CN116554218A - Triarylamine derivative and organic electroluminescent device thereof - Google Patents

Triarylamine derivative and organic electroluminescent device thereof Download PDF

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CN116554218A
CN116554218A CN202310573647.2A CN202310573647A CN116554218A CN 116554218 A CN116554218 A CN 116554218A CN 202310573647 A CN202310573647 A CN 202310573647A CN 116554218 A CN116554218 A CN 116554218A
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unsubstituted
substituted
different
trifluoromethyl
group
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孙月
陆影
杜明珠
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Changchun Hyperions Technology Co Ltd
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Changchun Hyperions Technology Co Ltd
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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 performance of the organic electroluminescent device in the prior art, the invention provides the triarylamine derivative and the organic electroluminescent device thereof, and the triarylamine derivative provided by the invention has high glass transition temperature (Tg), good thermal stability and uniform and stable film forming property, and can be used as a coating material in the organic electroluminescent device to increase the extraction efficiency of light in the device, thereby improving the luminous efficiency of the device and prolonging the service life.

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
With the unprecedented development of technology and society, computer technology and internet technology are also developing rapidly, human society gradually enters a brand-new information age, and display technology is used as a communication medium between people and information, so that people have increasingly high requirements, and an Organic Light-Emitting Diode (OLED) is a novel flat panel display technology with huge prospects, which has been developed rapidly in recent decades, and is widely applied to various fields such as display and illumination, and the OLED has so many applications mainly due to the advantages of high efficiency, high brightness, low driving voltage, good flexibility, wide viewing angle, fast response speed, high resolution, wide material selection range and the like, so that the OLED becomes a research focus of related industries at home and abroad based on the advantages.
Electroluminescent refers to the physical phenomenon that an organic photoelectric material emits light under the action of current or an electric field, and can directly convert electric energy into light energy. The organic electroluminescent device can be divided into a single-layer device, a double-layer device, a multi-layer device and the like according to the structure, the multi-layer device is composed of an anode, a cathode and an organic layer, the organic layer comprises a hole injection layer, a hole transmission layer, an electron blocking layer, a luminescent layer, a hole blocking layer, an electron transmission layer, an electron injection layer and other functional layers, and the multi-layer structure can fully play the roles of the organic layers, balance the transmission of carriers and further improve the overall performance of the device.
However, there are many technical problems in the development of the current organic electroluminescent devices, especially how to improve the luminous efficiency and prolong the service life. Because of the huge difference between the external quantum efficiency and the internal quantum efficiency of the OLED, the device has about 20% of light-emitting efficiency, the development of the OLED is seriously affected, nearly 80% of light cannot be emitted, the light is limited in the device to be dissipated by heat, excessive heat accumulation can affect the service life of the material, the stable transmission of carriers is damaged, and water and oxygen in the air can enter the device when serious, so that the device has rapid roll-off of efficiency. Therefore, how to improve the light-emitting efficiency of the device has a profound meaning to the development of the OLED, in order to solve the problem, it is proposed to add a cover layer on the electrode, however, the development of the organic electroluminescent material in the present stage is still not perfect, and the research on the cover layer material is less, so most of the performances of the existing cover layer material are poor, and the existing cover layer material cannot meet the current requirement.
Therefore, the design of the coating material with high glass transition temperature, good thermal stability and good film forming property can effectively couple out light trapped in the device, enhance the light extraction efficiency, further improve the luminous efficiency of the device and prolong the service life of the device, and is a problem which needs to be solved at present.
Disclosure of Invention
In order to obtain an organic electroluminescent device with high luminous efficiency and long service life, the invention provides a triarylamine derivative and the organic electroluminescent device thereof.
The invention provides a triarylamine derivative, which has a structure shown as a formula I,
in formula I, the Y is selected from O, S, C (R) 2 Any one of N (R);
r is the same or different from each other and is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl, or R can be directly combined with L 0 Bonding;
the z are the same or different from each other and are selected from CH or N atoms, and when z is bonded with other groups, the z is selected from C atoms;
the R is z Are identical or different from each other and are selected from F, CF 3 、{Si(R 1 ) 3 }；
The R is 1 Are identical or different from each other and are selected from substituted or unsubstituted C1-C12 alkyl groups;
wherein n is selected from 1, 2, 3, 4 or 5, when two or more R's are present z When two or more R' s z Identical or different from each other, when R z When selected from F, n is selected from 5;
the Ar is as follows 2 Selected from any one of the groups shown below,
the x are identical or different from each other and are selected from CH or N atoms, and when x is bonded with other groups, the x is selected from C atoms;
the t is 1 Selected from O, S, N (R) 4 )、C(R 5 ) 2 Any one of the above, t 2 Any one selected from CH and N atoms;
the R is 4 、R 5 Are identical or different from each other and are selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R 4 、R 5 Can be directly connected with L 2 Bonding;
the Rx and Ry are the same or different from each other and are selected from any one of hydrogen, deuterium, 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 and substituted or unsubstituted C2-C30 heteroaryl, or Rx and Ry can be mutually connected to form a substituted or unsubstituted ring, or Rx and Ry can be directly connected with L 2 Bonding;
the R is 2 、R 3 Are the same or different from each other, and are selected from any one of hydrogen, deuterium, trifluoromethyl, fluorine, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the m is 1 Selected from 0, 1, 2, 3, 4 or 5, said m 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said m 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said m 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said m 5 Selected from 0, 1 or 2, said m 6 Selected from 0, 1, 2, 3,4. 5, 6, 7 or 8, said m 7 Selected from 0, 1, 2, 3 or 4, when two or more R's are present 2 When two or more R' s 2 Identical or different from each other, or adjacent two R' s 2 May be linked to each other to form a substituted or unsubstituted ring;
the Ar is as follows 1 Any one of 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;
The L is 0 Selected from one or more R c Substituted or unsubstituted: any one of C6-C30 arylene, C2-C30 heteroarylene, divalent C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring group;
the R is c Are the same or different from each other, and are selected from any one of trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the L is 1 、L 2 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 R is a 、R b Identical to or different from each other, any one selected from hydrogen, deuterium, trifluoromethyl, fluorine, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, 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 group;
Said n 1 Selected from 0, 1 or 2, when two or more R's are present a When two or more R' s a The same or different from each other;
said n 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 Can be linked to each other to form a substituted or unsubstituted: an aromatic or heteroaromatic ring.
