CN109053547B - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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Abstract
The invention provides an organic electroluminescent device, and relates to the technical field of organic electroluminescence. The organic electroluminescent device is obtained by designing the hole transport layer and/or the light-emitting auxiliary layer and the electron transport layer which are composed of specific compounds, the electron transport rate is improved through the combination, the injection rate of holes and electrons is effectively balanced, the injection balance of current carriers in the light-emitting layer is realized, the service life deterioration of the device caused by the heat accumulation of the interfaces of the electron transport layer, the electron transport layer and the light-emitting layer is avoided, the organic electroluminescent device has the advantages of high light-emitting efficiency and long service life, and the problems of low service life and low light-emitting efficiency caused by the unbalanced injection of the current carriers and the high starting voltage of the organic electroluminescent device are effectively solved.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic electroluminescent device.
Background
In recent years, OLEDs are widely used in the display field, and compared with LCD display technologies, OLEDs do not need a backlight source, can self-emit light, have significant advantages in voltage characteristics, light emission brightness, light emission efficiency, device weight, response speed, viewing angle, and the like, and are currently the most promising panel display technologies due to their low cost potential.
The organic electroluminescent device is a double injection type device, voltage is applied to the positive end and the negative end, current is injected, electrons and holes pass through an organic layer formed by an organic luminescent material, finally excitons are formed in a luminescent layer in a combined mode, and the excitons return to a stable ground state to radiate and emit light, wherein the structure of the typical organic electroluminescent device generally comprises a cathode, an anode and an organic layer arranged between the electrodes. The composition of the device includes a transparent ITO anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Emission Layer (EL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), a cathode, and the like.
In general, in the future, the OLED is directed to develop a white light device and a full color display device with high efficiency, high brightness, long lifetime, and low cost, but the industrialization process of the technology still faces many key problems, such as that the transport speed of electrons in the electron injection and transport functional layer is slower than that of holes in the hole injection and transport functional layer, which causes carrier mismatch in the light emitting layer, and the transport of excitons on the electron transport layer side causes unnecessary energy accumulation and non-radiative energy dissipation, which causes the reduction of device efficiency and the shortening of lifetime, so that it is an urgent problem to solve to develop an organic electroluminescent device that can balance carriers, reduce non-radiative energy dissipation in the carrier transport process, and obtain an organic electroluminescent device with low driving voltage, high light emitting efficiency, and long lifetime.
Disclosure of Invention
The invention aims to provide an organic electroluminescent device, which adopts a hole transport layer and/or a light-emitting auxiliary layer and an electron transport layer with specific chemical structures for matching to achieve the purpose of carrier injection balance and has the advantages of low driving voltage, high light-emitting efficiency and long service life.
The invention provides an organic electroluminescent device, which comprises a cathode, an anode and an organic layer positioned between the cathode and the anode, wherein the organic layer comprises a hole transport layer and/or a light-emitting auxiliary layer and an electron transport layer, and the hole transport layer and/or the light-emitting auxiliary layer contain a compound shown in a chemical formula (I):
wherein L is1、L2、L3Independently selected from one of a single bond, a substituted or unsubstituted divalent aryl group of C6-C30 and a substituted or unsubstituted divalent heteroaryl group of C3-C30; ar (Ar)1、Ar3Independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl and substituted or unsubstituted spirobifluorenyl; ar (Ar)2Selected from substituted or unsubstituted carbazolyl groups.
Preferably, said L1、L2、L3Independently selected from one of a single bond, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl and substituted or unsubstituted biphenyl.
Preferably, Ar is2Is a group shown as follows:
wherein R is1One selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
R2、R3one selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group of C1 to C10, an alkoxy group of C1 to C10, a substituted or unsubstituted aryl group of C6 to C30, and a substituted or unsubstituted heteroaryl group of C3 to C30, which may be the same or different at each occurrence; or said R2、R3Any two adjacent two of them are fused to form a ring;
a is selected from an integer of 0 to 4, and b is selected from an integer of 0 to 3.
Preferably, Ar is2One selected from the following groups:
preferably, Ar is1、Ar3Independently selected from one of the following groups:
wherein R is4、R5、R6、R7At each appearance phaseOne selected from hydrogen atom, deuterium atom, halogen atom, alkyl of C1-C10, alkoxy of C1-C10, substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30; or said R4、R5、R6、R7Any two adjacent two of them are fused to form a ring; c. d, e and f are independently selected from integers from 0 to 4.
