CN116874477A - Heteroatom-containing compound and organic electroluminescent device thereof - Google Patents

Heteroatom-containing compound and organic electroluminescent device thereof Download PDF

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CN116874477A
CN116874477A CN202310834616.8A CN202310834616A CN116874477A CN 116874477 A CN116874477 A CN 116874477A CN 202310834616 A CN202310834616 A CN 202310834616A CN 116874477 A CN116874477 A CN 116874477A
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刘喜庆
孙月
陆影
杜明珠
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Changchun Hyperions Technology Co Ltd
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Changchun Hyperions Technology Co Ltd
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    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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Abstract

The invention provides a compound containing hetero atoms and an organic electroluminescent device thereof, belonging to the technical field of organic electroluminescent. When the compound containing the hetero atoms is used as a coating material to be applied to an organic electroluminescent device, the compound can effectively improve the light extraction efficiency of the device due to the good refractive index, and can be well absorbed in an ultraviolet light band, so that the device can be protected from being damaged by an organic material layer in the device caused by an external light source, and the service life of the device is greatly prolonged. The compound containing the hetero atom and the organic electroluminescent device thereof have good application effect and industrialization prospect.

Description

Heteroatom-containing compound and organic electroluminescent device thereof
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound containing hetero atoms and an organic electroluminescent device thereof.
Background
Organic Light-Emitting Diode (OLED) has the advantages of high brightness, wide viewing angle, high response speed, stable image, rich luminescent colors, high resolution, low driving voltage, full curing, ultra-thin and the like, and is widely applied to mobile phones, digital cameras, DVD (digital video disk) players, personal Digital Assistants (PDA), notebook computers, automobile sound equipment and televisions.
The OLED device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and various functional materials are mutually overlapped together according to purposes to form the OLED light-emitting device. An OLED generally comprises an anode, a cathode and an organic layer formed between the two electrodes. The organic layer of the OLED may include 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 capping layer (CPL), and the like. Under the action of an external electric field, holes injected by the anode and electrons injected by the cathode (commonly called carriers) migrate and recombine in the organic layer, and energy is transferred to the luminescent material, so that the luminescent material is excited to form excitons, the excitons are attenuated by radiation when the excited state returns to the ground state, and the attenuated energy is emitted in a light mode, so that the aim of luminescence is fulfilled.
OLED devices can be classified into three types according to the light emitting direction: bottom light emitting device, top light emitting device and two side light emitting devices. In recent years, top-emission devices have been attracting attention from research and development workers because of their advantages such as being free from limitations of pixel circuits and having a large light-emitting area. Although the top emission device does not consider the influence of the pixel circuit on the light emitting area, when light emitted from the light emitting layer of the light emitting element is incident on other films, total reflection occurs at the interface of the ITO thin film and the glass substrate and the interface of the glass substrate and air, so that the light extraction efficiency of the OLED device is greatly limited. Therefore, in order to improve the light extraction efficiency of the organic electroluminescent device and to increase the lifetime of the device, it is necessary to introduce a coating material having a high refractive index, excellent film stability, and good durability.
Disclosure of Invention
In order to improve the luminous efficiency of the organic electroluminescent device and prolong the service life of the device, the invention provides a compound containing hetero atoms and the organic electroluminescent device thereof.
The present invention provides a heteroatom-containing compound having a structure as shown in chemical formula 1,
the Ar is as follows 1 、Ar 2 At least one of the structures shown in chemical formula 1-1, and the rest is any one selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C25 heteroaryl;
the X is selected from O or S;
the z is the same or different and is selected from N or CR 1 ；
The R is 1 The same or different radicals are selected from hydrogen, deuterium, halogen, cyano, trifluoroAny one of methyl, 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, and substituted or unsubstituted C3-C25 silyl; when two or more R's are present 1 When two or more R' s 1 Identical or different from each other, or two adjacent R' s 1 Are connected with each other to form a substituted or unsubstituted ring;
the Ar is as follows 3 Selected from the structures shown in the following,
y is selected from O or S;
the u are the same or different and are selected from CH or N;
the R is 2 、R 3 The same or different one selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C25 silyl;
the b and the c are the same or different and are selected from 0, 1, 2, 3 or 4; when two or more R's are present 2 When two or more R' s 2 Identical or different from each other, or two adjacent R' s 2 Are connected with each other to form a substituted or unsubstituted ring; when two or more R's are present 3 When two or more R' s 3 Identical or different from each other, or two adjacent R' s 3 Are connected with each other to form a substituted or unsubstituted ring, wherein R 2 、R 3 Is linked to each other to form a substituted or unsubstituted ring;
the L is 1 、L 2 、L 3 The same or different arylene groups selected from the group consisting of single bonds, substituted or unsubstituted C6 to C30 arylene groups, substituted or unsubstituted C2 to C25 heteroarylene groups, substituted or unsubstituted C3 to C12 alicyclic rings, and fused ring members of C6 to C30 aromatic rings Any one or a combination thereof.
The invention also provides an organic electroluminescent device comprising an anode, a cathode and one or more organic layers disposed between or outside the anode and cathode, the organic layers comprising any one or a combination of at least two of the heteroatom-containing compounds.
The invention has the beneficial effects that:
the compound containing the hetero atoms has good refractive index, can effectively improve the light extraction efficiency of the device and improve the luminous efficiency of the device, and can protect the device from being damaged by organic layer materials in the device caused by an external light source when being used as a coating layer material in an organic electroluminescent device when being well absorbed in an ultraviolet light band, thereby greatly improving the service life of the device.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention more clear, the technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention. It will be apparent that the described embodiments are some, but not all, embodiments of the invention. And embodiments of the invention and features of the embodiments may be combined with each other without conflict. All other embodiments, which can be made by a person skilled in the art without creative efforts, based on the described embodiments of the present invention fall within the protection scope of the present invention.
Unless defined otherwise, technical or scientific terms used herein should be given the ordinary meaning as understood by one of ordinary skill in the art to which this invention belongs.
In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both its natural isotopic abundance and non-natural abundance.
In the present specification, "-" means a moiety attached to another substituent.
In this specification, when a substituent is not fixed in position on a ring, it is meant that it can be attached to any of the corresponding selectable positions of the ring.
For example, the number of the cells to be processed,can indicate->Can indicate->Can indicate-> And so on.
In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to either of the two or two rings, in particular to either of the respective selectable sites of the rings. For exampleCan indicate-> Can indicate->Can indicate-> And so on.
Halogen refers to fluorine, chlorine, bromine and iodine;
the alkyl group according to the present invention means a monovalent group obtained by removing one hydrogen atom from an alkane molecule, and may be a straight chain alkyl group, 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, particularly preferably 1 to 6 carbon atoms, and examples may include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, etc., but are not limited thereto.
The alicyclic group according to the present invention means a monovalent group obtained by removing at least one hydrogen atom from an alicyclic hydrocarbon molecule, and may be a cycloalkyl group, a cycloalkenyl group, etc., preferably having 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, most preferably 3 to 7 carbon atoms, and examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.
The aryl group according to the present invention means a monovalent group obtained by removing one hydrogen atom from the aromatic nucleus carbon of an aromatic hydrocarbon molecule, and may be a monocyclic aryl group, a polycyclic aryl group or a condensed 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 may include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, indenyl, indanyl, dihydronaphthyl, tetrahydronaphthyl, anthracenyl, phenanthryl, pyrenyl, triphenylenyl, perylenyl, and the like, but are not limited thereto.
