Organic compound and application thereof, and organic electroluminescent device containing organic compound

Abstract

The invention provides an organic compound and application thereof, and an organic electroluminescent device comprising the organic compound, the organic compound has a structure as shown in a formula I. Through the design of a molecular structure, the organic compound has excellent carrier injection transmission performance and electron injection transmission performance; an excellent balance effect is achieved between electron injection and transmission performance and energy transfer, and meanwhile, proper molecular weight and excellent thermal stability are achieved. The organic compound is excellent in photoelectric property, is used for the organic electroluminescent device, and can effectively improve the luminous efficiency of the device, reduce the voltage and prolong the service life of the device.

Description

Technical Field

[0001] The invention belongs to the technical field of organic light-emitting materials, and in particular relates to an organic compound and application thereof, and an organic electroluminescent device containing the organic compound. Background Art

[0002] In recent years, optoelectronic devices based on organic materials have developed rapidly and become a hot topic in the field. Examples of such 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 bright colors, thinness, softness, and flexibility.

[0003] OLED devices include two electrodes and a multilayer organic film between the two electrodes. The core of the OLED device is a multilayer organic film structure containing a variety of organic functional materials. Common organic functional 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). When the power is turned on, electrons and holes are injected and transported to the luminescent area 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 compared with traditional fluorescent luminophores. Thermally excited delayed fluorescence (TADF) technology can effectively utilize triplet excitons to achieve higher luminescence efficiency without using metal complexes by promoting the transformation of triplet excitons to singlet excitons. 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 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 display effects. Therefore, the field is in urgent need of developing more types of higher performance organic materials so that the organic electroluminescent devices using them have higher luminous efficiency, lower driving voltage and longer service life. Summary of the invention

[0006] In view of the deficiencies in the prior art, the purpose of the present invention is to provide an organic compound and its application, and an organic electroluminescent device containing the same. Through the design of the molecular structure, the organic compound has excellent photoelectric properties. Its application in organic electroluminescent devices can effectively improve the life and luminous efficiency of the device and reduce the driving voltage.

[0007] To achieve this object, the present invention adopts the following technical solutions:

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

[0009]

[0010] In formula I, one of A1 and A2 is a group represented by formula II, and the other is a group represented by formula III:

[0011]

[0012] -* represents the attachment site of the group.

[0013] R1 is selected from any one of hydrogen, cyano, halogen, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, C1-C30 alkoxy, and substituted or unsubstituted C3-C60 heteroaryl.

[0014] R2, R3, and R4 are each independently selected from any one of halogen, cyano, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0015] a, b, c represent the number of substituents R2, R4, R3 respectively. a is selected from an integer of 0-5, for example, 0, 1, 2, 3, 4 or 5. b is selected from an integer of 0-7, for example, 0, 1, 2, 3, 4, 5, 6 or 7. c is selected from an integer of 0-4, for example, 0, 1, 2, 3 or 4.

[0016] It should be noted that when a≥2, multiple substituents R2 are the same or different groups; when b≥2, multiple substituents R4 are the same or different groups; when c≥2, multiple substituents R3 are the same or different groups.

[0017] X1, X2, and X3 are each independently selected from any one of CR5 and N, and at least one of them is N.

[0018] R5 is each independently selected from any one of hydrogen, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0019] L1, L2, and L3 are each independently selected from any one of a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group; when L1 is a single bond, it represents that Ar1 and the six-membered ring where X1 is located are directly connected through a single bond; when L2 is a single bond, it represents that Ar2 and the six-membered ring where X1 is located are directly connected through a single bond; when L3 is a single bond, it represents that the six-membered ring where X1 is located is directly connected to the naphthalene ring in Formula I through a single bond.

[0020] Ar1 and Ar2 are each independently selected from any one of hydrogen, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0021] The substituted substituents in R1, R2, R3, R4, R5, L1, L2, L3, Ar1 and Ar2 are each independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C30 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C60 aryl and C3-C60 heteroaryl, or a combination of at least two thereof; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

[0022] In the present invention, "the substituted substituents are each independently not connected to the adjacent ring structure" means that the substituent is only connected to the C atom through a single bond; "the substituted substituents are each independently connected to the adjacent ring structure through a chemical bond to form a ring" means that the substituent 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.

[0023] 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 range of the substituted substituents is as shown above and will not be repeated.

