Organic compound and use thereof

Abstract

An organic compound and a use thereof. The organic compound, by means of the design of the molecular structure thereof, has excellent optoelectronic properties and suitable HOMO and LUMO energy levels, with high hole mobility and good stability, and is capable of exhibiting excellent electron-blocking performance and hole-transport performance. The organic compound is applied in an organic electroluminescent device and is suitable for use as a hole transport layer material and / or an electron blocking layer material, and can effectively improve the luminous efficiency and stability of the device, extend the device lifetime, and reduce voltage and energy consumption.

Description

An organic compound and application thereof TECHNICAL FIELD

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

[0002] In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them well suited for manufacturing on flexible substrates, allowing for the design and production of aesthetically pleasing and diverse optoelectronic products with advantages unmatched by inorganic materials. Examples of such organic optoelectronic devices include organic light emitting diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, etc.; among which the development of OLEDs is particularly rapid and has achieved commercial success in the field of information display. OLEDs can provide high saturation of red, green, and blue colors, and full-color display devices made therefrom do not require additional backlights, have colorful, light, and soft advantages.

[0003] The core of an OLED device is a thin film structure containing various organic functional materials. Common organic functional materials include hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, light-emitting host materials, and light-emitting guest materials (dyes), etc. When powered on, electrons and holes are injected and transported to the light-emitting region and recombine there, generating excitons and emitting light.

[0004] Researchers have developed a variety of organic materials that, in combination with various device structures, can improve carrier mobility, regulate carrier balance, break through electroluminescent efficiency, and delay device decay. According to the light-emitting mechanism of the material, OLED devices can be broadly divided into fluorescent light-emitting, phosphorescent light-emitting, thermally activated delayed fluorescence, and thermally activated sensitized fluorescence, etc. Due to quantum mechanical reasons, common fluorescent emitters mainly utilize 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 utilize both triplet and singlet excitons for light emission, known as phosphorescent emitters, and their energy conversion efficiency can be up to 4 times higher than that of traditional fluorescent emitters. The thermally activated delayed fluorescence (TADF) technology promotes the transition of triplet excitons to singlet excitons, allowing for efficient utilization of triplet excitons without the use of metal complexes to achieve high light-emitting efficiency. The thermally activated sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize emitters through energy transfer, also achieving high light-emitting efficiency.

[0005] Materials with hole transport properties have a significant influence on the performance of OLED devices of various light-emitting mechanisms, and the organic functional layer formed by such materials is located between the anode and the light-emitting layer of the device, which plays a role of hole injection and transport, and regulates the transport balance of carriers. With the gradual entry of OLED products into the market, people have higher and higher requirements for display effects and device performance, and the current OLED materials cannot completely solve the problems of OLED product efficiency, service life, cost and the like, and the performance of hole transport materials still has a great room for improvement. Therefore, more types of organic materials with higher performance are urgently needed in the art to improve the performance of OLED devices, so that the devices have higher luminous efficiency and service life, lower voltage and energy consumption. SUMMARY

[0006] In view of the deficiencies of the prior art, the purpose of the present disclosure is to provide an organic compound and its application, which has high hole mobility and can play an excellent hole transport and electron blocking role through the design of the molecular structure, and is used in an organic electroluminescent device, which can improve the luminous efficiency and service life of the device and reduce the voltage.

[0007] To achieve this purpose, the present disclosure adopts the following technical solutions:

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

[0009] In Formula I, L 1 , L 2 are each independently selected from any one of a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, and the L 2 is not

[0010] In Formula I, Ar 1 is selected from any one of a C6-C18 monocyclic aryl residue of m+1 valence, a C10-C14 fused aryl residue of m+1 valence.

[0011] In Formula I, Ar 2 is selected from any one of a substituted or unsubstituted n+1 valence C6-C30 aryl residue, a substituted or unsubstituted n+1 valence C3-C30 heteroaryl residue.

[0012] In Formula I, R 1 is selected from any one of a methyl group, an isopropyl group, a C6-C18 monocyclic aryl group, a C10-C14 fused aryl group, a C1-C20 alkoxy group, a C3-C20 cycloalkyl group, a C2-C20 heterocycloalkyl group, or a cyano group.

[0013] In Formula I, X is selected from single bonds, O, S, or CR. 13 R 14 Any one of the following; when X is a single bond, it indicates that the ring it belongs to is a five-membered ring, thereby forming a fluorene derivative group; when X is O, S, or CR 13 R 14 When any one of the following is true, the ring it belongs to is a six-membered ring.

[0014] R 2 R 13 R 14 Each is independently selected from any one of substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroaryl groups.

[0015] R 3 R 4 R 11 R 12 Each is independently selected from any one of substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, or substituted or unsubstituted C3-C20 cycloalkyl groups.

[0016] In formula I, m and n represent substituents R, respectively. 1 R 2 The number of substituents, m and n, are each independently selected from integers ≥ 0, that is, from 0 to the maximum number of substitutable substituents, such as 0, 1, 2, 3, or 4; the upper limit of m is the number of substituents R allowed by the chemical environment. 1 The maximum number of substituents R; the upper limit of n is the number of substituents R allowed by the chemical environment. 2 The maximum number.

[0017] It should be noted that when m is 0, it indicates that the substituent R 1 Ar does not exist. 1 There are no substituents (H) on Ar 1 It is a monovalent group. When m is 1, Ar 1 It has one R group attached to it. 1 R 1 Can be connected to Ar 1 Ar can be placed at any site permitted by the chemical environment. 1 It is a divalent group (i.e., C6-C18 monocyclic arylene, C10-C14 fused arylene). When m≥2, multiple (≥2) R 1 These are groups that are the same as or different from each other. Similarly, for the sake of simplicity, we will not go into detail about n.

[0018] In formula I, p and q represent substituents R, respectively. 3 R 4each of p and q is independently selected from an integer from 0 to 5, for example, can be 0, 1, 2, 3, 4, or 5; when p≥2, the multiple (≥2) R 3 are the same or different groups. For the sake of brevity, q will not be repeated here.

[0019] In formula I, r is 0 or 1; when r is 0, it represents L 2 is absent, the N atom is directly connected to one side benzene ring of the fused ring where X is located through a single bond.

