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 formula I. Through the design of a molecular structure, the organic compound has excellent photoelectric properties, strong conjugation effect, suitable HOMO and LUMO energy levels, higher hole mobility and higher stability, and is beneficial to reducing energy barriers and improving the efficiency of the organic electroluminescent device. And excellent electron blocking performance and hole transport performance are shown. The organic compound is applied to the organic electroluminescent device, is suitable for being used as a hole transport layer material and / or an electron blocking layer material, is especially suitable for being used as an electron blocking layer material, and can effectively improve the luminous efficiency and the stability of the device and prolong the service life of the device.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic electroluminescent materials, and particularly relates to an organic compound and application thereof, and an organic electroluminescent device comprising the same. BACKGROUND

[0002] Organic Light Emission Diode (OLED) devices are a new display technology in recent years, which has the characteristics of high brightness, fast response, low energy consumption, wide viewing angle, flexibility, large temperature adaptation range, simple process, etc., and has been widely used in display panels of lighting lamps, smart phones and tablet computers and further expanded to large-size display products such as televisions.

[0003] OLED devices have a sandwich structure, including two electrodes and an organic functional material layer sandwiched between the two electrodes; when a voltage is applied to the electrodes of the OLED device, electrons and holes are injected and transported to the light-emitting region and recombine there to generate excitons and emit light. The core of the OLED device is the organic functional material layer, and the common organic functional materials constituting the material layer include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, light-emitting host materials and light-emitting guests (dyes), etc.

[0004] According to the light-emitting mechanism of the material, OLEDs can be roughly divided into fluorescent light-emitting, phosphorescent light-emitting, thermally activated delayed fluorescence and thermally activated sensitized fluorescence, etc. Common fluorescent light-emitters mainly utilize the singlet exciton generated when an electron and a hole combine to emit light, and are still widely used in various OLED products. Some metal complexes (such as iridium complexes) can utilize both triplet and singlet excitons for light emission, known as phosphorescent light-emitters, and their energy conversion efficiency can be up to 4 times higher than that of traditional fluorescent light-emitters. The thermally activated delayed fluorescence (TADF) technology promotes the conversion of triplet excitons to singlet excitons, and can effectively utilize triplet excitons without using metal complexes to achieve high light-emitting efficiency. The thermally activated sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the light-emitters through energy transfer, which can also achieve high light-emitting efficiency.

[0005] Hole transport materials significantly impact device performance. On the one hand, they require a suitable HOMO energy level and a suitable energy gap between the hole material and the anode to facilitate hole injection and help reduce operating voltage. On the other hand, hole transport materials regulate the carrier transport balance within the device, improving the carrier mobility of the hole transport material, thereby increasing luminous efficiency and slowing device degradation. Although products using OLED display technology have been commercialized, there are still demands for further improvements in device luminous efficiency, service life, and energy consumption. Currently available commercial hole transport materials cannot fully meet these demands for improved device efficiency, service life, voltage, and energy consumption.

[0006] Therefore, there is an urgent need to develop more types of organic materials with higher performance in this field to improve the performance of organic electroluminescent devices so that the devices have higher luminous efficiency and longer life. Summary of the Invention

[0007] In view of the shortcomings of the prior art, the object of the present invention is to provide an organic compound and its application, and an organic electroluminescent device containing the same. The organic compound has excellent photoelectric properties and is suitable as an electron blocking layer material, which can effectively improve the luminous efficiency of the organic electroluminescent device and extend its service life.

[0008] To achieve this object, the present invention adopts the following technical solutions:

[0009] In a first aspect, the present invention provides an organic compound having a structure as shown in Formula I:

[0010]

[0011] In formula I, group A is selected from unsubstituted or trimethylsilyl-substituted biphenyl, unsubstituted or trimethylsilyl-substituted naphthyl, substituted or unsubstituted C3-C60 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C5 any one of a C3-C60 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.) containing S heteroaryl.

[0012] In Formula I, Ar 1、Ar 2 Each is independently selected from any one of a substituted or unsubstituted C6-C28 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) aryl group, and a substituted or unsubstituted C3-C23 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20 or C22, etc.) heteroaryl group.

[0013] In Formula I, Ar 3 Any one selected from substituted or unsubstituted C6-C18 (e.g., C6, C9, C10, C12, C14, C16 or C18, etc.) aryl, substituted or unsubstituted C3-C60 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.) heteroaryl, wherein the attachment site of Ar3 is the ortho position of the attachment site of the N atom on the group A.

[0014] In Formula I, L 1 、L 2 Each is independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) arylene group, and a substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroarylene group. 1 When it is a single bond, it represents Ar 1 is directly connected to the N atom via a single bond; when the L 2 When it is a single bond, it represents Ar 2 It is directly connected to the N atom via a single bond.

[0015] The substituted substituents are each independently selected from C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.) straight or branched alkyl, C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.) cycloalkyl, C2-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.) heterocycloalkyl, C2-C C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.) alkenyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9, etc.) alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.) alkylsilyl, C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.) alkylamino, C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) arylamino, C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) heteroarylamino, C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) aryloxy, , C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) heteroaryloxy, C6-C60 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40 , C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.) aryl, C3-C60 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38,At least one of heteroaryl groups (C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.).

[0016] In the present invention, the "substituted or unsubstituted" group may be substituted with one or more substituents. When there are multiple substituents (at least two), they may be the same or different. The same expressions used below have the same meaning. Unless otherwise specified, the range of substituents is as shown above and will not be repeated here.

[0017] The substituent includes a trimethylsilyl group, and n represents the number of trimethylsilyl groups in the organic compound. n is an integer selected from 1-3, for example, 1, 2 or 3.