[0024] The organic compound provided by the present invention has a molecular structure as shown in Formula I, and has the following structural characteristics and technical effects:

[0025] (1) The naphthalene ring in formula I is disubstituted with a nitrogen-containing heteroaryl group (the group shown in formula III) and a 2-naphthylphenyl group (the group shown in formula II), and at least one of the substitutions is at the α position of the naphthalene (i.e., the site where A1 is located). When there is a substituent at the α position of the naphthalene ring, the structure will present a certain angle deviation with the plane of the naphthalene ring. When there is a substituent at the β position of the naphthalene ring, it will often form a good coplanar surface with the naphthyl group. In the present invention, a substituent is connected to the α position of at least one naphthalene ring, and by replacing another group at different positions on the naphthalene ring, the carrier injection and transmission performance of the organic compound can be adjusted accordingly, and different effects are also produced on the stability of the exciton and the energy transfer efficiency.

[0026] (2) The nitrogen-containing heteroaryl group shown in formula III is a group with good electron injection properties, and good electron injection and transmission properties can be achieved through appropriate substitution and modification; at the same time, the 2-naphthylphenyl group shown in formula II is a long-axis low triplet energy level group, which has good stability in the triplet state and is conducive to inserting into the molecular gap to shorten the distance between molecules so that it has a high triplet energy transfer efficiency. The present invention can adjust the carrier injection and transmission properties of the compound and the triplet energy transfer efficiency by replacing the nitrogen-containing heteroaryl group or 2-naphthylphenyl group at the α position of naphthalene, respectively, and achieve a balance between electron injection and transmission and energy transfer; and due to substitution at different positions of the naphthalene ring, the carrier transmission channel and the energy transfer channel of the organic compound can be separated in spatial structure, and in the excited state, especially under triplet excitation, the triplet energy is concentrated in the triplet group for vibration transfer, avoiding the influence of molecular vibration on the carrier transmission performance, so that the organic compound can be used in an organic electroluminescent device to achieve high efficiency.

[0027] (3) The present invention performs double substitution at different positions of the naphthalene ring, which helps to adjust the dipole moment of the molecule and adjust the HOMO energy level and LUMO energy level of the organic compound, thereby improving the electron injection and transmission capabilities of the compound. The organic compound is used in an organic electroluminescent device to achieve the purpose of reducing the device voltage.

[0028] (4) The molecular weight of the organic compound of the present invention is at a reasonable value, which can not only increase the glass transition temperature Tg of the material, but also will not affect the thermal stability of the material due to the excessively high evaporation temperature of the compound, so that the organic compound can be applied to the organic electroluminescent device to achieve a long life.

[0029] Therefore, the organic compound provided by the present invention has excellent carrier injection and transmission performance and electron injection and transmission performance through the design of the molecular structure, and achieves an excellent balance between the electron injection and transmission performance and the energy transfer, and has a suitable molecular weight and excellent thermal stability. The organic compound has excellent photoelectric properties, and when used in an organic electroluminescent device, it can effectively improve the luminous efficiency of the device, reduce the voltage, and extend the working life of the device.

[0030] 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 molecular structure, which is the result of the synergistic effect of each group, rather than the effect of a single group.

[0031] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The same descriptions below have the same meanings.

[0032] 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.

[0033] 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.

[0034] 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.

[0035] In the present invention, "-*" and "*" both represent the connection site of a group.

[0036] 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.

[0037] In the present invention, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0038] In the present invention, C1-C30 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26 or C28, etc.

[0039] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0040] 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.

[0041] The C2-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0042] 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.

[0043] The C2-C10 can all be C3, C4, C5, C6, C7, C8, C9, etc.

[0044] 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.

[0045] 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.

[0046] In the present invention, the C1-C30 straight chain or branched alkyl group, preferably a C1-C20 straight chain or branched alkyl group, 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 and the like.

[0047] Specific examples of the C1-C30 alkoxy group include monovalent groups obtained by connecting the above-mentioned linear or branched alkyl groups to O.

[0048] The C3-C30 cycloalkyl, preferably C3-C20 cycloalkyl, further preferably C3-C10 cycloalkyl, includes monocyclic alkyl or polycyclic alkyl. Wherein, monocyclic alkyl refers to an alkyl containing a single cyclic structure, and polycyclic alkyl 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.

[0049] Specific examples of the C2-C20 heterocycloalkyl group include groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (such as N, O, S, etc.), including but not limited to: epoxy, oxetanyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyrrolyl, tetrahydropyranyl, piperidinyl, piperazinyl, dioxane, morpholinyl, etc.

[0050] 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.

