Organic compound and application thereof

Abstract

The invention provides an organic compound and application thereof, the organic compound has a structure as shown in a formula I. Through the design of a molecular structure, the organic compound has a suitable rigid stereo structure and LUMO / HOMO energy level, excellent photoelectric properties and thermodynamic stability, high hole mobility and excellent hole injection and transmission capability, and can effectively block excitons. The organic compound is used for the organic electroluminescent device, is suitable for being used as an electron blocking material and / or a hole transport material, and can improve and balance the transport of carriers in the device, so that the device has higher efficiency, longer service life and lower voltage. The organic compound provided by the invention is an organic light-emitting functional material with excellent performance, has a wide application prospect, and is simple and feasible in preparation process, easily available in raw materials and suitable for mass production and amplification.

Description

Technical Field

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

[0002] Organic Light Emission Diode (OLED) devices are an emerging display technology in recent years. They have the characteristics of high brightness, fast response, low energy consumption, wide viewing angle, flexibility, large temperature adaptability range, and simple process. They have been widely used in display panels of products such as lighting fixtures, smart phones and tablet computers, and are further expanding to large-size display products such as televisions.

[0003] OLED devices have a sandwich-like structure, including a cathode, an anode, and an organic functional material layer sandwiched between the two electrodes; when voltage is applied to the electrodes of the OLED device, electrons and holes are injected and transported to the light-emitting area and recombine there, thereby generating excitons and emitting light. The core of the OLED device is the organic functional material layer, and the common organic functional materials that constitute this material layer include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, luminescent host materials, and luminescent guests (dyes), etc.

[0004] The light-emitting principles of OLED devices mainly include fluorescence, phosphorescence, thermally excited delayed fluorescence and thermally excited sensitized fluorescence. Common fluorescent luminescent bodies 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) can simultaneously use triplet excitons and singlet excitons to emit light, which are called phosphorescent luminescent bodies. Their energy conversion efficiency can be increased by up to four times that of traditional fluorescent luminescent bodies. Thermally excited delayed fluorescence (TADF) technology promotes the transformation of triplet excitons to singlet excitons. Without the use of metal complexes, triplet excitons can still be effectively utilized to achieve higher luminescence efficiency. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the luminescent body through energy transfer, which can also achieve higher luminescence efficiency.

[0005] In OLED devices, hole transport materials play an important role in transferring holes injected from the anode to the light-emitting layer. Hole transport materials with excellent hole mobility are conducive to the injection balance of carriers in the device, thereby reducing the device driving voltage. Moreover, since the excitons generated in the light-emitting layer will move to the hole transport layer, it will eventually lead to light emission at the interface between the hole transport layer and the light-emitting layer, resulting in color cast and reduced luminous efficiency. This requires an auxiliary layer, namely an electron blocking layer, between the hole transport layer and the light-emitting layer to block the migration of excitons to the hole transport layer and prevent efficiency roll-off, thereby improving luminous efficiency, delaying device attenuation, and improving device stability. Although products using OLED display technology have been commercialized, and electron blocking materials have also developed rapidly and their types are increasing, there are still only a handful of materials that can simultaneously meet the requirements of device voltage, efficiency, service life, and device stability. Therefore, the development of low-voltage, high-efficiency, long-life, and stable electron blocking materials is of vital importance to the development of OLED display technology, and is also a problem that needs to be solved in this field. Summary of the invention

[0006] In view of the deficiencies in the prior art, the object of the present invention is to provide an organic compound and its application, wherein the organic compound has a suitable energy level, excellent photoelectric properties and thermal stability, can improve and balance the transport of carriers in the device, and is used in organic electroluminescent devices, and is particularly suitable as an electron blocking material and / or a hole transport material, which can reduce the voltage of the device and improve the luminous efficiency and service life.

[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, X is C or Si.

[0011] In Formula I, L 1 , L 2 , L 3 Each is independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group. 1 When it is a single bond, it represents Ar 1 Directly connected to the N atom through a single bond; when L 2 When it is a single bond, it represents R 4 The benzene ring is directly connected to the N atom through a single bond; when L 3 When it is a single bond, it represents Ar 2The benzene ring is directly connected to the N atom through a single bond.

[0012] In Formula I, Ar 1 Any one selected from a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C5-C60 heteroaryl group.

[0013] In Formula I, Ar 2 Any one selected from a substituted phenyl group, a substituted or unsubstituted C10-C60 aryl group, and a substituted or unsubstituted C5-C60 heteroaryl group.

[0014] In Formula I, R 1 , R 2 , R 3 , R 4 Each is independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0015] In Formula I, R 5 , R 6 , R 7 Each is independently selected from any one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, phenyl, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0016] The R 5 , R 6 and R 7 At most two (e.g., 0, 1, or 2) of the 5 , R 6 and R 7 At least one of them is not hydrogen.

