CN117088859A - Triarylamine derivative and organic electroluminescent device thereof - Google Patents

Triarylamine derivative and organic electroluminescent device thereof Download PDF

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CN117088859A
CN117088859A CN202311054758.9A CN202311054758A CN117088859A CN 117088859 A CN117088859 A CN 117088859A CN 202311054758 A CN202311054758 A CN 202311054758A CN 117088859 A CN117088859 A CN 117088859A
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刘喜庆
孙月
陆影
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Changchun Hyperions Technology Co Ltd
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Abstract

The invention provides a triarylamine derivative and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescent. In order to solve the problem of low device performance caused by a coating material in the prior art, the invention provides a triarylamine derivative and an organic electroluminescent device thereof, and the triarylamine derivative is applied to the organic electroluminescent device as the coating material to effectively improve the luminous efficiency and the service life of the device.

Description

Triarylamine derivative and organic electroluminescent device thereof
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a triarylamine derivative and an organic electroluminescent device thereof.
Background
In the new era, the Internet brings great reform to human beings, so that the development of technology is more rapid. In order to make information communication abundant and convenient, a display with more excellent performance is required to meet the needs of human life, and an Organic Light Emitting Diode (OLED) as a new generation display also rapidly becomes a research hot spot of people, has great potential to replace an LCD technology, and becomes a star technology in the display field. Compared with the traditional liquid crystal display, the OLED display technology has the advantages of self-luminescence, wide viewing angle, high resolution, lower power consumption, extremely high reaction speed and the like, has wide application prospect in new generation display and illumination products, and is a popular research field in the last ten years.
In the OLED, under the action of an externally applied electric field, electrons from a cathode and holes from an anode enter an organic layer to carry out energy recombination and transfer the energy to an organic light-emitting compound, so that the organic light-emitting compound transits from a ground state to an excited state, and excited molecules return to the ground state from the excited state to release the energy in a light form, thereby forming a light-emitting phenomenon. An OLED is a sandwich-like sandwich structure, typically consisting of an anode, a cathode and an organic layer formed between the two electrodes. Currently, organic layers involved in OLEDs include hole injection layers, hole transport layers, hole blocking layers, light emitting layers, electron blocking layers, electron transport layers, electron injection layers, capping layers, and the like. Although OLED fabrication processes are continuously innovated and reformed, there are problems in commercialization of the OLED fabrication process for large-scale application due to the fact that the development of the organic light emitting materials is not perfect at the present stage.
With the demands of large market environments, the performance demands of the OLED devices are continuously improved, and the coating materials used at present have a plurality of defects when being applied to the organic electroluminescent devices. The conventional coating materials are mostly inorganic materials, and have certain disadvantages, on one hand, the inorganic materials are required to be evaporated at a higher temperature, the device is deformed due to the high temperature, on the other hand, the light inside the device has a plasma resonance effect and a total reflection phenomenon, the coupling efficiency of the light outside the device is reduced, and the generation of joule heat in operation is increased, so that in order to improve the luminous efficiency of the organic luminous device and the service life of the device, the development of the coating materials with lower absorption in the visible light region, high refractive index, excellent film stability and good thermal stability is required to be developed.
Disclosure of Invention
In order to solve the problems, the invention provides a triarylamine derivative and an organic electroluminescent device thereof, which have obviously improved luminous efficiency and service life.
The invention provides a triarylamine derivative, which has a structure shown as a formula I,
in formula I, x, equal to or different from each other, are chosen from CH or N atoms, and at least two x are chosen from N atoms, said x being chosen from C atoms when x is bonded to other groups;
y is selected from O or S;
the Ar is as follows 1 Any one selected from the groups shown in the formulas II-1 to II-11;
the z are identical or different from each other and are selected from CH or N atoms, when z is bonded with other groups, the z is selected from C atoms, and at least one z in each group of the formulae II-1 to II-9 is selected from N atoms;
t is selected from any one of O, S, N (R); the R is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or R can be directly linked to L 1 Bonding;
said Q is selected from O, S, C (R x R y ) Or N (R) z )；
The R is x 、R y Are the same or different from each other, and are selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring groups; or R is x 、R y Any one of them can be directly connected with L 1 Bonding, or R x 、R y Can be interconnected to form a ring as shown below;
the R is 4 Selected from hydrogen, deuterium or any one of the following groups substituted or unsubstituted by one or more deuterium, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl or terphenyl;
the p is 1 Selected from 0, 1, 2, 3 or 4, p 2 Selected from 0, 1, 2, 3, 4, 5 or 6, p 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8,p 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, p 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, p 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, p 7 Selected from 0, 1 or 2.
The R is z Selected from the group consisting of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C2-C12 alkenyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C6-C30 aromatic rings, and C3-C30, and any one of condensed ring groups of an aliphatic ring; or R is z Can be directly connected with L 1 Bonding;
the ring A and the ring B are the same or different and are selected from any one of an unsubstituted, substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted N-heterocyclic benzene ring and a substituted or unsubstituted N-heterocyclic naphthalene ring;
the R is 1 Is the same or different from each other, and is selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C7 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring;
The a 1 Selected from 0, 1, 2, 3, 4 or 5, said a 2 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said a 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, said a 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said a 5 Selected from 0, 1, 2, 3 or 4, said a 6 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said a 7 Selected from 0, 1, 2 or 3, when two or more R's are present 1 When two or more R' s 1 Identical or different from each other, or adjacent two R 1 May be linked to each other to form a substituted or unsubstituted ring;
the R is a 、R b 、R c Is the same or different from each other, and is selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring;
the m is 1 Selected from 0, 1, 2, 3, 4, 5 or 6, when two or more R's are present a When two or more R' s a Identical or different from each other, or adjacent two R' s a May be linked to each other to form a substituted or unsubstituted ring;
The m is 2 Selected from 0, 1, 2, 3 or 4, when two or more R's are present b When two or more R' s b Identical or different from each other, or adjacent two R' s b May be linked to each other to form a substituted or unsubstituted ring;
the m is 3 Selected from 0, 1, 2, 3, 4 or 5, when two or more R's are present c When two or more R' s c The same or different from each other;
the L is 0 、L 1 Are the same or different from each other, and are selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, bivalent substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring group and combination thereof.
The invention also 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 or outside any one electrode of the anode and the cathode, and the organic layer comprises at least one or more than one of the triarylamine derivatives.
The beneficial effects are that: the triarylamine derivative provided by the invention has the advantages of strong rigidity, proper glass transition temperature (Tg), good heat stability and high refractive index in the molecule, promotes uniform arrangement among molecules, reduces the recrystallization phenomenon among the molecules, is favorable for forming a uniform and stable film in the evaporation process of a device, and is used as a coating material to be applied to an organic electroluminescent device, so that the coupling efficiency of light in the device is increased, the light extraction efficiency is improved, the generation of Joule heat in the operation process of the device is reduced, and the luminous efficiency and the service life of the device are improved.
Detailed Description
The following description of the embodiments of the present invention will be made more complete and obvious by the following description of the embodiments of the present invention, wherein the embodiments are described in some, but not all, of the embodiments of the present invention. All other embodiments, which can be made by a person skilled in the art without making any inventive effort, are intended to fall within the scope of the present invention.
In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both its natural isotopic abundance and non-natural abundance.
In the present specification, "×" means a moiety attached to another substituent.
In this specification, when a substituent is not fixed in position on a ring, it means that it can be attached to any of the corresponding selectable positions of the ring. For example, the number of the cells to be processed,can indicate->Can representCan represent Etc. And so on.
In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to either of the two or two rings, in particular to either of the respective selectable sites of the rings. For example, the number of the cells to be processed, Can indicate-> Can indicate->And so on.
In the present specification, when the ring position of the benzene ring on the ring is not fixed, it means that it may be attached to any two positions in the corresponding optional positions of the ring, for exampleCan representAnd so on.
