CN115948160A - Organic electroluminescent device - Google Patents
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Abstract
The invention provides an organic electroluminescent device, and relates to the technical field of organic electroluminescence. The organic electroluminescent device comprises an anode, an organic layer and a cathode, wherein the organic layer is positioned between the anode and the cathode and comprises a light-emitting layer, the light-emitting layer contains a first main material and a second main material, the first main material is a triarylamine compound shown in a formula 1, and the second main material is a heterocyclic compound shown in a formula 2. The organic electroluminescent device can effectively adjust the transmission balance of holes and electrons, the holes and the electrons can be more effectively compounded in the luminescent layer to form excitons for luminescence, the utilization rate of the excitons is improved, and the formed luminescent layer film is more stable. Therefore, the device containing the host material combination in the light-emitting layer shows higher light-emitting efficiency and longer service life.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic electroluminescent device.
Background
Compared with the conventional Liquid Crystal Display (LCD), the OLED Display is ultra-Light and ultra-thin, and has the advantages of being bendable, high in brightness, large in viewing angle, fast in response speed, self-luminous, and free of backlight source. From mobile phones to televisions, almost all display fields can become the target market of the OLED at present, and theoretically, the OLED has very bright and wide market prospect, so that the OLED has great research interest.
In the 60's 20 th century, pope et al reported the phenomenon of electroluminescence of anthracene single crystal for the first time, and opened the front of the research on organic light emitting devices, and at present, a large number of research units and enterprises have been put into the research, development and production of OLEDs throughout the country. With the progress of research, researchers have proposed various OLED device structures to improve device performance. OLED devices can be simply classified into single-layer devices, double-layer devices, triple-layer devices, multi-layer devices, etc. according to the number of organic layers in the devices. Among them, a typical organic electroluminescent device is a "sandwich" structure composed of a cathode, an Electron Transport Layer (ETL), an Emission Layer (EML), a Hole Transport Layer (HTL), and an anode, where the anode mostly adopts Indium Tin Oxide (ITO), and the cathode usually adopts a low work function metal. Under the action of an external electric field, holes generated by the anode and electrons generated by the cathode migrate to the light emitting layer, and after reaching the light emitting layer, excitons are generated by recombination and energy is released, the excitons migrate under the action of the electric field and transfer the energy to the light emitting substance, and the electrons in the molecules of the light emitting substance are transited from a ground state to an excited state. With the continuous improvement of the technology, a multilayer structure is gradually developed, and a plurality of functional auxiliary structures such as an electron injection layer, an electron blocking layer, a hole injection layer and a hole blocking layer are added, and the functional layers play different roles in the device.
In recent years, organic electroluminescent devices have greatly improved performance, but many problems still exist in commercial production and application, and at present, the main problems of organic electroluminescent devices are that the efficiency of the devices is low and the lifetime is short, and generally, a host material/dopant mixed system can be used as a light emitting layer to improve the performance of the devices, however, the selection of the host material is very important, and the host material has a great influence on the efficiency, lifetime and the like of the devices, so further research is needed to obtain organic electroluminescent devices with improved performance.
Disclosure of Invention
The invention provides an organic electroluminescent device aiming at the problems in the prior art.
The invention provides an organic electroluminescent device, which comprises an anode, an organic layer and a cathode, wherein the organic layer is positioned between the anode and the cathode, the organic layer comprises a light-emitting layer, the light-emitting layer contains a first main material and a second main material, the first main material is a triarylamine compound shown in a formula 1, the second main material is a heterocyclic compound shown in a formula 2,
wherein, ar is 1 、Ar 2 Independently selected from one of the groups shown in the following,
a0 is an integer of 0 to 5; a1 is an integer of 0 to 4; the R is 1 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R 1 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 1 When each R is 1 Are the same or different from each other;
the La, lb, lc, L 1 、L 2 Independently selected from single bond, substituted or unsubstituted aryleneOne of a substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring-fused ring group; and the-La-Lb-Lc-is not a single bond;
a is selected from an integer of 0 to 4; the R is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring group, or two adjacent Rs are mutually bonded to form a substituted or unsubstituted ring; when a is 2 or more, each R is the same as or different from each other;
wherein Ar is selected from one of the groups shown in the specification,
the R is 0 The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C20 alicyclic ring and C2-C30 heteroaromatic ring fused ring group, or two adjacent R groups 0 Bonded to each other to form a substituted or unsubstituted ring;
x is selected from O, S, C (R) x ) 2 、N(R x )、Si(R x ) 2 In a group of (A), the R x The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or a mixture thereofOne of a condensed ring group of substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring, a condensed ring group of substituted or unsubstituted C3-C20 alicyclic ring and C2-C30 heteroaromatic ring, a substituted or unsubstituted C3-C20 aliphatic heterocyclic group, or two adjacent R x Bonded to each other to form a substituted or unsubstituted ring;
b0 is an integer of 0 to 4; b is an integer of 0 to 3; the R is 5 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 aliphatic heterocyclic group, or two adjacent R groups 5 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 5 When each R is 5 Are the same or different from each other;
said L is 0 One selected from a single bond or a group shown below; n is an integer of 0 to 3; when n is 2 or more, each L 0 Are the same or different from each other;
n1 is an integer of 0 to 4; the R is 6 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 lipoheterocyclic group, or two adjacent R groups 6 Bonded to each other to form a substituted or unsubstituted ring; when n1 is 2 or more, each R 6 Are the same or different from each other;
said L 3 、L 4 Independently selected from a single bond, substituted or unsubstituted C3-C20 cycloalkylene, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic ring fused ring group;
the R is 3 、R 4 Independently selected from the group shown below,
the R is 7 One selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, and substituted or unsubstituted C3-C20 alicyclic ring group;
said X 1 Selected from O, S, N (R) x1 ) In a group of (A), the R x1 One selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, and substituted or unsubstituted C3-C20 lipoheterocyclic group;
the Y is the same or different and is selected from C (R) y ) Or N, said R y Selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstitutedOne of a substituted C2-C30 heteroaryl group, a substituted or unsubstituted condensed ring group of a C3-C20 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted condensed ring group of a C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring, a substituted or unsubstituted C3-C20 alicyclic heterocyclic group, or two adjacent R y Bonded to each other to form a substituted or unsubstituted ring.
Has the advantages that: according to the organic electroluminescent device, the first main body material with hole characteristics shown in the formula 1 and the second main body material with electron characteristics shown in the formula 2 are contained in the light-emitting layer, so that the device can effectively adjust the transmission balance of holes and electrons, the holes and the electrons can be more effectively compounded in the light-emitting layer to form excitons for light emission, the utilization rate of the excitons is improved, and the formed light-emitting layer film is more stable. Therefore, the device containing the host material combination in the light-emitting layer shows higher light-emitting efficiency and longer service life.
Detailed Description
The invention is further illustrated by the following examples which are intended to be illustrative only and not to be limiting as to the scope of the invention which is to be given the full breadth of the appended claims and any and all modifications thereof which would occur to one skilled in the art upon reading the present specification and which fall within the scope of the appended claims.
In the present invention, "CXX to CYY" in "a substituted or unsubstituted ZZ group of CXX to CYY" represents the number of carbon atoms in the unsubstituted "ZZ group," and when the "ZZ group" has a substituent, the number of carbon atoms of the substituent is not included. For example, "C1 to C20" in "substituted or unsubstituted C1 to C20 alkyl" represents the number of carbon atoms in the unsubstituted "alkyl", and when the "alkyl" has a substituent, the number of carbon atoms of the substituent is not included. "C6 to C30" in "substituted or unsubstituted C6 to C30 aryl" represents the number of carbon atoms in the unsubstituted "aryl", and when the "aryl" has a substituent, the number of carbon atoms in the substituent is not included. "C3 to C20" in the "fused ring group of a substituted or unsubstituted C3 to C20 alicyclic ring and a C6 to C30 aromatic ring" represents the number of carbon atoms in the unsubstituted "alicyclic ring", and when the "alicyclic ring" has a substituent, the number of carbon atoms in the substituent is not included; "C6 to C30" represents the number of carbon atoms in an unsubstituted "aromatic ring", and when the "aromatic ring" has a substituent, the number of carbon atoms of the substituent is not included. And so on.
In the present invention, "unsubstituted ZZ group" in "substituted or unsubstituted ZZ group" means that the hydrogen atom of "ZZ group" is not replaced by a substituent. For example, "unsubstituted aryl" in "substituted or unsubstituted C6 to C30 aryl" means that the hydrogen atom of "aryl" is not replaced by a substituent. And so on.
In the present invention, "H", "hydrogen atom" includes any isotope or mixture of isotopes, such as atoms including natural isotopic abundance, as well as isotopes having different numbers of neutrons, including protium, deuterium, tritium.
The term "substituted" in the "substituted or unsubstituted" as used herein means that at least one hydrogen atom on the group is replaced by a substituent. When a plurality of hydrogens is replaced with a plurality of substituents, the plurality of substituents may be the same or different. The position of the hydrogen substituted by the substituent may be any position. The substituent represented by "substituted" in the above "substituted or unsubstituted" includes deuterium, tritium, cyano, halogen, nitro, alkoxy, aryloxy, silyl, heterocyclic group, alkyl, cycloalkyl, aryl, heteroaryl, fused ring group of alicyclic and aromatic rings, fused ring group of alicyclic and heteroaromatic rings, arylamine group and the like. Further, each of the substituents may be substituted or unsubstituted. Two adjacent substituents may be bonded to form a ring. The following groups are preferred: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, bornyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, anthracenyl, pyrenyl, and the like,
Fluoro, anthryl, fluorenyl, benzofluorenyl, spirobifluorenyl, spiroanthracenyl, benzocycloalkyl, dihydroindenyl, tetrahydronaphthylIndenyl, dihydronaphthyl, carbazolyl, benzocarbazolyl, dibenzofuranyl, dibenzothiophenyl, spirofluorene xanthenyl, spirofluorene thianthrenyl, spirofluorene azaanthracenyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzimidazolyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, and the like.
The halogen in the invention comprises fluorine, chlorine, bromine and iodine.
The indanes include 2, 3-indanes and the tetrahydronaphthalenes include 1,2,3, 4-tetrahydronaphthalenes.
In the present invention, the substitution site on any group appearing in the present invention is any position on the group, if not specifically claimed. For example, the substitution site for the group "tetrahydronaphthyl" can be either on the phenyl ring or on a saturated six-membered ring.
In the present specification, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example,
can indicate->
And so on.
In the present specification, when a bond at a substituent or attachment site is present throughout two or more rings, it is indicated that it may be attached to either of the two or two rings, in particular to either of the corresponding alternative sites of the rings. For example,
can indicate->
Watch capable of showingShow->
And so on.