[0017] The R 5 , R 6 , R 7 Any two adjacent groups are not connected, or any two adjacent groups are connected to form a ring through a chemical bond to form any of the following structures:

[0018]

[0019] Wherein, -* represents the structure and L 3 connection site.

[0020] It should be noted that in the present invention There are three different structures: ①R 5 , R 6 and R 7 are not connected to each other, that is, the structure is a substituted phenyl group; ② adjacent R 5 and R 6 As a group, adjacent R 6 and R 7 One of the two groups is connected to form a substituted or unsubstituted naphthalene ring, thereby forming a structure containing an anthracene ring; ③ The adjacent R 5 and R 6 As a group, adjacent R 6 and R 7 As a group, both groups are connected to form structure.

[0021] a, b, c, d represent substituents R 1 , R 2 , R 3 , R 4 The number of substituents; e represents the substituent R 8 The number of.

[0022] a, b, and c are each independently selected from integers of 0-5, for example, 0, 1, 2, 3, 4 or 5.

[0023] d is selected from an integer of 0-4, for example, it can be 0, 1, 2, 3 or 4.

[0024] e is an integer selected from 0-6, for example, 0, 1, 2, 3, 4, 5 or 6.

[0025] When a≥2, multiple (at least 2) R 1 are the same or different groups; the same applies to b, c, d, and e. For the sake of brevity, they are not described one by one.

[0026] L 1 , L 2 , L 3 ,Ar 1 ,Ar 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R7 The substituents substituted in 8 Each is independently selected from any one or a combination of at least two of halogen, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C2-C20 alkenyl, C1-C20 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 by chemical bonds.

[0027] 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.

[0028] 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.

[0029] The organic compound provided by the present invention has a structure shown in Formula I, wherein a specific The structural unit is a parent core, which ensures that the organic compound has better electron blocking performance and effectively prevents electrons and triplet excitons from leaking to the hole transport layer; at the same time, the structure has better thermodynamic stability, thereby improving the stability and service life of the device. 2 The group is connected to the benzene ring and is adjacent to the C atom to which the aromatic amine N is connected, which is beneficial to the improvement of hole mobility and the increase of the blocking ability of excitons, so that the injection and transmission of holes can be better balanced, the molecular space structure is more compact, the film stacking morphology is good, and the stability and film forming properties are good. 2It is a specific type of aromatic or heteroaromatic group, connected to the N-ortho position of aromatic amine. Compared with other structures, the structural design of the present invention makes the steric hindrance of the compound greater, the molecular structure more distorted, and the HOMO-LUMO electron cloud overlap is reduced, so that its LUMO energy level is improved, thereby increasing the electron blocking and hole transport capabilities of the molecule. In addition, the introduction of the tetraphenyl structure can effectively adjust the rigid three-dimensional structure of the molecule, effectively improve the refractive properties of the molecule, facilitate the formation of a stable amorphous film, and facilitate the stability of the device.

[0030] The present invention, through the design of molecular structure, makes the organic compound have suitable rigid stereostructure and LUMO / HOMO energy level, excellent photoelectric performance and thermodynamic stability, high hole mobility, excellent hole injection and transmission ability, and can effectively block excitons. The organic compound is used in organic electroluminescent devices, suitable for being used as electron blocking materials and / or hole transport materials, so that the device has higher efficiency, longer life and lower voltage, and the performance is significantly improved compared with the prior art. Therefore, the organic compound provided by the present invention is an organic light-emitting functional material with good performance, has broad application prospects, and the preparation process is simple and easy, the raw materials are easy to obtain, and is suitable for mass production and amplification.

[0031] It should be noted that, for the sake of convenience, the possible effects of each group / feature are described separately in this application, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between the various groups / features, rather than the effect of a single group / feature.

[0032] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0033] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The following descriptions involving the same have the same meaning.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] In the present invention, "*" indicates the attachment point of the group.

[0038] 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.

[0039] In the present invention, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0040] In the present invention, the C6-C30 may be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28.

[0041] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, 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 C5-C60 can all be 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.

[0044] The C10-C60 can all be 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.

[0045] The C1-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] 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.

[0047] 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.

[0048] 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.

[0049] In the present invention, the C6-C60 aryl group (preferably C6-C30 aryl group) and the C10-C60 aryl group (preferably C10-C30 aryl group) include monocyclic aryl groups and condensed aryl groups; the monocyclic aryl group means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are connected by single bonds, and exemplary examples 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 The groups in which adjacent carbon atoms are fused to each other 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, 9-methyl-9-phenylfluorenyl, 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.