[0020] In formula I, s is 0 or 1; when s is 0, it represents Ar 2 is absent, the N atom is directly connected to one side benzene ring of the fused ring where X is located through a single bond. 2 (If any, that is, if n>0) is directly connected to one side benzene ring of the fused ring where X is located through a single bond.

[0021] In formula I, r+s≥1.

[0022] L 1 , L 2 , R 2 , R 3 , R 4 , R 11 , R 12 , R 13 , R 14 The substituents of the substituents described in the above-mentioned substituents are each independently selected from at least one of C1-C20 straight chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 alkoxy, cyano, C2-C20 alkenyl, C6-C60 aryl, C3-C60 heteroaryl.

[0023] In the present disclosure, the “substituted or unsubstituted” group can be substituted with one substituent or can be substituted with multiple substituents, when the substituents are multiple (at least 2), they can be the same or different substituents; when the same expression is involved below, it has the same meaning. If not otherwise specified, the selection range of the substituents is as shown above, which will not be repeated here.

[0024] The organic compound provided by the present disclosure has the structure shown in formula I. The three ends connected to N in the arylamine structure have long conjugated chains and small steric hindrance, which is conducive to the improvement of hole mobility, the reduction of device voltage, and the improvement of efficiency. Through molecular design, the structure can have a wide band gap, which is conducive to hole transfer, reduces the injection barrier, avoids the aggregation of holes between organic layers, and affects the service life. On the other hand, the shallow LUMO level can prevent electrons and triplet excitons from entering the electron blocking layer, thereby prolonging the service life of the device. Moreover, the three-ring fused structure where X is located in the molecular structure is conducive to the further improvement of hole mobility, and the alkyl R 11 , R 12The organic compound has excellent photoelectric properties, high hole mobility and good stability, can play excellent electron blocking effect and hole transport effect, and is suitable for being used as a hole transport layer material and / or an electron blocking layer material in an organic electroluminescent device, can effectively improve the luminous efficiency and stability of the device, prolong the service life of the device, and reduce the voltage and energy consumption.

[0025] It should be noted that in the present disclosure, the possible effects of each group / feature are described separately for the sake of explanation, but this does not mean that these groups / features act independently. In fact, the reason for good performance is essentially the optimized combination of the whole molecule, which is the result of the synergistic effect between various groups, rather than the effect of a single group.

[0026] The following is a preferred technical solution of the present disclosure, but is not a limitation on the technical solutions provided by the present disclosure. Through the following preferred technical solution, the purpose and beneficial effects of the present disclosure can be better achieved and realized.

[0027] In the present disclosure, the description of chemical elements, if no special explanation, contains the concept of isotopes with the same chemical properties, for example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0028] In the present disclosure, if no special explanation, the heteroatoms in the heteroaryl group are selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatoms in the heterocycloalkyl group are selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0029] In the present disclosure, the expression of the ring structure with “—” indicates that the connection site is at any position on the ring structure that can form a bond.

[0030] In the present disclosure, “-*” and “*” both represent the connection site of the group.

[0031] In the present disclosure, the expression of Ca-Cb represents that the number of carbon atoms of the group is a-b, and if no special explanation, the number of carbon atoms does not include the number of carbon atoms of the substituent.

[0032] The C6-C30 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0033] The C3-C30 can each be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.

[0034] The C6-C18 can each be C6, C9, C10, C12, C14, C16, C18, etc.

[0035] The C10-C14 can each be C10, C11, C12, C13, C14.

[0036] The C1-C20 can each be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, or C19, etc.

[0037] The C3-C20 can each be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, or C19, etc.

[0038] The C2-C20 can each be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, or C19, etc.

[0039] The C6-C60 can each 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.

[0040] The C3-C60 can each be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.

[0041] In the present disclosure, "each independently" means that the subject thereof has multiple, which can be the same or different from each other.

[0042] Unless otherwise specified, in this disclosure, the C6-C60 aryl and C6-C30 aryl groups include monocyclic aryl and fused-ring aryl groups; a 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 linked by single bonds, including but not limited to: phenyl, biphenyl, terphenyl, tetraphenyl, etc.; a fused-ring aryl group means that the group contains at least two aromatic rings, and the aromatic rings share two adjacent carbon atoms. Groups with mutually fused atoms, exemplary examples include but are not limited to: naphthyl, anthraceneyl, phenanthryl, indene, fluorenyl and their 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, spirodifluorenyl, benzo[a]fluorenyl, etc.), fluoranthraceneyl, triphenylene, pyrene, perylene, Aryl, tetraphenyl, acenaphthenyl, benzo[a]acenaphthenyl, etc. It should be noted that monocyclic aryl and fused-ring aryl groups linked by single bonds also fall under the category of aryl groups, such as phenylnaphthyl, naphthylphenyl, and binaphthyl.

[0043] In this disclosure, Ar 1 R 1 The C6-C18 monocyclic aryl group mentioned herein refers to a group containing 1-3 phenyl groups. When it contains at least 2 phenyl groups, the phenyl groups are linked by single bonds, for example: phenyl, biphenyl, terphenyl.

[0044] In this disclosure, Ar 1 R 1 The C10-C14 fused aryl groups described herein are understood to be groups containing at least two phenyl groups fused together via a common edge (chemical bond), such as naphthalene, anthracene, phenanthrene, etc. It should be noted that fluorene and its derivative groups (e.g., dimethylfluorene, diphenylfluorene, spirodifluorene, etc.) are not fused aryl groups in the sense of this disclosure, because the two phenyl groups in fluorene do not share a common edge.

[0045] In the present disclosure, the C3-C60 heteroaryl group, C6-C30 heteroaryl group, includes a monocyclic heteroaryl group or a fused ring heteroaryl group. The monocyclic heteroaryl group means a group containing at least one heteroaryl group in a molecule, and when a molecule contains one heteroaryl group and other groups (e.g., aryl group, heteroaryl group, etc.), the heteroaryl group and the other groups are connected by a single bond, and exemplarily includes, but is not limited to, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, furanyl group, thienyl group, pyrrolyl group, bipyridyl group, phenylpyridyl group, pyridylphenyl group, 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 a molecule, and the two are fused to each other by sharing two adjacent atoms, and exemplarily includes, but is not limited to, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, benzofuranyl group, benzothienyl group, isobenzofuranyl group, isobenzothienyl group, indolyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group and its derivatives (N-phenylcarbazolyl group, N-naphthylcarbazolyl group, benzocarbazolyl group, diphenylcarbazolyl group, indolocarbazolyl group, azacarbazolyl group, etc.), acridinyl group, phenothiazinyl group, phenoxazinyl group, hydrogenated acridinyl group, etc. It should be noted that a heteroaryl group connected by a single bond and a heteroaryl group, an aryl group connected by a single bond and a heteroaryl group also belong to the scope of the heteroaryl group, such as phenyldibenzofuranyl group, phenyldibenzothienyl group, dibenzothienylphenyl group, dibenzofuranylphenyl group, etc.

