CN113620818B - Triarylamine compound containing condensed rings and organic light-emitting device thereof - Google Patents

Triarylamine compound containing condensed rings and organic light-emitting device thereof Download PDF

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CN113620818B
CN113620818B CN202110927003.XA CN202110927003A CN113620818B CN 113620818 B CN113620818 B CN 113620818B CN 202110927003 A CN202110927003 A CN 202110927003A CN 113620818 B CN113620818 B CN 113620818B
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CN113620818A (en
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李梦茹
刘喜庆
陆影
韩春雪
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Changchun Hyperions Technology Co Ltd
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Abstract

The invention provides a triarylamine compound containing condensed rings and an organic light-emitting device thereof, and relates to the technical field of organic photoelectric materials. The triarylamine compound containing condensed rings has excellent hole transmission performance, has the advantages of high luminous efficiency and low driving voltage, is a good hole transmission material, and can improve the luminous efficiency and the service life of an organic light-emitting device and reduce the driving voltage of the device; the triarylamine compound containing condensed rings provided by the invention is applied to an organic light-emitting device as a cover layer material, so that the light extraction efficiency can be improved, the light-emitting efficiency of the organic light-emitting device can be improved, and the service life of the device can be prolonged. The triarylamine organic compound disclosed by the invention is simple to synthesize and easy to operate, and can be widely applied to the fields of panel display, illumination light sources, organic solar cells, organic photoreceptors or organic thin film transistors and the like.

Description

Triarylamine compound containing condensed rings and organic light-emitting device thereof
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to a triarylamine compound containing condensed rings and an organic light-emitting device thereof.
Background
With the advent of the 5G ultra-high speed network communications era, human demand for information has increased explosively, and the demands for randomness and timeliness of information acquisition have become higher and higher. Portable, large-size display technology is a necessary condition to meet this demand. In view of the development of the prior art, an organic light-emitting diode (OLED) using an organic semiconductor as a functional material has the most potential, which is attributed to the advantages of wide viewing angle, fast response speed, energy saving, stable color, strong environmental adaptability, no radiation, light weight, thin thickness, wide adaptable display temperature range, and the like of the OLED technology, and particularly, the OLED can be used for manufacturing devices on flexible substrates, so that large-area display portability is possible.
The organic light emitting device is a self-luminous device using the following principle: by applying an electric field, the fluorescent substance emits light by the recombination energy of holes injected from the anode and electrons injected from the cathode. OLED organic light-emitting materials can be broadly divided into three classes of materials in terms of use: the charge injection and transport materials are divided into electron injection materials, electron transport materials, hole injection materials and hole transport materials, and the luminescent materials can be further divided into main luminescent materials and doping materials.
The organic hole transport layer plays an important role in transferring holes injected from the anode to the light emitting layer, and the hole transport layer material having excellent hole mobility is advantageous for the injection balance of carriers in the device, thereby reducing the driving voltage of the organic light emitting device. On the other hand, in order to prevent excitons generated in the light emitting layer from diffusing into the hole transporting layer, which causes color cast and light emitting efficiency to be lowered, it is also required that the hole transporting layer be capable of blocking the out-diffusion of excitons, preventing efficiency roll-off and improving stability of the device.
However, at present, research on organic light emitting materials has been widely conducted in academia and industry, and a great number of organic light emitting materials having excellent properties have been developed. In general, the direction of the future organic light emitting devices is to develop white light devices and full-color display devices with high efficiency, long lifetime and low cost, but the industrialization progress of the technology still faces a number of key problems. Therefore, the compound is designed and searched to be a stable and efficient compound which is used as a novel material of the organic light-emitting device to overcome the defects of the organic light-emitting device in the practical application process, and is an important point in the research work of the material of the organic light-emitting device and a research and development trend in the future.
Disclosure of Invention
The invention aims to provide a triarylamine compound containing condensed rings and an organic light-emitting device thereof based on the prior art and aiming at industrialization, and the organic light-emitting device prepared by using the triarylamine compound containing condensed rings solves the problem of unmatched electron/hole migration in an organic material layer, thereby remarkably improving the comprehensive performance of the device in the aspects of luminous efficiency, voltage and the like; as the main constituent of the hole transport layer in the organic light-emitting device, the problems are solved, and the molecular structural general formula is shown in formula I:
wherein the group C is selected from one of the following groups:
wherein the R is 2 The same or different are selected from hydrogen, deuterium, phenyl or naphthyl;
the R is 1 One selected from hydrogen, deuterium, halogen atoms, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl;
the c is selected from 0 or 1; the k is selected from 0, 1 or 2; the i is selected from 0, 1, 2 or 3; the j is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said d is selected from 0, 1, 2, 3 or 4; the h is selected from 0, 1, 2, 3, 4 or 5; said e is selected from 0, 1, 2, 3, 4, 5 or 6; said f is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
The group B is selected from one of the following groups:
wherein R is m Are the same or different from each other, and are each independently selected from one of hydrogen, deuterium, a halogen atom, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl;
said m is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; r is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11;
ar is selected from any one of the following groups:
the R is 12 Selected from the group consisting of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, and fused cyclic groups selected from the group consisting of substituted or unsubstituted aromatic and aliphatic rings; the R is 13 Selected from deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl;
Wherein said R is 13 Can also be R 23 Substituted, R 23 One or more selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothienyl, dibenzofuranyl, wherein the two or more substituents are as defined in the specificationIn the case of substitution, a plurality of substituents are the same or different from each other;
a is 0, 1, 2, 3 or 4; b is 1, 2, 3, 4 or 5; p is 0, 1, 2, 3, 4, 5, 6, 7 or 8; q is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
the L is 0 、L 1 、L 2 Independently selected from one of single bond, substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C2-C20 heteroarylene;
wherein "substituted …" in the above "substituted or unsubstituted …" means substituted with one or more substituents independently selected from the group consisting of deuterium, cyano, C1-C15 alkyl, C3-C15 cycloalkyl, C6-C25 aryl, C2-C20 heteroaryl.
The invention also provides an organic light-emitting device, which comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode or outside one or more than one of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the triarylamine compounds containing condensed rings.
The invention has the beneficial effects that:
the invention provides a triarylamine compound containing condensed rings and an organic light-emitting device thereof, wherein the compound takes triarylamine as a center, simultaneously connects a benzo-aliphatic ring and a condensed aryl group, and the aliphatic ring has electron pushing capability relative to aryl, so that the electron donating capability of the compound is further enhanced, the compound has excellent hole transport performance, the condensed aryl increases the molecular weight of the compound, the glass transition temperature of the compound is improved, and the compound has better stability and is a good hole transport material. The compound provided by the invention has higher HOMO energy level, has high injection efficiency of holes, is favorable for carrier transmission, and can effectively improve exciton utilization rate, thereby prolonging the service life of luminous efficiency of an organic light-emitting device and reducing the driving voltage of the device;
The triarylamine compound containing condensed rings provided by the invention is applied to an organic light-emitting device as a cover layer material, can effectively solve the problem of total emission of an interface between an ITO film and a glass substrate and an interface between the glass substrate and air, reduces total reflection loss and waveguide loss in an OLED device, and improves the light extraction efficiency, thereby improving the light-emitting efficiency of the organic light-emitting device. In addition, the triarylamine compound containing condensed rings effectively blocks water and oxygen in the external environment, protects the OLED display panel from being corroded by the water and the oxygen, and can prolong the service life of the device.
Detailed Description
The following description of embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is shown, however, only some, but not all embodiments of the invention are shown. 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 this specification, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example, the number of the cells to be processed, Can indicate->And so on.
The alkyl group according to the present invention is a hydrocarbon group having at least one hydrogen atom in the alkane molecule, and may be a straight chain alkyl group or a branched chain alkyl group, and preferably has 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like; the branched alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, an isomeric group of n-pentyl, an isomeric group of n-hexyl, an isomeric group of n-heptyl, an isomeric group of n-octyl, an isomeric group of n-nonyl, an isomeric group of n-decyl, and the like. The alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group.