Preferably, Ar is1、Ar3Independently selected from one of the following groups:
preferably, the electron transport layer contains a compound represented by formula (ii):
wherein Ar is4、Ar5、Ar6Independently selected from one of substituted or unsubstituted aryl of C6-C65 and substituted or unsubstituted heteroaryl of C3-C65, and Ar4、Ar5、Ar6At least one of them is selected from the following groups:
wherein R is8、R9Independently selected from one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C6-C30 heteroaryl; r10One selected from hydrogen atom, substituted or unsubstituted C1-C10 alkyl and substituted or unsubstituted C6-C30 aryl.
Preference is given toOf Ar4、Ar5、Ar6At least one selected from the group consisting of:
wherein R is8、R9Independently selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted phenanthroline, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted benzopyrrole, substituted or unsubstituted triazolyl, substituted or unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuryl, One of substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, and substituted or unsubstituted indolyl; r10Selected from hydrogen atom, methyl, ethyl, isopropyl or tert-butyl.
Preferably, Ar is5、Ar6And is selected from the following groups:
wherein R is8、R9Independently selected from one of methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl and substituted or unsubstituted pyrazinyl; r10Selected from hydrogen atom, methyl, ethyl, isopropyl or tert-butyl.
Preferably, Ar is4Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxathiyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted perylenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted benzopyrolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted thienyl, Substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuryl.
The invention has the beneficial effects that:
the invention provides an organic electroluminescent device, which is obtained by adaptively combining a hole transport layer and/or a light-emitting auxiliary layer consisting of a specific compound (I) and an electron transport layer consisting of a specific compound (II).
The organic electroluminescent device adopts a compound (I) as a hole transport layer and/or a luminescence auxiliary layer, and simultaneously contains derivatives of fluorene, spirobifluorene and carbazole, rigid in-plane biphenyl units of the derivatives of fluorene and spirobifluorene enable the derivatives of fluorene and spirobifluorene to have high thermal stability and chemical stability, and carbazole compounds have rigid planar structures and large pi conjugated systems to enable the carbazole compounds to have good thermal stability and high carrier mobility, and Ar is used for removing Ar1、Ar2、Ar3The synergistic effect between the compounds improves the hole transmission capability and stability of the compounds, and realizes the charge balance in the light-emitting layer; further, by making the double-clickThe optimization of the azole structure regulates and controls the pi-pi accumulation among molecules, so that the compound has proper highest occupied molecular orbital energy level and high T1 value, is used as a light-emitting auxiliary layer material between a hole transport layer and a light-emitting layer, can reduce the energy level difference between the light-emitting layer and an anode interface, is more favorable for realizing the charge balance in the light-emitting layer, improves the color purity, the light-emitting efficiency and the service life of a device, and reduces the driving voltage of the device.
The organic electroluminescent device adopts the compound (II) as an electron transport layer, and is mainly used for improving the mobility of electrons reaching a light emitting layer, so that the recombination probability of excitons in the light emitting layer is improved, and the light emitting efficiency of the device is improved. The compound (II) introduces fluorene groups into 1,3 and 5 positions of triazine which is a strong electron-withdrawing group to form a three-dimensional space structure, so that effective intermolecular accumulation can be formed, the compound is not easy to crystallize and is easy to form a film; and triazine and fluorene groups are connected through a benzene ring or a biphenyl ring to form an extensible large-pi conjugated system, so that electrons can easily flow, the electron mobility of the electron transmission layer of the organic electroluminescent device is improved, and the threshold value for limiting the luminous efficiency of the device is fundamentally improved.
The organic electroluminescent device of the invention effectively adapts and combines the organic luminescent materials adopted by the hole transport layer and/or the luminescence auxiliary layer and the electron transport layer, improves the electron migration speed of the electron transport layer, and properly adjusts the hole transport layer and/or the luminescence auxiliary layer, thereby realizing the balance of electron and hole injection and recombination of the luminescent layer, avoiding the migration of current carriers to the transport layer side, avoiding the dissipation of non-radiative energy, and obtaining the organic electroluminescent device with low driving voltage, high luminous efficiency and long service life.
