A compound containing a heteroatom and an organic electroluminescent device thereof

Abstract

The application provides a compound containing a heteroatom and an organic electroluminescent device thereof, and belongs to the technical field of organic electroluminescence. The compound containing a heteroatom provided by the application is applied to an organic electroluminescent device as a covering layer material, and has good refractive index, so that the light extraction efficiency of the device can be effectively improved. Meanwhile, the compound has good absorption in the ultraviolet light band, can protect the device from damage to the organic layer material in the device caused by external light sources, and greatly improves the service life of the device. The compound containing a heteroatom and the organic electroluminescent device thereof have good application effect and industrialization prospect.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescence, in particular to a compound containing a heteroatom and an organic electroluminescence device thereof. BACKGROUND

[0002] Organic Light-Emitting Diode (OLED) has the advantages of high brightness, wide viewing angle, fast response speed, image stability, rich color of light emission, high resolution, low driving voltage, full solidification, ultra-thin and the like, and is widely used in mobile phones, digital video cameras, DVD players, personal digital assistants (PDA), notebook computers, car audio and televisions.

[0003] The OLED device has a sandwich structure, including electrode material film layers and organic functional materials sandwiched between different electrode film layers, and various different functional materials are stacked together according to the purpose to jointly form the OLED light-emitting device. The OLED generally comprises an anode, a cathode and an organic layer formed between the two electrodes. The organic layer of the OLED can comprise a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), an electron injection layer (EIL), a cover layer (CPL) and the like. Under the action of an external electric field, the holes injected from the anode and the electrons injected from the cathode (collectively referred to as carriers) migrate and recombine in the organic layer, and transfer energy to the light-emitting material, so that it is excited to form an exciton. When the exciton returns from the excited state to the ground state, it radiates and decays, and the decay energy is emitted in the form of light, thereby achieving the purpose of light emission.

[0004] The OLED device can be divided into three types according to the light emission direction: bottom emission device, top emission device and two-side emission device. In recent years, the top emission device has attracted the attention of researchers due to its advantages such as not being limited by pixel circuit and larger light-emitting area. Although the top emission device does not need to consider the influence of the pixel circuit on the light-emitting area, when the light emitted from the light-emitting layer of the light-emitting element is incident to other films, total reflection occurs at the interface between the ITO thin film and the glass substrate and the interface between the glass substrate and the air, which greatly limits the light extraction efficiency of the OLED device. Therefore, in order to improve the light extraction efficiency of the organic electroluminescence device and improve the service life of the device, a cover layer material with high refractive index, excellent thin film stability and good durability needs to be introduced. SUMMARY

[0005] In order to improve the luminous efficiency of an organic electroluminescent device and prolong the service life of the device, the present application provides a heteroatom-containing compound and an organic electroluminescent device thereof, the heteroatom-containing compound has good thermal stability and a high refractive index, and when the compound is applied to an organic electroluminescent device, the luminous efficiency of the device can be effectively improved, and the service life of the device can be prolonged.

[0006] The present application provides a heteroatom-containing compound, the heteroatom-containing compound has a structure as shown in chemical formula 1,

[0007]

[0008] At least one of Ar1 and Ar2 is selected from the structure shown in chemical formula 1-1, and the rest is selected from any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C25 heteroaryl group;

[0009]

[0010] X is selected from O or S;

[0011] Z is the same or different and is selected from N or CR1;

[0012] R1 is the same or different and is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 alicyclic group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C25 heteroaryl group, and a substituted or unsubstituted C3-C25 silyl group; when there are two or more R1, the two or more R1 are the same or different from each other, or two adjacent R1 are connected to each other to form a substituted or unsubstituted ring;

[0013] Ar3 is selected from the following structure,

[0014]

[0015] Y is selected from O or S;

[0016] U is the same or different and is selected from CH or N;

[0017] R2 and R3 are the same or different and are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 alicyclic group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C25 heteroaryl group, and a substituted or unsubstituted C3-C25 silyl group;

[0018] b, c are the same or different and selected from 0, 1, 2, 3 or 4; when two or more R2s exist, the two or more R2s are the same or different from each other, or two adjacent R2s are connected to each other to form a substituted or unsubstituted ring; when two or more R3s exist, the two or more R3s are the same or different from each other, or two adjacent R3s are connected to each other to form a substituted or unsubstituted ring, wherein at least one of R2 and R3 is connected to each other to form a substituted or unsubstituted ring;

[0019] L1, L2, L3 are the same or different and selected from any one or a combination of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C25 heteroarylene group, a substituted or unsubstituted C3-C12 alicyclic group and a C6-C30 aryl group.

[0020] The present application also provides an organic electroluminescent device comprising an anode, a cathode and one or more organic layers disposed between or outside the anode and the cathode, wherein the organic layers comprise any one or a combination of at least two of the compounds containing heteroatoms.

[0021] The present application has the following advantages:

[0022] The compound containing heteroatoms provided by the present application has a good refractive index, can effectively improve the light extraction efficiency of the device, improve the light-emitting efficiency of the device, and has a good absorption in the ultraviolet light band. When the compound is applied to an organic electroluminescent device as a cover layer material, the device can be protected from damage to the organic layer material in the device caused by external light sources, greatly improving the service life of the device. DETAILED DESCRIPTION

[0023] In order to make the objects, technical solutions and advantages of the embodiments of the present application clearer, the technical solutions of the embodiments of the present application will be described clearly and completely below in combination with the embodiments of the present application. Obviously, the described embodiments are part of the embodiments of the present application, rather than all the embodiments. And in the case of no conflict, the embodiments in the present application and the features in the embodiments can be combined with each other. Based on the described embodiments of the present application, all other embodiments obtained by those of ordinary skill in the art without creative labor fall within the scope of protection of the present application.

[0024] Unless otherwise defined, technical terms or scientific terms used in the present application shall have the usual meaning understood by those of ordinary skill in the art to which the present application belongs.

[0025] In the compounds of the present application, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms in both their natural isotopic abundance and non-natural abundance.

[0026] In the present specification, “*-” means a moiety connected to another substituent.

[0027] In the present specification, when the position of a substituent on a ring is not fixed, it means that it can be connected to any one of the corresponding optional sites of the ring.

[0028] For example, may mean may mean may mean and so on.

[0029] In the present specification, when a substituent or a connecting site is through a bond between two or more rings, it means that it can be connected to any one of the two or more rings, and specifically, it can be connected to any one of the corresponding optional sites of the ring. For example may mean may mean may mean and so on.

[0030] The halogen in the present application refers to fluorine, chlorine, bromine, iodine;

[0031] The alkyl in the present application refers to a monovalent group obtained by removing one hydrogen atom from an alkane molecule, which can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, preferably 1 to 12 carbon atoms, more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 6 carbon atoms, and examples can include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl, hexyl, and the like, but are not limited thereto.

[0032] The alicyclic group in the present application refers to a monovalent group obtained by removing one hydrogen atom from an alicyclic hydrocarbon molecule, which can be a cycloalkyl group or a cycloalkenyl group, preferably having 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms, and examples can include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like, but are not limited thereto.

[0033] The aryl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from the nucleus carbon of an aromatic hydrocarbon molecule, which can be a monocyclic aryl group, a polycyclic aryl group or a fused ring aryl group, preferably having 6 to 30 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms, and examples can include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, an indenyl group, a dihydroindenyl group, a dihydronaphthyl group, a tetrahydronaphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a triphenylenyl group, a perylenyl group, etc., but are not limited thereto.

