Condensed ring compound, organic electroluminescent device and electronic equipment

Abstract

The invention relates to the technical field of organic photoelectric materials, in particular to a fused ring compound and an organic electroluminescent device using the same. Two main ring structures with large steric hindrance are connected through amido, so that the plane configuration is distorted, the distance between molecules is increased, and the adverse effect of the concentration quenching effect on the efficiency is weakened. When the fused ring compound is used as a light-emitting material in an OLED device, especially as a blue light doping material, the device can show excellent performance and stability, the driving voltage can be reduced, the light-emitting efficiency can be improved, and the service life of the device can be prolonged. And the requirements of current panel manufacturing enterprises on high-performance materials can be met, and good commercial application prospects are achieved.

Description

Technical Field

[0001] The present invention relates to the technical field of organic photoelectric materials, and in particular to a condensed ring compound, an organic electroluminescent device and an electronic device. Background Art

[0002] With the development of multimedia technology and the improvement of information requirements, the requirements for panel display performance are getting higher and higher. Among them, OLED has a series of advantages such as autonomous luminescence, low-voltage DC drive, full curing, wide viewing angle, rich colors, etc. It has attracted widespread attention for its potential application in the new generation of display and lighting technology, and its application prospects are very broad. Organic electroluminescent devices are spontaneous light-emitting devices. The mechanism of OLED light emission is that under the action of an external electric field, electrons and holes are injected from the positive and negative electrodes respectively, migrate, recombine and decay in the organic material to produce light. The typical structure of OLED includes one or more functional layers such as cathode layer, anode layer, electron injection layer, electron transport layer, hole blocking layer, hole transport layer, hole injection layer and organic light-emitting layer.

[0003] Although the research progress of organic electroluminescence is very rapid, there are still many problems to be solved, such as the improvement of external quantum efficiency (EQE), the design and synthesis of new materials with higher color purity, the design and synthesis of new materials with high efficiency electron transport / hole blocking, etc. For organic electroluminescent devices, the luminescence quantum efficiency of the device is a comprehensive reflection of various factors and is also an important indicator to measure the quality of the device.

[0004] Luminescence can be divided into fluorescence and phosphorescence. In fluorescence, organic molecules in a singlet excited state transition to a ground state, thereby emitting light. On the other hand, in phosphorescence, organic molecules in a triplet excited state transition to a ground state, thereby emitting light.

[0005] At present, some organic electroluminescent materials have been used commercially due to their excellent performance. However, as the host material in the organic electroluminescent device, in addition to the triplet energy level being higher than that of the guest material to prevent the reverse transfer of energy released by the exciton transition, it is more important to have good hole migration performance. At present, there is still a lack of materials with both high triplet energy levels and good hole mobility in the host material. Therefore, how to design new host materials with better performance has always been a problem that needs to be solved urgently by those skilled in the art. Summary of the invention

[0006] In view of the shortcomings of the prior art, the object of the present invention is to provide a condensed ring compound, an organic electroluminescent device and an electronic device. The present invention improves hole mobility, hole transport and luminescence effects through a specific compound. The compound is prepared into a device with good luminescence efficiency and high commercial application prospects.

[0007] To achieve the above technical objectives, the technical solution of the present invention is as follows:

[0008] The present invention provides a condensed ring compound having a general structure as shown in Formula I:

[0009]

[0010] In Formula I, m and n are selected from integers between 0 and 3, and when m is 0, Q 1 Directly connected to N; when n is 0, Q 2 Directly connected to N;

[0011] L is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl;

[0012] R 1 -R 2 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 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heterocycloalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl;

[0013] Q1 and Q2 are the same or different and are independently selected from the structure shown in formula (1):

[0014]

[0015] In formula (1), X 1 , X 2 The same or different, each independently selected from O, NR 10 , multiple R 10 When present, multiple R 10 Each is independent, identical or different from the other;

[0016] R 7 -R 9 wherein one of them is the connection position between Formula I and Formula (1), and the others 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 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heterocycloalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl;

[0017] R 3 -R 6 , R 10 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 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heterocycloalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl;

[0018] Formula (2) or formula (3) is fused with formula (1) at the U or V position;

[0019]

[0020] In the above formula, Y is selected from O and S;

[0021] R 11 -R 14 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 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heterocycloalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl;

[0022] The substituents in the "substituted or unsubstituted" are each independently selected from deuterium, halogen, cyano, silane, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, C3-C30 heteroaryl,

[0023] The heteroatoms in the heteroarylene group, heterocycloalkyl group, heterocycloalkenyl group and heteroaryl group are each independently at least one of N, O, S, Si and P.

[0024] Furthermore, Q1 and Q2 are the same or different and are independently selected from the structures shown in Formula II-1 to Formula II-7:

[0025]

[0026] In the above formula, R 3 -R 7 , R 9 -R 14are 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 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heterocycloalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl.

[0027] Further, L is selected from the following trivalent groups: phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthene, pyrene, peryl, triphenylene, pyridyl, bipyridyl, terpyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, pyrrolyl, furanyl, thienyl, indenyl, indolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, carbolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, phenanthroline, benzoquinolyl, benzisoquinolyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, pyrazolyl, benzopyrazolyl, naphthyridine.

[0028] More preferably, L is selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, dibenzofuranyl, dibenzothienyl, terpyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl and a combination of two or more of the above groups.

