Organic electroluminescent compound and organic electroluminescent device containing same

Abstract

The invention provides an organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound has a structure as shown in a formula (1). The organic electroluminescent compound provided by the invention can be used as a main body material of a luminescent layer of a photoelectric device, the driving voltage of the device is reduced, the current efficiency is improved, and the service life is prolonged.

Description

[0001] This application is a divisional application of the patent application with the application number 202210161852.3 (the filing date of the original application is February 22, 2022, and the invention title is an organic electroluminescent compound and an organic electroluminescent device comprising the same). Technical Field

[0002] The present invention belongs to the technical field of organic optoelectronic materials, and particularly relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. Background Art

[0003] An organic electroluminescent device, such as an organic light-emitting diode (OLED), generally includes a cathode and an anode disposed opposite to each other, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an organic light-emitting layer, a hole transport layer located between the organic light-emitting layer and the anode, and an electron transport layer located between the organic light-emitting layer and the cathode. When a voltage is applied between the two electrodes, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light externally.

[0004] The prior art can prepare materials for the light-emitting layer in an organic electroluminescent device. However, the market has very strong requirements for expanding the uses and the applicable environments. The luminous efficiency of the existing light-emitting materials is not high enough. Therefore, it is still necessary to continue to research and develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0005] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide an organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound of the present invention can be used as the host material of the light-emitting layer of an optoelectronic device, reducing the driving voltage of the device, improving the current efficiency, and prolonging the service life.

[0006] To achieve this purpose, the present invention adopts the following technical solutions:

[0007] In a first aspect, the present invention provides an organic electroluminescent compound having the structure shown in formula (1):

[0008]

[0009] Wherein, Y 1 is selected from O or S;

[0010] X 1 is selected from N or CR X1 , X 2Selected from N or CR X2 , X 3 Selected from N or CR X3 , X 4 Selected from N or CR X4 , X 5 Selected from N or CR X5 , X 6 Selected from N or CR X6 , X 7 Selected from N or CR X7 , X 8 Selected from N or CR X8 , X 9 Selected from N or CR X9 , X 10 Selected from N or CR X10 , X 11 Selected from N or CR X11 , X 12 Selected from N or CR X12 ;

[0011] R X1 ~R X12 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, one or at least two methylenes in the substituted C1-C30 alkyl are replaced by -O- or -S- in a non-adjacent manner to O or S atoms, substituted or unsubstituted C2-C30 alkenyl, one or at least two methylenes in the substituted C2-C30 alkenyl are replaced by -O- or -S- in a non-adjacent manner to O or S atoms, substituted or unsubstituted C7-C60 aralkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C4-C60 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl C3-C60 heteroarylamino,

[0012] R X4 and R X5 or R X8 and R X9 form a ring, and the ring is

[0013] and / or, R X1 ~R X4 , R X5 ~R X8 or R X9 ~R X12Any two adjacent groups in form a ring A, and the ring A is wherein represents the fused position,

[0014] Alternatively, when any two adjacent groups among R X1 ~R X12 do not form a ring, at least one of X 1 ~X 12 is N;

[0015] Y 5 is selected from O or S;

[0016] Y 2 is selected from O or S;

[0017] R 1 is selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted C6-C30 aryloxy.

[0018] The organic electroluminescent compound provided by the present invention can be used as the host material of the light-emitting layer of optoelectronic devices, reducing the driving voltage of the devices, improving the current efficiency, and prolonging the service life.

[0019] Preferably, the organic electroluminescent compound has the structure shown below, or when any two adjacent groups among R X1 ~R X12 do not form a ring, at least one of X 1 , X 4 , X 5 , X 8 , X 9 or X 12 is N;

[0020]

[0021]

[0022]

[0023] wherein, Y 1 , Y 2 , Y 5 are each independently selected from O or S;

[0024] X 1 is selected from N or CR X1 , X 2 is selected from N or CR X2 , X 3 is selected from N or CR X3 , X 4Selected from N or CR X4 , X 5 Selected from N or CR X5 , X 6 Selected from N or CR X6 , X 7 Selected from N or CR X7 , X 8 Selected from N or CR X8 , X 9 Selected from N or CR X9 , X 10 Selected from N or CR X10 , X 11 Selected from N or CR X11 , X 12 Selected from N or CR X12 [[ID=3,4]];

[0025] R X1 ~R X12 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, one or at least two methylenes in the substituted C1-C30 alkyl are substituted by -O- or -S- in a non-adjacent manner to an O atom or an S atom, substituted or unsubstituted C2-C30 alkenyl, one or at least two methylenes in the substituted C2-C30 alkenyl are substituted by -O- or -S- in a non-adjacent manner to an O atom or an S atom, substituted or unsubstituted C7-C60 aralkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C4-C60 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl C3-C60 heteroarylamino;

[0026] R 1 Selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C6-C30 aryloxy.

[0027] Preferably, the Y 1 is O.

[0028] Preferably, the Y 2 is O.

[0029] Preferably, the Y 5 is O.

[0030] Preferably, the R 1 is phenyl.

[0031] Preferably, R X1 ~R X12 Any one or at least two of them are selected from the groups represented by Formula n-1:

[0032] Wherein, represents the attachment position of the group, and L is selected from any one of a linking bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group;

[0033] Z 1 is selected from N or CR Z1 , Z 2 is selected from N or CR Z2 , Z 3 is selected from N or CR Z3 , Z 4 is selected from N or CR Z4 , Z 5 is selected from N or CR Z5 ;

[0034] R Z1 -R Z5 are each independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, R Z1 -R Z5 exist independently of each other, or two adjacent ones of R Z1 -R Z5 are connected to form a ring, and the ring is a benzene ring or a naphthalene ring;

[0035] Alternatively, any one or at least two of R X1 ~R X12 are selected from the groups represented by Formula p-1:

[0036] Wherein, represents the attachment position of the group, and L, L 1 , L 2 are each independently selected from any one of a linking bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group;

[0037] Ar 1 , Ar 2 are each independently selected from a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group.

[0038] Preferably, the RX1 Selected from formula n-1.

[0039] Preferably, the R X2 Selected from formula n-1.

[0040] Preferably, the R X3 Selected from formula n-1.

[0041] Preferably, the R X4 Selected from formula n-1.

[0042] Preferably, the R X5 Selected from formula n-1.

[0043] Preferably, the R X6 Selected from formula n-1.

[0044] Preferably, the R X7 Selected from formula n-1.

[0045] Preferably, the R X8 Selected from formula n-1.

[0046] Preferably, the R X9 Selected from formula n-1.

[0047] Preferably, the R X10 Selected from formula n-1.

[0048] Preferably, the R X11 Selected from formula n-1.

[0049] Preferably, the R X12 Selected from formula n-1.

[0050] Preferably, the R X1 Selected from formula p-1.

[0051] Preferably, the R X2 Selected from formula p-1.

[0052] Preferably, the R X3 Selected from formula p-1.

[0053] Preferably, the R X4 Selected from formula p-1.

[0054] Preferably, the R X5 Selected from formula p-1.

[0055] Preferably, the R X6 Selected from formula p-1.

[0056] Preferably, the R X7 Selected from formula p-1.

[0057] Preferably, the R X8 is selected from Formula p-1.