[0034] The heteroaryl group according to the present application refers to a general term of a monovalent group obtained by removing one hydrogen atom from the nucleus carbon of an aromatic heterocycle composed of carbon and a heteroatom, which can be one or more of N, O and S, which can be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a fused ring heteroaryl group, preferably having 3 to 30 carbon atoms, preferably 3 to 22 carbon atoms, more preferably 3 to 16 carbon atoms, and most preferably 3 to 8 carbon atoms, and examples can include a pyridyl group, a pyrimidinyl group, a triazinyl group, a pyrazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalyl group, a quinazolyl group, a naphthrydinyl group, a furanyl group, a thiophenyl group, a pyrrolyl group, a benzofuranyl group, a benzothiophenyl group, an indolyl group, a pyridofuranyl group, a pyridothiophenyl group, a pyridopyrrolyl group, a pyrimidofuranyl group, a pyrimidothiophenyl group, a naphthofuranyl group, a naphthothiophenyl group, a phenanthrofuranyl group, a phenanthrothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, an oxazolyl group, a thiazolyl group, an imidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzimidazolyl group, a naphthoxazolyl group, a naphthothiazolyl group, a naphthimidazolyl group, a phenanthrooxazolyl group, a phenanthrothiazolyl group, a pyridoxazolyl group, a pyridothiazolyl group, an azacarbazolyl group, a quinoxazolyl group, a quinazothiazolyl group, a quinazimidazolyl group, etc., but are not limited thereto.

[0035] In the present specification, the "substituted or unsubstituted silyl group" refers to a —Si(R k )3 group, in which each R k is the same or different from each other and is selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic ring and C6-C60 aromatic ring fused ring group, and a substituted or unsubstituted C3-C30 alicyclic ring and C2-C60 heteroaromatic ring fused ring group. Preferably, each R kthe same or different groups selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. Preferably, each R k the same or different groups selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl. The C3-C25 in the "substituted or unsubstituted C3-C25 silyl group" means the total number of carbon atoms of C1-C30 alkyl, C3-C30 cycloalkyl, C6-C60 aryl, C2-C60 heteroaryl, C3-C30 alicyclic ring and C6-C60 aromatic ring fused ring group, C3-C30 alicyclic ring and C2-C60 heteroaromatic ring fused ring group, which are connected to Si. Examples of the substituted or unsubstituted silyl group such as substituted or unsubstituted C3-C25 silyl group can include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyl-t-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, trilysylsilyl, and the like, but are not limited thereto.

[0036] The arylene group according to the present application means a divalent group in which two hydrogen atoms are removed from the carbon of the aromatic nucleus of an aromatic hydrocarbon molecule. They can apply the above-described explanation of the aryl group except that they are divalent groups, respectively.

[0037] The heteroarylene group according to the present application means a divalent group in which two hydrogen atoms are removed from the carbon of the aromatic nucleus of an aromatic heterocycle composed of carbon and heteroatoms. They can apply the above-described explanation of the heteroaryl group except that they are divalent groups, respectively.

[0038] The fused ring group of the alicyclic and aromatic ring according to the present application refers to a total of alicyclic and aromatic rings fused together and then removing one hydrogen atom, leaving a monovalent group. Preferably, it has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, and examples can include benzo-cyclopropyl, benzo-cyclobutyl, benzo-cyclopentyl, benzo-cyclohexyl, benzo-cycloheptyl, benzo-cyclopentenyl, benzo-cyclohexenyl, benzo-cycloheptenyl, naphtho-cyclopropyl, naphtho-cyclobutyl, naphtho-cyclopentyl, naphtho-cyclohexyl, and the like, but are not limited thereto. The "substituted" according to the present application means that a hydrogen atom in a group of a compound is replaced with another atom or group, and the position of substitution is not limited.

[0039] The "substituted or unsubstituted" according to the present application means unsubstituted or substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a halogen atom, an amino group, a nitro group, a substituted or unsubstituted C1-C25 alkyl group, a substituted or unsubstituted C3-C30 alicyclic group, a substituted or unsubstituted C1-C25 heterocyclic alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted fused ring group of C3-C30 alicyclic and C6-C30 aromatic rings, a substituted or unsubstituted fused ring group of C1-C25 heterocyclic alkyl and C6-C30 aromatic rings, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted fused ring group of C3-C25 alicyclic and C2-C30 heteroaryl rings, a substituted or unsubstituted C6-C30 arylamine group, a substituted or unsubstituted C6-C30 aryloxy group, preferably hydrogen, deuterium, tritium, a halogen atom, a cyano group, a C1-C12 alkyl group, a C3-C18 alicyclic group, a C6-C25 aryl group, a C2-C25 heteroaryl group, and specific examples can include hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, a cyano group, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a benzo-cyclobutyl group, a benzo-cyclopentyl group, a benzo-cyclohexyl group, a benzo-cyclopentenyl group, a benzo-cyclohexenyl group, a trifluoromethyl group, a phenyl group, a tolyl group, a mesityl group, a penta-deuterated phenyl group, a penta-fluorophenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a benzophenanthryl group, a pyrenyl group, a triphenylenyl group, phenyl, naphthyl, anthryl, pyrenyl, perylenyl, fluoranthenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, carbazolyl, 9-phenylcarbazolyl, spirobifluorenyl, carbazoloindolyl, pyrrolyl, furanyl, thienyl, indolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzimidazolyl, pyridyloxazolyl, pyridylthiazolyl, pyridylimidazolyl, pyrimidyloxazolyl, pyrimidyithiazolyl, pyrimidyimidazolyl, quinolyl, isoquinolyl, quinolyloxazolyl, quinolyithiazolyl, quinolyimidazolyl, phenothiazyl, phenoxazyl, acridyl, and the like, but are not limited thereto. Alternatively, when the substituent is two or more, adjacent substituents can be bonded to form a ring; when the substituent is two or more, two or more substituents can be the same as or different from each other.

[0040] In the present application, "two adjacent groups are linked to form a ring" means that the adjacent groups are bonded to each other and optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocyclic ring can include an aliphatic heterocyclic ring or an aromatic heterocyclic ring. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocyclic ring can be a saturated aliphatic heterocyclic ring or an unsaturated aliphatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring can be a monocyclic group or a polycyclic group. In addition, the ring formed by the bonding of the adjacent groups can be connected to another ring to form a spiro structure. Examples are as follows:

[0041]

[0042] In the present specification, the ring formed by the bonding can be an aromatic ring or a non-aromatic ring, and can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a fused ring, or the like, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornane, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, and the like, but are not limited thereto.

[0043] The following describes embodiments of the organic electroluminescent device according to the present application, but the embodiments of the present application can be modified into other modes, and the scope of the present application is not limited by the embodiments described below.

[0044] In describing the structural elements of the present application, the terms "comprise" or "include" and similar terms used in the present application mean that the device or element preceding the term encompasses the device or element listed after the term and equivalents thereof, without excluding other devices or elements. The terms "connect" or "connected" or similar terms do not limit to physical or mechanical connections, but can include electrical connections, whether direct or indirect. The terms "inner", "outer", "upper", "lower", and the like are used to describe a relative position in only one orientation to indicate only one orientation, and when the absolute position of the structural elements described is changed, the relative position relationship can also be changed accordingly. Also, in the case where a structural element such as a layer, a film, a region, and a plate is "on" another structural element, it can be understood not only as "directly on" the other structural element, but also as "with another structural element interposed therebetween". Conversely, in the case where a structural element is "directly on" another structural element, it can be understood that there is no other structural element interposed therebetween.

[0045] In the present application, "at least one" includes one, two, three, or more.

[0046] In the present application, "one or more" includes one, two, three, four, five, six, seven, eight, nine, ten, or more.

