Nitrogen-containing compound, composition and organic electroluminescent device

Abstract

The invention provides a nitrogen-containing compound, a composition and an organic electroluminescent device. The nitrogen-containing compound has a structure as shown in a formula I. The structure of the nitrogen-containing compound is designed, so that the nitrogen-containing compound is suitable for being used as a main body material of a light-emitting layer of the organic light-emitting device, and the organic light-emitting device has relatively high current efficiency and relatively long service life.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a nitrogen-containing compound, a composition and an organic electroluminescent device. Background Art

[0002] The structure of an organic electroluminescent device is specifically: an anode, a cathode, and an organic layer between the two. In order to improve the efficiency and stability of the organic electroluminescent element, the organic material layer includes multiple layers with different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer, a light-emitting layer, an electron transport layer (ETL), and an electron injection layer (EIL). Currently, organic electroluminescence has become a mainstream display technology, and accordingly, various new OLED materials have also been developed. Electron transport materials and hole injection materials, hole transport materials or hole blocking layers are major obstacles to the full practical application of OLED technology, which directly limit the luminous efficiency, service life, and operating voltage of the device.

[0003] In order to meet people's higher requirements for OLED devices, the field urgently needs to develop more types of materials to improve the performance of OLED devices in terms of current efficiency, lifespan, etc. Summary of the Invention

[0004] In response to the shortcomings of the prior art, the present invention provides a nitrogen-containing compound, composition, and organic electroluminescent device. The present invention designs the structure of the nitrogen-containing compound to make it suitable as a host material for the phosphorescent light-emitting layer of an organic electroluminescent device, thereby enabling the organic electroluminescent device to have higher current efficiency and longer life.

[0005] To achieve this object, the present invention adopts the following technical solutions:

[0006] In a first aspect, the present invention provides a nitrogen-containing compound having a structure shown in the following formula I:

[0007]

[0008] wherein Ar1, Ar2, and Ar3 are each independently selected from a C6-C40 aryl group or a C6-C30 heteroaryl group;

[0009] X is selected from C or Si;

[0010] A1, A2, A3 are each independently selected from N or CR, and at least one is selected from N; R is selected from any one of H, C6-C20 aryl or C1-C12 alkyl;

[0011] R1 is selected from C6-C40 aryl or C6-C30 heteroaryl;

[0012] R2 is selected from any one of H, C6-C40 aryl or C6-C30 heteroaryl;

[0013] n is selected from 0, 1, 2 or 3;

[0014] Ar 11 、Ar 12 Each is independently selected from the following groups represented by the structures A-1 to A-7, wherein "*" represents the connection position:

[0015]

[0016] Ar4, Ar5, Ar 6、 Ar7 are each independently selected from C6-C40 aryl or C6-C30 heteroaryl;

[0017] Y is selected from C or Si;

[0018] The hydrogen atoms in the compound of formula I may each independently be substituted by at least one of a deuterium atom (D), -F, -CN, a C6-C20 aryl group, a C1-C12 alkyl group, or a C1-C12 alkoxy group.

[0019] The compounds of formula I do not include the following compounds:

[0020]

[0021] In the present invention, the structure of the nitrogen-containing compound is designed to make it suitable as the main material of the phosphorescent light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has higher current efficiency and longer life.

[0022] In the present invention, C6-C40 can be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.

[0023] C6-C30 can be C6, C8, C10, C12, C16, C20, C24, C28 or C30, etc.

[0024] C6-C20 can be C6, C8, C10, C12, C16 or C20, etc.

[0025] C1~C12 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12.

[0026] It should be noted that, in the present invention, "D" represents a deuterium atom, and the same shall apply hereinafter.

[0027] 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.

[0028] As a preferred technical solution of the present invention, the compound of formula I has any one of the structures shown in I-1 to I-4:

[0029]

[0030] Among them, Ar1, Ar2, Ar3, A1, A2, A3, R1, R2, n, Ar 11 、Ar 12 Has the same definition as above.

[0031] As a preferred technical solution of the present invention, the C6-C40 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, triphenylene, and fluoranthenyl.

[0032] As a preferred technical solution of the present invention, the C6-C30 heteroaryl group is selected from any one of a carbazolyl group, a dibenzothiophenyl group, and a dibenzofuranyl group.

[0033] As a preferred technical solution of the present invention, the C6-C20 aryl group is selected from any one of phenyl, biphenyl, terphenyl and naphthyl.

[0034] As a preferred technical solution of the present invention, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, tert-butyl and cyclohexyl.

[0035] As a preferred technical solution of the present invention, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy, and hexyloxy.

[0036] As a preferred technical solution of the present invention, the Ar1, Ar2, Ar3, Ar4, Ar5, Ar 6、 Ar7 are each independently selected from phenyl, carbazolyl, biphenyl, naphthyl, triphenylene, dibenzothiophenyl, dibenzofuran, The dotted line indicates the connection site.

[0037] Preferably, Ar1, Ar2, and Ar3 are each independently selected from any one of phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl.

[0038] Preferably, Ar4, Ar5, Ar 6、 Ar7 are each independently selected from phenyl, naphthyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, The dotted line indicates the connection site.

[0039] Preferably, R is selected from H or phenyl.

[0040] Preferably, R1 is selected from any one of phenyl, biphenyl, naphthyl, triphenylene, dibenzofuranyl, and carbazolyl.

[0041] Preferably, R2 is selected from H or phenyl.

[0042] As a preferred technical solution of the present invention, the hydrogen atoms in the compound of formula I can each independently be substituted by at least one of -D, -F, -CN, phenyl, naphthyl, biphenyl, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy or butoxy.