[0050] The C3-C60 heteroaryl, the C5-C60 heteroaryl, preferably the C6-C30 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, exemplarily 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.

[0051] In the present invention, specific examples of the C6-C30 arylene group include divalent groups obtained by removing a hydrogen atom from the above-mentioned aryl groups; specific examples of the C3-C30 heteroarylene group include divalent groups obtained by removing a hydrogen atom from the above-mentioned heteroaryl groups.

[0052] In the present invention, the C6-C30 aryloxy group is a monovalent group formed by connecting the above-mentioned aryl groups and O, and the C3-C30 heteroaryloxy group is a monovalent group formed by connecting the above-mentioned heteroaryl groups and O.

[0053] In the present invention, specific examples of the C6-C60 arylamino and C6-C30 arylamino groups 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 and C3-C30 heteroarylamino groups 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.

[0054] 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.

[0055] Specific examples of the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned linear or branched alkyl groups to O.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] Preferably, the R 5 , R 6 , R 7 Any two adjacent groups are not connected, and the R 5 , R 6 and R 7 At least one of them is selected from a substituted or unsubstituted C6-C30 aryl group, and further preferably a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl group.

[0061] Preferably, the R 5 , R 6 and R 7 At least one of them is a group represented by formula a:

[0062]

[0063] In formula a, -* represents the attachment site of the group;

[0064] m represents a substituent R 11 The number is selected from an integer of 0-5, for example, 0, 1, 2, 3, 4 or 5; when m≥2, multiple R 11 are the same or different groups.

[0065] R 11 Each is independently selected from any one or a combination of at least two of halogen, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 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.

[0066] Preferably, the organic compound has a structure as shown in any one of Formula II-1, Formula II-2, and Formula II-3:

[0067]

[0068] Among them, X, L 1 , L 2 , L 3 ,Ar 1 ,Ar 2 , R 1 , R 2 , R 3 , R 4 , a, b, c and d have the same defined ranges as those in Formula I, and R 11 and m have the same defined ranges as in formula a.

[0069] Preferably, the R 11Each is independently selected from any one of 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, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and more preferably any one of C1-C6 straight or branched alkyl, such as methyl, ethyl, Any one of .

[0070] Preferably, m is 0 or 1.

[0071] Preferably, the R 5 , R 6 , R 7 Any two adjacent groups are connected by chemical bonds to form ring A, or the R 5 , R 6 , R 7 Any two adjacent groups are connected to form ring B by chemical bonds; the organic compound has a structure as shown in any one of formula III-1, formula III-2, and formula III-3:

[0072]

[0073]

[0074] Among them, X, L 1 , L 2 , L 3 ,Ar 1 ,Ar 2 , R 1 , R 2 , R 3 , R 4 , a, b, c and d have the same defined ranges as those in Formula I, and R 8 and e have the same limitations as above.

[0075] Preferably, the L 1 , L 2 , L 3 Each is independently selected from a single bond or a C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) arylene group, more preferably a single bond or a phenylene group, and even more preferably a single bond.

[0076] Preferably, the Ar 1Any one selected from substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.) aryl, substituted or unsubstituted C5-C30 (e.g., C5, C6, C8, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.) heteroaryl.

[0077] Preferably, the Ar 1 Any one selected from the following substituted or unsubstituted groups:

[0078]

[0079] in, Represents the attachment site of the group.

[0080] Z 1 , Z 2 Each independently selected from O, S, CR 21 R 22 or NR 23 Any one of .

[0081] R 21 , R 22 , R 23 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; 21 and R 22 Not connected or connected to form a ring through chemical bonds.

[0082] Preferably, the R 21 , R 22 , R 23 Each is independently selected from any one or a combination of at least two of C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, C2-C10 (e.g. C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C6-C20 (e.g. C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, more preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl, and even more preferably methyl or phenyl.

[0083] Preferably, the R 21 and R 22 Not connected or through chemical bonds L 11 Connected into a ring, the L 11Any one selected from a single bond, O, S, C1-C6 (e.g., C2, C3, C4 or C5, etc.) straight chain or branched alkylene, more preferably a single bond, O (ether bond), S (thioether bond), Any one of .

[0084] Preferably, Ar 1 The substituted substituents are selected from any one or a combination of at least two of 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, and C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

[0085] Preferably, Ar 1 The substituted substituent is selected from any one of methyl, ethyl, isopropyl, tert-butyl, tert-pentyl, cyclohexyl, phenyl, carbazolyl, fluorenyl, methylfluorenyl and phenylfluorenyl.