[0058] Preferably, the R X9 is selected from Formula p-1.

[0059] Preferably, the R X10 is selected from Formula p-1.

[0060] Preferably, the R X11 is selected from Formula p-1.

[0061] Preferably, the R X12 is selected from Formula p-1.

[0062] Preferably, the R Z1 -R Z5 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted group as follows: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, bipyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl-substituted phenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl.

[0063] Preferably, the Ar 1 and Ar 2 are each independently selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, bipyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, dimethylfluorenyl, diphenylfluorenyl, benzodimethylfluorenyl, spirobifluorenyl, benzocarbazolyl, benzonaphthofuranyl or benzonaphthothiophenyl.

[0064] Preferably, in Formula n-1, Z 1 is selected from N, Z 5 is selected from N, Z 3 is selected from CR Z3 and Z 4 is selected from CR Z4 and Z 2 is selected from CR Z2 .

[0065] Preferably, Z 1 is selected from N, Z 3 is selected from N, Z 2 is selected from CR Z2 and Z 4 is selected from CR Z4 and Z 5 is selected from CR Z5 .

[0066] Preferably, Z 1 is selected from N, Z 3 is selected from N, Z 5 is selected from N, Z 4 is selected from CR Z4 , Z 2 is selected from CR Z2 .

[0067] Preferably, the formula n-1 is selected from

[0068] Preferably, the formula n-1 is selected from

[0069] Wherein, R Z1 -R Z5 are each independently selected from hydrogen, deuterium, substituted or unsubstituted groups as follows: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, bipyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl-substituted phenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl.

[0070] The substituents of the substitution are each independently selected from deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C6 alkyl, unsubstituted or R'-substituted C6-C12 aryl, unsubstituted or R'-substituted C2-C20 heteroaryl; R' is selected from deuterium, halogen, cyano, deuterium-substituted methyl, halogen-substituted methyl.

[0071] Preferably, the group represented by the formula n-1 is selected from any one of the following groups:

[0072]

[0073] Preferably, the group represented by the formula p-1 is selected from any one of the following groups:

[0074]

[0075]

[0076] Wherein the dashed line indicates the access position of the group.

[0077] Preferably, the organic electroluminescent compound is selected from any one of the following compounds in which the formula (1) is connected to the formula n-1:

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086] Preferably, the organic electroluminescent compound is selected from any one of the following compounds in which formula (1) is connected to formula p-1:

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] In a second aspect, the present invention provides a composition, which comprises a compound in which formula (1) is connected to formula n-1 and / or a compound in which formula (1) is connected to formula p-1.

[0095] Preferably, the mass ratio of the compound in which formula (1) is connected to formula n-1 to the compound in which formula (1) is connected to formula p-1 is 1:9 - 9:1, such as 1:9, 2:8, 3:7, 4:6, 5:5, 6:4, 7:3, 8:2 or 9:1, etc.

[0096] Preferably, the mass ratio of the compound in which formula (1) is connected to formula n-1 to the compound in which formula (1) is connected to formula p-1 is 2:8 - 8:2.

[0097] Preferably, the mass ratio of the compound in which formula (1) is connected to formula n-1 to the compound in which formula (1) is connected to formula p-1 is 3:7 - 7:3.

[0098] Preferably, the mass ratio of the compound in which formula (1) is connected to formula n-1 to the compound in which formula (1) is connected to formula p-1 is 4:6 - 6:4.

[0099] In a third aspect, the present invention provides an organic electroluminescent device, which includes a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, and the material of the organic layer includes at least one of the organic electroluminescent compounds as described in the first aspect.

[0100] Preferably, the material of the organic layer includes at least one of the compositions as described in the second aspect.

[0101] Preferably, the organic layer includes a light-emitting layer, and the material of the light-emitting layer includes at least one of the organic electroluminescent compounds as described in the first aspect.

[0102] Preferably, the organic layer includes a light-emitting layer, and the material of the light-emitting layer includes at least one of the compositions as described in the second aspect.

[0103] Preferably, the material of the light-emitting layer further includes a transition metal complex.

[0104] Preferably, the material of the light-emitting layer further includes a complex containing Ir or Pt.

[0105] In a fourth aspect, the present invention provides an electronic product, which includes the organic electroluminescent device as described in the third aspect.

[0106] As used in the present invention, the term "organic electroluminescent compound" means a compound that can be used in an organic electroluminescent device and can be included in any layer constituting the organic electroluminescent device as needed.

[0107] As used in the present invention, the term "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent element and can include at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent element. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, an electron blocking material, a light-emitting auxiliary material, a light-emitting layer material (including a host material and a doping material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0108] The organic electroluminescent material of the present invention can include at least one compound represented by formula (1). Although not limited thereto, the compound having formula (1) can be included in the light-emitting layer. In this case, the compound having formula (1) can be included as a host. If necessary, the host material can include two or more compounds of formula (1). Moreover, the compound having formula (1) can be included in the electron transport region, and not limited thereto, the compound having formula (1) can be included in the electron buffer layer.

[0109] Hereinafter, each layer of the organic electroluminescent element containing the compound of Formula 1 of the present invention will be described.

[0110] Substrate

[0111] An organic EL element is usually fabricated on a light-transmissive substrate. This light-transmissive substrate is a substrate for supporting the organic EL element, and the transmittance of light in the visible region with a wavelength of 400 - 700 nm is preferably 50% or more, and a smooth substrate is further preferably used.

[0112] Examples of such light-transmissive substrates include glass plates, synthetic resin plates, etc. Examples of glass plates include plates formed from soda-lime glass, barium- and strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz, etc. In addition, examples of synthetic resin plates include plates of polycarbonate resin, acrylic resin, polyethylene terephthalate resin, polyether sulfide resin, polysulfone resin, etc.

[0113] Anode

[0114] The anode functions to inject holes into the hole transport layer or the light-emitting layer, and it is effective to have a work function of 4 eV or more (preferably 4.45 eV or more). Specific examples of anode materials include carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, etc. and their alloys, metal oxides such as tin oxide and indium oxide used in ITO substrates and NESA substrates, and organic conductive resins such as polythiophene or polypyrrole.

[0115] Cathode

[0116] As the cathode, a cathode using a metal, alloy, conductive compound, or a mixture thereof with a small work function (less than 4 eV) as the electrode material can be used. Specific examples of such electrode materials include magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, etc. and their alloys, and there is no particular limitation on them. As representative examples of such alloys, magnesium / silver, magnesium / indium, lithium / aluminum, etc. can be cited, and there is no particular limitation on them. The ratio of the alloy is controlled by the temperature, atmosphere, vacuum degree, etc. of the evaporation source, and an appropriate ratio is selected. The anode and cathode can also be formed by two or more layers as needed.

[0117] Light-emitting layer

[0118] The light-emitting layer has functions of carrier injection, carrier transport, and light emission. The light-emitting layer material includes a host material and a guest material, and the guest material includes a phosphorescent guest material, a fluorescent guest material, a TADF guest material, etc.