[0043] Preferably, the hydrogen atoms in the compound of formula I can each independently be substituted by at least one of -D, -F, -CN, phenyl, naphthyl, methyl, ethyl, tert-butyl, methoxy, and propoxy.

[0044] Preferably, n is selected from 1.

[0045] As a preferred technical solution of the present invention, the compound of formula I has the structure shown in the following formula I-5:

[0046]

[0047] Among them, Ar1, Ar2, Ar3, A1, A2, A3, R1, R2, Ar 11 、Ar 12 Has the same definition as above.

[0048] As a preferred technical solution of the present invention, the nitrogen-containing compound is selected from any one of the following substituted or unsubstituted compounds:

[0049]

[0050]

[0051]

[0052]

[0053] The substitution means that the hydrogen atoms in the above nitrogen-containing compound can be independently replaced by deuterium atoms. Preferably, the compound of formula I is selected from any one of the following compounds:

[0054]

[0055]

[0056] In the present invention, the compound of formula I can be prepared using the following general formula:

[0057]

[0058] Among them, Ar1, Ar2, Ar3, X, R1, R2, A1, A2, A 3、 Ar 11 、Ar 12 , n has the same definition as above;

[0059] X1 to X4 are each independently selected from any one of F, Cl, Br or I. Those skilled in the art can appropriately select a specific type based on common knowledge to obtain the compound of the present invention, which illustratively includes the following steps:

[0060] (1) The intermediate represented by M0-2 is first reacted with butyl lithium, and then reacted with the intermediate represented by M0-1 to prepare the intermediate represented by M0;

[0061] (2) The intermediate shown in M0 is prepared to obtain the boronic acid intermediate shown in M1;

[0062] (3) Boronic acid intermediates represented by M1 and Reaction to prepare the compound shown in formula I.

[0063] Of course, those skilled in the art can, based on the above synthesis method, combine it with common knowledge in the art and adopt other synthesis methods to prepare the compound of formula I, which is also within the scope of protection of the present invention. For example, the butyl lithium in step (1) can be specifically selected as n-butyl lithium, sec-butyl lithium, tert-butyl lithium, or changed to lithium diisopropylamide.

[0064] The compound I provided by the present invention can also be prepared by the following method:

[0065]

[0066] (S1) The intermediate shown in M0 is prepared to obtain the boronate intermediate shown in M1BA;

[0067] (S2)M1BA shown in the boronate intermediate and Reaction to prepare the compound shown in formula I.

[0068] Among them, Ar1, Ar2, Ar3, X, R1, R2, A1, A2, A 3、 Ar 11 、Ar 12 , n has the same definition as above;

[0069] X1 to X4 are each independently selected from any one of F, Cl, Br or I. Those skilled in the art can appropriately select a specific type based on common knowledge to obtain the compound of the present invention.

[0070] Of course, those skilled in the art can, based on the above synthesis method, combine it with common knowledge in the art and adopt other synthesis methods to prepare the compound of formula I, which is also within the scope of protection of the present invention. For example, the boric acid pinacol ester compound prepared in step (S1) can be replaced with other borate ester compounds as long as they can be used with The compound shown in formula I is prepared by carrying out the reaction, which is also within the scope of protection of the present invention.

[0071] In a second aspect, the present invention provides an intermediate comprising compound M0, compound M1, and compound M1BA:

[0072]

[0073] Among them, Ar1, Ar2, Ar3, X, R1, R2, A1, A2, A 3、 Ar 11 、Ar 12 , n has the same definition as above;

[0074] X3 is selected from any one of F, Cl, Br or I;

[0075] The intermediate is used to prepare the nitrogen-containing compound as described in the first aspect.

[0076] Preferably, the intermediate includes the following compounds:

[0077]

[0078] In a third aspect, the present invention provides a composition comprising a first component and a second component;

[0079] The first component includes the compound of formula I as described in the first aspect;

[0080] The second component includes a compound having a structure shown in the following formula II:

[0081]

[0082] Among them, Ar 31 、Ar 32each independently selected from a single bond, a C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) arylene group, or a C6-C30 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, or C30, etc.) heteroarylene group;

[0083] Ar 33 Any one selected from H, C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl, or C6-C30 (for example, C6, C8, C10, C12, C16, C20, C24, C28, or C30, etc.) heteroaryl;

[0084] p1 and p2 are each independently selected from 0, 1, 2, 3 or 4;

[0085] The hydrogen atoms in the compound of formula II may be substituted by at least one of a deuterium atom, -F, -CN, a C6-C20 (for example, C6, C8, C10, C12, C16 or C20, etc.) aryl group, a C1-C12 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12) alkyl group, a C1-C12 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12) alkoxy group, a trimethylsilyl group, a triphenylsilyl group, and a tetraphenylmethyl group.

[0086] As a preferred technical solution of the present invention, the compound of formula II is selected from any one of the following substituted or unsubstituted compounds:

[0087]

[0088]

[0089] The substitution means that the hydrogen atoms in the above compounds can each be independently replaced by a deuterium atom.

[0090] It should be noted that there is no special limitation on the preparation method of the above-mentioned compounds in the present invention, and all commonly used preparation methods in the art are applicable.

[0091] In a fourth aspect, the present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;

[0092] The organic thin film layer material includes the nitrogen-containing compound described in the first aspect and / or the composition described in the third aspect.

[0093] As a preferred technical solution of the present invention, the organic thin film layer includes a light-emitting layer, and the main material of the light-emitting layer includes the nitrogen-containing compound as described in the first aspect.

