel.

[0139] The present invention also provides an electronic device, which includes the above-mentioned display device.

[0140] Compared with the prior art, the present invention has the following beneficial effects:

[0141] The heterocyclic organic compound provided by the present invention has a structure shown in Formula I, wherein an oxygen- or sulfur-containing fused heterocyclic structure is included, and a triazine structure is connected to a specific site thereof. Through the design of the molecular structure, the heterocyclic organic compound has excellent molecular axiality and molecular planarity, can improve the glass transition temperature, and exhibits excellent molecular film-forming properties, physical thermodynamic properties, and photoelectric properties. The heterocyclic organic compound is used in an organic electroluminescent device, is suitable as a main material of a light-emitting layer, can effectively improve the luminous effect of the device, and especially significantly prolongs the life of the device based on the improvement of Tg and molecular film-forming properties. BRIEF DESCRIPTION OF THE DRAWINGS

[0142] Figure 1 is the X-ray diffraction pattern of the intermediate M1-3 obtained in Preparation Example 1;

[0143] Figure 2 The molecular structure diagram of the heterocyclic organic compound N25 provided by the present invention;

[0144] Figure 3 This is the molecular structure diagram of the comparative compound Ref2. DETAILED DESCRIPTION

[0145] 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.

[0146] The heterocyclic organic compound represented by Formula I of the present invention can be synthesized by organic synthesis methods known in the art. An exemplary synthesis route is given below, but those skilled in the art can also obtain it by other methods known in the art.

[0147] In a specific embodiment, the heterocyclic organic compound can be prepared by the following synthetic route:

[0148] Wherein, X, Y1, Y4, Y5, Y6, X7, X1, X2, X3, X4, Ar1, Ar2 have the same definitions as in Formula I; U1, U2 are each independently selected from Hal1 is selected from halogen, preferably Cl, Br or I.

[0149] In a specific embodiment, the intermediate A1 reacts with (methoxymethyl)triphenylphosphonium chloride to generate intermediate A2.

[0150] In a specific embodiment, the aforementioned raw material S can be purchased or prepared by the following exemplary synthetic route:

[0151] Hal2 is selected from halogen, preferably Cl, Br or I.

[0152] The specific preparation method of the heterocyclic organic compound of the present invention will be described in detail below using multiple preparation examples and synthesis examples as examples. However, the preparation method of the heterocyclic organic compound of the structure represented by Formula I of the present invention includes but is not limited to the synthesis method in the specific embodiment. Those skilled in the art can also make routine adjustments to the preparation method according to actual needs. The heterocyclic organic compound of the structure represented by Formula I synthesized by other methods also belongs to the protection scope of the present invention.

[0153] The following preparation examples and synthesis examples of the present invention provide exemplary specific synthesis methods of representative compounds. The solvents and reagents used in the synthesis examples can be purchased or customized from the chemical product market. The mass spectrometry characterization data (MS) of the intermediates and target compounds in the present invention are obtained by mass spectrometer testing; the reaction process and end point are detected by gas thin layer chromatography (TLC).

[0154] The compounds of the synthesis methods not mentioned in the present invention are all raw materials obtained from commercial channels, or are prepared by themselves according to known methods using these raw materials.

[0155] Preparation Example 1: Synthesis of Intermediate M1

[0156]

[0157] Dibenzofuran-2-boric acid (0.8 mol), 2-bromo-5-chloro-benzaldehyde (0.8 mol), potassium carbonate (1 mol), tetrakis(triphenylphosphine)palladium (0.01 mol), water (300 mL) and dioxane (1500 mL) were added to a reaction bottle, heated to 90°C for 6 h, and the reaction was complete under TLC monitoring. Water and dichloromethane were added for extraction, and the organic phase was separated and concentrated to obtain intermediate M1-1.

[0158] Add intermediate M1-1 (0.7 mol), (methoxymethyl) triphenylphosphonium chloride (0.8 mol), and tetrahydrofuran (2000 mL) to the reaction flask, cool to 0°C while stirring, and gradually add sodium tert-butoxide (1 mol) in batches. The temperature during the addition process is not higher than 5°C. After the addition is completed, react at room temperature for 2 hours. TLC monitors the reaction to be complete. Add brine and ethyl acetate for extraction, and concentrate the organic phase to obtain intermediate M1-2.