Examples of the halogen atom according to the present invention may include fluorine, chlorine, bromine or iodine.
Alkyl according to the invention is understood to mean a monovalent radical obtained by removing one hydrogen atom from an alkane molecule, which may be a straight-chain alkyl radical or a branched alkyl radical, preferably having from 1 to 12 carbon atoms, more preferably having from 1 to 8 carbon atoms, particularly preferably having from 1 to 6 carbon atoms. Alkyl groups may be substituted or unsubstituted. Specific examples may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like, but are not limited thereto.
Alkenyl in the context of the present invention means a monovalent radical obtained by removing one hydrogen atom from an olefin molecule, which may be a straight-chain alkenyl or branched alkenyl radical, preferably having 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms. Alkenyl groups may be substituted or unsubstituted. Specific examples may include vinyl, 1-propenyl, isopropenyl, butenyl, pentenyl, 3-methyl-1-butenyl, allyl, 1-phenylvinyl-1-yl, styryl, and the like, but are not limited thereto.
Cycloalkyl according to the present invention means a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 12 carbon atoms, more preferably 3 to 6 carbon atoms. Cycloalkyl groups may be substituted or unsubstituted. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, and the like.
Aryl according to the invention is understood to mean a monovalent radical obtained by removing one hydrogen atom from the aromatic nucleus of an aromatic compound molecule, which may be a monocyclic aryl, polycyclic aryl or fused ring aryl, preferably having from 6 to 30 carbon atoms, more preferably from 6 to 18 carbon atoms, particularly preferably from 6 to 12 carbon atoms. Aryl groups may be substituted or unsubstituted. The monocyclic aryl refers to aryl having only one aromatic ring in the molecule, for example, phenyl, etc., but is not limited thereto; the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, for example, biphenyl, terphenyl, tetrabiphenyl, etc., but is not limited thereto; the condensed ring aryl group means an aryl group having two or more aromatic rings in the molecule and condensed with each other by sharing two adjacent carbon atoms, for example, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, Phenyl, triphenylenyl, fluoranthenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzofluorenyl, 9' -spirobifluorenyl, and the like, but are not limited thereto.
Heteroaryl according to the present invention refers to the generic term for groups in which one or more of the aromatic nucleus carbon atoms in the aryl group is replaced by a heteroatom, including but not limited to O, S, N, si or P atoms, preferably having 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, most preferably 2 to 12 carbon atoms. The attachment site of the heteroaryl group may be on a ring-forming carbon atom or on a ring-forming heteroatom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused ring heteroaryl group. Heteroaryl groups may be substituted or unsubstituted. The monocyclic heteroaryl group includes, but is not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, and the like; the polycyclic heteroaryl group includes bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but is not limited thereto; the fused ring heteroaryl group includes, but is not limited to, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, phenanthroline, naphthyridinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxazinyl, spirofluorene oxanthrenyl, spirofluorene thianthrenyl, and the like.
The aliphatic ring according to the present invention is a cyclic hydrocarbon having aliphatic properties, and the molecule contains a closed carbon ring, preferably 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, still more preferably 3 to 12 carbon atoms, and still more preferably 3 to 7 carbon atoms. Which may form mono-or polycyclic hydrocarbons and may be fully unsaturated or partially unsaturated. The aliphatic ring may be substituted or unsubstituted. Specific examples may include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, and the like. The plurality of monocyclic hydrocarbons may also be linked in a variety of ways: two rings in the molecule can share one carbon atom to form a spiro ring; the two carbon atoms on the ring can be connected by a carbon bridge to form a bridge ring; several rings may also be interconnected to form a cage-like structure.
The fused ring of an aromatic ring and an aliphatic ring in the present invention means a ring having one or more aromatic rings and having one or more aliphatic rings fused to each other by sharing two adjacent carbon atoms, the aromatic ring preferably has 6 to 30 carbon atoms, more preferably has 6 to 18 carbon atoms, most preferably has 6 to 12 carbon atoms, and the aliphatic ring preferably has 3 to 30 carbon atoms, more preferably has 3 to 18 carbon atoms, more preferably has 3 to 12 carbon atoms, and most preferably has 3 to 7 carbon atoms. The fused ring of the aromatic ring and the aliphatic ring may be substituted or unsubstituted. Examples include, but are not limited to, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutene, benzocyclopentene, benzocyclohexene, benzocycloheptene, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexene, naphthocyclopentene, naphthocyclohexene, and the like.
The arylene group according to the present invention is a generic term for divalent groups remaining after two hydrogen atoms are removed from the aromatic nucleus carbon of an aromatic hydrocarbon molecule, and may be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group, preferably having 6 to 30 carbon atoms, more preferably having 6 to 22 carbon atoms, still more preferably having 6 to 18 carbon atoms, and most preferably having 6 to 12 carbon atoms. Arylene groups may be substituted or unsubstituted. The polycyclic arylene group may be, but is not limited to, biphenylene, terphenylene, tetra-biphenylene, and the like. As the condensed ring arylene group, naphthylene, anthrylene, phenanthrylene, pyreylene, fluorenylene, spirofluorenylene, triphenylene, perylene, fluoranthrylene, and phenylene groups may be mentionedA base, etc., but is not limited thereto.
The heteroarylene group according to the present invention means a group in which two hydrogen atoms are removed from the nuclear carbon of an aromatic heterocycle composed of carbon and a heteroatom, which may be one or more of N, O, S, si, P, a monocyclic heteroarylene group, a polycyclic heteroarylene group or a condensed ring heteroarylene group, preferably having 2 to 30 carbon atoms, more preferably having 2 to 22 carbon atoms, still more preferably having 2 to 20 carbon atoms, most preferably 3 to 12 carbon atoms, and the heteroarylene group may be substituted or unsubstituted. Examples may include, but are not limited to, a pyridylene, a pyrimidylene, a pyrazinylene, a pyridazinylene, a triazinylene, a thienyl, a pyrrolylene, a furanylene, a pyranylene, an oxazolylene, a thiazolylene, an imidazolylene, a benzoxazolylene, a benzothiazolylene, a benzimidazolylene, a carbazolylene, a benzocarbazolylene, an acridinylene, an oxaanthracylene, a thioxanthoylene, a phenazinylene, a phenothiazinylene, a phenoxazinylene, an indolylene, a quinolinylene, an isoquinolylene, a benzothienyl, a benzofuranylene, a dibenzofuranylene, a dibenzothiophenylene, a quinoxalinylene, a quinazolinylene, a naphthyridineylene, a purinylene, a phenanthroline, and the like.
The fused ring group of the divalent aromatic ring and the aliphatic ring in the present invention means that there are two linked positions, i.e., a divalent group, on the fused ring group of the aromatic ring and the aliphatic ring. In addition to the divalent groups, the above description of the condensed ring groups of the aromatic ring and the aliphatic ring may be applied.
"unsubstituted" in "substituted or unsubstituted" as used herein means that the hydrogen atom on the group is not substituted with any substituent; "substituted" means that at least one hydrogen atom on the group is replaced with a substituent, and the position of substitution is not limited. When a plurality of hydrogens are substituted with a plurality of substituents, the plurality of substituents may be the same or different.
The substituents in the "substituted or unsubstituted" described in the present invention may be the same or different from each other and are selected from any one of deuterium, cyano, nitro, trifluoromethyl, halogen atom, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C2-C12 alkenyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C2-C12 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C6-C30 aromatic ring and condensed ring group of C3-C30 aliphatic ring, preferred are deuterium, cyano, halogen atom, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, tolyl, pentadeuterated phenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, triphenylenyl, A group, perylene group, fluoranthryl group, fluorenyl group, 9-dimethylfluorenyl group, 9-diphenylfluorenyl group, 9-methyl-9-phenylfluorenyl group, spirofluorenyl group, carbazolyl group, 9-phenylcarbazolyl group, 9' -spirobifluorenyl group, benzocyclopropyl group, benzocyclobutanyl group, benzocyclobutenyl group, spirofluorenyl group, and combinations thereof benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopentenyl, naphthocyclohexenyl, naphthocycloheptanyl, naphthocyclopentenyl, benzocyclohexenyl, naphtyl and naphtyl naphthalocyclohexenyl, naphthaloheptenyl, pyrrolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenoxazinyl, acridinyl and the like, but is not limited thereto.