Detailed Description
The following will clearly and completely describe the technical solutions of the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the scope of protection of the present invention.
It is to be understood that, unless defined otherwise, technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
The aryl group in the present invention refers to a general term of the group remaining after one hydrogen atom is removed from one aromatic nucleus carbon of the aromatic hydrocarbon molecule, and may be a monocyclic aryl group or a condensed ring aryl group, and may be selected from, for example, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a fluorenyl group, a benzophenanthryl group, or the like, but is not limited thereto.
The heteroaryl group in the present invention refers to a general term of a group obtained by replacing one or more aromatic nuclear carbons in an aryl group with a heteroatom, including but not limited to oxygen, sulfur or nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group or a fused ring heteroaryl group, and may be selected from, for example, a pyridyl group, a quinolyl group, a carbazolyl group, a thienyl group, a benzothienyl group, a furyl group, a benzofuryl group, a pyrimidyl group, a benzopyrimidinyl group, an imidazolyl group, or a benzimidazolyl group, and the like, but is not limited thereto.
The divalent aryl group in the present invention refers to a general term of the divalent group remaining after removing one hydrogen atom from each of two aromatic core carbons of the aromatic hydrocarbon molecule, and may be a divalent monocyclic aryl group or a divalent condensed ring aryl group, and may be selected from, for example, phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene, pyrenylene, fluorenylene, or benzophenanthrylene, but is not limited thereto.
The divalent heteroaryl group in the present invention refers to a general term of a group obtained by replacing one or more aromatic core carbons in a divalent aryl group with a heteroatom including but not limited to oxygen, sulfur or nitrogen atom, and the divalent heteroaryl group may be a divalent monocyclic heteroaryl group or a divalent fused cyclic heteroaryl group, and may be selected from, for example, a pyridylene group, a quinolylene group, a carbazolyl group, a thienylene group, a benzothiophenyl group, a furylene group, a benzofuranylene group, a pyrimidylene group, a benzopyrimidine group, an imidazolyl group or a benzimidazolyl group, and the like, but not limited thereto.
The alkyl group in the present invention refers to a hydrocarbon group formed by removing one or more hydrogen atoms from an alkane molecule, and may be a straight-chain alkyl group, a branched-chain alkyl group, or a cyclic alkyl group, and examples thereof may include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, cyclopentyl, cyclohexyl, and the like.
The alkoxy group in the present invention refers to a group in which an alkyl group is bonded to an oxygen atom, and examples may include, but are not limited to, methoxy, ethoxy, 2-propoxy, 2-cyclohexyloxy, and the like.
The fused ring-forming as described in the present invention means that two groups are connected to each other by a chemical bond. As follows:
in the present invention, the condensed synthetic ring may be a five-membered ring or a six-membered ring, such as phenyl, naphthyl, cyclohexanophenyl, quinolyl, isoquinolyl, dibenzothienyl, phenanthryl or pyrenyl, but is not limited thereto.
The invention provides an organic electroluminescent device, which comprises a cathode, an anode and an organic layer positioned between the cathode and the anode, wherein the organic layer comprises a hole transport layer and/or a light-emitting auxiliary layer and an electron transport layer, and the hole transport layer and/or the light-emitting auxiliary layer contain a compound shown in a chemical formula (I):
wherein L is1、L2、L3Independently selected from one of a single bond, a substituted or unsubstituted divalent aryl group of C6-C30 and a substituted or unsubstituted divalent heteroaryl group of C3-C30; ar (Ar)1、Ar3Independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl and substituted or unsubstituted spirobifluorenyl; ar (Ar)2Selected from substituted or unsubstituted carbazolyl groups.