In the present invention, "two adjacent groups are bonded to form a ring" means that the adjacent groups are bonded to each other and optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocyclic ring may include an aliphatic heterocyclic ring or an aromatic heterocyclic ring. 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 rings and heterocycles may be monocyclic or polycyclic groups. In addition, a ring formed by the combination of adjacent groups may be connected to another ring to form a spiro structure. As exemplified below:
in the present invention, the ring formed by the connection may be a five-membered ring or a six-membered ring or a fused ring, such as benzene, naphthalene, phenanthrene, triphenylene, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, fluorene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, but not limited thereto. Wherein the alicyclic group in the "adjacent two groups are bonded to form an alicyclic group" may be, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but is not limited thereto.
The term "integer selected from 0 to M" as used herein means any one of the integers selected from 0 to M, including 0,1,2, 8230M-2, M-1, M. For example, "a0 is selected from an integer of 0 to 5" as used herein means that a0 is selected from 0,1,2,3,4 or 5. The expression "a1 is an integer selected from 0 to 4" means that a1 is selected from 0,1,2,3 or 4. And so on.
The alkyl refers to a univalent group formed by subtracting one hydrogen atom from alkane molecules. The alkyl group may be a straight chain alkyl group or a branched chain alkyl group. The alkyl group has 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, and still more preferably 1 to 6 carbon atoms. Examples of the alkyl group include, but are not limited to, the groups described below, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl and the like. When the number of carbon atoms of the chain alkyl group in the present invention is three or more, isomers thereof are included, and for example, a propyl group includes an n-propyl group and an isopropyl group; the butyl group includes n-butyl, isobutyl, sec-butyl and tert-butyl. And so on.
The cycloalkyl refers to a monovalent group formed by omitting one hydrogen atom from a cycloalkane molecule. The cycloalkyl group has carbon atoms of C3 to C20, preferably C3 to C15, and more preferably C3 to C10. Examples of such cycloalkyl groups include, but are not limited to, adamantyl, norbornyl, bornanyl, isobaranyl, fenchyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like, as described below.
The aryl group in the invention is a univalent group formed by dropping one hydrogen atom from the carbon of an aromatic hydrocarbon molecule. The aryl group includes monocyclic aryl groups, polycyclic aryl groups, fused ring aryl groups, or combinations thereof. The aryl group has 6 to 60 carbon atoms, preferably 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, still more preferably 6 to 18 carbon atoms, and yet more preferably 6 to 12 carbon atoms. Examples of the aryl group include but are not limited to the groups described below, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl triphenylene, anthracene group, pyrenyl group, fluoranthenyl group, benzofluoranthenyl group,
And a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a naphthofluorenyl group, a spirobifluorenyl group, a spiroanthracenyl group, and the like.
The heteroaryl group in the present invention refers to a monovalent group in which at least one carbon atom in an aryl group is substituted with a heteroatom. The heteroatom is selected from O, S, N, si, B, P, etc., but is not limited thereto. The heteroaryl group has a carbon number of C2 to C60, preferably C2 to C30, more preferably C2 to C25, and still more preferably C3 to C18. Examples of the heteroaryl group include, but are not limited to, a furyl group, a benzofuryl group, a dibenzofuryl group, a benzodibenzofuryl group, a naphthodibenzofuryl group, a thienyl group, a benzothienyl group, a dibenzothienyl group, a naphthodibenzothienyl group, a carbazolyl group, a benzocarbazolyl group, a naphthocarbazolyl group, a dibenzocarbazolyl group, a spirofluorene xanthenyl group, a spirofluorene azaanthracenyl group, an oxazolyl group, a benzoxazolyl group, a naphthoxazolyl group, a phenanthrooxazolyl group, an anthraoxazolyl group, a triphenyloxazolyl group, a thiazolyl group, a benzothiazolyl group, a naphthothiazolyl group, a phenanthrothiazolyl group, an anthrathiazolyl group, a triphenylthiazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthoimidazolyl group, a phenanthroimidazolyl group, an anthraimidazolyl group, a triphenylimidazolyl group, a pyridizinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzoquinolyl group, an benzisoquinolyl group, an acridinyl group and the like.
Alicyclic rings described herein include cycloalkyl, cycloalkenyl, cycloalkynyl, and the like. Examples of such alicyclic groups include, but are not limited to, the groups described below, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, and the like. The alicyclic ring has a carbon number of C3 to C25, preferably C3 to C20, preferably C3 to C15, and more preferably C3 to C10.
The condensed ring group of the alicyclic ring and the aromatic ring as described in the present invention is a generic name of a monovalent group obtained by condensing an alicyclic ring and an aromatic ring together and then removing one hydrogen atom. The alicyclic ring has a carbon number of C3 to C20, preferably C3 to C15, and more preferably C3 to C10. The aromatic ring has C6 to C30, preferably C6 to C25, more preferably C6 to C18, and still more preferably C6 to C12. Examples of the condensed ring group of the alicyclic and aromatic rings include, but are not limited to, benzocyclopropyl, benzocyclobutyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, indenyl, dihydronaphthyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl and the like.
The fused ring group of the alicyclic ring and the heteroaromatic ring in the present invention is a general term for the monovalent group remaining after the alicyclic ring and the heteroaromatic ring are fused together and one hydrogen atom is removed. The alicyclic ring has a carbon number of C3 to C20, preferably C3 to C15, and more preferably C3 to C10. The heteroaromatic ring has from C2 to C30, preferably from C2 to C25, more preferably from C2 to C18, and even more preferably from C2 to C12 carbon atoms. Examples of the fused cyclic group of the alicyclic and aromatic rings include, but are not limited to, a pyridocyclopropyl group, a pyridocyclobutyl group, a pyridocyclopentyl group, a pyridocyclohexyl group, a pyridocycloheptyl group, a pyrimidocyclopropyl group, a pyrimidocyclobutyl group, a pyrimidocyclopentyl group, a pyrimidocyclohexyl group, a pyrimidocycloheptyl group, a dibenzofurocyclopentyl group, a dibenzofurocyclohexyl group, a dibenzofurocycloheptyl group, a dibenzothienocyclopentyl group, a dibenzothienocyclohexyl group, a dibenzothienocycloheptyl group, a carbazolocyclopentyl group, a carbazochrocyclohexyl group, a carbazochrocycloheptyl group and the like, as described below, but are not limited thereto.
The heterocyclic group is a monovalent group formed by dropping one hydrogen atom from a carbon of a heterocyclic compound. The heteroatom is selected from O, S, N, si, B, P, etc., but is not limited thereto. The heterocyclic group includes an aliphatic heterocyclic group and an aromatic heterocyclic group. The heterocyclic group has 2 to 20, preferably 2 to 15, and more preferably 2 to 10 carbon atoms. Examples of such heterocyclic groups include, but are not limited to, azetidinyl, tetrahydropyrrole, piperidinyl, azepinyl, morpholinyl, thiomorpholinyl, tetrahydrofuryl, tetrahydrothienyl, dioxane, furyl, dibenzofuryl, thienyl, dibenzothienyl, carbazolyl, benzocarbazolyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, and the like.
The term "alicyclic heterocyclic group" as used herein refers to a divalent group formed by removing one hydrogen atom from an alicyclic hydrocarbon molecule, and the heteroatom is selected from the group consisting of O, S, N, si, B, P, and the like, but is not limited thereto. The aliphatic heterocyclic group has 2 to 20, preferably 2 to 15, and more preferably 2 to 10 carbon atoms. Examples of such aliphatic heterocyclic groups include, but are not limited to, the groups described below, azetidinyl, tetrahydropyrrolyl, piperidinyl, azepinyl, homopiperidinyl, morpholinyl, thiomorpholinyl, tetrahydrofuranyl, tetrahydrothienyl, dioxane, and the like.
The arylene group in the present invention is a divalent group obtained by removing two hydrogen atoms from a carbon in an aromatic hydrocarbon molecule. The arylene group includes monocyclic arylene, polycyclic arylene, fused ring arylene, or combinations thereof. The arylene group has 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 12 carbon atoms. Examples of the arylene group include, but are not limited to, phenylene, biphenylene, terphenylene, quaterphenylene, naphthylene, phenanthrylene, triphenylene, anthracenylene, pyrenylene, and the like
An alkyl group, an anthrylene group, a fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a naphthofluorenylene group, a spirobifluorenylene group, a benzospirobifluorenylene group, a spiroanthracenylene group, or the like.
The heteroarylene group means a divalent group in which at least one carbon atom in the arylene group is substituted with a heteroatom. The heteroatom is selected from O, S, N, si, B, P, etc., but is not limited thereto. The heteroarylene group has from C2 to C60, preferably from C2 to C30, preferably from C2 to C25, preferably from C2 to C12, and more preferably from C2 to C7. The heteroarylene includes a monocyclic heteroarylene, a polycyclic heteroarylene, a fused ring heteroarylene, or a combination thereof. Examples of the heteroarylene group include, but are not limited to, dibenzofuranylene group, dibenzothiophenylene group, carbazolyl group, benzocarbazolylene group, spirofluorene xanthene group, spirofluorene thioxanthylene group, spirofluorene azaanthylene group, benzoxazolyl group, naphthoxazolyl group, benzothiazolyl group, naphthothiazolyl group, imidazolyl group, pyridinylene group, pyrimidinylene group, pyrazinylene group, pyridizylene group, triazinylene group, quinolinylene group, isoquinolylene group, quinazolinylene group, quinoxalylene group, naphthyridinylene group, phenanthrolinylene group, benzoquinolinylene group, benzisoquinolinylene group, and the like.
The term "subfused cyclic group of an alicyclic ring and an aromatic ring" as used herein means a general term in which an alicyclic ring and an aromatic ring are fused together, two hydrogen atoms are removed, and a divalent group remains. The alicyclic ring has a carbon number of C3 to C20, preferably C3 to C15, and more preferably C3 to C10. The aromatic ring has C6 to C30, preferably C6 to C25, more preferably C6 to C18, and still more preferably C6 to C12. Examples of the condensed-ene ring group of the alicyclic and aromatic rings include, but are not limited to, the groups described below, benzocyclobutene, dihydroindenyl, tetrahydronaphthyl, benzocycloheptyl, indenyl, dihydronaphthyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like, but are not limited thereto.
The term "condensed ring group of an alicyclic ring and a heteroaromatic ring" as used herein means a general term in which two hydrogen atoms are removed after the alicyclic ring and the heteroaromatic ring are condensed together to leave a divalent group. The alicyclic ring has a carbon number of C3 to C20, preferably C3 to C15, and more preferably C3 to C10. The heteroaromatic ring has from C2 to C30, preferably from C2 to C25, more preferably from C2 to C18, and even more preferably from C2 to C12 carbon atoms. Examples of the condensed ring group of the alicyclic and aromatic rings include, but are not limited to, the groups described below, pyridocyclopropyl ene, pyridocyclobutyl ene, pyridocyclopentyl ene, pyridocyclohexyl ene, pyridobenzocycloheptyl ene, pyrimidocyclobutyl ene, pyrimidocyclopentyl ene, pyrimidocyclohexyl ene, and the like, but are not limited thereto.