[0029] Furthermore, the R 1 -R 2the same or different, each independently selected from hydrogen, deuterium, halogen, cyano, 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 peryl, substituted or unsubstituted triphenylene, 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 quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted indenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted substituted or unsubstituted phenanthroline, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted benzisoquinolyl, 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 naphthyridinyl.

[0030] More preferably, R 1 -R 2 The same or different, each independently selected from hydrogen, phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, carbolyl, benzoquinolyl, benzopyrazolyl, benzimidazolyl and a combination of two or more of the above groups.

[0031] Furthermore, the R 3 -R 7 , R 9 , R 11 -R 14 The same or different, each independently selected from the following groups: hydrogen, deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, pyrene, perylenyl, triphenylene, indenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl and combinations of two or more of the above groups, for example, tert-butyl substituted phenyl, etc.

[0032] Furthermore, the R 10 Any one selected from phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, pyrenyl, perylenyl, triphenylene, and deuterated, halogenated or tert-butyl substituted groups.

[0033] Furthermore, the condensed ring compound is selected from the following chemical structures:

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040] .

[0041] The present invention also provides an organic electroluminescent device, which comprises a first electrode, a second electrode and at least one organic functional layer arranged between the first electrode and the second electrode, wherein the at least one organic functional layer comprises the condensed ring compound.

[0042] Furthermore, the organic functional layer includes a hole injection layer, an electron transport layer, an electron blocking layer, a functional layer having both hole injection and hole transport functions, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a functional layer having both electron injection and electron transport functions. At least one of the hole injection layer, electron transport layer, electron blocking layer, a functional layer having both hole injection and hole transport functions, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a functional layer having both electron injection and electron transport functions contains the condensed ring compound.

[0043] The present invention also provides a preparation, which comprises a condensed ring compound having the structure shown above or the composition as described above and at least one solvent.

[0044] The solvent is not particularly limited and may be used, for example, unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, butyl chloride, butyl bromide, pentyl chloride, pentyl bromide, hexyl chloride, hexyl bromide, cyclohexyl chloride, cyclohexyl bromide, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, ether solvents such as tetrahydrofuran, tetrahydropyran, and ester solvents such as alkyl benzoate.

[0045] The present invention further provides an electronic device, which includes a display or lighting device, wherein the device includes one or more of the organic electroluminescent devices described above.

[0046] Compared with the prior art, the present invention has the following beneficial effects:

[0047] The present invention connects two main ring structures with large steric hindrance through an amine group, changes its planar configuration, and increases the distance between molecules, thereby reducing the adverse effect of concentration quenching effect on efficiency. When the condensed ring compound of the present invention is used as a light-emitting material in an OLED device, especially as a blue light doping material, the device can exhibit excellent performance and stability, reduce the driving voltage, improve the luminous efficiency, and increase the service life of the device. It can meet the requirements of current panel manufacturers for high-performance materials and has good commercial application prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0048] Figure 1 This is a schematic diagram of the device structure of an organic electroluminescent element according to an embodiment of the present invention, wherein the first electrode layer 1, the hole injection layer 2, the hole transport layer 3, the luminescence auxiliary layer 4, the luminescent layer 5, the electron transport layer 6, the electron injection layer 7 and the second electrode layer 8. DETAILED DESCRIPTION

[0049] The contents of the present invention will be described in detail below. The description of the constituent elements described below may be based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples.

[0050] As used in the present invention, the term "halogen group" may include fluorine, chlorine, bromine or iodine.

[0051] As used in the present invention, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 10 carbon atoms, examples of which include but are not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl.

[0052] 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 cycloalkyl include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, adamantane, and the like.

[0053] As used in the present invention, the term "C2-C10 heterocyclic group (heterocycloalkyl)" refers to a monovalent substituent derived from a monocyclic or polycyclic ring having 2 to 10 carbon atoms, and the ring contains at least one heteroatom selected from O, S, N, P, Si.

[0054] As used in the present invention, the term "alkoxy" refers to a straight chain, a branched chain or a cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited herein, but the alkoxy group 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-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, and benzyloxy.

[0055] As used herein, the term "cycloalkenyl" refers to an unsaturated carbon ring and does not have aromatic character.

[0056] As used herein, the term "heterocycloalkenyl" refers to an unsaturated heterocyclic ring, and does not have aromaticity.

[0057] As used in the present invention, the term "C6-C60 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a monocyclic 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 rings are simply lateral or fused to each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, pyrenyl, triphenylene, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorenyl, etc.

[0058] As used herein, the term "arylene group" refers to a divalent aromatic group derived from an "aryl group" by removing a hydrogen atom. For example, a phenyl group is substituted by removing a hydrogen atom to form a phenylene group, and a naphthyl group is substituted by removing a hydrogen atom to form a naphthylene group.

[0059] As used in the present invention, the term "C3-C60 heteroaryl group" refers to a monovalent substituent derived from a monocyclic heterocyclic 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 are substituted with a heteroatom such as N, O, S, P, B or Si. In addition, this heteroaryl group may have a form in which two or more rings are simply lateral to each other or fused to each other or fused to an aromatic group. Examples of such heteroaryl groups include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolizinyl, indolyl, indolopyridinyl, purinyl, phenanthroline, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, carbazolyl, dibenzofuranyl, dibenzothienyl and the like, but the present invention is not limited thereto.