[0046] In the present disclosure, specific examples of the C6-C30 arylene group are 2-valent groups that can be obtained by removing one hydrogen from the above-mentioned aryl group. Specific examples of the C3-C30 heteroarylene group are 2-valent groups that can be obtained by removing one hydrogen from the above-mentioned heteroaryl group.

[0047] The C1-C20 linear or branched alkyl group, preferably C1-C16 linear or branched alkyl group, and more preferably C1-C10 linear or branched alkyl group, exemplarily includes, but is not limited to, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, 2-methylbutyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, neohexyl group, 2-ethylhexyl group, n-octyl group, n-heptyl group, n-nonyl group, n-decyl group, etc.

[0048] Specific examples of the C1-C20 alkoxy group are 1-valent groups that can be obtained by connecting the above-mentioned linear or branched alkyl group with O.

[0049] The C3-C20 cycloalkyl group, preferably C3-C10 cycloalkyl group, includes a monocyclic cycloalkyl group or a polycyclic cycloalkyl group. The monocyclic cycloalkyl group means an alkyl group containing a single ring structure, and the polycyclic cycloalkyl group means a structure in which two or more cycloalkyl groups are connected by sharing one or more carbon atoms in the ring; exemplarily includes, but is not limited to, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, adamantyl group, etc.

[0050] Specific examples of the C2-C20heterocycloalkyl group can be mentioned as a group in which at least one C atom in the aforementioned cycloalkyl groups is replaced by a heteroatom (e.g., N, O, S, etc.) to form a group, exemplarily including, but not limited to, an epoxy group, an oxetanyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, a tetrahydropyrrolyl group, a tetrahydropyranyl group, a piperidinyl group, a piperazinyl group, a dioxanyl group, a morpholinyl group, etc.

[0051] The C2-C20alkenyl group, preferably C2-C10alkenyl group, wherein at least one C=C is included, exemplarily includes, but is not limited to, a vinyl group, a propenyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, a butadienyl group, a pentadienyl group, etc.

[0052] Preferably, the organic compound has a structure as shown in any one of Formula II-1, Formula II-2, Formula II-3:

[0053] wherein, L 1 , L 2 , Ar 1 , Ar 2 , R 1 , R 2 , R 3 , R 4 , R 11 , R 12 , m, n, p, q have the same defined range as Formula I.

[0054] Preferably, the L 2 is selected from any one of a substituted or unsubstituted C6-C20(e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylene group, a substituted or unsubstituted C3-C20(e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroarylene group, and is not

[0055] Preferably, the L 2 is selected from any one of a substituted or unsubstituted C6-C20(e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylene group, a substituted or unsubstituted C3-C20(e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroarylene group, and is not wherein, —* represents a connecting site of the group.

[0056] Y1is selected from any one of O, S, NR 21 , or CR 22 R 23 .

[0057] R 21 , R 22 , R 23each independently selected from any one of C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C6-C30 aryl, or C3-C30 heteroaryl; said R 22 and R 23 are not connected or are connected by a chemical bond into a ring.

[0058] Preferably, said R 21 , R 22 , R 23 each independently is 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.) linear 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, further preferably C1-C6 linear or branched alkyl, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, and still further preferably methyl or phenyl.

[0059] Preferably, said R 32 and R 33 are not connected or are connected by a chemical bond into a spirofluorene group.

[0060] Preferably, L 2 is selected from any one of a substituted or unsubstituted C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 alkoxy, cyano, further preferably at least one of 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, and more preferably at least one of methyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclohexyl.

[0061] Preferably, said L 2 is selected from any one of a substituted or unsubstituted C6-C20 (e.g. C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylene, substituted or unsubstituted C3-C20 (e.g. C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroarylene. wherein — * represents the site of attachment of the group.

[0062] Preferably, said L 1 is selected from any one of a substituted or unsubstituted C6-C20 (e.g. C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylene, substituted or unsubstituted C3-C20 (e.g. C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroarylene.

[0063] Preferably, the L 1 is selected from any one of the following groups, which are substituted or unsubstituted:

[0064] wherein -* represents the site of attachment of the group.

[0065] Y2is selected from O, S, NR 31 or CR 32 R 33 is selected from any one of the following groups, which are substituted or unsubstituted:

[0066] R 31 , R 32 , R 33 are each independently selected from any one of C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C6-C30 aryl or C3-C30 heteroaryl; the R 32 and R 33 are not connected or are connected by a chemical bond into a ring.

[0067] R 34 is selected from any one of hydrogen, C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C6-C30 aryl or C3-C30 heteroaryl.

[0068] Preferably, the R 31 , R 32 , R 33 , R 34 are each 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.) linear or branched alkyl, C6-C20 (e.g. C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, further preferably C1-C6 linear or branched alkyl, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, and still further preferably methyl or phenyl.

[0069] Preferably, the R 32 and R 33 are not connected or are connected by a chemical bond into a spirofluorene group.

[0070] Preferably, L 1each of the substituents of the substituents mentioned in the substituents is independently selected from at least one of C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 alkoxy, further preferably at least one of C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl, C3-C10 (e.g. C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C2-C10 (e.g. C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy.

[0071] Preferably, the L 1 is selected from any one of the following groups:

[0072] wherein - * represents the point of attachment of the group.

[0073] Preferably, the Ar 1 is selected from any one of the following groups: wherein - * represents the point of attachment of the group Ar 1 to L 1 .

[0074] Preferably, the R 1 is selected from any one of methyl, isopropyl, phenyl, naphthyl, biphenyl, C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, cyano, C3-C10 (e.g. C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, or C2-C10 (e.g. C3, C4, C5, C6, C7, C8, C9, etc.) heterocycloalkyl, further preferably any one of methyl, isopropyl, phenyl, naphthyl, biphenyl, methoxy, cyclohexyl, tetrahydrofuranyl, tetrahydropyranyl.