[0094] Preferably, the light-emitting layer is a phosphorescent light-emitting layer.

[0095] As a preferred technical solution of the present invention, the organic electroluminescent device is a blue organic electroluminescent device.

[0096] The luminescent layer of the present invention includes a luminescent layer host material and a dopant material, wherein the dopant material is also called a dye or a phosphorescent luminescent material. The luminescent layer host material can be a single compound or a mixture of two or more compounds.

[0097] The light-emitting layer includes a phosphorescent light-emitting layer, and the phosphorescent light-emitting layer includes a green phosphorescent light-emitting layer, a red phosphorescent light-emitting layer, a yellow phosphorescent light-emitting layer, and a blue phosphorescent light-emitting layer.

[0098] The volume percentage of the main material in the phosphorescent light-emitting layer is 60% to 99.9% (for example, it can be 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98% or 99.9%, etc.), preferably 70% to 99.5%, and more preferably 85% to 95%.

[0099] In the present invention, the doping material for the light-emitting layer may be a phosphorescent material, which is also called a triplet light-emitting material and refers to a substance that emits light from a triplet excited state. The specific choice of phosphorescent material in the present invention is not particularly limited, and any doping material for the light-emitting layer commonly used in the art is applicable, including but not limited to a compound having the structure shown in the following formula PD:

[0100]

[0101] wherein M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu, or Au;

[0102] Y1-Y4 are each independently selected from carbon or nitrogen;

[0103] Y1 and Y2 can be connected by a single bond or a double bond, and Y3 and Y4 can be connected by a single bond or a double bond;

[0104] Cy1 and Cy2 are each independently selected from any one of phenyl, naphthyl, fluorenyl, spirofluorenyl, indenyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiophenyl, benzimidazolyl, benzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzothiophenyl, and N-heterocarbazolyl, wherein Cy1 and Cy2 may be optionally linked to each other via a single bond or an organic linking group;

[0105] Any two ligands of M, or more than two ligands, may be connected by a single bond or a double bond, or may be bridged by O or S, or may be connected by any chemical group or chemical structure to form a structural form that conforms to chemical principles;

[0106] R 91 and R 92Each is independently selected from -H, -D, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid, carboxylate, sulfonic acid, sulfonate, phosphoric acid, phosphate, -SF5, substituted or unsubstituted C1-C60 (for example, C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkyl, substituted or unsubstituted C2-C6 C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkenyl, substituted or unsubstituted C2-C60 (for example, C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkynyl, substituted or unsubstituted C1-C60 (for example, C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) C2-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9 or C10) heterocycloalkyl, substituted or unsubstituted C6-C60 (for example, C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) aryl, substituted or unsubstituted C6-C60 (for example, C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) aryl, substituted or unsubstituted C6-C60 ( For example, it can be any one of C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) aryloxy, substituted or unsubstituted C6-C60 (for example, it can be C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) arylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0107] a1 and a2 are each independently an integer selected from 1 to 5, for example, 1, 2, 3, 4 or 5;

[0108] b is an integer selected from 0-4, for example, 0, 1, 2, 3 or 4;

[0109] a is selected from 1, 2 or 3;

[0110] L1 is a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand.

[0111] Preferably, the compound of formula PD is selected from any one of the following compounds:

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118] In the present invention, the organic thin film layer includes a hole layer, and the hole layer includes a hole injection layer, a hole transport layer and an electron blocking layer.

[0119] The hole injection layer material includes a P-type dopant. The P-type dopant coexists with the hole injection layer material in the OLED device and is capable of oxidizing the hole injection layer material, thereby acting as an electron acceptor and promoting the migration of holes from the hole injection layer toward the anode. In the present invention, the difference between the absolute value of the LUMO of the P-type dopant and the absolute value of the HOMO of the hole layer material is greater than -0.2V, preferably greater than -0.1eV, more preferably greater than 0eV, more preferably greater than 0.1eV, and even more preferably greater than 0.2eV.

[0120] The P-type dopant is present in the hole injection layer at a volume percentage of 1% to 10% (e.g., 1%, 2%, 4%, 6%, 8%, or 10%). In the present invention, there is no particular limitation on the type of the P-type dopant. For example, compounds D-1 to D-13 disclosed in CN113728453A or compounds HI-1 to HI-9 described below may be used:

[0121]

[0122]

[0123] In the present invention, the hole layer material (including the hole injection layer, the hole transport layer and the electron blocking layer) has a structure shown in the following formula HT-GH4:

[0124]

[0125] Among them, L 41 is selected from a single bond, a C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl group, a C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl group;

[0126] Ar 41 、Ar42 each independently selected from C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl, C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl;

[0127] X is selected from CR 41 R 42 or NR 43 , where R 41 、R 42 、R 43 Each independently selected from substituted or unsubstituted phenyl (the substituted substituent is selected from C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkyl, C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkoxy), naphthyl, triphenylene, fluoranthenyl, 9,9-dimethylfluorenyl, biphenyl, substituted or unsubstituted group (the substituted substituent is phenyl), substituted or unsubstituted dibenzothienyl (the substituted substituent is phenyl), substituted thienyl, C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkyl, R 41 、R 42 They can be linked to form rings via single bonds.