[0018] It should be noted that, in Formula I of the present invention, Indicates that the molecular structure contains n trimethylsilyl groups, and the trimethylsilyl groups can be connected to any site allowed by the present invention, such as Ar 1 、Ar 2 、Ar 3 , L 1 , L 2 , group A.

[0019] The structure of the organic compound provided by the present invention is as shown in Formula I, by the design of molecular structure, the internal force between molecular groups is made greater, rigidity is enhanced, the structure is more stable, σ-π hyperconjugation probability is greater, and then the HOMO energy level of the organic compound is made deeper, which is conducive to reducing energy barriers, contributing to improving the efficiency of devices and extending life. Meanwhile, the organic compound contains trimethylsilyl, so that the molecule has certain resistance in spatial structure, which increases the stability of the molecular structure. The organic compound provided by the present invention has excellent photoelectric properties, strong conjugation effect, suitable HOMO and LUMO energy levels, higher stability, shows excellent electron blocking performance, and is applied to organic electroluminescent devices, suitable as hole transport layer materials and / or electron blocking layer materials, can effectively improve the luminous efficiency and stability of devices, extend device life.

[0020] It should be noted that, while the potential effects of various groups / features are described separately for ease of explanation, this does not imply that these groups / features function in isolation. In fact, excellent performance is essentially the result of the optimized combination of the entire molecule and the synergistic effects of the various groups, rather than the effects of any single group.

[0021] 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.

[0022] 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.

[0023] In the present invention, the heteroatom in the C3-C60 heteroaryl group as group A is O and / or S. In other heteroaryl groups, unless otherwise specified, the heteroatom in the heteroaryl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatom in the heterocycloalkyl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0024] In the present invention, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0025] In the present invention, "-*" and "*" both represent the attachment site of a group.

[0026] In the present invention, the expression Ca-Cb represents 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.

[0027] In the present invention, “each independently” means that when there are multiple subjects, they may be the same or different.

[0028] In the present invention, the C6-C60 aryl group (preferably C6-C30 aryl group), C6-C28 aryl group, and more preferably C6-C18 aryl group, include monocyclic aryl groups and condensed ring 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 a single bond, illustratively including but not limited to: phenyl, biphenyl, terphenyl, quaterphenyl, etc.; the condensed ring aryl group means that the group contains at least two aromatic rings, and the aromatic rings are The groups that share two adjacent carbon atoms and 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, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, perylene, It should be noted that monocyclic aromatic groups and condensed aromatic groups connected by a single bond also fall within the scope of aromatic groups, such as phenylnaphthyl, naphthylphenyl, binaphthyl, etc.

[0029] The C3-C60 heteroaryl group (preferably a C6-C30 heteroaryl group) and the C3-C23 heteroaryl group include monocyclic heteroaryl groups or condensed-ring heteroaryl groups. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, etc.), the heteroaryl group and the other group are connected by a single bond, and illustratively include but are not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, etc. The fused-ring heteroaryl group refers to 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 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, indolecarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc. It should be noted that heteroaryl groups and heteroaryl groups connected by a single bond, and aryl groups and heteroaryl groups connected by a single bond also fall within the scope of heteroaryl groups, for example, phenyldibenzofuranyl, phenyldibenzothienyl, dibenzofuranylphenyl, dibenzothienylphenyl, etc.

[0030] In the present invention, the C6-C30 arylene group is a divalent group obtained by removing one H atom from the above-mentioned aryl groups; the C3-C30 heteroarylene group is a divalent group obtained by removing one H atom from the above-mentioned heteroaryl groups.

[0031] In the present invention, the C6-C30 aryloxy group is a monovalent group formed by connecting the above-mentioned aryl groups with O. The C3-C30 heteroaryloxy group is a monovalent group formed by connecting the above-mentioned heteroaryl groups with O.

[0032] In the present invention, a specific example of the C6-C30 arylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above-mentioned aryl group. A specific example of the C3-C30 heteroarylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above-mentioned heteroaryl group.

[0033] The C1-C20 straight chain or branched alkyl group, preferably a C1-C16 straight chain or branched alkyl group, further preferably a C1-C10 straight chain or branched alkyl group, and even more preferably a C1-C6 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.

[0034] Specific examples of the C1-C10 alkoxy group include monovalent groups obtained by connecting the above-mentioned linear or branched alkyl groups to O.

[0035] A specific example of the C1-C20 alkylamino group is a monovalent group in which at least one hydrogen atom in -NH2 is replaced by a linear or branched alkyl group as described above. A specific example of the C1-C20 alkylsilyl group is a monovalent group in which at least one hydrogen atom in -SiH3 is replaced by a linear or branched alkyl group as described above.

[0036] The C3-C20 cycloalkyl group, preferably a C3-C10 cycloalkyl group, includes a monocyclic alkyl group or a polycyclic alkyl group. A monocyclic alkyl group refers to an alkyl group containing a single cyclic structure, and a polycyclic alkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more ring carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl groups.

[0037] Specific examples of the C2-C20 heterocycloalkyl group include monovalent groups formed by replacing one of the ring carbon atoms in the above cycloalkyl group with a heteroatom, wherein the heteroatom is preferably N, O or S.

[0038] The C2-C20 alkenyl group, which contains at least one C=C, illustratively includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0039] Preferably, n is 1.

[0040] As a preferred technical solution of the present invention, the organic compound contains one trimethylsilyl group. Compared with compounds containing multiple trimethylsilyl groups, the organic compound containing one trimethylsilyl group has a smaller molecular weight, which is conducive to the formation of a stable amorphous film, making the organic electroluminescent device containing it more stable.

[0041] Preferably, the organic compound has a structure as shown in any one of Formula II-1, Formula II-2, and Formula II-3:

[0042]

[0043] Among them, group A, Ar 1 、Ar 2 、Ar 3 , L 1 , L 2 Has the same definition as Formula I.