[0159] The intermediate M1-2 (0.5 mol) was added to dichloromethane (1500 mL), cooled to -20°C with stirring, and methanesulfonic acid (1 mol) was slowly added dropwise. After the addition was complete, the reaction was kept warm for 1 h. The reaction was monitored to be complete by TLC. After the solvent was directly concentrated, the content of M1-3 was 85% and the content of M1-3-1 was 15% by high performance liquid chromatography (HPLC). The intermediate M1-3 was recrystallized from toluene / ethanol with a purity greater than 99.5%.

[0160] The intermediate M1-3 was detected by X-ray diffractometer (XRD, model Synergy-R, manufacturer Rigaku), and the obtained X-ray diffraction pattern is as follows: Figure 1 As shown, it is shown that the structure of the prepared intermediate M1-3 is correct.

[0161] The intermediate M1-3 (0.3 mol), pinacol borate (0.4 mol), potassium acetate (0.5 mol), 1,1-bis(diphenylphosphino)ferrocenepalladium dichloride (0.005 mol) and dioxane (1500 mL) were added to a reaction bottle, heated to 90°C for 6 h, and the reaction was complete under TLC monitoring. Water and dichloromethane were added for extraction, and the organic phase was separated and concentrated to obtain the intermediate M1 (MS: 395.2).

[0162] Preparation Example 2: Synthesis of Intermediate M2

[0163] The synthesis method of intermediate M2 is similar to that of intermediate M1, except that the dibenzofuran-2-boric acid in Preparation Example 1 is replaced with an equimolar amount of dibenzothiophene-2-boric acid. The other materials, synthesis steps and parameters are the same as those in Preparation Example 1 to obtain intermediate M2.

[0164] Most of the triazine raw materials in the present invention can be directly obtained from the market. Those that cannot be directly obtained are obtained by simple customized synthesis from cooperative raw material manufacturers. The present invention exemplarily provides the synthesis methods of some triazine raw materials.

[0165] Preparation Example 3: Synthesis of Raw Material S1

[0166]

[0167] 2-(3- 4-Dichloro-6-diphenyl-1,3,5-triazine (0.02 mol), potassium carbonate (0.024 mol), tetrakis(triphenylphosphine)palladium (0.0002 mol), water (20 mL) and dioxane (200 mL) were added into a reaction bottle and heated to 80°C for 4 h. The reaction was completed under the control of TLC. After cooling, dichloromethane and water were added to extract the liquid. The organic phase was concentrated, washed with ethanol and filtered to obtain the target product S1 (MS: 418.1).

[0168] Preparation Example 4: Synthesis of Raw Material S2

[0169]

[0170] 1,3,2-Dioxaborane-4,4,5,5-tetramethyl-2-(1,1':3',1"-triphenyl)-4'-yl (raw material S2-1, 0.02 mol), 2,4-dichloro-6-diphenyl-1,3,5-triazine (0.02 mol), potassium carbonate (0.024 mol), tetrakis(triphenylphosphine)palladium (0.0002 mol), water (20 mL) and dioxane (200 mL) were added to a reaction bottle, heated to 80°C for 4 h, and the reaction was completed under TLC monitoring. After cooling, dichloromethane and water were added to extract the liquid. The organic phase was concentrated, washed with ethanol, and filtered to obtain the target product S2 (MS: 420.1).

[0171] Preparation Example 5: Synthesis of Raw Material S3

[0172]

[0173] 1-Bromo-3-chloronaphthalene (0.05 mol), dibenzofuran-2-boric acid (0.05 mol), potassium carbonate (0.024 mol), tetrakis(triphenylphosphine)palladium (0.0005 mol), water (20 mL) and dioxane (200 mL) were added to a reaction bottle and heated to 80°C for 4 h. The reaction was completed under the control of TLC. After cooling, dichloromethane and water were added to extract the liquid. The organic phase was concentrated, washed with ethanol and filtered to obtain intermediate S3-1.

[0174] The intermediate S3-1 (0.03 mol), pinacol borate (0.04 mol), potassium acetate (0.05 mol), 1,1-bis(diphenylphosphino)ferrocenepalladium dichloride (0.003 mol) and dioxane (200 mL) were added to a reaction bottle, heated to 100 ° C for 6 h, and the reaction was completed under the control of TLC. Water and dichloromethane were added for extraction. The organic phase was separated and concentrated to obtain the intermediate S3-2.