[0060] As used in the present invention, the term "heteroarylene" refers to a divalent heteroaryl group derived from a "heteroaryl" by removing a hydrogen atom. For example, a pyridyl group is derived from a pyridylene group by removing a hydrogen atom.

[0061] As used in the present invention, the term "silyl group" refers to a trisubstituted silyl group, such as trimethylsilyl, triphenylsilyl, and the like.

[0062] As used in the present invention, the "carbon number is XY" in the expression "Z group having carbon number XY" or "Z group of C(XY)" means the carbon number of the Z group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. For example, a C6-C60 aromatic group means that when it is unsubstituted, the carbon number of the aromatic group is any integer between 6 and 60, that is, the carbon number when unsubstituted can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20...60.

[0063] 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 the substitution occurs may be the position where the hydrogen atom is replaced. That is, the position is not limited to a specific position, as long as the hydrogen at the position can be replaced by a substituent, and the substitution may be deuterated. For example, carbazolyl includes any of the following groups, but is not limited thereto, as long as it is not otherwise described in this specification,

[0064]

[0065] Indicates the position of substitution. "Unsubstituted" means that hydrogen atoms remain, in this case, hydrogen atoms include protium, deuterium, tritium.

[0066] When two or more substituents are present, the two or more substituents may be the same or different.

[0067] As used herein, the term "naphthyridine" includes

[0068] As used herein, the term "terphenyl" includes

[0069] As used herein, the term "benzoquinoline" includes

[0070] As used in the present invention, hydrogen atoms include protium, deuterium and tritium. The compounds of the present invention may contain deuterium atoms of natural origin, or may introduce deuterium atoms by deuterating a portion or all of the raw material compounds. If deuterium atoms are introduced from the raw materials, the deuteration rate may be 100%, or may be less than 100%, or less than 95%, or less than 90%, or less than 80%, and the deuteration rate may also be more than 1%, or more than 5%, or more than 10%. If the deuteration rate is not 100%, it means a mixture of deuterated compounds and undeuterated compounds, or a mixture of completely deuterated compounds and incompletely deuterated compounds, or a mixture of completely deuterated compounds and undeuterated compounds and incompletely deuterated compounds.

[0071] As used in the present invention, terms such as first, second, A, B, etc. are used. The above terms are only used to distinguish components, and do not limit the nature or order of the components to which the terms correspond.

[0072] The compounds disclosed herein can exhibit desirable properties and have emission and / or absorption spectra that can be tuned by selecting appropriate ligands. In another aspect, the invention can exclude any one or more compounds, structures or portions thereof specifically recited herein.

[0073] The compounds of the present invention may be prepared using a variety of methods, including but not limited to those described in the examples provided herein.

[0074] It should be noted that the above general description and the following detailed description are only exemplary and explanatory, and are not limiting. The present application can be more easily understood by referring to the following specific implementation manner and the examples contained therein.

[0075] Before disclosing and describing the compounds, devices and / or methods of the present invention, it should be understood that they are not limited to specific synthetic methods (otherwise otherwise indicated), or specific reagents (otherwise otherwise indicated), as this can of course vary. It should also be understood that the terms used in the present invention are only used for the purpose of describing specific aspects and are not intended to be limiting. Although any methods and materials similar or equivalent to those described in the present invention can be used in the practice or test, exemplary methods and materials are described below. Synthesis Examples All raw materials and solvents are commercially available unless otherwise specified, and solvents are used directly without further treatment.

[0076] The substrate of the present invention can be any substrate used in typical organic optoelectronic devices. It can be a glass or transparent plastic substrate, or a substrate of an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, the use direction is different. As the material for the hole injection layer, the hole transport layer, and the electron injection layer, any material can be selected from the known related materials for OLED devices, and the present invention does not make specific restrictions thereon.

[0077] Those skilled in the art can synthesize the compounds of the present invention by referring to the synthesis of the following compounds and known synthesis methods.

[0078] Synthesis of intermediates:

[0079] 1. Synthesis of Intermediate 2-1

[0080]

[0081] Step 1. Under nitrogen conditions, add 2-bromo-5-chloro-1,3-difluorobenzene (12.5g, 55.0mmol), 4-(tert-butyl)phenol (17.27g, 115mmol), potassium carbonate (16.6g, 120mmol) and N-methylpyrrolidone (250ml), stir and reflux for 9 hours, cool at room temperature, separate the organic layer with chloroform and water, and distill the organic layer. Redissolve it in chloroform, wash it twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and distill the remaining liquid under reduced pressure. The concentrated compound is subjected to silica gel column chromatography to obtain 2-1-1 (10.08g, yield 44%).

[0082] LC-MS (APCI): 487.26 (M+H + )

[0083] Step 2. Dissolve the intermediate 2-1 (17.71 g, 36.0 mmol) in 300 ml of tert-butylbenzene and cool to 0°C. Add tert-butyl lithium (1.7 M, 32.32 ml, 55.0 mmol) and stir at 60°C for 2 hours. Then cool the reactant to 0°C, add boron tribromide (5.4 mL, 55.0 mmol), and stir at room temperature for 0.5 hours. Cool the reactant to 0°C again, add N,N-diisopropylethylamine (9.6 mL, 55 mmol), and stir at 60°C for 2 hours. After the reaction is completed, cool to room temperature, separate the organic layer with chloroform and water, and distill the organic layer. Dissolve it in chloroform again, wash it twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir, filter, and distill the remaining liquid under reduced pressure. The concentrated compound was subjected to silica gel column chromatography to obtain 2-1 (4.35 g, yield 29%).