[0075] Preferably, the m is selected from an integer from 0 to 2.

[0076] Preferably, the Ar 2 is selected from any one of the following groups:

[0077] wherein - * represents the point of attachment of the group; in particular the group Ar 2 to L in formula I.

[0078] Y3, Y4are each independently selected from O, S, NR 41 or CR 42 R43 any one of the following: H, C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C6-C30 aryl, or C3-C30 heteroaryl.

[0079] R 41 , R 42 , R 43 each independently is selected from any one of the following: C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C6-C30 aryl, or C3-C30 heteroaryl; said R 42 and R 43 are not connected or are connected by a chemical bond into a ring.

[0080] R 44 is selected from any one of the following: H, C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C6-C30 aryl, or C3-C30 heteroaryl.

[0081] Preferably, said R 41 , R 42 , R 43 , R 44 each independently is selected from any one or a combination of at least two of the following: C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, further preferably C1-C6 linear or branched alkyl, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, and still further preferably methyl or phenyl.

[0082] Preferably, said R 42 and R 43 are not connected or are connected by a chemical bond into a spirofluorene group.

[0083] Preferably, said Ar 2 is selected from any one of the following groups: wherein —* represents the point of attachment of the group.

[0084] Preferably, said R 2 is selected from any one of the following: C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, further preferably methyl, isopropyl, t-butyl, isobutyl, t-amyl, phenyl, naphthyl, or biphenyl.

[0085] Preferably, said n is selected from an integer from 0 to 2.

[0086] Preferably, said R11 , R 12 each independently is selected from any one of C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched chain alkyl, further preferably methyl.

[0087] Preferably, said X is selected from a single bond, O, S or CR 13 R 14 each independently is selected from any one of C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched chain alkyl, C6-C20 (e.g. C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl. 13 , R 14 each independently is selected from any one of C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched chain alkyl, C6-C20 (e.g. C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl.

[0088] Preferably, said R 13 , R 14 each independently is selected from any one of C1-C6 straight chain or branched chain alkyl, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, further preferably methyl or phenyl.

[0089] Preferably, said X is a single bond or O.

[0090] Preferably, said R 3 , R 4 each independently is selected from any 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, further preferably methyl, isopropyl, tert-butyl, isobutyl, tert-amyl or cyclohexyl.

[0091] Preferably, said p, q are each independently 0 or 1.

[0092] Preferably, said organic compound has a structure according to any one of P1-P400:

[0093] In a second aspect, the present disclosure provides an application of the organic compound according to the first aspect to an organic electroluminescence device.

[0094] Preferably, the organic compound is used as an electron blocking layer material and / or a hole transport layer material, further preferably an electron blocking layer material, in the organic electroluminescence device.

[0095] In a third aspect, the present disclosure 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.

[0096] Preferably, the organic layer comprises at least one of the organic compounds P1-P400 according to the first aspect.

[0097] 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-P400.

[0098] In another preferred technical solution, the organic layer comprises a hole transport layer, the hole transport layer comprising at least one organic compound according to the first aspect, further preferably at least one of the organic compounds P1-P400.

[0099] The organic compound provided by the present disclosure is particularly suitable as an electron blocking layer material and / or a hole transport layer material, especially as an electron blocking layer material, and is particularly suitable for red organic electroluminescence devices, which can significantly improve the luminous efficiency and stability of the organic electroluminescence device, make the device have higher luminous efficiency and longer service life, and reduce the driving voltage and energy consumption.

[0100] Preferably, the organic layer comprises a hole transport zone, a light-emitting layer, and an electron transport zone; the hole transport zone comprising at least one organic compound according to the first aspect, further preferably at least one of the organic compounds P1-P400.

[0101] Preferably, the hole transport zone comprises 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 comprising at least one organic compound according to the first aspect, further preferably the electron blocking layer comprising at least one organic compound according to the first aspect.

[0102] Preferably, the electron transport zone comprises any one or a combination of at least two of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0103] In a preferred embodiment, the organic electroluminescent device (OLED device) comprises a first electrode and a second electrode, and an organic layer between the electrodes. The organic layer can be further divided into several regions, for example comprising a hole transport zone, an emission layer, and an electron transport zone; the hole transport zone comprises at least one organic compound as described in the first aspect, further preferably comprising at least one of the organic compounds P1-P400.

[0104] In a preferred embodiment, the organic electroluminescent device comprises a first electrode, a plurality of light-emitting functional layers (organic layers) arranged in sequence, and a second electrode; the organic layers comprise a hole injection layer, a hole transport layer, an electron blocking layer, an emission layer, a hole blocking layer, an electron transport layer, and an electron injection layer arranged in sequence, and the hole injection layer is in contact with the first electrode (anode). The organic layer (preferably the hole transport layer and / or the electron blocking layer) comprises at least one organic compound as described in the first aspect, further preferably comprising at least one of the organic compounds P1-P400.

[0105] In a preferred embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is a glass or a polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, the substrate can also be provided with a thin film transistor (TFT) as a display.

[0106] The first electrode can be formed by sputtering or depositing a 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 an 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.

[0107] The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic layer can be an organic small molecule, an organic macromolecule, or a polymer, and a combination thereof.

[0108] The hole transport zone is located between the anode and the emission layer. The hole transport zone 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 zone can also be a multi-layer structure including at least one 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 emission layer.

[0109] In addition to the organic compounds provided in the present disclosure, the material of the hole transport layer can also include phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant-containing polymers such as polyphenylene vinylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphor sulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0110] 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 employ one or more compounds of HT-1 to HT-51 described above, or employ one or more compounds of HI-1 to HI-3 described below; or employ one or more compounds of HT-1 to HT-51 doped with one or more compounds of HI-1 to HI-3 described below.

[0111] The light-emitting layer includes light-emitting dyes (i.e., dopants) and host materials that can emit different wavelengths of light spectrum. The light-emitting layer can be a single-color light-emitting layer that emits a single color such as red, green, blue, etc. Multiple single-color light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or stacked together to form a color light-emitting layer. When the 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 emit different colors such as red, green, blue, etc. at the same time.

[0112] Depending on the different technologies, the light-emitting layer material can employ different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescent light-emitting materials, etc. In an OLED device, a single light-emitting technology can be employed, or a combination of multiple different light-emitting technologies can be employed. These different light-emitting materials classified by technology can emit the same color of light, or can emit different colors of light.