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 shown in the formula I provided by the invention is applied to an organic electroluminescent device as a coating material, and can obviously improve the luminous efficiency of the device and prolong the service life, because the triarylamine derivative shown in the formula I has high glass transition temperature (Tg), high thermal stability, difficult decomposition and difficult crystallization at high temperature, good film forming property, and reduces the generation of Joule heat in the device, thereby improving the service performance of the device.
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 the present specification, when the position of a substituent on a ring is not fixed, it means that it can be attached to the phase of the ringAny one of the sites should be selectable. For example, the number of the cells to be processed,can indicate-> Can represent Can indicate-> And so on.
In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to either of the two or two rings, in particular to either of the respective selectable sites of the rings. For example, the number of the cells to be processed, Can indicate-> Can indicate->And 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.
As used herein, "substituted or unsubstituted silyl" refers to-Si (R) k ) 3 A group wherein each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic rings. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably3 to 10, most preferably 3 to 7. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl. Preferably, the "substituted or unsubstituted C1-C25 alkylsilyl" refers to a silyl group substituted with a substituted or unsubstituted C1-C25 alkyl group, which is preferably substituted with 3 alkyl groups, and examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, etc., 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 3 to 12 carbon atoms, and cycloalkyl according to the present invention means a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably 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 refers to 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 from 2 to 30 carbon atoms, particularly preferably from 2 to 18 carbon atoms, most preferably from 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. As the polycyclic arylene group, there may be mentioned a biphenylene groupPhenyl, terphenyl, tetra-biphenyl, and the like, but are not limited thereto. 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 C1-C25 alkylsilyl 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, C1-C25 alkylsilyl, 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, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, 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, benzocyclopropanyl group, benzocyclobutanyl group, benzocyclopentanyl group, benzocyclohexenyl group, benzocycloheptanyl group, benzocyclobutenyl group, benzocyclopentenyl group, benzocyclohexenyl group, benzocycloheptenyl group, pyrrolyl group, furyl group, thienyl group, benzofuryl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, triazinyl group, oxazolyl group, thiazolyl group, imidazolyl groupA group, a benzoxazolyl group, a benzothiazolyl group, a benzotriazole group, a benzimidazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a phenothiazinyl group, a phenoxazinyl group, an acridinyl group, 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 specification, the ring formed by the connection may be an aromatic ring or a non-aromatic ring, and may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a condensed ring, or the like, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornane, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, or the like, but is not limited thereto.
The invention provides a triarylamine derivative, which has a structure shown in a formula I,
in formula I, the Y is selected from O, S, C (R) 2 Any one of N (R);
r is the same or different from each other and is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl, or R can be directly combined with L 0 Bonding;
the z are the same or different from each other and are selected from CH or N atoms, and when z is bonded with other groups, the z is selected from C atoms;
the R is z Are identical or different from each other and are selected from F, CF 3 、{Si(R 1 ) 3 }；
The R is 1 Are identical or different from each other and are selected from substituted or unsubstituted C1-C12 alkyl groups;
wherein n is selected from 1, 2, 3, 4 or 5, when two or more R's are present z When two or more R' s z Identical or different from each other, when R z When selected from F, n is selected from 5;
the Ar is as follows 2 Selected from any one of the groups shown below,
the x are identical or different from each other and are selected from CH or N atoms, and when x is bonded with other groups, the x is selected from C atoms;
the t is 1 Selected from O, S, N (R) 4 )、C(R 5 ) 2 Any one of the above, t 2 Any one selected from CH and N atoms;
The R is 4 、R 5 Are identical or different from each other and are selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R 4 、R 5 Can be directly connected with L 2 Bonding;
the Rx and Ry are the same or different from each other and are selected from any one of hydrogen, deuterium, 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 and substituted or unsubstituted C2-C30 heteroaryl, or Rx and Ry can be mutually connected to form a substituted or unsubstituted ring, or Rx and Ry can be directly connected with L 2 Bonding;
the R is 2 、R 3 Are identical or different from each other and are selected from hydrogen, deuterium, trifluoromethyl, fluorine, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-to-unsubstitutedAny one of cycloalkyl group of C12, substituted or unsubstituted C1-C25 alkylsilyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group;
The m is 1 Selected from 0, 1, 2, 3, 4 or 5, said m 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said m 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said m 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said m 5 Selected from 0, 1 or 2, said m 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said m 7 Selected from 0, 1, 2, 3 or 4, when two or more R's are present 2 When two or more R' s 2 Identical or different from each other, or adjacent two R' s 2 May be linked to each other to form a substituted or unsubstituted ring;
the Ar is as follows 1 Any one of 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;
the L is 0 Selected from one or more R c Substituted or unsubstituted: any one of C6-C30 arylene, C2-C30 heteroarylene, divalent C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring group;
the R is c Are the same or different from each other, and are selected from any one of trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
The L is 1 、L 2 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 R is a 、R b Are identical or different from each other and are selected from hydrogenDeuterium, trifluoromethyl, fluorine, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, 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 group;
said n 1 Selected from 0, 1 or 2, when two or more R's are present a When two or more R' s a The same or different from each other;
said n 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 Can be linked to each other to form a substituted or unsubstituted: an aromatic or heteroaromatic ring.
Preferably, R 1 Are identical or different from each other and are selected from the group consisting of a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted tertiary butyl group, a substituted or unsubstituted pentyl group, a substituted or unsubstituted hexyl group, a substituted or unsubstituted heptyl group and a substituted or unsubstituted octyl group.
More preferably, R 1 Are identical or different from each other and are selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl and substituted or unsubstituted tertiary butyl.
Preferably, si (R 1 ) 3 Selected from trimethylsilyl, triethylsilyl, triisopropylsilyl, and tri-t-butylsilyl.
Preferably, the saidAny one selected from the following groups;
said Y is selected from O, S, C (R) 2 Any one of N (R);
the R are identical or different from each other and are selected from any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl and C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzothienyl, benzofuranyl, benzocyclopentyl or benzocyclohexenyl, or R may be directly linked to L 0 Bonding;
the a 1 Selected from 0, 1 or 2, said a 2 Selected from 0, 1, 2, 3 or 4, said a 3 Selected from 0, 1, 2 or 3, said a 4 Selected from 0 or 1.