[0084] LC-MS (APCI): 417.52 (M+H + )

[0085] 2. Synthesis of Intermediate 2-2

[0086]

[0087] Step 1. Under nitrogen conditions, add 5-chloro-2,3-dibromo-1-fluorobenzene (15.86g, 55.0mmol), 4-(tert-butyl)phenol (8.26g, 55mmol), potassium carbonate (8.3g, 60mmol) and N-methylpyrrolidone (225ml), stir and reflux for 9 hours, cool at room temperature, separate the organic layer with chloroform and water, and distill the organic layer. Redissolve it in chloroform, wash it twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and distill the remaining liquid under reduced pressure. The concentrated compound is subjected to silica gel column chromatography to obtain 2-2-1 (8.0g, yield 35%).

[0088] LC-MS (APCI): 416.89 (M+H + )

[0089] Step 2. Add bis(4-(tert-butyl)phenyl)amine (3.38 g, 12 mmol) and sodium tert-butoxide (3.56 g, 37 mmol) into a three-necked flask, add toluene (150 mL) and replace the atmosphere with nitrogen twice, add 2-2-1 (5.02 g, 12 mmol) and catalyst Pd 2 (dba) 3(0.43g, 0.37mmoL), N2 was replaced three times, tri-tert-butylphosphine (0.06mL, 2.5mmoL) was injected, the temperature was raised to 70°C, and the reaction was carried out for 1h. The reaction solution was cooled, washed with water, and the palladium catalyst was removed by passing through diatomaceous earth, evaporated to dryness, and recrystallized from dichloromethane / petroleum ether to obtain a solid, which was then washed with a mixed solvent of toluene / ethyl acetate at 45°C for 2h, and filtered to obtain 2-2-2 (3.19g, yield 43%).

[0090] LC-MS (APCI): 618.64 (M+H + )

[0091] Step 3. Dissolve the intermediate 2-2-2 (22.28 g, 36.0 mmol) in 300 ml of tert-butylbenzene and cool to 0°C. Add tert-butyl lithium (1.7 M, 32.32 ml, 55.0 mmol) and stir at 60°C for 2 hours. Then cool the reactant to 0°C, add boron tribromide (5.4 mL, 55.0 mmol), and stir at room temperature for 0.5 hours. Cool the reactant to 0°C again, add N,N-diisopropylethylamine (9.6 mL, 55 mmol), and stir at 60°C for 2 hours. After the reaction is completed, cool to room temperature, separate the organic layer with chloroform and water, and distill the organic layer. Dissolve it in chloroform again, wash it twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir, filter, and distill the remaining liquid under reduced pressure. The concentrated compound was subjected to silica gel column chromatography to obtain 2-2 (5.33 g, yield 27%).

[0092] LC-MS (APCI): 548.72 (M+H + )

[0093] 3. Synthesis of Intermediate 2-3

[0094]

[0095] Step 1. Add bis(4-(tert-butyl)phenyl)amine (6.75 g, 24 mmol) and sodium tert-butoxide (7.12 g, 37 mmol) into a three-necked flask, add toluene (300 mL) and replace with nitrogen twice, add 1,2,3-tribromo-5-chlorobenzene (4.19 g, 12 mmol) and catalyst Pd 2 (dba) 3 (0.86g, 0.74mmoL), N2 replaced three times, injected tri-tert-butylphosphine (0.12mL, 5.0mmoL), heated to 70°C, reacted for 1h. The reaction solution was cooled, washed with water, passed through diatomaceous earth to remove the palladium catalyst, evaporated to dryness, recrystallized with dichloromethane / petroleum ether to obtain a solid, then washed with a mixed solvent of toluene / ethyl acetate at 45°C for 2h, and filtered to obtain 2-3-1 (5.04g, yield 56%).

[0096] LC-MS (APCI): 749.65 (M+H + )

[0097] Step 2. Dissolve the intermediate 2-3-1 (27.01 g, 36.0 mmol) in 300 ml of tert-butylbenzene and cool to 0°C. Add tert-butyl lithium (1.7 M, 32.32 ml, 55.0 mmol) and stir at 60°C for 2 hours. Then cool the reactant to 0°C, add boron tribromide (5.4 mL, 55.0 mmol), and stir at room temperature for 0.5 hours. Cool the reactant to 0°C again, add N,N-diisopropylethylamine (9.6 mL, 55 mmol), and stir at 60°C for 2 hours. After the reaction is completed, cool to room temperature, separate the organic layer with chloroform and water, and distill the organic layer. Dissolve it in chloroform again, wash it twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir, filter, and distill the remaining liquid under reduced pressure. The concentrated compound was subjected to silica gel column chromatography to obtain 2-3 (6.11 g, yield 25%).

[0098] LC-MS (APCI): 679.21 (M+H + )

[0099] 4. Synthesis of Intermediate 2-4

[0100]

[0101] Step 1. Under nitrogen conditions, add 2-bromo-5-chloro-1,3-difluorobenzene (12.51 g, 55.0 mmol), benzene 4-(tert-butyl)phenol (8.26 g, 55 mmol), potassium carbonate (8.3 g, 60 mmol) and N-methylpyrrolidone (225 ml), stir and reflux for 9 hours, cool at room temperature, separate the organic layer with chloroform and water, and distill the organic layer. Redissolve it in chloroform, wash it twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and distill the remaining liquid under reduced pressure. The concentrated compound is subjected to silica gel column chromatography to obtain 2-4-1 (8.26 g, yield 42%).