[0044] As a preferred technical solution of the present invention, the organic compound contains a trimethylsilyl group, which can be located in group A (Formula II-3), Ar 2 (Formula II-1), Ar 3 (Formula II-2) has a certain resistance in the spatial structure, which further increases the stability of the molecular structure. 3 The trimethylsilyl group on the Ar is further preferably located at the N core of the aromatic amine, thereby making the LUMO energy level of the molecule shallower and affecting the hole migration performance. 2 (Formula II-1), Ar 3 (Formula II-2), more preferably at Ar 2 (Formula II-1).

[0045] Preferably, the organic compound has a structure as shown in Formula II-1 or Formula II-2, and more preferably has a structure as shown in Formula II-1.

[0046] Preferably, the group A is selected from any one of biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, benzofuranyl, and benzothiophenyl, and more preferably biphenyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl.

[0047] Preferably, the organic compound has a structure as shown in any one of Formula III-1, Formula III-2, and Formula III-3: Ar 1 、Ar 2 、Ar 3 , L 1 , L 2 It has the same definition as Formula I; Z is O or S, and the five-membered ring where Z is located is fused with the benzene ring P1 in any feasible manner.

[0048] Preferably, the organic compound has a structure as shown in Formula III-1 or Formula III-2:

[0049]

[0050] Among them, Ar 1 、Ar 2 、Ar 3 , L 1 , L 2It has the same limited scope as formula I; in formula III-1, the benzene ring P2 is fused with the benzene ring P1 in any feasible manner.

[0051] Preferably, the organic compound has a structure as shown in any one of Formula IV-1, Formula IV-2, and Formula IV-3: Ar 1 、Ar 2 、Ar 3 , L 1 , L 2 Having the same limitations as in Formula I; Z is O or S.

[0052] Preferably, the organic compound has a structure as shown in Formula IV-1 or Formula IV-2:

[0053]

[0054] Among them, Ar 1 、Ar 2 、Ar 3 , L 1 , L 2 Has the same definition as Formula I.

[0055] Preferably, the Ar 1 、Ar 2 Each is independently selected from any one of a substituted or unsubstituted C6-C24 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, or C22) aryl group, a substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18) heteroaryl group, and is further preferably any one of a substituted or unsubstituted C6-C18 aryl group, or a substituted or unsubstituted C3-C18 heteroaryl group.

[0056] Preferably, Ar 1 、Ar 2The substituents substituted in the above-mentioned are each independently selected from C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear 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.) alkylsilyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C The present invention further comprises at least one of a C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl group, a C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl group, and more preferably at least one of a C1-C6 straight-chain or branched-chain alkyl group, a cyclohexyl group, a trimethylsilyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a furyl group, a thienyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group and an N-phenylcarbazolyl group.

[0057] Preferably, the Ar 1 、Ar 2 Each is independently selected from any one of the following substituted or unsubstituted groups:

[0058] Among them, -* represents the group and L 1 , L 2 connection site.

[0059] X1, X2, X3 are each independently selected from O, S, CR 11 R 12 or NR 13 Any one of .

[0060] R 11 、R 12 、R 13 Each is independently selected from any one of hydrogen, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight 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, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl; the R 11 and R 12 Not connected or connected to form a ring through chemical bonds.

[0061] Preferably, X2 is selected from O, S or NR 13 Any one of .

[0062] Preferably, X3 is selected from CR11 R 12 or NR 13 .

[0063] Preferably, the R 11 、R 12 、R 13 Each is independently selected from any one of C1-C6 straight-chain or branched alkyl, C2-C6 alkenyl, and C6-C20 aryl, and is more preferably any one of methyl, phenyl, biphenyl, terphenyl, and naphthyl.

[0064] Preferably, the R 11 and R 12 Not connected or connected by chemical bonds to form a spirobifluorenyl group.

[0065] Preferably, the R 13 Any one selected from C6-C20 aryl groups, more preferably any one selected from phenyl, biphenyl, terphenyl, and naphthyl.

[0066] Preferably, the Ar 1 、Ar 2 Each is independently selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, methylfluorenyl, carbazolyl, and N-phenylcarbazolyl.

[0067] Preferably, the Ar 1 、Ar 2 Each is independently selected from any one of the following substituted or unsubstituted groups:

[0068]

[0069]

[0070] Among them, -* represents the group and L 1 , L 2 connection site.

[0071] Preferably, the Ar 3 Any one selected from substituted or unsubstituted C6-C18 (e.g., C6, C9, C10, C12, C14, C16 or C18, etc.) aryl groups, substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) heteroaryl groups, and further preferably any one selected from substituted or unsubstituted C6-C18 aryl groups, substituted or unsubstituted C3-C18 heteroaryl groups.

[0072] Preferably, Ar 3each of the substituents of the substituents described in the substituents is independently selected from at least one of C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched chain 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.) alkylsilyl, 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, further preferably at least one of C1-C6 straight chain or branched chain alkyl, cyclohexyl, trimethylsilyl, phenyl, biphenyl, terphenyl, naphthyl, furanyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl.

[0073] Preferably, the Ar 3 is selected from any one of the following groups which are substituted or unsubstituted:

[0074]

[0075]

[0076] wherein, * represents the connection site of the group.

[0077] Y1, Y3are each independently selected from O, S, CR 14 R 15 or NR 16 .

[0078] Y2is selected from any one of O, S, or NR 17 .

[0079] R 14 , R 15 are each independently selected from any one of hydrogen, C1-C6 (e.g. C2, C3, C4, or C5, etc.) straight chain or branched chain alkyl, further preferably methyl.