The "substituted or unsubstituted" in the present invention is a substituent independently selected from deuterium atom, cyano group, nitro group, halogen atom, alkyl group of C1-C10, alkoxy group of C1-C10, alkylthio group of C1-C10, aryl group of C6-C30, aryloxy group of C6-C30, arylthio group of C6-C30, heteroaryl group of C3-C30, silyl group of C1-C30, alkylamino group of C2-C10, arylamine group of C6-C30, etc., for example, deuterium atom, cyano group, nitro group, halogen, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, methoxy group, methylthio group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, phenanthryl group, benzophenanthryl group, perylene group, pyrenyl group, fluorenyl group, 9-dimethylfluorenyl group, benzyl group, phenoxy group, phenylthio group, dianilinyl group, dimethylamino group, carbazolyl group, 9-phenylcarbazolyl group, Furyl, thienyl, triphenylsilyl, trimethylsilyl, trifluoromethyl, phenothiazinyl, phenoxazinyl, acridinyl, piperidinyl, pyridyl, pyrazinyl, triazinyl, pyrimidinyl, and the like, but is not limited thereto.
According to the present invention, the organic layer includes a hole transport layer and/or a light emission auxiliary layer, an electron transport layer, and for example, the following may be mentioned, but not limited thereto: 1. the organic layer comprises a hole transport layer and an electron transport layer; or 2, the organic layer comprises a light-emitting auxiliary layer and an electron transport layer; or 3, the organic layer comprises a hole transport layer, a light-emitting auxiliary layer and an electron transport layer.
Preferably, said L1、L2、L3Independently selected from one of single bond, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl and substituted or unsubstituted biphenyl, more preferably, the L is1、L2、L3Independently selected from one of single bond, phenyl, naphthyl and biphenyl.
Preferably, Ar is2Is a group shown as follows:
wherein R is1Selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substitutedOr one of unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; preferably, said R is1One selected from substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C3-C18 heteroaryl; more preferably, R is1One selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl and carbazolyl.
R2、R3One selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group of C1 to C10, an alkoxy group of C1 to C10, a substituted or unsubstituted aryl group of C6 to C30, and a substituted or unsubstituted heteroaryl group of C3 to C30, which may be the same or different at each occurrence; or said R2、R3Any two adjacent two of them are fused to form a ring; preferably, said R is2、R3The same or different at each occurrence is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C1-C4 alkyl group, a substituted or unsubstituted C6-C18 aryl group, a substituted or unsubstituted C3-C18 heteroaryl group, or said R2、R3Any two adjacent two of them are fused to form a ring; more preferably, R is2、R3One selected from a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a carbazolyl group, or the R is the same or different at each occurrence2、R3Any two adjacent of them are fused to form a benzene ring.
a is selected from an integer of 0 to 4, and b is selected from an integer of 0 to 3.
Preferably, Ar is2One selected from the following groups:
preferably, Ar is1、Ar3Independently selected from one of the following groups:
wherein R is4、R5、R6、R7One selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group of C1 to C10, an alkoxy group of C1 to C10, a substituted or unsubstituted aryl group of C6 to C30, and a substituted or unsubstituted heteroaryl group of C3 to C30, which may be the same or different at each occurrence; or said R4、R5、R6、R7Any two adjacent two of them are fused to form a ring; c. d, e and f are independently selected from integers from 0 to 4. Preferably, said R is4、R5、R6、R7The same or different at each occurrence is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C1-C4 alkyl group, a substituted or unsubstituted C6-C18 aryl group, a substituted or unsubstituted C3-C18 heteroaryl group, or said R4、R5、R6、R7Any two adjacent two of them are fused to form a ring; more preferably, R is4、R5、R6、R7One selected from a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a carbazolyl group, or the R is the same or different at each occurrence4、R5、R6、R7Any two adjacent of them are fused to form a benzene ring.
Preferably, Ar is1、Ar3Independently selected from one of the following groups:
by way of example, without particular limitation, the compound of formula (i) according to the present invention is selected from any one of the following structures:
preferably, the electron transport layer of the present invention comprises a compound represented by formula (ii):
wherein Ar is4、Ar5、Ar6Independently selected from one of substituted or unsubstituted aryl of C6-C65 and substituted or unsubstituted heteroaryl of C3-C65, and Ar4、Ar5、Ar6At least one of them is selected from the following groups:
wherein R is8、R9Independently selected from substituted or substitutedOne of unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C6-C30 heteroaryl; r10One selected from hydrogen atom, substituted or unsubstituted C1-C10 alkyl and substituted or unsubstituted C6-C30 aryl.
Preferably, R8、R9Independently selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted phenanthroline, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted benzopyrrole, substituted or unsubstituted triazolyl, substituted or unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuryl, One of substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, and substituted or unsubstituted indolyl; r10Selected from hydrogen atom, methyl, ethyl, isopropyl or tert-butyl.