[0113] In an aspect of the present disclosure, the light-emitting layer employs the fluorescent electroluminescent technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, a combination of one or more of BFH-1 to BFH-17 listed below.

[0114] In an aspect of the present disclosure, the light-emitting layer employs a fluorescent electroluminescent technology. The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, a combination of one or more of BFD-1 to BFD-27 listed below.

[0115] In an aspect of the present disclosure, the light-emitting layer employs a phosphorescent electroluminescent technology. The host material of the light-emitting layer is selected from, but not limited to, a combination of one or more of PH-1 to PH-117.

[0116] In an aspect of the present disclosure, the light-emitting layer employs a phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, a combination of one or more of BPD-1 to BPD-16 listed below.

[0117] In an aspect of the present disclosure, the light-emitting layer employs a phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, a combination of one or more of GPD-1 to GPD-60 listed below. wherein D is deuterium.

[0118] In an aspect of the present disclosure, the light-emitting layer employs a phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.

[0119] In an aspect of the present disclosure, the light-emitting layer employs a phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, a combination of one or more of YPD-1 to YPD-11 listed below.

[0120] In an aspect of the present disclosure, an electron blocking layer (EBL) is located between the hole transport layer and the light-emitting layer. The electron blocking layer can employ, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or employ, but is not limited to, one or more compounds of PH-47 to PH-77 described above; or can employ, but is not limited to, a mixture of one or more compounds of HT-1 to HT-51 and one or more compounds of PH-47 to PH-77.

[0121] The OLED organic material layer can further comprise an electron transport zone between the light-emitting layer and the cathode. The electron transport zone can be a single-layer structure 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 zone can also be a multi-layer structure comprising at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0122] In an aspect of the present disclosure, the electron transport layer material can be selected from, but not limited to, a combination of one or more of the following listed ET-1 to ET-73.

[0123] In an aspect of the present disclosure, a hole blocking layer (HBL) is located between the electron transport layer and the light-emitting layer. The hole blocking layer can employ, but is not limited to, one or more compounds of ET-1 to ET-73 described above, or employ, but is not limited to, one or more compounds of PH-1 to PH-46; or employ, but is not limited to, a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0124] The device can further comprise an electron injection layer between the electron transport layer and the cathode, and the electron injection layer material includes, but is not limited to, a combination of one or more of the following listed: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, Yb.

[0125] The present disclosure also provides a display device comprising the organic electroluminescent device according to the third aspect.

[0126] Preferably, the display device comprises a display screen or a display panel.

[0127] The present disclosure also provides an electronic equipment comprising the aforementioned display device.

[0128] Compared with the prior art, the present disclosure has the following beneficial effects:

[0129] The organic compound provided by the present disclosure has a structure shown in Formula I. Through the design of the molecular structure, the organic compound has excellent photoelectric performance and suitable HOMO / LUMO energy levels, high hole mobility, and good stability, and can exhibit excellent electron blocking performance and hole transport performance. The organic compound is applied to an organic electroluminescent device and is suitable for use as a hole transport layer material and / or an electron blocking layer material, and is particularly suitable for use as an electron blocking layer material, which can effectively improve the luminous efficiency and stability of the device, prolong the service life of the device, and reduce the voltage and energy consumption. DETAILED DESCRIPTION

[0130] The technical solutions of the present disclosure are further illustrated by the detailed description below. It should be understood by those skilled in the art that the examples are only to help understand the present disclosure and should not be regarded as specific limitations of the present disclosure.

[0131] In one embodiment, the organic compound has a structure as shown in Formula I, which can be prepared by the following representative synthesis route:

[0132] wherein, L 1 , L 2 , Ar 1 , Ar 2 , R 1 , R 2 , R 3 , R 4 , R 11 , R 12 , m, n, p, q, r and s have the same definition as Formula I; Hal1, Hal2 represent halogen, each independently selected from any one of F, I, Br or Cl; Reaction I, Reaction II are carried out in the presence of a palladium catalyst. The order of Reaction I and Reaction II can be adjusted according to the synthesis, i.e. Reaction I can be carried out first, then Reaction II, or Reaction II can be carried out first, then Reaction I.

[0133] In one embodiment, Reaction I is carried out first, then Reaction II.

[0134] In one embodiment, Reaction I is carried out in the presence of tris(dibenzylideneacetone)dipalladium(0) Pd2(dba)3, 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride IPr.HCl and a basic substance (such as sodium tert-butoxide NaOBu-t).

[0135] In one embodiment, Reaction II is carried out in the presence of Pd2(dba)3, tri-tert-butylphosphonium tetrafluoroborate (t-Bu)3PBF4 and a basic substance (such as NaOBu-t).

[0136] In one embodiment, the raw material M has r = 1 and s = 1, which can be prepared by the following representative synthesis route:

[0137] wherein, Hal3, Hal4 represent halogen, each independently selected from any one of F, I, Br or Cl; U1, U2 are each independently selected from Reaction III, reaction IV is carried out in the presence of a palladium catalyst. The order of reaction III and reaction IV can be adjusted according to the synthesis, that is, reaction III can be carried out first, and then reaction IV can be carried out, or reaction IV can be carried out first, and then reaction III can be carried out.

[0138] In one specific embodiment, reaction III is carried out first, and then reaction IV is carried out; reaction III and reaction IV are carried out in the presence of tetrakis(triphenylphosphine)palladium Pd(PPh3)4 and a basic substance (for example, potassium carbonate K2CO3).

[0139] In one specific embodiment, r is 1 and s is 0 in the raw material M, which can be prepared by the following representative synthesis path:

[0140] Hal3, U2 have the same meaning as described above; reaction IV is carried out in the presence of Pd(PPh3)4 and a basic substance (for example, K2CO3).

[0141] The specific preparation method of the organic compound of the present disclosure will be described in detail below by taking a plurality of synthesis examples as examples, but the preparation method of the present disclosure is not limited to these synthesis examples.

[0142] It should be noted that obtaining the organic compound is not limited to the synthesis method and raw material used in the present disclosure, and other methods or routes can also be selected by those skilled in the art to obtain the organic compound proposed in the present disclosure. 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 disclosure.

[0143] The compounds, solvents and reagents of the synthesis method not mentioned in the present disclosure are raw material products obtained by commercial means, which can be purchased from the domestic chemical product market, or self-made according to the known method by these raw material products.