[0080] R 16 , R 17Each is independently selected from any one of hydrogen, C1-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, C6-C20 (for example, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, C3-C20 (for example, C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, further preferably any one of C6-C20 aryl, further preferably any one of phenyl, biphenyl, terphenyl, and naphthyl.

[0081] Preferably, the Ar 3 Any one selected from the following substituted or unsubstituted groups:

[0082]

[0083]

[0084] Wherein, -* represents the attachment site of the group.

[0085] Preferably, the Ar 3 Any one selected from the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, methylfluorenyl, carbazolyl, N-phenylcarbazolyl.

[0086] Preferably, the L 1 , L 2 Each is independently selected from any one of a single bond, a substituted or unsubstituted C6-C20 (eg, C6, C9, C10, C12, C14, C16 or C18, etc.) arylene group.

[0087] Preferably, the L 1 , L 2 Each is independently selected from a single bond, a substituted or unsubstituted group: Wherein, -* represents the attachment site of the group.

[0088] Preferably, the L 1 Selected from single bonds, More preferably, a single bond or

[0089] Preferably, the L 2 Select from single bond or A single bond is more preferred.

[0090] More preferably, in the present invention, Ar 1 、Ar 2 、Ar 3 , L 1 , L2 The substituents substituted in the above-mentioned are each independently selected from C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear 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.) alkylsilyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, C3-C20 (e.g., The present invention further preferably comprises any one or a combination of at least two of the following (C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl groups, and further preferably at least one of a C1-C6 straight chain or branched alkyl group, a C3-C6 cycloalkyl group, a trimethylsilyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a furyl group, a thienyl group, a pyrrolyl group, an N-phenylpyrrolyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, an N-phenylindolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, and an N-phenylcarbazolyl group.

[0091] In a preferred technical solution, the organic compound has a structure shown in any one of the following P1-P648:

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120] In a second aspect, the present application provides a use of the organic compound according to the first aspect in an organic electroluminescence device.

[0121] Preferably, the organic compound is used as an electron-blocking layer material and / or a hole-transporting layer material, further preferably an electron-blocking layer material, in an organic electroluminescence device.

[0122] In a third aspect, the present application provides an organic electroluminescence 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 comprising at least one organic compound according to the first aspect.

[0123] Preferably, the organic layer comprises at least one of the organic compounds P1-P648 according to the first aspect.

[0124] In a preferred technical solution, the organic layer comprises an electron-blocking layer, the electron-blocking layer comprising at least one organic compound according to the first aspect, further preferably at least one of the organic compounds P1-P648.

[0125] In another preferred technical solution, the organic layer includes a hole transport layer, and the hole transport layer includes at least one organic compound as described in the first aspect.

[0126] The organic compounds provided by the present invention are particularly suitable as electron blocking layer materials and / or hole transport layer materials, and can significantly improve the luminous efficiency and stability of organic electroluminescent devices, so that the devices have higher luminous efficiency and longer life, and can reduce driving voltage and energy consumption.

[0127] Preferably, the organic layer includes a hole transport region, a light-emitting layer and an electron transport region; the hole transport region includes at least one organic compound as described in the first aspect, and further preferably includes at least one of the organic compounds P1-P648.

[0128] Preferably, the hole transport region includes any one or a combination of at least two of a hole injection layer, a hole transport layer, and an electron blocking layer; the hole transport layer and / or the electron blocking layer include at least one organic compound as described in the first aspect, and further preferably, the electron blocking layer includes at least one organic compound as described in the first aspect.

[0129] 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.

[0130] In a preferred embodiment, the organic electroluminescent device (OLED device) includes a first electrode, a second electrode, and an organic layer located between the electrodes. The organic layer can be divided into multiple regions, such as 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, and further preferably comprises at least one of the organic compounds P1-P648.

[0131] In a preferred technical solution, the organic electroluminescent device includes a first electrode, multiple light-emitting functional layers (organic layers), and a second electrode arranged in sequence; the organic layers include 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, with the hole injection layer in contact with the first electrode (anode). The organic layers (preferably a hole transport layer and / or an electron blocking layer, more preferably an electron blocking layer) comprise at least one organic compound as described in the first aspect, and further preferably include at least one of the organic compounds P1-P648.

[0132] In a preferred embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is made of glass or a polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, the substrate used for the display can also be provided with thin-film transistors (TFTs).

[0133] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode serves as an anode, transparent conductive oxide materials 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 serves as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used, as well as any combination thereof.

[0134] 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, or a combination thereof.

[0135] 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 single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. The hole transport region can also be a multilayer structure comprising at least one of the following: 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.

[0136] In addition to the organic compounds provided by the present invention, the materials of the hole transport region may also include 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 below HT-1 to HT-51; or any combination thereof.

[0137]

[0138]

[0139]

[0140] 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 of the compounds HT-1 to HT-51 described above, or one or more of the compounds HI-1 to HI-3 described below. Alternatively, one or more of the compounds HT-1 to HT-51 can be doped with one or more of the compounds HI-1 to HI-3 described below.

[0141]

[0142] The light-emitting layer includes a luminescent dye (i.e., dopant) that can emit light of different wavelengths and a host material (host). The light-emitting layer can be a single-color light-emitting layer that emits a single color, such as red, green, or blue. Multiple single-color light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or they can be stacked together to form a multi-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.

[0143] Depending on the technology, the light-emitting layer material can be made of fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescence materials, and other materials. An OLED device can use a single light-emitting technology or a combination of multiple technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0144] 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.

[0145]

[0146] 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.

[0147]

[0148]

[0149] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The host material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-85.

[0150]

[0151]

[0152]

[0153]

[0154] In one aspect of the present application, the light-emitting layer employs 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.

[0155]

[0156] wherein D is deuterium.

[0157] In one aspect of the present application, the light-emitting layer employs 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.