Preferably, Ar is4、Ar5、Ar6At least one selected from the group consisting of:
wherein R is8、R9Independently selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted phenanthroline, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidylOne of a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted benzopyrrole group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, and a substituted or unsubstituted indolyl group; r10Selected from hydrogen atom, methyl, ethyl, isopropyl or tert-butyl.
Preferably, Ar is5、Ar6And is selected from the following groups:
wherein R is8、R9Independently selected from one of methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl and substituted or unsubstituted pyrazinyl; r10Selected from hydrogen atom, methyl, ethyl, isopropyl or tert-butyl.
Preferably, Ar is4Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxathiyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted perylenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinylOne of a pyrrolyl group, a substituted or unsubstituted benzopyrrole group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted dibenzofuryl group.
By way of example, without particular limitation, the electron transport layer of the organic electroluminescent device according to the present invention is selected from any one of the following structures:
although specific compound structures of the hole transport layer, the light emission auxiliary layer and the electron transport layer according to the present invention are described above, the present invention is not limited to the above-described compound structures, and any group having the substituent defined as above is included based on the following formulae (I) and (ii).
The hole transport layer and/or luminescence auxiliary layer compounds (i) according to the present invention can be prepared by conventional coupling reactions, for example, by the following synthetic routes, but the present invention is not limited thereto:
containing Ar3The aromatic amine compound (A) of (A) is first reacted with a compound containing Ar1The bromide (B) undergoes Buchwald reaction to obtain an intermediate M; intermediate M is further reacted with a compound containing Ar2Bromide of (C)Buchwald reaction is carried out, and the target compound (I) is finally obtained.
Wherein Ar is1、Ar2、Ar3And L1、L2、L3The definitions of (a) and (b) are as described above and will not be described in detail herein.
The electron transport layer compound (II) is obtained through the following synthetic route:
wherein Ar is4、Ar5、Ar6The definitions of (a) and (b) are as described above and will not be described in detail herein.
Raw materials e, Ar4-B(OH)2Carrying out a Suzuki coupling reaction, taking palladium tetratriphenylphosphine as a catalyst, potassium carbonate as an alkali and tetrahydrofuran as a solvent, and carrying out reflux reaction to obtain an intermediate f; intermediates f, Ar5-B(OH)2Carrying out a Suzuki coupling reaction, taking palladium tetratriphenylphosphine as a catalyst, potassium carbonate as an alkali and tetrahydrofuran as a solvent, and carrying out reflux reaction to obtain an intermediate g; intermediate g, Ar6-B(OH)2And carrying out a reflux reaction by using palladium tetratriphenylphosphine as a catalyst, potassium carbonate as an alkali and tetrahydrofuran as a solvent through a Suzuki coupling reaction to obtain a compound II.
The reaction conditions of the above reactions are not particularly limited in the present invention, and the reaction conditions known to those skilled in the art can be adopted, so that the preparation method is simple and the raw materials are easily available.
The organic electroluminescent device of the present invention comprises a cathode, an anode, and an organic layer located between the cathode and the anode, wherein the organic layer of the present invention comprises a hole transport layer and/or a light-emitting auxiliary layer, and an electron transport layer, wherein the hole transport layer and the light-emitting auxiliary layer may exist separately or simultaneously, for example, the following cases may be included, but are not limited thereto: 1. the organic layer comprises a hole transport layer and an electron transport layer; or 2, the organic layer comprises a light-emitting auxiliary layer and an electron transport layer; or 3, the organic layer comprises a hole transport layer, a light-emitting auxiliary layer and an electron transport layer.
Wherein the hole transport layer and/or the luminescence auxiliary layer contain a compound (I), and the electron transport layer contains a compound (II).
In addition, the organic layer may further include at least one of a hole injection layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron injection layer, and the like. The light-emitting layer can be in a light-emitting host doped light-emitting guest form, and can also be a single substance as the light-emitting layer.
The light-emitting auxiliary layer is positioned between the hole transport layer and the light-emitting layer, has good hole transport capacity and electron blocking capacity, is used for balancing current carriers, improves the recombination probability of holes and electrons in the light-emitting layer, avoids the transmission of the electrons to the anode side, and therefore prolongs the service life of the organic light-emitting device.
