Nitrogen heterocyclic derivative organic compound and application thereof, organic electroluminescent device and perovskite solar cell

Abstract

The invention relates to the technical field of organic electroluminescent devices, and discloses a nitrogen heterocyclic organic compound and application thereof, an organic electroluminescent device and a perovskite solar cell. The organic compound has a structure as shown in a formula (I). When the organic compound is applied to the organic electroluminescent device, the performance of the device can be improved, the driving voltage is reduced, the luminous efficiency is improved, and the service life is prolonged. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescent devices, and in particular to a nitrogen heterocyclic derivative organic compound and application thereof, an organic electroluminescent device and a perovskite solar cell. Background Art

[0002] The phenomenon of organic electroluminescence was first discovered by Pope et al. in 1963. They found that a single-layer crystal of anthracene could emit a faint blue light when driven by a voltage of more than 100 V. However, the driving voltage was high and the thickness of the single-crystalline anthracene was large, so it did not attract widespread attention.

[0003] It was not until 1987 that Dr. Qingyun Deng and others from Kodak reported that they had prepared a sandwich-type OLED device by vacuum thermal evaporation based on two organic semiconductor materials: 8-hydroxyquinoline aluminum with high fluorescence efficiency and good electron transport properties and aromatic diamine with good hole transport properties. At a driving voltage of less than 10V, the external quantum efficiency reached 1%, making organic electroluminescent materials and devices practical, which has greatly promoted the research on OLED materials and devices.

[0004] With the continuous development of OLED technology, the performance of OLED devices has also been widely concerned. During the research process, it was found that a device with high efficiency, long life and excellent performance requires excellent device materials and matching between the various layers of the device.

[0005] The principle of organic electroluminescence is to use organic matter to convert electrical energy into light energy. Common organic light-emitting elements generally include a structure of anode and cathode and an organic layer therebetween. The materials of the organic layer mainly include hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc.

[0006] At present, OLED or screen still has the defects of high driving voltage and low current efficiency. In order to improve these defects, on the one hand, it is necessary to find new materials with better performance and improve the performance of materials in each functional layer; on the other hand, the device structure and manufacturing process need to be further optimized.

[0007] Among them, electron transport materials play a vital role in the driving voltage and luminous efficiency of the device. In order to obtain high-performance electron transport materials, the material is required to have high electron mobility to improve the luminous efficiency and service life of the device.

[0008] From the perspective of OLED device structure and manufacturing process, there are many types of OLED device structures, such as single light-emitting layer, multi-doped light-emitting layer, multiple light-emitting layer, and stacked structure. In stacked devices, due to the different transmission rates of electrons and holes in OLED devices, the number of carriers in the light-emitting area is unbalanced, which limits the improvement of the exciton recombination rate, resulting in low device efficiency and high driving voltage. Adding CGL (Charge Generate Layer) between the light-emitting units to provide carriers for the upper and lower film layers can effectively improve the problem of unbalanced number of carriers in the device, which can not only significantly improve the luminous efficiency of the device, but also extend its service life.

[0009] Therefore, it is of great practical significance to develop high-performance electron transport materials to reduce the driving voltage of the device and improve the luminous efficiency of the device. Summary of the invention

[0010] The purpose of the present invention is to overcome the defects of the prior art, such as high driving voltage, low luminous efficiency and short service life.

[0011] In order to achieve the above object, the first aspect of the present invention provides a nitrogen heterocyclic derivative organic compound having a structure shown in formula (I):

[0012]

[0013] Wherein, in formula (I),

[0014] R 1 and R 2 are the same or different and are independently selected from unsubstituted C containing a type A heteroatom as a ring atom 3-30 aryl, C substituted by C group and containing A type heteroatom as ring atom 3-30 aryl, C substituted by a group of type B and not containing a heteroatom of type A as a ring atom 3-30 aryl; and R 1 and R 2 At least one of the following is selected from unsubstituted C containing a type A heteroatom as a ring atom 3-30 aryl, C substituted by a group of type B and not containing a heteroatom of type A as a ring atom 3-30 The aromatic group;

[0015] The A-type heteroatom is selected from at least one of N, O and S; the B-type group is selected from at least one of halogen and cyano; the C-type group is selected from at least one of halogen, C 1-12 Alkyl, C 3-8 Cycloalkyl, furyl, C 1-12At least one of the following groups: alkyl, phenyl, pyridyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, cyano, substituted or unsubstituted phenanthroline, and a group provided by leaving one H atom from any one site of the structure represented by formula (I-3); and in formula (I-3), X1 is CH or N;

[0016] L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and dibenzofuran, and the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group;

[0017] R 3 Because C 3-30 A group provided by a nitrogen-containing heterocyclic aromatic compound leaving a H atom at any site capable of leaving a H atom;

[0018] L3 is selected from at least one connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted quinazoline, substituted or unsubstituted spirobifluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted quinoline; and the optional substituents in L3 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group.

[0019] The second aspect of the present invention provides the use of the nitrogen heterocyclic derivative organic compound described in the first aspect in a perovskite solar cell and / or an organic electroluminescent device.

[0020] The third aspect of the present invention provides a perovskite solar cell, which includes a conductive glass substrate, a hole transport layer, a perovskite light absorption layer, an electron transport layer, a buffer layer and a metal electrode; the electron transport layer contains at least one of the nitrogen heterocyclic derivative organic compounds described in the first aspect of the present invention.

[0021] The fourth aspect of the present invention provides an organic electroluminescent device, wherein the organic electroluminescent device contains the nitrogen heterocyclic derivative organic compound described in the first aspect of the present invention.

[0022] The compound of the present invention has suitable HOMO and LUMO energy levels, and both HOMO and LUMO energy levels are relatively deep. The deep HOMO energy level can block holes, and the deep LUMO energy level is conducive to the injection of electrons. At the same time, the compound of the present invention can adjust the LUMO energy level in a small range, so that it has a high matching degree with the LUMO energy level of the light-emitting layer, thereby reducing the driving voltage of the device.

[0023] The compound of the present invention has high electron mobility, that is, strong electron transmission ability. The application of the compound of the present invention in an organic electroluminescent device can improve the luminous efficiency of the device.

[0024] The compound of the invention has a relatively high glass transition temperature, so that the thermal stability of the film is good, thereby increasing the service life of the device.

[0025] The organic compound of the present invention is applied to an organic electroluminescent device, and can improve the performance of the device, reduce the driving voltage, increase the luminous efficiency and prolong the service life. DETAILED DESCRIPTION

[0026] The endpoints and any values ​​of the ranges disclosed in this article are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of each range, the endpoint values ​​of each range and the individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed in this article.

[0027] In the present invention, unless otherwise specified, groups of the same type have similar explanations, and the present invention will not elaborate on them one by one.

[0028] In the absence of a special description of the substitution position, the substituent of the present invention may be present at any position in the structure that can be substituted, for example, "optionally present L1 and L2 are each independently selected from a connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and dibenzofuran", wherein any two H atoms in the benzene that can be removed can be removed to form a connecting group, and L1 and L2 can also be a connecting group provided by at least two or at least three structures selected from the above structures. For example, L1 can be a connecting group provided by benzene and dibenzofuran, and the benzene structure and the dibenzofuran structure in the group each have an H atom at any site that can remove an H atom and are removed, thereby connecting to the parent core structure. For another example, in the present invention, if the "substituted or unsubstituted quinoxalyl" is a substituted quinoxalyl, any H that can be removed can be removed and replaced.

[0029] In the present invention, "substituted or unsubstituted benzene" means that the substituents present on benzene can be at any position of benzene that can be substituted. Further, for example, when it is "phenyl-substituted benzene", the group provided by it as a connecting group is a different concept from the group provided by "biphenyl" as a connecting group. The group provided by "phenyl-substituted benzene" as a connecting group means that H at any two sites on benzene that can leave H atoms leave, and the benzene structure is connected to the parent core structure as a connecting group, and the benzene structure contains a substituted phenyl; while the group provided by "biphenyl" as a connecting group means that in the two benzene structures in biphenyl, H at each site that can leave H atoms leaves, so that the biphenyl structure is connected to the parent core structure as a connecting group.

[0030] The unsubstituted spirobifluorene structure of the present invention is a structure represented by formula (I-2).

[0031]

[0032] C 1-12 The alkyl group represents a straight chain alkyl group or a branched chain alkyl group having a total number of carbon atoms of 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12).

[0033] Unsubstituted C containing a type A heteroatom as a ring atom 3-30 The term "aryl" refers to an aromatic group having a total of 3-30 carbon atoms, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, and the group contains no substituents and contains a type A heteroatom as a ring-forming atom.