[0128] The compound of formula HT-GH4 is selected from any one of the following compounds:

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135] In the present invention, the hole layer material (including the hole injection layer, the hole transport layer and the electron blocking layer) further includes a compound having a structure as shown in the following formula IA or a compound having a structure as shown in the following formula IB:

[0136]

[0137] wherein L is selected from any one of a C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40) arylene group, a dibenzofuranyl group, or a dibenzothiophenyl group;

[0138] m is selected from an integer between 0 and 4 (for example, 0, 1, 2, 3 or 4), and n is selected from 0 or 1;

[0139] Ar is selected from any one of triphenylene, fluoranthenylene, dibenzofuranylene or dibenzothiophenylene;

[0140] Ar1 and Ar2 are each independently selected from any one of a C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40) aryl group, a dibenzofuran group, or a dibenzothiophenyl group;

[0141] Ar1 and Ar, Ar2 and Ar, and Ar1 and Ar2 can each independently be connected or bridged by a single bond, O, S, CR1R2, or NR.

[0142] R, R1, and R2 are each independently selected from any one of a C1-C20 (e.g., C1, C2, C4, C6, C8, C10, C12, C14, C16, C18, or C20) alkyl group, a C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40) aryl group, a dibenzofuranyl group, or a dibenzothiophenyl group;

[0143] H in the compound of formula IB and the compound of formula IA may each independently be replaced by at least one of -F, -CN, -D (deuterium atom), C1-C6 alkyl, C1-C6 alkoxy, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, triphenylene, fluoranthenyl, pyrenyl, perylenyl, spirofluorenyl, indenofluorenyl or hydrogenated benzanthryl.

[0144] Preferably, Ar is a fluoranthenyl group, and m+n>1.

[0145] Preferably, H in the compound of formula IB and the compound of formula IA can be replaced by at least one of -F, -CN, -D, C1-C3 alkyl (for example, methyl, ethyl or propyl), C1-C3 alkoxy (for example, methoxy, ethoxy or propoxy), phenyl, biphenyl, triphenylene, and fluoranthene.

[0146] Preferably, L, Ar1, and Ar2 are each independently selected from at least one of phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, triphenylene, fluoranthenyl, pyrenyl, perylene, spirofluorenyl, indenofluorenyl, and hydrogenated benzanthryl.

[0147] Preferably, the compound of formula IB is selected from the following structures:

[0148]

[0149]

[0150] Wherein, L is phenylene;

[0151] Ar1, Ar2, and m have the same protection scope as above.

[0152] Preferably, the compound of formula IB is selected from any one of the following compounds 1-112:

[0153]

[0154]

[0155]

[0156]

[0157] In the OLED device provided by the present invention, the hole layer material, in addition to the compound of formula HT-GH4, the compound of formula IB, and the compound of formula IA, may also include conventional hole materials in the art, without particular limitation. Exemplary examples include, but are not limited to, triarylamine compounds or carbazole compounds. Triarylamine compounds or carbazole compounds containing more than 3 N atoms are preferred, because the HOMO of triarylamine compounds or carbazole compounds containing more than 3 N atoms is higher (the absolute value is smaller), and they are more suitable for use as hole injection layer materials. Triarylamine compounds or carbazole compounds containing 2 or 1 N atoms can be used as hole transport layer materials. Some compounds or carbazole compounds containing 1 N atom, if they have a higher LUMO, can also be used as electron blocking layer materials.

[0158] The triarylamine compound or the carbazole compound is used as the hole layer material, and the hole layer material includes the following structure:

[0159]

[0160]

[0161] Among them, Ar 601 ~Ar609 Each independently selected from any one of a substituted or unsubstituted C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted naphthobenzothiophenyl group, a substituted or unsubstituted dinaphthofuranyl group, and a substituted or unsubstituted dinaphthothiophenyl group;

[0162] And Ar 601 ~Ar 609 Ar atoms adjacent to or connected to the same N atom 601 ~Ar 609 , can be connected by single key or through O, S, CR 701 R 702 NR 703 bridging;

[0163] R 701 、R 702 、R 703 is selected from C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40) aromatic groups, C6-C20 (e.g., C6, C8, C10, C12, C16, or C20) heteroaryl groups, C1-C6 (e.g., C1, C2, C3, C4, C5, or C6) alkyl groups, and R 701 、R 702 Can connect via one-touch.

[0164] A hole-blocking layer (HBL) can confine holes and / or excitons within the emitting layer (EL) to improve device current efficiency and lifetime. Compared to the EL material closest to the HBL interface, the HBL material has a lower HOMO (larger absolute value) and / or higher triplet energy.

[0165] The electron transport layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped, and doping may be used to enhance conductivity. In the present invention, there is no particular limitation on the ETL material, and any metal complex or organic compound may be used as long as it can transport electrons. Generally, the electron transport layer material contains at least one of the following structural fragments: pyridine structure, pyrimidine structure, triazine structure, benzimidazole structure, benzoxazole structure, benzothiazole structure, N-naphthalene structure, N-heterophthalene structure, N-heterocarbazole structure, and N-heterodibenzothiophene structure.

[0166] In the present invention, there is no particular limitation on the electron transport layer materials, which exemplarily include but are not limited to:

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] In the present invention, the cathode material is a metal with a low work function (e.g., alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.)), a metal alloy composed of multiple metals (e.g., an alloy composed of an alkali metal or alkaline earth metal and silver, e.g., an alloy composed of magnesium and silver), or a multilayer structure. If the cathode material is a multilayer structure, in addition to the metals mentioned above, other metals with relatively high work functions, such as Ag or Al, may also be used. In this case, combinations of these metals are typically used, such as Ca / Ag, Mg / Ag, or Ba / Ag.