Cycloalkyl as used herein refers to a hydrocarbon group having at least one hydrogen atom in the cycloparaffin molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 3 to 6 carbon atoms, and examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, camphene, norbornyl, etc., but are not limited thereto. The cycloalkyl group is preferably a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, or a norbornyl group.
Aryl in the present invention refers to the generic term for monovalent radicals remaining after removal of one hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule, which may be a monocyclic aryl, polycyclic aryl or fused ring aryl, preferably having from 6 to 25 carbon atoms, more preferably from 6 to 20 carbon atoms, particularly preferably from 6 to 14 carbon atoms, and most preferably from 6 to 12 carbon atoms. 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, etc., but is not limited thereto; the condensed ring aryl group refers to an aryl group having two or more aromatic rings in the molecule and condensed by sharing two adjacent carbon atoms with each other, for example, but not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthryl, spirobifluorenyl, and the like. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group (preferably a 2-naphthyl group), an anthryl group (preferably a 2-anthryl group), a phenanthryl group, a pyrenyl group, a perylenyl group, a fluorenyl group, a benzofluorenyl group, a triphenylenyl group, or a spirobifluorenyl group.
Heteroaryl according to the present invention refers to the generic term for groups in which one or more aromatic nucleus carbon atoms in the aryl group are replaced by heteroatoms, including but not limited to oxygen, sulfur, nitrogen or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, most preferably 3 to 12 carbon atoms, the attachment site of the heteroaryl group may be located on a ring-forming carbon atom, or on a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl, polycyclic heteroaryl or fused ring heteroaryl. The monocyclic heteroaryl group includes, but is not limited to, pyridyl, pyrimidinyl, triazinyl, furyl, thienyl, pyrrolyl, imidazolyl, and the like; the polycyclic heteroaryl group includes bipyridyl, bipyrimidinyl, phenylpyridyl, etc., but is not limited thereto; the fused ring heteroaryl group includes, but is not limited to, quinolinyl, isoquinolinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiazinyl, and the like. The heteroaryl group is preferably a pyridyl group, a pyrimidyl group, a thienyl group, a furyl group, a benzothienyl group, a benzofuryl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuryl group, a dibenzothienyl group, a benzodibenzothienyl group, a benzodibenzofuryl group, a carbazolyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group, or a phenoxathiazide group.
The alkenyl refers to a monovalent group obtained by removing one hydrogen atom from an olefin molecule, and the alkenyl comprises mono alkenyl, di alkenyl, multi alkenyl and the like. Preferably from 2 to 60 carbon atoms, more preferably from 2 to 30 carbon atoms, particularly preferably from 2 to 15 carbon atoms, most preferably from 2 to 6 carbon atoms. Examples of the alkenyl group include vinyl, butadienyl, and the like, but are not limited thereto. The alkenyl group is preferably a vinyl group.
The arylene group according to the present invention means a generic term for divalent groups remaining after removal of two hydrogen atoms from the aromatic nucleus carbon of an aromatic compound molecule, which may be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic arylene group includes phenylene and the like, but is not limited thereto; the polycyclic arylene group includes biphenylene, terphenylene, etc., but is not limited thereto; the condensed ring arylene includes, but is not limited to, naphthylene, anthrylene, phenanthrylene, fluorenylene, pyreylene, triphenylene, fluoranthenylene, phenylenedenyl, and the like. The arylene group is preferably phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, or phenylenediyl.
Heteroaryl, as used herein, refers to the generic term for groups in which one or more of the aromatic nucleus carbons in the arylene group is replaced with a heteroatom, including but not limited to oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms, the heteroarylene group may be attached at a ring-forming carbon atom or at a ring-forming nitrogen atom, and the heteroarylene group may be a monocyclic heteroarylene group, a polycyclic heteroarylene group, or a fused ring heteroarylene group. The monocyclic heteroarylene group includes, but is not limited to, a pyridylene group, a pyrimidinylene group, a triazinylene group, a furanylene group, a thienyl group, and the like; the polycyclic heteroarylene group includes bipyridylene group, bipyrimidiylene group, phenylpyridylene group, etc., but is not limited thereto; the condensed ring heteroarylene group includes quinolinylene, isoquinolylene, indolylene, benzothienyl, benzofuranylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, dibenzofuranylene, benzodibenzofuranylene, dibenzothiophenylene, benzodithiorenylene, carbazolylene, benzocarbazolylene, acridinylene, 9, 10-dihydroacridinylene, phenoxazinylene, phenothiazinylene, phenoxazinylene, and the like, but is not limited thereto. The heteroaryl group is preferably a pyridyl group, a pyrimidylene group, a thienyl group, a furanylene group, a benzothienyl group, a benzofuranylene group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzodibenzothiophenyl group, a benzodibenzofuranyl group, a carbazolyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group, or a phenoxathiazide group.
The term "substituted …" as used herein, such as substituted alkyl, substituted cycloalkyl, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene, etc., means substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted, independently selected from deuterium, halogen, cyano, substituted or unsubstitutedOr unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, substituted or unsubstituted amino, etc., but is not limited thereto, is preferably mono-or polysubstituted with a group selected from deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclohexyl, adamantyl, norbornyl, phenyl, tolyl, mesityl, pentadeuterophenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, benzophenanthryl, pyrenyl, benzyl, triphenylyl,Mono-or polysubstituted with groups of the group, perylene, fluoranthryl, fluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirobifluorenyl, diphenylamino, dimethylamino, carbazolyl, 9-phenylcarbazolyl, carbazoloindolyl, pyrrolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzimidazolyl, indolyl, quinolinyl, isoquinolinyl, phenothiazinyl, phenoxazinyl, acridinyl.
Aliphatic as used herein refers to aliphatic hydrocarbons having from 1 to 60 carbon atoms, which may be fully unsaturated or partially unsaturated.
The alicyclic ring of the present invention means a cyclic hydrocarbon having aliphatic nature, and the molecule contains a closed carbocycle, which may be a single-or multi-cyclic hydrocarbon of 3 to 18 carbon atoms, preferably 3 to 12 carbon atoms, more preferably 3 to 7 carbon atoms, and may be completely unsaturated or partially unsaturated, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but is not limited thereto. 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 term "ring" as used herein, unless otherwise specified, refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or a heterocyclic ring having 2 to 60 carbon atoms or a combination thereof, which comprises a saturated or unsaturated ring.
The term "bonded to form a cyclic structure" as used herein means that two groups are attached to each other by a chemical bond and optionally aromatized. As exemplified below:
In the present invention, the ring formed by the connection may be a five-membered ring or a six-membered ring or a condensed ring, such as benzene, naphthalene, fluorene, cyclopentene, cyclopentane, cyclohexane acene, quinoline, isoquinoline, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.
The invention provides a triarylamine compound containing condensed rings, which has a molecular structural general formula shown in formula I:
wherein the group C is selected from one of the following groups:
wherein the R is 2 The same or different are selected from hydrogen, deuterium, phenyl or naphthyl;
the R is 1 One selected from hydrogen, deuterium, halogen atoms, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl;
the c is selected from 0 or 1; the k is selected from 0, 1 or 2; the i is selected from 0, 1, 2 or 3; the j is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said d is selected from 0, 1, 2, 3 or 4; the h is selected from 0, 1, 2, 3, 4 or 5; said e is selected from 0, 1, 2, 3, 4, 5 or 6; said f is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
The group B is selected from one of the following groups:
wherein R is m Are the same or different from each other, and are each independently selected from one of hydrogen, deuterium, a halogen atom, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl;
said m is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; r is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11;
ar is selected from any one of the following groups:
the R is 12 Selected from the group consisting of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, and fused cyclic groups selected from the group consisting of substituted or unsubstituted aromatic and aliphatic rings; the R is 13 Selected from deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl;
Wherein said R is 13 Can also be R 23 Substituted, R 23 Selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, t-butyl, cyclohexyl, and cycloOne or more of pentyl, adamantyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothienyl, dibenzofuranyl, where substituted with multiple substituents, the multiple substituents may be the same or different from each other;
a is 0, 1, 2, 3 or 4; b is 1, 2, 3, 4 or 5; p is 0, 1, 2, 3, 4, 5, 6, 7 or 8; q is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
the L is 0 、L 1 、L 2 Independently selected from one of single bond, substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C2-C20 heteroarylene;
wherein "substituted …" in the above "substituted or unsubstituted …" means substituted with one or more substituents independently selected from the group consisting of deuterium, cyano, C1-C15 alkyl, C3-C15 cycloalkyl, C6-C25 aryl, and C2-C20 heteroaryl.