The invention provides an organic electroluminescent device, which comprises an anode, an organic layer and a cathode, wherein the organic layer is positioned between the anode and the cathode, the organic layer comprises a light-emitting layer, the light-emitting layer contains a first main material and a second main material, the first main material is a triarylamine compound shown in a formula 1, the second main material is a heterocyclic compound shown in a formula 2,
wherein, ar is 1 、Ar 2 Independently selected from one of the groups shown in the following,
a0 is an integer of 0 to 5; a1 is an integer of 0 to 4; the R is 1 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R 1 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 1 When each R is 1 Are the same or different from each other;
the La, lb, lc and L 1 、L 2 Independently selected from a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted C3-C20 alicyclic group and a C6-C30 aromatic ring-fused ring group; and said-La-Lb-Lc-is not a single bond;
a is selected from an integer of 0 to 4; r is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and fused ring group of C6-C30 aromatic ring, or two adjacent Rs are mutually bonded to form a substituted or unsubstituted ring; when a is 2 or more, each R is the same as or different from each other;
wherein Ar is selected from one of the groups shown in the specification,
the R is 0 The same or different is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substitutedOr one of unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C20 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted fused ring group of C3-C20 alicyclic ring and C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 lipoheterocyclic group, or two adjacent R 0 Bonded to each other to form a substituted or unsubstituted ring;
x is selected from O, S, C (R) x ) 2 、N(R x )、Si(R x ) 2 In a group of (A), the R x The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C20 alicyclic ring and C2-C30 heteroaromatic ring fused ring group, or two adjacent R groups x Bonded to each other to form a substituted or unsubstituted ring;
b0 is an integer of 0 to 4; b is an integer of 0 to 3; said R is 5 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 aliphatic heterocyclic group, or two adjacent R groups 5 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 5 When each R is 5 Are the same or different from each other;
said L 0 One selected from a single bond or a group shown below; n is an integer of 0 to 3; when n is 2 or more, each L 0 Are the same or different from each other;
n1 is an integer of 0 to 4; said R is 6 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 aliphatic heterocyclic group, or two adjacent R groups 6 Bonded to each other to form a substituted or unsubstituted ring; when n1 is 2 or more, each R 6 Are the same or different from each other;
said L 3 、L 4 Independently selected from a single bond, substituted or unsubstituted C3-C20 cycloalkylene, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused ring group, and substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic ring fused ring group;
the R is 3 、R 4 Independently selected from the group shown below,
said R is 7 One selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, and substituted or unsubstituted C3-C20 lipoheterocyclic group;
said X 1 Selected from O, S, N (R) x1 ) In a group of (A), the R x1 One selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, and substituted or unsubstituted C3-C20 lipoheterocyclic group;
the Y is the same or different and is selected from C (R) y ) Or N, said R y One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 lipoheterocyclic group, or two adjacent R groups y Bonded to each other to form a substituted or unsubstituted ring.
Preferably, said Ar 1 、Ar 2 Independently selected from one of the groups shown below,
a0 is an integer of 0 to 5; a1 is an integer of 0 to 4; a2 is an integer of 0 to 7; a3 is an integer of 0 to 9;
said R is 1 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R 1 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 1 When each R is 1 Are the same or different from each other;
the R is 10 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R 10 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 10 When each R is 10 Are the same or different from each other;
the Ra are the same or different and are selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and fused ring group of C6-C30 aromatic ring, or two adjacent Ra are mutually bonded to form a substituted or unsubstituted ring; when there are two or more Ra, each Ra is the same as or different from each other.
Preferably, ar is 1 、Ar 2 Independently selected from one of the groups shown below,
a0 is an integer of 0 to 5; a1 is an integer of 0 to 4; a2 is an integer of 0 to 7; a3 is an integer of 0 to 9; a4 is an integer of 0 to 6; a5 is an integer of 0 to 8; a6 is an integer of 0 to 10; a7 is an integer of 0 to 3; a8 is an integer of 0 to 12;
the R is 1 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring fused ring group, or two adjacent R 1 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 1 When each R is 1 Are the same or different from each other;
the R is 8 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and a fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring; when more than two R are present 8 When each R is 8 Are the same or different from each other;
said R is 10 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring fused ring group, or two adjacent R 10 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 10 When each R is 10 The same or different from each other.
Preferably, said R is 1 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C10 alicyclic ring and C6-C20 aromatic ring fused ring group, or two adjacent R 1 Bonded to each other to form a substituted or unsubstituted alicyclic ring; when more than two R are present 1 When each R is 1 The same or different from each other.
Preferably, ar is 1 、Ar 2 Independently selected from one of the groups shown below,
a0 is an integer of 0 to 5; a1 is an integer of 0 to 4; a2 is an integer of 0 to 7; a3 is an integer of 0 to 9; a4 is an integer of 0 to 6; a5 is an integer of 0 to 8; a6 is an integer of 0 to 10; a7 is an integer of 0 to 3; a8 is an integer of 0 to 12; a9 is an integer of 0 to 2;
the R is 1 One selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and a fused ring group of a substituted or unsubstituted C3-C10 alicyclic ring and a C6-C20 aromatic ring; when more than two R are present 1 When each R is 1 Are the same or different from each other;
the R is 8 One selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and a fused ring group of a substituted or unsubstituted C3-C10 alicyclic ring and a C6-C20 aromatic ring; when more than two R are present 8 When each R is 8 Are the same or different from each other;
the R is 10 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C10 alicyclic ring and C6-C20 aromatic ring fused ring group, or two adjacent R 10 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 10 When each R is 10 The same or different from each other.
The R is 11 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and a fused ring group of substituted or unsubstituted C3-C10 alicyclic ring and C6-C20 aromatic ring, or two adjacent R 11 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 11 When each R is 11 The same or different from each other.
It is preferable thatLa, lb, lc, L 1 、L 2 Independently selected from a single bond or one of the groups shown as the following; and said-La-Lb-Lc-is not a single bond;
m1 is an integer of 0 to 4; m2 is an integer of 0 to 6; m3 is an integer of 0 to 5; m4 is an integer of 0 to 8; m5 is an integer of 0 to 3;
the R is 2 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R 2 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 2 When each R is 2 Are the same or different from each other;
said R is 20 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R 20 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 20 When each R is 20 Are the same or different from each other;
the R is m The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring condensed ring group, or two adjacent R m Bonded to each other to form a substituted or unsubstituted ring;
said R is m0 The same or different is selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstitutedOne of substituted C3-C20 alicyclic ring and C6-C30 aromatic ring subfused cyclic group.
Preferably, said R is 2 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring fused ring group, or two adjacent R 2 Bonded to each other to form a substituted or unsubstituted alicyclic ring; when more than two R are present 2 When each R is 2 The same or different from each other.
Preferably, R is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring fused ring group, or two adjacent Rs are bonded to each other to form a substituted or unsubstituted ring; when a is 2 or more, each R is the same as or different from each other.
Preferably, R is selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptenyl, or two adjacent R's are bonded to each other to form a substituted or unsubstituted ring; when a is 2 or more, each R is the same as or different from each other; the substituents in the "substituted or unsubstituted" are selected from the group consisting of: hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, benzocycloalkyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, benzocyclobutenyl, indenyl, dihydronaphthyl.
Preferably, ar is selected from one of the groups shown as follows,
b0 is an integer of 0 to 4; b is an integer of 0 to 3; b1 is an integer of 0 to 5; b2 is an integer of 0 to 6; b3 is an integer of 0 to 8; b4 is an integer of 0 to 10; b5 is an integer of 0 to 12;
the R is 5 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C6-C25 aromatic ring, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C2-C25 heteroaromatic ring, substituted or unsubstituted C3-C15 lipoheterocyclic group, or two adjacent R 5 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 5 When each R is 5 Are the same or different from each other;
the R is 9 Selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstitutedOne of a substituted or unsubstituted C2-C25 heteroaryl group, a condensed ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C25 aromatic ring, a condensed ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C2-C25 heteroaromatic ring, and a substituted or unsubstituted C3-C15 alicyclic heterocyclic group; when more than two R are present 9 When each R is 9 Are the same or different from each other;
the R is x The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C6-C25 aromatic ring, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C2-C25 heteroaromatic ring, substituted or unsubstituted C3-C15 lipoheterocyclic group, or two adjacent R' s x Bonded to each other to form a substituted or unsubstituted ring.
Preferably, said L 0 One selected from a single bond or a group shown below; n is an integer of 0 to 3; when n is 2 or more, each L 0 Are the same or different from each other;
n1 is an integer of 0 to 4; n2 is an integer of 0 to 6;
the R is 6 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 lipoheterocyclic group, or two adjacent R groups 6 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 6 When each R is 6 Are identical or different from each otherThe same is true.
Preferably, said- (L) 0 ) n-is selected from a single bond or one of the groups shown as the following,
n1 is an integer of 0 to 4; n2 is an integer of 0 to 6;
said R is 6 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C6-C25 aromatic ring, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C2-C25 heteroaromatic ring, substituted or unsubstituted C3-C15 lipoheterocyclic group, or two adjacent R 6 Bonded to each other to form a substituted or unsubstituted alicyclic ring; when more than two R are present 6 When each R is 6 The same or different from each other.
Preferably, said L 3 、L 4 Independently selected from a single bond or one of the groups shown below,
the Z is the same or different and is selected from C (R) z ) Or N, said R z The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C20 alicyclic ring and C2-C30 heteroaromatic ring fused ring group, or two adjacent R groups z Bonded to each other to form a substituted or unsubstituted ring.
Preferably, said L 3 、L 4 Independently selected from a single bond or one of the groups shown below,
k1 is an integer of 0 to 4; k2 is an integer of 0 to 6; k3 is an integer of 0 to 3; k4 is an integer of 0 to 2; k5 is an integer of 0 to 5;
the R is z The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring fused ring group, substituted or unsubstituted C3-C15 alicyclic ring and C2-C25 heteroaromatic ring fused ring group, or substituted or unsubstituted C3-C15 lipoheterocyclic group, or two adjacent R z Bonded to each other to form a substituted or unsubstituted alicyclic ring.