[0177] Alternatively, a thin intermediate layer of a material with a high dielectric constant may be introduced between the metal cathode and the organic semiconductor to form a multilayer structure. The material with a high dielectric constant may also be referred to as an electron injection material, and may be fluorides of alkali metals or alkaline earth metals, and corresponding oxides or carbonates (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.) or lithium quinoline (LiQ).

[0178] Compared with the prior art, the present invention has the following beneficial effects:

[0179] In the present invention, the structure of the nitrogen-containing compound is designed to make it suitable as the main material of the phosphorescent light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has higher current efficiency and longer life. DETAILED DESCRIPTION

[0180] For the convenience of understanding the present invention, the present invention is given below with examples. It should be understood by those skilled in the art that the examples are only for the purpose of helping to understand the present invention and should not be regarded as specific limitations of the present invention.

[0181] Preparation Example 1

[0182] This preparation example provides the intermediate P1-1BA, the synthesis method of which is as follows:

[0183]

[0184] (1) Synthesis of intermediate P1-0

[0185] In a nitrogen atmosphere, 2.7 g of 5-bromo-2-chloro-1,1'-biphenyl and 70 mL of tetrahydrofuran were added to a 250 mL three-necked flask, then cooled to -78°C, and 0.01 mol of butyl lithium in n-hexane solution (concentration 1.6 M, 6.3 mL) was slowly added. The temperature was then maintained at -78°C to -60°C for 30 min. A solution prepared by 3.0 g of triphenylsilyl chloride and 20 mL of tetrahydrofuran, 0.0001 mol of Pd(dba)2, and 0.0001 mol of anhydrous nickel chloride were added. The temperature was slowly raised to room temperature for 2 hours, then raised to reflux for 2 hours, cooled, and separated by adding water and toluene. The organic layer was washed with water until neutral, dried over anhydrous magnesium sulfate, filtered to remove the desiccant, and concentrated to dryness. The reaction was separated by silica gel column chromatography and eluted with petroleum ether to obtain intermediate P1-0 (3.1 g).

[0186] The obtained intermediate P1-0 was detected by mass spectrometry, and the m / z was 446.13.

[0187] (2) Synthesis of intermediate P1-1BA

[0188] In a nitrogen atmosphere, 4.5 g of intermediate P1-0, 3.8 g of pinacol diboronate, 200 mL of isopropanol, 2.2 g of triethylamine, 0.1 g of bis(1,5-cyclooctadiene)nickel(0), and 0.18 g of triphenylphosphine were added to a 500 mL three-necked flask. The temperature was raised to 35°C for reaction for 20 hours, and then raised to 50°C for reaction for 4 hours. Water and ethyl acetate were added for separation. The organic layer was washed with water until neutral, dried over anhydrous magnesium sulfate, filtered to remove the desiccant, concentrated to dryness, and separated by silica gel column chromatography with petroleum ether:ethyl acetate = 10:1 (volume ratio) to obtain intermediate P1-1BA (3.8 g).

[0189] The obtained intermediate P1-1BA was detected by mass spectrometry, with m / z of 538.25.

[0190] Preparation Example 2

[0191] This preparation example provides the intermediate P7-1BA, the synthesis method of which is as follows:

[0192]

[0193] (1) Synthesis of intermediate P7-0

[0194] Referring to the synthesis method of intermediate P1-0 provided in Preparation Example 1, 5-bromo-2-chloro-1,1'-biphenyl was replaced with an equal amount of The intermediate P7-0 was obtained.

[0195] The obtained intermediate P7-0 was detected by mass spectrometry, and the m / z was 522.16.

[0196] (2) Synthesis of intermediate P7-1BA

[0197] Referring to the synthesis method of intermediate P1-1BA provided in Preparation Example 1, intermediate P1-0 was replaced with an equal amount of intermediate P7-0 to obtain intermediate P7-1BA.

[0198] The obtained intermediate P7-1BA was detected by mass spectrometry, and the m / z was 614.28.

[0199] Preparation Example 3

[0200] This preparation example provides the intermediate P9-1, the synthesis method of which is as follows:

[0201]

[0202] (1) Synthesis of intermediate P9-0

[0203] Referring to the synthesis method of intermediate P1-0 provided in Example 1, 5-bromo-2-chloro-1,1'-biphenyl was replaced by an equal amount of The intermediate P9-0 was obtained.

[0204] The obtained intermediate P9-0 was subjected to mass spectrometry detection, and the two peaks with the largest m / z were 490.08 and 492.07.

[0205] (2) Synthesis of intermediate P9-1

[0206] In a nitrogen atmosphere, 0.01 mol of intermediate P9-0 and 70 mL of tetrahydrofuran were added to a 250 mL three-necked flask, and then the temperature was lowered to -78 ° C. 0.01 mol of butyl lithium in n-hexane solution (concentration 1.6 M, 6.3 mL) was slowly added, and then the temperature was maintained at -78 ° C to -60 ° C for 30 min. A solution containing 0.12 mol of trimethyl borate and 10 mL of tetrahydrofuran was added, and the temperature was slowly raised to room temperature for 2 hours, and then raised to reflux for 2 hours. The temperature was lowered, and aqueous ammonium chloride and ethyl acetate were added for separation. The organic layer was washed with water until neutral, dried over anhydrous magnesium sulfate, and after filtering out the desiccant, it was concentrated to dryness, petroleum ether was added and stirred to obtain a solid, which was filtered to obtain intermediate P9-1 (3.7 g).