[0047] The present application provides a compound containing a heteroatom, the compound containing a heteroatom having a structure as shown in Chemical Formula 1,

[0048]

[0049] At least one of Ar1 and Ar2 is selected from the structure shown in Chemical Formula 1-1, and the rest is selected from any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C25 heteroaryl group;

[0050]

[0051] X is selected from O or S;

[0052] z is the same or different and is selected from N or CR1;

[0053] R1 is the same or different and is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 alicyclic group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C25 heteroaryl group, a substituted or unsubstituted C3-C25 silyl group; when two or more R1 are present, two or more R1 are the same as or different from each other, or two adjacent R1 are connected to each other to form a substituted or unsubstituted ring;

[0054] Ar3is selected from the group consisting of structures shown below,

[0055]

[0056] Y is selected from O or S;

[0057] u is the same or different and is selected from CH or N;

[0058] R2, R3are the same or different and are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C25 heteroaryl group, substituted or unsubstituted C3-C25 silyl group;

[0059] b, c are the same or different and are selected from 0, 1, 2, 3 or 4; when two or more R2are present, two or more R2are the same or different from each other, or two adjacent R2are connected to each other to form a substituted or unsubstituted ring; when two or more R3are present, two or more R3are the same or different from each other, or two adjacent R3are connected to each other to form a substituted or unsubstituted ring, wherein at least one of R2, R3is connected to each other to form a substituted or unsubstituted ring;

[0060] L1, L2, L3are the same or different and are selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C25 heteroarylene, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aryl ring fused ring group, or a combination thereof.

[0061] Preferably, Ar1is selected from the structure shown in Chemical Formula 1-1;

[0062] Preferably, Ar2is selected from the structure shown in Chemical Formula 1-1;

[0063] Preferably, Ar1and Ar2are selected from the structure shown in Chemical Formula 1-1;

[0064] Preferably, Chemical Formula 1-1 is selected from the group consisting of structures shown below,

[0065]

[0066] R1is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0067] R1may be substituted by one or more substituents, which are the same or different, selected from any one of deuterium, halogen, cyano, trifluoromethyl, methyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, trimethylsilyl, triphenylsilyl; when there are two or more substituents, the two or more substituents are the same or different from each other;

[0068] a1is selected from 0, 1, 2 or 3; a2is selected from 0, 1, 2, 3 or 4; a3is selected from 0, 1 or 2; a4is selected from 0, 1, 2, 3, 4 or 5; a5is selected from 0, 1, 2, 3, 4, 5 or 6; a6is selected from 0, 1, 2, 3, 4, 5, 6 or 7; a7is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R1, the two or more R1are the same or different from each other.

[0069] Preferably, Ar3is selected from any one of the following structures,

[0070]

[0071]

[0072] Y is selected from O or S;

[0073] R2, R3are the same or different and are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0074] R2, R3may be substituted by one or more substituents, which are the same or different, selected from any one of deuterium, halogen, cyano, trifluoromethyl, methyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, trimethylsilyl, triphenylsilyl; when there are two or more substituents, the two or more substituents are the same or different from each other;

[0075] b1 is selected from 0, 1, 2 or 3; b2 is selected from 0, 1, 2, 3 or 4; b3 is selected from 0, 1, 2, 3, 4, 5 or 6; b4 is selected from 0, 1, 2, 3, 4 or 5; b5 is selected from 0, 1 or 2; when there are two or more R2, the two or more R2 are the same or different from each other;

[0076] c1 is selected from 0, 1, 2, 3, 4, 5 or 6; c2 is selected from 0, 1, 2, 3, 4 or 5; c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; c4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; c5 is selected from 0, 1, 2, 3 or 4; when there are two or more R3, the two or more R3 are the same or different from each other.

[0077] Preferably, at least one of Ar1, Ar2 is selected from the structure shown in Chemical Formula 1-1, and the rest is selected from any one of the structures shown below,

[0078] v is the same or different selected from N or CH;

[0079] E1, E3, E4, E5 are the same or different selected from any one of O, S, CR5R6, NR7;

[0080] E2 is selected from CR8 or N;

[0081] R7 is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C25 silyl group;

[0082] R4, R5, R6, R8 are the same or different selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C25 silyl group;

[0083] d1 is selected from 0, 1, 2, 3, 4 or 5; d2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R4, the two or more R4 are the same or different from each other, or two adjacent R4 are connected to each other to form a substituted or unsubstituted ring.

[0084] Preferably, at least one of Ar1 and Ar2 is selected from the structure shown in Formula 1-1, and the rest is selected from any one of the structures shown below,

[0085]

[0086]

[0087] E1, E3, E4 and E5 are the same or different and are selected from any one of O, S, CR5R6 and NR7;

[0088] E2 is selected from CR8 or N;

[0089] R7 is selected from any one of methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, diphenofuranyl, diphenothienyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0090] R4, R5, R6, R8are the same or different and are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, pyridazyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0091] R4, R5, R6, R7, R8may be substituted by one or more substituents selected from any one or combination of hydrogen, deuterium, cyano, halogen, trifluoromethyl, C1-C12 alkyl, C3-C12 alicyclyl, C6-C18 aryl, C2-C25 heteroaryl, substituted or unsubstituted C3-C25 silyl; when there are two or more substituents, the two or more substituents are the same or different from each other;

[0092] d1 is selected from 0, 1, 2, 3, 4 or 5; d2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; d6 is the same or different and is selected from 0, 1, 2, 3 or 4; d7 is selected from 0, 1, 2 or 3; d8 is selected from 0, 1 or 2; d9 is selected from 0, 1, 2, 3, 4, 5 or 6; d 10 d10 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; d 11 d11 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; when there are two or more R4, the two or more R4 are the same or different from each other.

[0093] Preferably, at least one of Ar1, Ar2 is selected from the structure shown in Chemical Formula 1-1, and the rest is selected from any one of the structures shown below,

[0094]

[0095]

[0096] E1, E3, E4, E5 are the same or different and are selected from any one of O, S, CR5R6, NR7;

[0097] R7is selected from any one of methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0098] R4, R5, R6are the same or different and are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0099] R4, R5, R6, R7may be substituted by one or more substituents selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl; when there are two or more substituents, the two or more substituents are the same or different from each other.

[0100] Preferably, L1, L2, L3are the same or different and are selected from a single bond or any one of the following structures,

[0101]

[0102]

[0103] said Rb, Rc are the same or different selected from any one or combination of hydrogen, deuterium, cyano, halogen, trifluoromethyl, C1-C12 alkyl, C3-C12 alicyclyl, C6-C18 aryl, C2-C25 heteroaryl;

[0104] said Rd is selected from any one or combination of C1-C12 alkyl, C3-C12 alicyclyl, C6-C18 aryl, C2-C25 heteroaryl;

[0105] said R9 are the same or different selected from any one of hydrogen, deuterium, cyano, halogen, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl;

[0106] said e1 are the same or different selected from 0, 1, 2, 3 or 4; said e2 are the same or different selected from 0, 1, 2, 3, 4, 5 or 6; said e3 are the same or different selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e4 are the same or different selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said e5 are the same or different selected from 0, 1, 2 or 3; said e6 are the same or different selected from 0, 1 or 2; said e7 are the same or different selected from 0, 1, 2, 3, 4 or 5; said e8 are the same or different selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R9, the two or more R9 are the same or different from each other, or two adjacent R9 form a substituted or unsubstituted ring.

[0107] Preferably, said Rb, Rc, R9 are the same or different selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, diphenofuranyl, diphenothienyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0108] Rb, Rc, R9may be substituted with one or more substituents selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl; when there are two or more substituents, the two or more substituents are the same as or different from each other.

[0109] Preferably, Rd is selected from any one of methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0110] Rdmay be substituted with one or more substituents selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl; when there are two or more substituents, the two or more substituents are the same as or different from each other.

[0111] Preferably, the compound containing a heteroatom is selected from any one of the following structures,

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131] The present application also provides a method for preparing a compound containing a heteroatom, but the method for preparing the present application is not limited thereto. The core structure of Formula 1 can be prepared by the following reaction scheme:

[0132]

[0133] The Xa is the same or different and is selected from any one of Cl, Br, and I.

[0134] The above substituents can be bonded by a method known in the art, and the type and position of the substituents or the number of the substituents can be changed according to a technique known in the art.

[0135] The present application provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers disposed between or outside the anode and the cathode, the organic layers comprising one or a combination of at least two of the heteroatom-containing compounds described in the present application.