Preferably, said R m Are the same or different from each other, and are each independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornyl, or one of the groups shown below:
preferably, said R m Are the same or different from each other, and are each independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornyl, or one of the groups shown below:
more preferably, the group B is selected from one of the following groups:
preferably, the group C is selected from one of the following groups:
preferably, said R 12 Methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, phenyl, tolyl, biphenyl, naphthyl or one of the following substituents:
preferably, said R 13 One selected from deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, indolyl, benzothienyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, or adjacent R 13 The groups may be joined to form a substituted or unsubstituted aliphatic ring.
Preferably, ar is selected from any one of the following groups:
preferably, the L 0 、L 1 、L 2 Independently selected from one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted phenylene-naphthylene group, wherein the substituent is one or more of deuterium, ethyl, isopropyl, t-butyl, phenyl, pentadeuterated phenyl, and in the case of being substituted with a plurality of substituents, the plurality of substituents are the same or different from each other.
Preferably, the L 0 、L 1 、L 2 Independently selected from a single bond or one of the following groups:
more preferably, the L 0 、L 1 、L 2 Independently selected from a single bond or one of the following groups:
most preferably, the triarylamine compound containing condensed rings is selected from any one of the chemical structures shown in the following formula:
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the preparation method of the triarylamine compound containing condensed rings in the formula I can be prepared through coupling reaction conventional in the field, for example, can be prepared through the following synthetic route, but the invention is not limited to the following steps:
The triarylamine compound containing condensed rings can be obtained by the conventional Buchwald reaction in the field, namely, under the nitrogen atmosphere, an amine compound a and a halogen compound b are subjected to the Buchwald reaction to obtain an intermediate A, then the intermediate A and the halogen compound c are subjected to the Buchwald reaction, and the intermediate A and the halogen compound c are reacted at the corresponding catalyst, organic base, ligand, solution and corresponding temperature to obtain the corresponding compound of the formula I, wherein the halogen compound X 0 、X 1 A compound which is Cl, br or I.
The source of the raw materials used in the above-mentioned various reactions is not particularly limited, and can be obtained using commercially available raw materials or by using a preparation method well known to those skilled in the art. The present invention is not particularly limited to the above reaction, and conventional reactions well known to those skilled in the art may be employed. The compound has few synthesis steps and simple method, and is beneficial to industrial production.
The invention also provides an organic light-emitting device, which comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode or outside one or more than one of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the triarylamine compounds containing condensed rings.
Preferably, the organic layer comprises a hole transport layer, and the hole transport layer contains any one or a combination of at least two of the triarylamine compounds containing condensed rings.
Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, and any one or at least two of the triarylamine compounds containing condensed rings described in the present invention are contained in the first hole transport layer and/or the second hole transport layer.
Preferably, the organic layer comprises a cover layer, and the cover layer contains any one or a combination of at least two of the triarylamine compounds containing condensed rings.
Preferably, the coating layer of the present invention may have a single-layer structure, a two-layer structure or a multi-layer structure, and the coating layer material of the present invention may be at least one member selected from the group consisting of the condensed ring-containing triarylamine-based compounds of the present invention, or may contain conventional coating layer materials well known to those skilled in the art.
Preferably, the organic light emitting device according to the present invention is selected from the following structures, but is not limited thereto:
(1) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/cathode/capping layer;
(2) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/cathode;
(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/hole blocking layer/cathode;
(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode;
(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode;
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode;
(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode;
(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode;
(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode;
(10) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode;
(11) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode;
(12) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode;
(13) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode;
(14) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode;
(15) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;
(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode;
(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;
(18) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode/capping layer;
(19) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode;
(20) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode;
(21) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode;
(22) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode;
(23) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode/capping layer;
(24) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;
(25) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;
(26) Anode/hole injection layer/hole buffer layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;
(27) Anode/hole injection layer/hole buffer layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/cover layer;
(28) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/cathode;
(29) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron injection layer/cathode;
(30) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/cathode/capping layer;
(31) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/cathode;
(32) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron injection layer/cathode;
(33) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/cathode/capping layer;
(34) Anode/hole injection layer/hole transport layer/light emitting layer/cathode/capping layer;
(35) Anode/hole injection layer/hole transport layer/light emitting layer/cathode;
(36) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode;
(37) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer.
However, the structure of the organic light emitting device is not limited thereto. The organic light-emitting device can be selected and combined according to the device parameter requirements and the characteristics of materials, and partial organic layers can be added or omitted. For example, an electron buffer layer may be further added between the electron transport layer and the electron injection layer; the organic layer having the same function may be formed into a stacked structure of two or more layers, and for example, the electron transport layer may further include a first electron transport layer and a second electron transport layer.
The light emitting device of the present invention is generally formed on a substrate. The substrate may be a substrate made of glass, plastic, polymer film, silicon, or the like, as long as it is not changed when an electrode is formed or an organic layer is formed. When the substrate is opaque, the electrode opposite thereto is preferably transparent or translucent.
At least one of the anode and the cathode of the light-emitting device of the present invention is transparent or translucent, and preferably, the light-emitting device of the present invention is transparent or translucent on the cathode side.
The anode material is generally preferably a material having a large work function so that holes are smoothly injected into the organic material layer, and a conductive metal oxide film, a semitransparent metal thin film, or the like is often used. For example, a film (NESA or the like) made of a conductive inorganic compound such as indium oxide, zinc oxide, tin oxide, indium tin oxide (abbreviated as ITO) or indium zinc oxide (abbreviated as IZO) as a composite thereof, or gold, platinum, silver, copper or the like is used, and examples of the production method include vacuum vapor deposition, sputtering, ion plating, and the like. As the anode, an organic transparent conductive film such as polyaniline or a derivative thereof, polythiophene or a derivative thereof, or the like can be used. The anode may have a laminate structure of 2 or more layers, and preferably, a transparent ITO substrate is used for the anode of the present invention.
The hole injection layer is to improve efficiency of injecting holes from the anode into the hole transport layer and the light emitting layer. The hole injection material of the present invention may be a metal oxide such as molybdenum oxide, silver oxide, vanadium oxide, tungsten oxide, ruthenium oxide, nickel oxide, copper oxide, or titanium oxide, a low molecular organic compound such as a phthalocyanine compound or a polycyano-containing conjugated organic material, but is not limited thereto. Preferably, the hole injection layer of the present invention is selected from 4,4',4″ -tris [ 2-naphthylphenylamino ] triphenylamine (abbreviated as 2T-NATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazabenzophenanthrene (abbreviated as HAT-CN), 4',4″ -tris (N, N-diphenylamino) triphenylamine (abbreviated as TDATA), 4',4″ -tris [ N- (3-methylphenyl) -N-phenylamino ] triphenylamine (abbreviated as MTDATA), copper (II) phthalocyanine (abbreviated as CuPc), N' -bis [4- [ bis (3-methylphenyl) amino ] phenyl ] -N, N '-diphenyl-biphenyl-4, 4' -diamine (abbreviated as DNTPD), etc., which may be a single structure composed of a single substance, or a single layer or a multi-layer structure formed of different substances, and the above materials may include other known materials suitable for the hole injection layer.
The hole transport layer is a layer having a function of transporting holes, and the hole transport layer may include a first hole transport layer material and a second hole transport layer material. The hole transport material of the present invention is preferably a material having a good hole transport property, and may be selected from polymer materials such as aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, butadiene compounds, and the like, and poly-p-phenylene derivatives, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polyvinylcarbazole and derivatives thereof, polysilane and derivatives thereof, but not limited thereto. Preferably, the hole transport layer of the present invention is selected from N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (abbreviated as NPB), N '-bis (naphthalen-1-yl) -N, N' -di (phenyl) -2,2 '-dimethylbenzidine (abbreviated as α -NPD), N' -diphenyl-N, N '-bis (3-methylphenyl) -1,1' -biphenyl-4, 4 '-diamine (abbreviated as TPD), 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (abbreviated as TAPC), 2, 7-tetra (diphenylamino) -9, 9-spirobifluorene (abbreviated as Spiro-TAD), etc., which may be a single structure composed of a single substance, or a single layer structure or a multi-layer structure composed of different substances, and may include other known materials suitable for the hole transport layer in addition to the above materials and combinations thereof. More preferably, the hole transport layer is any one or a combination of at least two of the triarylamine compounds containing condensed rings. .