Heteroaryl according to the present invention refers to a generic term for a monovalent group left by removing one hydrogen atom from the core carbon of an aromatic heterocycle composed of carbon and heteroatoms, which may be one or more of N, O, S, and may be a monocyclic heteroaryl, polycyclic heteroaryl or fused ring heteroaryl, preferably having 3 to 30 carbon atoms, preferably having 3 to 22 carbon atoms, more preferably having 3 to 16 carbon atoms, most preferably 3 to 8 carbon atoms, and examples may include pyridyl, pyrimidinyl, triazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, indolyl, pyridofuryl, pyridothienyl, pyridopyrrolyl, pyrimidofuranyl, pyrimidothienyl, naphthothienyl, phenanthrofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzonaphthatyl, benzonaphthathioyl, naphthazolyl, benzoxazolyl, thiazolyl, benzoxazolyl, oxazolyl, thiazolyl, oxazolyl, etc.
In the present specification, the "substituted or unsubstituted silyl group" means-Si (R k ) 3 A group wherein each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic rings. Preferably, each R k The same or different groups are selected from the following groups: 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 are selected from the following groups: 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 Alkyl, substituted or unsubstituted norbornyl. "substituted or unsubstituted C3-C25 silyl" refers to the sum of the carbon atoms in the C1-C30 alkyl, C3-C30 cycloalkyl, C6-C60 aryl, C2-C60 heteroaryl, C3-C30 alicyclic and C6-C60 aromatic fused ring groups, and C3-C30 alicyclic and C2-C60 heteroaromatic fused ring groups attached to Si. Examples of the substituted or unsubstituted silyl group such as a substituted or unsubstituted C3 to C25 silyl group may include, but are not limited to, trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, tri-t-butylsilyl group, dimethylethylsilyl group, dimethylisopropylsilyl group, dimethylt-butylsilyl group, tricyclopentylsilyl group, tricyclohexylsilyl group, triphenylsilyl group, terphenylsilyl group, tripyridylsilyl group, and the like.
The arylene group refers to a bivalent group formed by removing two hydrogen atoms from the aromatic nucleus carbon of an aromatic hydrocarbon molecule. These are not only divalent groups but also aryl groups as described above.
The heteroarylene group according to the present invention is a divalent group obtained by removing two hydrogen atoms from the nuclear carbon of an aromatic heterocycle comprising carbon and a heteroatom. These are, in addition to the divalent radicals, in each case, suitable for the description of heteroaryl radicals given above.
The fused ring group of the alicyclic ring and the aromatic ring refers to the general term that after the alicyclic ring and the aromatic ring are fused together, one hydrogen atom is removed, and a monovalent group is left. Preferably having 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, examples may include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like, but are not limited thereto. "substituted" as used herein means that a hydrogen atom in a compound group is replaced with another atom or group, and the position of substitution is not limited.
The term "substituted or unsubstituted" as used herein means not substituted or unsubstitutedSubstituted with one or more substituents selected from the group consisting of: protium, deuterium, tritium, cyano, halogen atom, amino, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C30 alicyclic group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 alicyclic group and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C1-C25 heterocycloalkyl group and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C25 alicyclic ring and C2-C30 heteroaromatic ring fused ring group, substituted or unsubstituted C6-C30 arylamine group, substituted or unsubstituted C6-C30 aryloxy group, preferably protium, deuterium, tritium, halogen atom, cyano, C1-C12 alkyl, C3-C18 alicyclic, C6-C25 aryl, C2-C25 heteroaryl, specific examples may include protium, deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, trifluoromethyl, phenyl, tolyl, mesityl, penta-phenyl, pentafluorophenyl, biphenyl, naphthyl, anthryl, phenanthryl, benzophenyl, pyrenyl, triphenylenyl, deutero-phenyl, A group, perylene group, fluoranthenyl group, 9-dimethylfluorenyl group, 9-diphenylfluorenyl group, 9-methyl-9-phenylfluorenyl group, carbazolyl group, 9-phenylcarbazolyl group, spirobifluorenyl group, carbazoloindolyl group, pyrrolyl group, furanyl group, thienyl group, indolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, triazinyl group, oxazolyl group, thiazolyl group, imidazolyl group, benzoxazolyl group, benzothiazolyl group, benzotriazole group, benzimidazolyl group, pyridooxazolyl group, pyridothiazolyl group, pyridoimidazolyl group, pyrimidoxazolyl group, pyrimidothiazolyl group, pyrimidoimidazolyl group, quinolinyl group, isoquinolinyl groupQuinolinooxazolyl, quinolinothiazolyl, quinolinoimidazolyl, phenothiazinyl, phenoxazinyl, acridinyl, and the like, but are not limited thereto. Or when the substituents are two or more, adjacent substituents may be bonded to form a ring; when the substituents are two or more, the two or more substituents are the same or different from each other.
In the present invention, "adjacent two groups are linked to form a ring" means that a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle is formed by bonding adjacent groups to each other and optionally aromatizing. The hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle may include aliphatic or aromatic heterocycles. The aliphatic hydrocarbon ring may be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocyclic ring may be a saturated aliphatic heterocyclic ring or an unsaturated aliphatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring may be a single ring or a polycyclic group. In addition, a ring formed by bonding adjacent groups may be linked to another ring to form a spiro structure. As exemplified below:
In the present specification, the ring formed by the connection may be an aromatic ring or a non-aromatic ring, and may 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 condensed ring, or the like, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornane, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, or the like, but is not limited thereto.
Embodiments of the organic electroluminescent device according to the present invention will be described below, but the embodiments of the present invention may be modified into other forms, and the scope of the present invention is not limited to the embodiments described below.
In describing the structural elements of the present invention, the use of the terms "comprising" or "comprises" and the like in the present invention means that the device or article preceding the term encompasses the device or article listed after the term and equivalents thereof without excluding other devices or articles. The terms "connected" or "connected," and the like, are not limited to physical or mechanical connections, but may include electrical connections, whether direct or indirect. "inner", "outer", "upper", "lower" and the like are used merely to indicate relative positional relationships, which may also be changed when the absolute positions of the structural elements being described are changed. In the case where a structural element such as a layer, a film, a region, or a plate is located "on" another structural element, it is understood that the structural element is located "directly above" the other structural element, and that the structural element is located in the middle. In contrast, when one structural element is located "directly above" another structural element, it is understood that there are no other structural elements in between.
The term "at least one" in the present invention includes one, two, three or more.
The term "one or more" in the present invention includes one, two, three, four, five, six, seven, eight, nine, ten or more.
The present invention provides a heteroatom-containing compound having a structure as shown in chemical formula 1,
the Ar is as follows 1 、Ar 2 At least one of the structures shown in chemical formula 1-1, and the rest is any one selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C25 heteroaryl;
the X is selected from O or S;
the z is the same or different and is selected from N or CR 1 ；
The R is 1 The same or different one selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C25 silyl; when two or more R's are present 1 When two or more R' s 1 Identical or different from each other, or two adjacent R' s 1 Are connected with each other to form a substituted or unsubstituted ring;
The Ar is as follows 3 Selected from the structures shown in the following,
y is selected from O or S;
the u are the same or different and are selected from CH or N;
the R is 2 、R 3 The same or different one selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C25 silyl;
the b and the c are the same or different and are selected from 0, 1, 2, 3 or 4; when two or more R's are present 2 When two or more R' s 2 Identical or different from each other, or two adjacent R' s 2 Are connected with each other to form a substituted or unsubstituted ring; when two or more R's are present 3 When two or more R' s 3 Identical or different from each other, or two adjacent R' s 3 Are connected with each other to form a substituted or unsubstituted ring, wherein R 2 、R 3 Is linked to each other to form a substituted or unsubstituted ring;
the L is 1 、L 2 、L 3 The same or different arylene groups selected from single bonds, substituted or unsubstituted C6 to C30, substituted or unsubstituted C2 to C25 heteroarylene groups, substituted or unsubstitutedAny one or a combination of C3-C12 alicyclic ring and C6-C30 aromatic ring.