[0102] LC-MS (APCI): 357.86 (M+H + )

[0103] Step 2. Add 2,5-dibromo-1,3-difluorobenzene (19.67 g, 55.0 mmol), 2-4-2 (8.26 g, 55 mmol), potassium carbonate (8.3 g, 60 mmol) and N-methylpyrrolidone (225 ml) to the reaction vessel under nitrogen, stir and reflux for 9 hours, cool at room temperature, separate the organic layer with chloroform and water, and distill the organic layer. Redissolve it in chloroform, wash it twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir and filter, and distill the remaining liquid under reduced pressure. The concentrated compound is subjected to silica gel column chromatography to obtain 2-4-3 (12.07 g, yield 45%).

[0104] LC-MS (APCI): 487.61 (M+H + )

[0105] Step 3. Dissolve the intermediate 2-4-2 (17.56 g, 36.0 mmol) in 300 ml of tert-butylbenzene and cool to 0°C. Add tert-butyl lithium (1.7 M, 32.32 ml, 55.0 mmol) and stir at 60°C for 2 hours. Then cool the reactant to 0°C, add boron tribromide (5.4 mL, 55.0 mmol), and stir at room temperature for 0.5 hours. Cool the reactant to 0°C again, add N,N-diisopropylethylamine (9.6 mL, 55 mmol), and stir at 60°C for 2 hours. After the reaction is completed, cool to room temperature, separate the organic layer with chloroform and water, and distill the organic layer. Dissolve it in chloroform again, wash it twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir, filter, and distill the remaining liquid under reduced pressure. The concentrated compound was subjected to silica gel column chromatography to obtain 2-4 (4.05 g, yield 27%).

[0106] LC-MS (APCI): 417.38 (M+H + )

[0107] 5. Synthesis of Intermediate 2-5

[0108]

[0109] Compound 2-5 was synthesized by referring to the synthesis method of intermediate 2-2 to obtain compound 2-5 (4.95 g, yield 25%).

[0110] LC-MS (APCI): 550.62 (M+H + )

[0111] 6. Synthesis of Intermediate 2-6

[0112]

[0113] Compound 2-6 was synthesized by referring to the synthesis method of intermediate 2-2 to obtain compound 2-6 (4.54 g, yield 23%), wherein the synthesis method of C was referred to the synthesis of intermediate 2-3-1, and the raw materials were benzo[b]thiophene-3-amine and 1-bromo-4-tert-butylbenzene.

[0114] LC-MS (APCI): 548.25 (M+H + )

[0115] 7. Synthesis of Intermediate 2-7

[0116]

[0117] Step 1. Add bis(4-(tert-butyl)phenyl)amine (3.38 g, 12 mmol) and sodium tert-butoxide (3.56 g, 37 mmol) into a three-necked flask, add toluene (150 mL) and replace the nitrogen atmosphere twice, add 1,2,3-tribromo-5-chlorobenzene (4.19 g, 12 mmol) and catalyst Pd 2 (dba) 3 (0.43g, 0.37mmoL), N 2 Replace three times, inject tri-tert-butylphosphine (0.06mL, 2.5mmoL), heat to 70°C, and react for 1h. The reaction solution is cooled, washed with water, and the palladium catalyst is removed by passing through diatomaceous earth, evaporated to dryness, and recrystallized with dichloromethane / petroleum ether to obtain a solid, which is then washed with a mixed solvent of toluene / ethyl acetate at 45°C for 2h, and filtered to obtain 2-7-1 (3.41g, yield 52%).

[0118] LC-MS (APCI): 548.73 (M+H + )

[0119] Step 2. Add 2-7-2 (i.e., compound C) (3.38 g, 12 mmol) and sodium tert-butoxide (3.56 g, 37 mmol) to a three-necked flask, add toluene (150 mL), replace the atmosphere with nitrogen twice, add 2-7-1 (6.60 g, 12 mmol) and catalyst Pd 2 (dba) 3 (0.43g, 0.37mmoL), N 2 Replace three times, inject tri-tert-butylphosphine (0.06mL, 2.5mmoL), heat to 70℃, react for 1h. Cool the reaction solution, wash with water, remove the palladium catalyst through diatomaceous earth, evaporate to dryness, recrystallize with dichloromethane / petroleum ether to obtain a solid, then wash with a mixed solvent of toluene / ethyl acetate at 45℃ for 2h, and filter to obtain 2-7-3 (3.60g, yield 40%).

[0120] LC-MS (APCI): 749.38 (M+H + )

[0121] Step 3. Dissolve the intermediate 2-7-3 (26.78 g, 35.7 mmol) in 300 ml of tert-butylbenzene and cool to 0°C. Add tert-butyl lithium (1.7 M, 31.5 ml, 53.6 mmol) and stir at 60°C for 2 hours. Then cool the reactant to 0°C, add boron tribromide (5.2 mL, 53.6 mmol), and stir at room temperature for 0.5 hours. Cool the reactant to 0°C again, add N,N-diisopropylethylamine (9.3 mL, 53.6 mmol), and stir at 60°C for 2 hours. After the reaction is completed, cool to room temperature, separate the organic layer with chloroform and water, and distill the organic layer. Dissolve it in chloroform again, wash it twice with water, separate the organic layer, add anhydrous magnesium sulfate, stir, filter, and distill the remaining liquid under reduced pressure. The concentrated compound was subjected to silica gel column chromatography to obtain 2-7 (6.79 g, yield 28%).