The term "link-forming ring" as used herein means that two groups are linked to each other by a chemical bond and optionally aromatized. As exemplified below:
In the present invention, the ring formed by the connection may be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of both, and the ring formed by the connection may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentaacene, cyclohexene, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.
The invention provides a triarylamine derivative, which has a structure shown in a formula I,
in formula I, x, equal to or different from each other, are chosen from CH or N atoms, and at least two x are chosen from N atoms, said x being chosen from C atoms when x is bonded to other groups;
y is selected from O or S;
the Ar is as follows 1 Any one selected from the groups shown in the formulas II-1 to II-11;
the z are identical or different from each other and are selected from CH or N atoms, when z is bonded with other groups, the z is selected from C atoms, and at least one z in each group of the formulae II-1 to II-9 is selected from N atoms;
t is selected from any one of O, S, N (R); the R is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or R can be directly linked to L 1 Bonding;
said Q is selected from O, S, C (R x R y ) Or N (R) z )；
The R is x 、R y Are the same or different from each other, and are selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring groups; or R is x 、R y Any one of them can be directly connected with L 1 Bonding, or R x 、R y Can be interconnected to form a ring as shown below;
the R is 4 Selected from hydrogen, deuterium or any one of the following groups substituted or unsubstituted by one or more deuterium, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl or terphenyl;
the p is 1 Selected from 0, 1, 2, 3 or 4, p 2 Selected from 0, 1, 2, 3, 4, 5 or 6, p 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8,p 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, p 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, p 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, p 7 Selected from 0, 1 or 2.
The R is z Any one selected from a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C2-C12 alkenyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring condensed ring group; or R is z Can be directly connected with L 1 Bonding;
the ring A and the ring B are the same or different and are selected from any one of an unsubstituted, substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted N-heterocyclic benzene ring and a substituted or unsubstituted N-heterocyclic naphthalene ring;
the R is 1 Is the same or different from each other, and is selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C7 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring;
The a 1 Selected from the group consisting of0. 1, 2, 3, 4 or 5, said a 2 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said a 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, said a 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said a 5 Selected from 0, 1, 2, 3 or 4, said a 6 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said a 7 Selected from 0, 1, 2 or 3, when two or more R's are present 1 When two or more R' s 1 Identical or different from each other, or adjacent two R 1 May be linked to each other to form a substituted or unsubstituted ring;
the R is a 、R b 、R c Is the same or different from each other, and is selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring;
the m is 1 Selected from 0, 1, 2, 3, 4, 5 or 6, when two or more R's are present a When two or more R' s a Identical or different from each other, or adjacent two R' s a May be linked to each other to form a substituted or unsubstituted ring;
The m is 2 Selected from 0, 1, 2, 3 or 4, when two or more R's are present b When two or more R' s b Identical or different from each other, or adjacent two R' s b May be linked to each other to form a substituted or unsubstituted ring;
the m is 3 Selected from 0, 1, 2, 3, 4 or 5, when two or more R's are present c When two or more R' s c The same or different from each other;
the L is 0 、L 1 Identical or different from each other, selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, divalent substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring groupAny one of the following, and combinations thereof.
Preferably, the formula IWherein x are the same or different from each other and are selected from CH or N atoms, and at least two x are selected from N atoms, including two, three, four, five, six or seven of x are selected from N atoms.
Preferably, in the formula ISelected from any one of the structures shown below,
the R is c Selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen or any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, C1 to C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl or benzocycloheptanyl;
Said b 1 Selected from 0, 1, 2, 3, 4 or 5, said b 2 Selected from 0, 1, 2, 3 or 4, said b 3 Selected from 0, 1, 2 or 3, said b 4 Selected from 0, 1 or 2, said b 5 Selected from 0 or 1, when two or more R's are present c When two or more R' s c The same as or different from each other.
Preferably, in the formula ISelected from any one of the structures shown below,
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the c 1 Selected from 1, 2, 3, 4 or 5, said c 2 Selected from 1, 2, 3 or 4, said c 3 Selected from 1, 2 or 3.
Preferably, in the formula ISelected from any one of the structures shown below, < + >>
The R is a 、R b The same as or different from each other, selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen atoms, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornane, adamantane, phenyl, biphenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9' -spirobifluorenyl, furanyl, dibenzofuranyl, thienyl, dibenzothiophenyl, pyridyl, and pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, methyl-substituted adamantyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyridinyl, deuterated anthracenyl, deuterated phenanthrenyl, deuterated triphenylenyl, deuterated fluorenyl, deuterated furanyl, deuterated Any one of dibenzofuranyl, deuterated thienyl, deuterated dibenzothienyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, trifluoromethyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, deuterated methyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl;
said n 1 Selected from 0, 1, 2, 3, 4, 5 or 6, said n 2 Selected from 0, 1, 2 or 3, said n 3 Selected from 0, 1, 2, 3, 4 or 5, said n 4 Selected from 0, 1, 2, 3 or 4, said n 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, when two or more R's are present a 、R b When two or more R' s a 、R b The same as or different from each other.
Preferably, the Ar 1 Selected from any one of the structures shown below;
the z are identical or different from each other and are selected from CH or N atoms, and at least one z in each group is selected from N atoms; when z is bonded to other groups, the z is selected from a C atom;
the R is 1 Are identical or different from each other and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen or substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornylA substituted alkyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, pyridyl group, pyrimidinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, dibenzofuranyl group, dibenzothienyl group, benzocyclopropanyl group, benzocyclobutanyl group, benzocyclopentanyl group, benzocyclohexenyl group, or benzocycloheptanyl group;
said d 1 Selected from 0, 1, 2, 3 or 4, said d 2 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said d 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, said d 4 Selected from 0, 1, 2, 3, 4, 5 or 6, said d 5 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, said d 6 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said d 7 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said d 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said d 9 Selected from 0, 1, 2 or 3, when two or more R's are present 1 When two or more R' s 1 The same as or different from each other.
Preferably, the Ar 1 Selected from any one of the structures shown below;
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said Q is selected from O, S, C (R x R y) Or N (R) z )；
The R is x 、R y Are identical or different from each other and are selected from any one of hydrogen, deuterium or a group substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl,Tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl or benzocycloheptanyl; or R is x 、R y Any one of them can be directly connected with L 1 Bonding, or R x 、R y Can be interconnected to form a ring as shown below;
the R is 4 Selected from hydrogen, deuterium or any one of the following groups substituted or unsubstituted by one or more deuterium, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl or terphenyl;
the p is 1 Selected from 0, 1, 2, 3 or 4, p 2 Selected from 0, 1, 2, 3, 4, 5 or 6, p 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8,p 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, p 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, p 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, p 7 Selected from 0, 1 or 2.
The R is z Any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, alkyl of C1 to C12: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexyl Alkyl or benzocycloheptyl; or R is z Can be directly connected with L 1 Bonding;
t is selected from any one of O, S, N (R);
the R is selected from any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl and C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, dibenzofuranyl, dibenzothienyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, or benzocycloheptanyl; or R can be directly linked to L 1 And (5) bonding.
Preferably, the L 0 、L 1 Are identical or different from each other, are selected from single bonds or any one of the structures shown below,
the R is 2 Are identical or different from each other and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen or substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl or benzocycloheptanyl;
Said e 1 Selected from 0, 1, 2, 3 or 4, said e 2 Selected from 0, 1, 2 or 3, said e 3 Selected from 0, 1 or 2, said e 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said e 5 Selected from 0, 1,2. 3, 4, 5, 6, 7, 8, 9 or 10, said e 6 Selected from 0, 1, 2, 3, 4, 5 or 6, said e 7 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, when two or more R's are present 2 When two or more R' s 2 The same as or different from each other.