Preferably, the saidAny one selected from the following groups;
said Y is selected from O, S, C (R) 2 Any one of N (R);
the R are identical or different from each other and are selected from any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl and C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentaneA group, a cyclohexenyl group, an adamantyl group, a norbornyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a quinoxalinyl group, a naphthyridinyl group, a benzothienyl group, a benzofuranyl group, a benzocyclopentenyl group, or a benzocyclohexenyl group, or R may be directly bonded to L 0 Bonding;
the R is a 、R b Identical to or different from each other, selected from hydrogen, deuterium, trifluoromethyl, fluorine or any one of the following groups substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine, C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzothienyl, benzofuranyl, benzocyclopentyl or benzocyclohexenyl;
Said b 1 Selected from 0, 1 or 2, said b 2 Selected from 0, 1, 2, 3 or 4, said b 3 Selected from 0 or 1, said b 4 Selected from 0, 1, 2, 3, 4, 5 or 6, said b 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said b 6 Selected from 0, 1, 2, 3, 4 or 5, said b 7 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said b 8 Selected from 0, 1, 2 or 3.
Preferably, the said: -Ar 1 - (Rz) n is selected from any one of the groups shown below;
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the R is 6 Are identical or different from each other and are selected from hydrogen, deuterium, trifluoromethyl, fluorine,Or any one of the following substituted or unsubstituted with one or more deuterium, trifluoromethyl, fluorine, C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl;
the c 1 Selected from 0, 1, 2, 3 or 4, said c 2 Selected from 0, 1, 2 or 3, said c 3 Selected from 0, 1 or 2, said c 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said c 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, said c 6 Selected from 0, 1, 2, 3, 4 or 5, said c 7 Selected from 0 or 1, said c 8 Selected from 0, 1, 2, 3, 4, 5 or 6, when two or more R's are present 6 When two or more R' s 6 Identical or different from each other, or adjacent two R 6 May be linked to each other to form a substituted or unsubstituted ring;
the q is 1 Selected from 1, 2, 3, 4 or 5, said q 2 Selected from 1, 2, 3 or 4, said q 3 Selected from 1, 2 or 3, said q 4 Selected from 1, 2, 3, 4, 5, 6 or 7, said q 5 Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9, said q 6 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.
Preferably, the said: -Ar 1 - (Rz) n is selected from any one of the groups shown below;
said g 1 Selected from 1, 2, 3 or 4, said g 2 Selected from 1, 2, 3, 4, 5 or 6, said g 3 Selected from 1, 2, 3, 4, 5, 6, 7 or 8; the p is 1 Selected from 1, 2, 3, 4 or 5, said p 2 Selected from 1, 2, 3 or 4, said p 3 Selected from 1, 2Or 3. Preferably, the Ar 2 Any one selected from the following groups;
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the t is 1 Selected from O, S, N (R) 4 )、C(R 5 ) 2 Any one of the above, t 2 Any one selected from CH and N atoms;
the R is 4 、R 5 Are identical or different from each other, and are selected from any one of the following groups substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine and C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl or naphthyridinyl, or R 4 、R 5 Can be directly connected with L 2 Bonding;
the R is 2 、R 3 Identical to or different from each other, selected from hydrogen, deuterium, trifluoromethyl, fluorine or any one of the following groups substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine, C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, or tri-tert-butylsilyl;
said d 1 Selected from 0, 1, 2, 3, 4 or 5, said d 2 Selected from 0, 1, 2, 3 or 4, said d 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said d 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said d 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said d 6 Selected from 0, 1, 2 or 3, said d 7 Selected from 0, 1 or 2, said d 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said d 10 Selected from 0, 1, 2, 3, 4, 5 or 6.
Preferably, the L 1 、L 2 Are the same or different from each other, and are selected from any one of single bonds or groups shown below;
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The R is 7 Are identical or different from each other and are selected from hydrogen, deuterium, trifluoromethyl, fluorine, or any one of the following groups substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine, C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl;
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 or 5, said e 7 Selected from 0 or 1, said e 8 Selected from 0,1. 2, 3, 4, 5 or 6.
Preferably, the L 0 Any one selected from the following groups;
the v are identical or different from each other and are selected from CH or N atoms, and when v is bonded with other groups, the v is selected from C atoms;
The R is c Are identical or different from each other and are selected from hydrogen, trifluoromethyl, fluorine, or any one of the following groups substituted or unsubstituted by one or more trifluoromethyl, fluorine, C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, or tri-tert-butylsilyl;
said f 1 Selected from 0, 1, 2, 3 or 4, said f 2 Selected from 0, 1 or 2, said f 3 Selected from 0, 1, 2 or 3, said f 4 Selected from 0, 1, 2, 3, 4 or 5, said f 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said f 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said f 7 Selected from 0 or 1, said f 8 Selected from 0, 1, 2, 3, 4, 5 or 6.
Preferably, the L 0 Any one selected from the group consisting of the following groups and combinations thereof;
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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 in the groups defined above, even when the structural forms shown in formula I are used as the basis.
The present invention provides a preparation method of a structure shown in formula I, which is prepared by carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. which are well known in the art, but the present invention is not limited thereto:
the structure of formula 1 was prepared using the synthetic route shown below:
preparation of raw material a:
preparation of raw material b:
preparation of raw material 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 、Ar 2 、L 0 、L 2 、R a 、R b 、z、Y、n 1 、n 2 The definition of (2) is the same as described above.
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 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 and 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.
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.
According to different light emitting directions, the organic electroluminescent device provided by the invention can be any one of a top emission device, a bottom emission device and a double-sided emission device;
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 present invention preferably uses a material having a high function 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. The triarylamine derivatives described herein are preferred.
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
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 raw materials a-186:
to the reaction flask was added d-186 (27.92 g,90.00 mmol), e-186 (15.48 g,90.00 mmol), pd (PPh) under nitrogen 3 ) 4 (1.16g，1.00mmol)、K 2 CO 3 (20.73 g,150 mmol) and 450mL (toluene: ethanol: water=2:1:1) of the mixed solvent, the mixture was stirred, and the mixed solution of the above-mentioned reactants was heated under reflux for 4 hours. After the reaction was completed, cooled to room temperature, distilled water was added, extracted with methylene chloride, left to stand for separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, concentrated by distillation under reduced pressure, and the obtained solid was recrystallized from toluene, and dried to give raw material a-186 (18.59 g, yield 75%); HPLC purity ∈ 99.72%. Mass spectrum m/z:275.0781 (theory: 275.0769).