[0119] Hole injection layer / hole transport layer

[0120] The hole injection layer / hole transport layer is a layer that helps inject holes into the light-emitting layer and transport the holes to the light-emitting region. It has a large hole mobility and usually a small ionization energy of 5.7 eV or less. As such a hole injection layer / hole transport layer, a material that transports holes to the light-emitting layer with a lower electric field strength is preferred. More preferably, the hole mobility is, for example, 10 4 -10 6 cm -4 / V·s or more when an electric field of 10 2 V / cm is applied. Examples of known hole transport layer materials include bis(N-(1-naphthyl)-n-phenyl)benzidine (α-NPD), N,N'-di(naphthalen-1-yl)-N,N'-biphenylbenzidine (NPB), or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), etc.

[0121] Electron injection layer / electron transport layer

[0122] The electron injection layer / electron transport layer is a layer that helps inject electrons into the light-emitting layer and transport the electrons to the light-emitting region. It has a large electron mobility. The adhesion improvement layer is an electron injection layer containing a material with particularly good adhesion to the cathode.

[0123] Specific examples of materials used in the electron injection layer include LiF, Liq, Li2O, BaO, NaCl, CsF, etc., and there are no particular limitations on them.

[0124] The functions of the OLED can be achieved by combining the various layers described above, or some layers can be completely omitted. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sub-layers. For example, the light-emitting layer can have two different light-emitting materials to achieve the desired emission spectrum.

[0125] To form each layer of the organic electroluminescent device of the present invention, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as inkjet printing, nozzle printing, slot die coating, spin coating, dip coating, flow coating methods, etc. can be used. The organic electroluminescent compounds of the present invention can be formed into a film by co-evaporation method or mixture evaporation method.

[0126] Definition of substituent terms

[0127] As used in the present invention, the term "halogen" can include fluorine, chlorine, bromine, or iodine, preferably fluorine.

[0128] As used in the present invention, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 30 carbon atoms, and examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0129] As used in the present invention, the term "C3-C30 cycloalkyl" refers to a monocyclic hydrocarbon or polycyclic hydrocarbon derived from a hydrocarbon having 1 to 30 ring backbone carbon atoms, and the cycloalkanes may include cyclopropyl, cyclobutyl, adamantyl, and the like.

[0130] In the present invention, aryl and arylene include monocyclic, polycyclic, or fused-ring aryl groups, and the rings may be interrupted by short non-aromatic units and may include spiro structures, including but not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, fluorenyl, spirobifluorenyl, and the like.

[0131] In the present invention, heteroaryl and heteroarylene include monocyclic, polycyclic, or fused-ring heteroaryl groups, and the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Including but not limited to furyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and their derivatives, and the like.

[0132] As used in the present invention, the term "C6-C30 aryloxy" refers to a monovalent substituent represented by RO-, where R represents an aryl group having 6 to 30 carbon atoms. Examples of such aryloxy include, but are not limited to, phenoxy, naphthyloxy, diphenoxy, and the like.

[0133] As used in the present invention, the term "C1-C30 alkylamino" refers to

[0134] As used in the present invention, the term "C6-C60 arylamino" refers to

[0135] As used in the present invention, the term "C3-C60 heteroarylamino" refers to

[0136] As used in the present invention, the term "C6-C60 aryl C3-C60 heteroarylamino" refers to

[0137] As used in the present invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position is not limited to a specific position, as long as the hydrogen at that position can be replaced by a substituent. When there are two or more substituents, the two or more substituents may be the same or different.

[0138] As used in the present invention, unless otherwise specified, a hydrogen atom includes protium, deuterium, and tritium.

[0139] In the present invention, in the definition of a group, the range of the number of carbon atoms is defined, and the number of carbon atoms is any integer within the defined range. For example, C6-C60 aryl means that the number of carbon atoms of the aryl can be any integer within the range of 6-60, such as 6, 8, 10, 15, 20, 30, 35, 40, 45, 50, 55, or 60, etc.

[0140] Compared with the prior art, the present invention has at least the following beneficial effects:

[0141] The organic electroluminescent compound provided by the present invention can be used as the host material of the light-emitting layer of an optoelectronic device, reducing the driving voltage of the device (3.66 - 3.85 V), increasing the current efficiency (17 - 23 Cd / A), and extending the lifespan (240 - 315 hours). Detailed Embodiments

[0142] The technical solution of the present invention will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.

[0143] Synthesis Example 1

[0144] Synthesis of Intermediate 4-3, and its synthesis route is as follows:

[0145]

[0146] The specific synthesis steps are as follows:

[0147] Synthesis of Intermediate 4-1: In a 50 mL three-necked flask, add Raw Material 1 (1 mmol), Raw Material 2 (1 mmol), cesium carbonate (1 mmol), copper(I) iodide (0.01 mmol), and N,N-dimethylformamide (10 mL). Heat the mixture to 110 °C for reaction. After the reaction is completed, wash with water, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the organic solvent by rotary evaporation, and separate the crude product by column chromatography (ethyl acetate:n-hexane = 1:50) to obtain Intermediate 4-1 (yield 43%).

[0148] HRMS(ESI) m / z [M+H]+: Found: 330.11.

[0149] Synthesis of Intermediate 4-2: In a 50 mL three-necked flask, Intermediate 4-1 (1 mmol), triphenylphosphine (10 mL), palladium(II) pivalate (0.05 mmol), potassium acetate (1.2 mmol), and pivalic acid (1 mmol) were added. The mixture was heated under reflux. After the reaction was completed, the reaction was quenched with water, and the mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, and the organic solvent was removed by rotary evaporation. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain Intermediate 4-2 (yield 48%).

[0150] HRMS(ESI) m / z [M+H]+: Found: 294.23.

[0151] Synthesis of Intermediate 4-3: In a 50 mL three-necked round-bottom flask, Intermediate 4-2 (10 mmol), bis(pinacolato)diboron (12 mmol), sodium acetate (20 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.5 mmol), and 2-(dicyclohexylphosphino)-2',6'-dimethoxybiphenyl (1.5 mmol) were added. Then 1,4-dioxane (20 mL) was added, and the flask was purged with nitrogen three times. Under nitrogen protection, the mixture was heated to 100 °C for reaction. After the reaction was completed, the reaction was quenched with water, and the mixture was extracted with dichloromethane. The organic solvent was removed by rotary evaporation. The crude product was separated by column chromatography (ethyl acetate: n-hexane (volume ratio 1:50)) to obtain Intermediate 4-3 (yield 73%).

[0152] HRMS(ESI) m / z [M+H]+: Found: 386.30.

[0153] Synthesis Example 2

[0154] Synthesis of Intermediate 5-3, and the synthetic route is as follows:

[0155]

[0156] The specific synthesis steps are as follows:

[0157] Synthesis of Intermediate 5-1: Similar to the synthesis of Intermediate 4-1, except that raw material 4 was used instead of raw material 2 to obtain Intermediate 5-1 (yield 41%).

[0158] HRMS(ESI) m / z [M+H]+: Found: 329.16.

[0159] Synthesis of Intermediate 5-2: Similar to the synthesis of Intermediate 4-2, except that Intermediate 5-1 was used instead of Intermediate 4-1 to obtain Intermediate 5-2 (yield 46%).

[0160] HRMS(ESI) m / z [M+H]+: Found: 293.13.