Preferably, the L 0 、L 1 Are identical or different from each other, are selected from single bonds or any one of the structures shown below,
and q is selected from 1, 2, 3 or 4.
Preferably, the triarylamine derivative is selected from any one of the following structures,
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the specific structural forms of the triarylamine derivative represented by formula I according to the present invention are listed above, but the present invention is not limited to the listed chemical structures, and substituents are included as defined above, even when the structural form represented by formula I is used as a basis.
The invention also 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 or outside any one electrode of the anode and the cathode, and the organic layer comprises at least one or more than one of the triarylamine derivatives.
Preferably, the organic layer is located outside any one of the anode and the cathode, and the organic layer includes a cover layer including at least one or more of the triarylamine derivatives of the present invention.
Preferably, the organic layer of the present invention is located between the anode and the cathode, and includes at least one layer of a hole transport region, a light emitting layer, and an electron transport region.
Preferably, the hole transport region according to the present invention includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.
Preferably, the hole transport region according to the present invention includes at least one of a hole injection layer and a hole transport layer, and preferably, the hole transport region according to the present invention includes a hole transport layer.
Preferably, the hole transport layer according to the present invention comprises a first hole transport layer and a second hole transport layer.
Preferably, the light emitting layer according to the present invention comprises a host material and a doping material.
Preferably, the electron transport region of the present invention comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.
In the organic electroluminescent device according to the present invention, each functional layer may be formed of a single layer or two or more thin films, and each thin film may be formed of one material or two or more materials, however, the structure of the organic electroluminescent device is not limited thereto.
The material of each layer of thin film in the organic electroluminescent device is not particularly limited, and materials known in the art can be used. The following describes each organic functional layer of the above-mentioned organic electroluminescent device and the electrodes on both sides of the device, respectively:
the anode material according to the invention is preferablyA material having a high function is used to improve hole injection efficiency. Anode materials useful in the present invention are selected from the following: indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and tin oxide (SnO) 2 ) Zinc oxide (ZnO) or any combination thereof, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode may have a single-layer structure or a multi-layer structure including two or more layers, for example, the anode may have a single-layer structure of Al or a three-layer structure of ITO/Ag/ITO, but is not limited thereto.
The hole injection layer according to the present invention preferably uses a material having a good hole accepting ability. Specific examples of the hole injection layer material that can be used in the present invention may include metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide, etc., phthalocyanine compounds, biphenylamine compounds, phenazine compounds, etc., such as copper phthalocyanine (CuPc), titanylphthalocyanine, N ' -diphenyl-N, N ' -bis- [4- (N, N-diphenylamine) phenyl ] benzidine (npb), N ' -tetrakis (4-methoxyphenyl) benzidine (MeO-TPD), and bisquinoxalino [2,3-a:2',3' -c ] phenazine (HATNA), 4',4 "-tris [ 2-naphthylphenylamino ] triphenylamine (2T-NATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazabenzophenanthrene (HAT-CN), 4',4" -tris (N, N-diphenylamino) triphenylamine (TDATA), and the like, but are not limited thereto.
The hole transport layer material according to the present invention is preferably a material having high hole mobility. Can be selected from any one or more of the following structures: carbazole derivatives, triarylamine derivatives, biphenyldiamine derivatives, fluorene derivatives, stilbene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, and the like. Examples of the hole transport layer material include, but are not limited to, N '-diphenyl-N, N' -bis (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine (TPD), N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB), 4- [1- [4- [ bis (4-methylphenyl) amino ] phenyl ] cyclohexyl ] -N- (3-methylphenyl) -N- (4-methylphenyl) aniline (TAPC), N '-tetrakis (3-methylphenyl) -3,3' -dimethylbiphenyl diamine (HMTPD), and the like.
The luminescent layer material comprises a host material AND a doping material, the luminescent layer host material needs to have bipolar charge transmission property AND has proper energy level, AND is selected from 4,4 '-bis (9-Carbazolyl) Biphenyl (CBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), 9' - (1, 3-phenyl) bis-9H-carbazole (mCP), 4 '-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (alpha-AND), N' -bis- (1-naphthyl) -N, N '-diphenyl- [1,1':4',1": 4',1 '-tetrabenzoyl ] -4,4' -diamine group (4 PNPB), 1,3, 5-tris (9-carbazolyl) benzene (TCP), AND the like. In addition to the above materials and combinations thereof, the light emitting layer host material may include other known materials suitable for a light emitting layer, and the like, but is not limited thereto. The light-emitting layer doping material of the present invention is classified into a blue light-emitting material, a green light-emitting material, and a red light-emitting material. The light-emitting layer doped material can be a simple fluorescent material or phosphorescent material, or is formed by collocating and combining fluorescent and phosphorescent materials, and is selected from (6- (4- (diphenylamino (phenyl) -N, N-diphenylpyrene-1-amine) (DPAP-DPPA), 2,5,8, 11-tetra-tert-butylperylene (TBPe), 4 '-di [4- (diphenylamino) styryl ] biphenyl (BDAVBi), 4' -di [4- (di-p-tolylamino) styryl ] biphenyl (DPAVBi), di (2-hydroxyphenylpyridine) beryllium (Bepp 2), di (4, 6-difluorophenylpyridine-C2, N) picolinic iridium (FIrpic), tris (2-phenylpyridine) iridium (Ir (ppy) 3), bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy) 2 (acac)), 9, 10-bis [ N- (p-tolyl) anilino ] anthracene (BDAVBi), 4- (dicyanomethyl) -2-methyl-6- (4-p-tolyl) styryl ] biphenyl (DPAVBi), bis (2- (4-hydroxyphenylpyridine) iridium (Ir) 2, 6-phenylpyridine) iridium (Ir (p-phenylpyridine) iridium (Ir) 2) (Ir) 2 (p-phenylpyridine) iridium (Ir) and the like, iridium (Ir (p-phenyl) 2) iridium (Ir) 2 (Ir), but is not limited thereto.
The doping ratio of the host material and the guest material in the light-emitting layer according to the present invention is determined according to the materials used. The amount of the dopant is preferably 0.1 to 70% by mass, more preferably 0.1 to 30% by mass, still more preferably 1 to 20% by mass, and particularly preferably 1 to 10% by mass.
The hole blocking layer according to the present invention preferably uses a material having a strong hole blocking ability and a suitable HOMO/LUMO energy level. The hole blocking layer material can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, phenanthroline derivatives, azabenzene derivatives, anthrone derivatives, and the like, but are not limited thereto.
The electron transport layer material of the present invention is preferably a material having high electron mobility. Can be selected from any one or more of the following structures: 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), tris (8-hydroxyquinoline) aluminum (III) (Alq 3), 8-hydroxyquinoline-lithium (Liq), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), 3- (biphenyl-4-yl) -5- (4-t-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), and the like, but are not limited thereto.
The electron injection layer material of the present invention is preferably a material having a small potential barrier difference from a material of an adjacent organic layer, and specific examples may include: alkali metal compounds (for example, lithium oxide, lithium fluoride, cesium carbonate, cesium fluoride, 8-hydroxyquinoline cesium, 8-hydroxyquinoline aluminum), organic metal salts (metal acetate, metal benzoate, or metal stearate), molybdenum trioxide, metal aluminum, and the like, but are not limited thereto.
The cathode material according to the present invention preferably uses a material having a low work function that can promote electron injection into the organic layer to lower the electron injection barrier. Can be selected from any one or more of the following materials: ag. Mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Ca, liF/Al, mo, ti, compounds including them or mixtures thereof (e.g., mixtures of Ag and Mg), but are not limited thereto.