[0034] C containing a type A heteroatom as a ring atom substituted by a type C group 3-30 The term "aryl" refers to an aromatic group having a total of 3-30 carbon atoms, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, and the group contains at least one substituent selected from a group of type C, and the group contains a heteroatom of type A as a ring-forming atom.

[0035] C substituted by a group of type B and not containing a group of type A heteroatom as a ring atom 3-30The term "aryl" refers to an aromatic group having a total of 3-30 carbon atoms, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, and the group contains at least one substituent selected from a group of type B, and the group does not contain a heteroatom of type A.

[0036] C substituted by at least one halogen 1-12 Alkyl, indicating C 1-12 Any substitutable position in the alkyl group may be substituted by halogen, and the total number of substituted halogens is at least 1.

[0037] As mentioned above, the first aspect of the present invention provides a nitrogen heterocyclic derivative organic compound having a structure shown in formula (I):

[0038]

[0039] Wherein, in formula (I),

[0040] R 1 and R 2 are the same or different and are independently selected from unsubstituted C containing a type A heteroatom as a ring atom 3-30 aryl, C substituted by C group and containing A type heteroatom as ring atom 3-30 aryl, C substituted by a group of type B and not containing a heteroatom of type A as a ring atom 3-30 aryl; and R 1 and R 2 At least one of the following is selected from unsubstituted C containing a type A heteroatom as a ring atom 3-30 aryl, C substituted by a group of type B and not containing a heteroatom of type A as a ring atom 3-30 The aromatic group;

[0041] The A-type heteroatom is selected from at least one of N, O and S; the B-type group is selected from at least one of halogen and cyano; the C-type group is selected from at least one of halogen, C 1-12 Alkyl, C 3-8 Cycloalkyl, furyl, C 1-12 At least one of the following groups: alkyl, phenyl, pyridyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, cyano, substituted or unsubstituted phenanthroline, and a group provided by leaving one H atom from any one site of the structure represented by formula (I-3); and in formula (I-3), X1 is CH or N;

[0042] L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and dibenzofuran, and the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group;

[0043] R 3 Because C 3-30 A group provided by a nitrogen-containing heterocyclic aromatic compound leaving a H atom at any site capable of leaving a H atom;

[0044] L3 is selected from at least one connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted quinazoline, substituted or unsubstituted spirobifluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted quinoline; and the optional substituents in L3 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group.

[0045] Preferably, in formula (I),

[0046]

[0047] R 1 and R 2 are the same or different and are independently selected from unsubstituted C containing a type A heteroatom as a ring atom 3-30 aryl, C substituted by C group and containing A type heteroatom as ring atom 3-30 aryl, C substituted by a group of type B and not containing a heteroatom of type A as a ring atom 3-30 aryl; and R 1 and R 2 At least one of the following is selected from unsubstituted C containing a type A heteroatom as a ring atom 3-30 aryl, C substituted by a group of type B and not containing a heteroatom of type A as a ring atom 3-30 The aromatic group;

[0048] The A-type heteroatom is selected from at least one of N, O and S; the B-type group is selected from at least one of halogen and cyano; the C-type group is selected from at least one of halogen, C 1-12 Alkyl, C 3-8 Cycloalkyl, furyl, C 1-12At least one of the following groups: alkyl, phenyl, pyridyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, cyano, substituted or unsubstituted phenanthroline, and a group provided by leaving one H atom from any one site of the structure represented by formula (I-3); and in formula (I-3), X1 is CH or N;

[0049] L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and dibenzofuran, and the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group;

[0050] R 3 The group provided by the structure represented by formula (I-1) leaving a H atom at position 1, 2, 3 or 4; n R represents n substituents present at any substitutable position in the structure represented by formula (I-1), and the n substituents are the same or different and are independently selected from C 1-6 Alkyl, phenyl, pyridyl, cyano, C 3-8 A cycloalkyl group, at least one C 1-6 phenyl substituted by an alkyl group; n is 0, 1, 2, 3, 4, 5, 6 or 7;

[0051] L3 is selected from at least one connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, naphthalene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, anthracene, phenanthrene, substituted or unsubstituted spirobifluorene; and the optional substituents in L3 are selected from C 1-6 At least one of alkyl, phenyl, cyano and pyridine.

[0052] More preferably, in formula (I),

[0053] R 1 and R 2the same or different, each independently selected from a furanyl substituted or unsubstituted by a C-type group, a thienyl substituted or unsubstituted by a C-type group, a phenyl substituted by a B-type group, a naphthyl substituted by a B-type group, a biphenyl substituted by a B-type group, an anthracenyl substituted by a B-type group, a phenanthryl substituted by a B-type group, a quinolyl substituted or unsubstituted by a C-type group, an isoquinolyl substituted or unsubstituted by a C-type group, a dibenzofuranyl substituted or unsubstituted by a C-type group, a dibenzofuranyl substituted or unsubstituted by a C-type group, Thiphenyl, fluorenyl substituted by a group of type B, pyridyl substituted or unsubstituted by a group of type C, pyrimidinyl substituted or unsubstituted by a group of type C, quinazolinyl substituted or unsubstituted by a group of type C, quinoxalinyl substituted or unsubstituted by a group of type C, benzimidazolyl substituted or unsubstituted by a group of type C, benzoxazolyl substituted or unsubstituted by a group of type C, benzothiazolyl substituted or unsubstituted by a group of type C, triazinyl substituted or unsubstituted by a group of type C, phenanthroline substituted or unsubstituted by a group of type C;

[0054] The B group is selected from at least one of halogen and cyano; the C group is selected from halogen, C 1-8 Alkyl, C 3-8 Cycloalkyl, furyl, C substituted by 1-10 halogens 1-8 At least one of the following groups: alkyl, phenyl, pyridyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, cyano, substituted or unsubstituted phenanthroline, and a group provided by leaving one H atom from any one site of the structure represented by formula (I-3); and in formula (I-3), X1 is CH or N;

[0055] L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and dibenzofuran, and the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group;

[0056] R 3 The group provided by the structure represented by formula (I-1) leaving a H atom at position 1, 2, 3 or 4; n R represents n substituents present at any substitutable position in the structure represented by formula (I-1), and the n substituents are the same or different and are independently selected from C 1-6 Alkyl, phenyl, pyridyl, cyano, C 4-8 Cycloalkyl, 1-5 C 1-6 phenyl substituted by an alkyl group; n is 0, 1, 2, 3, 4 or 5;

[0057] L3 is selected from at least one connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, naphthalene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, anthracene, and phenanthrene; and the optional substituent in L3 is selected from C 1-5 At least one of alkyl, phenyl, cyano and pyridine.

[0058] Particularly preferably, in formula (I), R 1 and R 2 the same or different, each independently selected from the group consisting of furanyl substituted or unsubstituted by a C-type group, thienyl substituted or unsubstituted by a C-type group, phenyl substituted by a B-type group, naphthyl substituted by a B-type group, biphenyl substituted by a B-type group, quinolyl substituted or unsubstituted by a C-type group, isoquinolyl substituted or unsubstituted by a C-type group, dibenzofuranyl substituted or unsubstituted by a C-type group, dibenzothiophenyl substituted or unsubstituted by a C-type group, pyridyl substituted or unsubstituted by a C-type group, pyrimidinyl substituted or unsubstituted by a C-type group, quinazolinyl substituted or unsubstituted by a C-type group, quinoxalinyl substituted or unsubstituted by a C-type group, benzimidazolyl substituted or unsubstituted by a C-type group, benzoxazolyl substituted or unsubstituted by a C-type group, benzothiazolyl substituted or unsubstituted by a C-type group, triazinyl substituted or unsubstituted by a C-type group, and phenanthroline substituted or unsubstituted by a C-type group;

[0059] The B group is selected from at least one of halogen and cyano; the C group is selected from at least one of fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, furanyl, phenyl, pyridyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, phenanthroline, and a group provided by leaving one H atom at any one site of the structure represented by formula (I-3); and in formula (I-3), X1 is CH or N;

[0060] L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and dibenzofuran, and the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group;

[0061] R 3The group provided by the structure represented by formula (I-1) leaving one H atom at position 1, 2, 3 or 4; n R represents n substituents present at any substitutable position in the structure represented by formula (I-1), and the n substituents are the same or different and are independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, phenyl, pyridyl, cyano, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-5 C 1-6 phenyl substituted by an alkyl group; n is 0, 1, 2, 3, 4 or 5;

[0062] L3 is selected from at least one connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, naphthalene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, anthracene, and phenanthrene; and the substituents optionally present in L3 are selected from at least one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, phenyl, and cyano.

[0063] According to a particularly preferred embodiment, the structure represented by formula (I) is selected from any one of compounds 1 to 256.