[0086] Preferably, Ar 1 The substituted substituents are each independently not connected to the adjacent ring structure or are connected by chemical bonds to form a ring Cy1, wherein the ring Cy1 is selected from any one of a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) alicyclic ring, a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring, and a substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaromatic ring, and more preferably The dashed line represents the fused bond of ring Cy1.

[0087] Preferably, the Ar 1 Any one selected from the following groups:

[0088]

[0089] Represents the attachment site of the group.

[0090] Preferably, the Ar 2Any one selected from substituted phenyl, substituted or unsubstituted C10-C20 (e.g. C12, C14, C15, C16, C18, etc.) aryl, substituted or unsubstituted C5-C20 (e.g. C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl.

[0091] Preferably, the Ar 2 Any one selected from substituted phenyl, substituted or unsubstituted following groups:

[0092]

[0093] in, Represents the attachment site of the group.

[0094] Z 3 , Z 4 Each independently selected from O, S, CR 31 R 32 or NR 33 Any one of .

[0095] R 31 , R 32 , R 33 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; 31 and R 32 Not connected or connected to form a ring through chemical bonds.

[0096] Preferably, the R 31 , R 32 , R 33 Each is independently selected from any one or a combination of at least two of C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, C2-C10 (e.g. C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C6-C20 (e.g. C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, more preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl, and even more preferably methyl or phenyl.

[0097] Preferably, the R 31 and R 32 Not connected or through chemical bonds L 21 Connected into a ring, the L 21Any one selected from a single bond, O, S, C1-C6 (e.g., C2, C3, C4 or C5, etc.) straight chain or branched alkylene, more preferably a single bond, O (ether bond), S (thioether bond), Any one of .

[0098] Preferably, Ar 2 The substituted substituents are selected from any one or a combination of at least two of 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, and C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

[0099] Preferably, Ar 2 The substituted substituent is selected from any one of methyl, ethyl, isopropyl, tert-butyl, tert-pentyl, cyclohexyl, phenyl, carbazolyl, fluorenyl, methylfluorenyl and phenylfluorenyl.

[0100] Preferably, Ar 2 The substituted substituents are each independently not connected to the adjacent ring structure or are connected by chemical bonds to form a ring Cy2, wherein the ring Cy2 is selected from any one of a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) alicyclic ring, a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring, and a substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaromatic ring, and more preferably The dashed line represents the fused bond of ring Cy2.

[0101] Preferably, the Ar 2 Any one selected from the following groups:

[0102]

[0103] Represents the attachment site of the group.

[0104] As a preferred technical solution of the present invention, X is Si.

[0105] As a preferred technical solution of the present invention, the R 1 , R 2 , R 3 , R 4 Each is independently selected from any one of cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C25 or C28, etc.) aryl, substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C25 or C28, etc.) heteroaryl.

[0106] As a preferred technical solution of the present invention, a, b, c, and d are each independently 0 or 1.

[0107] Preferably, the organic compound has a structure shown in any one of the following P1-P576:

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132] 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.

[0133] 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.

[0134] Preferably, the organic electronic device comprises an organic electroluminescent device.

[0135] Preferably, the organic compound is applied to an organic electroluminescent device.

[0136] Preferably, the organic compound is used as an electron blocking material and / or a hole transport material in an organic electroluminescent device.

[0137] 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.

[0138] Preferably, the organic layer comprises an electron blocking layer, and the electron blocking layer comprises at least one organic compound as described in the first aspect.

[0139] Preferably, the organic layer comprises a hole transport layer, and the hole transport layer comprises at least one organic compound as described in the first aspect.

[0140] In a preferred technical solution, the organic electroluminescent device (OLED device) comprises a first electrode and a second electrode, and an organic layer located between the electrodes. The organic layer can be divided into multiple regions, for example, including a hole transport region, a light-emitting layer and an electron transport region; the hole transport region comprises at least one organic compound as described in the first aspect.

[0141] In a preferred technical solution, the organic electroluminescent device comprises an anode, a hole transport region, a light-emitting layer, an electron transport region and a cathode arranged in sequence; the hole transport region comprises at least one organic compound as described in the first aspect, and further preferably comprises an organic compound having a structure shown in P1-P576.

[0142] Preferably, the hole transport region comprises 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; the hole transport layer and / or the electron blocking layer comprises at least one organic compound as described in the first aspect.

[0143] Further preferably, the electron blocking 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 as P1-P576.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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, the organic compounds provided in the first aspect of the present invention (for example, the compounds shown in P1-P576); or any combination thereof.

[0150]

[0151]

[0152]

[0153] 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.

[0154]

[0155] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a host material (Host). The light-emitting layer can be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors can be arranged in a plane according to a pixel pattern, or they can be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0156] 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.

[0157] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0158]

[0159] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFD-1 to BFD-24 listed below.