The electron blocking layer is a layer that will transport holes and block electrons, and preferably, the electron blocking layer of the present invention may be selected from N, N ' -bis (naphthalen-1-yl) -N, N ' -bis (phenyl) -2,2' -dimethylbenzidine (abbreviated as α -NPD), 4',4″ -tris (N, N-diphenylamino) -triphenylamine (abbreviated as TDATA), N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (abbreviated as TPD), 4' -cyclohexanedio [ N, N-bis (4-methylphenyl) aniline ] (abbreviated as TAPC), 2, 7-tetrakis (diphenylamino) -9, 9-spirobifluorene (abbreviated as Spiro-TAD), etc., which may be a single structure composed of a single substance, or a single-layer structure formed of different substances, and a combination thereof, and the electron blocking layer material may include other known materials suitable for the electron blocking layer.
The light-emitting layer is a layer having a light-emitting function. As for the light emitting layer of the organic light emitting device of the present invention, a red light emitting material, a green light emitting material, or a blue light emitting material may be used as the light emitting material, and two or more light emitting materials may be mixed and used as necessary. The light-emitting material may be a host material alone or a mixture of a host material and a dopant material, and the light-emitting layer is preferably a mixture of a host material and a dopant material.
Preferably, the host material according to the invention is selected from the group consisting of 4,4 '-bis (9-Carbazolyl) Biphenyl (CBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), 4-bis (9-carbazolyl) biphenyl (CPB), 9' - (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -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 luminescent layer host material may also include other known materials suitable for use as a luminescent layer, such as the red luminescent layer host material represented below:
the light emitting layer guest material of the present invention may include one material or a mixture of two or more materials, and the light emitting material is classified into a blue light emitting material, a green light emitting material, and a red light emitting material. The blue light emitting layer object is selected from (6- (4- (diphenylamino (phenyl) -N, N-diphenylpyrene-1-amine) (DPAP-DPPA for short), 2,5,8, 11-tetra-tert-butylperylene (TBPe for short), 4' -di [4- (diphenylamino) styryl)]Biphenyl (BDAVBi for short), 4' -di [4- (di-p-tolylamino) styryl]Diphenyl (abbreviated as DPAVBi) and di (2-hydroxyphenylpyridine) beryllium (abbreviated as Bepp) 2 )、Bis (4, 6-difluorophenylpyridine-C2, N) picolinated iridium (FIrpic) and the like, the emissive layer guest material may include other known materials suitable for use as an emissive layer in addition to the above materials and combinations thereof. The green light-emitting layer object is selected from tris (2-phenylpyridine) iridium (Ir (ppy) 3 ) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy) 2 (acac)) and the like, the light-emitting layer guest material may include other known materials suitable for use as a light-emitting layer in addition to the above materials and combinations thereof. The red light-emitting layer guest may be selected from 9, 10-bis [ N- (p-tolyl) anilino group]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), tris [ 1-phenylisoquinoline-C2, N]Iridium (III) (Ir (piq) 3 ) Ir (piq) iridium bis (1-phenylisoquinoline) (acetylacetonate) 2 (acac)) and the like, the red light-emitting layer guest material may include other known materials suitable as a light-emitting layer, for example, one of the red light-emitting layer guest materials represented as follows, in addition to the above materials:
the doping ratio of the host material and the guest material of the light-emitting layer may be varied depending on the materials used, and the doping ratio of the guest material of the light-emitting layer is usually 0.01 to 20%, preferably 0.1 to 15%, more preferably 1 to 10%.
The hole blocking layer is a layer for transporting electrons and blocking holes, and preferably, the hole blocking layer is selected from 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (abbreviated as BCP), 1,3, 5-tri (N-phenyl-2-benzimidazole) benzene (abbreviated as TPBi) and tris (8-hydroxyquinoline) aluminum (III) (abbreviated as Alq) 3 ) 8-hydroxyquinoline-lithium (Liq), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq) and 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ) can be a single structure formed by a single substance or a single-layer structure or a multi-layer structure formed by different substances. In addition to the above materials, hole blocking layer materialsOther known materials suitable for use as hole blocking layers may also be included.
The electron transport layer is a layer having a function of transporting electrons, and plays a role of injecting electrons and balancing carriers, and the electron transport layer may include a first electron transport layer material and a second electron transport layer material. The electron transport material of the present invention may be selected from known metal complexes of oxadiazole derivatives, anthraquinone dimethanes and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinone dimethanes and derivatives thereof, fluorenone derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, and may have a single structure formed of a single substance, or may have a single structure or a multilayer structure formed of different substances. In addition to the above materials, the electron transport layer material may include other known materials suitable for use as an electron transport layer.
The electron injection layer material is a material that assists electron injection from the cathode into the organic layer. The best choice for this material is typically corrosion resistant, high work function metals as cathodes, with commonly used materials being Al and Ag. Electron injecting materials have evolved to date to include two classes; one is an alkali metal compound, such as lithium oxide (Li 2 O), lithium boron oxide (LiBO) 2 ) Cesium carbonate (Cs) 2 CO 3 ) Potassium silicate (K) 2 SiO 3 ) And the like, the optimal thickness is generally 0.3-1.0 nm, and the device formed by the compound can reduce the driving voltage and improve the device efficiency. In addition, an acetate Compound (CH) 3 COOM, where M is Li, na, K, rb, cs) also has a similar effect. The other is alkali metal fluoride (MF, where M is Li, na, K, rb, cs), and if Al is used as the cathode material, these materials are typically less than 1.0nm thick at best. Preferably, the electron injection layer according to the present invention may be selected from LiF.
A cathode material is generally preferably a metal material having a small work function in order to inject electrons into the electron injection/transport layer or the light-emitting layer. For example, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, or an alloy of 2 or more of them, or an alloy of 1 or more of them with 1 or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin, graphite, or a graphite interlayer compound, etc. can be used. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy. The cathode may have a laminate structure of 2 or more layers. The cathode may be prepared by forming a thin film of these electrode materials by vapor deposition, sputtering, or the like. Among them, when light emission of the light emitting layer is taken out from the cathode, the light transmittance of the cathode is preferably more than 10%. The sheet resistivity of the cathode is preferably hundreds Ω/≡or less, and the film thickness is usually 10nm to 1 μm, preferably 50 to 200nm.
The cladding material is to reduce total emission loss and waveguide loss in the OLED device and to improve light extraction efficiency. Alq can be used as the coating material of the present invention 3 TPBi or any one or a combination of at least two of the triarylamine compounds containing condensed rings.
The method for preparing and forming each layer in the organic light emitting device is not particularly limited, and any one of vacuum evaporation method, spin coating method, vapor deposition method, blade coating method, laser thermal transfer method, electrospray coating method, slit coating method, and dip coating method may be used, and in the present invention, a vacuum evaporation method is preferably used.
The organic light-emitting 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 source of the raw materials used in the following examples is not particularly limited and may be commercially available products or prepared by a preparation method well known to those skilled in the art.
The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;
the elemental analysis was carried out using a Vario EL cube organic elemental analyzer from Elementar, germany, and the sample mass was 5 to 10mg.
EXAMPLE 1 Synthesis of Compound 4
Synthetic intermediate A-1
To a 1L reaction flask were successively added toluene (600 mL), a-1 (10.60 g,72 mmol), b-1 (28.61 g,72 mmol), palladium acetate (0.24 g,1.08 mmol), sodium t-butoxide (13.45 g,140 mmol), and tri-t-butylphosphine (8 mL of toluene solution) under nitrogen. And reacted under reflux for 2 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallized from methanol, suction filtered and rinsed with methanol to give intermediate a-1 (20.71 g, 77% yield) as a recrystallized solid, which was > 99.7% pure by HPLC.