[0136] Preferably, the organic layers described in the present application comprise a capping layer, the capping layer comprising one or a combination of at least two of the heteroatom-containing compounds described in the present application.

[0137] The organic layers described in the present application can further include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron injection layer, an electron transport layer, a hole blocking layer, an encapsulating layer, etc. However, the structure of the organic electroluminescent device of the present application is not limited by the above-described structure, and if necessary, one or more organic layers can be omitted or simultaneously provided, and organic layers having the same function can be provided in a stacked structure of two or more layers.

[0138] The organic electroluminescent device described in the present application preferably has the following structure:

[0139] substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode / capping layer;

[0140] substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode / capping layer;

[0141] substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode / capping layer;

[0142] substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode / capping layer;

[0143] substrate / anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capping layer;

[0144] substrate / anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capping layer;

[0145] substrate / anode / hole injection layer / hole transport layer / light-emitting auxiliary layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capping layer;

[0146] However, the structure of the organic electroluminescent device is not limited thereto. The organic electroluminescent device described in the present application can be selected and combined according to the requirements of the device parameters and the characteristics of the materials, and one or more organic layers can be added or omitted, and organic layers having the same function can be provided in a stacked structure of two or more layers.

[0147] The organic electroluminescent device of the present application is generally formed on a substrate. The substrate is not particularly limited as long as it does not change when forming electrodes and organic layers, and examples thereof include glass, plastic, a polymer film, silicon, and the like.

[0148] In the organic electroluminescent device of the present application, the anode material preferably uses a high work function material capable of promoting hole injection into the organic layer. Specific examples of the anode material that can be used in the present application can include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ITO-Ag-ITO; conductive polymers such as poly(3-methylthiophene), polypyrrole, polyaniline, poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), and the like, but are not limited thereto.

[0149] In the organic electroluminescent device of the present application, the hole injection material preferably has a material having good hole accepting ability. Specific examples of the hole injection material that can be used in the present application can include metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide, phthalocyanine compounds, diphenylamine compounds, phenazine compounds, and the like, such as copper phthalocyanine (CuPc), titanium phthalocyanine oxide, N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamine)phenyl]diphenylamine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)diphenylamine (MeO-TPD), diquinoxalino[2,3-a:2',3'-c]phenazine (HATNA), 4,4',4"-tris[2-naphthylphenylamino]triphenylamine (2T-NATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), and the like, but are not limited thereto.

[0150] The hole transport material preferably has excellent hole transport properties and a HOMO level matched with the anode material in the organic electroluminescent device according to the present application. Specific examples of the hole transport material that can be used in the present application can include diphenylamine-based compounds, triphenylamine-based compounds, fluorene-based compounds, and carbazole-based compounds, such as N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-di(naphthalen-1-yl)-N,N'-di(phenyl)-2,2'-dimethylphenylamine (a-NPD), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4-[1-[4-[di(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)aniline (TAPC), and the like, but are not limited thereto.

[0151] The light-emitting auxiliary layer preferably has good hole transport properties and electron blocking properties in the organic electroluminescent device according to the present application. Specific examples of the light-emitting auxiliary material that can be used in the present application can include triarylamine derivatives, spirofluorene derivatives, furan derivatives, and the like, such as TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenyl N4'-[1,1':4',1"-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-biphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirobifluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, and the like, but are not limited thereto.

[0152] The organic electroluminescent device of the present application comprises a light-emitting layer material, which comprises a light-emitting layer host material and a light-emitting layer dopant material. The light-emitting layer host material can be selected from 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9,10-di(2-naphthyl)anthracene (ADN), 4,4-bis(9-carbazolyl)-biphenyl (CPB), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), 9,10-di(1-naphthyl)anthracene (a-ADN), N,N'-di-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1":4",1"'-quaterphenyl]-4,4"-diamine (4PNPB), 1,3,5-tris(9-carbazolyl)benzene (TCP), and the like, but not limited thereto. Preferably, the light-emitting layer host material of the present application is selected from 9,10-di(2-naphthyl)anthracene (ADN), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), 9,10-di(1-naphthyl)anthracene (a-ADN), and the like. The light-emitting layer dopant material can be selected from (6-(4-(diphenylamino(phenyl)-N,N-diphenylpyrene-1-amine) (DPAP-DPPA), 2,5,8,11-tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), bis(2-hydroxyphenylpyridine)beryllium (Bepp2), bis(4,6-difluorophenylpyridine-C2,N)picolinate iridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(2-phenylpyridine)acetylacetonate iridium (Ir(ppy)2(acac)), 9,10-di[N-(p-tolyl)anilino]anthracene (TPA), 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), tris[1-phenylisoquinoline-C2,N]iridium(III) (Ir(piq)3), bis(1-phenylisoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), and the like, but not limited thereto. Preferably, the light-emitting layer dopant of the present application is selected from 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe), 9,10-di[N-(p-tolyl)anilino]anthracene (TPA), 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), and the like.

[0153] The doping ratio of the light-emitting layer host material and the light-emitting layer dopant material is preferably different according to the materials used, and the light-emitting layer dopant material is usually doped at a ratio of 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0154] In the organic electroluminescent device, the hole blocking material has a strong hole blocking ability and a suitable HOMO and LUMO energy level. In the present application, specific examples of the hole blocking material that can be used include imidazole, triazole, phenanthroline derivatives, and the like, such as 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol) aluminum(III) (BAlq), and the like, but are not limited thereto.

[0155] In the organic electroluminescent device, the electron transport material preferably has a strong electron-accepting ability and a low HOMO and LUMO energy level. In the present application, specific examples of the electron transport material that can be used include imidazole, triazole, phenanthroline derivatives, quinoline, and the like, such as 2,9-(dimethyl)-4,7-biphenyl-1,10-phenanthroline (BCP), 1,3,5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), 4,4'-bis(4,6-diphenyl-1,3,5-triazinyl) biphenyl (BTB), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 2-(naphthalen-2-yl)-4,7-(diphenyl)-1,10-phenanthroline (HNBphen), 8-hydroxyquinoline-lithium (LiQ), and the like, but are not limited thereto.

[0156] In the organic electroluminescent device, the electron injection material preferably has a small potential barrier to the adjacent organic transport material or host material, and has an effect of injecting electrons from the cathode. Examples of the electron injection material that can be used in the present application include alkali metal salts (such as LiF, CsF), alkaline earth metal salts (such as MgF2), metal oxides (such as Al2O3, MoO3), but are not limited thereto.

[0157] In the organic electroluminescent device according to the present application, a cathode material preferably uses a low work function material capable of promoting electron injection into an organic layer. Specific examples of the cathode material usable in the present application can include metals such as aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof; multilayer metal materials such as LiF / Al, Mg / Ag, Li / Al, LiO2 / Al, BaF2 / Al, and the like, but are not limited thereto.

[0158] In the organic electroluminescent device according to the present application, a cathode material preferably uses a low work function material capable of promoting electron injection into an organic layer. Specific examples of the cathode material usable in the present application can include metals such as aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof; multilayer metal materials such as LiF / Al, Mg / Ag, Li / Al, LiO2 / Al, BaF2 / Al, and the like, but are not limited thereto.

[0159] The thickness of each organic layer of the organic electroluminescent device according to the present application is not particularly limited, and a thickness commonly used in the art can be used.

[0160] The organic electroluminescent device according to the present application can be prepared by any one of vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer printing, electro-spray coating, slit coating, and dip coating, and the vacuum evaporation is preferred in the present application.

[0161] The organic electroluminescent device according to the present application can be widely used in the fields of panel display, illumination light source, flexible OLED, electronic paper, organic solar cell, organic photoreceptor or organic thin film transistor, signboard, signal lamp, and the like.

[0162] The present application will be explained more specifically by the following examples, but the present application is not intended to be limited by the examples. Based on the description, those skilled in the art will be able to implement the present application and prepare other compounds and devices according to the present application within the entire scope disclosed without any creative effort.