Preferably, said R is 3 、R 4 Independently selected from one of the groups shown in the following,
the R is 7 Selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 fused ring of alicyclic ring and C6-C25 aromatic ring, substituted or unsubstituted C3-C15 fused ring and C2-C25 heteroaromatic ringAnd a substituted or unsubstituted C3-C15 alicyclic group;
the R is x1 One selected from the group consisting of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring fused ring group, substituted or unsubstituted C3-C15 alicyclic ring and C2-C25 heteroaromatic ring fused ring group, and substituted or unsubstituted C3-C15 alicyclic ring and C2-C25 heteroaromatic ring fused ring group;
c1 is an integer of 0 to 4; c2 is an integer of 0 to 3; c3 is an integer of 0 to 2; the R is y One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 lipoheterocyclic group, or two adjacent R groups y Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present y When each R is y The same or different from each other.
Preferably, said R is 3 、R 4 Independently selected from one of the groups shown in the following,
said R is 7 Selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, substituted or unsubstituted C3-C10 fused ring group of alicyclic ring and C6-C20 aromatic ring, substituted or unsubstituted C3-C10 fused ring group of alicyclic ring and C2-C20 heteroaromatic ring, substituted or unsubstituted C3-C1010, one of the lipoheterocyclic groups;
said R is x1 One selected from the group consisting of hydrogen, deuterium, tritium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted fused ring group of a C3-C10 alicyclic ring and a C6-C20 aromatic ring, a substituted or unsubstituted fused ring group of a C3-C10 alicyclic ring and a C2-C20 heteroaromatic ring, and a substituted or unsubstituted C3-C10 lipoheterocyclic group;
c1 is an integer of 0 to 4; c2 is an integer of 0 to 3; c3 is an integer of 0 to 2; c4 is an integer of 0 to 6; c5 is an integer of 0 to 8;
said R is y One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C6-C25 aromatic ring, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C2-C25 heteroaromatic ring, substituted or unsubstituted C3-C15 lipoheterocyclic group, or two adjacent R y Bonded to each other to form a substituted or unsubstituted alicyclic ring; when more than two R are present y When each R is y The same or different from each other.
Preferably, the triarylamine compound represented by formula 1 is selected from at least one of the structures shown below,
some specific chemical structures of the triarylamine compound represented by formula 1 of the present invention are listed above, but the present invention is not limited to these listed chemical structures, and any substituent group having the above-defined substituent group is included on the basis of the structure represented by formula 1.
Preferably, the heterocyclic compound represented by the formula 2 is selected from at least one of the following structures,
some specific chemical structures of the heterocyclic compound represented by formula 2 of the present invention are listed above, but the present invention is not limited to these listed chemical structures, and any substituent group as defined above based on the structure represented by formula 2 should be included.
Preferably, the light-emitting layer further contains a dopant.
The functional layer of the organic electroluminescent device of the present invention may further contain one or more of the following functional layers, a hole transporting region, an electron transporting region, a cover layer, and the like. All functional layers having hole injecting and/or transporting properties, electron injecting and/or transporting properties or light extracting properties are included. The hole transport region of the present invention includes at least one of a hole injection layer, a hole transport layer, a light emission assisting layer, an electron blocking layer, and the like. The electron transport region of the present invention includes at least one of a hole blocking layer, an electron transport layer, an electron injection layer, and the like. In general, the hole transport region and the electron transport region are located between the anode and the cathode, and the cover layer is located outside the cathode or the anode. Each functional layer may be formed of a single layer film or a plurality of layers of films, and each layer of film may be formed of only one material or a plurality of materials.
The material of each layer of the thin film in the organic electroluminescent device of the present invention is not particularly limited, and those known in the art can be used. The organic functional layers of the above-mentioned organic electroluminescent device and the electrodes on both sides of the device are described below:
the anode of the invention has the function of smoothly injecting holes into the organic matter layer, and is composed of materials with higher work function. The anode includes, but is not limited to, materials such as metals or alloys thereof, metal oxides, combinations of metals and oxides, laminates, conductive polymers, and the like. Specific examples may include gold (Au), chromium (Cr), copper (Cu), vanadium (V), aluminum (Al), indium Tin Oxide (ITO), indium Zinc Oxide (IZO), zinc oxide: aluminum (ZnO: al), indium tin oxide/silver/indium tin oxide (ITO/Ag/ITO), polypyrrole, and the like, but are not limited thereto.
The cathode of the invention has the function of smoothly injecting electrons into the organic layer and is composed of a material with a lower work function. The cathode includes, but is not limited to, materials described below, metals or alloys thereof, laminates, and the like. Specific examples may include aluminum silver (Ag), aluminum (Al), tin (Sn), lead (Pb), magnesium/silver (Mg/Ag), lithium fluoride/aluminum (LiF/Al), lithium oxide/aluminum (Li) 2 O/Al), etc., but are not limited thereto.
The hole injection layer of the present invention functions to reduce the interface barrier between the anode and the hole transport layer. The hole injection layer includes, but is not limited to, phthalocyanine metal complexes, polycyano conjugated organics, radialene compounds, arylamine derivatives, polymers, and the like. Specific examples may include copper phthalocyanine (CuPC), 4,4' - (1E,1 ' E) - (2-cyano-3, 6-difluoro-5-isocyanocyclohexane-2, 5-diene-1, 4-diylidene) bis (cyanomethyl-1-yl-1-ylidene) bis (2, 3,5, 6-tetrafluorobenzonitrile), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN), 2,3,5, 6-tetrafluoro-7, 7',8,8' -tetracyanoldimethylp-benzoquinone (F4-TCNQ), 4' -bis [ N- [9- (2-naphthyl) carbazol-3-yl ] -N-phenylamino ] -1,1' -biphenyl, 4' -tris (N- (1-naphthyl) -N-phenyl-amino) -triphenylamine (1-TNATA), 4', 4' -tris (N, N-2-naphthylphenylamino) triphenylamine (2-TNATA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), and the like, but are not limited thereto.
The hole transport layer of the present invention serves to improve the balance of injection and transport of holes of the device. The hole transport layer includes, but is not limited to, materials such as arylamine derivatives, carbazole derivatives, polymers, and the like. Specific examples may include N, N ' -diphenyl-N, N ' -bis (2-naphthyl) -1,1' -biphenyl-4, 4' -diamine (β -NPB), N- ([ 1,1' -biphenyl ] -4-yl) -N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) - [1,1' -biphenyl ] -4-amine, N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), 1,3, 5-tris (9-carbazolyl) benzene (TCB), poly (N-vinylcarbazole) (PVK), and the like, but are not limited thereto.
The electron blocking layer of the invention has the function of blocking electrons in the light emitting layer, so that the electrons and holes are effectively combined in the light emitting layer. The electron blocking layer includes, but is not limited to, materials described below, aromatic amine derivatives, carbazole derivatives, and the like. Specific examples may include N-phenylcarbazole, 4',4 ″ -tris (N-carbazolyl) triphenylamine (TCTA), 4' -cyclohexylidenebis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), N '-bis (naphthalen-1-yl) -N, N' -diphenyl-benzidine (NPD), and the like, but are not limited thereto.
The light-emitting layer comprises a host material and a doping material, and the light-emitting material can be a red light-emitting material, a green light-emitting material, a blue light-emitting material or a combination thereof. The doping ratio of the host material and the dopant material may vary depending on the material used, and the doping ratio of the dopant material is usually 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.
The host material of the light-emitting layer needs to have a bipolar charge transport property and also needs to have an appropriate energy level to efficiently transfer excitation energy to the guest light-emitting material. The main material can be one material or can be a single materialIs made of more than two materials. Preferred are triarylamine compounds of formula 1 and heterocyclic compounds of formula 2 according to the present invention. The host material includes, but is not limited to, heterocyclic compounds, metal complexes, fused aromatic ring derivatives, silicon-containing compounds, etc., and specific examples may include 9- [4- (tert-butyl) phenyl]-3, 6-bis (triphenylmethyl) -9H-carbazole (CzC), 4 '-bis (carbazol-9-yl) biphenyl (CBP), 4' -tris (N-carbazolyl) triphenylamine (TCTA), zinc 8-hydroxyquinoline salt (Znq) 2 ) Tris (6-fluoro-8-quinolinolato) aluminum (6 FAlq) 3 ) 9, 10-bis (2-naphthyl) Anthracene (ADN), 2-tert-butyl-9, 10-bis (2-naphthyl) anthracene (TBADN)), 9-bis [4- (1-pyrenyl) phenyl group]Fluorene (DPPF), 2- [9, 9-bis (4-methylphenyl) -fluoren-2-yl]-9, 9-bis (4-methylphenyl) fluorene (BDAF), 9- (4-tert-butylphenyl) -3, 6-bis (triphenylsilyl) -9H-carbazole (CzSi), and the like, but are not limited thereto. The weight ratio of the first host material to the second host material in the present invention is 1.
The dopant material may be a fluorescent material, a phosphorescent material, a TADF material, or a combination thereof. The doping material includes, but is not limited to, a metal complex, a fused aromatic compound, a styrylamine compound, an aromatic amine derivative, a heterocyclic compound, and the like. Specific examples may include bis (3, 5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III) (FIrPic), tris (2- (3, 5-dimethylphenyl) quinoline-C2, N') iridium (III) (Ir (dmpq) 3 ) Bis (2- (3, 5-dimethylphenyl) quinoline-C2, N') (acetylacetonato) iridium (III) (Ir (mphq) 2 acac), bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy) 2 (acac)), tris [2- (p-tolyl) pyridine]Iridium (III) (Ir (mppy) 3 )、N 1 ,N 1 ,N 6 ,N 6 Tetra ([ 1,1' -biphenyl)]-3-yl) pyrene-1, 6-diamine, N 1 ,N 6 Bis (6- (tert-butyl) dibenzo [ b, d]Furan-4-yl) -N1, N6-di-m-methylphenyl-pyrene-1, 6-diamine, 2,5,8, 11-tetra-tert-butylperylene (TBPe), N, N, N ', N ' -tetra (4-methylphenyl) - [9,9' -bianthracene]10,10 '-diamine (BA-TTB), 4' -bis [4- (di-p-tolylamino) styryl]Biphenyl (DPAVBi), 4' -bis (4- (9H-carbazol-9-yl) phenethyl esterAlkenyl) biphenyl (BSB 4), 2, 8-di-tert-butyl-5, 11-bis (4-tert-butylphenyl) -6, 12-diphenyltetradecene (TBRb), 4- (dicyanovinyl) -2-tert-butyl-6- (1, 7-tetramethyljulidinyl-4-vinyl) -4H-pyran (DCJTB), coumarin 6 and the like, but is not limited thereto.
The hole blocking layer of the present invention functions to block holes in the light emitting layer, and to allow holes and electrons to be effectively recombined in the light emitting layer. The hole blocking layer includes, but is not limited to, oxadiazole derivatives, triazole derivatives, imidazole derivatives, phenanthroline derivatives, metal complexes, and the like. Specific examples may include 2, 9-bis (naphthalen-2-yl) -4, 7-diphenyl-1, 10-phenanthroline (NBphen), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), and the like, but are not limited thereto.