[0064] Further preferably, in formula (I),

[0065] R 1 and R 2 the same, selected from furanyl substituted or unsubstituted by a C group, thienyl substituted or unsubstituted by a C group, phenyl substituted by a B group, naphthyl substituted by a B group, biphenyl substituted by a B group, quinolyl substituted or unsubstituted by a C group, isoquinolyl substituted or unsubstituted by a C group, dibenzofuranyl substituted or unsubstituted by a C group, dibenzothiophenyl substituted or unsubstituted by a C group, pyridyl substituted or unsubstituted by a C group, pyrimidinyl substituted or unsubstituted by a C group, quinazolinyl substituted or unsubstituted by a C group, quinoxalinyl substituted or unsubstituted by a C group, benzimidazolyl substituted or unsubstituted by a C group, benzoxazolyl substituted or unsubstituted by a C group, benzothiazolyl substituted or unsubstituted by a C group, triazinyl substituted or unsubstituted by a C group, phenanthroline substituted or unsubstituted by a C group;

[0066] The B group is selected from at least one of halogen and cyano; the C group is selected from at least one of fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, furanyl, phenyl, pyridyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, a group provided by leaving one H atom at any one site of the structure represented by formula (I-1), and a group provided by leaving one H atom at any one site of the structure represented by formula (I-3); and in formula (I-3), X1 is CH or N;

[0067] L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and dibenzofuran, and the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group;

[0068] R 3 The group provided by the structure represented by formula (I-1) leaving one H atom at position 1; n R represents n substituents present at any substitutable position in the structure represented by formula (I-1), and the n substituents are the same or different and are independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, phenyl, pyridyl, cyano, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-5 C 1-6 phenyl substituted by an alkyl group; n is 0, 1, 2, 3, 4 or 5;

[0069] L3 is selected from at least one connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, naphthalene, anthracene, and phenanthrene; and the substituents optionally present in L3 are selected from at least one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, phenyl, cyano, and pyridyl.

[0070] According to a particularly preferred embodiment, the structure shown in formula (I) is selected from any one of compounds 1 to 256, but does not include compound 12, compound 16, compound 19, compound 20, compound 52, compound 59, compound 60, compound 83, compound 84, compound 91, compound 92, compound 99, compound 100, compound 107, compound 108, compound 115, compound 116, compound 124, compound 125, compound 139, compound 140, compound 147, compound 148, compound 155, compound 156, compound 163, compound 164, compound 171, compound 172, compound 179, compound 180, compound 187, compound 188, compound 195, compound 196, compound 234, compound 235, compound 238 and compound 239.

[0071] The present invention has no particular limitation on the specific method for preparing the aforementioned organic compounds. Those skilled in the art can obtain the aforementioned compounds of the present invention according to the specific structural formula provided by the present invention in combination with the known knowledge in the field of organic synthesis. In addition, several examples are exemplarily listed in the following text of the present invention to illustrate the preparation method of the organic compounds of the present invention. Those skilled in the art can also obtain the specific preparation method of all other organic compounds by replacing the types of raw materials according to the preparation method of the organic compounds in the following text of the present invention. The present invention no longer describes in detail the preparation methods of all organic compounds, and those skilled in the art should not be construed as limiting the present invention.

[0072] As mentioned above, the second aspect of the present invention provides the use of the nitrogen heterocyclic derivative organic compound described in the first aspect in a perovskite solar cell and / or an organic electroluminescent device.

[0073] As mentioned above, the third aspect of the present invention provides a perovskite solar cell, which includes a conductive glass substrate, a hole transport layer, a perovskite light absorption layer, an electron transport layer, a buffer layer and a metal electrode; the electron transport layer contains at least one of the nitrogen heterocyclic derivative organic compounds described in the first aspect of the present invention.

[0074] Preferably, the metal electrode comprises a metal cathode, and a material forming the metal cathode is selected from at least one of Al, Ag, Au, Mg, Cu, Mo and Cr.

[0075] More preferably, the perovskite light absorbing layer comprises at least one perovskite material ABY3; wherein A is NH2CH=NH2 + 、CH3NH3 + or Cs + At least one of; B is Pb2+ or Sn 2+ At least one of; Y is 1 - , Cl - or Br - At least one of .

[0076] The present invention has no special requirements for the specific preparation process of the perovskite solar cell. Those skilled in the art can adopt the process for preparing perovskite solar cells known in the art. The present invention will not be repeated here, and those skilled in the art should not understand it as a limitation of the present invention.

[0077] The fourth aspect of the present invention provides an organic electroluminescent device, wherein the organic electroluminescent device contains at least one of the nitrogen heterocyclic derivative organic compounds described in the first aspect of the present invention.

[0078] According to a preferred specific embodiment, the organic electroluminescent device of the present invention comprises: a first electrode; a second electrode arranged opposite to the first electrode; and at least one organic material layer arranged between the first electrode and the second electrode, wherein at least one of the organic material layers contains the aforementioned organic compound of the present invention.

[0079] Preferably, the organic material layer of the organic electroluminescent device of the present invention may also form a multilayer structure of two or more organic material layers. The organic electroluminescent device of the present invention may include a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron injection layer, etc. as organic material layers, and may include a charge generation layer disposed between the organic light emitting layers. However, the structure of the organic device is not limited thereto, and may include fewer or more organic layer materials.

[0080] According to a preferred embodiment of the present invention, the organic electroluminescent device of the present invention further comprises a first covering layer and / or a second covering layer, wherein the first covering layer is arranged on the outer surface of the anode, and the second covering layer is arranged on the outer surface of the cathode.

[0081] Preferably, the nitrogen heterocyclic derivative organic compound is present in at least one of an electron transport layer, a hole blocking layer and a charge generating layer of the organic electroluminescent device.

[0082] According to a particularly preferred embodiment, the organic compound is present in the electron transport layer of the organic electroluminescent device.

[0083] Particularly preferably, the organic compound is used as an electron transport material in an electron transport layer of the organic electroluminescent device.

[0084] According to another particularly preferred embodiment, the organic compound is present in the charge generation layer of the organic electroluminescent device.

[0085] More preferably, the organic electroluminescent device is provided with a first electrode, a second electrode and a light-emitting unit located between the first electrode and the second electrode, and the light-emitting unit includes a first light-emitting portion, a second light-emitting portion and a first charge generation layer located between the first light-emitting portion and the second light-emitting portion, and the first charge generation layer contains the organic compound.

[0086] Particularly preferably, the first light-emitting portion contains a hole injection layer, a first hole transport layer, a first light-emitting layer, and a first electron transport layer; and the second light-emitting portion contains a second hole transport layer, a second light-emitting layer, and a second electron transport layer.

[0087] Preferably, the charge generating material contains an n-type charge generating material and a p-type charge generating material, and the n-type charge generating material contains the organic compound.

[0088] More preferably, in the charge generating material, the weight ratio of the n-type charge generating material to the p-type charge generating material is 1:0.1-2; particularly preferably, the weight ratio of the n-type charge generating material to the p-type charge generating material is 1:0.5-1.

[0089] According to a preferred embodiment, the n-type charge generating material further contains at least one doping metal selected from the group consisting of Yb, Li, Ag, Ca and Mg.

[0090] Preferably, based on the total amount of the n-type charge generating material, the content ratio of the doping metal is 1-10 wt %.

[0091] Preferably, the organic electroluminescent device of the present invention is coated with one or more layers by means of a sublimation method. In this case, in a vacuum sublimation system, at a temperature of less than 10 -3 Pa, preferably less than 10 -6 The organic compound provided by the present invention is applied by vapor deposition at an initial pressure of 1.5 Pa.

[0092] The organic electroluminescent device of the invention is preferably coated with one or more layers by an organic vapor deposition method or by means of carrier gas sublimation. -6 The material is applied at a pressure of 100 Pa to 100 Pa. A particular example of this method is an organic vapor deposition printing method, in which the compound provided by the present invention is directly applied through a nozzle and forms a device structure.

[0093] The organic electroluminescent device of the present invention is preferably formed into a single-layer or multi-layer structure by light-induced thermal imaging or thermal transfer.

[0094] The organic electroluminescent device of the present invention preferably prepares the organic compound of the present invention into a solution, and forms a layer or a plurality of layer structures by spin coating or by means of any printing method, such as screen printing, flexographic printing, inkjet printing, lithography, and more preferably inkjet printing. However, when multiple layers are made in this way, damage between layers is likely to occur, that is, when one layer is made, when another layer is made with a solution, the solvent in the solution will destroy the already formed layer, which is not conducive to device production. The organic compound provided by the present invention can be replaced by structural modification, so that the organic compound of the present invention undergoes cross-linking under heating or ultraviolet exposure, thereby maintaining a complete layer without being destroyed. The organic compound of the present invention can also be applied from a solution and fixed in the corresponding layer by subsequent cross-linking in a polymer network.