[0163] Preparation and characterization of compounds

[0164] Explanation of raw materials, reagents, and characterization equipment:

[0165] The present application does not have a particular limitation on the source of raw materials and reagents used in the following examples, and they can be commercially available products or prepared by a preparation method well known to those skilled in the art.

[0166] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer in chloroform as a solvent.

[0167] Elemental analysis was performed using a Vario EL cube elemental analyzer from Elementar, Germany, with a sample mass of 5-10 mg; Synthesis Example 1: Preparation of Intermediate C-328:

[0168]

[0169] Under nitrogen protection, a-328 (28.87 g, 150.00 mmol), b-328 (24.59 g, 150.00 mmol), K2CO3 (34.55 g, 250 mmol) and 750 mL mixed solvent (toluene: ethanol: water = 2: 1: 1) were sequentially added to a reaction bottle, and after replacing the air with nitrogen three times, Pd(PPh3)4 (1.73 g, 1.5 mmol) was added, and the reaction was stirred at reflux temperature for 4 h. After the reaction was completed, it was cooled to room temperature, filtered to obtain a filter cake, and the filter cake was washed with ethanol, and finally the filter cake was recrystallized with toluene: ethanol = 10:3 to obtain intermediate C-328 (27.10 g, yield 78%), HPLC purity ≧ 99.83%. Mass spectrum m / z: 231.0145 (theoretical value: 231.0199).

[0170] Synthesis Example 2: Preparation of Intermediate C-400:

[0171]

[0172] According to the same preparation method as Synthesis Example 1, a-328, b-328 were replaced with equimolar a-400, b-400 to obtain intermediate C-400 (33.40 g), HPLC purity ≧ 99.81%. Mass spectrum m / z: 282.0374 (theoretical value: 282.0308).

[0173] Synthesis Example 3: Preparation of Intermediate C-428:

[0174]

[0175] According to the same preparation method as Synthesis Example 1, a-328, b-328 were replaced with equimolar a-428, b-428 to obtain intermediate C-428 (31.97 g), HPLC purity ≧ 99.85%. Mass spectrum m / z: 250.0249 (theoretical value: 250.0270).

[0176] Synthesis Example 4: Preparation of Intermediate C-597:

[0177]

[0178] Following the same preparation method as in Synthesis Example 1, a-328, b-328 were replaced with equimolar of a-597, b-597 to obtain intermediate C-597 (32.36 g) with HPLC purity ≧ 99.86%. Mass spectrum m / z: 299.0012 (calcd: 299.0073).

[0179] Synthesis Example 5: Preparation of compound 3:

[0180]

[0181] Synthesis intermediate D-3

[0182] Under nitrogen protection, A-5 (23.33 g, 100.00 mmol), B-3 (30.92 g, 100.00 mmol), NaOt-Bu (14.42 g, 150.00 mmol) were dissolved in 600 ml of toluene solvent, Pd(OAc)2(0.17 g, 1.00 mmol), P(t-Bu)3(4.00 mL of 0.5M toluene solution, 2.00 mmol) were added under stirring, and the mixture of the above reactants was heated to reflux for 4 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, allowed to stand and separate, the organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure, and the crystals were precipitated by cooling, filtered, and the obtained solid was recrystallized with toluene:methanol=8:2 to obtain intermediate D-3 (36.93 g, yield 80%) with HPLC purity ≧ 99.87%. Mass spectrum m / z: 461.1725 (calcd: 461.1780).

[0183] Synthesis compound 3

[0184] Under nitrogen protection, intermediate D-3 (23.08 g, 50.00 mmol), C-3 (13.76 g, 50.00 mmol), NaOt-Bu (7.69 g, 80 mmol) were dissolved in 500 ml of toluene solvent, Pd2(dba)3(0.48 g, 0.50 mmol), X-Phos (0.38, 0.75 mmol) were added under stirring, and the mixture of the above reactants was heated to reflux for 5.5 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, allowed to stand and separate, the organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure, and the crystals were precipitated by cooling, filtered, and the obtained solid was recrystallized with toluene to obtain compound 3 (27.21 g, yield 83%) with HPLC purity ≧ 99.97%. Mass spectrum m / z: 655.2281 (calcd: 655.2260). Theoretical elemental content (%) 46 H 29N3O2: C, 84.25; H, 4.46; N, 6.41. Found (mass %): C, 84.21; H, 4.45; N, 6.46. Synthesis Example 6: Preparation of Compound 16:

[0185]

[0186] According to the same preparation method as in Synthesis Example 5, A-3, B-3, C-3 were replaced with equimolar A-16, B-16, C-16 to obtain Compound 16 (27.09 g) with HPLC purity > 99.95%. Mass spectrum m / z: 685.2642 (theoretical value: 685.2636). Theoretical elemental content (%) C 48 H 23 D6N3O2: C, 84.06; H, 5.14; N, 6.13. Found (mass %): C, 84.07; H, 5.14; N, 6.12.

[0187] Synthesis Example 7: Preparation of Compound 28:

[0188]

[0189] According to the same preparation method as in Synthesis Example 5, A-3, B-3, C-3 were replaced with equimolar A-28, B-28, C-16 to obtain Compound 28 (27.09 g) with HPLC purity > 99.95%. Mass spectrum m / z: 685.2642 (theoretical value: 685.2636). Theoretical elemental content (%) C 48 H 23 D6N3O2: C, 82.88; H, 4.35; N, 7.25. Found (mass %): C, 82.85; H, 4.36; N, 7.27.

[0190] Synthesis Example 8: Preparation of Compound 46:

[0191]

[0192] According to the same preparation method as in Synthesis Example 5, A-3, B-3, C-3 were replaced with equimolar A-28, B-46, C-46 to obtain Compound 46 (27.77 g) with HPLC purity > 99.99%. Mass spectrum m / z: 645.1884 (theoretical value: 645.1875). Theoretical elemental content (%) C 44 H 27 N3OS: C, 81.84; H, 4.21; N, 6.51. Found (mass %): C, 81.84; H, 4.22; N, 6.50.

[0193] Synthesis Example 9: Preparation of compound 51:

[0194]

[0195] Following the same preparation method as in synthesis example 5, A-3, B-3, C-3 were replaced with equimolar of A-51, B-46, C-16 to give compound 51 (24.75 g) with HPLC purity > 99.96%. Mass spectrum m / z: 630.2026 (calcd 630.2056). Calcd. element content (%) C 43 H 26 N4O2: C, 81.89; H, 4.16; N, 8.88. Found element content (%) C, 81.83; H, 4.18; N, 8.92.

[0196] Synthesis Example 10: Preparation of compound 57:

[0197]

[0198] Following the same preparation method as in synthesis example 5, A-3, B-3, C-3 were replaced with equimolar of A-28, B-57, C-46 to give compound 57 (25.46 g) with HPLC purity > 99.97%. Mass spectrum m / z: 669.1842 (calcd 669.1875). Calcd. element content (%) C 46 H 27 N3OS: C, 82.49; H, 4.06; N, 6.27. Found element content (%) C, 82.48; H, 4.08; N, 6.26.

[0199] Synthesis Example 11: Preparation of compound 66:

[0200]

[0201] Following the same preparation method as in synthesis example 5, A-3, B-3, C-3 were replaced with equimolar of A-51, B-66, C-66 to give compound 66 (27.52 g) with HPLC purity > 99.96%. Mass spectrum m / z: 696.1928 (calcd 696.1984). Calcd. element content (%) C 47 H 28 N4OS: C, 81.01; H, 4.05; N, 8.04. Found element content (%) C, 81.03; H, 4.04; N, 8.03.