The electron transport layer of the present invention functions to improve the balance of injection and transport of electrons of the device. The electron transport layer includes, but is not limited to, materials, metal complexes, heteroaromatic compounds, polymers, and the like as described below. Specific examples may include tris (8-quinolinato) aluminum (III) (Alq) 3 ) 8- (4, 6-bis (naphthalen-2-yl) -1,3, 5-triazin-2-yl) phenyl) quinoline, 1, 3-bis [2- (2, 2' -bipyridin-6-yl) -1,3, 4-oxadiazol-5-yl]Benzene (Bpy-OXD), 3, 5-diphenyl-4- (1-naphthyl) -1,2, 4-triazole (NTAZ), 2,9- (dimethyl) -4, 7-biphenyl-1, 10-phenanthroline (BCP), 3' - [5', 5' -bis [3- (4-pyridyl) phenyl ] methyl][1,1':3',1":3", 1' "-quaterphenyl]-3, 3' -diyl]Bipyridine (BP 4 mPy), poly [ (9, 9-dioctylfluorene-2, 7-diyl) -co- (2, 2 '-bipyridine-6, 6' -diyl)](PF-BPy), etc., but are not limited thereto.
The electron injection layer of the present invention functions to reduce the interfacial barrier between the cathode and the electron transport layer. The electron injection layer material includes, but is not limited to, materials described below, metals, metal compounds, metal oxides, and the like. Specific examples may include lithium (Li), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), cesium carbonate (Cs) 2 CO 3 ) Lithium oxide (Li) 2 O), etc., but are not limited thereto.
The method for preparing each layer of the thin film in the organic electroluminescent device of the present invention is not particularly limited, and vacuum evaporation, sputtering, spin coating, spray coating, screen printing, laser transfer printing, and the like can be used, but is not limited thereto.
The organic electroluminescent device is mainly applied to the technical field of information display, and is widely applied to various information displays in the aspect of information display, such as tablet computers, flat televisions, mobile phones, smart watches, digital cameras, VR, vehicle-mounted systems, wearable equipment and the like.
Synthetic examples
The method for preparing the triarylamine compound represented by formula 1 of the present invention is not particularly limited, and conventional methods well known to those skilled in the art may be used. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc., the triarylamine compound represented by formula 1 of the present invention can be prepared by the following synthetic route.
The method for preparing the heterocyclic compound represented by formula 2 of the present invention is not particularly limited, and conventional methods well known to those skilled in the art may be employed. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc., the heterocyclic compound represented by formula 2 of the present invention can be prepared by the following synthetic route.
(1) When R is 3 -L 3 -, and R 4 -L 4 The same, the synthetic route of formula 2 is as follows:
(2) When R is 3 -L 3 -, and R 4 -L 4 When different, the synthetic route of formula 2 is as follows:
the Xn is halogen, for example, the Xn is the same or different and is selected from Cl, br and I;
the Bn is the same or different and is selected from
*-B(OH) 2 And so on.
Raw materials and reagents: the starting materials and reagents used in the following synthetic examples are not particularly limited, and may be commercially available products or prepared by methods known to those skilled in the art. The raw materials and reagents used in the invention are all pure reagents.
The instrument comprises: G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer (waters, uk); a Vario EL cube type organic element analyzer (Elementar Co., germany).
Synthesis example 1
Synthesis A-12:
under the protection of nitrogen, adding alpha-12 (120.00mmol, 20.07g), 1, 10-phenanthroline (24.00mmol, 4.32g) and anhydrous K into a reaction bottle 3 PO 4 (240.00mmol, 50.94g), b-12 (120.00mmol, 22.97g), DMSO (350.00 ml), cuI (24.00mmol, 4.57g), stirred under heating, and reacted for 24 hours under reflux. After the reaction is finished, cooling the reaction liquid to room temperature, adding water for quenching, extracting by using chloroform, adding a small amount of activated carbon into an organic phase, heating and refluxing for 0.5 hour for decoloring, filtering, removing a solvent under reduced pressure, and then performing column chromatography, wherein the mobile phase is dichloromethane: petroleum ether (1.
Synthesis of B-12:
a-12 (80.00mmol, 22.22g), c-12 (80.00mmol, 13.54g), sodium tert-butoxide (120.00mmol, 11.53g), toluene (250.00 mL), palladium acetate (0.80mmol, 180mg), tri-tert-butylphosphine (1.20mmol, 243mg) were added to a reaction flask under nitrogen protection, stirred and dissolved, and reacted for 5 hours under reflux. After completion of the reaction, the reaction solution was cooled to room temperature, water was added, extraction was performed with dichloromethane, the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure, and recrystallization was performed with toluene: methanol = 81 to obtain B-12 (24.30 g, yield 74%), and purity of solid was 99.84% or more by HPLC.
Synthesis of 1-12:
under the protection of nitrogen, B-12 (40.00mmol, 16.42g), d-12 (40.00mmol, 8.52g), sodium tert-butoxide (80.00mmol, 7.69g), toluene (200.00 mL), dibenzylideneacetone dipalladium (0.40mmol, 366 mg) and tri-tert-butylphosphine (0.80mmol, 162mg) were added to a reaction flask, dissolved by stirring, and reacted for 8 hours under reflux. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, extraction was performed with chloroform, the organic phase was dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallization was performed with toluene to obtain compounds 1-12 (17.15 g, yield 79%) having a solid purity of 99.93% or more by HPLC. Mass spectrum m/z:542.2733 (theoretical value: 542.2722). Theoretical element content (%) C 40 H 34 N 2 : c,88.52; h,6.31; and N,5.16. Measured elemental content (%): c,88.56; h,6.33; and N,5.13.
Synthesis example 2
By following the same preparation procedures as 1 to 12 in Synthesis example 1, replacing a-12 with equimolar a-26, b-12 with equimolar b-135, d-12 with equimolar d-135, 1 to 135 (24.97 g) was obtained, which had a solid purity of 99.94% or more as determined by HPLC. Mass spectrum m/z:878.3651 (theoretical value: 878.3661). Theoretical element content (%) C 67 H 46 N 2 : c,91.54; h,5.27; n,3.19. Measured elemental content (%): c,91.51; h,5.29; and N,3.18.
Synthesis example 3
According to the same preparation method as 1-12 in Synthesis example 1Method, replacing a-12 with equimolar a-142, b-12 with equimolar b-142, d-12 with equimolar d-142, gives 1-189 (20.21 g), with a solid purity of 99.92% or more by HPLC. Mass spectrum m/z:688.2647 (theoretical value: 688.2627). Theoretical element content (%) C 50 H 32 N 4 : c,87.18; h,4.68; and N,8.13. Measured elemental content (%): c,87.21; h,4.65; and N,8.15.
Synthesis example 4
By following the same preparation method as 1-12 in Synthesis example 1, substituting b-12 for equimolar b-189, d-12 for equimolar d-189, 1-189 (20.21 g) was obtained, which had a solid purity of 99.94% or more by HPLC. Mass spectrum m/z:664.3685 (theoretical value: 664.3694). Theoretical element content (%) C 49 H 32 D 8 N 2 : c,88.51; h,7.27; n,4.21. Measured elemental content (%): c,88.55; h,7.25; n,4.19.
Synthesis example 5
According to the same preparation method as that of 1-12 in Synthesis example 1, a-12 was replaced with equimolar a-494, b-12 was replaced with equimolar b-494, c-12 was replaced with equimolar c-494, d-12 was replaced with equimolar d-494, to give 1-494 (22.48 g) with a solid purity of 99.95% or more as measured by HPLC. Mass spectrum m/z:769.3518 (theoretical value: 769.3505). Theoretical element content (%) C 58 H 35 D 5 N 2 : c,90.47; h,5.89; and N,3.64. Measured elemental content (%): c,90.45; h,5.86; and N,3.68.
Synthesis example 6
According to the same procedures as those described in 1 to 12 of Synthesis example 1The preparation method comprises the steps of replacing b-12 with equimolar b-524, replacing c-12 with equimolar c-524, replacing d-12 with equimolar d-524 to obtain 1-524 (22.09 g), and detecting the solid purity by HPLC (high performance liquid chromatography) to be more than or equal to 99.89%. Mass spectrum m/z:788.3183 (theoretical value: 788.3191). Theoretical element content (%) C 60 H 40 N 2 : c,91.34; h,5.11; and N,3.55. Measured elemental content (%): c,91.32; h,5.16; n,3.51.
Synthesis example 7
According to the same preparation method as 1-12 in Synthesis example 1, b-12 was replaced with equimolar b-539, c-12 was replaced with equimolar c-539, and d-12 was replaced with equimolar d-539 to give 1-539 (23.46 g) having a solid purity of 99.91% or more as measured by HPLC. Mass spectrum m/z:781.3517 (theoretical value: 781.3505). Theoretical element content (%) C 59 H 35 D 5 N 2 : c,90.62; h,5.80; and N,3.58. Measured elemental content (%): c,90.59; h,5.85; and N,3.56.
Synthesis example 8: preparation of Compounds 2-5
Preparation of intermediate F-5:
under the protection of nitrogen, the intermediate e-5 (33.64g, 110.00mmol), the raw material pinacol diboron ester (30.73g, 121.00mmol) and Pd (dppf) Cl are added into a reaction bottle in sequence 2 (1.84g, 2.51mmol), KOAc (21.59g, 220.00mmol) and 1, 4-dioxane (520 mL) were stirred, the above reactant system was heated under reflux for 4.5 hours, after completion of the reaction, 780mL of distilled water was added thereto after cooling to room temperature, extraction was performed with ethyl acetate, and the organic layer was extracted with anhydrous MgSO 4 Drying, rotary evaporation to remove ethyl acetate, and then recrystallization from toluene gave intermediate F-5 (34.09 g, 78% yield); HPLC purity is more than or equal to 98.66 percent.
Preparation of intermediate G-5:
under the protection of nitrogen, the intermediate F-5 (28.38g, 71.43mmol), the raw material g-5 (15.81g, 70.00mmol) and Pd (dppf) Cl are added into a reaction bottle in sequence 2 (0.77g，1.05mmol)、Na 2 CO 3 (14.84g, 140.00mmol) and 210mL of toluene, 70mL of ethanol and 70mL of water, stirring the mixture, and heating the reactant system to reflux for reaction for 6 hours; after the reaction is finished, cooling to room temperature, performing suction filtration to obtain a filter cake, washing the filter cake with ethanol, and finally, adding toluene/methanol =7:1 recrystallisation to give intermediate G-5 (22.44G, 77% yield); HPLC purity is more than or equal to 98.71 percent.
