Phenanthroline derivative, organic electroluminescent element and electronic equipment

Abstract

The invention belongs to the technical field of organic electroluminescence, and relates to a phenanthroline derivative, an organic electroluminescence element and electronic equipment. The phenanthroline derivative has a structure as shown in a formula (1), # imgabs0 #, R1, R2, R3, R4, R5, R6 and R7 are the same or different and are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, and R1, R2, R3, R4, R5, R6 and R7 are independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl. And at least one of R1, R2, R3, R4, R5, R6 and R7 is selected from substituted or unsubstituted phenanthryl. The phenanthroline derivative can be used as an N-type charge generation layer material to prepare an organic electroluminescent element, and is a high-performance organic electroluminescent material.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescence, and more specifically, particularly relates to a phenanthroline derivative, an organic electroluminescent element, and an electronic device. Background Art

[0002] Organic semiconductor materials are diverse in synthesis, have relatively low manufacturing costs, and have excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have great potential in the applications of optoelectronic devices (such as flat panel displays and lighting).

[0003] Classified by device structure, according to the structure of the light-emitting layer, the OLED device structure is divided into various types, such as including a single light-emitting layer, a multi-doped light-emitting layer, a multiple light-emitting layer, a stacked layer, etc. structures. In a stacked device, the performance of the device is improved by adding a charge generation layer to the light-emitting unit. However, there is a lack of high-performance materials for the charge generation layer that can be used in stacked devices, and the selection space is limited when designing the device.

[0004] In such a charge generation layer for a common tandem OLED, due to the energy level difference between the N-type charge generation layer and the P-type charge generation layer, charges are generated at the interface between the P-type charge generation layer and the adjacent hole injection layer or hole transport layer, resulting in the deterioration of electron injection in the N-type charge generation layer.

[0005] When the N-type charge generation layer is doped with a metal, the metal may diffuse into the P-type charge generation layer, resulting in a reduction in the lifespan of the OLED. In particular, common materials used for the charge generation layer do not have sufficient thermal / electrical stability. Therefore, the long-term operation of the OLED causes the degradation or deterioration of the materials used for the charge generation layer. As a result, not only is the electron injection efficiency from the interface between the P-type charge generation layer and the adjacent hole injection layer or hole transport layer to the N-type charge generation layer significantly reduced, but the electron injection efficiency from the N-type charge generation layer to the adjacent electron transport layer is also significantly reduced, leading to a reduction in the performance and lifespan of the OLED.

[0006] Therefore, a compound is needed such that the organic electroluminescent element prepared from this compound can have a long service life and good current efficiency. Summary of the Invention

[0007] The object of the present invention is to provide a phenanthroline derivative, which can be used as an N-type charge generation layer material to prepare an organic electroluminescent element, and is a high-performance organic electroluminescent material.

[0008] The technical solution adopted by the present invention to solve its technical problems is:

[0009] A phenanthroline derivative, this compound has the structure shown in formula (1),

[0010] Among them,

[0011] R1, R2, R3, R4, R5, R6, and R7 are the same or different and are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and

[0012] at least one of R1, R2, R3, R4, R5, R6, and R7 is selected from substituted or unsubstituted phenanthryl;

[0013] L1 is selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;

[0014] Ar1 is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0015] When substituted in the "substituted or unsubstituted", the substituents are selected from deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 carbocyclic group, substituted or unsubstituted C3-C60 heterocyclic group;

[0016] The heteroatoms in the heterocyclic group, heteroaryl, and heteroarylene are selected from one or more combinations of N, O, S, Si, and P;

[0017] Two of R1, R2, R3, R4, R5, R6, and R7 adjacent to each other form a ring or do not form a ring;

[0018] If there are multiple substituted phenanthryl groups among R1, R2, R3, R4, R5, R6, and R7, the substituents on the multiple substituted phenanthryl groups are the same or different.

[0019] Preferably, only one of R1, R2, R3, R4, R5, R6, and R7 is selected from substituted or unsubstituted phenanthryl, and the remaining groups that are not phenanthryl are the same or different and are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0020] Further, in an optional embodiment of the present invention, the compound has the structure shown in Formula (2),

[0021]

[0022] R2, R3, R4, R5, R6, and R7 are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,

[0023] L1 is selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;