[0051] The C6-C60 aromatic group is preferably a C6-C30 aromatic group, and more preferably a C6-C20 aromatic group, including a monocyclic aromatic group and a condensed-ring aromatic group; the monocyclic aromatic group means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are connected by a single bond, and illustratively include but are not limited to: phenyl, biphenyl, terphenyl, quaterphenyl, etc.; specifically, the biphenyl group includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, and m-terphenyl-2-yl. The fused ring aromatic group refers to a group containing at least two aromatic rings, and the aromatic rings share two adjacent carbon atoms and are fused to each other, including, but not limited to, naphthyl (1-naphthyl, 2-naphthyl), anthracenyl (1-anthracenyl, 2-anthracenyl, 9-anthracenyl), phenanthrenyl, indenyl, fluorenyl (1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl) and derivatives thereof (9 ,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, phenylmethylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl (1-pyrenyl, 2-pyrenyl, 4-pyrenyl), peryl, It should be noted that the monocyclic aromatic group and the condensed aromatic group connected by a single bond also belong to the scope of aromatic group, such as phenylnaphthyl, naphthylphenyl, etc.

[0052] The C3-C60 heteroaryl group is preferably a C3-C30 heteroaryl group, and more preferably a C3-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, etc.), the heteroaryl group and the other groups are connected by a single bond, and exemplary examples include but are not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, pyrimidinylphenyl, etc. The fused ring heteroaryl group means a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two share two adjacent atoms that are fused to each other, including, but not limited to, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, naphthiobenzofuranyl, naphthiobenzothiophenyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolcarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc. It should be noted that heteroaryl and heteroaryl groups connected by a single bond, and aryl and heteroaryl groups connected by a single bond also fall within the scope of heteroaryl groups, for example phenylpyridyl, phenylpyrimidinyl, phenyltriazine, phenylquinazolinyl, phenylquinoxalinyl, phenylquinolyl, phenylisoquinolyl, and the like.

[0053] Specific examples of the C6-C60 arylene group include divalent groups obtained by removing a hydrogen atom from the above-mentioned aryl groups; specific examples of the C3-C60 heteroarylene group include divalent groups obtained by removing a hydrogen atom from the above-mentioned heteroaryl groups.

[0054] In the present invention, the organic compound has a structure as shown in Formula I-1 or Formula I-2:

[0055]

[0056] Among them, R1, R2, R3, R4, R5, X1, X2, X3, L1, L2, L3, Ar1, Ar2, a, b, and c have the same defined ranges as those in the aforementioned Formula I, Formula II, and Formula III.

[0057] Preferably, the organic compound has a structure as shown in any one of the following formulas I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-2A, I-2B, I-2C, I-2D, I-2E, and I-2F:

[0058]

[0059]

[0060]

[0061] Among them, R1, R2, R3, R4, R5, X1, X2, X3, L1, L2, L3, Ar1, Ar2, a, b, c have the same defined ranges as in Formula I, Formula II and Formula III.

[0062] Preferably, R1 is selected from any one of hydrogen, cyano, halogen, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl.

[0063] Preferably, R1 is selected from any one of hydrogen, cyano, halogen, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, and substituted or unsubstituted heteroaryl:

[0064]

[0065] Wherein, -* represents the attachment site of the group.

[0066] Z1 is selected from O, S or NR 11 Any one of .

[0067] R 11 Any one or a combination of at least two selected from C1-C30 straight or branched alkyl, C3-C20 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.

[0068] R 12 Any one or a combination of at least two selected from hydrogen, halogen, cyano, C1-C30 straight or branched alkyl, C3-C20 cycloalkyl, C1-C30 alkoxy, C6-C30 aryl, C3-C30 heteroaryl.

[0069] Preferably, the substituents substituted in R1 are each independently selected from any one or a combination of at least two of 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, C16 or C18, etc.) aryl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and more preferably any one of halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, phenyl, biphenyl, naphthyl, pyridyl, pyrazinyl and pyrimidinyl.

[0070] Preferably, R1 is selected from hydrogen, cyano, unsubstituted or halogenated C1-C6 straight or branched alkyl, Any of the above, -* represents the attachment site of the group.

[0071] The "unsubstituted or halogenated C1-C6 straight or branched alkyl group" in R1 illustratively includes, but is not limited to, methyl, ethyl, n-propyl, isopropyl, tert-butyl, perfluoromethyl, and the like.

[0072] Preferably, R2, R3, and R4 are each independently selected from any one of halogen, cyano, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl, and substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl.

[0073] Preferably, R2, R3, and R4 are each independently selected from cyano, substituted or unsubstituted C1-C10 straight or branched alkyl, and any one of the following substituted or unsubstituted groups:

[0074]

[0075] Wherein, -* represents the attachment site of the group.

[0076] Z2 is selected from O, S, CR 21 R 22 or NR 23 Any one of .

[0077] R 21 , R 22 , R 23 Each is independently selected from any one or a combination of at least two of C1-C30 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; the R 21 and R 22 Not connected or connected to form a ring through chemical bonds.

[0078] The substituents substituted in R2, R3 and R4 are each independently selected from any one or a combination of at least two of 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, C16 or C18, etc.) aryl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and more preferably any one of halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, phenyl, biphenyl, naphthyl, pyridyl, pyrazinyl and pyrimidinyl.