The preparation method of the raw materials a-186 in synthetic example 1 is followed by corresponding replacement of the raw materials, namely the raw material a, which is shown in the following table:
synthesis example 2: preparation of raw material b-323:
d-323 (33.3) 2g，90.00mmol)、g-323(17.23g，90.00mmol)、Pd(PPh 3 ) 4 (1.16g，1.00mmol)、K 2 CO 3 (20.73 g,150 mmol) and 450mL (toluene: ethanol: water=2:1:1) of the mixed solvent, the mixture was stirred, and the mixed solution of the above-mentioned reactants was heated under reflux for 3.5 hours. After the completion of the reaction, cooled to room temperature, distilled water was added, extracted with dichloromethane, the mixture was left to stand, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure, and the obtained solid was purified with toluene: ethanol=10:1 recrystallisation, drying gives starting material b-323 (24.59 g, 77% yield), HPLC purity ≡99.81%. Mass spectrum m/z:354.0826 (theory: 354.0811).
The raw materials were replaced correspondingly, and the raw materials b/c were prepared according to the preparation method of the raw materials b-323 in synthetic example 2, and the raw materials are shown in the following table:
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synthesis example 3: preparation of Compound 34
Synthetic intermediate A-34:
a-34 (14.72 g,60.00 mmol), b-34 (17.95 g,60.00 mmol), pd (OAc) were added to the flask under nitrogen 2 (0.18g，0.80mmol)、P(t-Bu) 3 (3.20 mL of a 0.5M toluene solution, 1.60 mmol), naOt-Bu (11.53 g,120.00 mmol) and 300mL of toluene solvent, the mixture was stirred, and the mixture of the above reactants was heated under reflux for 5 hours. After the reaction, cooling to room temperature, adding distilled water, extracting with dichloromethane, standing for separating liquid, collecting organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by reduced pressure distillation, cooling for crystallization, and suction filtering to obtain solid Toluene was used: methanol=12:1 recrystallisation gives intermediate a-34 (21.14 g, 76% yield) with HPLC purity. Mass spectrum m/z:463.2317 (theory: 463.2300).
Synthesis of Compound 34:
intermediate A-34 (13.91 g,30.00 mmol), c-34 (10.36 g,30.00 mmol), pd under nitrogen 2 (dba) 3 (0.41 g,0.45 mmol), X-Phos (0.43 g,0.90 mmol), naOt-Bu (5.77 g,60.00 mmol) and 150ml toluene solvent, the mixture was stirred, and the mixed solution of the above 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 distillation under reduced pressure, cooling for crystallization, suction-filtering, and recrystallizing the obtained solid with toluene to obtain a compound 34 (16.16 g, yield 74%), wherein the HPLC purity is not less than 99.97%. Mass spectrum m/z:727.3646 (theory: 727.3634). Theoretical element content (%) C 53 H 49 NSi: c,87.43; h,6.78; n,1.92. Measured element content (%): c,87.41; h,6.80; n,1.89. Synthesis example 4: preparation of Compound 48
According to the same production method as that of Synthesis example 3, a-34 was replaced with equimolar a-48, b-34 with equimolar b-48, and c-34 with equimolar c-48, compound 48 (15.37 g, 73%) was obtained, HPLC purity ≡ 99.98%. Mass spectrum m/z:673.2667 (theory: 673.2655). Theoretical element content (%) C 44 H 43 NSSi 2 : c,78.40; h,6.43; n,2.08. Measured element content (%): c,78.38; h,6.42; n,2.11.
Synthesis example 5: preparation of Compound 96
Following the same procedure as in Synthesis example 3, a-34 was replaced with equal onesSubstitution of moles of a-96, b-34 for equimolar b-96 and c-34 for equimolar c-96 gives compound 96 (15.56 g) with an HPLC purity of ≡99.96%. Mass spectrum m/z:710.0861 (theory: 710.0875). Theoretical element content (%) C 37 H 16 F 10 N 2 S: c,62.54; h,2.27; n,3.94. Measured element content (%): c,62.56; h,2.30; n,3.92.
Synthesis example 6: preparation of Compound 123
According to the same production method as that of Synthesis example 3, a-34 was replaced with equimolar a-123, b-34 with equimolar b-123, and C-34 with equimolar C-123, compound 123 ((15.32 g), HPLC purity ≡ 99.95%. Mass Spectrometry m/z:699.1984 (theoretical value: 699.1997). Theoretical element content (%) C was obtained 44 H 27 F 6 NO: c,75.53; h,3.89; n,2.00. Measured element content (%): c,75.56; h,3.91; n,2.01.
Synthesis example 7: preparation of Compound 138
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-138, b-34 was replaced with equimolar b-48 and c-34 was replaced with equimolar c-48, compound 138 (15.20 g) was obtained with an HPLC purity of ≡99.98%. Mass spectrum m/z:657.1969 (theory: 657.1980). Theoretical element content (%) C 43 H 35 NS 2 Si: c,78.50; h,5.36; n,2.13. Measured element content (%): c,78.47; h,5.38; n,2.15.
Synthesis example 8: preparation of Compound 186
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-186, b-34 was replaced with equimolar b-186 and c-34 was replaced with equimolar c-186, compound 186 (15.14 g) was obtained with an HPLC purity of ≡99.96%. Mass spectrum m/z:681.1971 (theory: 681.1980). Theoretical element content (%) C 45 H 35 NS 2 Si: c,79.25; h,5.17; n,2.05. Measured element content (%): c,79.23; h,5.20; n,2.08.
Synthesis example 9: preparation of Compound 216
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According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-216, b-34 was replaced with equimolar b-216, and c-34 was replaced with equimolar c-48, compound 216 (14.08 g) was obtained with an HPLC purity of ≡99.98%. Mass spectrum m/z:625.2452 (theory: 625.2437). Theoretical element content (%) C 43 H 35 NO 2 Si: c,82.52; h,5.64; n,2.24. Measured element content (%): c,82.49; h,5.66; n,2.26.
Synthesis example 10: preparation of Compound 237
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-237, b-34 was replaced with equimolar b-237 and c-34 was replaced with equimolar c-237, compound 237 (16.76 g) was obtained, and HPLC purity was ≡ 99.94%. Mass spectrum m/z:775.2915 (theory: 775.2907). Theoretical element content (%) C 55 H 41 NO 2 Si: c,85.13; h,5.33; n,1.80. Measured element content (%): c,85.14; h,5.34; n,1.78.