[0175] The intermediate S3-2 (0.02 mol), 2,4-dichloro-6-diphenyl-1,3,5-triazine (0.02 mol), potassium carbonate (0.024 mol), tetrakis(triphenylphosphine)palladium (0.0002 mol), water (20 mL) and dioxane (200 mL) were added to a reaction bottle, heated to 80°C for 4 h, and the reaction was completed under the monitoring of TLC. After cooling, dichloromethane and water were added to extract the liquid. The organic phase was concentrated, washed with ethanol, and filtered to obtain the target product S3 (MS: 484.1).

[0176] Synthesis Example 1: Synthesis of Heterocyclic Organic Compound N1

[0177]

[0178] The intermediate M1 (0.02 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (0.02 mol), potassium carbonate (0.024 mol), tetrakis(triphenylphosphine)palladium (0.0002 mol), water (20 mL) and dioxane (200 mL) were added to a reaction bottle, heated to 100°C for 4 h, and the reaction was complete under the monitoring of TLC. After cooling, a large amount of solid precipitated. After filtration, the target product N1 (MS: 500.2) was obtained by recrystallization from xylene.

[0179] Synthesis Example 2: Synthesis of Heterocyclic Organic Compound N4

[0180]

[0181] The intermediate M1 (0.02 mol), 2-chloro-4,6-di(naphthalene-2-yl)-1,3,5-triazine (0.02 mol), potassium carbonate (0.024 mol), tetrakis(triphenylphosphine)palladium (0.0002 mol), water (20 mL) and dioxane (200 mL) were added to a reaction bottle, heated to 100°C for 4 h, and the reaction was complete under the monitoring of TLC. After cooling, a large amount of solid precipitated. After filtration, the target product N4 (MS: 600.2) was obtained by recrystallization from xylene.

[0182] Synthesis Example 3: Synthesis of Heterocyclic Organic Compound N53

[0183] The synthesis method of N53 is similar to that of N1, except that the 2-chloro-4,6-diphenyl-1,3,5-triazine in Synthesis Example 1 is replaced by an equimolar amount of raw material S1 (Preparation Example 3), and other materials, synthesis steps and parameters are the same as those in Synthesis Example 1 to obtain the target product N53 (MS: 650.2).

[0184] Synthesis Example 4: Synthesis of Heterocyclic Organic Compound N69

[0185] The synthesis method of N69 is similar to that of N1, except that the 2-chloro-4,6-diphenyl-1,3,5-triazine in Synthesis Example 1 is replaced by an equimolar amount of raw material S2 (Preparation Example 4), and other materials, synthesis steps and parameters are the same as those in Synthesis Example 1 to obtain the target product N69 (MS: 652.2).

[0186] Synthesis Example 5: Synthesis of Heterocyclic Organic Compound N88

[0187] The synthesis method of N88 is similar to that of N1, except that the intermediate M1 in Synthesis Example 1 is replaced by an equimolar amount of intermediate M2, and 2-chloro-4,6-diphenyl-1,3,5-triazine is replaced by an equimolar amount of raw material S3 (Preparation Example 5). Other materials, synthesis steps and parameters are the same as those in Synthesis Example 1, and the target product N88 (MS: 732.2) is obtained.

[0188] Other compounds in the present invention can be synthesized by the above Suzuki method, except that different intermediates (M1 or M2) and / or triazine raw materials are replaced, which are not listed one by one.

[0189] The present invention illustratively provides a specific synthesis method for all intermediates (M1, M2), as well as an example of synthesizing the compounds of the present invention by Suzuki reaction of some intermediates with triazine raw materials. For other compounds for which no specific synthesis method is given, they are also prepared by similar methods, and only need to replace the raw materials to obtain them. They will not be described in detail here, or those skilled in the art can also prepare them by other methods in the prior art.