[0122] LC-MS (APCI): 679.47 (M+H + )

[0123] 8. Synthesis of Intermediate 1-46-1

[0124]

[0125] 2-1 (27.67 g, 60 mol) and phenylboric acid (10.16 g, 65 mol) were placed in a flask and dissolved in toluene (200 ml). Pd(PPh 3 ) 4 (0.46 g, 0.4 mmol) and potassium carbonate (2 mol / L solution 70 ml), heated and stirred for 12 hours. After the reaction was completed, the reaction solution was extracted with dichloromethane and 1-46-1 (17.74 g, yield 60%) was obtained by column chromatography.

[0126] LC-MS (APCI): 493.53 (M+H + )

[0127] 9. Synthesis of Intermediate 1-46-3

[0128]

[0129] Under argon atmosphere, 1-46-2 (1.75 g, 5.0 mmol), copper (I) oxide (0.072 g, 0.5 mmol), 11.0 ml of N-methylamphetamine, 3.4 ml of 28% ammonia water were added to the flask, heated below 40 degrees for 10 minutes, and stirred. After the temperature was raised to 80 degrees, heated for 12 hours and stirred. The reaction solution was poured into water and ethyl acetate was extracted. The solvent was removed under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain compound 1-46-3 (1.28 g, yield 90%)

[0130] LC-MS (APCI): 286.34 (M+H + )

[0131] Example 1: Preparation of Compound 1-46

[0132]

[0133] Step 1. Add 1-46-3 (3.42 g, 12 mmol) and sodium tert-butoxide (3.56 g, 37 mmol) to a three-necked flask, add toluene (200 mL), replace the nitrogen atmosphere twice, add 2-1 (5.54 g, 12 mmol) and catalyst Pd 2 (dba) 3 (0.43 g, 0.37 mmol), N 2 Replace three times, inject tri-tert-butylphosphine (0.06mL, 2.5mmol), heat to 70℃, react for 1h. Cool the reaction solution, wash with water, remove the palladium catalyst through diatomaceous earth, evaporate to dryness, recrystallize with dichloromethane / petroleum ether to obtain a solid, then wash with a mixed solvent of toluene / ethyl acetate at 45℃ for 2h, filter and obtain 1-46-4 (5.34g, yield 60%).

[0134] LC-MS (APCI): 742.43 (M+H + )

[0135] Step 2.1-46-4 (8.90 g, 12 mmol) and sodium tert-butoxide (3.56 g, 37 mmol) were added to a three-necked flask, toluene (250 mL) was added, nitrogen was replaced twice, 1-46-1 (9.52 g, 12 mmol) and catalyst Pd were added 2 (dba) 3 (0.43 g, 0.37 mmol), N 2Replace three times, inject tri-tert-butylphosphine (0.06 mL, 2.5 mmol), heat to 70°C, react for 1 h. The reaction solution is cooled, washed with water, passed through diatomaceous earth to remove the palladium catalyst, evaporated to dryness, recrystallized with dichloromethane / petroleum ether to obtain a solid, then washed with a mixed solvent of toluene / ethyl acetate at 45°C for 2 h, and filtered to obtain 1-46 (6.73 g, yield 50%).

[0136] LC-MS (APCI): 1122.45 (M+H + )

[0137] Example 2: Preparation of Compound 1-1

[0138] Referring to the synthesis method of 1-46-4 in Example 1, except that compound 1-46-3 is replaced by aniline and compound 1-46-1 is replaced by compound 2-1, compound 1-1 can be synthesized to obtain compound 1-1 (6.86 g, yield 67%).

[0139] LC-MS (APCI): 854.25 (M+H + )

[0140] Example 3: Preparation of Compound 1-8

[0141] Referring to the synthesis method of Example 1-46, except replacing compound 1-46-1 with compound 2-1 and replacing compound 1-46-3 with 3-(1-phenyl-1H-benzimidazol-2-yl)aniline, compound 1-8 (5.90 g, yield 47%) was obtained.

[0142] LC-MS (APCI): 1046.42 (M+H + )

[0143] Example 4: Preparation of Compound 1-15

[0144]

[0145] To a solution of 7-bromonaphtho[1,2-b]benzofuran (5 g, 16.8 mmol) in methanol was added ammonium hydroxide (28%).

[0146] (10 mL, 0.03 mmol), Na 2 CO 3 (1.5 g, 14.1 mmol) and 0.10 g (0.14 mmol) as a catalyst

[0147] PdCl 2 (PPh 3 ) 2The reaction mixture was stirred at 80°C for an appropriate time. After the reaction was completed, the product was extracted with ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous magnesium sulfate, filtered and evaporated to obtain pure product b (2.4 g, yield 61%).

[0148] LC-MS (APCI): 234.08 (M+H + )

[0149] Referring to the synthesis method of Example 1-46, except that compound 1-46-3 was replaced by the product b synthesized above, and compound 1-46-1 was replaced by compound 2-1, compound 1-15 (7.16 g, yield 60%) was obtained.