[0024] Ar1 is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0025] Preferably, L1 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted phenylnaphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fluoranthenylene, substituted or unsubstituted pyrenylene, substituted or unsubstituted perylenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridinylene, substituted or unsubstituted bipyridinylene, substituted or unsubstituted terpyridinylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted triazinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted isoquinolinylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted pyrrolylene, substituted or unsubstituted furanylene, substituted or unsubstituted thiophenylene, substituted or unsubstituted indenylene, substituted or unsubstituted indolylene, substituted or unsubstituted benzofuranylene, substituted or unsubstituted benzothiophenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted carbolinylene, substituted or unsubstituted 9,9-dimethylfluorenylene, substituted or unsubstituted 9,9-diphenylfluorenylene, substituted or unsubstituted spirobifluorenylene, substituted or unsubstituted phenanthrolinylene, substituted or unsubstituted benzoquinolinylene, substituted or unsubstituted benzoisoquinolinylene, substituted or unsubstituted imidazolylene, substituted or unsubstituted benzimidazolylene, substituted or unsubstituted oxazolylene, substituted or unsubstituted benzoxazolylene, substituted or unsubstituted thiazolylene, substituted or unsubstituted benzothiazolylene, substituted or unsubstituted pyrazolylene, substituted or unsubstituted benzopyrazolylene, substituted or unsubstituted phthalazinylene.

[0026] Preferably, L1 is selected from the following substituted or unsubstituted groups:

[0027] .

[0028] As a preference, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted indenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolinyl, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted 9,9-diphenylfluorene, substituted or unsubstituted spirobifluorene, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted benzopyrazolyl, substituted or unsubstituted phthalazinyl.

[0029] Preferably, Ar1 is selected from the following substituted or unsubstituted groups:

[0030]

[0031] Most preferably, Ar1 is selected from substituted or unsubstituted phenyl.

[0032] As a preference, R1 is selected from substituted or unsubstituted phenanthryl.

[0033] As a preference, L1 is selected from substituted or unsubstituted anthrylene.

[0034] As a preference, the phenanthroline derivative is selected from the compounds shown by the following Chemical Formulas 1 to 82:

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044] Use of a phenanthroline derivative according to the present invention as a material for an organic electroluminescent element.

[0045] The present invention also provides a preparation, which comprises a phenanthroline derivative having the structure shown above and at least one solvent.

[0046] The solvent is not particularly limited, and unsaturated hydrocarbon solvents well known to those skilled in the art such as toluene, xylene, mesitylene, tetralin, decalin, dicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc., carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane and other halogenated saturated hydrocarbon solvents, chlorobenzene, dichlorobenzene, trichlorobenzene and other halogenated unsaturated hydrocarbon solvents, tetrahydrofuran, tetrahydropyran and other ether solvents, alkyl benzoates and other ester solvents can be used.

[0047] An organic electroluminescent element, comprising a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, the organic layer comprising a light-emitting layer, the organic layer having one or more, at least one organic layer comprising a phenanthroline derivative according to the present invention.

[0048] Preferably, the organic layer comprises at least one electron transport layer, and the electron transport layer comprises the phenanthroline derivative.

[0049] Preferably, the organic layer comprises at least two light-emitting units, an N-type charge generation layer is included between the two light-emitting units, and the N-type charge generation layer of at least one light-emitting unit comprises a phenanthroline derivative according to the present invention.

[0050] Preferably, the organic layer includes at least two light-emitting units, an N-type charge generation layer is included between the two light-emitting units, the N-type charge generation layers of two or more light-emitting units include the phenanthroline derivative of the present invention, and the N-type charge generation layers of two or more light-emitting units simultaneously include the phenanthroline derivative of the present invention.

[0051] Preferably, the organic layer includes at least two light-emitting units, a P-type charge generation layer and an N-type charge generation layer are included between the two light-emitting units, and the N-type charge generation layer includes the phenanthroline derivative of the present invention; the N-type charge generation layer including the phenanthroline derivative of the present invention means that it includes one N-type charge generation layer containing the phenanthroline derivative of the present invention, or multiple N-type charge generation layers containing the phenanthroline derivative of the present invention. When two or more layers contain the phenanthroline derivative of the present invention, the phenanthroline derivatives may be the same or different.

[0052] An electronic device includes: a display device or a lighting device including the organic electroluminescent element of the present invention; and a control unit for driving the above display device or lighting device.

[0053] Compared with the existing known light-emitting materials, the beneficial effect of the present invention is that this material can be used as an N-type charge generation layer material to prepare an organic electroluminescent element, with higher current efficiency and longer service life, and it is a high-performance organic electroluminescent device. Description of the Drawings

[0054] Figure 1 It is a schematic structural diagram of the organic electroluminescent element described in Application Example 1, where there are a first electrode layer 12, a hole injection layer 11, a hole transport layer 10, a light-emitting layer 9, an electron transport layer 8, an N-type charge generation layer 7, a P-type charge generation layer 6, a hole transport layer 5, a light-emitting layer 4, an electron transport layer 3, an electron injection layer 2, and a second electrode layer 1, where 200 is the first light-emitting unit and 100 is the second light-emitting unit. Detailed Embodiments

[0055] The term "or" means "and / or". It will be further understood that when the terms "comprise" or "include" are used in this specification, it indicates the presence of the stated features, regions, wholes, steps, operations, elements, and / or components, but does not exclude the presence or addition of one or more other features, regions, wholes, steps, operations, elements, components, and / or their combinations.