[0079] Preferably, Z2 is selected from O, S or CR 21 R 22 .

[0080] Preferably, the R 21 , R 22 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, and further preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl.

[0081] Preferably, R2, R3, and R4 are each independently selected from cyano, unsubstituted or halogenated C1-C6 straight or branched alkyl, Any of the above, -* represents the attachment site of the group.

[0082] In R2, R3, and R4, the “unsubstituted or halogenated C1-C6 straight or branched alkyl” illustratively includes, but is not limited to, methyl, ethyl, n-propyl, isopropyl, tert-butyl, perfluoromethyl, and the like.

[0083] Preferably, at least two of X1, X2 and X3 are N.

[0084] Preferably, X1, X2 and X3 are all N.

[0085] Preferably, L1, L2, and L3 are each independently selected from any one of a single bond, a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylene, and a substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroarylene.

[0086] Preferably, L1, L2, and L3 are each independently selected from any one of the following groups which are single bonds, substituted or unsubstituted:

[0087]

[0088] Wherein, -* represents the attachment site of the group.

[0089] Z3 is selected from O, S, Se, CR 31 R 32 or NR 33 Any one of .

[0090] R 31 , R 32 , R 33 Each is independently selected from any one or a combination of at least two of C1-C30 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; the R 31 and R 32 Not connected or connected to form a ring through chemical bonds.

[0091] Preferably, Z3 is selected from O, S, Se or CR 31 R 32 Any one of .

[0092] Preferably, the R 31 , R 32 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, and further preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl.

[0093] Preferably, the R 31 and R32 Not connected or through chemical bonds L B1 connected into a ring; the L B1 Any one selected from a single bond, O (ether bond), S (thioether bond), C1-C6 (e.g., C2, C3, C4, C5, etc.) straight chain or branched chain alkylene; wherein the C1-C6 straight chain or branched chain alkylene exemplarily includes but is not limited to: methylene, (propylene).

[0094] Preferably, L1, L2, L3 are each independently selected from a single bond, Any of the above, -* represents the attachment site of the group.

[0095] Preferably, Ar1 and Ar2 are each independently selected from any one of hydrogen, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl.

[0096] Preferably, Ar1 and Ar2 are each independently selected from hydrogen, or any one of the following substituted or unsubstituted groups:

[0097]

[0098] Wherein, -* represents the attachment site of the group.

[0099] R 41 Each is independently selected from any one or a combination of at least two of hydrogen, halogen, cyano, C1-C30 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C1-C30 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0100] Y1 and Y2 are each independently selected from O, S, Se, CR 42 R 43 、SiR 44 R 45 or NR 46 Any one of .

[0101] R 42 , R 43 , R 44 , R 45 , R 46Each is independently selected from any one or a combination of at least two of C1-C30 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; the R 42 and R 43 Not connected or connected to form a ring by chemical bonds, the R 44 and R 45 Not connected or connected to form a ring through chemical bonds.

[0102] 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 (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, C16 or C18, etc.) aryl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and more preferably any one of halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, phenyl, biphenyl, naphthyl, pyridyl, pyrazinyl and pyrimidinyl.

[0103] Preferably, the R 41 Each is independently selected from any one of hydrogen, halogen, cyano, 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, and phenyl is more preferred.

[0104] Preferably, the R 42 , R 43 , R 44 , R 45 , R 46 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, and further preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl.

[0105] Preferably, the R 42 and R 43 Not connected or through chemical bonds L B2 Connected into a ring, the R 44 and R 45 Not connected or through chemical bonds LB3 connected into a ring; the L B2 , L B3 Each is independently selected from any one of a single bond, O (ether bond), S (thioether bond), C1-C6 (e.g., C2, C3, C4, C5, etc.) straight chain or branched chain alkylene; wherein the C1-C6 straight chain or branched chain alkylene exemplarily includes but is not limited to: methylene, (propylene).

[0106] Preferably, Ar1 and Ar2 are each independently selected from hydrogen or any one of the following groups:

[0107] Wherein, -* represents the attachment site of the group.

[0108] Preferably, the organic compound has a structure shown in any one of the following A1-A232:

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120] In a second aspect, the present invention provides a use of the organic compound as described in the first aspect, wherein the organic compound is applied to an organic electronic device.

[0121] 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.

[0122] Preferably, the organic compound is applied to an organic electroluminescent device, and more preferably applied to a red organic electroluminescent device.

[0123] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device, more preferably as a host material of the light-emitting layer, and even more preferably as a red light host material.

[0124] 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 organic compound as described in the first aspect.