[0144] The analysis and detection of intermediates and target products in the following specific embodiments of the present disclosure use 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] + .

[0145] Preparation example 1: synthesis of intermediate M1

[0146] In a 1000 mL single-neck flask, 20.0 g of 2-bromo-7-chloro-9,9'-dimethylfluorene, 9.51 g of phenylboronic acid, 0.75 g of tetrakis(triphenylphosphine)palladium Pd(PPh3)4, 17.97 g of potassium carbonate, 300 mL of 1,4-dioxane and 100 mL of water were added, vacuum-nitrogen was replaced for 3 times, the reaction was heated to 100°C for 5 h. After the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction liquid was separated, the organic phase was filtered through a silica gel column twice, the organic phase was concentrated, methanol was added, reflux stirring was carried out for 1 h, and white powder M1 was obtained by filtration, and then the pure product was recrystallized with ethyl acetate to obtain 17.2 g.

[0147] m / z theoretical value: 304.10; m / z actual value: 305.22.

[0148] Preparation Example 2: Synthesis of intermediate M2

[0149] In a 1000 mL single-neck flask, 20.0 g of 2-bromo-7-chloro-9,9'-dimethylfluorene, 9.51 g of phenylboronic acid, 0.75 g of tetrakis(triphenylphosphine)palladium Pd(PPh3)4, 17.97 g of potassium carbonate, 300 mL of 1,4-dioxane and 100 mL of water were added, vacuum-nitrogen was replaced for 3 times, the reaction was heated to 100°C for 5 h. After the reaction was completed, the reaction was stopped. After cooling to room temperature, the reaction liquid was separated, the organic phase was filtered through a silica gel column twice, the organic phase was concentrated, methanol was added, reflux stirring was carried out for 1 h, and white powder M1 was obtained by filtration, and then the pure product was recrystallized with ethyl acetate to obtain 17.2 g.

[0150] m / z theoretical value: 304.10; m / z actual value: 305.22.

[0151] Synthesis of intermediates M3-M31: The process route is the same as M1, and the only difference is that the raw materials are different. The raw materials, target products and result characterization data are shown in Table 1.

[0152] Table 1

[0153] Synthesis Example 1: Synthesis of organic compound P1

[0154] (1) In a 1000 mL single-neck flask, 10 g of (1,1':2',1"-terphenyl)-3'-amine, 12.43 g of M1, 0.37 g of tris(dibenzyl ketone) palladium (0) Pd2(dba)3, 0.35 g of 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride IPr.HCl, 11.75 g of sodium tert-butoxide NaOBu-t, 300 mL of toluene, vacuum-nitrogen 3 times, the reaction is heated to 90°C for 5h. After the reaction is completed, stop the reaction. Cool to room temperature, separate the liquid, the organic phase is filtered twice through silica gel column, concentrate the organic phase, add methanol to reflux and stir for 1h, filter to obtain white powder P1-1, then recrystallize with ethyl acetate to obtain 16.8 g of pure product.

[0155] m / z theoretical value: 513.25; m / z actual value: 514.37.

[0156] (2) In a 1000 mL single-neck flask, 15 g of P1-1, 6.81 g of 4-bromobiphenyl, 0.27 g of Pd2(dba)3, 0.17 g of tri-tert-butyl phosphonium tetrafluoroborate (t-Bu)3PBF4, 8.42 g of sodium tert-butoxide, 200 mL of toluene, vacuum-nitrogen 3 times, the reaction is heated to 110°C for 5h. After the reaction is completed, stop the reaction. Cool to room temperature, separate the liquid, the organic phase is filtered twice through silica gel column, concentrate the organic phase, add methanol to reflux and stir for 1h, filter to obtain white powder P1, then recrystallize with ethyl acetate three times to obtain 8.3 g of pure product.

[0157] m / z theoretical value: 665.31; m / z actual value: 666.05.

[0158] Synthesis Example 2-35: The process route is the same as that of Synthesis Example 1, except that the raw materials used are different, and the raw materials, target products and result characterization data are shown in Table 2; in Table 2, the raw material M is The raw material 3 represents

[0159] Table 2

[0160] The disclosure exemplarily gives the specific synthesis method of the above several organic compounds, and for other organic compounds without giving the specific synthesis method, they can also be prepared by similar methods, and only by replacing the raw materials, the target product can be obtained, which will not be repeated here, or the skilled in the art can also use other ways in the prior art to prepare.

[0161] Example 1

[0162] An organic electroluminescent device comprising an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, an emission layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode (Al) disposed in sequence. The preparation method of the organic electroluminescent device is as follows:

[0163] (1) The glass plate coated with a transparent conductive layer of ITO is ultrasonically treated in a commercial cleaning agent, then washed in deionized water, ultrasonically degreased in a mixed solvent of acetone / ethanol, baked in a clean environment until the water is completely removed, washed with ultraviolet light and ozone, and the surface is bombarded with a low-energy cation beam;

[0164] (2) The glass substrate with the anode is placed in a vacuum chamber, vacuumed to less than <1x10 -5 Pa, and 10 nm of a mixture of HT-4:HI-3 (97 / 3, w / w) is vacuum evaporated on the anode layer film as a hole injection layer;

[0165] (3) 60 nm of compound HT-4 is vacuum evaporated on the hole injection layer as a hole transport layer;

[0166] (4) 5 nm of the organic compound P1 provided by the disclosure is vacuum evaporated on the hole transport layer as an electron blocking layer;

[0167] (5) 40 nm of a mixture of PH-34:RPD-10 (100 / 3, w / w) is vacuum evaporated on the electron blocking layer as an emission layer;

[0168] (6) 5 nm of compound ET-23 is vacuum evaporated on the emission layer as a hole blocking layer;

[0169] (7) 25 nm of a mixture of ET-69:ET-57 (50 / 50, w / w) is vacuum evaporated on the hole blocking layer as an electron transport layer;

[0170] (8) 1 nm of LiF is vacuum evaporated on the electron transport layer as an electron injection layer;

[0171] (9) 150 nm of aluminum is vacuum evaporated on the electron injection layer as a cathode, obtaining 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.

[0172] Examples 2-18, Comparative Examples 1-4

[0173] An organic electroluminescent device, which is only different from Example 1 in that the material organic compound P1 of the electron blocking layer in step (4) is replaced by the organic compounds in Table 3.