Preferably, the Ar 1 Selected from structures shown in chemical formula 1-1;
preferably, the Ar 2 Selected from structures shown in chemical formula 1-1;
preferably, the Ar 1 And Ar is a group 2 Selected from structures shown in chemical formula 1-1;
preferably, the chemical formula 1-1 is selected from the structures shown below,
the R is 1 The same or different one is selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tertiary butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, trimethylsilyl, triethylsilyl, tri-tertiary butylsilyl, triphenylsilyl;
the R is 1 May be substituted with one or more substituents which are the same or different and are selected from any one of deuterium, halogen, cyano, trifluoromethyl, methyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, trimethylsilyl, triphenylsilyl; when two or more substituents are present, the two or more substituents may be the same or different from each other;
The a 1 Selected from 0, 1, 2 or 3; the a 2 Selected from 0, 1, 2, 3 or 4; the a 3 Selected from 0, 1 or 2; the a 4 Selected from 0, 1, 2, 3, 4 or 5; the a 5 Selected from 0, 1, 2, 3, 4, 5 or 6; the a 6 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; the a 7 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when two or more R's are present 1 When two or more R' s 1 Are the same as or different from each other.
Preferably, the Ar 3 Selected from any one of the structures shown below,
y is selected from O or S;
the R is 2 、R 3 The same or different one is selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tertiary butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, trimethylsilyl, triethylsilyl, tri-tertiary butylsilyl, triphenylsilyl;
the R is 2 、R 3 May be substituted with one or more substituents which are the same or different and are selected from any one of deuterium, halogen, cyano, trifluoromethyl, methyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, trimethylsilyl, triphenylsilyl; when two or more substituents are present, the two or more substituents may be the same or different from each other;
Said b 1 Selected from 0, 1, 2 or 3; said b 2 Selected from 0, 1, 2, 3 or 4; said b 3 Selected from 0, 1, 2, 3, 4, 5 or 6; said b 4 Selected from 0, 1, 2, 3, 4 or 5; said b 5 Selected from 0, 1 or 2; when two or more R's are present 2 When two or more R' s 2 Are the same as or different from each other;
the c 1 Selected from 0, 1, 2, 3, 4, 5 or 6; the c 2 Selected from 0, 1, 2, 3, 4 or 5; the c 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c 4 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c 5 Selected from 0, 1, 2, 3 or 4; when two or more R's are present 3 When two or more R' s 3 Are the same as or different from each other.
Preferably, the Ar 1 、Ar 2 At least one of the structures shown in chemical formula 1-1, and the rest is any one of the structures shown below,
the v is the same or different and is selected from N or CH;
the E is 1 、E 3 、E 4 、E 5 The same or different are selected from O, S, CR 5 R 6 、NR 7 Any one of them;
the E is 2 Selected from CR 8 Or N;
the R is 7 Any one selected from 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;
The R is 4 、R 5 、R 6 、R 8 The same or different one selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C25 silyl;
said d 1 Selected from 0, 1, 2, 3, 4 or 5; said d 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said d 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said d 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said d 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when two or more R's are present 4 When two or more R' s 4 Identical or different from each other, or two adjacent R' s 4 Are linked to each other to form a substituted or unsubstituted ring.
Preferably, the Ar 1 、Ar 2 At least one of the structures shown in chemical formula 1-1, and the rest is any one of the structures shown below,
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the E is 1 、E 3 、E 4 、E 5 The same or different are selected from O, S, CR 5 R 6 、NR 7 Any one of them;
the E is 2 Selected from CR 8 Or N;
the R is 7 Any one selected from the group consisting of methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furyl, thienyl, benzofuryl, benzothienyl, pyridofuryl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthroline, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;
The R is 4 、R 5 、R 6 、R 8 The same or different radicals are selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, and,Any one of cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;
the R is 4 、R 5 、R 6 、R 7 、R 8 May be substituted with one or more substituents selected from any one of hydrogen, deuterium, cyano, halogen, trifluoromethyl, C1-C12 alkyl, C3-C12 alicyclic, C6-C18 aryl, C2-C25 heteroaryl, substituted or unsubstituted C3-C25 silyl, or a combination thereof; when two or more substituents are present, the two or more substituents may be the same or different from each other;
Said d 1 Selected from 0, 1, 2, 3, 4 or 5; said d 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said d 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said d 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said d 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said d 6 The same or different is selected from 0, 1, 2, 3 or 4; said d 7 Selected from 0, 1, 2 or 3; said d 8 Selected from 0, 1 or 2; said d 9 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 two or more R's are present 4 When two or more R' s 4 Are the same as or different from each other.
Preferably, the Ar 1 、Ar 2 At least one of the structures shown in chemical formula 1-1, and the rest is any one of the structures shown below,
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the E is 1 、E 3 、E 4 、E 5 The same or different are selected from O, S, CR 5 R 6 、NR 7 Any one of them;
the R is 7 Any one selected from methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;
The R is 4 、R 5 、R 6 The same or different radicals are selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylAny one of a alkylsilyl group, a tri-t-butylsilyl group, and a triphenylsilyl group;
the R is 4 、R 5 、R 6 、R 7 May be substituted with one or more substituents selected from any of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, t-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl; when two or more substituents are present, the two or more substituents may be the same or different from each other.
Preferably, the L 1 、L 2 、L 3 The same or different is selected from single bond or any one of the structures shown below,
the Rb and Rc are the same or different and are selected from any one or combination of hydrogen, deuterium, cyano, halogen, trifluoromethyl, C1-C12 alkyl, C3-C12 alicyclic group, C6-C18 aryl and C2-C25 heteroaryl;
the Rd is any one or combination of C1-C12 alkyl, C3-C12 alicyclic group, C6-C18 aryl and C2-C25 heteroaryl;
the R is 9 The same or different are selected from hydrogen, deuterium, cyano and halogenAny one of a essence, a trifluoromethyl group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 alicyclic group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C2-C25 heteroaryl group;
said e 1 The same or different is selected from 0, 1, 2, 3 or 4; said e 2 The same or different is selected from 0, 1, 2, 3, 4, 5 or 6; said e 3 The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e 4 The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said e 5 The same or different is selected from 0, 1, 2 or 3; said e 6 The same or different is selected from 0, 1 or 2; said e 7 The same or different is selected from 0, 1, 2, 3, 4 or 5; said e 8 The same or different is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when two or more R's are present 9 When two or more R' s 9 Identical or different from each other, or two adjacent R' s 9 With a substituted or unsubstituted ring formed therebetween.
Preferably, the Rb, rc, R 9 The same or different one is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tertiary butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tertiary butylsilyl, triphenylsilyl;
the Rb, rc, R 9 May be substituted with one or more substituents selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, t-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylene Any one of a group, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl; when two or more substituents are present, the two or more substituents may be the same or different from each other.
Preferably, rd is selected from any one of methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;
The Rd may be substituted with one or more substituents selected from any of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, t-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl; when two or more substituents are present, the two or more substituents may be the same or different from each other.
Preferably, the heteroatom-containing compound is selected from any one of the structures shown below,
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the present invention also provides a method for preparing a compound containing a heteroatom, but the preparation method of the present invention is not limited thereto. The core structure of formula 1 can be prepared by the reaction scheme shown below:
The Xa is the same or different and is selected from any one of Cl, br and I.
The present invention may bond the above substituents by a method known in the art, and the kind and position of substituents or the number of substituents may be changed according to a technique known in the art.
The present invention provides an organic electroluminescent device comprising an anode, a cathode and one or more organic layers disposed between or outside the anode and cathode, the organic layers comprising one or a combination of at least two of the heteroatom-containing compounds of the present invention.
Preferably, the organic layer according to the invention comprises a cover layer comprising one or a combination of at least two of the heteroatom-containing compounds according to the invention.