[0150] LC-MS (APCI): 994.64 (M+H + )

[0151] Example 5: Preparation of Compound 1-29

[0152]

[0153] The synthesis of compound d was prepared by referring to the synthesis of compound b in Example 4.

[0154] Compound 1-29 (6.92 g, yield 56%) was synthesized by referring to the synthesis method of Example 1-46, except that compound 1-46-3 was replaced by the product d synthesized above, and compound 1-46-1 was replaced by compound 2-4.

[0155] LC-MS (APCI): 1030.45 (M+H + )

[0156] Example 6: Preparation of Compound 1-42

[0157]

[0158] Compound 1-42 was synthesized by referring to the synthesis method of Example 1-46 to obtain compound 1-42 (6.41 g, yield 47%). The synthesis method of compound 4 refers to the synthesis steps of 1-46-4, except that compound 4 was used instead of 1-46-3 in Example 1-46 to react with 2-1 and 2-2 in sequence.

[0159] LC-MS (APCI): 1037.16 (M+H + )

[0160] Example 7: Preparation of Compound 1-43

[0161]

[0162] Compound 1-43 was synthesized by referring to the synthesis method of Example 1-46 to obtain compound 1-43 (4.94 g, yield 40%), except that compound 9-aminophenanthrene was used instead of 1-46-3 in Example 1-46.

[0163] LC-MS (APCI): 1030.91 (M+H + )

[0164] Example 8: Preparation of Compound 1-50

[0165]

[0166] Compound 1-50 was synthesized by referring to the synthesis method of Example 1-46 to obtain compound 1-50 (5.79 g, yield 39%), except that compound 4-(4,6-diphenyl-1,3,5-triazine-2-yl)aniline was used instead of 1-46-3 in Example 1-46, and compound 1-46-1 was used instead of compound 2-1.

[0167] LC-MS (APCI): 1037.75 (M+H + )

[0168] Example 9: Preparation of Compound 1-53

[0169]

[0170] Compound 1-53 was synthesized by referring to the synthesis method of Example 1-46 to obtain compound 1-53 (6.23 g, yield 42%); except that compound 1-46-1 was used instead of compound 2-1, and compound D was used instead of 1-46-3 in Example 1-46, the synthesis of compound D was referred to the synthesis method of intermediate 1-46-1.

[0171] LC-MS (APCI): 1235.18 (M+H + )

[0172] Device preparation example:

[0173] This embodiment provides an organic electroluminescent device, such as Figure 1 As shown, it includes a first electrode layer 1, a hole injection layer 2, a hole transport layer 3, a light-emitting auxiliary layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7 and a second electrode layer 8.

[0174] The present invention deposits hole injection materials on the surface of ITO glass or anode with a light-emitting area of ​​2mm×2mm to form a hole injection layer (HIL) of 5-100nm and a hole transport layer (HTL) of 5-200nm; secondly, vacuum deposits BP with a thickness of 5-20nm on the hole transport layer to form a light-emitting auxiliary layer; then forms a luminescent layer (EML) of 10-100nm (which may contain the compound described in the present invention) on BP, forms an electron transport layer (ETL) of 20-200nm and an electron injection layer of 0.1-10nm and a cathode of 50-200nm; if necessary, an electron blocking layer (EBL) is added between the HTL and EML layers to manufacture an OLED device. The OLED is tested by a standard method. The device materials involved in the present invention can be obtained by known synthesis methods unless otherwise specified.

[0175] Comparative Example 1:

[0176] The structure of the device comparative example 1 provided by the present invention is specifically: ITO / HI (40nm) / HT (20nm) / Host: 3wt% doping (30nm) / ET (30nm) / Liq (1nm) / Al (100nm).

[0177] 2-TNATA was evaporated on the ITO substrate to form a first hole injection layer (HIL) with a thickness of 40 nm, HT was evaporated on the first hole injection layer to form a hole transport layer (HTL) with a thickness of 20 nm, (BH-1) + BD-1 (3 wt %) was evaporated on the hole transport layer to form a light-emitting layer (EML) with a thickness of 30 nm; ET was evaporated to form an electron transport layer (ETL) with a thickness of 30 nm, and an electron injection layer (EIL) was evaporated. And evaporated Al (thickness of 100 nm) to form a cathode, thereby manufacturing an organic electroluminescent device, which is recorded as Comparative Example 1.

[0178] The structural formula of the materials involved is as follows:

[0179]

[0180] Specifically, the efficiency test conditions are: at a current density of 15 mA / cm 2 The device efficiency is tested below, with the efficiency of comparative example 1 being 100%, and the efficiencies of other device embodiments relative to comparative example 1 are obtained.

[0181] The test conditions of driving voltage are: at a current density of 15mA / cm 2 The device driving voltage is tested, and the driving voltage of comparative example 1 is taken as 100%, and the driving voltages of other device embodiments relative to comparative example 1 are obtained.

[0182] The test conditions for the lifespan are: applying a voltage to the obtained organic electroluminescent element so that the current density reaches 30 mA / cm 2 , measure the time until the brightness reaches 95% relative to the initial brightness (LT95 (unit: hour)), take the time until the initial brightness of comparative example 1 reaches 95% as 100%, and obtain the life of other device embodiments relative to comparative example 1.