Preparation of intermediate H-5:
under the protection of nitrogen, the intermediate G-5 (18.74g, 45.00mmol), the raw material pinacol diboron ester (25.14g, 99.00mmol) and Pd (dppf) Cl are added into a reaction bottle in sequence 2 (1.98g, 2.70mmol), KOAc (17.67g, 180.00mmol), and 1, 4-dioxane (450 mL) and the mixture was stirred to heat-reflux the above reactant system for 7.5 hours; after the reaction was completed, the mixture was cooled to room temperature, 700mL of distilled water was added thereto, followed by extraction with ethyl acetate, and the organic layer was separated with anhydrous MgSO 4 Drying, rotary evaporation to remove ethyl acetate, then recrystallization with toluene, drying to obtain intermediate H-5 (19.42 g, yield 72%); HPLC purity is more than or equal to 98.89%.
Preparation of Compounds 2-5:
under the protection of nitrogen, the intermediate H-5 (17.98g, 30.00mmol), the raw material H-5 (12.18g, 61.50mmol) and Pd were sequentially added into a reaction bottle 2 (dba) 3 (0.55g，0.60mmol)、P(t-Bu) 3 (2.4 mL of a 0.5M solution in toluene, 1.2 mmol), K 2 CO 3 (120.00mmol, 16.59g) and 120ml of tetrahydrofuran, stirring the mixture, and heating and refluxing the reactant system for 8 hours; after the reaction is finished, cooling to room temperature, performing suction filtration to obtain a filter cake, washing the filter cake with ethanol, and finally recrystallizing the filter cake with toluene to obtain a compound 2-5 (13.26 g, yield 76%); the HPLC purity is more than or equal to 99.83 percent. Mass spectrum m/z:581.2112 (theoretical value: 581.2103). Theoretical element content (%) C 40 H 27 N 3 O 2 : c,82.60; h,4.68; and N,7.22. Measured elemental content (%): c,82.63; h,4.64; n is a radical of hydrogen,7.24。
Synthesis example 9: preparation of Compounds 2-19
Preparation of intermediate E-19:
under the protection of nitrogen, raw material e-19 (35.56g, 110.00mmol), raw material f-19 (17.54g, 112.20mmol) and Pd (PPh) were sequentially added into a reaction flask 3 ) 4 (2.54g，2.20mmol)、K 2 CO 3 (30.41g, 220.00mmol) and 330mL of toluene, 110mL of ethanol, 110mL of water, stirring the mixture, and heating the reactant system to reflux for reaction for 3.5 hours; after the reaction is finished, cooling to room temperature, performing suction filtration to obtain a filter cake, washing the filter cake with ethanol, and finally, adding toluene/methanol =6:1 recrystallisation gave intermediate E-19 (32.40 g, 83% yield); HPLC purity is more than or equal to 98.69 percent.
According to the same production method as that of Synthesis example 1, compound 2-5 was prepared by substituting equimolar amounts of E-5 and h-5 for equimolar amounts of E-19 and h-19, respectively, to give Compound 2-19 (17.38 g) having an HPLC purity of 99.93% or higher. Mass spectrum m/z:782.2945 (theoretical value: 782.2933). Theoretical element content (%) C 57 H 38 N 2 O 2 : c,87.44; h,4.89; and N,3.58. Measured elemental content (%): c,87.42; h,4.86; and N,3.60.
Synthesis example 10: preparation of Compounds 2-28
According to the same production method as that of Compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-28, f-28 and h-28, respectively, to give Compounds 2 to 28 (13.77 g) with an HPLC purity of 99.95% or higher. Mass spectrum m/z:732.3731 (theoretical value: 732.3716). Theoretical element content (%) C 52 H 48 N 2 O 2 : c,85.21; h,6.60; and N,3.82. Measured elemental content (%): c,85.18; h,6.62; and N,3.80.
Synthesis example 11: preparation of Compounds 2-47
According to the same production method as that of Compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-47, f-47 and h-5, respectively, to give Compounds 2 to 47 (17.32 g) with an HPLC purity of 99.94% or higher. Mass spectrum m/z:790.3570 (theoretical value: 790.3559). Theoretical element content (%) C 57 H 46 N 2 O 2 : c,86.55; h,5.86; n,3.54. Measured elemental content (%): c,86.58; h,5.82; n,3.51.
Synthesis example 12: preparation of Compounds 2-55
According to the same production method as that of Compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-55, f-55 and h-5, respectively, to give Compounds 2 to 55 (13.78 g) with an HPLC purity of 99.95% or higher. Mass spectrum m/z:656.2452 (theoretical value: 656.2464). Theoretical element content (%) C 47 H 32 N 2 O 2 : c,85.95; h,4.91; and N,4.27. Measured elemental content (%): c,85.92; h,4.93; and N,4.25.
Synthesis example 13: preparation of Compounds 2-72
According to the same production method as that of compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-72, f-72 and h-5, respectively, to give compounds 2 to 72 (14.37 g) in an HPLC purity ≧ 99.94%. Mass spectrum m/z:656.2451 (theoretical value: 656.2464). Theoretical element content (%) C 47 H 32 N 2 O 2 : c,85.95; h,4.91; and N,4.27. Measured elemental content (%): c,85.98; h,4.93; and N,4.23.
Synthesis example 14: preparation of Compounds 2-79
According to the same preparation method as that of compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and g-5 were replaced with equimolar amounts of e-79, f-72 and g-79, respectively, to give compound 2 to 79 (18.44 g) with an HPLC purity of 99.95% or higher. Mass spectrum m/z:808.3098 (theoretical value: 808.3090). Theoretical element content (%) C 59 H 40 N 2 O 2 : c,87.60; h,4.98; and N,3.46. Measured elemental content (%): c,87.63; h,4.97; and N,3.48.
Synthesis example 15: preparation of Compounds 2-87
According to the same production method as that for compounds 2 to 19 of Synthesis example 9, by substituting equal moles of e-19 and f-19 for equal moles of e-87 and f-87, respectively, compound 2 to 87 (18.36 g) was obtained with an HPLC purity of 99.92% or more. Mass spectrum m/z:815.3542 (theoretical value: 815.3529). Theoretical element content (%) C 59 H 33 D 7 N 2 O 2 : c,86.84; h,5.80; n,3.43. Measured elemental content (%): c,86.87; h,5.78; and N,3.46.
Synthesis example 16: preparation of Compounds 2-98
According to the same production method as that of Compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-28, f-47 and h-98, respectively, to give Compounds 2 to 98 (17.47 g) with an HPLC purity of 99.96% or higher. Mass spectrum m/z:810.2981 (theoretical value: 810.2995). Theoretical element content (%) C 57 H 38 N 4 O 2 : c,84.42; h,4.72; and N,6.91. Measured elemental content (%): c,84.46; h,4.70; and N,6.88.
Synthesis example 17: preparation of Compounds 2 to 99
According to the same production method as that for compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-28, f-47 and h-99, respectively, to give compounds 2 to 99 (17.01 g) in HPLC purity ≧ 99.91%. Mass spectrum m/z:812.2926 (theoretical value: 812.2900). Theoretical element content (%) C 55 H 36 N 6 O 2 : c,81.26; h,4.46; n,10.34. Measured elemental content (%): c,81.22; h,4.44; n,10.37.
Synthesis example 18: preparation of Compounds 2-107
According to the same production method as that of Compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-28, f-107 and h-107, respectively, to give Compounds 2 to 107 (18.49 g) with an HPLC purity of 99.94% or higher. Mass spectrum m/z:810.2981 (theoretical value: 810.2995). Theoretical element content (%) C 57 H 38 N 4 O 2 : c,84.42; h,4.72; and N,6.91. Measured elemental content (%): c,84.45; h,4.70; and N,6.94.
Synthesis example 19: preparation of Compounds 2 to 126
According to the same production method as that of Compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-28, f-47 and h-126, respectively, to give Compound 2 to 126 (18.17 g) with an HPLC purity of 99.95% or higher. Mass spectrum m/z:840.2641 (theoretical value: 840.2633). Theoretical element content (%) C 59 H 40 N 2 S 2 : c,84.25; h,4.79; n,3.33. Measured elemental content (%): c,84.28; h,4.75; and N,3.35.
Synthesis example 20: preparation of Compounds 2-138
By following the same procedures as in Synthesis examples 9, compounds 2 to 138 (16.27 g) were obtained by substituting equimolar amounts of e-19, f-19 and h-19 for equimolar amounts of e-28, f-138 and h-5, respectively, and had HPLC purity ≧ 99.93%. Mass spectrum m/z:732.2762 (theoretical value: 732.2777). Theoretical element content (%) C 53 H 36 N 2 O 2 : c,86.86; h,4.95; and N,3.82. Measured elemental content (%): c,86.83; h,4.97; n,3.84.
Synthesis example 21: preparation of Compounds 2 to 150
According to the same production method as that of Compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-28, f-150 and h-150, respectively, to give Compounds 2 to 150 (16.52 g) with an HPLC purity of 99.91% or higher. Mass spectrum m/z:7642334 (theoretical: 764.2320). Theoretical element content (%) C 53 H 36 N 2 S 2 : c,83.21; h,4.74; and N,3.66. Measured elemental content (%): c,83.25; h,4.72; n,3.63.
Synthesis example 22: preparation of Compounds 2-176
According to the same production method as that of Synthesis example 9, compounds No. 2 to 176 (19.02 g) were obtained by substituting equimolar amounts of e-19, f-19 and h-19 for equimolar amounts of e-72, f-176 and h-176, respectively, and the HPLC purity was ≧ 99.96%. Mass spectrum m/z:892.2682 (theoretical value: 892.2694). Theoretical element content (%) C 61 H 40 N 4 S 2 : c,82.03; h,4.51; and N,6.27. Measured elemental content (%): c,82.06; h,4.53; and N,6.24.
Synthesis example 23: preparation of Compounds 2-329
According to the same production method as that of compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-329, f-329 and h-150, respectively, to give compounds 2 to 329 (18.13 g) in HPLC purity ≧ 99.92%. Mass spectrum m/z:862.2489 (theoretical value: 862.2476). Theoretical element content (%) C 61 H 38 N 2 S 2 : c,84.89; h,4.44; and N,3.25. Measured elemental content (%): c,84.86; h,4.42; and N,3.28.
Synthesis example 24: preparation of Compounds 2-355
According to the same production method as that of Compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-355, f-355 and h-355, respectively, to give Compound 2 to 355 (19.43 g) with an HPLC purity of not less than 99.94%. Mass spectrum m/z:886.2465 (theoretical value: 886.2476). Theoretical element content (%) C 63 H 38 N 2 S 2 : c,85.30; h,4.32; and N,3.16. Measured elemental content (%): c,85.33; h,4.30; and N,3.18.