[0158]

[0159]

[0160] In one aspect of the present application, the light-emitting layer employs 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 application, the light-emitting layer employs thermally activated delayed fluorescence technology. The host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of PH-1 to PH-85 described above.

[0163] In one aspect of the present application, the light-emitting layer employs thermally activated delayed fluorescence technology. The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of TDE1 to TDE37 listed below.

[0164]

[0165]

[0166]

[0167] The OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode. This region may be a single-layer electron transport layer (ETL), including those containing only one compound and those containing multiple compounds. The region may also be a multilayer structure comprising at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0168] In one aspect of the present invention, an electron blocking layer (EBL) is positioned between the hole transport layer and the light emitting layer. The EBL can be composed of, but is not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described above; or a mixture of, but not limited to, one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

[0169] The OLED organic layer may also include an electron transport region (ETR) between the light-emitting layer and the cathode. This ETR can be a single-layer ETL, including those containing only one compound and those containing multiple compounds. The ETR can also be a multilayer structure comprising at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0170] 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.

[0171]

[0172]

[0173]

[0174]

[0175] In one aspect of the present invention, a hole-blocking layer (HBL) is positioned between the electron-transporting layer and the light-emitting layer. The hole-blocking layer may be composed of, but is not limited to, one or more of the compounds ET-1 to ET-73 described above, or one or more of the compounds PH-1 to PH-46, or a mixture of, but not limited to, one or more of the compounds ET-1 to ET-73 and one or more of the compounds PH-1 to PH-46.

[0176] The device may further 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.

[0177] The present invention further provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0178] Preferably, the display device includes a display screen or a display panel.

[0179] The present invention further provides an electronic device, comprising the aforementioned display device.

[0180] Compared with the prior art, the present invention has the following beneficial effects:

[0181] The organic compound provided by the present invention has a structure as shown in Formula I. Through the design of the molecular structure, it has excellent photoelectric properties, a strong conjugation effect, suitable HOMO and LUMO energy levels, higher hole mobility and stability, which is conducive to reducing the energy barrier and showing excellent electron blocking performance and hole transport performance. The organic compound is applied to organic electroluminescent devices and is suitable as a hole transport layer material and / or an electron blocking layer material, especially suitable for an electron blocking layer material, which can effectively improve the luminous efficiency and stability of the device and extend the device life. DETAILED DESCRIPTION

[0182] The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the embodiments are merely to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0183] In one embodiment, the organic compound has a structure as shown in Formula II-1 and can be prepared by the following representative synthetic route:

[0184]

[0185] In one embodiment, the organic compound has a structure as shown in Formula II-2 and can be prepared by the following representative synthetic route:

[0186]

[0187] In one embodiment, the organic compound has a structure as shown in Formula II-3 and can be prepared by the following representative synthetic route:

[0188]

[0189] In the above synthetic route, groups A, Ar 1 、Ar 2 、Ar 3 , L 1 , L 2 It has the same definition as formula II-1, formula II-2, and formula II-3; Hal1, Hal2, Hal3, Hal4, and Hal5 represent halogen, each independently selected from any one of F, I, Br, and Cl; U1 and U2 are each independently selected from Reaction I, reaction II, and reaction III are carried out in the presence of a palladium catalyst. The order of reaction II and reaction III can be adjusted according to the synthesis situation, that is, reaction II can be carried out first and then reaction III, or reaction III can be carried out first and then reaction II.

[0190] In one embodiment, U1 and U2 are Reaction I is carried out in the presence of tetrakis(triphenylphosphine)palladium Pd(PPh3)4 and potassium carbonate K2CO3.

[0191] In one embodiment, reaction II is performed first, and then reaction III is performed.

[0192] In one embodiment, reaction II 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 t-BuONa.

[0193] In one embodiment, reaction III is carried out in the presence of Pd2(dba)3, tri-tert-butylphosphine (t-Bu)3P and t-BuONa.

[0194] The specific preparation method of the organic compound of the present invention will be described in detail below using a number of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0195] It should be noted that obtaining the organic compound is not limited to the synthesis method and raw materials used in the present invention. Those skilled in the art may also select other methods or routes to obtain the organic compound proposed in the present invention. Organic compounds represented by Formula I synthesized by those skilled in the art using other methods also fall within the scope of protection of the present invention.

[0196] The compounds, solvents and reagents used in the synthesis methods not mentioned in the present invention are all raw materials obtained through commercial channels and can be purchased from the domestic chemical product market or prepared in-house using these raw materials according to known methods.

[0197] The mass spectrometry (m / z) characterization data of the intermediates and target products in the following specific embodiments of the application: The analysis detection uses Agilent HPLC-6500 series Q-TOF liquid chromatograph-mass spectrometer to test the molecular weight, the ionization source uses atmospheric pressure chemical ionization ion source (APCI source), and the ionization method is [M+H] + .

[0198] Synthesis Example 1: Synthesis of organic compound P230

[0199]

[0200] (1) Synthesis of intermediate M1

[0201] In a 1000 mL single-neck flask, 20.00 g of compound M, 11.71 g of phenylboronic acid, 0.93 g of tetrakis(triphenylphosphine)palladium Pd(PPh3)4, 22.81 g of potassium carbonate, 300 mL of toluene, vacuum and nitrogen exchange for 3 times, the reaction is heated to 90°C for 8h. After the reaction is completed, stop the reaction, cool to room temperature, separate the reaction liquid, purify the organic phase by silica gel column twice, concentrate the organic phase, add methanol, reflux and stir for 1h, filter to obtain light yellow powder M1, then recrystallize with ethyl acetate to obtain 24.22 g of pure product.