[0161] Synthesis of Intermediate 5-3: The same as the synthesis of Intermediate 4-3, except that Intermediate 5-2 was used instead of Intermediate 4-2 to obtain Intermediate 5-3 (yield 75%).

[0162] HRMS(ESI) m / z [M+H]+: Found: 385.06.

[0163] Synthesis Example 3

[0164] Synthesis of Intermediate 6-2: The synthetic route is as follows:

[0165]

[0166] The specific synthesis steps are as follows:

[0167] Synthesis of Intermediate 6-1: The same as the synthesis of Intermediate 4-1, except that Raw Material 4 was used instead of Raw Material 2 and Raw Material 5 was used instead of Raw Material 1 to obtain Intermediate 6-1 (yield 40%).

[0168] HRMS(ESI) m / z [M+H]+: Found: 329.14.

[0169] Synthesis of Intermediate 6-2: The same as the synthesis of Intermediate 4-2, except that Intermediate 6-1 was used instead of Intermediate 4-1 to obtain Intermediate 6-2 (yield 48%).

[0170] HRMS(ESI) m / z [M+H]+: Found: 293.24.

[0171] Synthesis Example 4

[0172] Synthesis of Intermediate 7-4: The synthetic route is as follows:

[0173]

[0174] The specific synthesis steps are as follows:

[0175] Synthesis of Intermediate 7-1: In a 50 mL three-necked flask, add Raw Material 7 (1 mmol), Raw Material 8 (1 mmol), toluene (9 mL), ethanol (3 mL), water (3 mL), add tetrakis(triphenylphosphine)palladium (0.05 mmol), potassium carbonate (2 mmol), heat to 80 °C, react for 5 hours. After the reaction is completed, cool to room temperature, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain Intermediate 7-1 (yield 42%).

[0176] HRMS(ESI) m / z [M+H]+: Measured value: 322.14.

[0177] Synthesis of intermediate 7-2: The same as the synthesis of intermediate 4-1, except that intermediate 7-1 was used to replace raw material 1, to obtain intermediate 7-2 (yield 38%).

[0178] HRMS(ESI) m / z [M+H]+: Measured value: 433.25.

[0179] Synthesis of intermediate 7-3: The same as the synthesis of intermediate 4-2, except that intermediate 7-2 was used to replace intermediate 4-1, to obtain intermediate 7-3 (yield 51%).

[0180] HRMS(ESI) m / z [M+H]+: Measured value: 399.24.

[0181] Synthesis of intermediate 7-4: The same as the synthesis of intermediate 4-3, except that intermediate 7-3 was used to replace intermediate 4-2, to obtain intermediate 7-4 (yield 77%).

[0182] HRMS(ESI) m / z [M+H]+: Measured value: 489.12.

[0183] Synthesis Example 5

[0184] Synthesis of intermediate 8-3 and intermediate 8-4, and the synthesis route is as follows:

[0185]

[0186] The specific synthesis steps are as follows:

[0187] Synthesis of intermediate 8-1: In a 50 mL three-necked flask, add raw material 10 (1 mmol), raw material 8 (1 mmol), toluene (9 mL), ethanol (3 mL), water (3 mL), add tetrakis(triphenylphosphine)palladium (0.05 mmol), potassium carbonate (2 mmol), heat to 80 °C, react for 5 hours. After the reaction is completed, cool to room temperature, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate 8-1 (yield 40%).

[0188] HRMS(ESI) m / z [M+H]+: Measured value: 322.21.

[0189] Synthesis of intermediate 8-2: The same as the synthesis of intermediate 4-1, except that intermediate 8-1 was used to replace raw material 1, to obtain intermediate 8-2 (yield 39%).

[0190] HRMS(ESI) m / z [M+H]+: Measured value: 432.14.

[0191] Synthesis of intermediate 8-3: The same as the synthesis of intermediate 4-2, except that intermediate 8-2 is used to replace intermediate 4-1 to obtain intermediate 8-3 (yield 49%).

[0192] HRMS(ESI) m / z [M+H]+: Measured value: 396.16.

[0193] Synthesis of intermediate 8-4: The same as the synthesis of intermediate 4-3, except that intermediate 8-3 is used to replace intermediate 4-2 to obtain intermediate 8-4 (yield 75%).

[0194] HRMS(ESI) m / z [M+H]+: Measured value: 488.33.

[0195] Synthesis Example 6

[0196] Synthesis of intermediate 11-3 and intermediate 11-4, and the synthetic route is as follows:

[0197]

[0198] The specific synthesis steps are as follows:

[0199] Synthesis of intermediate 11-1: The same as the synthesis of intermediate 4-1, except that raw material 15 is used to replace raw material 1 to obtain intermediate 11-1 (yield 40%).

[0200] HRMS(ESI) m / z [M+H]+: Measured value: 323.14.

[0201] Synthesis of intermediate 11-2: The same as the synthesis of intermediate 8-1, except that intermediate 11-1 is used to replace raw material 10 and raw material 16 is used to replace raw material 8 to obtain intermediate 11-2 (yield 36%).

[0202] HRMS(ESI) m / z [M+H]+: Measured value: 433.17.

[0203] Synthesis of intermediate 11-3: The same as the synthesis of intermediate 4-2, except that intermediate 11-2 is used to replace intermediate 4-1 to obtain intermediate 11-3 (yield 47%).

[0204] HRMS(ESI) m / z [M+H]+: Measured value: 397.23.

[0205] Synthesis of intermediate 11-4: The same as the synthesis of intermediate 4-3, except that intermediate 11-3 is used to replace intermediate 4-2 to obtain intermediate 11-4 (yield 79%).

[0206] HRMS(ESI) m / z [M+H]+: Measured value: 489.20.

[0207] Synthesis Example 7

[0208] Synthesis of Intermediate 13-3 and Intermediate 13-4, and the synthesis route is as follows:

[0209]

[0210] The specific synthesis steps are as follows:

[0211] Synthesis of Intermediate 13-1: Similar to the synthesis of Intermediate 4-1, except that raw material 19 is used instead of raw material 1 to obtain Intermediate 13-1 (yield 41%).

[0212] HRMS(ESI) m / z [M+H]+: Measured value: 323.15.

[0213] Synthesis of Intermediate 13-2: Similar to the synthesis of Intermediate 8-1, except that Intermediate 13-1 is used instead of raw material 10, and raw material 16 is used instead of raw material 8 to obtain Intermediate 13-2 (yield 38%).

[0214] HRMS(ESI) m / z [M+H]+: Measured value: 433.17.

[0215] Synthesis of Intermediate 13-3: Similar to the synthesis of Intermediate 4-2, except that Intermediate 13-2 is used instead of Intermediate 4-1 to obtain Intermediate 13-3 (yield 46%).

[0216] HRMS(ESI) m / z [M+H]+: Measured value: 397.15.

[0217] Synthesis of Intermediate 13-4: Similar to the synthesis of Intermediate 4-3, except that Intermediate 13-3 is used instead of Intermediate 4-2 to obtain Intermediate 13-4 (yield 77%).

[0218] HRMS(ESI) m / z [M+H]+: Measured value: 489.32.