[0056] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and this disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0057] As used herein, "about" or "approximately" includes the stated value and means within an acceptable deviation range for a particular value as determined by one of ordinary skill in the art in view of the measurements discussed and the errors associated with the measurement of a particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviation ranges of the stated value, or within the ranges of ±30%, 20%, 10%, 5%.

[0058] Exemplary embodiments are described herein with reference to cross-sectional views that are schematic illustrations of idealized embodiments. Thus, deviations from the shapes of the figures are to be expected as a result of, for example, manufacturing techniques and / or tolerances. Accordingly, the embodiments described herein should not be construed as limited to the specific shapes of the regions illustrated herein, but include deviations in shape resulting from, for example, manufacturing. For example, regions illustrated or described as flat may typically have rough and / or non-linear features. Additionally, sharp corners illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature, and their shapes are not intended to illustrate the exact shape of the regions and are not intended to limit the scope of the claims.

[0059] The present invention will be further described below in conjunction with specific embodiments. It should be understood that these embodiments are only for illustrating the present invention and not for limiting the protection scope of the present invention. In addition, it should be understood that after reading the content disclosed by the present invention, those skilled in the art can make various changes or modifications to the present invention, and these equivalent forms also fall within the protection scope defined by the present invention.

[0060] Unless otherwise specified, the experimental methods used in the following examples are all conventional methods; the reagents, materials, etc. used in the following examples, unless otherwise specified, can all be obtained from commercial channels.

[0061] Term Explanation

[0062] As used in the present invention, the term "halogen group" may include fluorine, chlorine, bromine or iodine.

[0063] As used in the present invention, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 10 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0064] As used in the present invention, the term "C3-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, and the like.

[0065] As used in the present invention, the term "C2-C10 heterocycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic group having 2 to 10 carbon atoms and containing at least one heteroatom selected from O, S, N, P, and Si in the ring.

[0066] As used in the present invention, the term "alkoxy" refers to a straight-chain, branched-chain, or cyclic chain. The number of carbon atoms in the alkoxy is not particularly limited herein, but the alkoxy preferably has 1 to 10 carbon atoms. Specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy (i-propyloxy), n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, and benzyloxy.

[0067] As used in the present invention, the term "cycloalkenyl" refers to an unsaturated carbocyclic ring and does not have aromaticity.

[0068] As used in the present invention, the term "heterocycloalkenyl" refers to an unsaturated heterocyclic ring and does not have aromaticity.

[0069] As used in the present invention, the term "C6-C60 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having 6 to 60 carbon atoms. Further, such an aryl may have a form in which two or more of the rings are simply linked to each other or fused to each other. Examples of such aryls include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthryl, anthryl, pyrenyl, triphenylenyl, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorenyl, and the like.

[0070] As used in the present invention, the term "arylene" refers to a divalent aryl derived by removing one hydrogen atom from "aryl". For example, removing one hydrogen atom from phenyl forms phenylene, and removing one hydrogen atom from naphthyl forms naphthylene.

[0071] As used in the present invention, the term "heteroaryl having 3 to 60 carbon atoms" refers to a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In this connection, at least one carbon, preferably 1 to 3 carbons in the ring, is replaced by a heteroatom such as N, O, S, P, B or Si. In addition, such heteroaryl can have a form in which two or more rings are simply linked to each other or fused to each other or fused to an aryl group. Examples of such heteroaryl include, but are not limited to, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolizinyl, indolyl, indolopyridyl, purinyl, phenanthrolinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furyl, thienyl, benzofuryl, benzothienyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, carbazolyl, dibenzofuryl, dibenzothienyl, etc.

[0072] As used in the present invention, the term "heteroarylene" refers to a divalent heteroaryl derived by removing one hydrogen atom from "heteroaryl", for example, pyridyl becomes pyridylene after removing one hydrogen atom.

[0073] As used in the present invention, the term "phenylnaphthylene" refers to a divalent group formed by substituting two positions in phenylnaphthalene, and these two substitution positions can be simultaneously on the benzene ring or the naphthalene ring, or one on the benzene ring and the other on the naphthalene ring.

[0074] As used in the present invention, the term "silyl" refers to a trisubstituted silyl, such as trimethylsilyl, triphenylsilyl, etc.

[0075] As used in the present invention, in the expression "Z group having X - Y carbon atoms" or "Z group of C(X - Y)", "having X - Y carbon atoms" means the number of carbon atoms of the Z group when it is unsubstituted, excluding the carbon atoms of the substituents when it is substituted. For example, an aryl group having 6 to 60 carbon atoms means that when unsubstituted, the number of carbon atoms in the aryl group is any integer from 6 to 60, that is, when unsubstituted, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20... 60.