[0174] The structures of the electron blocking layer materials of Comparative Examples 1-4 are as follows:

[0175] The performance of the organic electroluminescent device described above was tested as follows:

[0176] (1) At the same brightness, the driving voltage and current efficiency of the organic electroluminescent device were measured using a digital source meter and a luminance meter; specifically, the voltage was raised at a rate of 0.1 V per second, and the voltage when the current density of the organic electroluminescent device reached 10 mA / cm 2 was measured, i.e., the operating voltage; at the same time, the current density at this time was measured, and the ratio of the brightness to the current density was the current efficiency;

[0177] (2) The LT97 lifetime was tested as follows: the time for the brightness to decay under a constant current density of 60 mA / cm 2 was measured, and LT97 refers to the time for the brightness to decay to 97% of the initial brightness, in hours;

[0178] The data results are shown in Table 3:

[0179] Table 3

[0180] According to the performance data in Table 3, the organic compound provided by the present disclosure is used in an organic electroluminescent device, which is more conducive to reducing the voltage, improving the current efficiency, and prolonging the service life of the device, and is an electron blocking material with excellent performance.

[0181] Comparing the organic compound of the present disclosure with the electron blocking layer materials of Comparative Examples 1-4, it can be seen that P1 and P4 have a longer conjugation than CCP-1 and CCP-4, and P95 has a longer conjugation than CCP-2, which is conducive to the improvement of the hole mobility, thereby reducing the voltage of the device, improving the efficiency, and prolonging the service life. P253 has relatively small steric hindrance compared to CCP-3, which is conducive to the improvement of the hole mobility, the reduction of the voltage, and the improvement of the efficiency.

[0182] Example 19

[0183] An organic electroluminescent device includes, in sequence, 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, a cathode (magnesium-silver electrode), and a light extraction layer. The preparation method of the organic electroluminescent device is as follows:

[0184] (1) The glass plate coated with ITO transparent conductive layer was treated with ultrasonic in commercial cleaning agent, then washed in deionized water, treated with ultrasonic in acetone / ethanol mixed solvent to remove oil, baked in clean environment until water was completely removed, washed with ultraviolet light and ozone, and the surface was bombarded with low-energy cation beam;

[0185] (2) The glass substrate with anode above was placed in a vacuum chamber, vacuumed to less than <1x10 -5 Pa, 10 nm of HT-4:HI-3 (97 / 3, w / w) mixture was vacuumed and deposited on the anode layer film as a hole injection layer;

[0186] (3) 120 nm of compound HT-4 was vacuumed and deposited on the hole injection layer as a hole transport layer;

[0187] (4) 5 nm of the organic compound P121 provided by the present disclosure was vacuumed and deposited on the hole transport layer as an electron blocking layer;

[0188] (5) 40 nm of PH-34:RPD-10 (100 / 3, w / w) mixture was vacuumed and deposited on the electron blocking layer as a light-emitting layer;

[0189] (6) 5 nm of compound ET-23 was vacuumed and deposited on the light-emitting layer as a hole blocking layer;

[0190] (7) 25 nm of ET-69:ET-57 (50 / 50, w / w) mixture was vacuumed and deposited on the hole blocking layer as an electron transport layer;

[0191] (8) 1 nm of Yb was vacuumed and deposited on the electron transport layer as an electron injection layer;

[0192] (9) 13 nm of Ag:Mg (11%) thin film was vacuumed and deposited on the electron injection layer as a cathode, the evaporation rate ratio of Ag to Mg was 1:0.11, and the evaporation rate of Ag was 0.1 nm / s;

[0193] (10) 60 nm of compound HT21 was vacuumed and deposited on the cathode as a light extraction layer; the evaporation rate of all organic layers and Yb was controlled at 0.1 nm / s, and the organic electroluminescent device was obtained.

[0194] Examples 20-35, Comparative Examples 5-10

[0195] An organic electroluminescent device, which is only different from Example 19 in that the material of the electron blocking layer in step (4) is replaced by the organic compound in Table 4.

[0196] The structure of the electron blocking layer material of Comparative Examples 5-10 is as follows:

[0197] The performance of the organic electroluminescent device described above was tested in the following manner:

[0198] (1) At the same brightness, the driving voltage and current efficiency of the organic electroluminescent device were measured using a digital source table and a luminance meter; specifically, the voltage was raised at a rate of 0.1 V per second, and the voltage at which the current density of the organic electroluminescent device reached 10 mA / cm 2 was measured, i.e., the operating voltage; at the same time, the current density at this time was measured, and the ratio of the brightness to the current density was the current efficiency;

[0199] (2) The LT98 lifetime was tested in the following manner: the time for the brightness to decay under a constant current density of 30 mA / cm 2 was measured, and LT98 refers to the time for the brightness to decay to 98% of the initial brightness, in hours;

[0200] The test data are shown in Table 4:

[0201] Table 4

[0202] As can be seen from the performance data in Table 4, the organic compound provided by the present disclosure is used in an organic electroluminescent device, is more conducive to reducing the voltage, improving the current efficiency, and prolonging the service life of the device, and is a red light electron blocking material with excellent performance.

[0203] As can be seen from a comparison of the electron blocking layer material of the organic compound of the present disclosure and Comparative Examples 5-9, P121 and P124 have a longer conjugation in the molecular structure than CCP-5, which is conducive to improving the hole mobility, thereby reducing the voltage and improving the efficiency of the device; P273 has better resistance to electrons and triplet excitons at the end than CCP-6, which is conducive to blocking electrons and triplet excitons and improving the performance of the device; P127 has a structure containing 9,9-dimethylfluorene, which is more conducive to the transmission of holes on the one hand, and the alkyl group on the fluorene structure can better block electrons and triplet excitons on the other hand, so that the device has higher efficiency, longer service life, and lower voltage. P193 has a longer conjugation than CCP-8, and P217 has a longer conjugation than CCP-10, which improves the hole mobility and enables the device to have excellent comprehensive performance.

[0204] Applicants declare that the organic compounds and applications thereof of the present disclosure are illustrated by the above-mentioned examples, but the present disclosure is not limited to the above-mentioned examples, i.e. it does not mean that the present disclosure must rely on the above-mentioned examples to be implemented. It should be understood by those skilled in the art that any improvement of the present disclosure, equivalent replacement of each raw material of the product of the present disclosure, addition of auxiliary ingredients, selection of specific modes, etc. fall within the protection scope and disclosure scope of the present disclosure.