[0207] Preparation Example 4

[0208] This preparation example provides the intermediate P10-1, the synthesis method of which is as follows:

[0209]

[0210] (1) Synthesis of intermediate P10-0

[0211] Referring to the synthesis method of intermediate P1-0 provided in Preparation Example 1, 5-bromo-2-chloro-1,1'-biphenyl was replaced with an equal amount of The intermediate P10-0 was obtained.

[0212] The obtained intermediate P10-0 was subjected to mass spectrometry detection, and the two peaks with the largest m / z were 568.10 and 566.11.

[0213] (2) Synthesis of intermediate P10-1

[0214] Referring to the synthesis method of intermediate P9-1 provided in Preparation Example 1, intermediate P1-0 was replaced with intermediate P10-0 in an equal amount to obtain intermediate P10-1.

[0215] Preparation Example 5

[0216] This preparation example provides the intermediate P14-1BA, the synthesis method of which is as follows:

[0217]

[0218] (1) Synthesis of intermediate P14-0

[0219] Referring to the synthesis of intermediate P1-0 provided in Preparation Example 1, the method was to replace 5-bromo-2-chloro-1,1'-biphenyl with an equal amount of The intermediate P14-0 was obtained.

[0220] The obtained intermediate P14-0 was detected by mass spectrometry, and the m / z was 535.15.

[0221] (2) Synthesis of intermediate P14-1BA

[0222] Referring to the synthesis method of intermediate P1-1BA provided in Preparation Example 1, intermediate P1-0 was replaced with an equal amount of intermediate P14-0 to obtain intermediate P14-1BA.

[0223] The obtained intermediate P14-1BA was detected by mass spectrometry, and the m / z was 627.28.

[0224] Synthesis Example 1

[0225] This synthesis example provides compound P1, and its synthesis method is as follows:

[0226]

[0227] Under a nitrogen atmosphere, 100 mL of dioxane was added to a 250 mL three-necked flask in sequence, followed by 5.5 g of intermediate P1-1BA, 2.7 g of 2-chloro-4,6-diphenyl-1,3,5-triazine, 2.12 g (0.02 mol) of sodium carbonate, and 0.23 g (0.0002 mol) of tetrakistriphenylphosphine palladium. The temperature was slowly raised to reflux for 6 h, then cooled to room temperature, and separated by adding water and dichloromethane. The organic layer was washed with water, dried over magnesium sulfate, and after removing the desiccant, concentrated to dryness, and separated by silica gel column chromatography with petroleum ether: dichloromethane:THF = 10:2:1 (volume ratio) to obtain 5.5 g of compound P1.

[0228] The obtained compound P1 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 643.24.

[0229] Synthesis Example 2-15

[0230] Synthesis Examples 2-15 provide the following compounds and their synthesis methods in sequence. The synthesis method refers to the synthesis method in Synthesis Example 1, with the only difference being that the raw materials are replaced and the obtained compounds are subjected to mass spectrometry detection, and the measured mass-to-charge ratios (m / z) are shown in Table 1 below.

[0231] Table 1

[0232]

[0233]

[0234]

[0235]

[0236] Other compounds for which the specific synthesis methods are not listed can be synthesized by referring to the above examples in combination with common knowledge in the art.

[0237] The specific structures of some of the compounds used in the following application examples and comparative application examples of the present invention are as follows:

[0238]

[0239]

[0240]

[0241] Application Example 1

[0242] This application example provides a blue organic electroluminescent device, using the composition provided by the present invention as a main material of the light-emitting layer. The structure of the blue organic electroluminescent device is as follows:

[0243] ITO / HT-1: HI-2[5%](80nm) / HT-1(30nm) / EB-2(20nm) / host material: PBD-1[5%](35nm) / ETL-1(25nm) / LiF(0.5nm) / Al(150nm).

[0244] The preparation method of the blue organic electroluminescent device is as follows:

[0245] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa was vacuum evaporated onto the cleaned ITO substrate to prepare OLED devices.

[0246] PBD-1 [5%] refers to the dye doping ratio, meaning the volume ratio of the host material to the dye PBD-1 is 95:5. HT-1:HI-2 [5%] refers to the ratio of the p-type dopant, meaning the volume ratio of the hole-transporting material HT-1 to the p-type dopant HI-2 is 95:5. HT-1 is a hole-transporting material; HT-1:HI-2 [5%] serves as the hole-injection layer, and EB-2 is the electron-blocking layer.

[0247] The main materials of the light-emitting layer of the blue organic electroluminescent device provided in this application example are compounds P1 and H-1, and the volume ratio of P1 to H-1 is 1:1.

[0248] Application Example 2-21

[0249] Application Examples 2-21 each provide a blue organic electroluminescent device. The only difference from Application Example 1 is that the main material of the light-emitting layer is replaced by other compound compositions, and the volume ratio of the two compounds in the composition is 1:1 (see Table 2 below for details). The other preparation steps and conditions are the same as those in Application Example 1.

[0250] Comparative Application Examples 1-3

[0251] Comparative Application Examples 1-3 each provide an organic electroluminescent device, which differs from Application Example 1 only in that the main material 1 of the light-emitting layer is different (see Table 2 below for details). Other preparation steps and conditions are the same as those of Application Example 1.