[0076] As used in the present invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position where substitution occurs can be the position where the hydrogen atom is replaced. That is, this position is not limited to a specific position, as long as the hydrogen at this position can be replaced by a substituent. For example, if not otherwise specified in this specification, carbazolyl includes any of the following groups, but is not limited thereto,

[0077] Indicates the substitution position. "Unsubstituted" means retaining a hydrogen atom, in which case the hydrogen atom includes protium, deuterium, and tritium.

[0078] When two or more substituents are present, the two or more substituents may be the same or different.

[0079] As used in the present invention, the term "quinoline" includes 1,2-quinoline, 1,3-quinoline, 1,4-quinoline, 1,5-quinoline, 1,6-quinoline, 1,7-quinoline, 1,8-quinoline, 2,3-quinoline, 2,4-quinoline...

[0080] As used in the present invention, the term "terphenyl" includes

[0081] As used in the present invention, the term "benzoquinoline" includes

[0082] As used in the present invention, the hydrogen atom includes protium, deuterium, and tritium. The compounds described in the present invention may contain deuterium atoms of natural origin, or deuterium atoms may be introduced by deuterating part or all of the starting compounds. If deuterium atoms are introduced from the starting materials, the deuteration rate may be 100%, or less than 100%, or less than 95%, or less than 90%, or less than 80%. The deuteration rate may also be 1% or more, or 5% or more, or 10% or more. If the deuteration rate is not 100%, it means a mixture of deuterated compounds and non-deuterated compounds, or a mixture of fully deuterated compounds and incompletely deuterated compounds, or a mixture of fully deuterated compounds, non-deuterated compounds, and incompletely deuterated compounds.

[0083] As used in the present invention, when "substituted or unsubstituted", the substituents for substitution are selected from the group consisting of deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 carbocyclic group, substituted or unsubstituted C3-C60 heterocyclic group; Exemplarily, the substituents for substitution include: substituted or unsubstituted phenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted indenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolinyl, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted 9,9-diphenylfluorene, substituted or unsubstituted spirobifluorene, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted benzopyrazolyl, substituted or unsubstituted phthalazinyl.

[0084] As used in the present invention, terms such as the first, the second, A, B, etc. are used. The above terms are only used to distinguish the constituent elements and do not limit the essence or order of the constituent elements corresponding to the terms.

[0085] Organic electroluminescent element

[0086] The structure of the organic electroluminescent element of the present invention is a publicly known structure, including an anode, a cathode, and an organic layer located between the anode and the cathode. The organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the compound of the present invention.

[0087] The organic layer may further include one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.

[0088] The light-emitting element of the present invention can be fluorescent emission, phosphorescent emission, or a combination thereof. The light-emitting element can be a single light-emitting element or a series type of multiple light-emitting units.

[0089] As a simple light-emitting element, the following can be cited, but are not limited thereto.

[0090] (1) Hole transport layer / fluorescent light-emitting layer / electron transport layer;

[0091] (2) Hole transport layer / phosphorescent light-emitting layer / electron transport layer;

[0092] (3) Hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;

[0093] (4) Hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer / electron transport layer;

[0094] (5) Hole transport layer / fluorescent light-emitting layer / spacer layer / phosphorescent light-emitting layer / electron transport layer;

[0095] (6) Hole transport layer / electron blocking layer / fluorescent light-emitting layer / electron transport layer;

[0096] (7) Hole transport layer / electron blocking layer / fluorescent light-emitting layer / hole blocking layer / electron transport layer;

[0097] (8) Hole transport layer / electron blocking layer / phosphorescent light-emitting layer / electron transport layer;

[0098] (9) Hole transport layer / electron blocking layer / phosphorescent light-emitting layer / hole blocking layer / electron transport layer;

[0099] (10) Hole injection layer / hole transport layer / phosphorescent light-emitting layer / electron transport layer / electron injection layer;

[0100] (11) Hole injection layer / hole transport layer / fluorescent light-emitting layer / electron transport layer / electron injection layer;

[0101] (12) Hole injection layer / hole transport layer / electron blocking layer / phosphorescent light-emitting layer / electron transport layer / electron injection layer;

[0102] (13) Hole injection layer / hole transport layer / electron blocking layer / fluorescent light-emitting layer / electron transport layer / electron injection layer;

[0103] The above-mentioned phosphorescent / fluorescent light-emitting layers can each emit light of different colors.

[0104] As a tandem organic electroluminescent element, it can be an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode. The intermediate layer is generally also called a charge generation layer, an electron extraction layer, a connection layer, etc. For example, when stacking a fluorescent light-emitting layer and a phosphorescent light-emitting layer, in order to prevent the excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer, or to adjust the carrier balance, an intermediate layer is placed between the fluorescent light-emitting layer and the phosphorescent light-emitting layer.

[0105] When the organic light-emitting device includes a plurality of organic layers, the organic layers can be formed of the same material or different materials.