[0160]

[0161]

[0162] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology, and the main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-85.

[0163]

[0164]

[0165]

[0166]

[0167] 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.

[0168]

[0169] Where D is deuterium.

[0170] 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.

[0171]

[0172] 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.

[0173]

[0174] In one aspect of the present invention, the light-emitting layer adopts the technology of thermally activated delayed fluorescence luminescence. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of the above PH-1 to PH-85.

[0175] In one aspect of the present invention, the light-emitting layer adopts the technology of thermally activated delayed fluorescence luminescence. The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of TDE1-TDE37 listed below.

[0176]

[0177]

[0178]

[0179] 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, but not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-47 to PH-77 described above, or one or more compounds of P1 to P576 of the present invention; or a mixture of, but not limited to, one or more compounds of HT-1 to HT-51 and one or more compounds of PH-47 to PH-77, the organic compound provided in the first aspect of the present invention, and more preferably one or more compounds of P1 to P576.

[0180] The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0181] 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.

[0182]

[0183]

[0184]

[0185]

[0186] 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, but not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0187] 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 or Yb.

[0188] In a fifth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the fourth aspect.

[0189] Preferably, the display device includes a display screen or a display panel.

[0190] The present invention also provides an electronic device, which includes the above-mentioned display device.

[0191] Compared with the prior art, the present invention has the following beneficial effects:

[0192] The organic compound provided by the present invention has a structure shown in Formula I, and through the design of the molecular structure, it has a suitable rigid stereostructure and LUMO / HOMO energy level, excellent photoelectric performance and thermodynamic stability, high hole mobility, excellent hole injection and transmission capabilities, and can effectively block excitons. The organic compound is used for organic electroluminescent devices, suitable for being used as an electron blocking material and / or a hole transport material, which can improve and balance the transmission of carriers in the device, so that the device has higher efficiency, longer life and lower voltage, and the comprehensive performance of the device is significantly improved. The organic compound provided by the present invention is an organic light-emitting functional material with excellent performance, has broad application prospects, and the preparation process is simple and easy, and the raw materials are easily available, which is suitable for mass production and amplification. DETAILED DESCRIPTION

[0193] 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.

[0194] In a specific embodiment, the organic compound can be prepared by the following representative synthesis route:

[0195]

[0196] Among them, X, L 1 , L 2 , L 3 ,Ar 1 ,Ar 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , a, b, c, d have the same limited range as Formula I; Hal 1 Hal 2 Each is independently selected from halogen, preferably any one of I, Br, Cl or F, more preferably Br; the order of coupling reaction I and coupling reaction II can be adjusted according to the synthesis situation, that is, coupling reaction I can be carried out first, then coupling reaction II, or coupling reaction II can be carried out first, then coupling reaction I.

[0197] In a specific embodiment, the raw material M can be purchased from the market, or can be prepared by an organic synthesis method known in the art.

[0198] Exemplarily, the raw material M is The synthetic route is as follows:

[0199]

[0200]

[0201] Wherein, THF represents tetrahydrofuran, NBS is N-bromosuccinimide, DCM is dichloromethane; and Pd / C is a palladium-carbon catalyst used for catalytic reduction reaction.

[0202] In a specific embodiment, the coupling reaction I and coupling reaction II are carried out in the presence of a palladium catalyst system.

[0203] Preferably, the coupling reaction I is carried out in the presence of tris(dibenzylacetone)dipalladium(0)Pd2(dba)3, 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride IPr.HCl and sodium tert-butoxide NaOBu-t.

[0204] Preferably, the coupling reaction II is carried out in the presence of Pd2(dba)3, tri-tert-butylphosphine (t-Bu)3P and NaOBu-t.

[0205] The preparation of the organic compound provided by the present invention includes the above method, but is not limited to the above method. The organic compound represented by formula I synthesized by other methods by those skilled in the art also belongs to the protection scope of the present invention.

[0206] More specifically, the following synthesis examples of the present application provide a specific synthesis method of the organic compound, and the solvents and reagents used in the following synthesis examples can all be purchased or customized from the chemical product market. In addition, those skilled in the art can also synthesize by other known methods.

[0207] The mass spectrometry characterization (m / z) data in the following synthesis examples were obtained by testing a ZAB-HS mass spectrometer manufactured by Micromass, UK, specifically a matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOF) mass spectrometry, wherein the ion source was a matrix-assisted laser desorption / ionization (MALDI) and the mass analyzer was a time-of-flight (TOF) analyzer.