[0190] Device Example 1

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

[0192] (1) a glass substrate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone / ethanol mixed solvent, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0193] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, vacuum evaporating a mixture of compound HT-29:HI-1 (97 / 3, w / w) on the above anode layer as a hole injection layer, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 10 nm;

[0194] (3) vacuum evaporating compound HT-29 on the hole injection layer as a hole transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 60 nm;

[0195] (4) vacuum evaporating compound HT-37 on the hole transport layer as an electron blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 60 nm;

[0196] (5) vacuum evaporating a light-emitting layer on the electron blocking layer, wherein the light-emitting layer includes a main material and a doping material (dye, RPD-18), and the mass ratio (w / w) of the main material to the doping material is 100:3; the main material is a mixture of a first main material (the heterocyclic organic compound N1 provided by the present invention) and a second main material (compound H13) (the mass ratio of N1 to H13 is 1:1); the evaporation is performed by a dual-source co-evaporation method, the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 40 nm;

[0197] (6) vacuum evaporating compound ET-17 on the light-emitting layer as a hole blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0198] (7) vacuum evaporating a mixture of compounds ET-66:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 25 nm;

[0199] (8) Vacuum evaporation of LiF as an electron injection layer on the electron transport layer at a rate of 0.1 nm / s and a thickness of 1 nm;

[0200] (9) Vacuum evaporating metal Al with a thickness of 150 nm on the electron injection layer as a cathode at a evaporation rate of 1 nm / s to obtain the organic electroluminescent device.

[0201] Device Examples 2-16, Device Comparative Examples 1-4

[0202] An organic electroluminescent device, which differs from device embodiment 1 only in that the main materials of the light-emitting layer are the compounds shown in Table 1, and the mass ratio of the first main material to the second main material is 1:1; other layers, thicknesses, materials and preparation methods are the same as those of device embodiment 1.

[0203] The structure of the host material in the device comparative example is as follows:

[0204]

[0205] The performance test of the organic electroluminescent devices provided in device examples 1-16 and device comparative examples 1-4 was performed, and the specific method was as follows:

[0206] (1) Lifespan

[0207] The brightness of the organic electroluminescent device was measured using a brightness meter from 10000cd / m 2 Attenuation to 9700cd / m 2 The time taken is recorded as the LT97 life test value of the device;

[0208] The LT97 life test value of the device comparative example 1 is recorded as 1, and the ratio (relative life) of the LT97 life test values ​​of other devices to the LT97 life test value of the device comparative example 1 is calculated.

[0209] (2) Glass transition temperature Tg

[0210] The Tg was measured using a differential scanning calorimeter (DSC). The specific method was as follows: the first main material to be tested was packaged in an aluminum crucible, heated to 320°C at a rate of 20°C / min in a nitrogen atmosphere, cooled to 30°C, and then heated for a second time at a rate of 10°C / min, and the glass transition temperature Tg was recorded.

[0211] The specific results are shown in Table 1:

[0212] Table 1

[0213] First main material Second main material First main material Tg (℃) life Device Example 1 N1 H13 120 1.7 Device Example 2 N4 H13 132 1.9 Device Example 3 N5 H13 128 1.6 Device Example 4 N17 H13 125 1.7 Device Example 5 N25 H13 126 1.9 Device Example 6 N32 H13 127 1.8 Device Example 7 N43 H13 130 1.4 Device Example 8 N53 H13 139 2.2 Device Example 9 N69 H13 126 1.5 Device Example 10 N88 H13 131 1.7 Device Example 11 N97 H13 128 1.7 Device Example 12 N102 H13 129 1.6 Device Example 13 N107 H13 126 1.4 Device Example 14 N135 H13 122 1.6 Device Example 15 N138 H13 127 1.3 Device Example 16 N144 H13 135 2.1 Device Comparative Example 1 Ref-1 H13 126 1 Device Comparison Example 2 Ref-2 H13 113 1.3 Device Comparison Example 3 Ref-3 H13 110 1.2 Device Comparison Example 4 Ref-4 H13 102 0.9

[0214] Combined with the data in Table 1, it can be seen that the heterocyclic organic compound provided by the present invention has a relatively high glass transition temperature, Tg ≥ 120°C, which can be 120-139°C, and has excellent molecular film-forming properties, physical thermodynamic properties and photoelectric properties. As the main material of the light-emitting layer of an organic electroluminescent device, it can significantly extend the life of the device based on the improvement of Tg and molecular film-forming properties.