The organic layer of the present invention may 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 encapsulation layer, etc. However, the structure of the organic electroluminescent device of the present invention is not limited to the above-described structure, and if necessary, a plurality of organic layers may be omitted or simultaneously provided, and an organic layer having the same function may be formed in a laminated structure of two or more layers.
The organic electroluminescent device of the invention has the structure that:
substrate/anode/hole transport layer/light emitting layer/electron transport layer/cathode/cover layer;
a substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode/capping layer;
a substrate/anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer;
a substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer;
a substrate/anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;
a 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;
a 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/cover layer;
however, the structure of the organic electroluminescent device is not limited thereto. The organic electroluminescent device can be selected and combined according to the device parameter requirement and the material characteristics, partial organic layers can be added or omitted, and the organic layers with the same function can be made into a laminated structure with more than two layers.
The organic electroluminescent device of the present invention is generally formed on a substrate. The substrate may be a substrate made of glass, plastic, polymer film, silicon, or the like, as long as it is not changed when an electrode is formed or an organic layer is formed.
In the organic electroluminescent device according to the present invention, the anode material preferably uses a high work function material capable of promoting injection of holes into the organic layer. Specific examples of the anode material that can be used in the present invention may include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc 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.
In the organic electroluminescent device of the present invention, the hole injection material is preferably a material having a good hole accepting ability. Specific examples of the hole injecting material that can be used in the present invention may include: silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide, other metal oxides, phthalocyanine compounds, biphenylamine compounds, phenazine compounds, other materials, such as copper phthalocyanine (CuPc), titanyl phthalocyanine, N ' -diphenyl-N, N ' -di- [4- (N, N-diphenylamine) phenyl ] benzidine (NPNPB), N ' -tetra (4-methoxyphenyl) benzidine (MeO-TPD), and bisquinoxalino [2,3-a:2',3' -c ] phenazine (HATNA), 4',4 "-tris [ 2-naphthylphenylamino ] triphenylamine (2T-NATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazabenzophenanthrene (HAT-CN), 4',4" -tris (N, N-diphenylamino) triphenylamine (TDATA), and the like, but are not limited thereto.
In the organic electroluminescent device according to the present invention, the hole transporting material is preferably a material having excellent hole transporting property and HOMO level matching with the corresponding anode material. Specific examples of the hole transporting material that can be used in the present invention may include materials such as diphenylamines, triphenylamines, fluorenes, and carbazoles, such as N, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), N ' -di (naphthalen-1-yl) -N, N ' -di (phenyl) -2,2' -dimethylbenzidine (α -NPD), 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.
In the organic electroluminescent device, the luminescent auxiliary layer is preferably a material with good hole transmission performance and electron blocking performance. Specific examples of the light-emitting auxiliary material that can be used in the present invention may include triarylamine derivatives, spirofluorene derivatives, furan derivatives, and the like, such as TPD, NPB, N, 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' -diphenyl ] -4-yl) -N- (9, 9-dimethyl-9H-furan-2-yl) -9,9 '-spirobifluorene-2-amine, N-bis ([ 1,1' -biphenyl ] -4-yl) -3'- (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine, and the like, but is not limited thereto.
In the organic electroluminescent device of the present invention, the luminescent layer material comprises a luminescent layer host material and a luminescent layer doping material, and the luminescent layer host material may be selected from 4,4 '-bis (9-Carbazolyl) Biphenyl (CBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), 4-bis (9-carbazolyl) biphenyl (CPB), 9' - (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -ADN), N' -bis- (1-naphthyl) -N, N '-diphenyl- [1,1':4', 1':4', 1' -tetrabiphenyl]-4, 4' -diamine (4 PNPB), 1,3, 5-tris (9-carbazolyl) benzene (TCP), etc., but is not limited thereto. Preferably, the host material of the luminescent layer according to the present invention is selected from 9, 10-bis (2-naphthyl) Anthracene (ADN), 9'- (1, 3-phenyl) bis-9H-carbazole (mCP), 4' -tris(carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -AND), AND the like. The light-emitting layer doping 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' -di [4- (diphenylamino) styryl)]Biphenyl (BDAVBi), 4' -di [4- (di-p-tolylamino) styryl]Diphenyl (DPAVBi), bis (2-hydroxyphenylpyridine) beryllium (Bepp 2), bis (4, 6-difluorophenylpyridine-C2, N) iridium picolinate (FIrpic), tris (2-phenylpyridine) iridium (Ir (ppy) 3 ) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy) 2 (acac)), 9, 10-bis [ N- (p-tolyl) anilino group]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), tris [ 1-phenylisoquinoline-C2, N]Iridium (III) (Ir (piq) 3 ) Ir (piq) iridium bis (1-phenylisoquinoline) (acetylacetonate) 2 (acac)) and the like, but is not limited thereto. Preferably, the light-emitting layer guest according to the present invention is selected from the group consisting of 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 group]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), and the like.
The doping ratio of the host material for the light-emitting layer and the doping material for the light-emitting layer may be varied depending on the materials used, and is usually 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.
In the organic electroluminescent device according to the present invention, the hole blocking material has a strong hole blocking ability and suitable HOMO and LUMO energy levels, and specific examples of the hole blocking material that can be used in the present invention may include imidazoles, triazoles, phenanthroline derivatives, etc., such as 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), 3- (biphenyl-4-yl) -5- (4-t-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), etc., but are not limited thereto.
In the organic electroluminescent device according to the present invention, the electron transport material is preferably a material having a strong electron withdrawing ability and low HOMO and LUMO energy levels, and specific examples of the electron transport material usable in the present invention may include imidazoles, triazoles, phenanthroline derivatives, quinolines, 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' -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- (naphthalene-2-yl) -4,7- (diphenyl) -1, 10-phenanthrene (hnb), 8-hydroxy-Lithium (LiQ), and the like, but not limited thereto.
In the organic electroluminescent device according to the present invention, the electron injection material preferably has a small potential barrier difference from an adjacent organic transport material, host material, or the like, and at the same time has an effect of injecting electrons from the cathode. Examples of electron injection materials that can be used in the present invention include: alkali metal salts (e.g., liF, csF), alkaline earth metal salts (e.g., mgF) 2 ) Metal oxides (such as Al 2 O 3 、MoO 3 ) But is not limited thereto.
In the organic electroluminescent device according to the present invention, the cathode material preferably uses a low work function material capable of promoting electron injection into the organic layer. Specific examples of the cathode material that can be used in the present invention may include: metals such as aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof; multilayer metallic materials, e.g. LiF/Al, mg/Ag, li/Al, liO 2 /Al、BaF 2 Al, etc., but is not limited thereto.
In the organic electroluminescent device according to the present invention, the material for the cover layer is preferably a material for improving optical coupling. Specific examples of the material for the coating layer which can be used in the present invention may include arylamine derivatives, carbazole derivatives, benzimidazole derivatives, triazole derivatives, lithium fluoride, heteroatom-containing compounds described in the present invention, and the like, and preferably the heteroatom-containing compounds described in the present invention, the coating layer may be formed on the outside of the anode and the outside of the cathode at the same time, or may be disposed on the outside of the anode or the outside of the cathode, and preferably the coating layer described in the present invention is disposed on the outside of the cathode.
The thickness of each organic layer of the organic electroluminescent device is not particularly limited, and may be any thickness commonly used in the art.
The organic electroluminescent device of the present invention may be any one of a vacuum evaporation method, a spin coating method, a vapor deposition method, a blade coating method, a laser thermal transfer method, an electrospray coating method, a slit coating method, and a dip coating method, and in the present invention, a vacuum evaporation method is preferably used.
The organic electroluminescent device can be widely applied to the fields of panel display, illumination light sources, flexible OLED, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, indication boards, signal lamps and the like.
The present invention is explained more fully by the following examples, but is not intended to be limited thereby. Based on this description, one of ordinary skill in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the full scope of the disclosure without undue burden.