[0095] Preferably, the organic electroluminescent device of the invention is produced by applying one or more layers from solution and by applying one or more layers by a sublimation method.

[0096] Preferably, when preparing the organic electroluminescent device of the present invention, the organic compound of the present invention or other compounds are first fully mixed, and then applied in the above manner to form one or more layers. More preferably, in a vacuum sublimation system, at a temperature of less than 10 -3 Pa, preferably less than 10 -6 The compounds are applied by vapor deposition at an initial pressure of 1.3 Pa to form one or more layers.

[0097] The present invention will be described in detail below by way of examples. In the following examples, unless otherwise specified, all the raw materials used are common commercial products. Unless otherwise specified, the room temperature described below means 25±1°C.

[0098] The present invention provides methods for preparing some of the compounds in the following specific structural formulas. The methods for preparing the remaining compounds can be carried out by referring to the methods provided below, which should not be construed as limiting the present invention by those skilled in the art.

[0099] Preparation Example 1: Synthesis of Compound 5

[0100]

[0101] Synthesis of intermediate 5-1: 0.150 mol of 2-(4-bromophenyl)-1,10-phenanthroline was dissolved in 500 ml of 1,4-dioxane solvent, and stirred under nitrogen. 0.154 mol of pinacol diboron, 0.378 mol of potassium acetate, and 0.41 mmol of ferrocene palladium dichloride were added in sequence. The temperature was raised to reflux for reaction. After 4 hours, HPLC detected that the reaction of the raw materials was basically completed, and the reaction was stopped. The reaction solution was dried under reduced pressure, and the residue was subjected to column chromatography to obtain intermediate 5-1 (yield: 69.9%).

[0102] Synthesis of intermediate 5-2: 0.62 mol of 6-methylpyridine-2-boric acid was dissolved in 850 ml of toluene solvent, nitrogen was introduced with stirring, 0.307 mol of 2-amino-4,6-dichloropyrimidine, 1.558 mol of potassium carbonate, and 1.72 mmol of tetrakis(triphenylphosphine)palladium were added in sequence, and the temperature was raised to reflux. After 6 hours, HPLC detected that the raw materials were basically reacted completely, the reaction was stopped, the temperature was lowered, and the crude product was filtered to obtain a crude product, which was completely soluble in toluene. The filtrate was decompressed and dried, and the residue was subjected to column chromatography to obtain intermediate 5-2 (yield: 58.8%).

[0103] Synthesis of intermediate 5-3: Dissolve 0.180 mol of intermediate 5-2 in 500 ml of N,N-dimethylformamide under nitrogen protection, add 180 ml of saturated N,N-dimethylformamide solution containing N-bromosuccinimide (0.180 mol) dropwise, raise the temperature to 100°C and stir for 20 hours. HPLC detection shows that the reaction of the raw materials is basically complete. Cool the reaction solution to room temperature, add water to quench, stir for 30 minutes, filter to obtain the crude product, dry and recrystallize to obtain intermediate 5-3 (yield: 60.8%).

[0104] Synthesis of compound 5: 0.107 mol of intermediate 5-3 was dissolved in 380 ml of toluene solvent, nitrogen was introduced with stirring, 0.107 mol of intermediate 5-1, 0.268 mol of potassium carbonate, and 0.35 mmol of tetrakis(triphenylphosphine)palladium were added in sequence, the temperature was raised to reflux, and after 5 h, HPLC detection showed that the raw materials were basically reacted completely, the reaction was stopped, the temperature was lowered and filtered to obtain a crude product, which was completely soluble in toluene. The filtrate was decompressed and dried, and the residue was subjected to column chromatography to obtain compound 5 (yield: 70.4%).

[0105] Mass spectrum: C34H25N7, theoretical value: 531.22, measured value: 531.2. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.93 ~ 1.95 (2H, s), 2.74 ~ 2.78 (6H, s), 7.08 ~ 7.14 (2H, m), 7.22 ~ 7.36 (3H, m), 7.52 ~ 7.61 (2H, m), 7.72 ~ 7.80 (2H, m), 7.85 ~ 7.90 (1H, m), 8.21 ~ 8.26 (2H, m), 8.36 ~ 8.48 (2H, m), 8.66 ~ 8.72 (2H, m), 8.77 ~ 8.82 (1H, m).

[0106] Preparation Example 2: Synthesis of Compound 11

[0107]

[0108] Synthesis of intermediate 11-1: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 11-1 (yield: 57.4%).

[0109] Synthesis of intermediate 11-2: The synthesis method is the same as that of intermediate 5-3 to obtain intermediate 11-1 (yield: 58.6%).

[0110] Synthesis of Compound 11: The synthesis method was the same as that of Compound 5 to obtain Compound 11 (yield: 72.0%).

[0111] Mass spectrum: C42H27N9, theoretical value: 657.24, measured value: 657.2. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.99 ~ 2.03 (2H, s), 7.17 ~ 7.37 (5H, m), 7.51 ~ 7.61 (2H, m), 7.69 ~ 7.91 (5H, m), 8.10 ~ 8.17 (2H, m), 8.36 ~ 8.47 (2H, m), 8.52 ~ 8.57 (2H, m), 8.66 ~ 8.72 (2H, m), 8.77 ~ 8.83 (1H, m), 9.15 ~ 9.32 (4H, m).

[0112] Preparation Example 3: Synthesis of Compound 19

[0113]

[0114] Synthesis of intermediate 19-1: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 19-1 (yield: 56.7%).

[0115] Synthesis of intermediate 19-2: The synthesis method is the same as that of intermediate 5-1 to obtain intermediate 19-2 (yield: 68.6%).

[0116] Synthesis of intermediate 19-3: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 19-3 (yield: 58.6%).

[0117] Synthesis of intermediate 19-4: The synthesis method is the same as that of intermediate 5-3 to obtain intermediate 19-4 (yield: 57.2%).

[0118] Synthesis of Compound 19: The synthesis method was the same as that of Compound 5 to obtain Compound 19 (yield: 70.2%).

[0119] Mass spectrum: C47H30N8, theoretical value: 706.26, measured value: 706.2. 1H-NMR (400MHz, CDCl3) (ppm) δ = 2.10 ~ 2.13 (2H, s), 7.21 ~ 7.37 (3H, m), 7.43 ~ 7.69 (10H, m), 7.76 ~ 8.04 (7H, m), 8.31 ~ 8.49 (4H, m), 8.65 ~ 8.72 (2H, m), 8.77 ~ 8.83 (1H, m), 8.93 ~ 9.01 (1H, m).

[0120] Preparation Example 4: Synthesis of Compound 31

[0121]

[0122] Synthesis of intermediate 31-1: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 31-1 (yield: 58.1%).

[0123] Synthesis of intermediate 31-2: The synthesis method is the same as that of intermediate 5-3 to obtain intermediate 31-1 (yield: 57.2%).

[0124] Synthesis of compound 31: The synthesis method was the same as that of compound 5 to obtain compound 31 (yield: 74.1%).

[0125] Mass spectrum: C36H21N7O2, theoretical value: 583.18, measured value: 583.1. 1H-NMR (400MHz, CDCl3) (ppm) δ = 2.08 ~ 2.10 (2H, s), 7.21 ~ 7.42 (7H, m), 7.52 ~ 7.61 (2H, m), 7.69 ~ 7.78 (4H, m), 7.85 ~ 7.91 (1H, m), 8.36 ~ 8.48 (2H, m), 8.66 ~ 8.72 (2H, m), 8.78 ~ 8.83 (1H, m).

[0126] Preparation Example 5: Synthesis of Compound 37

[0127]

[0128] Synthesis of intermediate 37-1: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 37-1 (yield: 56.5%).

[0129] Synthesis of intermediate 37-2: The synthesis method is the same as that of intermediate 5-3 to obtain intermediate 37-1 (yield: 59.4%).

[0130] Synthesis of compound 37: The synthesis method was the same as that of compound 5 to obtain compound 37 (yield: 72.4%).

[0131] Mass spectrum: C36H21N7, theoretical value: 551.19, measured value: 551.1. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.96 ~ 1.99 (2H, s), 7.22 ~ 7.37 (3H, m), 7.52 ~ 7.60 (2H, m), 7.65 ~ 7.78 (4H, m), 7.85 ~ 7.91 (1H, m), 7.97 ~ 8.01 (2H, m), 8.09 ~ 8.15 (2H, m), 8.36 ~ 8.48 (2H, m), 8.66 ~ 8.72 (2H, m), 8.77 ~ 8.83 (1H, m).

[0132] Preparation Example 6: Synthesis of Compound 101

[0133]

[0134] Synthesis of intermediate 101-1: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 101-1 (yield: 58.1%).

[0135] Synthesis of intermediate 101-2: The synthesis method is the same as that of intermediate 5-3 to obtain intermediate 101-1 (yield: 58.7%).