Synthesis example 25: preparation of Compounds 2-432
According to the same production method as that of Compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19 were replaced with equimolar amounts of e-432, respectively, to give compounds 2 to 432 (19.08 g) with HPLC purity ≧ 99.96%. Mass spectrum m/z:856.3097 (theoretical value: 856.3090). Theoretical element content (%) C 63 H 40 N 2 O 2 : c,88.29; h,4.70; and N,3.27. Measured elemental content (%): c,88.25; h,4.73; and N,3.23.
Synthesis example 26: preparation of Compounds 2-446
According to the same production method as that of Compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-446, f-47 and h-150, respectively, to give Compound 2-446 (18.05 g) with an HPLC purity of 99.97% or higher. Mass spectrum m/z:812.2311 (theoretical value: 812.2320). Theoretical element content (%) C 57 H 36 N 2 S 2 : c,84.20; h,4.46; and N,3.45. Measured elemental content (%): c,84.23; h,4.42; n,3.42.
Synthesis example 27: preparation of Compounds 2-478
According to the same production method as that of Compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-478, f-47 and h-5, respectively, to give Compounds 2 to 478 (16.18 g) with an HPLC purity of 99.95% or higher. Mass spectrum m/z:748.3099 (theoretical value: 748.3090). Theoretical element content (%) C 54 H 40 N 2 O 2 : c,86.60; h,5.38; n,3.74. Measured elemental content (%): c,86.64; h,5.34; n,3.77.
Synthesis example 28: preparation of Compounds 2-512
According to the same production method as that for compounds 2 to 19 of Synthesis example 9, equimolar amounts of e-19, f-19 and h-19 were replaced with equimolar amounts of e-512, f-47 and h-512, respectively, to give compound 2 to 512 (19.23 g) having an HPLC purity of 99.94% or more. Mass spectrum m/z:928.2959 (theoretical value: 928.2946). Theoretical element content (%) C 66 H 44 N 2 S 2 : c,85.31; h,4.77; and N,3.01. Measured elemental content (%): c,85.34; h,4.75; and N,3.03.
Device embodiments
In the invention, the ITO/Ag/ITO or ITO glass substrate is ultrasonically cleaned for 2 times and 20 minutes each time by 5% glass cleaning liquid, and then ultrasonically cleaned for 2 times and 10 minutes each time by deionized water. Ultrasonic cleaning with acetone and isopropanol for 20 min, and oven drying at 120 deg.C. The organic materials are sublimated, and the purity of the organic materials is over 99.99 percent.
The driving voltage, the luminous efficiency and the CIE color coordinate of the organic electroluminescent device are tested by combining test software, a computer, a K2400 digital source meter manufactured by Keithley of the United states and a PR788 spectral scanning luminance meter manufactured by Photo Research of the United states into a combined IVL test system. The lifetime was measured using the M6000 OLED lifetime test system from McScience. The environment for testing is atmospheric environment, and the temperature is room temperature.
Example 1: preparation of organic electroluminescent device 1
Vacuum evaporating 1-TNATA on the ITO anode to form a hole injection layer with the thickness of 60nm; vacuum evaporating beta-NPB on the hole injection layer to form a hole transport layer with the thickness of 41nm; first host compounds 1 to 12 and second host compounds 2 to 226 were vacuum-evaporated on the hole transport layer at a mass ratio of 1 2 The acac was evaporated in a doping amount of 4wt% based on the total amount of the host and the dopant to form a light emitting layer with a thickness of 50nm; NBphen is evaporated on the luminescent layer in vacuum and serves as a hole blocking layer, and the thickness is 6nm; vacuum evaporation of Alq on hole blocking layer 3 As an electron transport layer, the thickness is 22nm; evaporating LiF on the electron transport layer in vacuum to form an electron injection layer, wherein the evaporation thickness is 1.1nm; al is vacuum-evaporated on the electron injection layer to form a cathode with a thickness of 160nm.
Examples 2 to 35: preparation of organic electroluminescent devices 2 to 35
The first host compounds 1 to 12 in the light-emitting layer of example 1 were replaced with compounds 1 to 25, compounds 1 to 32, compounds 1 to 37, compounds 1 to 61, compounds 1 to 71, compounds 1 to 81, compounds 1 to 109, compounds 1 to 127, compounds 1 to 130, compounds 1 to 149, compounds 1 to 156, compounds 1 to 175, compounds 1 to 199, compounds 1 to 204, compounds 1 to 218, compounds 1 to 220, compounds 1 to 230, compounds 1 to 249, compounds 1 to 275, compounds 1 to 280, compounds 1 to 302, compounds 1 to 309, compounds 1 to 319, compounds 1 to 320, compounds 1 to 325, compounds 1 to 370, compounds 1 to 476, compounds 1 to 585, compounds 1 to 670, compounds 1 to 701, compounds 1 to 708, compounds 1 to 758, compounds 1 to 774, compounds 1 to 815, respectively; the second host compounds 2 to 226 in the light-emitting layer were replaced with compounds 2 to 82, compounds 2 to 446, compounds 2 to 228, compounds 2 to 8, compounds 2 to 211, compounds 2 to 5, compounds 2 to 432, compounds 2 to 21, compounds 2 to 22, compounds 2 to 28, compounds 2 to 360, compounds 2 to 150, compounds 2 to 16, compounds 2 to 18, compounds 2 to 478, compounds 2 to 79, compounds 2 to 687, compounds 2 to 13, compounds 2 to 12, compounds 2 to 83, compounds 2 to 99, compounds 2 to 158, compounds 2 to 138, compounds 2 to 64, compounds 2 to 73, compounds 2 to 250, compounds 2 to 55, compounds 2 to 19, compounds 2 to 355, compounds 2 to 705, compounds 2 to 721, compounds 2 to 329, compounds 2 to 176, and compounds 2 to 33, respectively, and the other steps were the same, thereby obtaining organic electroluminescent devices 2 to 35.
Comparative example 1: preparation of comparative organic electroluminescent device 1
Vacuum evaporating 1-TNATA on the ITO anode to form a hole injection layer with the thickness of 60nm; vacuum evaporating beta-NPB on the hole injection layer to form a hole transport layer with the thickness of 41nm; compounds 1-12 were vacuum evaporated on the hole transport layer and dopant Ir (mphq) 2 The acac was evaporated in a doping amount of 4wt% based on the total amount of the host and the dopant to form a light emitting layer with a thickness of 50nm; NBphen is evaporated on the luminescent layer in vacuum to be used as a hole blocking layer, and the thickness is 6nm; vacuum evaporation of Alq on hole blocking layer 3 As an electron transport layer, the thickness is 22nm; evaporating LiF on the electron transport layer in vacuum to form an electron injection layer, wherein the evaporation thickness is 1.1nm; al is vacuum-evaporated on the electron injection layer to form a cathode with a thickness of 160nm.
Comparative examples 2 to 12: preparation of organic electroluminescent devices 2 to 12
The compounds 1 to 12 in the light-emitting layer of comparative example 1 were replaced with compounds 1 to 25, compounds 1 to 81, compounds 1 to 204, compounds 1 to 585, compounds 1 to 701, compounds 2 to 5, compounds 2 to 18, compounds 2 to 19, compounds 2 to 82, compounds 2 to 226, and compounds 2 to 705, respectively, and the other steps were the same, to obtain organic electroluminescent devices 2 to 12.
The results of the test of the light emitting characteristics of the organic electroluminescent devices prepared in examples 1 to 35 of the present invention and comparative examples 1 to 12 are shown in table 1.
Table 1 test data of light emitting characteristics of organic electroluminescent device
As can be seen from Table 1, the organic electroluminescent devices 1 to 35 of the present invention have higher luminous efficiency and longer life span than the comparative devices 1 to 12, and the device performance is significantly improved.
Example 36: preparation of organic electroluminescent device 36
HI-1 is evaporated on the ITO anode in vacuum to be used as a first hole injection layer, and the thickness is 65nm; HAT-CN is evaporated on the first hole injection layer in vacuum to be used as a second hole injection layer, and the thickness is 4nm; evaporating HT-1 on the second hole injection layer in vacuum to be used as a hole transport layer, wherein the thickness is 40nm; first host compounds 1 to 12 and second host compounds 2 to 234 were vacuum-evaporated on the hole transport layer at a mass ratio of 1 2 (acac) vapor-depositing at a doping amount of 9wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 46nm; vacuum evaporation of ET-1 Liq =1 (wt%) as an electron transport layer on the light emitting layer, with a thickness of 28nm; vacuum evaporation plating Liq on the electron transport layer to be used as an electron injection layer, wherein the evaporation plating thickness is 1.3nm; al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 110nm.
Examples 37 to 70: preparation of organic electroluminescent devices 37 to 70
The first host compounds 1 to 12 in the light-emitting layer in example 36 were replaced with compounds 1 to 25, compounds 1 to 48, compounds 1 to 51, compounds 1 to 61, compounds 1 to 67, compounds 1 to 73, compounds 1 to 99, compounds 1 to 127, compounds 1 to 135, compounds 1 to 142, compounds 1 to 156, compounds 1 to 172, compounds 1 to 189, compounds 1 to 197, compounds 1 to 199, compounds 1 to 204, compounds 1 to 216, compounds 1 to 249, compounds 1 to 267, compounds 1 to 316, compounds 1 to 320, compounds 1 to 476, compounds 1 to 491, compounds 1 to 494, compounds 1 to 495, compounds 1 to 524, compounds 1 to 539, compounds 1 to 568, compounds 1 to 585, compounds 1 to 599, compounds 1 to 642, compounds 1 to 763, compounds 1 to 787, compounds 1 to 815;
the second host compounds 1 to 234 were replaced with compounds 2 to 99, compounds 2 to 478, compounds 2 to 687, compounds 2 to 72, compounds 2 to 26, compounds 2 to 226, compounds 2 to 19, compounds 2 to 87, compounds 2 to 11, compounds 2 to 605, compounds 2 to 63, compounds 2 to 31, compounds 2 to 138, compounds 2 to 14, compounds 2 to 47, compounds 2 to 23, compounds 2 to 107, compounds 2 to 250, compounds 2 to 75, compounds 2 to 544, compounds 2 to 64, compounds 2 to 344, compounds 2 to 79, compounds 2 to 211, compounds 2 to 329, compounds 2 to 5, compounds 2 to 616, compounds 2 to 432, compounds 2 to 158, compounds 2 to 30, compounds 2 to 126, compounds 2 to 755, compounds 2 to 41, and compounds 2 to 512, respectively, and the other steps were the same, to obtain organic electroluminescent devices 37 to 70.