Preparation and characterization of the Compounds
Description of the starting materials, reagents and characterization equipment:
the raw materials and reagent sources used in the following examples are not particularly limited, and may be commercially available products or prepared by methods well known to those skilled in the art.
The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;
the elemental analysis uses a Vario EL cube type organic elemental analyzer of Elementar, germany, and the mass of the sample is 5-10 mg; synthesis example 1: preparation of intermediate C-328:
a-328 (28.87 g,150.00 mmol), b-328 (24.59 g,150.00 mmol) and K were added sequentially to a reaction flask under nitrogen 2 CO 3 (34.55 g,250 mmol) and 750mL of the mixtureAfter air was replaced three times with nitrogen in the solvent (toluene: ethanol: water=2:1:1), pd (PPh) was added 3 ) 4 (1.73 g,1.5 mmol) was stirred at reflux temperature for 4h, cooled to room temperature after the reaction was completed, suction filtered to give a cake, and the cake was rinsed with ethanol, and finally toluene was used for the cake: ethanol=10:3 recrystallisation gives intermediate C-328 (27.10 g, 78% yield), HPLC purity ≡ 99.83%. Mass spectrum m/z:231.0145 (theory: 231.0199).
Synthesis example 2: preparation of intermediate C-400:
the same preparation as in Synthesis example 1 was repeated except that a-328 and b-328 were replaced with equimolar amounts of a-400 and b-400 to obtain intermediate C-400 (33.40 g) having an HPLC purity of 99.81%. Mass spectrum m/z:282.0374 (theory: 282.0308).
Synthesis example 3: preparation of intermediate C-428:
the same preparation as in Synthesis example 1 was repeated except that a-328 and b-328 were replaced with equimolar amounts of a-428 and b-428 to obtain intermediate C-428 (31.97 g), and the HPLC purity was. Mass spectrum m/z:250.0249 (theory: 250.0270).
Synthesis example 4: preparation of intermediate C-597:
according to the same manner as in Synthesis example 1 except that a-328 and b-328 were replaced with equimolar amounts of a-597 and b-597, intermediate C-597 (32.36 g) was obtained, and HPLC purity was ≡ 99.86%. Mass spectrum m/z:299.0012 (theory: 299.0073).
Synthesis example 5: preparation of compound 3:
synthesis of intermediate D-3
Under nitrogen, 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 600ml toluene solvent and Pd (OAc) was added under stirring 2 (0.17g，1.00mmol)、P(t-Bu) 3 (4.00 mL of a 0.5M toluene solution, 2.00 mmol) and the mixture of the above reactants was heated under reflux for 4h. After the reaction was completed, cooling to room temperature, adding distilled water, extracting with methylene chloride, standing for liquid separation, collecting an organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by distillation under reduced pressure, cooling for crystallization, suction-filtering, and subjecting the obtained solid to toluene: recrystallisation from methanol=8:2 gives intermediate D-3 (36.93 g, 80% yield) with HPLC purity ≡99.87%. Mass spectrum m/z:461.1725 (theory: 461.1780).
Synthesis of Compound 3
Intermediate D-3 (23.08 g,50.00 mmol), C-3 (13.76 g,50.00 mmol) and NaOt-Bu (7.69 g,80 mmol) were dissolved in 500ml toluene solvent under nitrogen and Pd was added under stirring 2 (dba) 3 (0.48 g,0.50 mmol) and X-Phos (0.38, 0.75 mmol), and the mixture of the above reactants was heated under reflux for 5.5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added, extraction was performed with methylene chloride, the mixture was left standing and separated, the organic layer was collected and dried over anhydrous magnesium sulfate, the filtrate was concentrated by distillation under reduced pressure, the temperature was lowered and crystallized, suction filtration was performed, and the obtained solid was recrystallized from toluene to obtain compound 3 (27.21 g, yield 83%), and HPLC purity was > 99.97%. Mass spectrum m/z:655.2281 (theory: 655.2260). Theoretical element content (%) C 46 H 29 N 3 O 2 : c,84.25; h,4.46; n,6.41. Measured element content (%): c,84.21; h,4.45; n,6.46. Synthesis example 6: preparation of Compound 16:
substitution of A-3, B-3 and C-3 according to the same preparation method as in Synthesis example 5Equimolar amounts of A-16, B-16 and C-16 gave Compound 16 (27.09 g) with an HPLC purity of > 99.95%. Mass spectrum m/z:685.2642 (theory: 685.2636). Theoretical element content (%) C 48 H 23 D 6 N 3 O 2 : c,84.06; h,5.14; n,6.13. Measured element content (%): c,84.07; h,5.14; n,6.12.
Synthesis example 7: preparation of Compound 28:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-28, B-28 and C-16, compound 28 (27.09 g) was obtained with an HPLC purity of ≡ 99.95%. Mass spectrum m/z:685.2642 (theory: 685.2636). Theoretical element content (%) C 48 H 23 D 6 N 3 O 2 : c,82.88; h,4.35; n,7.25. Measured element content (%): c,82.85; h,4.36; n,7.27.
Synthesis example 8: preparation of compound 46:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-28, B-46 and C-46, compound 46 (27.77 g) was obtained with an HPLC purity of ≡ 99.99%. Mass spectrum m/z:645.1884 (theory: 645.1875). Theoretical element content (%) C 44 H 27 N 3 OS: c,81.84; h,4.21; n,6.51. Measured element content (%): c,81.84; h,4.22; n,6.50.
Synthesis example 9: preparation of Compound 51:
according to the same production method as that of Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-51, B-46 and C-16, compound 51 (24.75 g) was obtained,HPLC purity. Mass spectrum m/z:630.2026 (theory: 630.2056). Theoretical element content (%) C 43 H 26 N 4 O 2 : c,81.89; h,4.16; n,8.88. Measured element content (%): c,81.83; h,4.18; n,8.92.
Synthesis example 10: preparation of compound 57:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-28, B-57 and C-46, compound 57 (25.46 g) was obtained with an HPLC purity of ≡ 99.97%. Mass spectrum m/z:669.1842 (theory: 669.1875). Theoretical element content (%) C 46 H 27 N 3 OS: c,82.49; h,4.06; n,6.27. Measured element content (%): c,82.48; h,4.08; n,6.26.
Synthesis example 11: preparation of compound 66:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-51, B-66 and C-66, compound 66 (27.52 g) was obtained with an HPLC purity of ≡ 99.96%. Mass spectrum m/z:696.1928 (theory: 696.1984). Theoretical element content (%) C 47 H 28 N 4 OS: c,81.01; h,4.05; n,8.04. Measured element content (%): c,81.03; h,4.04; n,8.03.
Synthesis example 12: preparation of compound 72:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-28, B-72 and C-72, compound 72 (23.31 g) was obtained with an HPLC purity of ≡ 99.94%. Mass spectrum m/z:621.2155 (theory: 621.2165). Theoretical element content (%) C 41 H 27 N 5 O 2 : c,79.21; h,4.38; n,11.27. Measured element content (%): c,79.25; h,4.36; n,11.26.
Synthesis example 13: preparation of compound 74:
according to the same manner as in Synthesis example 5 except that B-3 and C-3 were replaced with equimolar amounts of B-74 and C-74, compound 74 (31.17 g) was obtained with an HPLC purity of ≡99.92%. Mass spectrum m/z:853.3643 (theory: 853.3668). Theoretical element content (%) C 61 H 47 N 3 O 2 : c,85.79; h,5.55; n,4.92. Measured element content (%): c,85.73; h,5.59; n,4.95.
Synthesis example 14: preparation of Compound 83:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-28, B-83 and C-46, compound 83 (27.62 g) was obtained with an HPLC purity of ≡ 99.95%. Mass spectrum m/z:681.1963 (theory: 681.1909). Theoretical element content (%) C 44 H 31 N 3 OS 2 : c,77.50; h,4.58; n,6.16. Measured element content (%): c,77.52; h,4.56; n,6.16.