[0125] Preferably, the organic layer comprises at least one organic compound having a structure shown as A1-A232.

[0126] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one organic compound as described in the first aspect.

[0127] Preferably, the light-emitting layer includes a main material and a doping material, and the main material includes at least one organic compound as described in the first aspect; further preferably, the main material includes at least one organic compound with a structure shown in A1-A232.

[0128] Preferably, the doping material (also called "dye", "luminescent dye", "guest material") is a phosphorescent doping material.

[0129] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0130] 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.

[0131] 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.

[0132] In a preferred technical solution, the organic electroluminescent device (OLED device) comprises a first electrode, a second electrode, and an organic layer located 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 organic compound as described in the first aspect, and further preferably comprises at least one organic compound having a structure shown in A1-A232.

[0133] In a preferred technical solution, the organic electroluminescent device comprises a first electrode, a plurality of light-emitting functional layers (organic layers) and a second electrode arranged in sequence; the organic layer comprises 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) comprises at least one organic compound as described in the first aspect, and further preferably comprises at least one organic compound having a structure shown in A1-A232.

[0134] 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.

[0135] 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.

[0136] 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.

[0137] 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.

[0138] 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.

[0139]

[0140]

[0141]

[0142] 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.

[0143]

[0144] 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.

[0145] 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.

[0146] 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.

[0147] In one aspect of the present invention, the host material of the light-emitting layer adopts the organic compound of the present invention.

[0148] In 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. In addition, 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 organic compound with a structure shown in Formula I of the present invention, or an organic compound with a structure shown in A1-A232 as described above. The second compound can be selected to match the energy level relationship, carrier transport performance, etc. of the first compound.

[0149] The second compound may include one or more combinations of the following PH-1 to PH-85, but is not limited to one or more combinations of the following PH-1 to PH-85.

[0150]

[0151]

[0152]

[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 GPD-1 to GPD-47 listed below.

[0156]

[0157] Where D is deuterium.

[0158] 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.

[0159]

[0160] 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.

[0161]

[0162] 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.

[0163] 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).

[0164] 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.

[0165]

[0166]

[0167]

[0168]

[0169] 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.

[0170] 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.

[0171] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0172] Preferably, the display device includes a display screen or a display panel.

[0173] The present invention also provides an electronic device, which includes the above-mentioned display device.

[0174] Compared with the prior art, the present invention has the following beneficial effects:

[0175] The organic compound provided by the present invention has a structure as shown in Formula I, and through the design of the molecular structure, it has excellent carrier injection and transmission performance and electron injection and transmission performance, and achieves an excellent balance between electron injection and transmission performance and energy transfer, and has a suitable molecular weight and excellent thermal stability. The organic compound has excellent photoelectric properties, and is used in organic electroluminescent devices to effectively improve the luminous efficiency of the device, reduce voltage, and extend the working life of the device. DETAILED DESCRIPTION

[0176] 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.

[0177] The 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.

[0178] In a specific embodiment, the organic compound has a structure as shown in Formula I-1, and can be prepared by a representative synthesis route as shown below:

[0179]

[0180] Wherein, R1, R2, R3, R4, R5, X1, X2, X3, L1, L2, L3, Ar1, Ar2, a, b, c have the same defined ranges as those in Formula I, Formula II and Formula III; M1 and M2 are each independently selected from any one of I, Br or OTf (trifluoromethanesulfonate); M3 is selected from any one of I, Br, Cl or OTf.

[0181] In one embodiment, the organic compound has a structure shown in Formula I-2, and its representative synthesis route is similar to the above-mentioned route, except that the raw material S is replaced by That's it.

[0182] The specific preparation method of the organic compound of the present invention will be described in detail below using multiple synthesis examples as examples. However, the preparation method of the organic compound of the structure shown in 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 organic compound of the structure shown in Formula I synthesized by other methods also belongs to the protection scope of the present invention.

[0183] The following synthesis examples of the present invention provide specific synthesis methods of representative compounds by way of example. The solvents and reagents used in the synthesis examples can all 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 were obtained by testing using a ZAB-HS mass spectrometer (manufactured by Micromass, UK).

[0184] 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.

[0185] Synthesis Example 1: Synthesis of Compound A1

[0186]

[0187] S1 (2-bromonaphthalene, 20 g), S2 (p-chlorophenylboronic acid, 15.5 g), potassium carbonate (27 g) were added to a three-necked flask, and solvent dioxane (200 mL) and water (30 mL) were added, and then tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.89 g) was added after nitrogen replacement, and the temperature was raised to reflux for overnight reaction. After the reaction was completed, the solvent was concentrated, and dichloromethane DCM was added to dissolve and extract, and the organic phase was collected, and then purified and separated by silica gel column to obtain A1-1 (21 g) as a white solid.