The coating layer according to the present invention is provided outside either one of the anode and the cathode, and preferably a material capable of improving the optical coupling efficiency inside the device is used. Can be selected from any one or more of the following structures: aryl amine derivatives, biscarbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, benzofuran derivatives, diamine derivatives, porphyrin derivatives, phthalocyanine derivatives, and the like, but are not limited thereto. Preferred are compounds of formula I according to the invention.
The thickness of each organic layer of the organic electroluminescent device is not particularly limited, and may be any thickness commonly used in the art.
The organic electroluminescent device of the present invention may be any one of vacuum evaporation method, spin coating method, vapor deposition method, blade coating method, laser thermal transfer method, electro-spray coating method, slit coating method, and dip coating method.
The organic electroluminescent device can be widely applied to the fields of panel display, illumination light sources, flexible OLED, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, indication boards, signal lamps and the like.
The present invention is explained more fully by the following examples, but is not intended to be limited thereby. Based on this description, one of ordinary skill in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the full scope of the disclosure without undue burden.
Preparation and characterization of the Compounds
The method for preparing the structure represented by formula I of the present invention is not particularly limited, and conventional methods known to those skilled in the art can be employed. For example, the structure of formula 1 of the present invention can be prepared by the synthetic route shown below, such as carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc.
Preparation of intermediate a:
preparation of intermediate C:
preparation of the compound of formula I:
wherein X is a 、X b Are the same or different from each other and are selected from any one of Cl, br and I; ar (Ar) 1 、L 0 、L 1 、R a ～R c 、m 1 ～m 3 The limitations of Y, x are the same as described above.
Description of the starting materials, reagents and characterization equipment:
the raw materials and reagent sources used in the following examples are not particularly limited, and may be commercially available products or prepared by methods well known to those skilled in the art. The raw materials and the reagents used in the invention are all reagent pure.
The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;
the elemental analysis uses a Vario EL cube type organic elemental analyzer of Elementar, germany, and the mass of the sample is 5-10 mg;
synthesis example 1: preparation of intermediate A-19:
a-19 (17.60 g,100.00 mmol), b-19 (25.51 g,100.00 mmol) and K were added sequentially to the flask under nitrogen 2 CO 3 (22.11 g,160 mmol), 420mL of mixed solvent (toluene: ethanol: water=2:1:1), then nitrogen was introduced to replace air three times, and Pd (PPh) was added 3 ) 4 (1.16 g,1.00 mmol) was stirred at reflux temperature for 4h, after the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added, extracted with dichloromethane, left to stand for separation, the organic layer was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated by distillation under reduced pressure, and the obtained solid was recrystallized from toluene and dried to give intermediate A-19 (16.15 g, yield 72) 11%); HPLC purity. Mass spectrum m/z:224.1239 (theory: 224.1252).
The preparation method of intermediate A-19 in synthetic example 1 is followed by corresponding replacement of the raw materials, namely intermediate A, as shown in the following table:
synthesis example 2: preparation of intermediate C-57:
under the protection of nitrogen, c-57 (19.15 g,100.00 mmol), b-57 (25.61 g,100.00 mmol) and K are added into a reaction bottle in sequence 2 CO 3 (20.73 g,150.00 mmol) and 540mL of mixed solvent (toluene: ethanol: water=2:1:1), and after three air substitutions with nitrogen, pd (PPh) was added 3 ) 4 (1.21 g,1.05 mmol) was stirred at reflux temperature for 3.5 hours, after the reaction was completed, cooled to room temperature, suction filtered to give a cake, and the cake was rinsed with ethanol, and finally the cake was quenched with toluene: ethanol=15:2 recrystallization gave intermediate C-57 (18.05 g, 75% yield) with HPLC purity ≡99.81%. Mass spectrum m/z:240.0468 (theory: 240.0454).
The preparation of intermediate C was carried out by the method of synthesis example 2, intermediate C-57, with corresponding replacement of the starting materials, as shown in the following table:
synthesis example 3: preparation of Compound 5
Synthesis of intermediate I-5
Under nitrogen, A-5 (13.62 g,80.00 mmol), B-5 (23.77 g,80.00 mmol), naOt-Bu (12.49 g,130.00 mmol) were dissolved in 650ml toluene solvent and Pd (OAc) was added under stirring 2 (0.24g，1.09mmol)、P(t-Bu) 3 (4.36 mL of a 0.5M toluene solution, 2.18 mmol) and the mixture of the above reactants was heated under reflux for 5h. After the reaction was completed, cooling to room temperature, adding distilled water, extracting with methylene chloride, standing for liquid separation, collecting an organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by distillation under reduced pressure, cooling for crystallization, suction-filtering, and subjecting the obtained solid to toluene: methanol=10:1 recrystallization gave intermediate I-5 (23.81 g, 77% yield), HPLC purity ≡99.89%. Mass spectrum m/z:386.1429 (theory: 386.1419).
Synthesis of Compound 5
Intermediate I-5 (19.32 g,50.00 mmol), C-5 (21.87 g,50.00 mmol) and NaOt-Bu (8.46 g,88.00 mmol) were dissolved in 440ml toluene solvent under nitrogen and Pd was added under stirring 2 (dba) 3 (0.69 g,0.75 mmol) and X-Phos (0.72, 1.50 mmol), and the mixture of the above-mentioned reactants was heated under reflux for 7 hours. After the reaction, cooling to room temperature, adding distilled water, extracting with dichloromethane, standing for liquid separation, collecting an organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by reduced pressure distillation, cooling for crystallization, suction-filtering, and recrystallizing the obtained solid with toluene to obtain the compound 5 (27.86 g, yield 75%), wherein the HPLC purity is not less than 99.98%. Mass spectrum m/z:742.2718 (theory: 742.2733). Theoretical element content (%) C 53 H 34 N 4 O: c,85.69; h,4.61; n,7.54. Measured element content (%): c,85.72; h,4.59; n,7.52.
Synthesis example 4: preparation of Compound 16
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-16, B-5 was replaced with equimolar B-16 and C-5 was replaced with equimolar C-16, compound 16 (27.64 g) was obtained with an HPLC purity of ≡ 99.95%. Mass spectrum m/z:717.2542 (theory of the following)Value: 717.2529). Theoretical element content (%) C 50 H 31 N 5 O: c,83.66; h,4.35; n,9.76. Measured element content (%): c,83.70; h,4.39; n,9.78.
Synthesis example 5: preparation of Compound 19
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-19, B-5 was replaced with equimolar B-19, and C-5 was replaced with equimolar C-19, compound 19 (24.18 g) was obtained, and HPLC purity was ≡ 99.92%. Mass spectrum m/z:644.2530 (theory: 644.2514). Theoretical element content (%) C 45 H 24 D 4 N 4 O: c,83.83; h,5.00; n,8.69. Measured element content (%): c,83.79; h,5.02; n,8.71.
Synthesis example 6: preparation of Compound 45
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-45, B-5 was replaced with equimolar B-16 and C-5 was replaced with equimolar C-45, compound 45 (30.57 g) was obtained with an HPLC purity of ≡ 99.97%. Mass spectrum m/z:793.2854 (theory: 793.2842). Theoretical element content (%) C 56 H 35 N 5 O: c,84.72; h,4.44; n,8.82. Measured element content (%): c,84.69; h,4.41; n,8.85.
Synthesis example 7: preparation of Compound 57
According to the same production method as that of Synthesis example 3, A-5 was replaced with equimolar A-57, B-5 was replaced with equimolar B-57, and C-5 was replaced with equimolar C-57, to obtain Compound 57 (24.39 g), HPLCThe purity is not less than 99.93 percent. Mass spectrum m/z:641.2228 (theory: 641.2216). Theoretical element content (%) C 44 H 27 N 5 O: c,82.35; h,4.24; n,10.91. Measured element content (%): c,82.33; h,4.22; n,10.88.