Synthesis example 11: preparation of Compound 265
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-138, b-34 was replaced with equimolar b-48 and c-34 was replaced with equimolar c-96, compound 265 (15.00 g) was obtained with HPLC purity ≡ 99.97%. Mass spectrum m/z:675.1128 (theory: 675.1114). Theoretical element content (%) C 40 H 22 F 5 NS 2 : c,71.10; h,3.28; n,2.07. Measured element content (%): c,71.06; h,3.31; n,2.11. Synthesis example 12: preparation of Compound 288
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-138, b-34 was replaced with equimolar b-48 and c-34 was replaced with equimolar c-288, compound 288 (15.84 g) was obtained with an HPLC purity of ≡99.94%. Mass spectrum m/z:694.1345 (theory: 694.1360). Theoretical element content (%) C 42 H 25 F 3 N 2 OS 2 : c,72.61; h,3.63; n,4.03. Measured element content (%): c,72.59; h,3.65; n,4.06.
Synthesis example 13: preparation of Compound 323
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-323, b-34 was replaced with equimolar b-323, and c-34 was replaced with equimolar c-96, compound 323 (18.81 g) was obtained with an HPLC purity of ≡99.92%. Mass spectrum m/z:895.2522 (theory: 895.2510). Theoretical element content (%) C 60 H 34 F 5 NO 2 : c,80.44; h,3.83; n,1.56. Measured element content (%): c,80.41; h,3.79; n,1.58.
Synthesis example 14: preparation of Compound 340
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-138, b-34 was replaced with equimolar b-48 and c-34 was replaced with equimolar c-123, compound 340 (14.51 g) was obtained with an HPLC purity of ≡99.97%. Mass spectrum m/z:653.1443 (theory: 653.1459). Theoretical element content (%) C 41 H 26 F 3 NS 2 : c,75.32; h,4.01; n,2.14. Measured element content (%): c,75.29; h,4.03; n,2.17.
Synthesis example 15: preparation of Compound 412
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-216, b-34 was replaced with equimolar b-412 and c-34 was replaced with equimolar c-412, compound 412 (15.27 g) was obtained with an HPLC purity of ≡99.91%. Mass spectrum m/z:726.2716 (theory: 726.2703). Theoretical element content (%) C 50 H 38 N 2 O 2 Si: c,82.61; h,5.27; n,3.85. Measured element content (%): c,82.59; h,5.30; n,3.83.
Synthesis example 16: preparation of Compound 413
According to a production method similar to that of Synthesis example 3, a-34 was replaced with equimolar a-216, b-34 with equimolar b-48, and c-34 with equimolar c-48, compound 413 (14.44 g) was obtained with an HPLC purity of ≡ 99.98%. Mass spectrum m/z:641.2219 (theory: 641.2209). Theoretical element content (%) C 43 H 35 NOSSi: c,80.46; h,5.50; n,2.18. Measured element content (%): c,80.50; h,5.49; n,2.21.
Synthesis example 17: preparation of Compound 452
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-452, b-34 was replaced with equimolar b-452 and c-34 was replaced with equimolar c-452, compound 452 (14.83 g) was obtained with an HPLC purity of ≡99.94%. Mass spectrum m/z:658.2872 (theory: 658.2855). Theoretical element content (%) C 45 H 30 D 7 NSSi: c,82.02; h,6.73; n,2.13. Measured element content (%): c,82.05; h,6.70; n,2.09.
Synthesis example 18: preparation of Compound 476
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-476, b-34 was replaced with equimolar b-476 and c-34 was replaced with equimolar c-476, compound 476 (16.88 g) was obtained with an HPLC purity of ≡99.93%. Mass spectrum m/z:803.2438 (theory: 803.2454). Theoretical element content (%) C 48 H 36 F 7 NOSi: c,71.72; h,4.51; n,1.74. Measured element content (%): c,71.69; h,4.48; n,1.76.
Synthesis example 19: preparation of Compound 482
According to a production method similar to that of Synthesis example 3, a-34 was replaced with equimolar a-482, b-34 was replaced with equimolar b-48, and c-34 was replaced with equimolar c-48, whereby Compound 482 (14.86 g) was obtained with an HPLC purity of ≡99.98%. Mass spectrum m/z:651.2431 (theory: 651.2416). Theoretical element content (%) C 45 H 37 NSSi: c,82.91; h,5.72; n,2.15. Measured element content (%): c,82.88; h,5.69; n,2.17.
Synthesis example 20: preparation of Compound 489
According to the same production method as that of Synthesis example 3, a-34 was replaced with equimolar a-489, b-34 was replaced with equimolar b-489, and c-34 was replaced with equimolar b-489, to obtain Compound 489 (16.62 g), with an HPLC purity of > 99.90%. Mass spectrum m/z:779.2546 (theory: 779.2532). Theoretical element content (%) C 50 H 45 NS 2 Si 2 : c,76.97; h,5.81; n,1.80. Measured element content (%): c,76.95; h,5.79; n,1.81.
Synthesis example 21: preparation of Compound 502
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-482, b-34 was replaced with equimolar b-216, and c-34 was replaced with equimolar c-502, compound 502 (15.51 g) was obtained with HPLC purity ≡ 99.96%. Mass spectrum m/z:707.3032 (theory: 707.3040). Theoretical element content (%) C 48 H 45 NOSi 2 : c,81.42; h,6.41; n,1.98. Measured element content (%): c,81.45; h,6.37; n,1.97.
Synthesis example 22: preparation of Compound 512
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-482, b-34 was replaced with equimolar b-48, and c-34 was replaced with equimolar c-96, compound 512 (15.07 g) was obtained with HPLC purity of ≡99.97%. Mass spectrum m/z:669.1533 (theory: 669.1550). Theoretical element content (%) C 42 H 24 F 5 NS:75.33; h,3.61; n,2.09. The actual measured element containsAmount (%): 75.35; h,3.59; n,2.12. Synthesis example 23: preparation of Compound 522
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-522, b-34 was replaced with equimolar b-48, and c-34 was replaced with equimolar c-522, compound 522 (14.97 g) was obtained with an HPLC purity of ≡99.96%. Mass spectrum m/z:647.2482 (theory: 647.2498). Theoretical element content (%) C 42 H 41 NSSi 2 : c,77.85; h,6.38; n,2.16. Measured element content (%): c,77.81; h,6.40; n,2.20.