[0215] In order to improve the glass transition temperature and verify the dihedral angle of the material, the present invention uses Gaussian16 software to optimize the ground state structure of comparative examples Ref2 and N25 at the calculation level of cam-b3lyp / 6-31g*, and obtains the calculated value, which proves the idea of ​​molecular design of the present invention. Figure 2 The molecular structure diagram of the heterocyclic organic compound N25 provided by the present invention is shown in FIG. Figure 3 For the molecular structure diagram of the comparative compound Ref2, Figure 2 and Figure 3 The structure shows that the dihedral angle of N25 is 1°, which is almost a planar structure, and the dihedral angle of Ref2 is 35°, and the molecule is obviously twisted; the heterocyclic organic compound of the present invention has a specific molecular dihedral angle and spatial configuration, which gives it a higher glass transition temperature and better thermal stability.

[0216] By comparing the light-emitting layer materials and effect data of device embodiments 1-16 of the present invention with device comparison examples 1-4, it can be seen that the lifespan of device embodiments 1-16 using the heterocyclic organic compound of the present invention is significantly better than that of the comparative compound. The reason is that the heterocyclic organic compound differs from Ref-2 only in the substitution site, but the compound of the present invention exhibits a higher glass transition temperature, which is also a strategy for material design of the present invention. The specific substitution site of the present invention brings about different dihedral angles of the molecular structure and different overall molecular configuration, giving the heterocyclic organic compound a higher rigid structure, thereby having a higher glass transition temperature and therefore having higher thermal stability. The increased rigidity also affects the film-forming property of the molecule in the light-emitting layer. The compound of the present invention has a better planar film structure, which makes its carrier transport more balanced and therefore has a higher lifespan. Ref-1 has a higher glass transition temperature than some compounds in the device embodiment. This is because there is a bridge structure between the triazine structure and the oxygen-containing fused ring structure of Ref-1, and the inherent thermodynamic properties change due to the increase in the overall molecular weight. It cannot be compared under the same conditions, but the device life of the present invention is much longer than the device using Ref-1. The reason is that the connection site of Ref-1 is different. It connects the triazine group at the 12 site of the fused ring structure of phenylene furan. Due to the steric effect of the molecule, the molecular spatial structure is distorted, which affects the overall electron mobility, causing the luminescent recombination position of the molecule in the luminescent layer to change. Obviously, due to the imbalance of carriers, the luminescent recombination interface of Ref-1 is more biased towards the transport layer, resulting in its short life. In Ref-3, the dibenzofuran group is connected to the triazine structure, which is different from the parent core structure of the material of the present invention. Obviously, the parent core phenylene furan of the material of the present invention has higher molecular rigidity and a larger planar structure than dibenzofuran, and therefore has better thermodynamic properties and better electron mobility.

[0217] The applicant declares that the present invention illustrates the heterocyclic organic compound and its application through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned process steps, that is, it does not mean that the present invention must rely on the above-mentioned process steps to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of the raw materials selected by 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. A heterocyclic organic compound, characterized in that The heterocyclic organic compound has a structure as shown in Formula I: Wherein, X is S or O; Y1, Y2, Y3, Y4, Y5, Y6, and X7 are each independently selected from CR 1 or N; R 1 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'substituted C6-C20 arylamino, unsubstituted or R'substituted C3-C20 heteroarylamino, unsubstituted or R'substituted C6-C20 aryloxy, unsubstituted or R'substituted C3-C20 heteroaryloxy, unsubstituted or R'substituted C6-C20 aryl, and unsubstituted or R'substituted C3-C20 heteroaryl; X1, X2, X3, and X4 are each independently selected from CR 2 or N; R 2 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R"-substituted C1-C20 straight or branched alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C2-C20 alkenyl, unsubstituted or R"-substituted C1-C20 alkoxy, unsubstituted or R"-substituted C1-C20 alkylsilyl, unsubstituted or R"-substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R"-substituted C6-C30 arylamino, unsubstituted or R"-substituted C3-C30 heteroarylamino, unsubstituted or R"-substituted C6-C30 aryloxy, unsubstituted or R"-substituted C3-C30 heteroaryloxy, unsubstituted or R"-substituted C6-C60 aryl, and unsubstituted or R"-substituted C3-C60 heteroaryl; Ar1 and Ar2 are each independently selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group; The substituents, R', and R" in Ar1 and Ar2 are each independently selected from any one or a combination of at least two of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; The R' is not connected to the adjacent ring structure; the substituted substituents and R" in Ar1 and Ar2 are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

2. The heterocyclic organic compound according to claim 1, characterized in that The Y1, Y2, Y3, Y4, Y5, Y6, and X7 are each independently selected from CR 1 ; Preferably, the R 1 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R'-substituted C1-C10 straight or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, cyano, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl, and is more preferably hydrogen.