[0208] Synthesis Example 1: Synthesis of organic compound P4

[0209]

[0210] (1) In a 1000 mL single-mouth bottle, add 10 g M1 (hereinafter referred to as "raw material M"), 7.21 g p-bromotert-butylbenzene (hereinafter referred to as "raw material S1"), 0.31 g tris(dibenzylacetone)dipalladium(0)Pd2(dba)3, 0.29 g 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride IPr.HCl, 9.76 g sodium tert-butoxide NaOBu-t, 200 mL toluene, evacuate and replace with nitrogen three times, heat the reaction to 90°C for 5 h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, purify the organic phase twice with a silica gel column, concentrate the organic phase, add methanol and reflux and stir for 1 h, filter to obtain a light yellow powder P4-1, and then recrystallize from ethyl acetate to obtain 12.0 g of a white pure product.

[0211] P4-1: m / z theoretical value: 427.231; m / z measured value: 428.209.

[0212] (2) In a 1000 mL single-mouth bottle, add 12.0 g P4-1, 14.0 g 4-bromotetraphenylsilane (hereinafter referred to as "raw material S2"), 0.52 g Pd2(dba)3, 0.23 g tri-tert-butylphosphine (t-Bu)3P, 8.10 g sodium tert-butoxide and 300 mL toluene, evacuate and replace with nitrogen three times, and heat the reaction to 110°C for 8 h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, purify the organic phase twice with a silica gel column, concentrate the organic phase, add methanol and reflux and stir for 1 h, filter to obtain a light yellow powder P4, and then recrystallize from toluene / ethanol three times to obtain 17.5 g of a white pure product.

[0213] Organic compound P4: m / z theoretical value: 761.352; m / z measured value: 762.314.

[0214] Synthesis example 2-20

[0215] The process route of Synthesis Example 2-20 is the same as that of Synthesis Example 1, the only difference being that at least one of the raw materials M, raw material S1, and raw material S2 is different. The raw materials, target products, and m / z characterization data are shown in Table 1.

[0216] Table 1

[0217]

[0218]

[0219]

[0220]

[0221]

[0222] Example 1: Green organic electroluminescent device

[0223] 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 specific preparation method is as follows:

[0224] (1) a glass plate coated with an ITO transparent conductive layer (as an anode) was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone / ethanol, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0225] (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-3 (97 / 3, w / w) on the above anode layer as a hole injection layer, the thickness of the evaporation film is 10 nm;

[0226] (3) Vacuum evaporate 60 nm of HT-4 on the hole injection layer as the hole transport layer of the device;

[0227] (4) vacuum evaporating the organic compound P43 provided by the present invention on the hole transport layer as an electron blocking layer, with a total evaporation film thickness of 35 nm;

[0228] (5) vacuum evaporating a ternary mixture of PH-61:PH-3:GPD-12 (100:100:20, w / w / w) as a light-emitting layer on the electron blocking layer, with a total film thickness of 40 nm;

[0229] (6) Vacuum evaporation of 5 nm of compound ET-23 on the light-emitting layer as a hole blocking layer;

[0230] (7) vacuum evaporating a mixture of compounds ET-69:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer, with a total film thickness of 25 nm;

[0231] (8) Vacuum evaporating LiF with a thickness of 1 nm on the electron transport layer as an electron injection layer;

[0232] (9) Vacuum-evaporating a 150 nm thick metal aluminum on the electron injection layer as a cathode, the total evaporation rate of all organic layers and LiF is controlled at 0.1 nm / s, and the evaporation rate of metal aluminum is 1 nm / s, to obtain the organic electroluminescent device.

[0233] Example 2-11, Comparative Example 1-2

[0234] An organic electroluminescent device, which differs from Example 1 only in that the electron blocking layer materials in step (4) are the organic compounds in Table 2, and the other layers, thicknesses, materials and preparation methods are the same as those in Example 1.

[0235] The structure of the electron blocking layer material in Comparative Example 1-2 is as follows:

[0236]

[0237] The organic electroluminescent devices provided in Examples 1-11 and Comparative Examples 1-2 were subjected to the following performance tests: At the same brightness, the driving voltage and current efficiency of the organic electroluminescent devices were measured using a digital source meter and a brightness meter. 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 10000 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 The current is kept constant at the brightness, and the brightness of the organic electroluminescent device is measured to drop to 9700cd / m 2 time; taking the LT97 life test value of comparative example 1 as 1.0, calculating the ratio (relative life) of the LT97 life test value of other devices to the LT97 life test value of comparative example 1; the test results are shown in Table 2:

[0238] Table 2

[0239]

[0240] Example 12: Red organic electroluminescent device

[0241] 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 specific preparation method is as follows:

[0242] (1) a glass plate coated with an ITO transparent conductive layer (as an anode) was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone / ethanol, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0243] (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-3 (97 / 3, w / w) on the above anode layer as a hole injection layer, the thickness of the evaporation film is 10 nm;