Synthesis example 24: preparation of Compound 544
According to the same production method as that of Synthesis example 3, substituting a-34 with equimolar a-544, substituting b-34 with equimolar b-48, and substituting c-34 with equimolar c-544, compound 544 (15.10 g) was obtained with an HPLC purity of ≡99.96%. Mass spectrum m/z:689.1625 (theory: 689.1612). Theoretical element content (%) C 42 H 25 F 6 NS: c,73.14; h,3.65; n,2.03. Measured element content (%): c,73.11; h,3.68; n,2.05. Synthesis example 25: preparation of Compound 556
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-556, b-34 was replaced with equimolar b-556 and c-34 was replaced with equimolar c-556, compound 556 (16.65 g) was obtained with HPLC purity of ≡99.94%. Mass spectrum m/z:781.2578 (theory: 781.2592). Theoretical element content (%) C 55 H 34 F 3 NO: c,84.49; h,4.38; n,1.79. Measured element content (%):C,84.51；H,4.34；N,1.81。
synthesis example 26: preparation of Compound 562
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-562, b-34 was replaced with equimolar b-562, and c-34 was replaced with equimolar c-562, compound 562 (15.55 g) was obtained with an HPLC purity of ≡99.92%. Mass spectrum m/z:709.9622 (theory: 709.9640). Theoretical element content (%) C 51 H 39 NOSi: c,86.28; h,5.54; n,1.97. Measured element content (%): c,86.30; h,5.57; n,1.96.
Synthesis example 27: preparation of Compound 564
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-564, b-34 was replaced with equimolar b-564 and c-34 was replaced with equimolar c-564, compound 564 (15.29 g) was obtained with HPLC purity ≡ 99.95%. Mass spectrum m/z:707.1535 (theory: 707.1518). Theoretical element content (%) C 42 H 24 F 7 NS: c,71.28; h,3.42; n,1.98. Measured element content (%): c,71.30; h,3.39; n,1.96.
Synthesis example 28: preparation of Compound 574
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-574, b-34 was replaced with equimolar b-574, and c-34 was replaced with equimolar c-48, compound 574 (16.27 g) was obtained with an HPLC purity of ≡99.93%. Mass spectrum m/z:752.2692 (theory: 752.2681). Theoretical element content (%) C 52 H 40 N 2 SSi：C82.94; h,5.35; n,3.72. Measured element content (%): c,82.98; h,5.37; n,3.69.
Synthesis example 29: preparation of Compound 580
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-580, b-34 was replaced with equimolar b-48, and c-34 was replaced with equimolar c-96, compound 580 (16.38 g) was obtained in an HPLC purity of ≡99.96%. Mass spectrum m/z:747.1755 (theory: 747.1768). Theoretical element content (%) C 46 H 26 F 5 N 3 S: c,73.89; h,3.50; n,5.62. Measured element content (%): c,73.92; h,3.49; n,5.64.
Synthesis example 30: preparation of Compound 582
According to a production method similar to that of Synthesis example 3, a-34 was replaced with equimolar a-582, b-34 was replaced with equimolar b-582, and c-34 was replaced with equimolar c-582, to obtain Compound 582 (14.33 g), with HPLC purity ≡ 99.95%. Mass spectrum m/z:645.1287 (theory: 645.1298). Theoretical element content (%) C 38 H 20 F 5 N 3 S: c,70.69; h,3.12; n,6.51. Measured element content (%): c,70.72; h,3.09; n,6.48.
Synthesis example 31: preparation of Compound 592
According to a production method similar to that of Synthesis example 3, a-34 was replaced with equimolar a-592, b-34 with equimolar b-592, and c-34 with equimolar c-123, compound 592 (14.28 g) was obtained with an HPLC purity of ≡ 99.97%. Mass spectrum m/z:634.1993 (theoretical value) : 634.1980). Theoretical element content (%) C 40 H 25 F 3 N 4 O: c,75.70; h,3.97; n,8.83. Measured element content (%): c,75.69; h,3.95; n,8.85.
Synthesis example 32: preparation of Compound 602
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-602, b-34 was replaced with equimolar b-48 and c-34 was replaced with equimolar c-48, compound 602 (14.47 g) was obtained with an HPLC purity of ≡99.98%. Mass spectrum m/z:642.2175 (theory: 642.2161). Theoretical element content (%) C 42 H 34 N 2 OSSi: c,78.47; h,5.33; n,4.36. Measured element content (%): c,78.51; h,5.35; n,4.33.
Synthesis example 33: preparation of Compound 611
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-611, b-34 was replaced with equimolar b-48, and c-34 was replaced with equimolar c-186, compound 611 (13.29 g) was obtained with an HPLC purity of ≡99.95%. Mass spectrum m/z:582.1635 (theory: 582.1620). Theoretical element content (%) C 36 H 30 N 2 S 2 Si: c,74.19; h,5.19; n,4.81. Measured element content (%): c,74.22; h,5.17; n,4.78.
Synthesis example 34: preparation of Compound 618
Following the same procedure as in Synthesis example 3, a-34 was replaced with equimolar a-602, b-34 with equimolar b-216, and c-34 with equimolar c-4 8, compound 618 (14.10 g) was obtained with an HPLC purity of > 99.98%. Mass spectrum m/z:626.2399 (theory: 626.2390). Theoretical element content (%) C 42 H 34 N 2 O 2 Si: c,80.48; h,5.47; n,4.47. Measured element content (%): c,80.51; h,5.44; n,4.50.
Synthesis example 35: preparation of Compound 664
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-664, b-34 was replaced with equimolar b-216, and c-34 was replaced with equimolar c-664, compound 664 (16.39 g) was obtained, and HPLC purity was ≡ 99.96%. Mass spectrum m/z:718.2459 (theory: 718.2474). Theoretical element content (%) C 48 H 38 N 2 OSSi: c,80.19; h,5.33; n,3.90. Measured element content (%): c,80.21; h,5.35; n,3.87.
Synthesis example 36: preparation of Compound 684
According to the same production method as that of Synthesis example 3, substituting a-34 with equimolar a-684, substituting b-34 with equimolar b-684, and substituting c-34 with equimolar c-684, compound 684 (16.19 g) was obtained, with HPLC purity ≡ 99.94%. Mass spectrum m/z:781.1848 (theory: 781.1833). Theoretical element content (%) C 49 H 30 F 3 N 3 S 2 : c,75.27; h,3.87; n,5.37. Measured element content (%): c,75.27; h,3.87; n,5.37.
Synthesis example 37: preparation of Compound 702
According to the same preparation method as that of Synthesis example 3Substitution of a-34 for equimolar a-702, b-34 for equimolar b-702, and c-34 for equimolar c-702 gave compound 702 (15.99 g) with an HPLC purity of ≡99.91%. Mass spectrum m/z:739.3616 (theory: 739.3606). Theoretical element content (%) C 51 H 45 D 4 NSSi: c,82.76; h,7.22; n,1.89. Measured element content (%): c,82.75; h,7.20; n,1.91.