[0202] M1: m / z theoretical value: 245.12; m / z actual value: 246.11 (APCI source, [M+H] + )。

[0203] (2) Synthesis of intermediate P230-1

[0204] In a 1000 mL single-neck flask, 20.00 g of M1, 22.21 g of 2-bromo-9,9-dimethylfluorene, 1.49 g of tris(dibenzyl ketone)dipalladium(0) Pd2(dba)3, 1.56 g of 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride IPr.HCl, 15.37 g of sodium tert-butoxide t-BuONa, 400 mL of toluene, vacuum and nitrogen exchange for 3 times, the reaction is heated to 90°C for 8h. After the reaction is completed, stop the reaction. Cool to room temperature, separate the reaction liquid, purify the organic phase by silica gel column twice, concentrate the organic phase, add methanol, reflux and stir for 1h, filter to obtain white powder P230-1, then recrystallize with ethyl acetate three times to obtain 28.36 g of pure product.

[0205] P230-1: m / z theoretical value: 437.21; m / z actual value: 438.20 (APCI source, [M+H] + )。

[0206] (3) Synthesis of target product P230

[0207] In a 1000mL single-necked flask, add 20g of P230-1, 14.20g of 4-bromo-trimethylsilylbiphenyl, 0.84g of Pd2(dba)3, 1.25g of tri-tert-butylphosphine (t-Bu)3P, 13.18g of sodium tert-butoxide, and 300mL of toluene. Vacuum and replace with nitrogen three times. Raise the temperature to 110°C and react for 8 hours. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction liquid, and purify the organic phase twice on a silica gel column. Concentrate the organic phase, add methanol, reflux and stir for 1 hour, and filter to obtain a pale yellow powder of P230. This is then recrystallized three times from ethyl acetate to obtain 25.12g of the pure product.

[0208] P230: m / z Calculated: 661.31; m / z Found: 662.32 (APCI source, [M+H] + ).

[0209] Synthesis example 2-20

[0210] The process route of Synthesis Example 2-20 is the same as that of Synthesis Example 1, except that different raw materials are used. The raw materials, target products and characterization data are shown in Table 1. In Table 1, the raw material M is Intermediate M1 represents Raw material D1 represents Br——L 1 ——Ar 1 , raw material D2 represents or Br——L 2 ——Ar 2 .

[0211] Table 1

[0212]

[0213]

[0214]

[0215]

[0216]

[0217] Example 1

[0218] 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 thereof is as follows:

[0219] (1) A glass plate 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;

[0220] (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 10 nm of HT-4:HI-3 (97 / 3, w / w) mixture on the above anode layer as a hole injection layer;

[0221] (3) Vacuum evaporation of 60 nm of compound HT-4 on the hole injection layer as a hole transport layer;

[0222] (4) vacuum evaporating 60 nm of the organic compound P13 provided by the present invention on the hole transport layer as an electron blocking layer;

[0223] (5) Vacuum-deposit 40 nm of a PH-35:RPD-8 (97 / 3, w / w) mixture on the electron-blocking layer as the light-emitting layer;

[0224] (6) Vacuum evaporate 5 nm of ET-23 on the light-emitting layer as a hole blocking layer;

[0225] (7) Vacuum evaporation of 25 nm of a mixture of compounds ET-46:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer;

[0226] (8) Vacuum evaporate 0.5 nm of LiF on the electron transport layer as an electron injection layer;

[0227] (9) Vacuum-evaporating a 150 nm thick layer of aluminum as a cathode on the electron injection layer to obtain the organic electroluminescent device; the total evaporation rate of all organic layers and LiF is controlled at 0.1 nm / s, and the evaporation rate of the metal electrode is controlled at 1 nm / s.

[0228] Examples 2-15, Comparative Examples 1-4

[0229] An organic electroluminescent device, which differs from Example 1 only in that the organic compound P13 used as the material of the electron blocking layer in step (4) is replaced by the organic compound in Table 2.

[0230] The structures of the electron blocking layer materials of Comparative Examples 1-4 are as follows:

[0231]

[0232] The performance test of the organic electroluminescent device is carried out as follows:

[0233] (1) The driving voltage and current efficiency of the organic electroluminescent device were determined using a digital source table and a luminance meter at the same brightness; specifically, the current density when the brightness of the organic electroluminescent device reached 3000 cd / m 2 was determined by increasing the voltage at a rate of 0.1 V per second, and the ratio of the brightness to the current density was the current efficiency;

[0234] (2) The LT97 lifetime test was as follows: using a luminance meter, the time when the brightness of the organic electroluminescent device decreased to 2910 cd / m 2 at a constant current at 3000 cd / m 2 was measured;

[0235] The test value of the LT97 lifetime of Comparative Example 1 was taken as 1.0, and the ratio of the test value of the LT97 lifetime of other devices to the test value of Comparative Example 1 was calculated; the test results are shown in Table 2:

[0236] Table 2

[0237] Device electron blocking layer <![CDATA[要求亮度(cd / m 2 )]]> Current efficiency (cd / A) LT97 lifespan Comparative Example 1 CCP-1 3000 21.6 1 Comparative Example 2 CCP-2 3000 22.9 1.1 Comparative Example 3 CCP-3 3000 22.8 1.2 Comparative Example 4 CCP-4 3000 20.5 0.9 Example 1 P13 3000 24.3 1.5 Example 2 P136 3000 24.8 1.4 Example 3 P221 3000 24.6 1.3 Example 4 P230 3000 24.5 1.5 Example 5 P232 3000 25.2 1.3 Example 6 P398 3000 24.6 1.5 Example 7 P461 3000 24.2 1.3 Example 8 P477 3000 23.9 1.4 Example 9 P553 3000 23.8 1.4 Example 10 P581 3000 23.7 1.3 Example 11 P224 3000 24.1 1.4 Example 12 P219 3000 24.6 1.3 Example 13 P444 3000 23.9 1.4 Example 14 P590 3000 24.5 1.5 Example 15 P635 3000 24.3 1.4

[0238] According to the performance data in Table 2, the organic compound provided by the application can effectively improve the current efficiency, stability and lifetime of the organic electroluminescent device, and the current efficiency of the red light device reaches 23.7-25.2 cd / A, and the lifetime is 1.3-1.5 times that of the comparative material, which is an excellent electron blocking material.