[0202] Synthesis Example 12: Preparation of compound 72:

[0203]

[0204] Following the same preparation procedure as in Synthesis Example 5, substituting A-3, B-3, C-3 with equimolar of A-28, B-72, C-72, compound 72 (23.31 g) was obtained, HPLC purity > 99.94%. Mass spectrum m / z: 621.2155 (calcd 621.2165). Anal. Calcd for C 41 H 27 N5O2: C, 79.21 ; H, 4.38; N, 11.27. Found: C, 79.25; H, 4.36; N, 11.26.

[0205] Synthesis Example 13: Preparation of compound 74:

[0206]

[0207] Following the same preparation procedure as in Synthesis Example 5, substituting B-3, C-3 with equimolar of B-74, C-74, compound 74 (31.17 g) was obtained, HPLC purity > 99.92%. Mass spectrum m / z: 853.3643 (calcd 853.3668). Anal. Calcd for C 61 H 47 N3O2: C, 85.79; H, 5.55; N, 4.92. Found: C, 85.73; H, 5.59; N, 4.95.

[0208] Synthesis Example 14: Preparation of compound 83:

[0209]

[0210] Following the same preparation procedure as in Synthesis Example 5, substituting A-3, B-3, C-3 with equimolar of A-28, B-83, C-46, compound 83 (27.62 g) was obtained, HPLC purity > 99.95%. Mass spectrum m / z: 681.1963 (calcd 681.1909). Anal. Calcd for C 44 H 31 N3OS2: C, 77.50; H, 4.58; N, 6.16. Found: C, 77.52; H, 4.56; N, 6.16.

[0211] Synthesis Example 15: Preparation of compound 86:

[0212]

[0213] Following the same preparation procedure as in the synthesis of Example 5, A-3, B-3, C-3 were replaced with equimolar of A-28, B-86, C-16 to give compound 86 (26.96 g) with HPLC purity > 99.97%. Mass spectrum m / z: 619.1837 (calcd 619.1896). Anal. Calcd for C 42 H 25 N3O3: C, 81.41 ; H, 4.07; N, 6.78. Found: C, 81.42; H, 4.08; N, 6.79.

[0214] Synthesis Example 16: Preparation of compound 96:

[0215]

[0216] Following the same preparation procedure as in the synthesis of Example 5, A-3, B-3, C-3 were replaced with equimolar of A-28, B-96, C-46 to give compound 96 (28.68 g) with HPLC purity > 99.99%. Mass spectrum m / z: 651.1460 (calcd 651.1439). Anal. Calcd for C 42 H 25 N3OS2: C, 77.39; H, 3.87; N, 6.45. Found: C, 77.38; H, 3.87; N, 6.47.

[0217] Synthesis Example 17: Preparation of compound 101:

[0218]

[0219] Following the same preparation procedure as in the synthesis of Example 5, A-3, B-3, C-3 were replaced with equimolar of A-101, B-101, C-16 to give compound 101 (24.83 g) with HPLC purity > 99.96%. Mass spectrum m / z: 620.1869 (calcd 620.1848). Anal. Calcd for C 41 H 24 N4O3: C, 79.34; H, 3.90; N, 9.03. Found: C, 79.36; H, 3.91; N, 9.05.

[0220] Synthesis Example 18: Preparation of compound 104:

[0221]

[0222] Following the same preparation procedure as in Synthesis Example 5, A-3, B-3, C-3 were replaced with equimolar of A-28, B-101, C-46 to give compound 104 (26.42 g) with HPLC purity > 99.97%. Mass spectrum m / z: 636.1662 (calcd 636.1620). Anal. Calcd for C 41 H 24 N4O2S: C, 77.34; H, 3.80; N, 8.80. Found: C, 77.30; H, 3.82; N, 8.82.

[0223] Synthesis Example 19: Preparation of compound 121:

[0224]

[0225] Following the same preparation procedure as in Synthesis Example 5, A-3, B-3, C-3 were replaced with equimolar of A-28, B-121, C-16 to give compound 121 (26.40 g) with HPLC purity > 99.95%. Mass spectrum m / z: 651.2308 (calcd 651.2342). Anal. Calcd for C 43 H 33 N3O2Si: C, 79.23; H, 5.10; N, 6.45. Found: C, 79.24; H, 5.07; N, 6.48.

[0226] Synthesis Example 20: Preparation of compound 159:

[0227]

[0228] Following the same preparation procedure as in Synthesis Example 5, A-3, B-3, C-3 were replaced with equimolar of A-28, B-159, C-46 to give compound 159 (24.83 g) with HPLC purity > 99.98%. Mass spectrum m / z: 620.1689 (calcd 620.1671). Anal. Calcd for C 41 H 24 N4OS: C, 79.33; H, 3.90; N, 9.03. Found: C, 79.33; H, 3.91; N, 9.04.

[0229] Synthesis Example 21: Preparation of compound 161:

[0230]

[0231] Following the same preparation procedure as in Synthesis Example 5, A-3, B-3, C-3 were replaced with equimolar of A-28, B-96, C-161 to give compound 161 (27.05 g) with HPLC purity > 99.97%. Mass spectrum m / z: 651.1458 (calcd 651.1439). Anal. Calcd for C 42 H 25 N3OS2: C, 77.39; H, 3.87; N, 6.45. Found: C, 77.40; H, 3.88; N, 6.43.

[0232] Synthesis Example 22: Preparation of compound 179:

[0233]

[0234] Following the same preparation procedure as in Synthesis Example 5, A-3, B-3, C-3 were replaced with equimolar of A-179, B-179, C-16 to give compound 179 (27.78 g) with HPLC purity > 99.94%. Mass spectrum m / z: 685.1224 (calcd 685.1247). Anal. Calcd for C 40 H 20 F5N3OS: C, 70.07; H, 2.94; N, 6.13. Found: C, 70.09; H, 2.92; N, 6.14.

[0235] Synthesis Example 23: Preparation of compound 225:

[0236]

[0237] Following the same preparation procedure as in Synthesis Example 5, A-3, B-3, C-3 were replaced with equimolar of A-225, B-225, C-225 to give compound 225 (28.20 g) with HPLC purity > 99.92%. Mass spectrum m / z: 722.2470 (calcd 722.2493). Anal. Calcd for C 48 H 18 D 11 N3S2: C, 79.74; H, 5.57; N, 5.81. Found: C, 79.79; H, 5.54; N, 5.83.

[0238] Synthesis Example 24: Preparation of compound 246:

[0239]

[0240] Following the same preparation procedure as in Synthesis Example 5, A-3, B-3, C-3 were replaced with equimolar of A-237, B-246, C-246 to give compound 246 (23.94 g) with HPLC purity > 99.93%. Mass spectrum m / z: 613.1382 (calcd. 613.1395). Theoretical elemental content (%) C 42 H 25 N3OS: C, 81.40; H, 4.07; N, 6.78. Found: C, 81.42; H, 4.06; N, 6.77.

[0241] Synthesis Example 25: Preparation of compound 246:

[0242]

[0243] Following the same preparation procedure as in Synthesis Example 5, A-3, B-3, C-3 were replaced with equimolar of A-237, B-246, C-246 to give compound 246 (23.94 g) with HPLC purity > 99.93%. Mass spectrum m / z: 613.1382 (calcd. 613.1395). Theoretical elemental content (%) C 38 H 23 N5S2: C, 74.36; H, 3.78; N, 11.41. Found: C, 74.35; H, 3.75; N, 11.45.

[0244] Synthesis Example 26: Preparation of compound 261:

[0245]

[0246] Following the same preparation procedure as in Synthesis Example 5, A-3, B-3, C-3 were replaced with equimolar of A-237, B-246, C-246 to give compound 246 (23.94 g) with HPLC purity > 99.93%. Mass spectrum m / z: 613.1382 (calcd. 613.1395). Theoretical elemental content (%) C 40 H 23 N3OS2: C, 76.78; H, 3.70; N, 6.72. Found: C, 76.74; H, 3.68; N, 6.69.