[0183] Device Example:

[0184] Device Examples 1-9 were prepared by a preparation method similar to that of Comparative Example 1, except that the doping material of the light-emitting layer of the OLED device was replaced by Compounds 1-46, 1-1, 1-8, 1-15, 1-29, 1-42, 1-43, 1-50, and 1-53, respectively, instead of BD-1. The luminescence characteristics test method of each device embodiment prepared above was the same as that of Comparative Example 1, and the specific data are shown in Table 1.

[0185] Table 1. Electroluminescence properties of organic light-emitting devices

[0186]

[0187]

[0188] As can be seen from Table 1, after the condensed ring compound of the present invention is applied to the organic electroluminescent device, compared with the comparative example, the driving voltage is lower, and the luminous efficiency and life characteristics of the device are also significantly improved. It is an organic light-emitting functional material with good performance and is expected to be commercially promoted and applied.

[0189] Although the present invention has been described in conjunction with the embodiments, the present invention is not limited to the above embodiments. It should be understood that under the guidance of the concept of the present invention, those skilled in the art can make various modifications and improvements, and the attached claims summarize the scope of the present invention. Obviously, the above embodiments are only examples for clear description, and are not limitations on the implementation methods. For ordinary technicians in the field, other different forms of changes or modifications can be made on the basis of the above description. It is not necessary and impossible to list all the implementation methods here. The obvious changes or modifications derived from this are still within the scope of protection created by the present invention.

Claims

1. A condensed ring compound, It is characterized in that The fused ring compound has a general structure as shown in Formula I: In Formula I, m and n are selected from integers between 0 and 3, and when m is 0, Q 1 Directly connected to N; when n is 0, Q 2 Directly connected to N; L is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl; R 1 -R 2 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 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heterocycloalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl; Q1 and Q2 are the same or different and are independently selected from the structure shown in formula (1): In formula (1), X 1 , X 2 The same or different, each independently selected from O, NR 10 , multiple R 10 When present, multiple R 10 Each is independent, identical or different from the other; R 7 -R 9 wherein one of them is the connection position between formula (I) and formula (1), and the others 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 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heterocycloalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl; R 3 -R 6 , R 10 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 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heterocycloalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl; When formula (2) or formula (3) is fused with formula (1) at the U or V position, and when formula (3) is fused with formula (1), the benzene rings of formula (3) are directly fused at the U or V position without being connected by a connecting bond; In the above formula, Y is selected from O and S; R 11 -R 14 Same or different, 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 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heteroalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl; The substituents in the "substituted or unsubstituted" are each independently selected from deuterium, halogen, cyano, silane, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, C3-C30 heteroaryl, The heteroatoms in the heteroarylene group, heterocycloalkyl group, heterocycloalkenyl group and heteroaryl group are each independently at least one of N, O, S, Si and P.

2. The fused ring compound according to claim 1, It is characterized in that The Q1 and Q2 are the same or different and are independently selected from the structures shown in Formula II-1 to Formula II-7: In the above formula, R 3 -R 7 , R 9 -R 14 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 heterocycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C3-C10 heterocycloalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl.

3. The fused ring compound according to any one of claims 1 or 2, It is characterized in that The L is selected from the following trivalent groups: phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, pyrenyl, peryl, triphenylene, pyridyl, bipyridyl, terpyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, pyrrolyl, furanyl, thienyl, indenyl, indolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, carbolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, phenanthrolinyl, benzoquinolyl, benzisoquinolyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, pyrazolyl, benzopyrazolyl, naphthyridinyl.

4. The fused ring compound according to any one of claims 1 or 2, It is characterized in that The R 1 -R 2 the same or different, each independently selected from hydrogen, deuterium, halogen, cyano, 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 peryl, substituted or unsubstituted triphenylene, 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 quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted indenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolyl, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted substituted or unsubstituted phenanthroline, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted benzisoquinolyl, 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 naphthyridinyl.

5. The fused ring compound according to any one of claims 1 or 2, It is characterized in that The R 3 -R 7 , R 9 , R 11 -R 14 The same or different, each independently selected from the following groups: hydrogen, deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, triphenylene, indenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl and combinations of two or more of the above groups.

6. The fused ring compound according to any one of claims 1 or 2, It is characterized in that The R 10 Any one selected from phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, pyrenyl, perylenyl, triphenylene, and deuterated, halogenated or tert-butyl substituted groups.

7. The organic electroluminescent device according to claim 6, It is characterized in that The condensed ring compound is selected from the following chemical structures:

8. An organic electroluminescent device, It is characterized in that The organic electroluminescent device comprises a first electrode, a second electrode and at least one organic functional layer disposed between the first electrode and the second electrode, wherein the at least one organic functional layer comprises the condensed ring compound according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, It is characterized in that The organic functional layer includes a hole injection layer, an electron transport layer, an electron blocking layer, a functional layer with both hole injection and hole transport functions, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a functional layer with both electron injection and electron transport functions. At least one of the hole injection layer, electron transport layer, electron blocking layer, a functional layer with both hole injection and hole transport functions, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a functional layer with both electron injection and electron transport functions contains the condensed ring compound described in any one of claims 1 to 7.

10. An electronic device, comprising a display or lighting device, It is characterized in that The device comprises the organic electroluminescent device according to any one of claims 8 to 9.

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