[0106] The organic electroluminescent element of the present specification can be manufactured by materials and methods known in the art, except that one or more of the organic layers are formed by using a compound containing formula (1).

[0107] The organic electronic element of the present invention includes a substrate, an anode, a cathode, and an organic layer provided between the cathode and the anode.

[0108] The substrate serves as a support for the light-emitting element. As the substrate, for example, glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can also be used. A flexible substrate refers to a substrate that can be bent (flexible), such as a plastic substrate formed of polycarbonate or polyvinyl chloride. The available substrates in the embodiments of the present invention are not limited thereto, as long as they can support the light-emitting element.

[0109] The anode formed on the substrate preferably uses a metal, alloy, conductive compound, and a mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium containing tungsten oxide and zinc oxide, graphene, etc. In addition, gold (Au), platinum (Pt), or a nitride of a metal material (for example, titanium nitride) can also be used. The available anode materials in the embodiments of the present invention are not limited thereto, and other anode materials can also be used in the embodiments of the present invention.

[0110] The cathode preferably uses a metal, alloy, conductive compound, or a mixture thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), and alloys containing them (e.g., MgAg, AlLi), etc. The available cathode materials in the embodiments of the present invention are not limited to this, and other cathode materials can also be used in the embodiments of the present invention.

[0111] As the cathode material, a material with a low work function is usually used to facilitate electron injection into the organic layer.

[0112] The hole injection layer is a layer that injects holes from the electrode and has the ability to transport holes. As substances with high hole injection properties, ladder compounds or polymer compounds (oligomers, dendrimers, polymers, etc.) such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, fluorene derivatives, etc. can also be selected. The available hole injection layer materials in the embodiments of the present invention are not limited to this, and other hole injection layer materials can also be used in the embodiments of the present invention.

[0113] The hole transport material is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material can appropriately be a material with a high hole mobility that receives holes from the anode or the hole injection layer and transfers the holes to the light-emitting layer. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used in the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), etc. can also be used. Among them, as long as the hole transport property is higher than the electron transport property, substances other than the above can be used. It should be noted that the layer containing a substance with high hole transport property can be not only a single-layered layer but also a layer formed by laminating two or more layers containing the above substances. The available hole transport materials in the embodiments of the present invention are not limited to this, and other hole transport materials can also be used in the embodiments of the present invention.

[0114] The light-emitting material is a material that can respectively receive holes and electrons from the hole transport layer and the electron transport layer and combine the holes and electrons to emit light in the visible light region. The light-emitting layer material contains a host material and a doping material.

[0115] The light-emitting layer preferably contains a host material (sometimes called a matrix material) and a doping material (sometimes called a light-emitting material, guest material, or emitter). The embodiments of the present invention use well-known host materials, such as amine derivatives, azine derivatives, and fused polycyclic aromatic derivatives, etc.

[0116] Amine derivatives, such as monoamine compounds, diamine compounds, triamine compounds, tetraamine compounds, and amine compounds substituted with a carbazolyl group, etc.

[0117] Azine derivatives, such as monoazine derivatives, diazine derivatives, and triazine derivatives, etc.

[0118] Fused polycyclic aromatic derivatives, preferably fused polycyclic aromatic hydrocarbons without a heterocyclic skeleton, such as: fused polycyclic aromatic hydrocarbons such as naphthalene, anthracene, phenanthrene, fluoranthene, and triphenylene, or their derivatives.

[0119] The host material can be used alone or in combination of two or more.

[0120] The light-emitting layer can contain only one kind of host material or can contain two or more host materials.

[0121] The content of the host material is not particularly limited. The content of the host material is, for example, preferably 80% by mass or more and 99.9% by mass or less, more preferably 90% by mass or more and 99.9% by mass or less, and still more preferably 95% by mass or more and 99.9% by mass or less, relative to the entire light-emitting layer.

[0122] The light-emitting layer contains a dopant material. The dopant material is preferably a substance with high luminescence, and various materials can be used.

[0123] For example, as the dopant material, a fluorescent luminescent material that emits fluorescence and a phosphorescent luminescent material that emits phosphorescence can be used. The fluorescent luminescent material is a compound capable of emitting light from a singlet excited state, and the phosphorescent luminescent material is a compound capable of emitting light from a triplet excited state.

[0124] As the fluorescent host, a compound having a singlet energy level higher than that of the fluorescent dopant is preferred, and examples thereof include phenanthroline derivatives and fused aromatic compounds.

[0125] As the phosphorescent host, a compound having a triplet energy level higher than that of the phosphorescent dopant is preferred. For example, metal complexes, phenanthroline derivatives, fused aromatic compounds, etc. can be cited. Among them, for example, indole derivatives, carbazole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, naphthalene derivatives, triphenylene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc. are preferred.