Synthesis of Compound 4
Toluene solvent (500 mL), c-1 (10.92 g,40 mmol), intermediate A-1 (14.93 g,40 mmol), pd were added sequentially to a 1L reaction flask under nitrogen 2 (dba) 3 (0.37 g,0.40 mmol), BINAP (0.75 g,1.20 mmol) and sodium tert-butoxide (7.69 g,80 mmol) were dissolved by stirring, and the reaction was refluxed under the protection of nitrogen for 24 hours, after the reaction was completed, methylene chloride and distilled water were added to the reaction solution, stirred, and then the solution was extracted by liquid separation. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed, and the organic layer was purified with cyclohexane: ethyl acetate=10:1 was purified by column chromatography as an eluent to obtain compound 4 (16.75 g, yield 74%) and purity of the solid by HPLC > 99.4%. Mass spectrum m/z:565.2756 (theory: 565.2770). Management deviceTheoretical element content (%) C 43 H 35 N: c,91.29; h,6.24; n,2.48. Measured element content (%): c,91.36; h,6.20; n,2.42.
EXAMPLE 2 Synthesis of Compound 9
Using the same method as in Synthesis example 1, substituting c-1 with equimolar c-9, compound 9 (20.14 g) was synthesized, and the purity of the solid was ≡ 99.7% by HPLC. Mass spectrum m/z:689.3092 (theory: 689.3083). Theoretical element content (%) C 53 H 39 N: c,92.27; h,5.70; n,2.03. Measured element content (%): c,92.20; h,5.65; n,2.09.
EXAMPLE 3 Synthesis of Compound 21
Using the same method as in Synthesis example 1, substituting c-1 with equimolar c-21, compound 21 (23.40 g) was synthesized, and the purity of the solid was ≡ 99.6% by HPLC. Mass spectrum m/z:799.4195 (theory: 799.4178). Theoretical element content (%) C 61 H 53 N: c,91.57; h,6.68; n,1.75. Measured element content (%): c,91.50; h,6.73; n,1.78.
EXAMPLE 4 Synthesis of Compound 31
Using the same method as in Synthesis example 1, substituting c-1 with equimolar c-31, compound 31 (16.71 g) was synthesized, and the purity of the solid was ≡ 99.5% by HPLC. Mass spectrum m/z:605.3072 (theory: 605.3083). Theoretical element content (%) C 46 H 39 N: c,91.20; h,6.49; n,2.31. Measured element content (%): c,91.27; h,6.43; n,2.31.
EXAMPLE 5 Synthesis of Compound 33
Using the same method as in Synthesis example 1, substituting c-1 with equimolar c-33, compound 33 (21.11 g) was synthesized, and the purity of the solid was ≡ 99.5% by HPLC. Mass spectrum m/z:703.2863 (theory: 703.2875). Theoretical element content (%) C 53 H 37 NO: c,90.44; h,5.30; n,1.99. Measured element content (%): c,90.38; h,5.35; n,1.97.
EXAMPLE 6 Synthesis of Compound 65
Synthetic intermediate a-2
Under the protection of nitrogen, the compounds E-1 (13.73 g,78 mmol), F-1 (13.42 g,78 mmol) and K are added into a three-necked flask in sequence 2 CO 3 (21.55g,156mmol)、Pd(PPh 3 ) 4 (1.79 g,1.56 mmol) and 600mL of toluene/ethanol/water (3:1:1) mixed solvent were added, the mixture was stirred, and the above-mentioned reactant system was heated under reflux for 8 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature, extracted with deionized water and toluene to give an organic layer, which was washed 3 times with 400mL of deionized water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from toluene to give intermediate a-2 (13.24 g, yield 76%). Mass spectrum m/z:223.1349 (theory: 223.1361).
Using the same method as in Synthesis example 1, compound 65 (24.77 g) was synthesized with a purity of > 99.5% by HPLC, substituting a-1 with equimolar a-2, substituting b-1 with equimolar b-2, substituting c-1 with equimolar c-65. Mass spectrum m/z:793.3725 (theory: 793.3709). Theoretical element content (%) C 61 H 47 N: c,92.27; h,5.97; n,1.76. Measured element content (%): c,92.33; h,5.92; n,1.78.
EXAMPLE 7 Synthesis of Compound 138
Using the same method as in Synthesis example 1, substituting c-1 with equimolar c-138, compound 138 (17.27 g) was synthesized, and the purity of the solid was ≡ 99.6% by HPLC. Mass spectrum m/z:539.2263 (theory: 539.2249). Theoretical element content (%) C 40 H 29 NO: c,89.02; h,5.42; n,2.60. Measured element content (%): c,89.07; h,5.38; n,2.55.
EXAMPLE 8 Synthesis of Compound 152
Using the same method as in Synthesis example 1, substituting c-1 with equimolar c-152, synthesis of Compound 152 (16.97 g), the purity of the solid was ≡ 99.3% by HPLC. Mass spectrum m/z:614.2736 (theory: 614.2722). Theoretical element content (%) C 46 H 34 N 2 : c,89.87; h,5.57; n,4.56. Measured element content (%): : c,89.82; h,5.53; n,4.54.
EXAMPLE 9 Synthesis of Compound 161
Using the same method as in Synthesis example 1, substituting c-1 with equimolar c-161, synthesis of Compound 161 (19.58 g), the purity of the solid was ≡ 99.9% by HPLC. Mass spectrum m/z:589.2419 (theory: 589.2406). Theoretical element content (%) C 44 H 31 NO: c,89.61; h,5.30; n,2.38. Measured element content (%): c,89.65; h,5.32; n,2.32.
EXAMPLE 10 Synthesis of Compound 186
The same procedure as in Synthesis example 1 was used with equimolar amountsC-186 of (a) instead of c-1, compound 186 (19.46 g) was synthesized with a purity of > 99.4% as measured by HPLC. Mass spectrum m/z:615.2917 (theory: 615.2926). Theoretical element content (%) C 47 H 37 N: c,91.67; h,6.06; n,2.27. Measured element content (%): : c,91.73; h,6.02; n,2.24.
EXAMPLE 11 Synthesis of Compound 215
Using the same method as in Synthesis example 1, intermediate a-3 was synthesized in the same manner as in a-2 in example 6, substituting a-1 with equimolar a-3 and c-1 with equimolar b-3, and synthesized compound 215 (16.26 g), and the purity of the solid was ≡ 99.8% by HPLC. Mass spectrum m/z:615.2883 (theory: 615.2864). Theoretical element content (%) C 47 H 29 D 4 N: c,91.67; h,6.06; n,2.27. Measured element content (%): : c,91.60; h,6.09; n,2.30.
EXAMPLE 12 Synthesis of Compound 226
To a 1L reaction flask were successively added toluene (600 mL), a-1 (5.30 g,36 mmol), b-4 (27.60 g,72 mmol), palladium acetate (0.31 g,1.4 mmol), sodium t-butoxide (13.45 g,140 mmol) and tri-t-butylphosphine (8 mL of toluene solution) under nitrogen. And reacted under reflux for 3 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallized from methanol, suction filtered and rinsed with methanol to give recrystallized solid, compound 226 (19.76 g, 73% yield) was synthesized, and the purity of the solid was ≡ 99.4% by HPLC. Mass spectrum m/z:751.3252 (theory: 751.3239). Theoretical element content (%) C 58 H 41 N: c,92.64; h,5.50; n,1.86. Measured element content (%): c,92.70; h,5.44; n,1.87.
EXAMPLE 13 Synthesis of Compound 240
Using the same method as in Synthesis example 1, compound 240 (21.81 g) was synthesized with equal moles of a-4 for a-1, equal moles of b-4 for b-1, equal moles of c-240 for c-1, and HPLC detection of solid purity ≡ 99.8%. Mass spectrum m/z:767.3502 (theory: 767.3490). Theoretical element content (%) C 59 H 37 D 4 N: c,92.27; h,5.91; n,1.82. Measured element content (%): c,92.33; h,5.88; n,1.80.