Synthesis example 15: preparation of compound 86:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-28, B-86 and C-16, compound 86 (26.96 g) was obtained with an HPLC purity of ≡ 99.97%. Mass spectrum m/z:619.1837 (theory: 619.1896). Theoretical element content (%) C 42 H 25 N 3 O 3 : c,81.41; h,4.07; n,6.78. Real worldElement content (%): c,81.42; h,4.08; n,6.79.
Synthesis example 16: preparation of compound 96:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-28, B-96 and C-46, compound 96 (28.68 g) was obtained with an HPLC purity of ≡ 99.99%. Mass spectrum m/z:651.1460 (theory: 651.1439). Theoretical element content (%) C 42 H 25 N 3 OS 2 : c,77.39; h,3.87; n,6.45. Measured element content (%): c,77.38; h,3.87; n,6.47.
Synthesis example 17: preparation of compound 101:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-101, B-101 and C-16, compound 101 (24.83 g) was obtained with an HPLC purity of ≡ 99.96%. Mass spectrum m/z:620.1869 (theory: 620.1848). Theoretical element content (%) C 41 H 24 N 4 O 3 : c,79.34; h,3.90; n,9.03. Measured element content (%): c,79.36; h,3.91; n,9.05.
Synthesis example 18: preparation of compound 104:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-28, B-101 and C-46, compound 104 (26.42 g) was obtained with an HPLC purity of ≡ 99.97%. Mass spectrum m/z:636.1662 (theory: 636.1620). Theoretical element content (%) C 41 H 24 N 4 O 2 S: c,77.34; h,3.80; n,8.80. Measured element content (%): c,77.30; h,3.82; n,8.82.
Synthesis example 19: preparation of compound 121:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-28, B-121 and C-16, compound 121 (26.40 g) was obtained with an HPLC purity of ≡ 99.95%. Mass spectrum m/z:651.2308 (theory: 651.2342). Theoretical element content (%) C 43 H 33 N 3 O 2 Si: c,79.23; h,5.10; n,6.45. Measured element content (%): c,79.24; h,5.07; n,6.48.
Synthesis example 20: preparation of compound 159:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-28, B-159 and C-46, compound 159 (24.83 g) was obtained with an HPLC purity of ≡ 99.98%. Mass spectrum m/z:620.1689 (theory: 620.1671). Theoretical element content (%) C 41 H 24 N 4 OS: c,79.33; h,3.90; n,9.03. Measured element content (%): c,79.33; h,3.91; n,9.04.
Synthesis example 21: preparation of compound 161:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-28, B-96 and C-161, compound 161 (27.05 g) was obtained with an HPLC purity of ≡ 99.97%. Mass spectrum m/z:651.1458 (theory: 651.1439). Theoretical element content (%) C 42 H 25 N 3 OS 2 : c,77.39; h,3.87; n,6.45. Measured element content (%): c,77.40; h,3.88; n,6.43.
Synthesis example 22: preparation of Compound 179:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-179, B-179 and C-16, compound 179 (27.78 g) was obtained with an HPLC purity of ≡ 99.94%. Mass spectrum m/z:685.1224 (theory: 685.1247). Theoretical element content (%) C 40 H 20 F 5 N 3 OS: c,70.07; h,2.94; n,6.13. Measured element content (%): c,70.09; h,2.92; n,6.14.
Synthesis example 23: preparation of compound 225:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-225, B-225 and C-225, compound 225 (28.20 g) was obtained, and HPLC purity was ≡ 99.92%. Mass spectrum m/z:722.2470 (theory: 722.2493). Theoretical element content (%) C 48 H 18 D 11 N 3 S 2 : c,79.74; h,5.57; n,5.81. Measured element content (%): c,79.79; h,5.54; n,5.83.
Synthesis example 24: preparation of compound 246:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-237, B-237 and C-16, compound 237 (25.41 g) was obtained, and HPLC purity was ≡ 99.96%. Mass spectrum m/z:619.1753 (theory: 619.1718). Theoretical element content (%) C 42 H 25 N 3 OS: c,81.40; h,4.07; n,6.78. Measured element content (%): c,81.42; h,4.06; n,6.77.
Synthesis example 25: preparation of compound 246:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-237, B-246 and C-246, compound 246 (23.94 g) was obtained, and HPLC purity was ≡ 99.93%. Mass spectrum m/z:613.1382 (theory: 613.1395). Theoretical element content (%) C 38 H 23 N 5 S 2 : c,74.36; h,3.78; n,11.41. Measured element content (%): c,74.35; h,3.75; n,11.45.
Synthesis example 26: preparation of compound 261:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-237, B-261 and C-46, compound 261 (24.40 g) was obtained with an HPLC purity of ≡ 99.91%. Mass spectrum m/z:625.1658 (theory: 625.1283). Theoretical element content (%) C 40 H 23 N 3 OS 2 : c,76.78; h,3.70; n,6.72. Measured element content (%): c,76.74; h,3.68; n,6.69.
Synthesis example 27: preparation of compound 280:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-237, B-280 and C-280, compound 280 (30.41 g) was obtained, and the HPLC purity was ≡ 99.93%. Mass spectrum m/z:769.1463 (theory: 769.1429). Theoretical element content (%) C 48 H 27 N 5 S 3 : c,74.88; h,3.53; n,9.10. Measured element content (%): c,74.83; h,3.57; n,9.11.
Synthesis example 28: preparation of compound 293:
under nitrogen, 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 500ml toluene and Pd (OAc) was added under stirring 2 (0.10g，0.60mmol)、P(t-Bu) 3 (2.40 mL of a 0.50M toluene solution, 1.20 mmol) and the mixture of the above reactants was heated under reflux for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, distilled water was added, extraction was performed with methylene chloride, the mixture was left standing for separation, the organic layer was collected and dried over anhydrous magnesium sulfate, filtration was performed, the filtrate was concentrated by distillation under reduced pressure, cooling crystallization was performed, suction filtration was performed, and the obtained solid was recrystallized from toluene/methanol (volume ratio 10:2) to obtain compound 293 (24.15 g, yield 74%), and the purity of the solid was ∈ 99.91% by HPLC detection. Mass spectrum m/z:652.1615 (theory: 652.1681). Theoretical element content (%) C 40 H 24 N 6 O 2 S: c,73.60; h,3.71; n,12.88. Measured element content (%): c,73.60; h,3.70; n,12.89.
Synthesis example 29: preparation of compound 313:
according to a preparation method similar to that of Synthesis example 28, A-293 and C-16 were replaced with equimolar amounts of A-51 and C-16 to obtain compound 313 (26.73 g), with HPLC purity ≡ 99.97%. Mass spectrum m/z:621.1842 (theory: 621.1801). Theoretical element content (%) C 40 H 23 N 5 O 3 : c,77.28; h,3.73; n,11.27. Measured element content (%): c,77.28; h,3.74; n,11.26.
Synthesis example 30: preparation of compound 328:
according to the same manner as that of Synthesis example 28 except that A-293 and C-16 were replaced with equimolar amounts of A-328 and C-328, compound 328 (27.68 g) was obtained with an HPLC purity of ≡99.95%.Mass spectrum m/z:700.1934 (theory: 700.1971). Theoretical element content (%) C 43 H 24 N 8 O 3 : c,73.71; h,3.45; n,15.99. Measured element content (%): c,73.76; h,3.40; n,15.98.
Synthesis example 31: preparation of compound 335:
according to the same manner as that of Synthesis example 28 except that A-293 and C-16 were replaced with equimolar amounts of A-28 and C-46, compound 335 (28.11 g) was obtained with an HPLC purity of ≡99.99%. Mass spectrum m/z:653.1382 (theory: 653.1344). Theoretical element content (%) C 40 H 23 N 5 OS 2 : c,73.49; h,3.55; n,10.71. Measured element content (%): c,73.47; h,3.55; n,10.73.