Comparative example 13: preparation of comparative organic electroluminescent device 13
HI-1 is evaporated on the ITO anode in vacuum to be used as a first hole injection layer, and the thickness is 65nm; HAT-CN is evaporated on the first hole injection layer in vacuum to be used as a second hole injection layer, and the thickness is 4nm; evaporating HT-1 on the second hole injection layer in vacuum to be used as a hole transport layer, wherein the thickness is 40nm; compounds 1 to 48 were vacuum evaporated on the hole transport layer, and a dopant Ir (ppy) 2 (acac) vapor-depositing at a doping amount of 9wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 46nm; vacuum evaporation of ET-1 liq =1 (wt%) as an electron transport layer on the light emitting layer, with a thickness of 28nm; vacuum evaporation plating Liq on the electron transport layer to be used as an electron injection layer, wherein the evaporation plating thickness is 1.3nm; al is vacuum-evaporated on the electron injection layer to form a cathode with a thickness of 110nm.
Comparative examples 14 to 24: preparation of organic electroluminescent devices 14 to 24
Comparative organic electroluminescent devices 14 to 24 were obtained by replacing compounds 1 to 48 in the light-emitting layer of comparative example 1 with compounds 1 to 51, compounds 1 to 73, compounds 1 to 172, compounds 1 to 267, compounds 1 to 316, compounds 2 to 31, compounds 2 to 75, compounds 2 to 226, compounds 2 to 478, compounds 2 to 544, and compounds 2 to 687, respectively, in the same manner as the other steps.
The results of the test of the light emitting characteristics of the organic electroluminescent devices of examples 36 to 70 according to the present invention and comparative examples 13 to 24 are shown in table 2.
Table 2 light emitting characteristic test data of organic electroluminescent device
As can be seen from Table 1, the organic electroluminescent devices 36 to 70 of the present invention have higher luminous efficiency and longer service life and significantly improved device performance compared to the comparative devices 13 to 24.
The light emitting layer of the organic electroluminescent device of the present invention includes a first host material having a hole characteristic as shown in formula 1 and a second host material having an electron characteristic as shown in formula 2. The device comprising the main body material combination of the invention in the luminescent layer can effectively balance the injection and transmission of holes and electrons, can enable the holes and the electrons to be effectively compounded in the luminescent layer to form excitons, has higher utilization rate of the excitons, and forms a luminescent layer film more stable, thereby effectively improving the luminescent efficiency of the device and obviously prolonging the service life of the organic electroluminescent device.
It should be understood that the present invention has been particularly described with reference to particular embodiments thereof, but that various changes in form and details may be made therein by those skilled in the art without departing from the principles of the invention and, therefore, within the scope of the invention.
Claims (10)
1. An organic electroluminescent device comprises an anode, an organic layer and a cathode, wherein the organic layer is positioned between the anode and the cathode and comprises a light-emitting layer, and the organic electroluminescent device is characterized in that the light-emitting layer contains a first main material and a second main material, the first main material is a triarylamine compound shown in a formula 1, the second main material is a heterocyclic compound shown in a formula 2,
wherein, ar is 1 、Ar 2 Independently selected from one of the groups shown in the following,
a0 is an integer of 0 to 5; a1 is an integer of 0 to 4; the R is 1 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R 1 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 1 When each R is 1 Are the same or different from each other;
the La, lb, lc, L 1 、L 2 Independently selected from a single bond, substituted or unsubstituted arylene, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring; and said-La-Lb-Lc-is not a single bond;
a is selected from an integer of 0 to 4; the R is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring group, or two adjacent Rs are mutually bonded to form a substituted or unsubstituted ring; when a is 2 or more, each R is the same as or different from each other;
wherein Ar is selected from one of the groups shown in the specification,
said R is 0 The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C20 alicyclic ring and C2-C30 heteroaromatic ring fused ring group, or two adjacent R groups 0 Bonded to each other to form a substituted or unsubstituted ring;
x is selected from O, S, C (R) x ) 2 、N(R x )、Si(R x ) 2 In a group of (A), the R x The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C20 alicyclic ring and C2-C30 heteroaromatic ring fused ring group, or two adjacent R groups x Bonded to each other to form a substituted or unsubstituted ring;
b0 is selected from 0 to E4 is an integer of 4; b is an integer of 0 to 3; said R is 5 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 lipoheterocyclic group, or two adjacent R groups 5 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 5 When each R is 5 Are the same or different from each other;
said L is 0 One selected from a single bond or a group shown below; n is an integer of 0 to 3; when n is 2 or more, each L 0 Are the same or different from each other;
n1 is an integer of 0 to 4; the R is 6 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 lipoheterocyclic group, or two adjacent R groups 6 Bonded to each other to form a substituted or unsubstituted ring; when n1 is 2 or more, each R 6 Are the same or different from each other;
said L 3 、L 4 Independently selected from single bond, substituted or unsubstituted C3-C20 cycloalkylene, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring sub-condensed ring groupOne of condensed ring groups of the C3-C20 alicyclic ring and the C2-C30 heteroaromatic ring of (a);
the R is 3 、R 4 Independently selected from the group shown below,
the R is 7 One selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, and substituted or unsubstituted C3-C20 lipoheterocyclic group;
said X 1 Selected from O, S, N (R) x1 ) In a group of (A), the R x1 One selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, and substituted or unsubstituted C3-C20 lipoheterocyclic group;
the Y is the same or different and is selected from C (R) y ) Or N, said R y One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 aliphatic heterocyclic group, or two adjacent R groups y Bonded to each other to form a substituted or unsubstituted ring。
2. The organic electroluminescent device as claimed in claim 1, wherein Ar is Ar 1 、Ar 2 Independently selected from one of the groups shown below,
a0 is an integer of 0 to 5; a1 is an integer of 0 to 4; a2 is an integer of 0 to 7; a3 is an integer of 0 to 9;
the R is 1 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R 1 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 1 When each R is 1 Are the same or different from each other;
the R is 10 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R 10 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 10 When each R is 10 Are the same or different from each other;
the Ra are the same or different and are selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and fused ring group of C6-C30 aromatic ring, or two adjacent Ra are mutually bonded to form a substituted or unsubstituted ring; when there are two or more Ra, each Ra is the same as or different from each other.
3. The organic electroluminescent device as claimed in claim 1, wherein Ar is Ar 1 、Ar 2 Independently selected from one of the groups shown below,
a0 is an integer of 0 to 5; a1 is an integer of 0 to 4; a2 is an integer of 0 to 7; a3 is an integer of 0 to 9; a4 is an integer of 0 to 6; a5 is an integer of 0 to 8; a6 is an integer of 0 to 10; a7 is an integer of 0 to 3; a8 is an integer of 0 to 12;
the R is 1 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and a fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring, or two adjacent R 1 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 1 When each R is 1 Are the same or different from each other;
the R is 8 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and a fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring; when more than two R are present 8 When each R is 8 Are the same or different from each other;
the R is 10 Selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C15One of unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring condensed ring group, or two adjacent R 10 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 10 When each R is 10 The same or different from each other.
4. The organic electroluminescent device according to claim 1, wherein La, lb, lc, L 1 、L 2 Independently selected from a single bond or one of the groups shown as the following; and said-La-Lb-Lc-is not a single bond;
m1 is an integer of 0 to 4; m2 is an integer of 0 to 6; m3 is an integer of 0 to 5; m4 is an integer of 0 to 8; m5 is an integer of 0 to 3;
said R is 2 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R 2 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 2 When each R is 2 Are the same or different from each other;
said R is 20 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R 20 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 20 When each R is 20 Are the same or different from each other;
the R is m Identical or different from hydrogen, deuterium, tritium, cyanoOne of halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and a fused ring group of substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring, or two adjacent R m Bonded to each other to form a substituted or unsubstituted ring;
the R is m0 The same or different one selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring.
5. The organic electroluminescent device according to claim 1, wherein Ar is selected from one of the groups shown below,
b0 is an integer of 0 to 4; b is an integer of 0 to 3; b1 is an integer of 0 to 5; b2 is an integer of 0 to 6; b3 is an integer of 0 to 8; b4 is an integer of 0 to 10; b5 is an integer of 0 to 12;
said R is 5 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C6-C25 aromatic ring, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C2-C25 heteroaromatic ring, substituted or unsubstituted C3-C15 lipoheterocyclic group, or two adjacent R 5 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 5 When each R is 5 Are the same or different from each other;
said R is 9 Selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2EOne of a heteroaryl group of C25, a condensed ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C6-C25 aromatic ring, a condensed ring group of a substituted or unsubstituted C3-C15 alicyclic ring and a C2-C25 heteroaromatic ring, and a substituted or unsubstituted C3-C15 lipo-heterocyclic group; when more than two R are present 9 When each R is 9 Are the same or different from each other;
the R is x The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring fused ring group, substituted or unsubstituted C3-C15 alicyclic ring and C2-C25 heteroaromatic ring fused ring group, or substituted or unsubstituted C3-C15 lipoheterocyclic group, or two adjacent R x Bonded to each other to form a substituted or unsubstituted ring.
6. An organic electroluminescent device according to claim 1, wherein L is L 0 One selected from a single bond or a group shown below; n is an integer of 0 to 3; when n is 2 or more, each L 0 Are the same or different from each other;
n1 is an integer of 0 to 4; n2 is an integer of 0 to 6;
the R is 6 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 lipoheterocyclic group, or two adjacent R groups 6 Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present 6 When each R is 6 The same or different from each other.
7. An organic electroluminescent device according to claim 1, wherein L is 3 、L 4 Independently selected from a single bond or one of the groups shown as follows,
the Z is the same or different and is selected from C (R) z ) Or N, said R z The same or different one selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C20 alicyclic ring and C2-C30 heteroaromatic ring fused ring group, or two adjacent R groups z Bonded to each other to form a substituted or unsubstituted ring.
8. An organic electroluminescent device according to claim 1, wherein R is 3 、R 4 Independently selected from one of the groups shown in the following,
the R is 7 Selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring fused ring group, orOne of a condensed ring group of substituted or unsubstituted C3-C15 alicyclic ring and C2-C25 heteroaromatic ring, and a substituted or unsubstituted C3-C15 alicyclic heterocyclic group;
the R is x1 One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C6-C25 aromatic ring, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C2-C25 heteroaromatic ring, and substituted or unsubstituted C3-C15 lipoheterocyclic group;
c1 is an integer of 0 to 4; c2 is an integer of 0 to 3; c3 is an integer of 0 to 2; the R is y One selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 lipoheterocyclic group, or two adjacent R groups y Bonded to each other to form a substituted or unsubstituted ring; when more than two R are present y When each R is y The same or different from each other.
9. The organic electroluminescent device as claimed in claim 1, wherein the triarylamine compound represented by formula 1 is at least one selected from the group consisting of the following structures,
10. the organic electroluminescent device according to claim 1, wherein the heterocyclic compound represented by formula 2 is at least one selected from the group consisting of the structures,
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