[0219] Synthesis Example 8

[0220] Synthesis of Intermediate 15-3 and Intermediate 15-4, and the synthesis route is as follows:

[0221]

[0222] The specific synthesis steps are as follows:

[0223] Synthesis of Intermediate 15-1: Similar to the synthesis of Intermediate 4-1, except that raw material 15 is used instead of raw material 1, and raw material 4 is used instead of raw material 2 to obtain Intermediate 15-1 (yield 43%).

[0224] HRMS(ESI) m / z [M+H]+: Observed value: 322.14.

[0225] Synthesis of Intermediate 15-2: The same as the synthesis of Intermediate 8-1, except that Intermediate 15-1 is used to replace Raw Material 10, and Raw Material 16 is used to replace Raw Material 8, to obtain Intermediate 15-2 (yield 37%).

[0226] HRMS(ESI) m / z [M+H]+: Observed value: 432.16.

[0227] Synthesis of Intermediate 15-3: The same as the synthesis of Intermediate 4-2, except that Intermediate 15-2 is used to replace Intermediate 4-1, to obtain Intermediate 15-3 (yield 45%).

[0228] HRMS(ESI) m / z [M+H]+: Observed value: 396.13.

[0229] Synthesis of Intermediate 15-4: The same as the synthesis of Intermediate 4-3, except that Intermediate 15-3 is used to replace Intermediate 4-2, to obtain Intermediate 15-4 (yield 74%).

[0230] HRMS(ESI) m / z [M+H]+: Observed value: 488.35.

[0231] Synthesis Example 9

[0232] Synthesis of Intermediate 17-3 and Intermediate 17-4, and the synthetic route is as follows:

[0233]

[0234] The specific synthesis steps are as follows:

[0235] Synthesis of Intermediate 17-1: The same as the synthesis of Intermediate 4-1, except that Raw Material 19 is used to replace Raw Material 1, and Raw Material 4 is used to replace Raw Material 2, to obtain Intermediate 17-1 (yield 45%).

[0236] HRMS(ESI) m / z [M+H]+: Observed value: 322.14.

[0237] Synthesis of Intermediate 17-2: The same as the synthesis of Intermediate 8-1, except that Intermediate 17-1 is used to replace Raw Material 10, and Raw Material 16 is used to replace Raw Material 8, to obtain Intermediate 17-2 (yield 37%).

[0238] HRMS(ESI) m / z [M+H]+: Observed value: 432.18.

[0239] Synthesis of Intermediate 17-3: The same as the synthesis of Intermediate 4-2, except that Intermediate 17-2 is used instead of Intermediate 4-1 to obtain Intermediate 17-3 (yield 47%).

[0240] HRMS(ESI) m / z [M+H]+: Found: 396.12.

[0241] Synthesis of Intermediate 17-4: The same as the synthesis of Intermediate 4-3, except that Intermediate 17-3 is used instead of Intermediate 4-2 to obtain Intermediate 17-4 (yield 76%).

[0242] HRMS(ESI) m / z [M+H]+: Found: 488.23.

[0243] Synthesis Example 10

[0244] Synthesis of Intermediate 19-4 and Intermediate 19-5. The synthetic route is as follows:

[0245]

[0246]

[0247] The specific synthesis steps are as follows:

[0248] Synthesis of Intermediate 19-1: The same as the synthesis of Intermediate 8-1, except that Raw Material 25 is used instead of Raw Material 10, and Raw Material 24 is used instead of Raw Material 8 to obtain Intermediate 19-1 (yield 34%).

[0249] HRMS(ESI) m / z [M+H]+: Found: 273.04.

[0250] Synthesis of Intermediate 19-2: In a 50 mL three-necked flask, add Intermediate 19-1 (1 mmol), potassium carbonate (1.1 mmol), N,N-dimethylformamide (10 mL), heat to 50 °C and react for 2 hours. After the reaction, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, and separate the crude product by column chromatography (ethyl acetate: n-hexane (volume ratio 1:50)) to obtain Intermediate 19-2 (yield 44%).

[0251] HRMS(ESI) m / z [M+H]+: Found: 253.16.

[0252] Synthesis of Intermediate 19-3: The same as the synthesis of Intermediate 4-1, except that Intermediate 19-2 is used instead of Raw Material 1, and Raw Material 10 is used instead of Raw Material 2 to obtain Intermediate 19-3 (yield 42%).

[0253] HRMS(ESI) m / z [M+H]+: Found: 446.19.

[0254] Synthesis of Intermediate 19-4: The synthesis was the same as that of Intermediate 4-2, except that Intermediate 19-3 was used instead of Intermediate 4-1 to obtain Intermediate 19-4 (yield 47%).

[0255] HRMS(ESI) m / z [M+H]+: Found: 410.41.

[0256] Synthesis of Intermediate 19-5: The synthesis was the same as that of Intermediate 4-3, except that Intermediate 19-4 was used instead of Intermediate 4-2 to obtain Intermediate 19-5 (yield 76%).

[0257] HRMS(ESI) m / z [M+H]+: Found: 502.08.

[0258] Synthesis Example 11

[0259] Synthesis of Intermediate 21-4 and Intermediate 21-5. The synthetic route is as follows:

[0260]

[0261] The specific synthesis steps are as follows:

[0262] Synthesis of Intermediate 21-1: The synthesis was the same as that of Intermediate 8-1, except that starting material 28 was used instead of starting material 8 to obtain Intermediate 21-1 (yield 39%).

[0263] HRMS(ESI) m / z [M+H]+: Found: 304.14.

[0264] Synthesis of Intermediate 21-2: In a 50 mL three-necked flask, Intermediate 21-1 (1 mmol), potassium carbonate (1.1 mmol), and N,N-dimethylformamide (10 mL) were added, and the mixture was heated to 50 °C and reacted for 2 hours. After the reaction was completed, it was extracted with ethyl acetate. The organic phase was dried with anhydrous magnesium sulfate, and the crude product was separated by column chromatography (ethyl acetate: n-hexane (volume ratio 1:50)) to obtain Intermediate 21-2 (yield 42%).

[0265] HRMS(ESI) m / z [M+H]+: Found: 492.05.

[0266] Synthesis of Intermediate 21-3: The synthesis was the same as that of Intermediate 4-2, except that Intermediate 21-2 was used instead of Intermediate 4-1 to obtain Intermediate 21-3 (yield 42%).

[0267] HRMS(ESI) m / z [M+H]+: Found: 412.15.

[0268] Synthesis of Intermediate 21-4: In a 25 mL three-necked flask, add Intermediate 21-3 (1 mmol), Pd(OAc)2 (0.05 mmol), 3-nitropyridine (0.05 mmol). After displacing the air with nitrogen three times, add hexafluorobenzene (1.5 mL), 1,3-dimethyl-2-imidazolidinone (1 mL), PhCO2-Ot-Bu (2 mmol). Heat to 90 °C under nitrogen protection and react for 4 hours. Then cool to room temperature. The crude product is separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain Intermediate 21-4 (yield 47%).

[0269] HRMS(ESI) m / z [M+H]+: Found: 410.11.

[0270] Synthesis of Intermediate 21-5: The synthesis is the same as that of Intermediate 4-3, except that Intermediate 21-4 is used instead of Intermediate 4-2 to obtain Intermediate 21-5 (yield 79%).

[0271] HRMS(ESI) m / z [M+H]+: Found: 502.13.