Synthesis example 32: preparation of compound 340:
according to the same manner as that of Synthesis example 28 except that A-293 and C-16 were replaced with equimolar amounts of A-28 and C-340, compound 340 (24.49 g) was obtained with an HPLC purity of ≡99.92%. Mass spectrum m/z:689.2137 (theory: 689.2159). Theoretical element content (%) C 42 H 19 D 8 N 5 OS 2 : c,73.12; h,5.11; n,10.15. Measured element content (%): c,73.10; h,5.13; n,10.14.
Synthesis example 33: preparation of compound 376:
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according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-376, C-16 and C-46, compound 376 (25.19 g) was obtained with an HPLC purity of ≡ 99.94%. Mass spectrum m/z:637.1526 (theory: 637.1572). Theoretical element content%％)C 40 H 23 N 5 O 2 S: c,75.34; h,3.64; n,10.98. Measured element content (%): c,75.34; h,3.62; n,10.99.
Synthesis example 34: preparation of compound 400:
according to the same manner as that of Synthesis example 28 except that A-293 and C-16 were replaced with equimolar A-400 and C-400, compound 400 (36.26 g) was obtained, and HPLC purity was ≡99.90%. Mass spectrum m/z:741.1681 (theory: 741.1695). Theoretical element content (%) C 44 H 23 N 9 O 2 S: c,71.24; h,3.13; n,16.99. Measured element content (%): c,71.20; h,3.15; n,16.99.
Synthesis example 35: preparation of Compound 428:
according to the same manner as that of Synthesis example 28 except that A-293 and C-16 were replaced with equimolar amounts of A-428 and C-428, compound 428 (26.79 g) was obtained, and HPLC purity was ≡ 99.93%. Mass spectrum m/z:686.2136 (theory: 686.2183). Theoretical element content (%) C 40 H 6 D 17 N 5 S 3 : c,69.94; h,5.86; n,10.20. Measured element content (%): c,69.95; h,5.86; n,10.20.
Synthesis example 36: preparation of Compound 428:
according to the same manner as in Synthesis example 5 except that B-3 and C-3 were replaced with equimolar amounts of B-59 and C-16, compound 459 (26.39 g) was obtained with an HPLC purity of ≡99.96%. Mass spectrum m/z:643.1814 (theory: 643.1896). Theoretical element content (%) C 44 H 25 N 3 O 3 ：C,82.10；H,3.91; n,6.53. Measured element content (%): c,82.13; h,3.90; n,6.52.
Synthesis example 37: preparation of compound 514:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-28, B-514 and C-514, compound 514 (22.76 g) was obtained with an HPLC purity of ≡ 99.94%. Mass spectrum m/z:583.1328 (theory: 583.1354). Theoretical element content (%) C 38 H 21 N 3 O 2 S: c,78.20; h,3.63; n,7.20. Measured element content (%): c,78.25; h,3.63; n,7.15.
Synthesis example 38: preparation of compound 597:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-51, B-597 and C-597, compound 597 (29.51 g) was obtained, and HPLC purity was ≡ 99.93%. Mass spectrum m/z:728.1403 (theory: 728.1494). Theoretical element content (%) C 44 H 23 F 3 N 4 O 2 S: c,72.52; h,3.18; n,7.69. Measured element content (%): c,72.52; h,3.19; n,7.68.
Synthesis example 39: preparation of compound 623:
according to the same manner as in Synthesis example 5 except that A-3, B-3 and C-3 were replaced with equimolar amounts of A-237, B-623 and C-16, compound 623 (24.03 g) was obtained with an HPLC purity of ≡ 99.96%. Mass spectrum m/z:676.1385 (theory: 676.1392). Theoretical element content (%) C 43 H 24 N 4 OS 2 : c,76.31; h,3.57; n,8.28. Measured element content (%): c,76.33；H,3.56；N,8.26。
Device examples 1 to 35
Device example 1: the ITO/Ag/ITO substrate was ultrasonically cleaned with 5% glass washer fluid for 2 times, 20 minutes each time, and deionized water for 2 times, 10 minutes each time. Sequentially ultrasonic cleaning with acetone and isopropanol for 20 min, and drying at 120deg.C. Vacuum evaporating HI on the ITO/Ag/ITO substrate to serve as a hole injection layer, wherein the evaporation thickness is 20nm; vacuum evaporation HT is carried out on the hole injection layer to serve as a hole transport layer, and the evaporation thickness is 100nm; vacuum evaporation of RH on hole transport layer: RD (doping ratio of 95:5) is used as a light-emitting layer, and the vapor deposition thickness is 30nm; vacuum evaporating ET on the luminous layer as an electron transport layer, wherein the evaporating thickness is 30nm; vacuum evaporating LiF on the electron transport layer as an electron injection layer, wherein the evaporating thickness is 1nm; vapor deposition of Mg on the electron injection layer: ag (1:9) alloy is used as a cathode, the evaporation thickness is 10nm, the compound 3 of the invention is used as a coating layer by vacuum evaporation on the cathode, and the evaporation thickness is 80nm.
Device examples 2 to 35: an organic electroluminescent device was produced by the same procedure as in device example 1, except that the compound 3 of the present invention in device example 1 was replaced as a capping layer material with 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 invention, respectively.
Comparative examples 1-2: an organic electroluminescent device was produced by the same procedure as in device example 1, except that the compound 3 of the present invention in device example 1 was replaced with the comparative compound 1 and the comparative compound 2, respectively, as the capping layer material.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectrum scanning luminance meter manufactured by Photo Research company, U.S. are combined into a combined IVL test system to test the luminous efficiency of the electroluminescent device. Life testing an M6000 OLED life test system from McScience was used. The environment tested was atmospheric and the temperature was room temperature.
The results of the luminescence characteristic test of the obtained organic electroluminescent device are shown in table 1. Table 1 shows the results of the test of the luminescence characteristics of the organic electroluminescent devices prepared from the compounds according to the examples of the present invention and the comparative materials.
Table 1 test of light emitting characteristics of organic electroluminescent device
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As can be seen from the results in table 1, the device examples 1 to 35 prepared using the heteroatom-containing compound of the present invention have higher luminous efficiency and longer device lifetime than the comparative examples 1 to 2. The compound containing the hetero atoms can improve the light extraction efficiency of the device when being applied to the organic electroluminescent device as a cover layer material, so that the luminous efficiency of the device is improved, the compound can be well absorbed in an ultraviolet light wave band, and the service life of the device can be further prolonged.
It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.

Claims (10)

1. A heteroatom-containing compound characterized in that the heteroatom-containing compound has a structure as shown in chemical formula 1,
the Ar is as follows 1 、Ar 2 At least one of the structures shown in chemical formula 1-1, and the rest is any one selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C25 heteroaryl;
The X is selected from O or S;
the z is the same or different and is selected from N or CR 1 ；
The R is 1 The same or different one selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C25 silyl; when two or more R's are present 1 When two or more R' s 1 Identical or different from each other, or two adjacent R' s 1 Are connected with each other to form a substituted or unsubstituted ring;
the Ar is as follows 3 Selected from the structures shown in the following,
y is selected from O or S;
the u are the same or different and are selected from CH or N;
the R is 2 、R 3 The same or different one selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C25 silyl;
the b and the c are the same or different and are selected from 0, 1, 2, 3 or 4; when two or more R's are present 2 When two or more R' s 2 Identical or different from each other, or two adjacent R' s 2 Are connected with each other to form a substituted or unsubstituted ring; when two or more R's are present 3 When two or more R' s 3 Identical or different from each other, or two adjacent R' s 3 Are connected with each other to form a substituted or unsubstituted ring, wherein R 2 、R 3 Is linked to each other to form a substituted or unsubstituted ring;
the L is 1 、L 2 、L 3 The same or different one or a combination of the same or different one selected from single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C2-C25, substituted or unsubstituted alicyclic of C3-C12 and condensed ring group of aromatic ring of C6-C30.