EXAMPLE 14 Synthesis of Compound 255
Using the same procedure as in Synthesis example 1, intermediate a-5 was synthesized in the same manner as in a-2 in example 6, substituting a-1 with equimolar a-5 and c-1 with equimolar c-255, and synthesizing compound 255 (24.37 g), the purity of the solid was ≡ 99.5% by HPLC. Mass spectrum m/z:827.3543 (theory: 827.3552). Theoretical element content (%) C 63 H 51 N: c,92.83; h,5.48; n,1.69. Measured element content (%): c,92.87; h,5.43; n,1.70.
EXAMPLE 15 Synthesis of Compound 262
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-6 and substituting c-1 with equimolar c-262, synthesized compound 262 (20.90 g) was found to have a solid purity of ≡ 99.8%. Mass spectrum m/z:669.3044 (theory: 669.3032). Theoretical element content (%) C 50 H 39 NO: c,89.65; h,5.87; n,2.09. Measured element content (%): c,89.60; h,5.83; n,2.02.
EXAMPLE 16 Synthesis of Compound 299
Using the same method as in Synthesis example 1, c-1 was replaced with equimolar c-299 to synthesize compound 299 (21.83 g), and the purity of the solid was ≡ 99.6% by HPLC. Mass spectrum m/z:699.3688 (theory: 699.3679). Theoretical element content (%) C 53 H 25 D 12 N: c,90.95; h,7.05; n,2.00. Measured element content (%): : c,90.91; h,7.11; n,1.98.
EXAMPLE 17 Synthesis of Compound 331
Using the same method as in Synthesis example 1, b-1 was replaced with equimolar b-3, c-1 was replaced with equimolar c-331, and Compound 331 (17.42 g) was synthesized, and the purity of the solid was ≡ 99.4% by HPLC. Mass spectrum m/z:649.3537 (theory: 649.3554). Theoretical element content (%) C 49 H 27 D 10 N: c,90.56; h,7.29; n,2.16. Measured element content (%): c,90.50; h,7.34; n,2.18.
EXAMPLE 18 Synthesis of Compound 350
Using the same method as in Synthesis example 1, compound 350 (21.19 g) was synthesized with equal molar substitution of a-7 for a-1, equal molar substitution of b-5 for b-1, equal molar substitution of c-350 for c-1, and a solid purity of ≡ 99.7% by HPLC. Mass spectrum m/z:687.2908 (theory: 687.2926). Theoretical element content (%) C 53 H 37 N: c,92.54; h,5.42; n,2.04. Measured element content (%): c,92.58; h,5.37; n,2.05.
EXAMPLE 19 Synthesis of Compound 368
Using the same method as in Synthesis example 1, b-1 was replaced with equimolar b-5, c-1 was replaced with equimolar c-368, and compound 368 (20.46 g) was synthesized, and the purity of the solid was ≡ 99.3% by HPLC. Mass spectrum m/z:681.3024 (theory: 681.3032). Theoretical element content (%) C 51 H 39 NO: c,89.83; h,5.77; n,2.05. Measured element content (%): c,89.88; h,5.73; n,2.02.
EXAMPLE 20 Synthesis of Compound 388
Using the same method as in Synthesis example 1, compound 388 (22.13 g) was synthesized with a-8 in place of a-1 in equimolar amount, b-5 in place of b-1 in equimolar amount and c-388 in place of c-1 in equimolar amount, and the solid purity was found to be ≡99.4% by HPLC. Mass spectrum m/z:757.3698 (theory: 757.3709). Theoretical element content (%) C 58 H 47 N: c,91.90; h,6.25; n,1.85. Measured element content (%): c,91.97; h,6.20; n,1.82.
EXAMPLE 21 Synthesis of Compound 400
Using the same procedure as in Synthesis example 1, intermediate a-9 was synthesized in the same manner as in a-2 in example 6, substituting a-1 with equimolar a-9, substituting b-1 with equimolar b-5, substituting c-1 with equimolar c-400, and synthesizing Compound 400 (21.52 g), the purity of the solid was ≡ 99.6% by HPLC detection. Mass spectrum m/z:690.3046 (theory: 690.3035). Theoretical element content (%) C 52 H 38 N 2 : c,90.40; h,5.54; n,4.05. Measured element content (%): c,90.46; h,5.50; n,4.03.
EXAMPLE 22 Synthesis of Compound 407
Using the same method as in Synthesis example 1, compound 407 (20.90 g) was synthesized with a-10 replacing a-1, b-5 replacing b-1, c-407 replacing c-1, and an equimolar amount of a-5, and a solid purity of ≡ 99.6% was measured by HPLC. Mass spectrum m/z:741.3406 (theory: 741.3396). Theoretical element content (%) C 57 H 43 N: c,92.27; h,5.84; n,1.89. Measured element content (%): c,92.20; h,5.90; n,1.92.
EXAMPLE 23 Synthesis of Compound 420
Using the same procedure as in Synthesis example 1, intermediate a-11 was synthesized in the same manner as in a-2 in example 6, substituting a-1 with equimolar a-11, substituting b-1 with equimolar b-3, substituting c-1 with equimolar c-240, and synthesizing Compound 420 (20.37 g), the purity of the solid was ∈ 99.7% by HPLC detection. Mass spectrum m/z:697.2791 (theory: 697.2770). Theoretical element content (%) C 54 H 35 N: c,92.94; h,5.06; n,2.01. Measured element content (%): c,92.99; h,5.02; n,2.00.
EXAMPLE 24 Synthesis of Compound 422
Using the same method as in Synthesis example 1, compound 422 (16.92 g) was synthesized with equal molar substitution of a-7 for a-1, equal molar substitution of b-6 for b-1, equal molar substitution of c-422 for c-1, and HPLC detection of solid purity ≡ 99.7%. Mass spectrum m/z:595.3189 (theory: 595.3177). Theoretical element content (%) C 45 H 33 D 4 N: c,90.71; h,6.94; n,2.35. Measured element content (%): c,90.67; h,6.96; n,2.39.
EXAMPLE 25 Synthesis of Compound 436
Using the same method as in Synthesis example 1, the synthesis method of intermediate a-12 was the same as that of a-2 in example 6, substituting a-1 with equimolar a-12, substituting b-1 with equimolar b-7, substituting c-1 with equimolar c-436, synthesizing compound 436 (25.14 g), and detecting by HPLC that the solid purity was ≡ 99.8%. Mass spectrum m/z:872.4163 (theory: 872.4179). Theoretical element content (%) C 67 H 44 D 5 N: c,92.16; h,6.23; n,1.60. Measured element content (%): c,92.11; h,6.20; n,1.58.
EXAMPLE 26 Synthesis of Compound 473
Using the same method as in Synthesis example 1, b-1 was replaced with equimolar b-8, c-1 was replaced with equimolar c-473, and Compound 473 (22.13 g) was synthesized, and the solid purity was ≡ 99.9% by HPLC. Mass spectrum m/z:755.2820 (theory: 755.2803). Theoretical element content (%) C 56 H 39 NS: c,88.74; h,5.19; n,1.85. Measured element content (%): c,88.70; h,5.23; n,1.83.
EXAMPLE 27 Synthesis of Compound 487
Using the same method as in Synthesis example 1, b-1 was replaced with equimolar b-9, c-1 was replaced with equimolar c-487, and Compound 487 (20.84 g) was synthesized, and the purity of the solid was ≡ 99.8% by HPLC. Mass spectrum m/z:713.3097 (theory: 713.3083). Theoretical element content (%) C 55 H 39 N: c,92.53; h,5.51; n,1.96. Measured element content (%): c,92.49; h,5.49; n,2.03.
EXAMPLE 28 Synthesis of Compound 505
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-13 and substituting c-1 with equimolar c-240, compound 505 (24.14 g) was synthesized, and the purity of the solid was ≡ 99.6% by HPLC. Mass spectrum m/z:763.3227 (theory: 763.3239). Theoretical element content (%) C 59 H 41 N: c,92.76; h,5.41; n,1.83. Measured element content (%): c,92.80; h,5.40; n,1.78.