[0272] Synthesis Example 12

[0273] Synthesis of Intermediate 23-5. The synthetic route is as follows:

[0274]

[0275] The specific synthesis steps are as follows:

[0276] Synthesis of Intermediate 23-1: The synthesis is the same as that of Intermediate 8-1, except that starting material 28 is used instead of starting material 8 to obtain Intermediate 23-1 (yield 39%).

[0277] HRMS(ESI) m / z [M+H]+: Found: 304.17.

[0278] Synthesis of Intermediate 23-2: In a 50 mL three-necked flask, add Intermediate 23-1 (1 mmol), potassium carbonate (1.1 mmol), N,N-dimethylformamide (10 mL). Heat to 50 °C and react for 2 hours. After the reaction is completed, extract with ethyl acetate. The organic phase is dried with anhydrous magnesium sulfate. The crude product is separated by column chromatography (ethyl acetate: n-hexane (volume ratio 1:50)) to obtain Intermediate 23-2 (yield 42%).

[0279] HRMS(ESI) m / z [M+H]+: Found: 492.07.

[0280] Synthesis of Intermediate 23-3: Similar to the synthesis of Intermediate 4-2, except that Intermediate 23-2 is used instead of Intermediate 4-1 to obtain Intermediate 23-3 (yield 42%).

[0281] HRMS(ESI) m / z [M+H]+: Found: 412.09.

[0282] Synthesis of Intermediate 23-4: In a 25 mL three-necked flask, add Intermediate 23-3 (1 mmol), Pd(OAc)2 (0.05 mmol), 3-nitropyridine (0.05 mmol). After displacing with nitrogen three times, add hexafluorobenzene (1.5 mL), 1,3-dimethyl-2-imidazolidinone (1 mL), PhCO2-Ot-Bu (2 mmol). Heat to 90 °C under nitrogen protection and react for 4 hours. Then cool to room temperature. The crude product is separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain Intermediate 23-4 (yield 47%).

[0283] HRMS(ESI) m / z [M+H]+: Found: 410.18.

[0284] Synthesis of Intermediate 23-5: Similar to the synthesis of Intermediate 4-3, except that Intermediate 23-4 is used instead of Intermediate 4-2 to obtain Intermediate 23-5 (yield 79%).

[0285] HRMS(ESI) m / z [M+H]+: Found: 502.21.

[0286] Synthesis Example 13

[0287] Synthesis of Intermediate 24-4 and Intermediate 24-5. The synthetic route is as follows:

[0288]

[0289] The specific synthesis steps are as follows:

[0290] Synthesis of Intermediate 24-1: Similar to the synthesis of Intermediate 8-1, except that raw material 25 is used instead of raw material 10, and raw material 24 is used instead of raw material 8 to obtain Intermediate 24-1 (yield 32%).

[0291] HRMS(ESI) m / z [M+H]+: Found: 272.99.

[0292] Synthesis of Intermediate 24-2: In a 50 mL three-necked flask, add Intermediate 24-1 (1 mmol), potassium carbonate (1.1 mmol), and N,N-dimethylformamide (10 mL). Heat the mixture to 50 °C and react for 2 hours. After the reaction, extract with ethyl acetate. Dry the organic phase with anhydrous magnesium sulfate. Separate the crude product by column chromatography (ethyl acetate: n-hexane (volume ratio 1:50)) to obtain Intermediate 24-2 (yield 45%).

[0293] HRMS(ESI) m / z [M+H]+: Found: 253.04.

[0294] Synthesis of Intermediate 24-3: Similar to the synthesis of Intermediate 4-1, except that Intermediate 24-2 is used to replace Raw Material 1 and Raw Material 7 is used to replace Raw Material 2, to obtain Intermediate 24-3 (yield 42%).

[0295] HRMS(ESI) m / z [M+H]+: Found: 446.07.

[0296] Synthesis of Intermediate 24-4: Similar to the synthesis of Intermediate 4-2, except that Intermediate 24-3 is used to replace Intermediate 4-1, to obtain Intermediate 24-4 (yield 44%).

[0297] HRMS(ESI) m / z [M+H]+: Found: 410.23.

[0298] Synthesis of Intermediate 24-5: Similar to the synthesis of Intermediate 4-3, except that Intermediate 24-4 is used to replace Intermediate 4-2, to obtain Intermediate 24-5 (yield 71%).

[0299] HRMS(ESI) m / z [M+H]+: Found: 502.20.

[0300] Synthesis Example 14

[0301] Synthesis of Intermediate 26-4 and Intermediate 26-5. The synthetic route is as follows:

[0302]

[0303] The specific synthesis steps are as follows:

[0304] Synthesis of Intermediate 26-1: Similar to the synthesis of Intermediate 8-1, except that Raw Material 25 is used to replace Raw Material 10 and Raw Material 24 is used to replace Raw Material 8, to obtain Intermediate 26-1 (yield 34%).

[0305] HRMS(ESI) m / z [M+H]+: Found: 273.04.

[0306] Synthesis of Intermediate 26-2: In a 50 mL three-necked flask, add Intermediate 26-1 (1 mmol), potassium carbonate (1.1 mmol), and N,N-dimethylformamide (10 mL). Heat the mixture to 50 °C and react for 2 hours. After the reaction is completed, extract with ethyl acetate. Dry the organic phase with anhydrous magnesium sulfate. Separate the crude product by column chromatography (ethyl acetate:n-hexane (volume ratio 1:50)) to obtain Intermediate 26-2 (yield 46%).

[0307] HRMS(ESI) m / z [M+H]+: Found: 253.08.

[0308] Synthesis of Intermediate 26-3: The synthesis is the same as that of Intermediate 4-1, except that Intermediate 26-2 is used to replace Raw Material 1 and Raw Material 28 is used to replace Raw Material 2, to obtain Intermediate 26-3 (yield 41%).

[0309] HRMS(ESI) m / z [M+H]+: Found: 446.14.

[0310] Synthesis of Intermediate 26-4: The synthesis is the same as that of Intermediate 4-2, except that Intermediate 26-3 is used to replace Intermediate 4-1, to obtain Intermediate 26-4 (yield 43%).

[0311] HRMS(ESI) m / z [M+H]+: Found: 410.12.

[0312] Synthesis of Intermediate 26-5: The synthesis is the same as that of Intermediate 4-3, except that Intermediate 26-4 is used to replace Intermediate 4-2, to obtain Intermediate 26-5 (yield 75%).

[0313] HRMS(ESI) m / z [M+H]+: Found: 502.10.

[0314] Preparation Example 1

[0315] Synthesis of Compound N1, and its synthetic route is as follows:

[0316]

[0317] The specific synthesis steps are as follows:

[0318] Take a 100 mL three-necked round-bottom flask, place a magnetic stir bar in it, connect a reflux condenser on top. After drying, fill it with nitrogen. Add intermediate 4-3 (10 mmol), raw material 3 (10 mmol), sodium bicarbonate (23 mmol), tetrakis(triphenylphosphine)palladium(0) (0.5 mmol), dichloro(di-tert-butyl(4-(dimethylamino)phenyl)phosphine)palladium(II) (0.5 mmol), toluene (25 mL), ethanol (7 mL) and water (7 mL) respectively, and displace the air with nitrogen three times. Under the protection of nitrogen, heat the mixture to 80 °C and react for 8 hours. After the reaction is completed, extract with ethyl acetate. The obtained extract is successively dried with magnesium sulfate, filtered and concentrated by rotary evaporation; the crude product is purified by chromatography (ethyl acetate:n-hexane (volume ratio 1:10)) to obtain compound N1 (yield 74%).