[0247] Synthesis Example 27: Preparation of compound 280:

[0248]

[0249] Following the same preparation procedure as in the synthesis of Example 5, A-3, B-3, C-3 were replaced with equimolar of A-237, B-280, C-280 to give compound 280 (30.41 g), HPLC purity > 99.93%. Mass spectrum m / z: 769.1463 (calcd 769.1429). Anal. Calcd for C 48 H 27 N5S3: C, 74.88; H, 3.53; N, 9.10. Found: C, 74.83; H, 3.57; N, 9.11.

[0250] Synthesis Example 28: Preparation of compound 293:

[0251]

[0252] A-293 (13.22 g, 50.00 mmol), C-7 (27.51 g, 100.00 mmol), sodium tert-butoxide (14.41 g, 150.00 mmol) were added to 500 mL of toluene under nitrogen protection, Pd(OAc)2(0.10 g, 0.60 mmol), P(t-Bu)3(2.40 mL of 0.50 M toluene solution, 1.20 mmol) were added with stirring, the mixture was heated to reflux for 5 h. After the reaction was completed, the reaction solution was cooled to room temperature, distilled water was added, extracted with dichloromethane, and the organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure, and the product was recrystallized from toluene / methanol (volume ratio 10:2) to give compound 293 (24.15 g, yield 74%), HPLC purity of the solid > 99.91%. Mass spectrum m / z: 652.1615 (calcd 652.1681). Anal. Calcd for C 40 H 24 N6O2S: C, 73.60; H, 3.71; N, 12.88. Found: C, 73.60; H, 3.70; N, 12.89.

[0253] Synthesis Example 29: Preparation of compound 313:

[0254]

[0255] Following the same preparation procedure as in the synthesis of Example 28, A-293, C-16 were replaced with equimolar of A-51, C-16 to give compound 313 (26.73 g), HPLC purity > 99.97%. Mass spectrum m / z: 621.1842 (calcd 621.1801). Anal. Calcd for C 40 H23 N5O3: C, 77.28; H, 3.73; N, 11.27. Found: C, 77.28; H, 3.74; N, 11.26.

[0256] Synthesis Example 30: Preparation of compound 328:

[0257]

[0258] Following the same preparation procedure as in Synthesis Example 28, A-293, C-16 were replaced with equimolar of A-328, C-328 to give compound 328 (27.68 g) with HPLC purity > 99.95%. Mass spectrum m / z: 700.1934 (theoretical value: 700.1971). Theoretical elemental content (%) C 43 H 24 N8O3: C, 73.71; H, 3.45; N, 15.99. Found: C, 73.76; H, 3.40; N, 15.98.

[0259] Synthesis Example 31: Preparation of compound 335:

[0260]

[0261] Following the same preparation procedure as in Synthesis Example 28, A-293, C-16 were replaced with equimolar of A-28, C-46 to give compound 335 (28.11 g) with HPLC purity > 99.99%. Mass spectrum m / z: 653.1382 (theoretical value: 653.1344). Theoretical elemental content (%) C 40 H 23 N5OS2: C, 73.49; H, 3.55; N, 10.71. Found: C, 73.47; H, 3.55; N, 10.73.

[0262] Synthesis Example 32: Preparation of compound 340:

[0263]

[0264] Following the same preparation procedure as in Synthesis Example 28, A-293, C-16 were replaced with equimolar of A-28, C-340 to give compound 340 (24.49 g) with HPLC purity > 99.92%. Mass spectrum m / z: 689.2137 (theoretical value: 689.2159). Theoretical elemental content (%) C 42 H 19D8N5OS2: C, 73.12; H, 5.11; N, 10.15. Found: C, 73.10; H, 5.13; N, 10.14.

[0265] Synthesis Example 33: Preparation of compound 376:

[0266]

[0267] Compound 376 (25.19 g) was obtained according to the same preparation method as in Synthesis Example 5, by replacing A-3, B-3, C-3 with equimolar A-376, C-16, C-46, HPLC purity > 99.94%. Mass spectrum m / z: 637.1526 (theoretical value: 637.1572). Theoretical elemental content (%) C 40 H 23 N5O2S: C, 75.34; H, 3.64; N, 10.98. Found: C, 75.34; H, 3.62; N, 10.99.

[0268] Synthesis Example 34: Preparation of compound 400:

[0269]

[0270] Compound 400 (36.26 g) was obtained according to the same preparation method as in Synthesis Example 28, by replacing A-293, C-16 with equimolar A-400, C-400, HPLC purity > 99.90%. Mass spectrum m / z: 741.1681 (theoretical value: 741.1695). Theoretical elemental content (%) C 44 H 23 N9O2S: C, 71.24; H, 3.13; N, 16.99. Found: C, 71.20; H, 3.15; N, 16.99.

[0271] Synthesis Example 35: Preparation of compound 428:

[0272]

[0273] Compound 428 (26.79 g) was obtained according to the same preparation method as in Synthesis Example 28, by replacing A-293, C-16 with equimolar A-428, C-428, HPLC purity > 99.93%. Mass spectrum m / z: 686.2136 (theoretical value: 686.2183). Theoretical elemental content (%) C 40 H6D 17N3O2S: C, 78.20; H, 3.63; N, 7.20. Found: C, 78.25; H, 3.63; N, 7.15.

[0274] Synthesis Example 36: Preparation of compound 428:

[0275]

[0276] Following the same preparation procedure as in Synthesis Example 5, substituting B-3, C-3 with equimolar of B-59, C-16, compound 459 (26.39 g) was obtained with HPLC purity ≧ 99.96%. Mass spectrum m / z: 643.1814 (calcd 643.1896). Theoretical elemental content (%) C 44 H 25 N3O3: C, 82.10; H, 3.91; N, 6.53. Found: C, 82.13; H, 3.90; N, 6.52.

[0277] Synthesis Example 37: Preparation of compound 514:

[0278]

[0279] Following the same preparation procedure as in Synthesis Example 5, substituting A-3, B-3, C-3 with equimolar of A-28, B-514, C-514, compound 514 (22.76 g) was obtained with HPLC purity ≧ 99.94%. Mass spectrum m / z: 583.1328 (calcd 583.1354). Theoretical elemental content (%) C 38 H 21 N3O2S: C, 78.20; H, 3.63; N, 7.20. Found: C, 78.25; H, 3.63; N, 7.15.

[0280] Synthesis Example 38: Preparation of compound 597:

[0281]

[0282] Following the same preparation procedure as in Synthesis Example 5, substituting A-3, B-3, C-3 with equimolar of A-51, B-597, C-597, compound 597 (29.51 g) was obtained with HPLC purity ≧ 99.93%. Mass spectrum m / z: 728.1403 (calcd 728.1494). Theoretical elemental content (%) C 44 H 23F3N4O2S: C, 72.52; H, 3.18; N, 7.69. Found: C, 72.52; H, 3.19; N, 7.68.

[0283] Synthesis Example 39: Preparation of compound 623:

[0284]

[0285] Compound 623 (24.03 g) was obtained according to the same preparation method of Synthesis Example 5, by replacing A-3, B-3, C-3 with equimolar A-237, B-623, C-16, HPLC purity > 99.96%. Mass spectrum m / z: 676.1385 (theoretical value: 676.1392). Theoretical elemental content (%) C 43 H 24 N4OS2: C, 76.31; H, 3.57; N, 8.28. Found: C, 76.33; H, 3.56; N, 8.26.