[0136] Synthesis of intermediate 101-3: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 101-3 (yield: 57.5%).

[0137] Synthesis of intermediate 101-4: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 101-4 (yield: 54.6%).

[0138] Synthesis of intermediate 101-5: The synthesis method is the same as that of intermediate 5-1 to obtain intermediate 101-5 (yield: 65.4%).

[0139] Synthesis of Compound 101: The synthesis method was the same as that of Compound 5 to obtain Compound 101 (yield: 72.8%).

[0140] Mass spectrum: C50H33N7, theoretical value: 731.28, measured value: 731.2. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.96 ~ 1.98 (2H, s), 7.22 ~ 7.28 (2H, m), 7.36 ~ 7.63 (12H, m), 7.75 ~ 8.07 (9H, m), 8.25 ~ 8.32 (2H, m), 8.37 ~ 8.43 (2H, m), 8.65 ~ 8.77 (4H, m).

[0141] Preparation Example 7: Synthesis of Compound 110

[0142]

[0143] Synthesis of intermediate 110-1: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 110-1 (yield: 57.8%).

[0144] Synthesis of intermediate 110-2: The synthesis method is the same as that of intermediate 5-3 to obtain intermediate 110-1 (yield: 57.9%).

[0145] Synthesis of intermediate 110-3: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 110-3 (yield: 55.7%).

[0146] Synthesis of intermediate 110-4: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 110-4 (yield: 56.4%).

[0147] Synthesis of intermediate 110-5: The synthesis method is the same as that of intermediate 5-1 to obtain intermediate 110-5 (yield: 64.4%).

[0148] Synthesis of Compound 110: The synthesis method was the same as that of Compound 5 to obtain Compound 110 (yield: 70.3%).

[0149] Mass spectrum: C42H34N8, theoretical value: 650.29, found value: 650.2. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.93 ~ 1.96 (2H, s), 2.38 ~ 2.41 (6H, s), 2.55 ~ 2.58 (6H, s), 2.75 ~ 2.77 (3H, s), 6.73 ~ 7.77 (1H, m), 7.23 ~ 7.27 (2H, m), 7. 32~7.36 (1H, s), 7.46~7.50 (1H, m), 7.55~7.59 (1H, m), 7.73~7.77 (4H, s), 7.80~7.84 (1H, m), 8 .03~8.07(1H,m), 8.37~8.40(1H,m), 8.44~8.48(1H,s), 8.67~8.71(2H,m), 9.00~9.03(1H,m).

[0150] Preparation Example 8: Synthesis of Compound 149

[0151]

[0152] Synthesis of intermediate 149-1: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 149-1 (yield: 58.4%).

[0153] Synthesis of intermediate 149-2: The synthesis method is the same as that of intermediate 5-1 to obtain intermediate 149-2 (yield: 68.1%).

[0154] Synthesis of Compound 149: The synthesis method was the same as that of Compound 5 to obtain Compound 149 (yield: 75.1%).

[0155] Mass spectrum: C38H25N7, theoretical value: 579.22, measured value: 579.2. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.91 ~ 1.94 (2H, s), 7.31 ~ 7.36 (1H, d), 7.52 ~ 7.74 (9H, m), 7.85 ~ 8.06 (4H, m), 8.30 ~ 8.48 (6H, m), 8.71 ~ 8.83 (3H, m).

[0156] Preparation Example 9: Synthesis of Compound 167

[0157]

[0158] Synthesis of intermediate 167-1: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 167-1 (yield: 56.9%).

[0159] Synthesis of intermediate 167-2: The synthesis method is the same as that of intermediate 5-3 to obtain intermediate 167-1 (yield: 54.1%).

[0160] Synthesis of intermediate 167-3: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 167-3 (yield: 59.7%).

[0161] Synthesis of intermediate 167-4: The synthesis method is the same as that of intermediate 5-1 to obtain intermediate 167-4 (yield: 72.5%).

[0162] Synthesis of Compound 167: The synthesis method was the same as that of Compound 5 to obtain Compound 167 (yield: 72.1%).

[0163] Mass spectrum: C54H35N7, theoretical value: 781.30, measured value: 781.3. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.96 ~ 1.98 (2H, s), 7.20 ~ 7.69 (20H, m), 7.85 ~ 7.90 (1H, m), 7.97 ~ 8.03 (2H, m), 8.14 ~ 8.19 (1H, d), 8.29 ~ 8.48 (6H, m), 8.77 ~ 8.83 (1H, m), 8.92 ~ 9.04 (2H, m).

[0164] Preparation Example 10: Synthesis of Compound 198

[0165]

[0166] Synthesis of intermediate 198-1: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 198-1 (yield: 53.8%).

[0167] Synthesis of intermediate 198-2: The synthesis method is the same as that of intermediate 5-3 to obtain intermediate 198-1 (yield: 58.0%).

[0168] Synthesis of intermediate 198-3: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 198-3 (yield: 60.5%).

[0169] Synthesis of intermediate 198-4: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 198-4 (yield: 62.4%).

[0170] Synthesis of intermediate 198-5: The synthesis method is the same as that of intermediate 5-1 to obtain intermediate 198-5 (yield: 71.9%).

[0171] Synthesis of Compound 198: The synthesis method was the same as that of Compound 5 to obtain Compound 198 (yield: 72.4%).

[0172] Mass spectrum: C50H37N5O, theoretical value: 723.30, measured value: 723.3. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.99 ~ 2.00 (2H, s), 2.29 ~ 2.33 (12H, s), 7.23 ~ 7.46 (9H, m), 7.51 ~ 7.60 (3H, m), 7.66 ~ 7.70 (4H, m), 7.74 ~ 7.79 (1H, m), 7.85 ~ 7.91 (1H, m), 7.95 ~ 8.01 (1H, m), 8.19 ~ 8.23 ​​(1H, m), 8.36 ~ 8.48 (2H, m), 8.77 ~ 8.83 (1H, m).

[0173] Preparation Example 11: Synthesis of Compound 230

[0174]

[0175] Synthesis of intermediate 230-1: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 230-1 (yield: 50.5%).

[0176] Synthesis of Compound 230: The synthesis method was the same as that of Compound 5 to obtain Compound 230 (yield: 71.9%).

[0177] Mass spectrum: C48H37N7, theoretical value: 711.31, measured value: 711.3. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.93~1.95 (2H, s), 2.38~2.42 (6H, s), 2.54~2.58 (6H, s), 7.23~7.27 (4H, m), 7.36~7.60 (5H, m), 7.73~7.88 (9H, m), 7.93~7.95 (1H, m), 8.42~8.48 (1H, m), 8.66~8.72 (2H, m), 8.77~8.83 (1H, m).

[0178] Preparation Example 12: Synthesis of Compound 236

[0179]

[0180] Synthesis of intermediate 236-1: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 236-1 (yield: 57.4%).

[0181] Synthesis of intermediate 236-2: The synthesis method is the same as that of intermediate 5-3 to obtain intermediate 236-2 (yield: 54.5%).

[0182] Synthesis of intermediate 236-3: The synthesis method is the same as that of intermediate 5-2 to obtain intermediate 236-1 (yield: 54.2%).

[0183] Synthesis of intermediate 236-4: The synthesis method is the same as that of intermediate 5-1 to obtain intermediate 236-4 (yield: 66.6%).

[0184] Synthesis of Compound 236: The synthesis method was the same as that of Compound 5 to obtain Compound 236 (yield: 69.3%).

[0185] Mass spectrum: C43H28N8, theoretical value: 656.24, measured value: 656.2. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.98 ~ 2.01 (2H, s), 6.85 ~ 6.94 (2H, m), 7.11 ~ 7.17 (2H, m), 7.33 ~ 7.43 (2H, m), 7.51 ~ 7.60 (2H, m), 7.66 ~ 7.75 (2H, m), 7.79 ~ 7.85 (1H, m), 7.90 ~ 8.08 (4H, m), 8.28 ~ 8.49 (8H, m), 8.77 ~ 8.83 (1H, m), 8.90 ~ 9.00 (2H, m).

[0186] When the compound of the present invention is used in the electron transport layer, the structure of the organic electroluminescent device in device examples 1-1 to 1-8 and device comparative examples 1-1 to 1-3 is:

[0187] ITO / HTL:NPD-9(95:5%,10nm) / HTL(60nm) / GH:GD(90:10,30nm) / ETL:Liq(50:50,30nm) / Liq(2nm) / Al(100nm).