[0239] Specifically, the difference between CCP-1 in Comparative Example 1 and the organic compound P230 provided by the application is that the group A in CCP-1 is fluorenyl, the molecular weight is large, there is a certain steric hindrance between the two methyl groups and the N atom, and the hole mobility is low, resulting in low current efficiency and short lifetime of the device using CCP-1. The group A of compound CCP-2 is phenyl, and compared with P232 of the application, the conjugation effect of the N atom on CCP-2 is reduced, and the hole mobility is reduced, resulting in poor performance of the device of Comparative Example 2. Compared with P461 of the application, the naphthyl group connected to the arylamine N of CCP-3 compound is substituted with other phenyl groups, and the molecular weight of CCP-3 is large, the temperature is high during device evaporation, and the device performance is poor. The group A of CCP-4 compound contains an N atom, which has strong electron-withdrawing ability, which reduces the electron cloud density of the arylamine N atom, which is not conducive to hole transfer, resulting in low current efficiency and short lifetime of the device using CCP-4.

[0240] Example 16

[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 preparation method thereof is as follows:

[0242] (1) A glass plate 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;

[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 10 nm of HT-4:HI-3 (97 / 3, w / w) mixture on the above anode layer as a hole injection layer;

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

[0245] (4) vacuum evaporating 35 nm of the organic compound P158 provided by the present invention on the hole transport layer as an electron blocking layer;

[0246] (5) Vacuum-deposit 40 nm of a ternary mixture of PH-61:PH-3:GPD-12 (100:100:20, w / w) on the electron blocking layer as the light-emitting layer;

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

[0248] (7) Vacuum evaporation of 25 nm of a mixture of compounds ET-69:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer;

[0249] (8) Vacuum evaporate 1 nm of LiF on the electron transport layer as an electron injection layer;

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

[0251] Examples 17-30, Comparative Examples 5-8

[0252] An organic electroluminescent device, which differs from Example 16 only in that the organic compound P158 used as the material of the electron blocking layer in step (4) is replaced by the organic compound in Table 3.

[0253] The structures of the electron blocking layer materials of Comparative Examples 5-8 are as follows:

[0254]

[0255] The performance test of the organic electroluminescent device is carried out as follows:

[0256] (1) Under the same brightness, use a digital source meter and a luminance meter to measure the driving voltage and current efficiency of the organic electroluminescent device; specifically, increase the voltage at a rate of 0.1V per second and measure the current efficiency when the brightness of the organic electroluminescent device reaches 10000cd / m 2 The current density at this time, the ratio of brightness to current density is the current efficiency;

[0257] (2) The LT97 life test is as follows: Use a luminance meter at 10000cd / m 2 Under the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to be reduced to 9700cd / m 2 time;

[0258] The LT97 life test value of Comparative Example 5 was recorded as 1.0, and the ratio of the LT97 life test values ​​of other devices to the test value of Comparative Example 5 was calculated. The test results are shown in Table 3:

[0259] Table 3

[0260]

[0261]

[0262] Combined with the performance data in Table 3, it can be seen that the organic compounds provided by the present invention can be used in organic electroluminescent devices to effectively improve the current efficiency, stability and lifespan, so that the current efficiency of green light devices reaches 62.5-65.9 cd / A and the lifespan reaches 1.4-1.7 times that of the comparative materials, making them excellent electron blocking materials.

[0263] Specifically, the difference between CCP-5 in Comparative Example 5 and the organic compound P158 of the present invention is that the diortho-substituted group of the group A connected to the N of CCP-5, one of the groups has a large molecular weight, the molecular torsional tension is too large, the conjugation is reduced, and the hole mobility is reduced, resulting in low current efficiency and short life of the device using CCP-5. Compared with P530 of the present invention, the carbazole structure of compound CCP-6 is located in the para position of the site where the N atom is located, and the conjugation effect of the aromatic amine N atom is small, the hole mobility of the molecule is reduced, resulting in poor efficiency and short life of the device using CCP-6. Compared with compound P549 of the present invention, the Ar in CCP-7 2The molecular weight is too large, resulting in a high molecular sublimation temperature, and the device current efficiency of CCP-7 is low and the life is short. Compared with P249 of the present invention, CCP-8 has Ar 2 The molecular weight is too large, resulting in a high molecular sublimation temperature, and the current efficiency of the device using CCP-8 is low and the life is short.

[0264] In summary, the organic compound provided by the present invention is a type of electron blocking layer material with good performance, which can be applied to red light devices and green light devices, and can effectively improve the luminous efficiency of the devices and extend their service life.