[0188] Under nitrogen protection, A1-1 (21 g), pinacol diboron (30 g), and potassium acetate (25 g) were dissolved in dioxane (250 mL), and tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 1.4 g) and 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (1.4 g) were added, and heated to reflux for 7 h under nitrogen protection. After concentration, the mixture was dissolved in DCM and purified by silica gel column chromatography to obtain A1-2 (24 g) as a white solid.

[0189] In a three-necked flask, add A1-2 (24 g), S3 (1-bromo-3-chloronaphthalene, 17.2 g), potassium carbonate (22 g) into a single-necked flask, then add solvent dioxane (250 mL) and water (40 mL), add Pd(PPh3)4 (0.89 g) after nitrogen replacement, heat to 106 ° C and reflux for 5 hours. A large amount of solid precipitates in the system, which is filtered after cooling, rinsed with water and ethanol, and dried to obtain A1-3 (20.6 g) as a white solid.

[0190] A1-3 (20.6 g), biboric acid pinacol ester (22 g), potassium acetate (18 g) were added to a three-necked flask, and 250 mL of dioxane solvent was added. Then, after nitrogen replacement, palladium acetate (Pd(OAc)2, 0.30 g) and 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (1.18 g) were added, and the temperature was raised to reflux for overnight reaction. After the reaction was completed, the solvent was filtered and concentrated, dissolved in DCM, and purified by silica gel column to obtain A1-4 (20 g) as a white solid.

[0191] A1-4 (20 g), S4 (2-chloro-4,6-diphenyl-1,3,5-triazine, 11.7 g), potassium carbonate (13 g), Pd(PPh3)4 (0.62 g), 200 mL of dioxane and 30 mL of water were added to a 500 mL three-necked flask, and then the nitrogen was replaced by vacuum three times, and the temperature was raised to 108°C, and the reaction was allowed to proceed overnight. After the reaction was completed, the heating was stopped, and the mixture was cooled to room temperature and filtered. The filtered solid was purified by silica gel column chromatography, and the obtained crude product was recrystallized from xylene to obtain a white solid A1 (12 g). M / Z theoretical value: 561.224; measured value: 562.2 (M+1).

[0192] Synthesis example 2-16

[0193] The following organic compounds were prepared by a synthetic method similar to that of A1, except that S2, S3, and S4 were replaced by equimolar amounts of the compounds shown in Table 1.

[0194] Table 1

[0195]

[0196]

[0197]

[0198] The present invention exemplifies the specific synthesis methods of the above compounds. For organic compounds for which no specific synthesis methods are given in the following embodiments, they are also prepared by similar methods, and only the raw materials need to be replaced, which will not be described in detail here, or those skilled in the art can also prepare them by other methods in the prior art.

[0199] Example 1

[0200] 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:

[0201] (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;

[0202] (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-4:HI-2 (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;

[0203] (3) vacuum evaporating compound HT-4 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;

[0204] (4) vacuum evaporating compound HT-47 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 5 nm;

[0205] (5) Vacuum evaporation of the main material on the electron blocking layer: RPD-7 (100 / 3, w / w) binary mixture as the light-emitting layer, the main material is the organic compound A1 provided by the present invention, the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 40 nm;

[0206] (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;

[0207] (7) vacuum evaporating a mixture of compounds ET-67: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;

[0208] (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;

[0209] (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.

[0210] Examples 2-16, Comparative Examples 1-6

[0211] An organic electroluminescent device, which differs from Example 1 only in that the main materials of the light-emitting layer are the compounds shown in Table 2; other layers, thicknesses, materials and preparation methods are the same as those in Example 1.

[0212] The structure of the main material in the above comparative example is as follows:

[0213]

[0214] Among them, the synthesis methods of compounds CP1, CP2 and CP4 are detailed in the prior art KR20220055392A, the synthesis method of compound CP3 is detailed in the prior art JP2019501513A, the synthesis method of compound CP5 is detailed in the prior art KR101966306B1, and the synthesis method of compound CP6 is detailed in the prior art WO2021131657A1.

[0215] The performance test of the organic electroluminescent devices provided in Examples 1-16 and Comparative Examples 1-6 was performed in the following manner:

[0216] At the same brightness, the driving voltage, current efficiency and device life of each organic electroluminescent device 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 when it reached 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.

[0217] The test values ​​of voltage, current efficiency and life of comparative example 1 are recorded as 1, and the ratios of the test values ​​of voltage, current efficiency and life of other devices to the test values ​​of voltage, current efficiency and life of comparative example 1 (relative voltage, relative current efficiency and relative life) are calculated. The specific results are shown in Table 2.