[0126] An electron transport material is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material can receive electrons from the cathode and transfer the electrons to the light-emitting layer and has a high electron mobility. Preferably having 10 -6 cm2 Substances with an electron mobility of more than / Vs include, for example, metal complexes, phenanthroline derivatives, aromatic hydrocarbon compounds, polymer compounds, etc.

[0127] As long as the compound has a higher electron transport property than a hole transport property, substances other than these can be used for the electron transport layer.

[0128] The electron transport layer can be a single layer or can be laminated with two or more layers. In this case, it is preferable to dispose a layer containing a substance with a larger energy gap among substances with high electron transport properties closer to the light-emitting layer side.

[0129] The electron transport layer may contain, for example, metals such as alkali metals, magnesium, alkaline earth metals, alloys containing two or more of them; metal compounds such as alkali metal compounds such as lithium 8-quinolinolate (abbreviation: Liq), alkaline earth metal compounds. When metals such as alkali metals, magnesium, alkaline earth metals, or alloys containing two or more of them are contained in the electron transport layer, their content is not particularly limited, and it is preferably 0.1 to 50% by mass, more preferably 0.1 to 20% by mass, and further preferably 1 to 10% by mass.

[0130] When metal compounds such as alkali metal compounds or alkaline earth metal compounds are contained in the electron transport layer, their content is preferably 1 to 99% by mass, more preferably 10 to 90% by mass. It should be noted that the layer on the light-emitting layer side when the electron transport layer is multilayered can also be formed only of these metal compounds. The electron injection layer is a layer that injects electrons from the electrode. For the electron injection layer, alkali metals, alkaline earth metals, or their compounds such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx) can be used. In addition, materials in which a substance having an electron transport property contains an alkali metal, an alkaline earth metal, or their compounds can also be used for the electron injection layer. Specifically, materials in which magnesium (Mg) is contained in Alq can be used. It should be noted that, in this case, electron injection from the cathode can be performed more efficiently.

[0131] Alternatively, a composite material formed by mixing an organic compound and an electron donor (donor) can also be used for the electron injection layer. Such a composite material generates electrons in the organic compound due to the electron donor, and thus has excellent electron injection properties and electron transport properties. At this time, as the organic compound, a material with excellent electron transport of the generated electrons is preferably used. Specifically, for example, the substances constituting the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. As the electron donor, any substance that exhibits electron-donating properties to the organic compound can be used. Specifically, as the electron donor, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. In addition, as the electron donor, alkali metal oxides and alkaline earth metal oxides are preferred, and examples include lithium oxide, calcium oxide, and barium oxide. In addition, a Lewis base such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[0132] The hole blocking layer is a layer that blocks holes from reaching the cathode.

[0133] The electron blocking layer is a layer that blocks electrons from reaching the anode.

[0134] Depending on the materials used, the organic light-emitting device of this specification can be a top-emitting device, a bottom-emitting device, or a dual-emission device.

[0135] The charge generation layer refers to an intermediate layer located between the anode and the cathode in a tandem structure device, and is a layer that generates holes and electrons by charge separation. The charge generation layer is usually formed by a P-type layer on the cathode side and an N-type layer on the anode side, and can effectively separate charges and efficiently transport carriers.

[0136] In one embodiment of the present invention, the formation method of each layer is not particularly limited. Formation methods based on vacuum evaporation, spin coating, etc. that are well known in the art can be used. Each layer such as the light-emitting layer can be formed by a well-known method such as vacuum evaporation, molecular beam epitaxy (MBE method), or a coating method such as dip coating, spin coating, casting, bar coating, or roll coating of a solution dissolved in a solvent.

[0137] In one embodiment of the present invention, the film thickness of each layer is not particularly limited, and generally several nanometers to dozens of nanometers can be used. In order to suppress defects such as pinholes, reduce the driving voltage, and improve the light-emitting efficiency, a range of several nm to 1 μm is usually preferred. Those skilled in the art can synthesize the compounds of the present invention with reference to the synthesis of the following compounds and well-known synthesis methods.

[0138] Synthesis Examples

[0139] Example 1: Synthesis of Compound 1

[0140] Step 1: Synthesis of Intermediate 1

[0141]

[0142] Under a nitrogen atmosphere, 2-chloro-9-bromo-1,10-phenanthroline (10 g, 34.06 mmol), 9-phenanthreneboronic acid (7.2 g, 32.36 mmol), 150 ml of tetrahydrofuran, 50 ml of water, potassium carbonate (9.4 g, 68.12 mmol), and tetrakis(triphenylphosphine)palladium (790 mg, 0.68 mmol) were successively added to a 500 ml four-necked flask, and the mixture was refluxed for 2 hours. After the reaction was completed, water was separated, and the product was separated by silica gel column chromatography (volume ratio: n-hexane:dichloromethane = 1:1) to obtain 2-chloro-9-(phenanthren-9-yl)-1,10-phenanthroline (11 g, 28.1 mmol).