[0265] The applicant states that while the present invention uses the aforementioned embodiments to illustrate the organic compounds, their applications, and organic electroluminescent devices containing the same, the present invention is not limited to these embodiments. This does not necessarily mean that the present invention must rely on these embodiments for implementation. Those skilled in the art will understand that any improvements to the present invention, equivalent substitutions for raw materials in the products of the present invention, additions of auxiliary components, and selection of specific methods, etc., fall within the scope of protection and disclosure of the present invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in Formula I: Wherein, group A is selected from any one of unsubstituted or trimethylsilyl-substituted biphenyl, unsubstituted or trimethylsilyl-substituted naphthyl, substituted or unsubstituted C3-C60 O-containing heteroaryl, and substituted or unsubstituted C3-C60 S-containing heteroaryl; Ar 1 、Ar 2 Each is independently selected from any one of a substituted or unsubstituted C6-C28 aryl group and a substituted or unsubstituted C3-C23 heteroaryl group; Ar 3 Any one selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein the attachment site of Ar3 is the ortho position of the attachment site of the N atom on the group A; L 1 、L 2 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; The substituted substituents are each independently selected from at least one of a C1-C20 straight or branched alkyl group, a C3-C20 cycloalkyl group, a C2-C20 heterocycloalkyl group, a C2-C20 alkenyl group, a C1-C10 alkoxy group, a carboxyl group, a nitro group, a cyano group, an amino group, a hydroxyl group, a thiol group, a C1-C20 alkylsilyl group, a C1-C20 alkylamino group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 aryloxy group, a C3-C30 heteroaryloxy group, a C6-C60 aryl group, and a C3-C60 heteroaryl group; The substituent includes a trimethylsilyl group, and n represents the number of trimethylsilyl groups in the organic compound, and n is an integer selected from 1-3.

2. The organic compound according to claim 1, 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, group A, Ar 1 、Ar 2 、Ar 3 、L 1 、L 2 Having the same limited scope as Formula I; Preferably, the organic compound has a structure as shown in Formula II-1.

3. The organic compound according to claim 2, characterized in that The group A is selected from any one of biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, benzofuranyl and benzothiophenyl.

4. The organic compound according to claim 1 or 2, characterized in that The organic compound has a structure as shown in Formula III-1 or Formula III-2: Among them, Ar 1 、Ar 2 、Ar 3 , L 1 , L 2 Having the same limited scope as Formula I; In formula III-1, the benzene ring P2 is fused to the benzene ring P1 in any feasible manner.

5. The organic compound according to claim 1 or 2, characterized in that The organic compound has a structure as shown in Formula IV-1 or Formula IV-2: Among them, Ar 1 、Ar 2 、Ar 3 、L 1 、L 2 It has the same definition as Formula I.

6. The organic compound according to any one of claims 1 to 5, characterized in that The Ar 1 、Ar 2 Each is independently selected from any one of a substituted or unsubstituted C6-C24 aryl group and a substituted or unsubstituted C3-C20 heteroaryl group, preferably any one of a substituted or unsubstituted C6-C18 aryl group and a substituted or unsubstituted C3-C18 heteroaryl group; Preferably, Ar 1 、Ar 2 The substituted substituents are each independently selected from at least one of a C1-C10 straight or branched alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkylsilyl group, a C6-C20 aryl group, and a C3-C20 heteroaryl group.

7. The organic compound according to any one of claims 1 to 5, characterized in that The Ar 1 、Ar 2 Each is independently selected from any one of the following substituted or unsubstituted groups: Among them, -* represents the group and L 1 , L 2 The attachment site; X1, X2, X3 are each independently selected from O, S, CR 11 R 12 or NR 13 Any of the following; R 11 、R 12 、R 13 Each is independently selected from any one of hydrogen, C1-C10 straight or branched alkyl, C2-C10 alkenyl, C6-C20 aryl, and C3-C20 heteroaryl; the R 11 and R 12 Not connected or connected to form a ring through chemical bonds; Preferably, X2 is selected from O, S or NR 13 Any of the following; Preferably, X3 is selected from CR 11 R 12 or NR 13 ; Preferably, the R 11 、R 12 、R 13 Each is independently selected from any one of C1-C6 straight or branched alkyl, C2-C6 alkenyl, and C6-C20 aryl.

8. The organic compound according to any one of claims 1 to 5, characterized in that The Ar 1 、Ar 2 Each is independently selected from any one of the following substituted or unsubstituted groups: Among them, -* represents the group and L 1 , L 2 connection site.

9. The organic compound according to any one of claims 1 to 5, characterized in that The Ar 3 Any one selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C30 heteroaryl, preferably any one selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl; Preferably, Ar 3 The substituted substituents are each independently selected from at least one of a C1-C10 straight or branched alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkylsilyl group, a C6-C20 aryl group, and a C3-C20 heteroaryl group.

10. The organic compound according to any one of claims 1 to 5, characterized in that The Ar 3 Any one selected from the following substituted or unsubstituted groups: Wherein, -* represents the attachment site of the group; Y1 and Y3 are each independently selected from O, S, CR 14 R 15 or NR 16 Any of the following; Y2 is selected from O, S or NR 17 Any of the following; R 14 、R 15 Each is independently selected from any one of hydrogen, C1-C6 straight chain or branched alkyl; R 16 、R 17 Each is independently selected from any one of hydrogen, C1-C10 linear or branched alkyl, C6-C20 aryl, and C3-C20 heteroaryl.

11. The organic compound according to any one of claims 1 to 5, characterized in that The Ar 3 Any one selected from the following substituted or unsubstituted groups: Wherein, -* represents the attachment site of the group.

12. The organic compound according to any one of claims 1 to 5, characterized in that The L 1 、L 2 Each is independently selected from any one of a single bond, a substituted or unsubstituted C6-C20 arylene group; Preferably, the L 1 、L 2 Each is independently selected from a single bond, a substituted or unsubstituted group: Wherein, -* represents the attachment site of the group.

13. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in any one of the following P1-P648:

14. Use of the organic compound according to any one of claims 1 to 13, characterized in that: The organic compound is applied to an organic electroluminescent device; Preferably, the organic compound is used as an electron blocking layer material and / or a hole transport layer material in an organic electroluminescent device, and more preferably as an electron blocking layer material.

15. 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 13.

16. The organic electroluminescent device according to claim 15, characterized in that: The organic layer includes an electron blocking layer, and the electron blocking layer includes at least one organic compound according to any one of claims 1 to 13.

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