[0188] The molecular structure of each functional layer material is as follows:

[0189]

[0190] Device Example 1-1

[0191] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0192] The glass substrate with the anode is placed in a vacuum chamber and evacuated to 1×10 -5 Pa, vacuum evaporating a hole injection layer on the above-mentioned anode layer film, using a multi-source co-evaporation method to adjust the evaporation rate of the compound HTL to 0.1nm / s, the evaporation rate of the compound NPD-9 to 5%, and the total evaporation film thickness to 10nm; then evaporating the compound HTL as a hole transport layer, the evaporation rate is 0.1nm / s, and the thickness is 60nm; evaporating a light-emitting layer on the above-mentioned hole transport layer, the light-emitting layer includes a green light host material and a green light guest material, and using a multi-source co-evaporation method to adjust the green light The main material (GH) evaporation rate is 0.1nm / s, the green light guest material (GD) evaporation rate is set at 10%, and the total evaporation film thickness is 30nm; ETL (compound 5) is vacuum evaporated on the light-emitting layer as an electron transport layer, the evaporation rate is 0.1nm / s, the Liq evaporation rate is set at 50%, and the total evaporation film thickness is 30nm; Liq with a thickness of 2nm is vacuum evaporated on the electron transport layer as an electron injection layer, and an Al layer with a thickness of 100nm is used as the cathode of the device.

[0193] Device Examples 1-2 to 1-8

[0194] Organic light-emitting devices of Device Example 1-2 to Device Example 1-8 were prepared by a method similar to that of Device Example 1-1, except that Compound 5 in Device Example 1-1 was replaced with the compounds shown in Table 1.

[0195] Device Comparative Examples 1-1 to 1-3

[0196] Organic electroluminescent devices of device comparative examples 1-1 to 1-3 were prepared by a method similar to that of device embodiment 1-1, except that compound 5 in device embodiment 1-1 was replaced by Ref1, Ref2, and Ref3.

[0197] At brightness 10000cd / m 2 The driving voltage and current efficiency of the organic electroluminescent devices prepared in the device examples and the device comparative examples were measured. The results are shown in Table 1.

[0198] Table 1

[0199] Electron transport layer Driving voltage(V) Efficiency (cd / A) Emitting color Example 1-1 Compound 5 4.19 65.8 Green Light Example 1-2 Compound 11 4.23 65.2 Green Light Examples 1-3 Compound 19 4.41 64.0 Green Light Examples 1-4 Compound 37 4.44 63.2 Green Light Examples 1-5 Compound 110 4.31 65.1 Green Light Examples 1-6 Compound 149 4.12 66.2 Green Light Examples 1-7 Compound 198 4.39 64.5 Green Light Examples 1-8 Compound 230 7.35 65.7 Green Light Comparative Example 1-1 Ref1 4.61 57.2 Green Light Comparative Example 1-2 Ref2 4.52 56.8 Green Light Comparative Examples 1-3 Ref3 4.45 57.5 Green Light

[0200] It can be seen from the experimental results shown in Table 1 that when the organic compound of the present invention is used as the electron transport material of the organic electroluminescent device, it has a significantly lower driving voltage and a higher luminous efficiency compared with the device comparison example 1-1 and the device comparison example 1-2, and has a lower driving voltage and a significantly higher luminous efficiency compared with the device comparison example 1-3.

[0201] When the compound of the present invention is used for the n-type charge generation layer, the structure of the organic electroluminescent device in device examples 2-1 to 2-6 and device comparative examples 2-1 to 2-3 is:

[0202] ITO / HTL:NPD-9(95:5%,10nm) / HTL(60nm) / RH:RD(97:3,30nm) / ETL(10m) / n-CGL:Yb(99:1,10nm) / HT L:NPD-9(95:5,10nm) / HTL(60nm) / RH:RD(97:3,30nm) / ETL:Liq(50:50,30nm) / Liq(2nm) / Al(100nm).

[0203] The molecular structure of the relevant functional layer materials is as follows:

[0204]

[0205] Device Example 2-1

[0206] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0207] The glass substrate with the anode is placed in a vacuum chamber and evacuated to 1×10 -5Pa, vacuum evaporating the first hole injection layer on the above-mentioned anode layer film, using a multi-source co-evaporation method to adjust the evaporation rate of the compound HTL to 0.1nm / s, the evaporation rate of the compound NPD-9 to 5%, and the total evaporation film thickness to 10nm; then evaporating the compound HTL as the first hole transport layer, the evaporation rate is 0.1nm / s, and the thickness is 60nm; evaporating the first light-emitting layer on the above-mentioned hole transport layer, the light-emitting layer includes a red light host material and a red light guest material, and using a multi-source co-evaporation method to adjust the red The evaporation rate of the light host material (RH) is 0.1nm / s, the evaporation rate of the red light guest material (RD) is set at 3%, and the total evaporation film thickness is 30nm; ETL is vacuum evaporated on the light-emitting layer as the first electron transport layer, the evaporation rate is 0.1nm / s, and the total evaporation film thickness is 30nm; the n-type charge generation layer (n-CGL) is vacuum evaporated on the electron transport layer, and the multi-source co-evaporation method is used to adjust the evaporation rate of the n-type charge generation layer (compound 5) to 0.1nm / s, and the Yb evaporation rate is 1% The ratio is set, and the total film thickness of the evaporation is 10nm; on this, a p-type charge generation layer is vacuum evaporated, and the evaporation rate of the compound HTL is adjusted to 0.1nm / s by using a multi-source co-evaporation method, and the evaporation rate of the compound NPD-9 is set to 5%, and the total film thickness of the evaporation is 10nm; then, the compound HTL is evaporated as the second hole transport layer, and the evaporation rate is 0.1nm / s, and the thickness is 60nm; the second light-emitting layer is evaporated on the above hole transport layer, and the light-emitting layer includes a red light host material and a red light guest material, and the multi-source co-evaporation method is used to adjust the evaporation rate of the compound HTL to 0.1nm / s ... thickness is 60nm; The method of source co-evaporation is to adjust the evaporation rate of the red light host material (RH) to 0.1nm / s, the evaporation rate of the red light guest material (RD) to 3%, and the total evaporation film thickness to 30nm; vacuum evaporate ETL as the second electron transport layer on the light-emitting layer, the evaporation rate is 0.1nm / s, the Liq evaporation rate is set to 50%, and the total evaporation film thickness is 30nm; vacuum evaporate Liq with a thickness of 2nm on the electron transport layer as an electron injection layer, and an Al layer with a thickness of 100nm as the cathode of the device.

[0208] Device Examples 2-2 to 2-6

[0209] Organic light-emitting devices of Device Example 2-2 to Device Example 2-6 were prepared by a method similar to that of Device Example 2-1, except that Compound 5 in Device Example 2-1 was replaced with the compounds shown in Table 2.

[0210] Device Comparative Examples 2-1 to 2-3

[0211] Organic electroluminescent devices of device comparative examples 2-1 to 2-3 were prepared by a method similar to that of device embodiment 2-1, except that compound 5 in device embodiment 2-1 was replaced by Ref1, Ref2, and Ref3.

[0212] At brightness 2000cd / m 2 The driving voltage and current efficiency of the organic electroluminescent devices prepared in the device examples and the device comparative examples were measured. The results are shown in Table 2.

[0213] Table 2

[0214] n-CGL Materials Driving voltage(V) Current efficiency cd / A) Emitting color Example 2-1 Compound 5 6.81 27.23 Red light Example 2-2 Compound 31 7.17 26.72 Red light Example 2-3 Compound 101 7.03 26.94 Red light Embodiment 2-4 Compound 167 6.92 26.99 Red light Embodiment 2-5 Compound 230 6.89 27.05 Red light Embodiment 2-6 Compound 236 6.91 27.00 Red light Comparative Example 2-1 Ref1 8.89 18.19 Red light Comparative Example 2-2 Ref2 8.58 18.25 Red light Comparative Examples 2-3 Ref3 7.21 26.29 Red light

[0215] It can be seen from the experimental results shown in Table 2 that when the organic compound of the present invention is used as the n-type charge generation layer of the organic electroluminescent device, it has a significantly lower driving voltage and a higher luminous efficiency than the comparative example.

[0216] When the compound of the present invention is used for the n-type charge generation layer, the structure of the organic electroluminescent device in device examples 3-1 to 3-6 and device comparative examples 3-1 to 3-3 is:

[0217] ITO / HTL:NPD-9(95:5%,10nm) / HTL(60nm) / BH:BD(95:5,30nm) / ETL1(10m) / n-CGL:Yb(99:1,10nm) / HTL:NPD-9(95:5,10 nm) / HTL(60nm) / GH:GD(90:10,30nm) / RH:RD(97:3,30nm) / ETL1:Liq(50:50,30nm) / Yb(1nm) / Mg / Ag(12nm) / Alq3(60nm).