[0244] (3) Vacuum evaporate 60 nm of HT-4 on the hole injection layer as the hole transport layer of the device;

[0245] (4) vacuum evaporating the organic compound P4 provided by the present invention on the hole transport layer as an electron blocking layer, with a total evaporation film thickness of 60 nm;

[0246] (5) vacuum evaporating a binary mixture of compound PH-34:RPD-8 (97 / 3, w / w) on the electron blocking layer as a light-emitting layer, with a total film thickness of 40 nm;

[0247] (6) Vacuum evaporation of 5 nm of compound ET-23 on the light-emitting layer as a hole blocking layer;

[0248] (7) vacuum evaporating a mixture of compounds ET-46:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer, with a total film thickness of 25 nm;

[0249] (8) Vacuum evaporating LiF with a thickness of 0.5 nm on the electron transport layer as an electron injection layer;

[0250] (9) Vacuum-evaporating a 150 nm thick metal aluminum on the electron injection layer as a cathode, the total evaporation rate of all organic layers and LiF is controlled at 0.1 nm / s, and the evaporation rate of metal aluminum is 1 nm / s, to obtain the organic electroluminescent device.

[0251] Examples 13-21, Comparative Examples 3-4

[0252] An organic electroluminescent device, which differs from Example 1 only in that the electron blocking layer materials in step (4) are the organic compounds in Table 3, and the other layers, thicknesses, materials and preparation methods are the same as those in Example 12.

[0253] The structure of the electron blocking layer material in Comparative Example 3-4 is as follows:

[0254]

[0255] The organic electroluminescent devices provided in Examples 12-21 and Comparative Examples 3-4 were subjected to the following performance tests: At the same brightness, the driving voltage and current efficiency of the organic electroluminescent devices were measured using a digital source meter and a brightness meter. 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 3000cd / m 2 The current is kept constant at the brightness, and the brightness of the organic electroluminescent device is measured to drop to 2910cd / m 2 time; taking the LT97 life test value of Comparative Example 3 as 1.0, calculating the ratio (relative life) of the LT97 life test value of other devices to the LT97 life test value of Comparative Example 3; the test results are shown in Table 3:

[0256] Table 3

[0257]

[0258] According to the effect data in Table 2 and Table 3, the organic compound provided by the present invention is used in organic electroluminescent devices, which can effectively reduce the driving voltage, improve the current efficiency, and extend the life of the device. It is an electron blocking material with good performance, which can meet the needs of organic electroluminescent devices with different light colors such as red light and green light, and give red light / green light devices more excellent comprehensive performance.

[0259] Compared with comparative examples 1-4, the ortho position of the benzene ring connected to N in the organic compound of the present invention contains a specific aryl or heteroaryl group, which can make the molecule have better planarity and aromaticity, which is more conducive to improving the mobility of the charge, and the spatial structure is more compact, the thin film stacking morphology is good, the film forming property is good, and it is more conducive to extending the life of the device; compared with comparative example 2, the ortho position of the benzene ring connected to N in P505 contains an isopropyl-substituted phenyl group, which makes the molecule have greater steric hindrance, so that the compound has better electron blocking performance, which is more conducive to preventing electrons and triplet excitons from leaking to the hole layer, thereby improving the efficiency of the device. Compared with comparative example 4, the para position of the phenyl connected to N in P346 contains a phenyl substitution, which can enhance the intermolecular π-π interaction force, so that it has better charge mobility, and the injection and migration of holes reach a better balance. Therefore, compared with the comparative example, the compound in the present invention has better photoelectric properties.

[0260] The applicant declares that the present invention illustrates the organic compounds and applications of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in Formula I: Wherein, X is C or Si; L 1 , L 2 , L 3 Each is independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar 1 Any one selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C5-C60 heteroaryl group; Ar 2 Any one selected from substituted phenyl, substituted or unsubstituted C10-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl; R 1 , R 2 , R 3 , R 4 Each is independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; R 5 , R 6 , R 7 are each independently selected from any one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, phenyl, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and said R 5 , R 6 and R 7 At most two of them are hydrogen; The R 5 , R 6 , R 7 Any two adjacent groups are not connected, or any two adjacent groups are connected to form a ring through a chemical bond to form any of the following structures: Wherein, -* represents the structure and L 3 The attachment site of a, b, c are each independently selected from an integer of 0-5, d are each independently selected from an integer of 0-4, and e is selected from an integer of 0-6; L 1 , L 2 , L 3 ,Ar 1 ,Ar 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 The substituents substituted in 8 Each is independently selected from any one or a combination of at least two of halogen, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C2-C20 alkenyl, C1-C20 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 by chemical bonds.