[0143] LC-MS (APCI): 391.11 [M+H] +

[0144] Step 2: Synthesis of Compound 1

[0145]

[0146] 2-chloro-9-(phenanthren-9-yl)-1,10-phenanthroline

[0147] Under a nitrogen atmosphere, 2-chloro-9-(phenanthren-9-yl)-1,10-phenanthroline (11 g, 28.1 mmol), (10-phenylanthracen-9-yl)boronic acid (8.8 g, 29.5 mmol), 150 ml of tetrahydrofuran, 50 ml of water, potassium carbonate (7.8 g, 56.2 mmol), and tetrakis(triphenylphosphine)palladium (650 mg, 0.56 mmol) were successively added to a 500 ml single-necked flask, and the mixture was refluxed for 2 hours. After the reaction was completed, water was separated, and the product was separated by silica gel column chromatography (n-hexane:dichloromethane = 3:2) to obtain 2-(phenanthren-9-yl)-9-(10-phenylanthracen-9-yl)-1,10-phenanthroline (16 g, 26.3 mmol).

[0148] LC-MS (APCI): 609.54 [M+H] +

[0149] 1 1H NMR (400 MHz, CD2Cl2) δ 8.67 - 8.57 (m, 2H), 8.48 (d, 1H), 8.40 (d, 1H), 8.07 (dd, 1H), 8.04 - 7.94 (m, 2H), 7.93 - 7.87 (m, 2H), 7.87 - 7.77 (m, 2H), 7.62 - 7.18 (m, 17H).

[0150] The following application examples further illustrate the application of the nitrogen-containing fused-ring compound described in the present invention in the preparation of organic electroluminescent devices.

[0151] Application Example 1:

[0152] This embodiment provides an organic electroluminescent device, as Figure 1 shown, including a first electrode layer 12, a hole injection layer 11, a hole transport layer 10, a light-emitting layer 9, an electron transport layer 8, an N-type charge generation layer 7, a P-type charge generation layer 6, a hole transport layer 5, a light-emitting layer 4, an electron transport layer 3, an electron injection layer 2, and a second electrode layer 1 which are stacked. Among them, 200 is the first light-emitting unit and 100 is the second light-emitting unit. The first light-emitting unit 200 includes a hole injection layer 11, a hole transport layer 10, a light-emitting layer 9, and an electron transport layer 8. The second light-emitting unit 100 includes a hole transport layer 5, a light-emitting layer 4, an electron transport layer 3, and an electron injection layer 2.

[0153] The specific device structure is:

[0154] ITO(100nm) / NPD:F4-TCNQ(10%)(10nm) / NPD(120nm) / BH:BD(3%)(20nm) / TmPyPB(10nm) / Bphcn:Li(2%)(10nm) / NPD:F4-TCNQ(10%)(20nm) / NPD(20nm) / BH:BD(3%)(20nm) / Alq3(10nm) / LiF(0.5nm) / Al(200nm).

[0155] Device preparation process:

[0156] The bottom-emitting glass substrate used in this embodiment is purchased from Guangdong Xinke Display Technology Co., Ltd., and 100 nm ITO is used as the first electrode layer 12. First, the bottom-emitting glass substrate is successively cleaned with ITO cleaning agent, deionized water, and isopropyl alcohol, and then baked at 180 degrees Celsius for 30 minutes to dry it.

[0157] Then the bottom-emitting glass substrate is placed in the evaporation chamber, and the vacuum degree is about 10 -8In the case of a carrier, each organic layer was sequentially deposited on the ITO anode by thermal vacuum evaporation at a rate of 0.2 - 2 Å / sec. Among them, F4-TCNQ (mass content 10%) was incorporated into NPD to form a thickness of 10 nm as the hole injection layer. NPD was formed to a thickness of 120 nm as the hole transport layer. On the anthracene host ADN (9,10-di(naphtha-2-yl-)anthracene), a pyrene dopant 1,6-bis(diphenylamino)pyrene with a mass content of 3% was doped to form a blue light-emitting layer with a thickness of 20 nm. TmPyPB was formed to a thickness of 10 nm as the first electron transport layer. In BPhen (4,7-Diphenyl-1,10-phenanthroline), Li with a mass content of 2% was doped to form an N-type charge generation layer 7 with a thickness of 10 nm. On NPD, F4-TCNQ with a mass content of 10% was doped to form a P-type charge generation layer with a thickness of 20 nm. NPD was formed to a thickness of 20 nm as the hole transport layer. On the anthracene host ADN (9,10-di(naphtha-2-yl-)anthracene), a pyrene dopant 1,6-bis(diphenylamino)pyrene with a mass content of 3% was doped to form a blue light-emitting layer with a thickness of 20 nm. Alq3 (Tris-(8-hydroxyquinolinato)aluminum) was formed to a thickness of 10 nm as the second electron transport layer. LiF was formed to a thickness of 0.5 nm as the electron injection layer. Al was formed to a thickness of 200 nm as the cathode.