[0319] HRMS(ESI) m / z [M+H]+: Found: 567.11.

[0320] In the examples of the present invention, a total of 13 specific compounds (N1 to N13) connected by formula (1) and formula n-1 were synthesized. The synthesis methods of these compounds are the same as that of compound N1, and can be achieved by replacing the raw materials. Therefore, they are not listed one by one. Table 1 shows the raw materials used for the synthesis of N2 to N13, as well as the yields and test data of N2 to N13, as follows:

[0321] Table 1

[0322]

[0323]

[0324]

[0325] Synthesis of compound P1 in Preparation Example 2, and its synthetic route is as follows:

[0326]

[0327] The specific synthesis steps are as follows:

[0328] Add intermediate 6-2 (1 mmol), raw material 6 (1 mmol), Pd2(dba)3 (0.05 mmol), 50% tris(tert-butyl)phosphine solution (0.1 mmol), NaO t Bu (2.2 mmol), toluene (10 mL) into a 25 mL three-necked flask, and reflux and stir for 6 hours. After the reaction is completed, cool to room temperature, distill off the organic solvents under reduced pressure, and purify the crude product by chromatography (ethyl acetate:n-hexane (volume ratio 1:10)) to obtain compound P1 (yield 54%)

[0329] HRMS(ESI) m / z [M+H]+: Found: 578.27.

[0330] In the embodiments of the present invention, a total of 12 specific compounds (P1 to P12) connected by formula (1) and formula p-1 were synthesized. The synthesis methods of these compounds are the same as that of compound P1, and can be achieved by replacing raw materials. Therefore, they are not listed one by one. Table 2 shows the raw materials used for synthesizing P2, P4 to P11, as well as the yields and test data of P2, P4 to P11, as follows:

[0331] Table 2

[0332]

[0333]

[0334]

[0335] Device embodiments:

[0336] An organic electroluminescent device is provided in the embodiments of the present invention, which has the following layer structure: a substrate (an indium tin oxide (ITO) coated glass substrate as an anode coating) / a hole injection layer (HIL) / a hole transport layer (HTL) / a light emitting layer (EML) / an electron transport layer (ETL) / an electron injection layer (EIL), and finally a cathode.

[0337] The materials required for manufacturing the OLED are as follows, and all the following materials can be purchased through commercial channels or prepared by existing technologies:

[0338]

[0339] The preparation of the above organic electroluminescent device includes the following steps:

[0340] (1) Substrate cleaning: The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: glycol solvent ≤ 10 wt%, triethanolamine ≤ 1 wt%), rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol (volume ratio 1:1), baked in a clean environment until all moisture is removed, and then cleaned with ultraviolet light and ozone.

[0341] (2) Evaporating the organic light-emitting functional layer:

[0342] Place the above glass substrate with the anode layer in a vacuum chamber, evacuate to 1×10 -6 to 2×10 -4 Pa, and vacuum evaporate a mixture of HATCN and HT on the above anode layer film, where the mass ratio of HATCN to HT is 3:97, as the hole injection layer, and the evaporation thickness is 10 nm;

[0343] The hole transport layer (material: HT) is evaporated on the hole injection layer, and the evaporation film thickness is 80 nm;

[0344] The light-emitting layer is evaporated on the hole transport layer. The specific preparation method is as follows: The host material for light emission (the material is shown in Table 3) and the guest material (piq)2Ir(acac) are vacuum-evaporated in a co-evaporation manner, and the total evaporation film thickness is 30 nm;

[0345] An electron transport layer is evaporated on the electron buffer layer. The specific preparation method is as follows: ET and LiQ are vacuum-evaporated in a co-evaporation manner, and the total evaporation film thickness is 30 nm;

[0346] An electron injection layer (material: LiQ) is vacuum-evaporated on the electron transport layer, and the total evaporation film thickness is 1 nm;

[0347] Al is evaporated on the electron injection layer, and the total evaporation film thickness is 120 nm.

[0348] The parameters such as the layers, their materials, and thicknesses in the device are shown in Table 3.

[0349] Table 3

[0350]

[0351]

[0352]

[0353] Device performance test:

[0354] Instrument: The characteristics such as the current, voltage, luminance, and emission spectrum of the device are synchronously tested using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;

[0355] The test conditions for the organic light-emitting devices prepared in Examples 1-17 and Comparative Examples 1-2 are as follows:

[0356] (1) Photoelectric characteristic test conditions: The current density is 10 mA / cm 2 .

[0357] (2) Lifetime test: The current density is 20 mA / cm 2 , and the time (in hours) is recorded when the luminance of the device drops to 95% of the original luminance.

[0358] The test results are shown in Table 4.

[0359] Table 4

[0360]

[0361]

[0362] As can be seen from the test results in Table 4, compared with the comparative examples, the OLED device prepared from the organic electroluminescent compound provided by the present invention has a lower driving voltage (3.66 - 3.85 V), comparable or higher current efficiency (17 - 23 Cd / A), and longer lifespan (240 - 315 hours) at the same current density. Moreover, from the comparison between Example 1 and Example 16 or Example 17, it can be seen that compared with the compound connected by only Formula (1) and Formula n-1 or Formula p-1, the OLED device prepared by using the compound connected by Formula (1) and Formula n-1 and the compound connected by Formula (1) and p-1 simultaneously has a lower driving voltage, higher current efficiency, and longer lifespan. From the comparison between Example 1 and Example 14 or Example 15, it can be seen that by optimizing the ratio of the compound connected by Formula (1) and Formula n-1 and the compound connected by Formula (1) and p-1, the OLED device can have a longer lifespan.

[0363] The applicant declares that the present invention uses the above examples to illustrate the organic electroluminescent compound and the organic electroluminescent device containing the same of the present invention, but the present invention is not limited to the above examples, that is, it does not mean that the present invention must rely on the above examples to be implemented. Those skilled in the art should understand that any improvement to the present invention, the equivalent substitution of each raw material of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the protection scope and the disclosure scope of the present invention.

Claims

1. An organic electroluminescent compound, characterized in that, The organic electroluminescent compound has a structure shown in formula (1): wherein, Y 1 is selected from O or S; X 1 selected from N or CR X1 ,X 2 selected from N or CR X2 ,X 3 selected from N or CR X3 ,X 4 selected from N or CR X4 ,X 5 selected from N or CR X5 ,X 6 selected from N or CR X6 ,X 7 selected from N or CR X7 ,X 8 selected from N or CR X8 ,X 9 selected from N or CR X9 ,X 10 selected from N or CR X10 ,X 11 selected from N or CR X11 ,X 12 selected from N or CR X12 ; R X1 to R X12 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, one or at least two methylenes in the substituted C1-C30 alkyl being substituted with -O- or -S- in a non-adjacent manner to an O atom or an S atom, substituted or unsubstituted C2-C30 alkenyl, one or at least two methylenes in the substituted C2-C30 alkenyl being substituted with -O- or -S- in a non-adjacent manner to an O atom or an S atom, substituted or unsubstituted C7-C60 aralkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C4-C60 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 arylC3-C60 heteroarylamino, R X4 and R X5 or R X8 and R X9 form a ring, and the ring is And, R X1 ~R X4 、R X5 ~R X8 or R X9 ~R X12 Any two adjacent groups in combine to form ring A, where represents the fusion position; Y 5 selected from O or S; Y 2 selected from O or S; R 1 Selected from any one of hydrogen, deuterium, cyano group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, and substituted or unsubstituted C6-C30 aryloxy group.