Synthesis example 38: preparation of Compound 730
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-730, b-34 was replaced with equimolar b-730, and c-34 was replaced with equimolar c-730, compound 730 (13.23 g) was obtained with an HPLC purity of ≡99.93%. Mass spectrum m/z:612.1496 (theory: 612.1483). Theoretical element content (%) C 38 H 23 F 3 N 2 OS: c,74.50; h,3.78; n,4.57. Measured element content (%): c,74.48; h,3.81; n,4.60.
Synthesis example 39: preparation of Compound 736
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-736, b-34 was replaced with equimolar b-736, and c-34 was replaced with equimolar c-736, compound 736 (16.44 g) was obtained with HPLC purity ≡ 99.97%. Mass spectrum m/z:750.1732 (theory: 750.1718). Theoretical element content (%) C 44 H 23 F 9 N 2 : c,70.40; h,3.09; n,3.73. Measured element content (%): c,70.39; h,3.11; n,3.75.
Synthesis example 40: preparation of Compound 753
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-753, b-34 was replaced with equimolar b-753, and c-34 was replaced with equimolar c-753, compound 753 (15.18 g) was obtained, and HPLC purity was > 99.95%. Mass spectrum m/z:683.2822 (theory: 683.2834). Theoretical element content (%) C 45 H 40 F 3 NS: c,79.03; h,5.90; n,2.05. Measured element content (%): c,79.05; h,5.87; n,2.09.
Synthesis example 41: preparation of Compound 775
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-775, b-34 was replaced with equimolar b-775, and c-34 was replaced with equimolar c-123, compound 775 (17.30 g) was obtained, and HPLC purity was ≡99.93%. Mass spectrum m/z:789.2690 (theory: 789.2677). Theoretical element content (%) C 54 H 38 F 3 NS: c,82.10; h,4.85; n,1.77. Measured element content (%): c,82.08; h,4.83; n,1.80.
Synthesis example 42: preparation of Compound 790
According to the same manner as that of Synthesis example 3 except that a-34 was replaced with equimolar a-790, b-34 was replaced with equimolar b-790 and c-34 was replaced with equimolar c-790, compound 790 (12.56 g) was obtained with an HPLC purity of ≡99.90%. Mass spectrum m/z:606.2170 (theory: 606.2154). Theoretical element content (%) C 36 H 20 D 5 F 6 NO: c,71.28; h,4.98; n,2.31. Measured element content (%): c,71.30; h,4.95; n,2.29.
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 HI-1 and P-1 (the doping mass ratio is 97:3) on the cleaned ITO/Ag/ITO substrate by adopting a vacuum evaporation method as a hole injection layer, wherein the evaporation thickness is 12nm; evaporating HT-1 on the hole injection layer as a hole transport layer, wherein the evaporating thickness is 80nm; evaporating RH:RD=98:2 (mass ratio) on the hole transport layer as a light emitting layer, wherein the evaporating thickness is 40nm; evaporating ET-1 and Liq (doping mass ratio is 1:1) on the light-emitting layer as an electron transport layer, wherein the evaporating thickness is 35nm; evaporating LiF as an electron injection layer on the electron transport layer, wherein the evaporating thickness is 0.8nm; vapor deposition of Mg on the electron injection layer: ag=1:9 (doping mass ratio 1:1) as a cathode, evaporation thickness was 13nm, and then compound 34 as a cap layer was evaporated on the cathode, evaporation thickness was 80nm, thereby preparing an organic electroluminescent device.
Device examples 2 to 40
An organic electroluminescent device was produced by the same production method as in device example 1, except that compound 48, compound 96, compound 123, compound 138, compound 186, compound 216, compound 237, compound 265, compound 288, compound 323, compound 340, compound 412, compound 413, compound 452, compound 476, compound 482, compound 489, compound 502, compound 512, compound 522, compound 544, compound 556, compound 562, compound 564, compound 574, compound 580, compound 582, compound 592, compound 602, compound 611, compound 618, compound 664, compound 684, compound 702, compound 730, compound 736, compound 753, compound 775 or compound 790 according to the invention were used as the capping material instead of compound 34 in device example 1, respectively.
Comparative device examples 1 to 5
An organic electroluminescent device was manufactured by the same manufacturing method as device example 1, except that compound 34 in device example 1 was replaced with comparative compound 1, comparative compound 2, comparative compound 3, comparative compound 4 or comparative compound 5, 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 40 of the inventive devices, and comparative examples 1 to 5 gave the following results of testing the light emission characteristics of the organic electroluminescent devices.
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From the data in table 1, it can be seen that the triarylamine derivative shown in formula I of the present invention can be used as a coating material in an organic electroluminescent device, thereby effectively improving the luminous efficiency of the device and prolonging the service life.
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, the Y is selected from O, S, C (R) 2 Any one of N (R);
r is the same or different from each other and is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl, or R can be directly combined with L 0 Bonding;
the z are the same or different from each other and are selected from CH or N atoms, and when z is bonded with other groups, the z is selected from C atoms;
the R is z Are identical or different from each other and are selected from F, CF 3 、{Si(R 1 ) 3 }；
The R is 1 Are identical or different from each other and are selected from substituted or unsubstituted C1-C12 alkyl groups;
wherein n is selected from 1, 2, 3, 4 or 5, when two or more R's are present z When two or more R' s z Identical or different from each other, when R z When selected from F, n is selected from 5;
the Ar is as follows 2 Selected from any one of the groups shown below,
the x are identical or different from each other and are selected from CH or N atoms, and when x is bonded with other groups, the x is selected from C atoms;
the t is 1 Selected from O, S, N (R) 4 )、C(R 5 ) 2 Any one of the above, t 2 Any one selected from CH and N atoms;
the R is 4 、R 5 Are identical or different from each other and are selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R 4 、R 5 Can be directly connected with L 2 Bonding;
the Rx and Ry are the same or different from each other and are selected from any one of hydrogen, deuterium, 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 and substituted or unsubstituted C2-C30 heteroaryl, or Rx and Ry can be mutually connected to form a substituted or unsubstituted ring, or Rx and Ry can be directly connected with L 2 Bonding;
the R is 2 、R 3 Are the same or different from each other, and are selected from any one of hydrogen, deuterium, trifluoromethyl, fluorine, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the m is 1 Selected from 0, 1, 2, 3, 4 or 5, said m 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said m 3 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said m 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said m 5 Selected from 0, 1 or 2, said m 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said m 7 Selected from 0, 1, 2, 3 or 4, when two or more R's are present 2 When two or more R' s 2 Identical or different from each other, or adjacent two R' s 2 May be linked to each other to form a substituted or unsubstituted ring;
the Ar is as follows 1 Any one of 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;
the L is 0 Selected from one or more R c Substituted or unsubstituted: any one of C6-C30 arylene, C2-C30 heteroarylene, divalent C6-C30 aromatic ring and C3-C30 aliphatic ring condensed ring group;
the R is c Are the same or different from each other, and are selected from any one of trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the L is 1 、L 2 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 R is a 、R b Identical to or different from each other, any one selected from hydrogen, deuterium, trifluoromethyl, fluorine, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 alkylsilyl, 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 group;
said n 1 Selected from 0, 1 or 2, when two or more R's are present a When two or more R' s a The same or different from each other;
said n 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 Can be linked to each other to form a substituted or unsubstituted: an aromatic or heteroaromatic ring.