Claims

1. An organic compound characterized in that, The organic compound has a structure as shown in Formula I: wherein L 1 , L 2 each independently is selected from any one of substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene, and the L 2 is not Ar 1 any one selected from the group consisting of C6-C18 monocyclic aryl residues of valence m+1, C10-C14 condensed aryl residues of valence m+1 ; Ar 2 any one selected from the group consisting of a substituted or unsubstituted n+1-valent C6-C30 aryl residue, a substituted or unsubstituted n+1-valent C3-C30 heteroaryl residue; R 1 is selected from any one of methyl, isopropyl, C6-C18monocyclic aryl, C10-C14fused aryl, C1-C20alkoxy, C3-C20cycloalkyl, C2-C20heterocycloalkyl, or cyano; X is selected from a single bond, O, S, or CR 13 R 14 any one of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R 2 , R 13 , R 14 each independently is selected from any one of substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; R 3 , R 4 , R 11 , R 12 each independently is selected from any one of substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl; each of m, n is independently selected from 0 to the maximum number of substituents; each of p, q is independently selected from an integer from 0 to 5; r is 0 or 1, s is 0 or 1, and r + s ≥ 1; L 1 、L 2 、R 2 、R 3 、R 4 、R 11 、R 12 、R 13 、R 14 each of the substituents mentioned in the substituents is independently selected from at least one of C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 alkoxy, cyano, C2-C20 alkenyl, C6-C60 aryl, C3-C60 heteroaryl.

2. The organic compound according to claim 1, characterized by The organic compound has a structure as shown in any one of Formula II-1, Formula II-2, Formula II-3: wherein L 1 , L 2 , Ar 1 , Ar 2 , R 1 , R 2 , R 3 , R 4 , R 11 , R 12 , m, n, p, q have the same defined ranges as in formula I. 3.The organic compound according to claim 1 or 2, characterized by The L 2 is selected from any one of the following groups of substituted or unsubstituted: wherein, --* represents the linking position of the group; Y1is selected from O, S, NR 21 or CR 22 R 23 any one of; R 21 , R 22 , R 23 each independently is selected from any one of C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C6-C30 aryl or C3-C30 heteroaryl; said R 22 and R 23 are not connected or are connected by a chemical bond into a ring; L 2 each of the substituents mentioned in the substituents is independently selected from at least one of C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 alkoxy, cyano, preferably at least one of C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, further preferably at least one of methyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclohexyl.

4. The organic compound according to claim 3, characterized by The L 2 is selected from any one of the following groups, which are substituted or unsubstituted: wherein — * represents the point of attachment of the group.

5. The organic compound according to claim 1 or 2, characterized by The L 1 is selected from any one of the following groups, which are substituted or unsubstituted: wherein, --* represents the linking position of the group; Y2is selected from O, S, NR 31 or CR 32 R 33 any of the above; R 31 , R 32 , R 33 are each independently selected from any one of C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C6-C30 aryl or C3-C30 heteroaryl; said R 32 and R 33 are not connected or are connected by a chemical bond into a ring; R 34 any one selected from the group consisting of hydrogen, C1-C20 straight chain or branched alkyl, C3-C20 cycloalkyl, C6-C30 aryl, or C3-C30 heteroaryl; Preferably, L 1 each of the substituents mentioned in the group of substituents is independently selected from at least one of C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 alkoxy.

6. The organic compound according to claim 5, characterized by The L 1 is selected from any one of the following groups of substituted or unsubstituted: wherein, --* represents the linking position of the group.

7. The organic compound according to claim 1 or 2, wherein said Ar 1 is selected from any one of the following groups: wherein — * represents the connection site of Ar 1 with L 1 .

8. The organic compound according to claim 1 or 2, wherein said R 1 is selected from any one of methyl, isopropyl, phenyl, naphthyl, biphenyl, C1-C10alkoxy, cyano, C3-C10cycloalkyl, or C2-C10heterocycloalkyl; Preferably, the m is selected from an integer from 0 to 2.

9. The organic compound according to claim 1 or 2, wherein said Ar 2 is selected from any one of the following groups: wherein, --* represents the linking position of the group; Y3, Y4are each independently selected from O, S, NR 41 or CR 42 R 43 any of the above; R 41 , R 42 , R 43 are each independently selected from any one of C1-C20 linear or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C6-C30 aryl or C3-C30 heteroaryl; said R 42 and R 43 are not connected or are connected by a chemical bond into a ring; R 44 is selected from any one of hydrogen, C1-C20 straight chain or branched chain alkyl, C3-C20 cycloalkyl, C6-C30 aryl or C3-C30 heteroaryl. 10.The organic compound according to claim 9, characterized by Ar 2 is selected from any one of the following groups: wherein -* represents the point of attachment of the group.

11. The organic compound according to claim 1 or 2, wherein said R 2 any one selected from the group consisting of C1-C10 linear or branched alkyl, C6-C20 aryl, preferably methyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, phenyl, naphthyl or biphenyl; Preferably, the n is selected from an integer from 0 to 2. Preferably, said R 11 , R 12 each independently is selected from any one of C1-C10 linear or branched alkyl, preferably methyl; Preferably, said X is selected from any one of a single bond, O, S or CR 13 R 14 13 , R 14 each independently is selected from any one of C1-C10 linear or branched alkyl, C6-C20 aryl, preferably methyl or phenyl;​ Preferably, the X is a single bond or O. Preferably, said R 3 , R 4 each independently is selected from any one of C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, preferably methyl, isopropyl, tert-butyl, isobutyl, tert-pentyl or cyclohexyl; Preferably, each of p, q is independently 0 or 1. 12.The organic compound according to claim 1, characterized by The organic compound has a structure as shown in any one of P1-P400:

13. Use of an organic compound as claimed in any one of claims 1 to 12, characterized in that The organic compound is applied to an organic electroluminescence device. Preferably, the organic compound is used as an electron blocking layer material and / or a hole transport layer material in an organic electroluminescence device.

14. An organic electroluminescent device, characterized by The organic electroluminescence 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 as claimed in any one of claims 1-12; 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 1-12; Or, the organic layer comprises an electron blocking layer, and the electron blocking layer comprises at least one organic compound as claimed in any one of claims 1-12.

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