[0218] The molecular structure of the relevant functional layer materials is as follows:

[0219]

[0220] Device Example 3-1

[0221] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0222] The glass substrate with the anode is placed in a vacuum chamber and evacuated to 1×10-5Pa. Ag is vacuum-deposited on the anode layer as a reflective electrode layer at a rate of 0.1nm / s and a total film thickness of 100nm. The first hole injection layer is vacuum-deposited on the reflective electrode layer. The evaporation rate of the compound HT is adjusted to 0.1nm / s by a multi-source co-evaporation method, and the evaporation rate of the compound NPD-9 is set at 5%, and the total film thickness of 10nm; then the compound HTL is evaporated as the first hole transport layer at a rate of 0.1nm / s and a thickness of 60nm; the first luminescent layer is evaporated on the hole transport layer. The luminescent layer includes a blue light host material and a blue light guest material. The evaporation rate of the blue light host material (BH) is adjusted to 0.1nm / s by a multi-source co-evaporation method, and the evaporation rate of the blue light guest material (BD) is set at 5%, and the total film thickness of 30nm; ETL was vacuum evaporated on the light-emitting layer as the first electron transport layer, the evaporation rate was 0.1nm / s, and the total evaporation film thickness was 10nm; an n-type charge generation layer (n-CGL) was vacuum evaporated on the electron transport layer, and the evaporation rate of the n-type charge generation layer (compound 5) was adjusted to 0.1nm / s by a multi-source co-evaporation method, the Yb evaporation rate was set at 1%, and the total evaporation film thickness was 10nm; a p-type charge generation layer was vacuum evaporated on it, and the evaporation rate of the compound HTL was adjusted to 0.1nm / s by a multi-source co-evaporation method, the evaporation rate of the compound NPD-9 was set at 5%, and the total evaporation film thickness was 10nm; then, the compound HTL was evaporated as the first The second hole transport layer has a deposition rate of 0.1 nm / s and a thickness of 60 nm. A second light-emitting layer is deposited on the hole transport layer. The light-emitting layer includes a green light host material and a green light guest material. The deposition rate of the green light host material (GH) is adjusted to 0.1 nm / s by a multi-source co-evaporation method. The deposition rate of the green light guest material (GD) is set to 10%. The total deposition thickness is 30 nm. A third light-emitting layer is deposited on the hole transport layer. The light-emitting layer includes a red light host material and a red light guest material. The deposition rate of the red light host material (RH) is adjusted to 0.1 nm / s by a multi-source co-evaporation method. The deposition rate of the red light guest material (RD) is set to 3%. The total deposition thickness is 30 nm. The film thickness is 30nm; ETL is vacuum evaporated on the light-emitting layer as the second electron transport layer, the evaporation rate is 0.1nm / s, the Liq evaporation rate is set at 50%, and the total evaporation film thickness is 30nm; the electron injection material Yb is vacuum evaporated on the electron transport layer, the evaporation rate is 0.1nm / s, and the total evaporation film thickness is 1nm; the cathode material is vacuum evaporated on the electron injection layer, and the Ag evaporation rate is adjusted to 0.1nm / s by a multi-source co-evaporation method, the Mg evaporation rate is set at 10%, and the total evaporation film thickness is 12nm; an optical coupling layer (CPL) is vacuum evaporated on the cathode material, the Alq3 evaporation rate is 0.1nm / s, and the thickness is 60nm.

[0223] Device Examples 3-2 to 3-6

[0224] Organic light-emitting devices of device examples 3-2 to 3-6 were prepared by a method similar to that of device example 3-1, except that compound 5 in device example 3-1 was replaced with a compound shown in Table 3.

[0225] Device Comparative Examples 3-1 to 3-3

[0226] Organic electroluminescent devices of device comparison examples 3-1 to 3-3 were prepared by a method similar to that of device example 3-1, except that compound 5 in device example 3-1 was replaced by Ref1, Ref2, and Ref3.

[0227] At a current density of 20 mA / cm 2 The driving voltage and current efficiency of the organic electroluminescent devices prepared in the device examples and the device comparative examples were measured. The results are shown in Table 3.

[0228] Table 3

[0229] n-CGL Materials Driving voltage(V) Current efficiency (cd / A) Emitting color Example 3-1 Compound 5 7.21 39.43 White light Example 3-2 Compound 31 7.57 38.23 White light Example 3-3 Compound 101 7.43 38.79 White light Embodiment 3-4 Compound 167 7.32 38.97 White light Embodiment 3-5 Compound 230 7.29 39.14 White light Embodiment 3-6 Compound 236 7.31 39.08 White light Comparative Example 3-1 Ref1 9.91 28.17 White light Comparative Example 3-2 Ref2 9.56 28.15 White light Comparative Example 3-3 Ref3 7.80 37.05 White light

[0230] It can be seen from the experimental results shown in Table 3 that when the organic compound of the present invention is used as the n-type charge generation layer of the organic electroluminescent device, it has a significantly lower driving voltage and a higher luminous efficiency than the comparative example.

[0231] The preferred embodiments of the present invention are described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, the technical solution of the present invention can be subjected to a variety of simple modifications, including the combination of various technical features in any other suitable manner, and these simple modifications and combinations should also be regarded as the contents disclosed by the present invention and belong to the protection scope of the present invention.

Claims

1. A nitrogen heterocyclic organic compound, characterized in that The organic compound has a structure shown in formula (I): Wherein, in formula (I), R 1 and R 2 are the same or different and are independently selected from unsubstituted C containing a type A heteroatom as a ring atom 3-30 aryl, C substituted by C group and containing A type heteroatom as ring atom 3-30 aryl, C substituted by a group of type B and not containing a heteroatom of type A as a ring atom 3-30 aryl; and R 1 and R 2 At least one of the following is selected from unsubstituted C containing a type A heteroatom as a ring atom 3-30 aryl, C substituted by a group of type B and not containing a heteroatom of type A as a ring atom 3-30 The aromatic group; The A-type heteroatom is selected from at least one of N, O and S; the B-type group is selected from at least one of halogen and cyano; the C-type group is selected from at least one of halogen, C 1-12 Alkyl, C 3-8 Cycloalkyl, furyl, C 1-12 At least one of the following groups: alkyl, phenyl, pyridyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, cyano, substituted or unsubstituted phenanthroline, and a group provided by leaving one H atom from any one site of the structure represented by formula (I-3); and in formula (I-3), X1 is CH or N; L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and dibenzofuran, and the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group; R 3 Because C 3-30 A group provided by a nitrogen-containing heterocyclic aromatic compound leaving a H atom at any site capable of leaving a H atom; L3 is selected from at least one connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted quinazoline, substituted or unsubstituted spirobifluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted quinoline; and the optional substituents in L3 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group.

2. The nitrogen heterocyclic organic compound according to claim 1, wherein In formula (I), R 1 and R 2 are the same or different and are independently selected from unsubstituted C containing a type A heteroatom as a ring atom 3-30 aryl, C substituted by C group and containing A type heteroatom as ring atom 3-30 aryl, C substituted by a group of type B and not containing a heteroatom of type A as a ring atom 3-30 aryl; and R 1 and R 2 At least one of the following is selected from unsubstituted C containing a type A heteroatom as a ring atom 3-30 aryl, C substituted by a group of type B and not containing a heteroatom of type A as a ring atom 3-30 The aromatic group; The A-type heteroatom is selected from at least one of N, O and S; the B-type group is selected from at least one of halogen and cyano; the C-type group is selected from at least one of halogen, C 1-12 Alkyl, C 3-8 Cycloalkyl, furyl, C 1-12 At least one of the following groups: alkyl, phenyl, pyridyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, cyano, substituted or unsubstituted phenanthroline, and a group provided by leaving one H atom from any one site of the structure represented by formula (I-3); and in formula (I-3), X1 is CH or N; L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and dibenzofuran, and the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group; R 3 The group provided by the structure represented by formula (I-1) leaving a H atom at position 1, 2, 3 or 4; n R represents n substituents present at any substitutable position in the structure represented by formula (I-1), and the n substituents are the same or different and are independently selected from C 1-6 Alkyl, phenyl, pyridyl, cyano, C 3-8 A cycloalkyl group, at least one C 1-6 phenyl substituted by an alkyl group; n is 0, 1, 2, 3, 4, 5, 6 or 7; L3 is selected from at least one connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, naphthalene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, anthracene, phenanthrene, substituted or unsubstituted spirobifluorene; and the optional substituents in L3 are selected from C 1-6 At least one of alkyl, phenyl, cyano and pyridine.