2. A heteroatom containing compound according to claim 1 characterized in that the chemical formula 1-1 is selected from the structures shown below,
the R is 1 The same or different one is selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tertiary butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, trimethylsilyl, triethylsilyl, tri-tertiary butylsilyl, triphenylsilyl;
The R is 1 May be substituted with one or more substituents which are the same or different and are selected from any one of deuterium, halogen, cyano, trifluoromethyl, methyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, trimethylsilyl, triphenylsilyl; when two or more substituents are present, the two or more substituents may be the same or different from each other;
the a 1 Selected from 0, 1, 2 or 3; the a 2 Selected from 0, 1, 2, 3 or 4; the a 3 Selected from 0, 1 or 2; the a 4 Selected from 0, 1, 2, 3, 4 or 5; the a 5 Selected from 0, 1, 2, 3, 4, 5 or 6; the a 6 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; the a 7 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when two or more R's are present 1 When two or more R' s 1 Are the same as or different from each other.
3. A heteroatom containing compound according to claim 1, characterized in that Ar 3 Selected from any one of the structures shown below,
y is selected from O or S;
the R is 2 、R 3 The same or different one is selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tertiary butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, trimethylsilyl, triethylsilyl, tri-tertiary butylsilyl, triphenylsilyl;
The R is 2 、R 3 May be substituted with one or more substituents which areThe same or different one is selected from deuterium, halogen, cyano, trifluoromethyl, methyl, isopropyl, tertiary butyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, trimethylsilyl and triphenylsilyl; when two or more substituents are present, the two or more substituents may be the same or different from each other;
said b 1 Selected from 0, 1, 2 or 3; said b 2 Selected from 0, 1, 2, 3 or 4; said b 3 Selected from 0, 1, 2, 3, 4, 5 or 6; said b 4 Selected from 0, 1, 2, 3, 4 or 5; said b 5 Selected from 0, 1 or 2; when two or more R's are present 2 When two or more R' s 2 Are the same as or different from each other;
the c 1 Selected from 0, 1, 2, 3, 4, 5 or 6; the c 2 Selected from 0, 1, 2, 3, 4 or 5; the c 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c 4 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c 5 Selected from 0, 1, 2, 3 or 4; when two or more R's are present 3 When two or more R' s 3 Are the same as or different from each other.
4. A heteroatom containing compound according to claim 1, characterized in that Ar 1 、Ar 2 At least one of the structures shown in chemical formula 1-1, and the rest is any one of the structures shown below,
the v is the same or different and is selected from N or CH;
the E is 1 、E 3 、E 4 、E 5 The same or different are selected from O, S, CR 5 R 6 、NR 7 Any one of them;
the E is 2 Selected from CR 8 Or N;
the R is 7 Selected from substituted or unsubstituted C1-C12 alkanesAny one of a group, a substituted or unsubstituted alicyclic group of C3 to C12, a substituted or unsubstituted aryl group of C6 to C30, a substituted or unsubstituted heteroaryl group of C2 to C25, and a substituted or unsubstituted silyl group of C3 to C25;
the R is 4 、R 5 、R 6 、R 8 The same or different one selected from hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C25 silyl;
said d 1 Selected from 0, 1, 2, 3, 4 or 5; said d 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said d 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said d 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said d 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when two or more R's are present 4 When two or more R' s 4 Identical or different from each other, or two adjacent R' s 4 Are linked to each other to form a substituted or unsubstituted ring.
5. A heteroatom containing compound according to claim 1, characterized in that Ar 1 、Ar 2 At least one of the structures shown in chemical formula 1-1, and the rest is any one of the structures shown below,
the E is 1 、E 3 、E 4 、E 5 The same or different are selected from O, S, CR 5 R 6 、NR 7 Any one of the following；
The E is 2 Selected from CR 8 Or N;
the R is 7 Any one selected from the group consisting of methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furyl, thienyl, benzofuryl, benzothienyl, pyridofuryl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthroline, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;
The R is 4 、R 5 、R 6 、R 8 The same or different one selected from 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, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthroline, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;
the R is 4 、R 5 、R 6 、R 7 、R 8 May be substituted with one or more substituents selected from the group consisting of hydrogen,Any one of deuterium, cyano, halogen, trifluoromethyl, C1-C12 alkyl, C3-C12 alicyclic, C6-C18 aryl, C2-C25 heteroaryl, substituted or unsubstituted C3-C25 silyl, or a combination thereof; when two or more substituents are present, the two or more substituents may be the same or different from each other;
Said d 1 Selected from 0, 1, 2, 3, 4 or 5; said d 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7; said d 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said d 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said d 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said d 6 The same or different is selected from 0, 1, 2, 3 or 4; said d 7 Selected from 0, 1, 2 or 3; said d 8 Selected from 0, 1 or 2; said d 9 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 two or more R's are present 4 When two or more R' s 4 Are the same as or different from each other.
6. A heteroatom containing compound according to claim 1, characterized in that Ar 1 、Ar 2 At least one of the structures shown in chemical formula 1-1, and the rest is any one of the structures shown below,
the E is 1 、E 3 、E 4 、E 5 The same or different are selected from O, S, CR 5 R 6 、NR 7 Any one of them;
the R is 7 Any one selected from methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;
The R is 4 、R 5 、R 6 The same or different one is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tertiary butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tertiary butylsilyl, triphenylsilyl;
the R is 4 、R 5 、R 6 、R 7 May be substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, oxazolyl, thiazolyl Any one of benzoxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl; when two or more substituents are present, the two or more substituents may be the same or different from each other.
7. A heteroatom-containing compound according to claim 1, characterized in that L 1 、L 2 、L 3 The same or different is selected from single bond or any one of the structures shown below,
the Rb and Rc are the same or different and are selected from any one or combination of hydrogen, deuterium, cyano, halogen, trifluoromethyl, C1-C12 alkyl, C3-C12 alicyclic group, C6-C18 aryl and C2-C25 heteroaryl;
the Rd is any one or combination of C1-C12 alkyl, C3-C12 alicyclic group, C6-C18 aryl and C2-C25 heteroaryl;
the R is 9 The same or different one is selected from any one of hydrogen, deuterium, cyano, halogen, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C25 heteroaryl;
Said e 1 The same or different is selected from 0, 1, 2, 3 or 4; said e 2 The same or different is selected from 0, 1, 2, 3, 4, 5 or 6; said e 3 The same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said e 4 The same or different is selected from 0, 1, 2, 3, 4, 5, 67, 8, 9 or 10; said e 5 The same or different is selected from 0, 1, 2 or 3; said e 6 The same or different is selected from 0, 1 or 2; said e 7 The same or different is selected from 0, 1, 2, 3, 4 or 5; said e 8 The same or different is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when two or more R's are present 9 When two or more R' s 9 Identical or different from each other, or two adjacent R' s 9 With a substituted or unsubstituted ring formed therebetween.
8. A heteroatom containing compound according to claim 1 characterized in that the heteroatom containing compound is selected from any of the structures shown below,
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9. 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 comprises any one or a combination of at least two of the heteroatom-containing compounds of any one of claims 1 to 8.
10. An organic electroluminescent device according to claim 9, the organic layer comprising a capping layer, wherein the capping layer comprises any one or a combination of at least two of the heteroatom-containing compounds of any one of claims 1 to 8.
CN202310834616.8A 2023-07-07 2023-07-07 Heteroatom-containing compound and organic electroluminescent device thereof Pending CN116874477A (en)

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