Synthesis example 8: preparation of Compound 71
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-71, B-5 was replaced with equimolar B-71 and C-5 was replaced with equimolar C-71, compound 71 (24.71 g) was obtained with an HPLC purity of ≡ 99.95%. Mass spectrum m/z:641.2205 (theory: 641.2216). Theoretical element content (%) C 44 H 27 N 5 O: c,82.35; h,4.24; n,10.91. Measured element content (%): c,82.37; h,4.21; n,10.87.
Synthesis example 9: preparation of Compound 82
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-82, B-5 was replaced with equimolar B-82 and C-5 was replaced with equimolar C-82, compound 82 (23.74 g) was obtained with an HPLC purity of ≡ 99.91%. Mass spectrum m/z:641.2207 (theory: 641.2216). Theoretical element content (%) C 44 H 27 N 5 O: c,82.35; h,4.24; n,10.91. Measured element content (%): c,82.38; h,4.22; n,10.88.
Synthesis example 10: preparation of Compound 84
According to the same production method as that of Synthesis example 3, A-5 was replaced with equimolar A-84, B-5 was replaced with equimolar B-16, and C-5 was replaced with equimolarC-84, compound 84 (25.03 g) was obtained with an HPLC purity of ≡ 99.96%. Mass spectrum m/z:641.2206 (theory: 641.2216). Theoretical element content (%) C 44 H 27 N 5 O: c,82.35; h,4.24; n,10.91. Measured element content (%): c,82.37; h,4.20; n,10.89.
Synthesis example 11: preparation of Compound 118
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-118, B-5 was replaced with equimolar B-118 and C-5 was replaced with equimolar C-118, compound 118 (27.45 g) was obtained with an HPLC purity of ≡99.94%. Mass spectrum m/z:741.2540 (theory: 741.2529). Theoretical element content (%) C 52 H 31 N 5 O: c,84.19; h,4.21; n,9.44. Measured element content (%): c,84.21; h,4.18; n,9.47.
Synthesis example 12: preparation of Compound 132
According to the same manner as that of Synthesis example 3, A-5 was replaced with equimolar A-132, B-5 was replaced with equimolar B-132, and C-5 was replaced with equimolar C-132, to give Compound 132 (23.75) having an HPLC purity of ≡ 99.98%. Mass spectrum m/z:650.2766 (theory: 650.2781). Theoretical element content (%) C 44 H 18 D 9 N 5 O: c,81.21; h,5.57; n,10.76. Measured element content (%): c,81.17; h,5.60; n,10.78.
Synthesis example 13: preparation of Compound 133
According to the same production method as that of Synthesis example 3, A-5 was replaced with equimolar oneSubstitution of A-133, B-5 for equimolar B-16 and C-5 for equimolar C-45 gave compound 133 (27.73 g) with an HPLC purity of > 99.93%. Mass spectrum m/z:729.2433 (theory: 729.2416). Theoretical element content (%) C 52 H 31 N 3 O 2 : c,85.58; h,4.2s8; n,5.76. Measured element content (%): c,85.61; h,4.30; n,5.73.
Synthesis example 14: preparation of Compound 181
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-181, B-5 was replaced with equimolar B-181 and C-5 was replaced with equimolar C-181, compound 181 (26.27 g) was obtained with an HPLC purity of ≡99.97%. Mass spectrum m/z:729.2430 (theory: 729.2416). Theoretical element content (%) C 52 H 31 N 3 O 2 : c,85.58; h,4.28; n,5.76. Measured element content (%): c,85.55; h,4.30; n,5.78.
Synthesis example 15: preparation of Compound 208
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-208, B-5 was replaced with equimolar B-16, and C-5 was replaced with equimolar C-45, compound 208 (26.17 g) was obtained with an HPLC purity of ≡99.94%. Mass spectrum m/z:679.2248 (theory: 679.2260). Theoretical element content (%) C 48 H 29 N 3 O 2 : c,84.81; h,4.30; n,6.18. Measured element content (%): c,84.78; h,4.26; n,6.20.
Synthesis example 16: preparation of Compound 232
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-232, B-5 was replaced with equimolar B-19, and C-5 was replaced with equimolar C-232, compound 232 (22.46 g) was obtained with an HPLC purity of ≡99.91%. Mass spectrum m/z:632.2225 (theory: 632.2212). Theoretical element content (%) C 43 H 28 N 4 O 2 : c,81.63; h,4.46; n,8.86. Measured element content (%): c,81.59; h,4.48; n,8.90.
Synthesis example 17: preparation of Compound 237
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-237, B-5 was replaced with equimolar B-57, and C-5 was replaced with equimolar C-237, compound 237 (25.05 g) was obtained, and HPLC purity was ≡ 99.96%. Mass spectrum m/z:695.2042 (theory: 695.2031). Theoretical element content (%) C 48 H 29 N 3 OS: c,82.85; h,4.20; n,6.04. Measured element content (%): c,82.80; h,4.18; n,6.06.
Synthesis example 18: preparation of Compound 252
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-252, B-5 was replaced with equimolar B-16 and C-5 was replaced with equimolar C-45, compound 252 (27.57 g) was obtained with an HPLC purity of ≡ 99.95%. Mass spectrum m/z:706.2353 (theory: 706.2369). Theoretical element content (%) C 49 H 30 N 4 O 2 : c,83.27; h,4.28; n,7.93. Measured element content (%): c,83.30; h,4.25; n,7.88.
Synthesis example 19: preparation of Compound 289
According to the same manner as that of Synthesis example 3, A-5 was replaced with equimolar A-289, B-5 was replaced with equimolar B-289, and C-5 was replaced with equimolar C-289, to obtain compound 289 (28.78 g), which had an HPLC purity of > 99.92%. Mass spectrum m/z:832.2850 (theory: 832.2838). Theoretical element content (%) C 59 H 36 N 4 O 2 : c,85.08; h,4.36; n,6.73. Measured element content (%): c,85.11; h,4.39; n,6.69.
Synthesis example 20: preparation of Compound 299
According to the same manner as in Synthesis example 3 except that A-5 was replaced with equimolar A-299, B-5 was replaced with equimolar B-16, and C-5 was replaced with equimolar C-45, compound 299 (29.14 g) was obtained with an HPLC purity of ≡99.97%. Mass spectrum m/z:756.2511 (theory: 756.2525). Theoretical element content (%) C 53 H 32 N 4 O 2 : c,84.11; h,4.26; n,7.40. Measured element content (%): c,84.08; h,4.21; n,7.37.
Synthesis example 21: preparation of Compound 339
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According to the same manner as in Synthesis example 3 except that A-5 was replaced with equimolar A-339, B-5 was replaced with equimolar B-339, and C-5 was replaced with equimolar C-339, compound 339 (24.99 g) was obtained, and HPLC purity was ≡ 99.93%. Mass spectrum m/z:703.2423 (theory: 703.2406). Theoretical element content (%) C 46 H 33 N 5 OS: c,78.50; h,4.73; n,9.95. Measured element content (%): c,78.45; h,4.69; n,9.98.
Synthesis example 22: preparation of Compound 367
According to the same production method as that of Synthesis example 3, A-5 was replaced with equimolar A-367, B-5 was replaced with equimolar B-367, and C-5 was replaced with equimolar C-367, to obtain Compound 367 (31.60 g), and HPLC purity was. Mass spectrum m/z:853.3611 (theory: 853.3626). Theoretical element content (%) C 60 H 27 D 10 N 5 O: c,84.38; h,5.54; n,8.20. Measured element content (%): c,84.41; h,5.49; n,8.25.
Synthesis example 23: preparation of Compound 371
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-371, B-5 was replaced with equimolar B-371, and C-5 was replaced with equimolar C-371, compound 371 (24.21 g) was obtained, which had an HPLC purity of ≡99.90%. Mass spectrum m/z:691.2359 (theory: 691.2372). Theoretical element content (%) C 48 H 29 N 5 O: c,83.34; h,4.23; n,10.12. Measured element content (%): c,83.32; h,4.25; n,10.09.