[0158] Finally, the device was transferred back to the glove box and encapsulated with a glass cover and a desiccant to complete the device, denoted as organic electronic component 1.

[0159]

[0160]

[0161] Comparative structure

[0162] Bphen (4,7-Diphenyl-1,10-phenanthroline)

[0163]

[0164] Examples and comparative examples

[0165] Compound 1 prepared in Example 1 of the present invention was used to replace the Bphen material to prepare the N-type charge generation layer 7, and the organic electronic component 2 was fabricated by the same method.

[0166] Evaluation of Organic Electroluminescent Element

[0167] Lifetime test method: Apply a voltage to the obtained organic electroluminescent element so that the current density reaches 30 mA / cm 2 , and measure the time (LT95 (unit: hour)) until the luminance becomes 95% of the initial luminance.

[0168] The current efficiency is tested at a current density of 15 mA / cm 2 .

[0169] The driving voltage is tested at a current density of 15 mA / cm 2 . The test results are shown in Table 1.

[0170] Table 1

[0171] Driving voltage, V Current efficiency, cd / A LT95, h Organic electronic component 1 7.07 17.53 58 Organic electronic component 2 6.90 17.68 92

[0172] According to the data in Table 1, it can be seen that the organic electroluminescent element 2 prepared from the compound of the present application and the organic electronic element 1 have lower driving voltage, higher current efficiency and longer service life. Therefore, the compound of the present invention is suitable for preparing high-performance organic electroluminescent elements.

[0173] It is easy for those skilled in the art to understand that the above are only the preferred embodiments of the present invention and are not used to limit the present invention. Any modifications, equivalent replacements and improvements made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.

Claims

1. A phenanthroline derivative, characterized in that, The compound has the structure shown in formula (1), Among them, R1, R2, R3, R4, R5, R6, and R7 are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and at least one of R1, R2, R3, R4, R5, R6, and R7 is selected from substituted or unsubstituted phenanthryl; L1 is selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene; Ar1 is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; the substituents in the "substituted or unsubstituted" are selected from deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 carbocyclic group, substituted or unsubstituted C3-C60 heterocyclic group; the heteroatoms in the heterocyclic group, heteroaryl, and heteroarylene are selected from one or more combinations of N, O, S, Si, and P; two adjacent ones of R1, R2, R3, R4, R5, R6, and R7 form a ring or do not form a ring; if there are multiple substituted phenanthryl groups among R1, R2, R3, R4, R5, R6, and R7, the substituents on the multiple substituted phenanthryl groups are the same or different.

2. A phenanthroline derivative according to claim 1, wherein only one of R1, R2, R3, R4, R5, R6, and R7 is selected from substituted or unsubstituted phenanthryl, and the remaining groups R1, R2, R3, R4, R5, R6, and R7 that are not phenanthryl are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

3. A phenanthroline derivative according to claim 1, wherein The compound has the structure shown in formula (2), R2, R3, R4, R5, R6, and R7 are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, L1 is selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene; Ar1 is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

4. A phenanthroline derivative according to claim 1, wherein L1 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fluoranthenylene, substituted or unsubstituted pyrenylene, substituted or unsubstituted perylenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridine, substituted or unsubstituted bipyridine, substituted or unsubstituted terpyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridazine, substituted or unsubstituted pyrazine, substituted or unsubstituted triazine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted pyrrole, substituted or unsubstituted furan, substituted or unsubstituted thiophene, substituted or unsubstituted indene, substituted or unsubstituted indole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazole, substituted or unsubstituted carboline, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted oxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted thiazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted pyrazole, substituted or unsubstituted benzopyrazole, substituted or unsubstituted phthalazine.

5. A phenanthroline derivative according to claim 1, characterized in that, L1 is selected from the following substituted or unsubstituted groups:

6. A phenanthroline derivative according to claim 1, wherein Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted indenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolinyl, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted 9,9-diphenylfluorene, substituted or unsubstituted spirobifluorene, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted benzopyrazolyl, substituted or unsubstituted phthalazinyl.

7. A phenanthroline derivative according to claim 1, characterized in that, Ar1 is selected from the following substituted or unsubstituted groups:

8. A phenanthroline derivative according to claim 1, characterized in that, The phenanthroline derivative is selected from the compounds represented by the following Chemical Formulas 1 to 82:

9. An organic electroluminescent element, comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer including a light-emitting layer, characterized in that: The organic layer has one or more, and at least one organic layer contains the phenanthroline derivative according to any one of claims 1 to 8.

10. An electronic device, comprising: One or more of a display, a monitor, and a lighting device, including the organic electroluminescent element according to claim 9; And a control unit for driving the above display device.

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