Preferably, the anode is made of ITO.
Preferably, the hole injection layer is selected from 2-TNATA, CuPc, m-MTDATA, DNTPD, etc., and may be a single structure composed of a single substance or a single-layer structure or a multi-layer structure composed of different substances.
Preferably, the hole transport layer is selected from the group consisting of the compounds I, NPB, TDATA, TPD, TAPC, Spiro-TAD, etc. according to the present invention, and may be a single structure composed of a single substance or a single-layer structure or a multi-layer structure composed of different substances.
Preferably, the light-emission auxiliary layer is selected from the group consisting of the compound (i) according to the present invention, NPB, TDATA, TPD, TAPC, Spiro-TAD, and the like, and may be a single structure composed of a single substance or a single-layer structure or a multi-layer structure composed of different substances, unlike the hole transport layer.
Preferably, the electron blocking layer may be selected from NPB, TDATA, TPD, TAPC, Spiro-TAD, and the like.
Preferably, the light emitting layer host is selected from the group consisting of ADN, CPB, mCP, TCTA, 3Ph-anthracene, α -ADN, 4P-NPB, DPVBI, TCP, TCTA, Alq3And the like, and may be a single structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances.
Preferably, the light-emitting layer guest is selected from TPD, DPAP-DPPA and TPPDA、Ir(ppy)3、Ir(ppy)2(acac)、Ir(piq)3、 Ir(piq)2(acac), FirPic, DCJTB, DCJT, DCM2, DMQA, DBQA, TMDBQA, HAT-CN, F4-TCNQ, etc.
Preferably, the hole blocking layer is selected from BCP, TPBi, Alq3Liq, BALq, TAZ and NTAZ.
Preferably, the electron transport layer is selected from the compounds (II) according to the invention.
Preferably, the electron injection layer may be selected from LiF.
Preferably, the cathode is selected from Al.
The organic electroluminescent device of the present invention preferably has the following structure:
1. substrate/ITO/hole injection layer/hole transport layer (compound i)/light emitting layer/electron transport layer (compound ii)/electron injection layer/Al;
2. substrate/ITO/hole injection layer/hole transport layer/light-emitting auxiliary layer (compound i)/light-emitting layer/electron transport layer (compound ii)/electron injection layer/Al.
3. substrate/ITO/hole injection layer/hole transport layer (compound i)/luminescence auxiliary layer (compound i)/luminescent layer/electron transport layer (compound ii)/electron injection layer/Al;
4. substrate/ITO/hole injection layer/hole transport layer (compound i)/light-emitting auxiliary layer/light-emitting layer/electron transport layer (compound ii)/electron injection layer/Al.
However, the structure of the organic electroluminescent device is not limited thereto. The organic electroluminescent device can be selected and combined according to the parameter requirements of the device and the characteristics of materials, and part of organic layers can be added or omitted.
The organic electroluminescent device can be applied to the application fields of flat panel displays, illumination light sources, signboards, signal lamps and the like.
The invention is explained in more detail by the following examples, without wishing to restrict the invention accordingly. 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 inventive effort.
The raw materials used in the following examples are not particularly limited, and may be commercially available products or prepared by methods known to those skilled in the art.
EXAMPLE 1 Synthesis of Compound HT2-1
To 150ml of dehydrated toluene were added bromide B-1(5.93g, 15mmol), amine compound A-1(3.14g, 15mmol) and sodium tert-butoxide (2.88g, 30mmol) under argon, followed by stirring and reaction at 80 ℃ for 8 hours with palladium acetate (0.07g, 0.3mmol) and tri-tert-butylphosphine (0.06g, 0.3 mmol). After cooling, filtration through a celite/silica funnel, removal of the organic solvent from the filtrate by distillation under reduced pressure, recrystallization of the resulting residue in toluene, filtration of the resulting solid and drying to give intermediate M-1.