2. The organic electroluminescent compound according to claim 1, characterized in that, The organic electroluminescent compound has a structure shown as follows: Among them, Y 1 , Y 2 , Y 5 are each independently selected from O or S; X 1 selected from N or CR X1 ,X 2 selected from N or CR X2 ,X 3 selected from N or CR X3 ,X 4 selected from N or CR X4 ,X 5 selected from N or CR X5 ,X 6 selected from N or CR X6 ,X 7 selected from N or CR X7 ,X 8 selected from N or CR X8 ,X 9 selected from N or CR X9 ,X 10 selected from N or CR X10 ,X 11 selected from N or CR X11 ,X 12 selected from N or CR X12 ; R X1 to R X12 each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, wherein one or at least two methylene groups in the substituted C1-C30 alkyl are replaced by -O- or -S- in a non-adjacent manner with respect to an O atom or an S atom, substituted or unsubstituted C2-C30 alkenyl, wherein one or at least two methylene groups in the substituted C2-C30 alkenyl are replaced by -O- or -S- in a non-adjacent manner with respect to an O atom or an S atom, substituted or unsubstituted C7-C60 aralkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C4-C60 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 arylC3-C60 heteroarylamino; R 1 selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, and substituted or unsubstituted C6-C30 aryloxy; Preferably, the Y 1 is O; Preferably, the Y 2 is O; Preferably, the Y 5 is O; Preferably, said R 1 is phenyl.

3. The organic electroluminescent compound according to any one of claims 1 or 2, characterized in that R X1 ~R X12 Any one or at least two of them are selected from the groups represented by formula n-1: Among them, represents the attachment position of the group, and L is selected from any one of a linking bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Z 1 selected from N or CR Z1 , Z 2 selected from N or CR Z2 , Z 3 selected from N or CR Z3 , Z 4 selected from N or CR Z4 , Z 5 selected from N or CR Z5 ; R Z1 -R Z5 Each independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, R Z1 -R Z5 Exist independently of each other, or R Z1 -R Z5 Two adjacent ones of them are connected to form a ring, and the ring is a benzene ring or a naphthalene ring; Alternatively, R X1 ~R X12 Any one or at least two of them are selected from the groups represented by formula p-1: Among them, represents the attachment position of the group, and L, L 1 , L 2 are each independently selected from any one of a linking bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar 1 、Ar 2 each independently selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl; Preferably, the R X1 is selected from formula n-1; Preferably, the R X2 is selected from formula n-1; Preferably, said R X3 is selected from formula n-1; Preferably, said R X4 is selected from formula n-1; Preferably, the R X5 is selected from formula n-1; Preferably, the R X6 is selected from formula n-1; Preferably, the R X7 is selected from Formula n-1; Preferably, the R X8 is selected from Formula n-1; Preferably, the R X9 is selected from formula n-1; Preferably, the R X10 is selected from formula n-1; Preferably, said R X11 is selected from formula n-1; Preferably, said R X12 is selected from formula n-1; Preferably, the R X1 is selected from formula p-1; Preferably, the R X2 is selected from formula p-1; Preferably, the R X3 is selected from formula p-1; Preferably, said R X4 is selected from formula p-1; Preferably, the R X5 is selected from formula p-1; Preferably, said R X6 is selected from formula p-1; Preferably, the R X7 is selected from formula p-1; Preferably, the R X8 is selected from formula p-1; Preferably, said R X9 is selected from formula p-1; Preferably, the R X10 is selected from formula p-1; Preferably, the R X11 is selected from formula p-1; Preferably, the R X12 is selected from Formula p-1.

4. The organic electroluminescent compound according to claim 3, characterized in that, The R Z1 -R Z5 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, bipyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl-substituted phenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl; Preferably, the Ar 1 and Ar 2 are each independently selected from any one of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, bipyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, dimethylfluorenyl, diphenylfluorenyl, benzyldimethylfluorenyl, spirobifluorenyl, benzocarbazolyl, benzonaphthofuranyl or benzonaphthothiophenyl.

5. The organic electroluminescent compound according to any one of claims 1-4, characterized in that In the formula n-1, Z 1 is selected from N, Z 5 is selected from N, Z 3 is selected from CR Z3 , Z 4 is selected from CR Z4 , Z 2 is selected from CR Z2 ; Preferably, Z 1 is selected from N, Z 3 is selected from N, Z 2 is selected from CR Z2 , Z 4 is selected from CR Z4 , Z 5 is selected from CR Z5 ; Preferably, Z 1 is selected from N, Z 3 is selected from N, Z 5 is selected from N, Z 4 is selected from CR Z4 , Z 2 is selected from CR Z2 ; Preferably, the formula n - 1 is selected from Preferably, the formula n - 1 is selected from Wherein, R Z1 -R Z5 each independently selected from hydrogen, deuterium, a substituted or unsubstituted group of any one of the following: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, bipyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl-substituted phenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl; Preferably, the group shown in formula n-1 is selected from any one of the following groups: Preferably, the group shown in formula p-1 is selected from any one of the following groups: Wherein the dotted line indicates the access position of the group.

6. The organic electroluminescent compound according to any one of claims 1-5, characterized in that, The organic electroluminescent compound is selected from any one of the following compounds:

7. The organic electroluminescent compound according to any one of claims 1-6, characterized in that, The organic electroluminescent compound is selected from any one of the following compounds:

8. A composition, characterized in that, The composition comprises the compound of claim 6 and / or the compound of claim 7; Preferably, the mass ratio of the compound of claim 6 to the compound of claim 7 is 1:9 - 9:1; Preferably, the mass ratio of the compound of claim 6 to the compound of claim 7 is 2:8 - 8:2; Preferably, the mass ratio of the compound of claim 6 to the compound of claim 7 is 3:7 - 7:3; Preferably, the mass ratio of the compound of claim 6 to the compound of claim 7 is 4:6 - 6:

4.

9. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, and the material of the organic layer comprises at least one of the organic electroluminescent compounds described in any one of claims 1 - 7; Preferably, the material of the organic layer comprises at least one of the compositions described in claim 8; Preferably, the organic layer includes a light-emitting layer, and the material of the light-emitting layer comprises at least one of the organic electroluminescent compounds described in any one of claims 1 - 7; Preferably, the organic layer includes a light-emitting layer, and the material of the light-emitting layer comprises at least one of the compositions described in claim 8; Preferably, the material of the light-emitting layer further comprises a transition metal complex; Preferably, the material of the light-emitting layer further comprises a complex containing Ir or Pt.

10. An electronic product, characterized in that, The electronic product comprises the organic electroluminescent device described in claim 9.

Images