3. The nitrogen heterocyclic derivative organic compound according to claim 2, wherein In formula (I), R 1 and R 2 the same or different, each independently selected from a furanyl substituted or unsubstituted by a C-type group, a thienyl substituted or unsubstituted by a C-type group, a phenyl substituted by a B-type group, a naphthyl substituted by a B-type group, a biphenyl substituted by a B-type group, an anthracenyl substituted by a B-type group, a phenanthryl substituted by a B-type group, a quinolyl substituted or unsubstituted by a C-type group, an isoquinolyl substituted or unsubstituted by a C-type group, a dibenzofuranyl substituted or unsubstituted by a C-type group, a dibenzofuranyl substituted or unsubstituted by a C-type group, Thiphenyl, fluorenyl substituted by a group of type B, pyridyl substituted or unsubstituted by a group of type C, pyrimidinyl substituted or unsubstituted by a group of type C, quinazolinyl substituted or unsubstituted by a group of type C, quinoxalinyl substituted or unsubstituted by a group of type C, benzimidazolyl substituted or unsubstituted by a group of type C, benzoxazolyl substituted or unsubstituted by a group of type C, benzothiazolyl substituted or unsubstituted by a group of type C, triazinyl substituted or unsubstituted by a group of type C, phenanthroline substituted or unsubstituted by a group of type C; The B group is selected from at least one of halogen and cyano; the C group is selected from halogen, C 1-8 Alkyl, C 3-8 Cycloalkyl, furyl, C substituted by 1-10 halogens 1-8 At least one of the following groups: alkyl, phenyl, pyridyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, cyano, substituted or unsubstituted phenanthroline, and a group provided by leaving one H atom from any one site of the structure represented by formula (I-3); and in formula (I-3), X1 is CH or N; L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and dibenzofuran, and the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group; R 3 The group provided by the structure represented by formula (I-1) leaving a H atom at position 1, 2, 3 or 4; n R represents n substituents present at any substitutable position in the structure represented by formula (I-1), and the n substituents are the same or different and are independently selected from C 1-6 Alkyl, phenyl, pyridyl, cyano, C 4-8 Cycloalkyl, 1-5 C 1-6 phenyl substituted by an alkyl group; n is 0, 1, 2, 3, 4 or 5; L3 is selected from at least one connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, naphthalene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, anthracene, and phenanthrene; and the optional substituent in L3 is selected from C 1-5 At least one of alkyl, phenyl, cyano and pyridine.

4. The nitrogen heterocyclic derivative organic compound according to any one of claims 1 to 3, wherein In formula (I), R 1 and R 2 the same or different, each independently selected from the group consisting of furanyl substituted or unsubstituted by a C-type group, thienyl substituted or unsubstituted by a C-type group, phenyl substituted by a B-type group, naphthyl substituted by a B-type group, biphenyl substituted by a B-type group, quinolyl substituted or unsubstituted by a C-type group, isoquinolyl substituted or unsubstituted by a C-type group, dibenzofuranyl substituted or unsubstituted by a C-type group, dibenzothiophenyl substituted or unsubstituted by a C-type group, pyridyl substituted or unsubstituted by a C-type group, pyrimidinyl substituted or unsubstituted by a C-type group, quinazolinyl substituted or unsubstituted by a C-type group, quinoxalinyl substituted or unsubstituted by a C-type group, benzimidazolyl substituted or unsubstituted by a C-type group, benzoxazolyl substituted or unsubstituted by a C-type group, benzothiazolyl substituted or unsubstituted by a C-type group, triazinyl substituted or unsubstituted by a C-type group, and phenanthroline substituted or unsubstituted by a C-type group; The B group is selected from at least one of halogen and cyano; the C group is selected from at least one of fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, furanyl, phenyl, pyridyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, phenanthroline, and a group provided by leaving one H atom at any one site of the structure represented by formula (I-3); and in formula (I-3), X1 is CH or N; L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and dibenzofuran, and the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group; R 3 The group provided by the structure represented by formula (I-1) leaving one H atom at position 1, 2, 3 or 4; n R represents n substituents present at any substitutable position in the structure represented by formula (I-1), and the n substituents are the same or different and are independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, phenyl, pyridyl, cyano, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-5 C 1-6 phenyl substituted by an alkyl group; n is 0, 1, 2, 3, 4 or 5; L3 is at least one connecting group provided by at least one structure selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, naphthalene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, anthracene, and phenanthrene; and the substituents optionally present in L3 are selected from at least one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, phenyl, and cyano; Preferably, the structure represented by formula (I) is selected from any one of the following structures:

5. The nitrogen heterocyclic derivative organic compound according to any one of claims 1 to 3, wherein In formula (I), R 1 and R 2 the same, selected from furanyl substituted or unsubstituted by a C group, thienyl substituted or unsubstituted by a C group, phenyl substituted by a B group, naphthyl substituted by a B group, biphenyl substituted by a B group, quinolyl substituted or unsubstituted by a C group, isoquinolyl substituted or unsubstituted by a C group, dibenzofuranyl substituted or unsubstituted by a C group, dibenzothiophenyl substituted or unsubstituted by a C group, pyridyl substituted or unsubstituted by a C group, pyrimidinyl substituted or unsubstituted by a C group, quinazolinyl substituted or unsubstituted by a C group, quinoxalinyl substituted or unsubstituted by a C group, benzimidazolyl substituted or unsubstituted by a C group, benzoxazolyl substituted or unsubstituted by a C group, benzothiazolyl substituted or unsubstituted by a C group, triazinyl substituted or unsubstituted by a C group, phenanthroline substituted or unsubstituted by a C group; The B group is selected from at least one of halogen and cyano; the C group is selected from at least one of fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, furanyl, phenyl, pyridyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, a group provided by leaving one H atom at any one site of the structure represented by formula (I-1), and a group provided by leaving one H atom at any one site of the structure represented by formula (I-3); and in formula (I-3), X1 is CH or N; L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by at least one structure of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, and dibenzofuran, and the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a pyridine group, and a cyano group; R 3 The group provided by the structure represented by formula (I-1) leaving one H atom at position 1; n R represents n substituents present at any substitutable position in the structure represented by formula (I-1), and the n substituents are the same or different and are independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, phenyl, pyridyl, cyano, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-5 C 1-6 phenyl substituted by an alkyl group; n is 0, 1, 2, 3, 4 or 5; L3 is at least one connecting group provided by at least one structure selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, naphthalene, anthracene, and phenanthrene; and the substituents optionally present in L3 are selected from at least one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, phenyl, cyano, and pyridyl; Preferably, the structure represented by formula (I) is selected from any one of the following structures:

6. Use of the nitrogen heterocyclic derivative organic compound according to any one of claims 1 to 5 in perovskite solar cells and / or organic electroluminescent devices.

7. A perovskite solar cell, characterized in that: The perovskite solar cell comprises a conductive glass substrate, a hole transport layer, a perovskite light absorption layer, an electron transport layer, a buffer layer and a metal electrode; wherein the electron transport layer contains at least one of the nitrogen heterocyclic derivative organic compounds described in any one of claims 1 to 5; Preferably, the metal electrode comprises a metal cathode, and the material forming the metal cathode is selected from at least one of Al, Ag, Au, Mg, Cu, Mo and Cr; Preferably, the perovskite light absorbing layer comprises at least one perovskite material ABY3; wherein A is NH2CH=NH2 + 、CH3NH3 + or Cs + At least one of; B is Pb 2+ or Sn 2+ At least one of; Y is 1 - , Cl - or Br - At least one of .

8. An organic electroluminescent device, characterized in that: The organic electroluminescent device contains at least one of the nitrogen heterocyclic derivative organic compounds described in any one of claims 1 to 5; Preferably, the nitrogen heterocyclic derivative organic compound is present in at least one of an electron transport layer, a hole blocking layer and a charge generating layer of the organic electroluminescent device.

9. The organic electroluminescent device according to claim 8, wherein: The organic compound is used as an electron transport material in the electron transport layer of the organic electroluminescent device.

10. The organic electroluminescent device according to claim 8, wherein: The organic compound is present in the charge generation layer of the organic electroluminescent device; Preferably, the organic electroluminescent device is provided with a first electrode, a second electrode and a light-emitting unit located between the first electrode and the second electrode, and the light-emitting unit includes a first light-emitting portion, a second light-emitting portion and a first charge generation layer located between the first light-emitting portion and the second light-emitting portion, and the first charge generation layer contains the organic compound; Preferably, the first light-emitting portion comprises a hole injection layer, a first hole transport layer, a first light-emitting layer, and a first electron transport layer; as well as The second light-emitting portion comprises a second hole transport layer, a second light-emitting layer, and a second electron transport layer; Preferably, the charge generating material contains an n-type charge generating material and a p-type charge generating material, and the n-type charge generating material contains the organic compound; Preferably, in the charge generating material, the weight ratio of the n-type charge generating material to the p-type charge generating material is 1:0.1-2; Preferably, the n-type charge generating material further contains at least one doping metal selected from Yb, Li, Ag, Ca and Mg; Preferably, based on the total amount of the n-type charge generating material, the content ratio of the doping metal is 1-10 wt %.

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