[0218] Table 2

[0219]

[0220]

[0221] Combined with the data in Table 2, it can be seen that the organic compound provided by the present invention has excellent photoelectric properties. As the main material of the red light emitting layer of the organic electroluminescent device, it effectively improves the luminous efficiency and working life of the device and reduces the driving voltage.

[0222] Compared with the device prepared by using the prior art compound CP1-CP6 as the main material of the light-emitting layer, the organic compound provided by the present invention is used as the main material of the light-emitting layer, so that the organic electroluminescent device has a lower voltage and a higher lifespan, and the luminous efficiency of the device is relatively higher. The reasons are speculated as follows: Comparative Examples 1-3 respectively use the compounds CP1-CP3 in the prior art, and the triazine groups in CP1-CP3 are all bridged with naphthyl, but the triplet energy level of the molecule as a whole is relatively high. Although it may have good electron injection transmission, the carrier transmission is unbalanced when it is used as the main material of the light-emitting layer, and the transmission of electrons is stronger than the transmission of holes, so that the exciton composite interface deviates from the light-emitting layer. At the same time, due to the high triplet energy level of the entire molecule, it is impossible to quickly transfer energy to the dye, so the device performance is worse. In CP4, the triazine group and 2-naphthylbenzene are bridged by naphthyl 2,6 positions, respectively, which makes the molecule very rigid, the plane is too large, and it is easy to accumulate and crystallize. The excitons are easily accumulated and quenched at high brightness, which seriously affects the device performance. The triazine group in CP5 is bridged to 2-naphthylbenzene through the 1,4 positions of the naphthyl group. In terms of spatial configuration, the plane of the triazine group and 2-naphthylbenzene are in the same plane, and form a certain angle with the bridged naphthalene. Similarly, the triazine group in CP6 is bridged to 4-phenylnaphthalene through the 1,4 positions of the naphthyl group. The plane of the triazine group and 4-phenylnaphthalene are in the same plane, and form a certain angle with the bridged naphthalene. When CP5-CP6 is used to prepare the red light host material in the light-emitting layer of OLED, it is easy to cause triplet excitons to form polarons with electrons injected into the coplanar triazine, causing polaron-exciton quenching, which not only weakens the exciton formation efficiency, but also causes device instability, making the overall device performance worse.

[0223] The applicant declares that the present invention uses the above-mentioned embodiments to illustrate the organic compounds and their applications, and the organic electroluminescent devices containing the same, 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 the 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 The organic compound has a structure as shown in Formula I: Wherein, one of A1 and A2 is a group represented by formula II, and the other is a group represented by formula III: -* represents the attachment site of the group; R1 is selected from any one of hydrogen, cyano, halogen, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, C1-C30 alkoxy, substituted or unsubstituted C3-C60 heteroaryl; R2, R3, and R4 are each independently selected from any one of halogen, cyano, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; a is an integer selected from 0-5, b is an integer selected from 0-7, and c is an integer selected from 0-4; X1, X2, and X3 are each independently selected from any one of CR5 and N, and at least one of them is N; R5 is independently selected from any one of hydrogen, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; L1, L2, and L3 are each independently selected from any one of a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group; Ar1 and Ar2 are each independently selected from any one of hydrogen, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; The substituted substituents in R1, R2, R3, R4, R5, L1, L2, L3, Ar1 and Ar2 are each independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C30 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C1-C30 alkoxy, C2-C20 heterocycloalkyl, C6-C60 aryl and C3-C60 heteroaryl, or a combination of at least two thereof; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

2. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in any one of the following formulas I-1A, I-1B, I-1C, I-1D, I-1E, I-1F, I-2A, I-2B, I-2C, I-2D, I-2E, and I-2F: Among them, R1, R2, R3, R4, R5, X1, X2, X3, L1, L2, L3, Ar1, Ar2, a, b, c have the same defined ranges as in Formula I, Formula II and Formula III.

3. The organic compound according to claim 1 or 2, characterized in that The R1 is selected from any one of hydrogen, cyano, halogen, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, and substituted or unsubstituted C3-C20 heteroaryl; Preferably, R1 is selected from any one of hydrogen, cyano, halogen, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, and substituted or unsubstituted heteroaryl: Wherein, -* represents the attachment site of the group; Z1 is selected from O, S or NR 11 Any of the following: R 11 Any one or a combination of at least two selected from C1-C30 straight or branched alkyl, C3-C20 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; R 12 Any one or a combination of at least two selected from hydrogen, halogen, cyano, C1-C30 straight or branched alkyl, C3-C20 cycloalkyl, C1-C30 alkoxy, C6-C30 aryl, C3-C30 heteroaryl; Preferably, the substituents in R1 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, C3-C20 heteroaryl.