2. A triarylamine derivative as set forth in claim 1 wherein saidAny one selected from the following groups;
said Y is selected from O, S, C (R) 2 Any one of N (R);
the R are identical or different from each other and are selected from any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl and C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzothienyl, benzofuranyl, benzocyclopentyl or benzocyclohexenyl, or R may be directly linked to L 0 Bonding;
the a 1 Selected from 0, 1 or 2, said a 2 Selected from 0, 1, 2, 3 or 4, said a 3 Selected from 0, 1, 2 or 3, said a 4 Selected from 0 or 1.
3. A triarylamine derivative as set forth in claim 1 wherein saidAny one selected from the following groups;
said Y is selected from O, S, C (R) 2 Any one of N (R);
the R are identical or different from each other and are selected from any one of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl and C1-C12 alkyl groups: methyl, ethyl and propylA group, isopropyl, tert-butyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzothienyl, benzofuranyl, benzocyclopentyl, or benzocyclohexenyl group, or R may be directly associated with L 0 Bonding;
the R is a 、R b Identical to or different from each other, selected from hydrogen, deuterium, trifluoromethyl, fluorine or any one of the following groups substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine, C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzothienyl, benzofuranyl, benzocyclopentyl or benzocyclohexenyl;
Said b 1 Selected from 0, 1 or 2, said b 2 Selected from 0, 1, 2, 3 or 4, said b 3 Selected from 0 or 1, said b 4 Selected from 0, 1, 2, 3, 4, 5 or 6, said b 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said b 6 Selected from 0, 1, 2, 3, 4 or 5, said b 7 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said b 8 Selected from 0, 1, 2 or 3.
4. A triarylamine derivative according to claim 1, wherein said Ar 1 - (Rz) n is selected from any one of the groups shown below;
the R is 6 Are identical or different from each other and are selected from hydrogen, deuterium, trifluoromethyl, fluorine, or any one of the following groups substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine, C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl;
the c 1 Selected from 0, 1, 2, 3 or 4, said c 2 Selected from 0, 1, 2 or 3, said c 3 Selected from 0, 1 or 2, said c 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said c 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, said c 6 Selected from 0, 1, 2, 3, 4 or 5, said c 7 Selected from 0 or 1, said c 8 Selected from 0, 1, 2, 3, 4, 5 or 6, when two or more R's are present 6 When two or more R' s 6 Identical or different from each other, or adjacent two R 6 May be linked to each other to form a substituted or unsubstituted ring;
the q is 1 Selected from 1, 2, 3, 4 or 5, said q 2 Selected from 1, 2, 3 or 4, said q 3 Selected from 1, 2 or 3, said q 4 Selected from 1, 2, 3, 4, 5, 6 or 7, said q 5 Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9, said q 6 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.
5. A triarylamine derivative as set forth in claim 1 wherein Ar is 2 Any one selected from the following groups;
the t is 1 Selected from O, S, N (R) 4 )、C(R 5 ) 2 Any one of the above, t 2 Any one selected from CH and N atoms;
the R is 4 、R 5 Are identical or different from each other, and are selected from any one of the following groups substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine and C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl or naphthyridinyl, or R 4 、R 5 Can be directly connected with L 2 Bonding;
the R is 2 、R 3 Identical to or different from each other, selected from hydrogen, deuterium, trifluoromethyl, fluorine or any one of the following groups substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine, C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, or tri-tert-butylsilyl;
said d 1 Selected from 0, 1, 2, 3, 4 or 5, said d 2 Selected from 0, 1, 2, 3 or 4, said d 3 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, said d 4 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said d 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said d 6 Selected from 0, 1, 2 or 3, said d 7 Selected from 0, 1 or 2, said d 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said d 10 Selected from 0, 1, 2, 3, 4, 5 or 6.
6. A triarylamine derivative as set forth in claim 1 wherein said L 1 、L 2 Are the same or different from each other, and are selected from any one of single bonds or groups shown below;
the R is 7 Are identical or different from each other and are selected from hydrogen, deuterium, trifluoromethyl, fluorine, or any one of the following groups substituted or unsubstituted by one or more deuterium, trifluoromethyl, fluorine, C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl;
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 10Said e 6 Selected from 0, 1, 2, 3, 4 or 5, said e 7 Selected from 0 or 1, said e 8 Selected from 0, 1, 2, 3, 4, 5 or 6.
7. A triarylamine derivative as set forth in claim 1 wherein said L 0 Any one selected from the group consisting of the following groups and combinations thereof;
the v are identical or different from each other and are selected from CH or N atoms, and when v is bonded with other groups, the v is selected from C atoms;
the R is c Are identical or different from each other and are selected from hydrogen, trifluoromethyl, fluorine, or any one of the following groups substituted or unsubstituted by one or more trifluoromethyl, fluorine, C1-C12 alkyl groups: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, or tri-tert-butylsilyl;
said f 1 Selected from 0, 1, 2, 3 or 4, said f 2 Selected from 0, 1 or 2, said f 3 Selected from 0, 1, 2 or 3, said f 4 Selected from 0, 1, 2, 3, 4 or 5, said f 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said f 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, said f 7 Selected from 0 or 1, said f 8 Selected from 0, 1, 2, 3, 4, 5 or 6.
8. A triarylamine derivative as set forth in claim 1 wherein said triarylamine derivative is selected from any one of the structures set forth in the following;
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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.
CN202310573647.2A 2023-05-19 2023-05-19 Triarylamine derivative and organic electroluminescent device thereof Pending CN116554218A (en)

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