EXAMPLE 29 Synthesis of Compound 517
Using the same method as in Synthesis example 1, c-1 was replaced with equimolar c-517, and compound 517 (23.15 g) was synthesized, and the purity of the solid was ≡ 99.5% by HPLC. Mass spectrum m/z:566.2369 (theory: 566.2358). Theoretical element content (%) C 41 H 30 N 2 O: c,86.90; h,5.34; n,4.94. Measured element content (%): c,86.93; h,5.31; n,4.97.
EXAMPLE 30 Synthesis of Compound 520
Using the same procedure as in Synthesis example 1, intermediate a-14 was synthesized in the same manner as in a-2 in example 6, substituting a-1 with equimolar a-14, substituting b-1 with equimolar b-10, substituting c-1 with equimolar c-517, synthesizing compound 520 (19.47 g), and detecting a solid purity of ∈ 99.7% by HPLC. Mass spectrum m/z:666.2689 (theory: 666.2671). Theoretical element content (%) C 49 H 34 N 2 O: c,88.26; h,5.14; n,4.20. Measured element content (%): c,88.29; h,5.13; n,4.22.
EXAMPLE 31 Synthesis of Compound 521
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-8, substituting b-1 with equimolar b-5, substituting c-1 with equimolar c-521, synthetic compound 521 (19.61 g), the purity of the solid was ≡ 99.7% by HPLC. Mass spectrum m/z:604.2889 (theory: 604.2878). Theoretical element content (%) C 45 H 36 N 2 : c,89.37; h,6.00; n,4.63. Measured element content (%): c,89.41; h,5.99; n,4.61.
EXAMPLE 32 Synthesis of Compound 542
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-15 and substituting c-1 with equimolar c-240, synthesized compound 542 (19.83 g) was found to have a solid purity of ≡ 99.8% by HPLC. Mass spectrum m/z:685.2786 (theory: 685.2770). Theoretical element content (%) C 53 H 35 N: c,92.81; h,5.14; n,2.04. Measured element content (%): c,92.84; h,5.12; n,2.03.
EXAMPLE 33 Synthesis of Compound 548
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-14 and substituting c-1 with equimolar c-548, synthesized compound 548 (24.34 g) and detected a solid purity of ≡ 99.7% by HPLC. Mass spectrum m/z:791.3566 (theory: 791.3552). Theoretical element content (%) C 61 H 45 N: c,92.50; h,5.73; n,1.77. Measured element content (%): c,92.55; h,5.70; n,1.74.
EXAMPLE 34 Synthesis of Compound 569
Using the same method as in Synthesis example 1, substituting a-1 with equimolar a-2 and substituting c-1 with equimolar c-569, compound 569 (23.16 g) was synthesized, and the purity of the solid was ≡ 99.5% by HPLC. Mass spectrum m/z:771.3673 (theory: 771.3662). Theoretical element content (%) C 58 H 37 D 5 N 2 : c,90.24; h,6.14; n,3.63. Measured element content (%): c,90.26; h,6.11; n,3.65.
EXAMPLE 35 Synthesis of Compound 570
Using the same method as in Synthesis example 1, compound 570 (19.99 g) was synthesized with equal molar substitution of a-15 for a-1, equal molar substitution of b-5 for b-1, equal molar substitution of c-570 for c-1, and HPLC detection of solid purity ≡ 99.4%. Mass spectrum m/z:640.2865 (theory: 640.2878). Theoretical element content (%) C 48 H 36 N 2 : c,89.97; h,5.66; n,4.37. Measured element content (%): c,90.00; h,5.67; n,4.32.
EXAMPLE 36 Synthesis of Compound 572
Using the same method as in Synthesis example 1, compound 572 (20.11 g) was synthesized with equal molar substitution of a-5 for a-1, equal molar substitution of b-5 for b-1, equal molar substitution of c-572 for c-1, and a solid purity of ≡ 99.6% by HPLC. Mass spectrum m/z:669.3408 (theory: 669.3396). Theoretical element content (%) C 51 H 43 N 2 : c,91.44; h,6.47; n,2.09. Measured element content (%): c,91.48; h,6.42; n,2.11.
Green organic light emitting device (first hole transport layer)
Comparative examples 1-2 device preparation examples:
comparative example 1: the organic light emitting device is prepared by utilizing a vacuum thermal evaporation method. The experimental steps are as follows: the ITO substrate is put in distilled water for 3 times, washed by ultrasonic waves for 15 minutes, washed by ultrasonic waves sequentially by solvents such as isopropanol, acetone, methanol and the like after the distilled water is washed, dried and dried at 120 ℃, and sent into an evaporator.
Evaporating a hole injection layer CuPc/20nm, an evaporating hole transmission layer HT-1/80nm and evaporating main bodies H-4 and H-14 on the prepared ITO transparent electrode in a layer-by-layer vacuum evaporation mode: GD-1 doped (47%: 47%:6% mixed) mix/28 nm, then electron transport layer BPhen/25nm, electron injection layer LiF/1nm, cathode Al/130nm were evaporated. And sealing the device in a glove box, thereby preparing an organic light emitting device. After the organic light-emitting device is manufactured according to the steps, the photoelectric property of the device is measured, and the molecular structural formula of the related material is shown as follows:
comparative example 2: the organic light emitting device of comparative example 2 was manufactured in the same manner as comparative example 1, except that the hole transport layer material HT-1 in comparative example 1 was replaced with HT-2.
Comparative example 3: the organic light emitting device of comparative example 3 was manufactured in the same manner as comparative example 1, except that the hole transport layer material HT-1 in comparative example 1 was replaced with HT-3.
Examples 1 to 22
Examples 1 to 22: the hole transport layer material HT-1 of the organic light emitting device was changed to the inventive compounds 4, 9, 21, 31, 65, 138, 152, 186, 255, 331, 388, 407, 420, 422, 505, 520, 521, 526, 548, 560, 569, 570 in this order, and the other steps were the same as comparative example 1.
Test software, a computer, a K2400 digital source list manufactured by Keithley corporation, U.S. and a PR788 spectral scanning luminance meter manufactured by Photo Research corporation, U.S. were combined into a single integrated IVL test system to test the luminous efficiency of an organic light emitting device. Life testing an M6000 OLED life test system from McScience was used. The environment tested was atmospheric and the temperature was room temperature. The results of the light emission characteristics test of the obtained organic light emitting device are shown in table 1. Table 1 shows the results of the light emitting characteristics test of the light emitting devices prepared with the compounds prepared in the examples of the present invention and the comparative substances.
TABLE 1 test of light emitting characteristics of light emitting device
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Note that: t97 means that the current density is 10mA/cm 2 In the case, the time taken for the device brightness to decay to 97%;
as can be seen from the results of table 1, the triarylamine compound containing fused rings of the present invention is used in an organic light-emitting device, and as a first hole transport layer material, it exhibits the advantage of high light-emitting efficiency as compared with comparative examples 1 to 3, and is a hole transport material for an organic light-emitting device having good performance.
Red organic light emitting device (second hole transport layer)
Comparative example 4 device preparation example:
comparative example 4: the organic light emitting device is prepared by utilizing a vacuum thermal evaporation method. The experimental steps are as follows: the ITO transparent substrate is put in distilled water for 3 times, washed by ultrasonic waves for 15 minutes, washed by ultrasonic waves sequentially by solvents such as isopropanol, acetone, methanol and the like after the distilled water is washed, dried and dried at 120 ℃, and sent into an evaporator.
The hole injection layer CuPc/18nm, the first hole transport layer HT1/80nm, the second hole transport layer HT-1/10nm, the luminescent layer (main body RH-6:RH-11:RD-1 (49%: 49%:2% mixed))/26 nm, then the electron transport layer BPhen/22nm, the electron injection layer LiF/0.5nm and the cathode Al/120nm are evaporated on the prepared ITO transparent substrate electrode in a layer-by-layer vacuum evaporation mode. And sealing the device in a glove box, thereby preparing an organic light emitting device. After the organic light-emitting device is manufactured according to the steps, the photoelectric property of the device is measured, and the molecular structural formula of the related material is shown as follows:
examples 23 to 46
Examples 23 to 46: the second hole transport layer material of the organic light emitting device was changed to the inventive compounds 4, 9, 21, 31, 33, 65, 138, 152, 161, 215, 226, 240, 255, 262, 299, 331, 350, 368, 388, 400, 436, 505, 542, 572 in this order, and the other steps were the same as comparative example 4.