2. The organic compound according to claim 1, characterized in that The R 5 , R 6 , R 7 Any two adjacent groups are not connected, and the R 5 , R 6 and R 7 At least one of them is selected from substituted or unsubstituted C6-C30 aryl; Preferably, the R 5 , R 6 and R 7 At least one of them is a group represented by formula a: Wherein, -* represents the attachment site of the group; m is an integer selected from 0 to 5; R 11 Each is independently selected from any one or a combination of at least two of halogen, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 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.

3. The organic compound according to claim 2, characterized in that The organic compound has a structure as shown in any one of Formula II-1, Formula II-2, and Formula II-3: Among them, X, L 1 , L 2 , L 3 ,Ar 1 ,Ar 2 , R 1 , R 2 , R 3 , R 4 , a, b, c and d have the same defined ranges as those in Formula I, and R 11 and m have the same defined ranges as in formula a.

4. The organic compound according to claim 3, characterized in that The R 11 Each is independently selected from any one of C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, and C6-C20 aryl, preferably any one of C1-C6 straight or branched alkyl; Preferably, m is 0 or 1.

5. The organic compound according to claim 1, characterized in that The R 5 , R 6 , R 7 Any two adjacent groups are connected by chemical bonds to form ring A, or the R 5 , R 6 , R 7 Any two adjacent groups in the ring are connected by chemical bonds to form ring B; The organic compound has a structure as shown in any one of Formula III-1, Formula III-2 and Formula III-3: Among them, X, L 1 , L 2 , L 3 ,Ar 1 ,Ar 2 , R 1 , R 2 , R 3 , R 4 , a, b, c and d have the same defined ranges as those in Formula I, and R 8 and e have the same definition as in claim 1.

6. The organic compound according to any one of claims 1 to 5, characterized in that The L 1 , L 2 , L 3 Each is independently selected from a single bond or a C6-C20 arylene group, preferably a single bond or a phenylene group, and more preferably a single bond.

7. The organic compound according to any one of claims 1 to 5, characterized in that The Ar 1 Any one selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl; Preferably, the Ar 1 Any one selected from the following substituted or unsubstituted groups: Wherein, -* represents the attachment site of the group; Z 1 , Z 2 Each independently 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 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; 21 and R 22 Not connected or connected into rings by chemical bonds; Preferably, the R 21 , R 22 , R 23 Each is independently selected from any one or a combination of at least two of a C1-C10 straight or branched alkyl group, a C2-C10 alkenyl group, and a C6-C20 aryl group; Preferably, the R 21 and R 22 Not connected or through chemical bonds L 11 Connected into a ring, the L 11 Any one selected from a single bond, O, S, C1-C6 straight chain or branched chain alkylene; Preferably, Ar 1 The substituted substituents are selected from any one or a combination of at least two of C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

8. The organic compound according to claim 7, characterized in that The Ar 1 Any one selected from the following groups: -* represents the attachment site of the group.

9. The organic compound according to any one of claims 1 to 5, characterized in that The Ar 2 Any one selected from substituted phenyl, substituted or unsubstituted C10-C20 aryl, substituted or unsubstituted C5-C20 heteroaryl; Preferably, the Ar 2 Any one selected from substituted phenyl, substituted or unsubstituted following groups: Wherein, -* represents the attachment site of the group; Z 3 , Z 4 Each independently selected from O, S, 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 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; 31 and R 32 Not connected or connected into rings by chemical bonds; Preferably, the R 31 , R 32 , R 33 Each is independently selected from any one or a combination of at least two of a C1-C10 straight or branched alkyl group, a C2-C10 alkenyl group, and a C6-C20 aryl group; Preferably, the R 31 and R 32 Not connected or through chemical bonds L 21 Connected into a ring, the L 21 Any one selected from a single bond, O, S, C1-C6 straight chain or branched chain alkylene; Preferably, Ar 2 The substituted substituents are selected from any one or a combination of at least two of C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

10. The organic compound according to claim 9, characterized in that The Ar 2 Any one selected from the following groups: -* represents the attachment site of the group.

11. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in any one of the following P1-P576:

12. Use of an organic compound as claimed in any one of claims 1 to 11, 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 an electron blocking material and / or a hole transport material in an organic electroluminescent device.

13. 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 11; Preferably, the organic layer comprises an electron blocking layer, and the electron blocking layer comprises at least one organic compound according to any one of claims 1 to 11; Preferably, the organic layer comprises a hole transport layer, and the hole transport layer comprises at least one organic compound as claimed in any one of claims 1 to 11.

14. A display device, characterized in that: The display device comprises the organic electroluminescent device as claimed in claim 13.

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