3. The heterocyclic organic compound according to claim 1, characterized in that The X1, X2, X3, and X4 are each independently selected from CR 2 ; Preferably, the R 2 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R"-substituted C1-C10 straight or branched alkyl, unsubstituted or R"-substituted C3-C10 cycloalkyl, cyano, unsubstituted or R"-substituted C6-C20 aryl, and unsubstituted or R"-substituted C3-C20 heteroaryl, and is more preferably hydrogen.

4. The heterocyclic organic compound according to claim 1, characterized in that The heterocyclic organic compound has a structure as shown in Formula II: Wherein, X, Ar1, and Ar2 have the same defined ranges as those in Formula I.

5. The heterocyclic organic compound according to claim 1 or 4, characterized in that The X is O.

6. The heterocyclic organic compound according to claim 1 or 4, characterized in that The Ar1 and Ar2 are each independently selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group; Preferably, Ar1 and Ar2 are each independently selected from any one of the following substituted or unsubstituted groups: Wherein, -* represents the attachment site of the group; Z is selected from O, S, CR 11 R 12 or NR 13 Any of the following: R 11 , R 12 , R 13 Each is independently selected from any one or a combination of at least two of a C1-C20 straight or branched alkyl group, a C3-C20 cycloalkyl group, a C2-C20 alkenyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group; 11 and R 12 Not connected or connected into rings by chemical bonds; Preferably, Z is selected from O, S or CR 11 R 12 Any of the following: Preferably, the R 11 , R 12 Each is independently selected from any one of C1-C10 straight or branched alkyl, C6-C20 aryl; Preferably, the substituents substituted in Ar1 and Ar2 are each independently selected from any one or a combination of at least two of halogen, cyano, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; More preferably, the substituents substituted in Ar1 and Ar2 are each independently selected from phenyl, naphthyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, One of the following: fluorenyl and fluorenyl.

7. The heterocyclic organic compound according to claim 6, characterized in that The Ar1 and Ar2 are each independently selected from any one of the following groups: Wherein, -* represents the attachment site of the group; Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups: -* represents the attachment site of the group.

8. The heterocyclic organic compound according to claim 6, characterized in that The Ar1 and Ar2 are each independently selected from Any one of the above, preferably -* represents the attachment site of the group.

9. The heterocyclic organic compound according to claim 1, characterized in that The heterocyclic organic compound has a structure shown in any one of the following N1-N144:

10. Use of a heterocyclic organic compound as claimed in any one of claims 1 to 9, characterized in that: The heterocyclic organic compound is applied to organic electronic devices; Preferably, the organic electronic device comprises an organic electroluminescent device; Preferably, the heterocyclic organic compound is used as a light-emitting layer material in an organic electroluminescent device.

11. 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 heterocyclic organic compound according to any one of claims 1 to 9; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one heterocyclic organic compound as described in any one of claims 1 to 9; Preferably, the light-emitting layer comprises a host material and a doping material, and the host material comprises at least one heterocyclic organic compound as claimed in any one of claims 1 to 9.

12. The organic electroluminescent device according to claim 11, characterized in that: The host material comprises a combination of a first host material and a second host material, wherein the first host material comprises at least one heterocyclic organic compound as claimed in any one of claims 1 to 9; Preferably, the second host material has a structure as shown in Formula III: Wherein, Ar3, Ar4, and Ar5 are each independently selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group; Ar3, Ar4, and Ar5 are not connected or are connected to form a ring through a chemical bond; The substituted substituents in Ar3, Ar4 and Ar5 are each independently selected from any one or a combination of at least two of halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-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; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds; Preferably, the mass ratio of the first host material to the second host material is (0.1-2):

1.

13. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 11 or 12.

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