Test software, a computer, a K2400 digital source meter 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 driving voltage and luminous efficiency of the organic light emitting device. The results of the light emission characteristics test of the obtained organic light emitting device are shown in table 2. Table 2 shows the results of the light emitting characteristics test of the light emitting devices prepared with the compounds prepared in the examples of the present invention and the comparative substances.
TABLE 2 test of light emitting characteristics of light emitting device
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As can be seen from the results of table 2, the triarylamine-based organic compound containing condensed rings of the present invention is used in an organic light-emitting device, particularly as a second hole transport layer material, and significantly improves the light-emitting efficiency of the organic light-emitting device and reduces the driving voltage, compared to comparative example 4, and is an organic light-emitting material having good performance.
Blue organic light emitting device (cover layer)
Comparative examples 5-6 device preparation examples:
comparative example 5: the organic light emitting device is prepared by utilizing a vacuum thermal evaporation method. The experimental steps are as follows: the ITO-Ag-ITO substrate is put in distilled water for 3 times, ultrasonic washing is carried out for 15 minutes, after the distilled water is washed, solvents such as isopropanol, acetone, methanol and the like are sequentially washed by ultrasonic waves, and then the substrate is dried and dried at 120 ℃ and is sent into an evaporator.
Evaporating a hole injection layer HIL/20nm, an evaporating hole transport layer Spiro-NPB/40nm and an evaporating body BH-1 on the prepared ITO-Ag-ITO transparent electrode in a layer-by-layer vacuum evaporation mode: doping BD-1 (97%: 3% mixture)/22 nm, and then evaporating an electron transport layer Alq 3 ：Liq 3 (1:1)/28 nm, an electron injection layer LiF/1nm, a cathode Mg-Ag/20nm, and a coating layer CP-1/68nm deposited on the cathode. And sealing the device in a glove box, thereby preparing an organic light emitting device. After the organic light-emitting device is manufactured according to the steps, the photoelectric property of the device is measured, and the molecular structural formula of the related material is shown as follows:
Comparative example 6: the organic light emitting device of comparative example 6 was manufactured in the same manner as comparative example 5, except that the capping layer material CP-1 of comparative example 5 was replaced with CP-2.
Examples 47 to 60
Examples 47 to 60: the capping layer material CP-1 of the organic light emitting device was sequentially changed to the inventive compounds 33, 161, 186, 226, 299, 350, 420, 473, 487, 517, 520, 548, 569, 570, and the other steps were the same as comparative example 5.
Test software, a computer, a K2400 digital source list manufactured by Keithley corporation, U.S. and a PR788 spectral scanning luminance meter manufactured by Photo Research corporation, U.S. were combined into a single integrated IVL test system to test the luminous efficiency of an organic light emitting device. Life testing an M6000 OLED life test system from McScience was used. The environment tested was atmospheric and the temperature was room temperature. The results of the light emission characteristics test of the obtained organic light emitting device are shown in table 3. Table 3 shows the results of the luminescence characteristics test of the light emitting devices prepared from the compounds prepared in the examples of the present invention and the comparative substances.
TABLE 3 test of light emitting characteristics of light emitting device
Note that: t95 means that the current density is 10mA/cm 2 In the case, the time taken for the brightness of the device to decay to 95%;
As can be seen from the results of table 3, the triarylamine compound containing fused rings of the present invention is used in an organic light-emitting device, and as a capping material, it is effective in improving light extraction efficiency, and thus luminous efficiency of the organic light-emitting device, as compared with comparative examples 5 to 6, and is an organic light-emitting device capping material having good performance.
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 (7)

1. A triarylamine compound containing condensed rings is characterized in that the molecular structure is shown as a formula I:
wherein the group C is selected from one of the following groups:
wherein the R is 2 The same or different are selected from hydrogen and deuterium;
the saidR 1 One selected from hydrogen, deuterium, substituted or unsubstituted phenyl;
the i is selected from 0, 1, 2 or 3; the j is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said d is selected from 0, 1, 2, 3 or 4; said e is selected from 0, 1, 2, 3, 4, 5 or 6; said f is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when R is 1 When selected from substituted or unsubstituted phenyl, i is selected from 1, and d is selected from 1;
the group B is selected from one of the following groups:
ar is selected from any one of the following groups:
the R is 12 One of the following substituents selected from phenyl, tolyl, biphenyl, naphthyl:
the R is 13 One of deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl and tert-butyl;
the R is 13a One of deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, adamantyl, phenyl and pentadeuterated phenyl;
the R is 13b One of deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, phenyl and pentadeuterated phenyl;
the a is 0, 1, 2, 3 or 4; b is 1, 2, 3, 4 or 5; q is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9The method comprises the steps of carrying out a first treatment on the surface of the When R is 13a When selected from adamantyl, phenyl, pentadeuterated phenyl, the a is 1; when R is 13b When selected from phenyl and pentadeuterated phenyl, a is 1;
the L is 0 Selected from a single bond or one of the following groups:
the L is 1 Selected from a single bond or one of the following groups:
the L is 2 Independently selected from a single bond or one of the following groups:
Wherein "substituted …" in the above "substituted or unsubstituted …" means substitution with deuterium.
2. The compound of claim 1, wherein said group C is selected from one of the following groups:
3. the fused ring-containing triarylamine compound of claim 1 wherein R 12 Selected from phenyl or one of the following substituents:
4. a condensed ring-containing triarylamine compound, wherein the condensed ring-containing triarylamine compound is selected from any one of the following chemical structures:
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5. an organic light-emitting device comprising an anode, a cathode, and an organic layer located between the anode and the cathode or outside one or more of the anode and the cathode, wherein the organic layer contains any one or a combination of at least two of the triarylamine compounds containing condensed rings according to any one of claims 1 to 4.
6. An organic light-emitting device according to claim 5, wherein the organic layer comprises a hole-transporting layer containing any one or a combination of at least two of the triarylamine compounds having condensed rings according to any one of claims 1 to 4.
7. An organic light-emitting device according to claim 5, wherein the organic layer comprises a cover layer containing any one or a combination of at least two of the triarylamine compounds having condensed rings according to any one of claims 1 to 4.
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CN115093332B (en) * 2021-07-01 2023-06-16 四川阿格瑞新材料有限公司 Spiro compound and application thereof
CN113735808B (en) * 2021-09-23 2024-01-26 长春海谱润斯科技股份有限公司 Triarylamine compound and organic electroluminescent device thereof
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140126108A (en) * 2013-04-22 2014-10-30 에스에프씨 주식회사 Asymmetric pyrene derivatives comprising aryl amine group and organic light-emitting diode including the same
KR20160066308A (en) * 2014-12-02 2016-06-10 (주)피엔에이치테크 An electroluminescent compound and an electroluminescent device comprising the same
CN107986975A (en) * 2017-11-08 2018-05-04 长春海谱润斯科技有限公司 A kind of organic luminescent compounds and its organic luminescent device
CN112745264A (en) * 2019-10-31 2021-05-04 东进世美肯株式会社 Novel organic compound for capping layer and organic light-emitting element comprising same
WO2021107737A1 (en) * 2019-11-29 2021-06-03 주식회사 엘지화학 Organic light-emitting element

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015122345A (en) * 2013-12-20 2015-07-02 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． Material for organic electroluminescent devices, and organic electroluminescent device arranged by use thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140126108A (en) * 2013-04-22 2014-10-30 에스에프씨 주식회사 Asymmetric pyrene derivatives comprising aryl amine group and organic light-emitting diode including the same
KR20160066308A (en) * 2014-12-02 2016-06-10 (주)피엔에이치테크 An electroluminescent compound and an electroluminescent device comprising the same
CN107986975A (en) * 2017-11-08 2018-05-04 长春海谱润斯科技有限公司 A kind of organic luminescent compounds and its organic luminescent device
CN112745264A (en) * 2019-10-31 2021-05-04 东进世美肯株式会社 Novel organic compound for capping layer and organic light-emitting element comprising same
WO2021107737A1 (en) * 2019-11-29 2021-06-03 주식회사 엘지화학 Organic light-emitting element

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