Synthesis example 24: preparation of Compound 401
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-45, B-5 was replaced with equimolar B-401 and C-5 was replaced with equimolar C-45, compound 401 (30.78 g) was obtained with an HPLC purity of ≡ 99.95%. Mass spectrum m/z:809.2628 (theory: 809.2613). Theoretical element content (%) C 56 H 35 N 5 S: c,83.04; h,4.36; n,8.65. Measured element content (%): c,83.07; h,4.40; n,8.62.
Synthesis example 25: preparation of Compound 423
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-423, B-5 was replaced with equimolar B-423 and C-5 was replaced with equimolar C-423, compound 423 (24.01 g) was obtained with an HPLC purity of ≡ 99.96%. Mass spectrum m/z:657.1969 (theory: 657.1987). Theoretical element content (%) C 44 H 27 N 5 S: c,80.34; h,4.14; n,10.65. Measured element content (%): c,80.36; h,4.09; n,10.62.
Synthesis example 26: preparation of Compound 466
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-466, B-5 was replaced with equimolar B-466 and C-5 was replaced with equimolar C-466, compound 466 (26.48 g) was obtained with an HPLC purity of ≡99.92%. Mass spectrum m/z:745.2175 (theory: 745.2188). Theoretical element content (%) C 52 H 31 N 3 OS: c,83.73; h,4.19; n,5.63. Measured element content (%): c,83.69; h,4.21; n,5.66.
Synthesis example 27: preparation of Compound 518
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-518, B-5 was replaced with equimolar B-518, and C-5 was replaced with equimolar C-518, compound 518 (24.29 g) was obtained, and HPLC purity was ≡ 99.94%. Mass spectrum m/z:647.1765 (theory: 647.1780). Theoretical element content (%) C 42 H 25 N 5 OS: c,77.88; h,3.89; n,10.81. Measured element content (%): c,77.90; h,3.86; n,10.78.
Synthesis example 28: preparation of Compound 551
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-551, B-5 was replaced with equimolar B-551 and C-5 was replaced with equimolar C-551, compound 551 (27.30 g) was obtained, and HPLC purity was ≡ 99.93%. Mass spectrum m/z:802.2750 (theory: 802.2733). Theoretical element content (%) C 58 H 34 N 4 O: c,86.76; h,4.27; n,6.98. Measured element content (%): c,86.80; h,4.30; n,6.96.
Synthesis example 29: preparation of Compound 555
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-555, B-5 was replaced with equimolar B-555, and C-5 was replaced with equimolar C-555, compound 555 (25.26 g) was obtained, and HPLC purity was ≡ 99.95%. Mass spectrum m/z:742.2752 (theory: 742.2733). Theoretical element content (%) C 53 H 34 N 4 O: c,85.69; h,4.61; n,7.54. Measured element content (%): c,85.70; h,4.59; n,7.53.
Synthesis example 30: preparation of Compound 579
According to a production method similar to that of Synthesis example 3, A-5 was replaced with equimolar A-579, B-5 was replaced with equimolar B-579, and C-5 was replaced with equimolar C-579, whereby Compound 579 (26.72 g) was obtained, and HPLC purity was > 99.96%. Mass spectrum m/z:785.3328 (theory: 785.3344). Theoretical element content (%) C 57 H 35 D 4 N 3 O: c,87.10; h,5.51; n,5.35. Actual measurement elementContent (%) of element: c,87.09; h,5.49; n,5.38.
Synthesis example 31: preparation of Compound 593
According to the same manner as that of Synthesis example 3 except that A-5 was replaced with equimolar A-593, B-5 was replaced with equimolar B-593 and C-5 was replaced with equimolar C-593, compound 593 (29.22 g) was obtained with an HPLC purity of > 99.98%. Mass spectrum m/z:846.2803 (theory: 846.2817). Theoretical element content (%) C 60 H 38 N 4 S: c,85.08; h,4.52; n,6.61. Measured element content (%): c,85.10; h,4.53; n,6.59.
Device example 1
Firstly, placing an ITO/Ag/ITO substrate in distilled water for ultrasonic cleaning for 3 times, carrying out ultrasonic cleaning for 15 minutes each time, carrying out ultrasonic cleaning by sequentially using solvents such as isopropanol, acetone and methanol after the distilled water is cleaned, carrying out ultrasonic cleaning for 10 minutes each time, and drying at 120 ℃ after the cleaning is finished.
Evaporating NPNPB with the thickness of 15nm on the cleaned ITO/Ag/ITO substrate by adopting a vacuum evaporation method to serve as a hole injection layer material; evaporating a compound NPB with the thickness of 80nm on the hole injection layer to be used as a hole transport layer material; vapor deposition of TcTa: ir (piq) on the hole transport layer 2 (acac) =98:2 (mass ratio) as a light-emitting layer, the vapor deposition thickness was 40nm; vapor plating BAlq on the light-emitting layer as a hole blocking layer, wherein the vapor plating thickness is 40nm; evaporating TPBi and Liq (doping mass ratio is 1:1) on the hole blocking layer as an electron transport layer, wherein the evaporating thickness is 30nm; evaporating LiF as an electron injection layer on the electron transport layer, wherein the evaporating thickness is 1.0nm; vapor deposition of Mg on the electron injection layer: ag=1:9 (doping mass ratio 1:1) as a cathode, evaporation thickness was 12nm, and then compound 5 was evaporated as a cap layer on the cathode, evaporation thickness was 70nm, thereby preparing an organic electroluminescent device.
Device examples 2 to 29
An organic electroluminescent device was produced by the same production method as in device example 1, except that compound 5 in device example 1 was replaced with compound 16, compound 19, compound 45, compound 57, compound 71, compound 82, compound 84, compound 118, compound 132, compound 133, compound 181, compound 208, compound 232, compound 237, compound 252, compound 289, compound 299, compound 339, compound 367, compound 371, compound 401, compound 423, compound 466, compound 518, compound 551, compound 555, compound 579 or compound 593, respectively, as a capping layer material.
Comparative device examples 1 to 3
An organic electroluminescent device was manufactured by the same manufacturing method as device example 1, except that compound 5 in device example 1 was replaced with comparative compound 1, comparative compound 2 or comparative compound 3, respectively, as a capping layer material.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectral scanning luminance meter manufactured by Photo Research, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. Life testing an M6000 OLED life test system from McScience was used. The environment tested was atmospheric and the temperature was room temperature.
Examples 1 to 29 of the inventive devices, and the results of testing the light emission characteristics of the organic electroluminescent devices obtained in comparative examples 1 to 3 are shown in table 1 below.
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As can be seen from the data results in table 1, the triarylamine derivative of the present invention is applied as a capping material in an organic electroluminescent device, and increases the light extraction efficiency by effectively reducing the total reflection of light inside the device, thereby improving the luminous efficiency and the service life of the device.
It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.

Claims (10)

1. A triarylamine derivative is characterized in that the triarylamine derivative has a structure shown in a formula I,
in formula I, x, equal to or different from each other, are chosen from CH or N atoms, and at least two x are chosen from N atoms, said x being chosen from C atoms when x is bonded to other groups;
y is selected from O or S;
the Ar is as follows 1 Any one selected from the groups shown in the formulas II-1 to II-11;
the z are identical or different from each other and are selected from CH or N atoms, when z is bonded to other groups, the z is selected from C atoms, and formula II-1
At least one z in each group of formula II-9 is selected from N atoms;
t is selected from any one of O, S, N (R); the R is selected from any of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroarylOne of the two; or R can be directly linked to L 1 Bonding;
said Q is selected from O, S, C (R x R y ) Or N (R) z )；
The R is x 、R y Are the same or different from each other, and are selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring groups; or R is x 、R y Any one of them can be directly connected with L 1 Bonding, or R x 、R y Can be interconnected to form a ring as shown below;
the R is 4 Selected from hydrogen, deuterium or any one of the following groups substituted or unsubstituted by one or more deuterium, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl or terphenyl;
The p is 1 Selected from 0, 1, 2, 3 or 4, p 2 Selected from 0, 1, 2, 3, 4, 5 or 6, p 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8,p 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, p 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, p 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, p 7 Selected from 0, 1 or 2.