4. The organic compound according to claim 3, characterized in that The R1 is selected from hydrogen, cyano, unsubstituted or halogenated C1-C6 straight or branched alkyl, Any of the above, -* represents the attachment site of the group.

5. The organic compound according to claim 1 or 2, characterized in that The R2, R3, and R4 are each independently selected from any one of halogen, cyano, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl; Preferably, R2, R3, and R4 are each independently selected from cyano, substituted or unsubstituted C1-C10 straight or branched alkyl, and any one of the following substituted or unsubstituted groups: Wherein, -* represents the attachment site of the group; Z2 is selected from O, S, CR 21 R 22 or NR 23 Any of the following: R 21 , R 22 , R 23 Each is independently selected from any one or a combination of at least two of C1-C30 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; the R 21 and R 22 Not connected or connected into rings by chemical bonds; The substituents in R2, R3 and R4 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; Preferably, Z2 is selected from O, S or CR 21 R 22 ; Preferably, the R 21 , R 22 Each is independently selected from any one of a C1-C10 straight chain or branched chain alkyl group and a C6-C20 aryl group.

6. The organic compound according to claim 5, characterized in that The R2, R3, and R4 are each independently selected from cyano, unsubstituted or halogenated C1-C6 straight or branched alkyl, Any of the above, -* represents the attachment site of the group.

7. The organic compound according to claim 1 or 2, characterized in that At least two of X1, X2 and X3 are N; Preferably, X1, X2 and X3 are all N.

8. The organic compound according to claim 1 or 2, characterized in that The L1, L2, and L3 are each independently selected from any one of a single bond, a substituted or unsubstituted C6-C20 arylene group, and a substituted or unsubstituted C3-C20 heteroarylene group; Preferably, L1, L2, and L3 are each independently selected from any one of the following groups which are single bonds, substituted or unsubstituted: Wherein, -* represents the attachment site of the group; Z3 is selected from O, S, Se, CR 31 R 32 or NR 33 Any of the following: R 31 , R 32 , R 33 Each is independently selected from any one or a combination of at least two of C1-C30 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; the R 31 and R 32 Not connected or connected into rings by chemical bonds; Preferably, Z3 is selected from O, S, Se or CR 31 R 32 Any of the following: Preferably, the R 31 , R 32 Each is independently selected from any one of C1-C10 straight or branched alkyl, C6-C20 aryl; Preferably, the R 31 and R 32 Not connected or through chemical bonds L B1 connected into a ring; the L B1 Any one selected from a single bond, O, S, C1-C6 straight chain or branched chain alkylene.

9. The organic compound according to claim 8, characterized in that The L1, L2, and L3 are each independently selected from a single bond, Any of the above, -* represents the attachment site of the group.

10. The organic compound according to claim 1 or 2, characterized in that Ar1 and Ar2 are each independently selected from any one of hydrogen, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl; Preferably, Ar1 and Ar2 are each independently selected from hydrogen, or any one of the following substituted or unsubstituted groups: Wherein, -* represents the attachment site of the group; R 41 Each is independently selected from any one or a combination of at least two of hydrogen, halogen, cyano, C1-C30 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C1-C30 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl; Y1 and Y2 are each independently selected from O, S, Se, CR 42 R 43 、SiR 44 R 45 or NR 46 Any of the following: R 42 , R 43 , R 44 , R 45 , R 46 Each is independently selected from any one or a combination of at least two of C1-C30 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; the R 42 and R 43 Not connected or connected to form a ring by chemical bonds, the R 44 and R 45 Not connected or connected into rings by chemical bonds; The substituents 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; Preferably, the R 42 , R 43 , R 44 , R 45 , R 46 Each is independently selected from any one of C1-C10 straight or branched alkyl, C6-C20 aryl; Preferably, the R 42 and R 43 Not connected or through chemical bonds L B2 Connected into a ring, the R 44 and R 45 Not connected or through chemical bonds L B3 connected into a ring; the L B2 , L B3 Each is independently selected from any one of a single bond, O, S, and a C1-C6 straight or branched chain alkylene.

11. The organic compound according to claim 10, characterized in that The Ar1 and Ar2 are each independently selected from hydrogen or any one of the following groups: Wherein, -* represents the attachment site of the group.

12. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in any one of the following A1-A232:

13. Use of an organic compound as claimed in any one of claims 1 to 12, characterized in that: The organic compound is applied to organic electronic devices; Preferably, the organic electronic device comprises an organic electroluminescent device; Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

14. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one organic compound according to any one of claims 1 to 12; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one organic compound according to any one of claims 1 to 12; Preferably, the light-emitting layer comprises a host material and a doping material, and the host material comprises at least one organic compound as claimed in any one of claims 1 to 12.

15. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 14.

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