[0286] [Device Examples 1-35]

[0287] Device Example 1: The ITO / Ag / ITO substrate was cleaned with 5% glass cleaning solution for 2 times, 20 minutes each time, and then cleaned with deionized water for 2 times, 10 minutes each time. The substrate was cleaned with acetone and isopropyl alcohol for 20 minutes each time by ultrasonic cleaning, and then dried at 120°C. The ITO / Ag / ITO substrate was vacuum evaporated with HI as a hole injection layer, with an evaporation thickness of 20 nm; vacuum evaporated with HT as a hole transport layer on the hole injection layer, with an evaporation thickness of 100 nm; vacuum evaporated with RH:RD (doping ratio of 95:5) as a light-emitting layer on the hole transport layer, with an evaporation thickness of 30 nm; vacuum evaporated with ET as an electron transport layer on the light-emitting layer, with an evaporation thickness of 30 nm; vacuum evaporated with LiF as an electron injection layer on the electron transport layer, with an evaporation thickness of 1 nm; vacuum evaporated with Mg:Ag (1:9) alloy as a cathode on the electron injection layer, with an evaporation thickness of 10 nm; and vacuum evaporated with compound 3 of the present application as a cover layer on the cathode, with an evaporation thickness of 80 nm.

[0288]

[0289] Device Examples 2-35: The compounds 16, 28, 46, 51, 57, 66, 72, 74, 83, 86, 96, 101, 104, 121, 159, 161, 179, 225, 237, 246, 261, 280, 293, 313, 328, 335, 340, 376, 400, 428, 459, 514, 597, 623 of the present application were used as the cover layer material instead of the compound 3 of the present application in Device Example 1, respectively. The same procedure as in Device Example 1 was applied, except for the above, to prepare the organic electroluminescent device.

[0290] Comparative Examples 1-2: The comparative compound 1, comparative compound 2 were used as the cover layer material instead of the compound 3 of the present application in Device Example 1, respectively. The same procedure as in Device Example 1 was applied, except for the above, to prepare the organic electroluminescent device.

[0291] The luminous efficiency of the organic electroluminescent device was tested by a combined IVL test system consisting of test software, computer, K2400 digital source meter produced by Keithley Company of USA and PR788 spectral scanning luminance meter of Photo Research Company of USA. The life test was performed by M6000 OLED life test system of McScience Company. The test environment was atmospheric environment and the temperature was room temperature.

[0292] The test results of the luminous properties of the obtained organic electroluminescent device are shown in Table 1. Table 1 is the test results of the luminous properties of the organic electroluminescent device prepared by the compounds of the examples of the present application and the comparative substances.

[0293] Table 1 Test results of the luminous properties of the organic electroluminescent device

[0294]

[0295]

[0296] As can be seen from the results in Table 1, compared with Comparative Examples 1-2, the devices of Device Examples 1-35 prepared by using the compounds containing heteroatoms of the present application have higher luminous efficiency and longer device life. This is because when the compounds containing heteroatoms of the present application are applied to the organic electroluminescent device as the cover layer material, the light extraction efficiency of the device can be improved, thereby improving the luminous efficiency of the device, and the compounds have better absorption in the ultraviolet light band, which can further prolong the service life of the device.

[0297] It should be noted that the present application is particularly described by individual embodiments, but those skilled in the art can make various forms or details of improvement on the present application without departing from the principles of the present application, and these improvements also fall within the protection scope of the present application.

Claims

1. A compound containing a heteroatom, characterized in that, The compound containing a heteroatom has a structure as shown in Formula 1, At least one of Ar1 and Ar2 is selected from a structure as shown in Formula 1-1, and the other is selected from any one of the following structures, E1 is selected from any one of O, S, CR5R6; E3 is selected from any one of O and S; E2 is selected from CR8 or N; R4 and R8, which are the same or different, are selected from any one of hydrogen, deuterium, halogen, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, and tri-tert-butylsilyl; R5 and R6, which are the same or different, are selected from any one of methyl, ethyl, isopropyl, tert-butyl, phenyl, and naphthyl; R4, R5, R6, and R8 can be substituted by one or more substituents selected from hydrogen, deuterium, cyano, halogen, and C1-C6 alkyl, or a combination thereof; when R4, R5, R6, and R8 are phenyl, the substituents can also be selected from phenyl; when there are two or more substituents, the two or more substituents are the same as or different from each other; said d1 is selected from 0, 1, 2, 3, 4, or 5; said d2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; said d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; said d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; said d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said d6 is the same or different selected from 0, 1, 2, 3, or 4; said d7 is selected from 0, 1, 2, or 3; said d9 is selected from 0, 1, 2, 3, 4, 5, or 6; said d 10 selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; said d 11 selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; when there are two or more R4, the two or more R4 are the same or different from each other; Formula 1-1 is selected from the following structures, R1, which is the same or different, is selected from any one of hydrogen, deuterium, halogen, cyano, methyl, ethyl, isopropyl, and tert-butyl; R1 can be substituted by one or more substituents, which are the same or different, selected from deuterium, halogen, cyano, methyl, isopropyl, and tert-butyl; when there are two or more substituents, the two or more substituents are the same as or different from each other; a1 is selected from 0, 1, 2, or 3; a3 is selected from 0, 1, or 2; a4 is selected from 0, 1, 2, 3, 4, or 5; a6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R1, the two or more R1 are the same as or different from each other; Ar3 is selected from any one of the following structures, Y is selected from O or S; R2 and R3, which are the same or different, are selected from any one of hydrogen, deuterium, halogen, cyano, methyl, ethyl, isopropyl, and tert-butyl; R2 and R3 can be substituted by one or more substituents, which are the same or different, selected from deuterium, halogen, cyano, methyl, isopropyl, and tert-butyl; when there are two or more substituents, the two or more substituents are the same as or different from each other; b1 is selected from 0, 1, 2, or 3; b2 is selected from 0, 1, 2, 3, or 4; b3 is selected from 0, 1, 2, 3, 4, 5, or 6; b5 is selected from 0, 1, or 2; when there are two or more R2, the two or more R2 are the same as or different from each other; c1 is selected from 0, 1, 2, 3, 4, 5, or 6; c2 is selected from 0, 1, 2, 3, 4, or 5; c5 is selected from 0, 1, 2, 3, or 4; when there are two or more R3, the two or more R3 are the same as or different from each other; L1, L2, and L3, which are the same or different, are selected from a single bond or any one of the following structures, R9is the same or different and is selected from any one of hydrogen, deuterium, cyano, halogen, trifluoromethyl, substituted or unsubstituted C1-C6alkyl; "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, tritium; e1is the same or different and is selected from 0, 1, 2, 3, or 4; e2is the same or different and is selected from 0, 1, 2, 3, 4, 5, or 6; e5is the same or different and is selected from 0, 1, 2, or 3; e6is the same or different and is selected from 0, 1, or 2; e7is the same or different and is selected from 0, 1, 2, 3, 4, or 5; when there are two or more R9, the two or more R9are the same or different from each other.

2. The compound containing a heteroatom according to claim 1, wherein, The chemical formula 1-1 is selected from the structures shown below, R1is the same or different and is selected from any one of hydrogen, deuterium.

3. The compound containing a heteroatom according to claim 1, wherein Ar3is selected from any one of the following structures, R2, R3are the same or different and are selected from any one of hydrogen, deuterium, phenyl.

4. The compound containing a heteroatom according to claim 1, wherein, At least one of Ar1, Ar2is selected from the structure of Formula 1-1, and the rest is selected from any one of the following structures, R4, R8are the same or different and are selected from any one of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, phenyl.

5. The compound containing a heteroatom according to claim 1, wherein At least one of Ar1, Ar2is selected from the structure of Formula 1-1, and the rest is selected from any one of the following structures, 6. The compound containing a heteroatom according to claim 1, wherein, L1, L2, L3are the same or different and are selected from a single bond or any one of the following structures, R9is the same or different and is selected from any one of hydrogen, deuterium.

7. A compound containing heteroatoms, characterized in that, The compound containing a heteroatom is selected from any one of the following structures, 8. An organic electroluminescent device comprising an anode, a cathode, and one or more organic layers disposed between or outside the anode and the cathode, characterized in that, The organic layer contains any one or a combination of at least two of the compounds containing a heteroatom according to any one of claims 1 to 7.

9. An organic electroluminescent device according to claim 8, wherein the organic layer comprises a capping layer. The covering layer contains any one or a combination of at least two of the compounds containing a heteroatom according to any one of claims 1 to 7.

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