The R is z Selected from substituted or unsubstitutedAny one of an alkyl group of C1 to C12, an alkenyl group of substituted or unsubstituted C2 to C12, a cycloalkyl group of substituted or unsubstituted C3 to C12, an aryl group of substituted or unsubstituted C6 to C30, a heteroaryl group of substituted or unsubstituted C2 to C30, an aromatic ring of substituted or unsubstituted C6 to C30 and a condensed ring group of an aliphatic ring of C3 to C30; or R is z Can be directly connected with L 1 Bonding;
the ring A and the ring B are the same or different and are selected from any one of an unsubstituted, substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted N-heterocyclic benzene ring and a substituted or unsubstituted N-heterocyclic naphthalene ring;
the R is 1 Is the same or different from each other, and is selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C7 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring;
The a 1 Selected from 0, 1, 2, 3, 4 or 5, said a 2 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said a 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, said a 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said a 5 Selected from 0, 1, 2, 3 or 4, said a 6 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said a 7 Selected from 0, 1, 2 or 3, when two or more R's are present 1 When two or more R' s 1 Identical or different from each other, or adjacent two R 1 May be linked to each other to form a substituted or unsubstituted ring;
the R is a 、R b 、R c Identical or different from each other, selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroarylAny one of a group, a substituted or unsubstituted C6 to C30 aromatic ring and a condensed ring group of a C3 to C30 aliphatic ring;
the m is 1 Selected from 0, 1, 2, 3, 4, 5 or 6, when two or more R's are present a When two or more R' s a Identical or different from each other, or adjacent two R' s a May be linked to each other to form a substituted or unsubstituted ring;
The m is 2 Selected from 0, 1, 2, 3 or 4, when two or more R's are present b When two or more R' s b Identical or different from each other, or adjacent two R' s b May be linked to each other to form a substituted or unsubstituted ring;
the m is 3 Selected from 0, 1, 2, 3, 4 or 5, when two or more R's are present c When two or more R' s c The same or different from each other;
the L is 0 、L 1 Are the same or different from each other, and are selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, bivalent substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring group and combination thereof.
2. A triarylamine derivative as set forth in claim 1 wherein said compound of formula ISelected from any one of the structures shown below,
the R is c Selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen or any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, C1 to C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, goldAn alkyl group, a norbornyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a quinoxalinyl group, a naphthyridinyl group, a benzocyclopropanyl group, a benzocyclobutanyl group, a benzocyclopentanyl group, a benzocyclohexenyl group, or a benzocycloheptanyl group;
Said b 1 Selected from 0, 1, 2, 3, 4 or 5, said b 2 Selected from 0, 1, 2, 3 or 4, said b 3 Selected from 0, 1, 2 or 3, said b 4 Selected from 0, 1 or 2, said b 5 Selected from 0 or 1, when two or more R's are present c When two or more R' s c The same as or different from each other.
3. A triarylamine derivative as set forth in claim 1 wherein said compound of formula ISelected from any one of the structures shown below,
the c 1 Selected from 1, 2, 3, 4 or 5, said c 2 Selected from 1, 2, 3 or 4, said c 3 Selected from 1, 2 or 3.
4. A triarylamine derivative as set forth in claim 1 wherein said compound of formula ISelected from any one of the structures shown below,
the R is a 、R b The same as or different from each other, selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen atom, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornane, adamantane, phenyl, biphenyl, terphenyl, naphthalene, anthryl, phenanthrene, triphenylene, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9' -spirobifluorenyl, furanyl, dibenzofuranyl, thienyl, dibenzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridine, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, deuteromethyl, deuteroethyl, deuterated ethyl, and deuterated isopropyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, methyl-substituted adamantyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthryl, deuterated phenanthryl, deuterated triphenylyl, deuterated fluorenyl, deuterated furanyl, deuterated dibenzofuranyl, deuterated thienyl, deuterated dibenzothienyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, cyano-substituted phenyl, cyano-substituted biphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, trifluoromethyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, deuterated methyl-substituted phenyl Any one of deuterated isopropyl substituted phenyl and deuterated tertiary butyl substituted phenyl;
said n 1 Selected from 0, 1, 2, 3, 4, 5 or 6, said n 2 Selected from 0, 1, 2 or 3, said n 3 Selected from 0, 1, 2, 3, 4 or 5, said n 4 Selected from 0, 1, 2, 3 or 4, said n 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, when two or more R's are present a 、R b When two or more R' s a 、R b The same as or different from each other.
5. A triarylamine derivative as set forth in claim 1 wherein Ar is 1 Selected from any one of the structures shown below;
the z are identical or different from each other and are selected from CH or N atoms, and at least one z in each group is selected from N atoms; when z is bonded to other groups, the z is selected from a C atom;
the R is 1 Are identical or different from each other and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen or substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, dibenzofuranyl, dibenzothienyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, or benzocycloheptanyl;
Said d 1 Selected from 0, 1, 2, 3 or 4, said d 2 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said d 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, said d 4 Selected from 0,1. 2, 3, 4, 5 or 6, said d 5 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, said d 6 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said d 7 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said d 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said d 9 Selected from 0, 1, 2 or 3, when two or more R's are present 1 When two or more R' s 1 The same as or different from each other.
6. A triarylamine derivative as set forth in claim 1 wherein Ar is 1 Selected from any one of the structures shown below;
said Q is selected from O, S, C (R x R y) Or N (R) z )；
The R is x 、R y Are identical or different from each other and are selected from any one of hydrogen, deuterium or a group substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl or benzocycloheptanyl; or R is x 、R y Any one of them can be usedTo be directly connected with L 1 Bonding, or R x 、R y Can be interconnected to form a ring as shown below;
the R is 4 Selected from hydrogen, deuterium or any one of the following groups substituted or unsubstituted by one or more deuterium, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl or terphenyl;
the p is 1 Selected from 0, 1, 2, 3 or 4, p 2 Selected from 0, 1, 2, 3, 4, 5 or 6, p 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8,p 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, p 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, p 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, p 7 Selected from 0, 1 or 2.
The R is z Any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, alkyl of C1 to C12: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl or benzocycloheptanyl; or R is z Can be directly connected with L 1 Bonding;
t is selected from any one of O, S, N (R);
the R is selected from any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl and C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, dibenzofuranyl, dibenzothienyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, or benzocycloheptanyl; or R can be directly linked to L 1 And (5) bonding.
7. A triarylamine derivative as set forth in claim 1 wherein said L 0 、L 1 Are identical or different from each other, are selected from single bonds or any one of the structures shown below,
the R is 2 Are identical or different from each other and are selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen or substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, C1-C12 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl or benzocycloheptanyl;
Said e 1 Selected from 0, 1, 2, 3 or 4, said e 2 Selected from 0, 1, 2 or 3, said e 3 Selected from 0, 1 or 2, said e 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said e 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, saide 6 Selected from 0, 1, 2, 3, 4, 5 or 6, said e 7 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, when two or more R's are present 2 When two or more R' s 2 The same as or different from each other.
8. A triarylamine derivative as set forth in claim 1 wherein said triarylamine derivative is selected from any one of the following structures,
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9. an organic electroluminescent device comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside any one of the anode and the cathode, characterized in that the organic layer comprises at least one or more of the triarylamine derivatives as described in any one of claims 1 to 8.
10. An organic electroluminescent device according to claim 9, wherein the organic layer is located outside any one of the anode and the cathode, wherein the organic layer comprises a cover layer comprising at least one or more of the triarylamine derivatives according to any one of claims 1 to 8.
CN202311054758.9A 2023-08-21 2023-08-21 Triarylamine derivative and organic electroluminescent device thereof Pending CN117088859A (en)

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