[0252] Performance Testing

[0253] The brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above were tested, wherein the voltage and current efficiency were the values ​​of the device with a brightness of 1000 cd / m 2The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density is constant, where voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 2 below:

[0254] Table 2

[0255] Main material 1 Main material 2 <![CDATA[Luminance / (cd / m 2 )]]> Voltage Current efficiency LT95 Application Example 1 P1 H-1 1000 1 1 1 Application Example 2 P2 H-1 1000 0.88 1.23 1.09 Application Example 3 P3 H-1 1000 0.91 1.07 1.19 Application Example 4 P4 H-2 1000 0.57 1.56 3.11 Application Example 5 P4D H-2 1000 0.58 1.59 3.57 Application Example 6 P5 H-3 1000 0.92 1.11 1.17 Application Example 7 P6 H-2 1000 0.91 1.22 1.87 Application Example 8 P7 H-2 1000 1.02 1.29 2.22 Application Example 9 P8 H-2 1000 1.11 1.39 2.16 Application Example 10 P9 H-2 1000 1.02 2.09 1.77 Application Example 11 P9B H-2 1000 0.89 2.22 1.92 Application Example 12 P10 H-2 1000 1.11 0.98 1.01 Application Example 13 P11 H-2 1000 1.18 0.89 0.79 Application Example 14 P12 H-2 1000 1.01 0.76 1.11 Application Example 15 P15 H-2 1000 0.78 1.11 1.27 Application Example 16 P14 H-2 1000 0.77 1.34 1.89 Application Example 17 P16 H-2 1000 0.98 1.43 1.47 Application Example 18 P17 H-2 1000 0.59 1.76 3.78 Application Example 19 P18 H-2 1000 0.50 1.39 3.01 Application Example 20 P19 H-2 1000 0.51 1.32 2.96 Application Example 21 P23 H-2 1000 0.59 1.39 3.16 Comparative Application Example 1 D1 H-2 1000 1.55 0.41 0.70 Comparative Application Example 2 D2 H-2 1000 1.37 0.40 0.66 Comparative Application Example 3 D3 H-2 1000 1.20 0.57 0.58

[0256] As can be seen from the above, the present invention designs the structure of the nitrogen-containing compound to make it suitable as the host material of the phosphorescent light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has higher current efficiency and longer life.

[0257] Moreover, according to Application Examples 18-21, when the hydrogen atoms in the compound of Formula I can be independently replaced by at least one of a deuterium atom (D), -F, -CN, a C6-C20 aromatic group, a C1-C12 alkyl group, or a C1-C12 alkoxy group, the device voltage is lower and the life is better.

[0258] Application Examples 22-23

[0259] Application Example 22-23 provides a blue organic electroluminescent device, which differs from Application Example 1 only in that PBD-1 is replaced by PBD-2 (see Table 3 below for details), and the main material of the light-emitting layer is different. The other preparation steps and conditions are the same as those of Application Example 1.

[0260] Comparative Application Example 4

[0261] Comparative Application Example 4 provides an organic electroluminescent device, which differs from Application Example 1 only in that PBD-1 is replaced by PBD-2 (see Table 3 below for details) and the main material of the light-emitting layer is different. Other preparation steps and conditions are the same as those of Application Example 1.

[0262] Performance Testing

[0263] The brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above were tested, wherein the voltage and current efficiency are the brightness of 1000cd / m 2 The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density is constant, where voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 3 below:

[0264] Table 3

[0265] Main material 1 Main material 2 <![CDATA[Brightness / (cd / m 2 )]]> Voltage Current efficiency LT95 Application Example 22 P21 H-2D 1000 1 1 1 Application Example 23 P22 H-2D 1000 1.09 0.87 1.67 Comparative Application Example 4 D4 H-2D 1000 1.29 0.67 0.88

[0266] As can be seen from the above, the present invention designs the structure of the nitrogen-containing compound to make it suitable as the host material of the phosphorescent light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has higher current efficiency and longer life.

[0267] Application Examples 24-27, Comparative Application Examples 5-9

[0268] Application Examples 24-27 and Comparative Application Examples 5-9 provide a blue organic electroluminescent device, which differs from Application Example 1 only in that PBD-1 is replaced by PBD-2 (see Table 4 below for details), and the main material of the light-emitting layer is a single material, namely main material 1. The other preparation steps and conditions are the same as those of Application Example 1.

[0269] Performance Testing

[0270] The brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above were tested, wherein the voltage and current efficiency are the brightness of 1000cd / m 2 The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density is constant, where voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 4 below:

[0271] Table 4

[0272] Main material 1 <![CDATA[Luminance / (cd / m 2 )]]> Voltage Current efficiency LT95 Application Example 24 P4 1000 0.76 1.33 1.47 Application Example 25 P14 1000 0.68 1.29 1.92 Application Example 26 P9B 1000 0.86 1.19 1.56 Application Example 27 P11 1000 0.88 1.29 1.55 Comparative Application Example 5 D5 1000 1 1 1 Comparative Application Example 6 D6 1000 1.12 0.78 0.81 Comparative Application Example 7 D7 1000 0.89 1.02 1.16 Comparative Application Example 8 D8 1000 0.82 1.11 1.29 Comparative Application Example 9 D9 1000 1.04 1.12 1.31

[0273] In the present invention, the structure of the nitrogen-containing compound is designed to make it suitable as the main material of the phosphorescent light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has lower voltage, higher current efficiency and longer life.

[0274] The applicant declares that the present invention uses the above-described embodiments to illustrate the detailed process flow of the present invention, but the present invention is not limited to the above-described detailed process flow, that is, it does not mean that the present invention must rely on the above-described detailed process flow to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent replacements for various raw materials in the products of the present invention, addition of auxiliary ingredients, and selection of specific methods, etc., are all within the scope of protection and disclosure of the present invention.

Claims

1. A nitrogen-containing compound, characterized in that The nitrogen-containing compound has a structure shown in the following formula I: wherein Ar1, Ar2, and Ar3 are each independently selected from a C6-C40 aryl group or a C6-C30 heteroaryl group; X is selected from C or Si; A1, A2, A3 are each independently selected from N or CR, and at least one is selected from N; R is selected from any one of H, C6-C20 aryl or C1-C12 alkyl; R1 is selected from C6-C40 aryl or C6-C30 heteroaryl; R2 is selected from any one of H, C6-C40 aryl or C6-C30 heteroaryl; n is selected from 0, 1, 2 or 3; Ar 11 、Ar 12 Each is independently selected from the following groups represented by the structures A-1 to A-7, wherein "*" represents the connection position: Ar4, Ar5, Ar 6、 Ar7 are each independently selected from C6-C40 aryl or C6-C30 heteroaryl; Y is selected from C or Si; The hydrogen atoms in the compound of formula I may each independently be substituted by at least one of a deuterium atom, -F, -CN, a C6-C20 aryl group, a C1-C12 alkyl group, or a C1-C12 alkoxy group. The compounds of formula I do not include the following compounds:

2. The nitrogen-containing compound according to claim 1, characterized in that The compound of formula I has any one of the structures shown in I-1 to I-4: Among them, Ar1, Ar2, Ar3, A1, A2, A3, R1, R2, n, Ar 11 、Ar 12 Has the same definition as claim 1.

3. The nitrogen-containing compound according to claim 1 or 2, characterized in that The C6-C40 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, triphenylene, and fluoranthenyl; Preferably, the C6-C30 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, and dibenzofuranyl; Preferably, the C6-C20 aryl group is selected from any one of phenyl, biphenyl, terphenyl, and naphthyl; Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, tert-butyl, and cyclohexyl; Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy and hexyloxy.

4. The nitrogen-containing compound according to any one of claims 1 to 3, characterized in that Ar1, Ar2, Ar3, Ar4, Ar5, Ar 6、 Ar7 are each independently selected from phenyl, carbazolyl, biphenyl, naphthyl, triphenylene, dibenzothiophenyl, dibenzofuran, Any of the above, the dotted line indicates the connection site; Preferably, Ar1, Ar2, and Ar3 are each independently selected from any one of phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl; Preferably, Ar4, Ar5, Ar 6、 Ar7 are each independently selected from phenyl, naphthyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, Any of the above, the dotted line indicates the connection site; Preferably, R is selected from H or phenyl; Preferably, R1 is selected from any one of phenyl, biphenyl, naphthyl, triphenylene, dibenzofuranyl, and carbazolyl; Preferably, R2 is selected from H or phenyl; Preferably, n is selected from 1; Preferably, the hydrogen atoms in the compound of formula I can each independently be substituted by at least one of -D, -F, -CN, phenyl, naphthyl, biphenyl, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy or butoxy; Preferably, the hydrogen atoms in the compound of formula I can each independently be substituted by at least one of -D, -F, -CN, phenyl, naphthyl, methyl, ethyl, tert-butyl, methoxy, and propoxy.

5. The nitrogen-containing compound according to any one of claims 1 to 4, characterized in that The compound of formula I has the structure shown in the following formula I-5: Among them, Ar1, Ar2, Ar3, A1, A2, A3, R1, R2, Ar 11 、Ar 12 Has the same definition as claim 1.

6. The nitrogen-containing compound according to any one of claims 1 to 5, characterized in that The nitrogen-containing compound is selected from any one of the following substituted or unsubstituted compounds: The substitution means that the hydrogen atoms in the above nitrogen-containing compound can be independently replaced by deuterium atoms; preferably, the compound of formula I is selected from any one of the following compounds:

7. An intermediate, characterized in that The intermediates include compound M0, compound M1, and compound M1BA: Among them, Ar1, Ar2, Ar3, X, R1, R2, A1, A2, A 3、 Ar 11 、Ar 12 , n has the same definition as in claim 1; X3 is selected from any one of F, Cl, Br or I; The intermediate is used to prepare the nitrogen-containing compound as described in the first aspect; Preferably, the intermediate includes the following compounds:

8. A composition, characterized in that The composition includes a first component and a second component; The first component comprises the nitrogen-containing compound according to any one of claims 1 to 6; The second component includes a compound having a structure shown in the following formula II: Among them, Ar 31 、Ar 32 Each is independently selected from any one of a single bond, a C6-C40 arylene group or a C6-C30 heteroarylene group; Ar 33 Any one selected from H, C6-C40 aryl or C6-C30 heteroaryl; p1 and p2 are each independently selected from 0, 1, 2, 3 or 4; The hydrogen atoms in the compound of formula II may be substituted by at least one of a deuterium atom, -F, -CN, a C6-C20 aryl group, a C1-C12 alkyl group, a C1-C12 alkoxy group, a trimethylsilyl group, a triphenylsilyl group, and a tetraphenylmethyl group.

9. The composition according to claim 8, characterized in that The compound of formula II is selected from any one of the following substituted or unsubstituted compounds: The substitution means that the hydrogen atoms in the above compounds can each be independently replaced by a deuterium atom.

10. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a cathode and an organic thin film layer arranged between the anode and the cathode; The organic thin film layer material comprises the nitrogen-containing compound according to any one of claims 1 to 6 and / or the composition according to claim 8 or 9; Preferably, the organic thin film layer includes a light-emitting layer, and the main material of the light-emitting layer includes the nitrogen-containing compound according to any one of claims 1 to 6; Preferably, the organic electroluminescent device is a blue organic electroluminescent device.

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