50ml of anhydrous xylene was added to intermediate M-1(5.24g, 10mmol), bromide C-1(4.87g, 10mmol), tris (dibenzylideneacetone) dipalladium (0.14g, 0.15mmol), tri-tert-butylphosphine tetrafluoroborate (0.087g, 0.3mmol), and sodium tert-butoxide (1.9g, 20mmol) under argon atmosphere, and the mixture was refluxed for 8 hours. Cooling to 50 ℃ C, filtration through celite/silica gel, concentration of the filtrate, purification of the resulting residue by column chromatography on silica gel and recrystallization of the crude product from toluene gave compound HT2-1(6.13g, 6.6mmol) in 66% yield. Mass spectrum m/z: 929.50 (calculated value: 929.38). Theoretical element content (%) C70H47N3: c, 90.39; h, 5.09; n, 4.52. Measured elemental content (%): c, 90.47; h, 5.04; n, 4.53. The above results confirmed that the obtained product was the objective product.
Example 2: preparation of Compound HT2-4
Substitution of bromide B-1 to isoCompound HT2-4 was obtained by the same procedure as in example 1 except for the use of a molar amount of bromide B-4. Mass spectrum m/z: 1041.38 (calculated value: 1041.50). Theoretical element content (%) C78H63N3: c, 89.88; h, 6.09; and N, 4.03. Measured elemental content (%): c, 89.80; h, 6.06; and N, 4.03. The above results confirmed that the obtained product was the objective product.
Example 3: preparation of Compound HT2-5
Compound HT2-5 was obtained by replacing bromide B-1 with an equimolar amount of bromide B-5 and carrying out the same procedures as in example 1. Mass spectrum m/z: 1005.29 (calculated value: 1005.41). Theoretical element content (%) C76H51N3: c, 90.72; h, 5.11; and N, 4.18. Measured elemental content (%): c, 90.85; h, 5.10; and N, 4.17. The above results confirmed that the obtained product was the objective product.
Example 4: preparation of Compound HT2-10
Compound HT2-10 was obtained by replacing bromide B-1 with an equimolar amount of bromide B-10 and carrying out the same procedures as in example 1. Mass spectrum m/z: 979.28 (calculated value: 979.39). Theoretical element content (%) C74H49N3: c, 90.67; h, 5.04; and N, 4.29. Measured elemental content (%): c, 90.74; h, 5.02; and N, 4.27. The above results confirmed that the obtained product was the objective product.
Example 5: preparation of Compound HT2-13
Replacing bromide B-1 with an equimolar amount of bromide B-13 and carrying out the other stepsThe same procedure as in example 1 gave compound HT 2-13. Mass spectrum m/z: 979.29 (calculated value: 979.39). Theoretical element content (%) C74H49N3: c, 90.67; h, 5.04; and N, 4.29. Measured elemental content (%): c, 90.73; h, 5.02; and N, 4.26. The above results confirmed that the obtained product was the objective product.
Example 6: preparation of Compound HT2-14
Compound HT2-14 was obtained by replacing the amide A-1 with an equimolar amount of bromide A-14 and carrying out the same procedures as in example 1. Mass spectrum m/z: 979.27 (calculated value: 979.39). Theoretical element content (%) C74H49N3: c, 90.67; h, 5.04; and N, 4.29. Measured elemental content (%): c, 90.72; h, 5.04; and N, 4.28. The above results confirmed that the obtained product was the objective product.
Example 7: preparation of Compound HT2-21
Compound HT2-21 was obtained by the same procedure as in example 1 except that bromide B-1 was replaced with an equal molar amount of bromide B-4 and bromide C-1 was replaced with an equal molar amount of bromide C-21. Mass spectrum m/z: 1041.62 (calculated value: 1041.50). Theoretical element content (%) C78H63N3: c, 89.88; h, 6.09; and N, 4.03. Measured elemental content (%): c, 89.93; h, 6.09; and N, 4.03. The above results confirmed that the obtained product was the objective product.
Example 8: preparation of Compound HT2-25
Replacement of bromide B-1 with equimolar amounts of bromide B-4 and bromide C-1Compound HT2-25 was obtained by replacing bromide C-25 with an equimolar amount and carrying out the same procedures as in example 1. Mass spectrum m/z: 1041.39 (calculated value: 1041.50). Theoretical element content (%) C78H63N3: c, 89.88; h, 6.09; and N, 4.03. Measured elemental content (%): c, 89.78; h, 6.07; and N, 4.02. The above results confirmed that the obtained product was the objective product.
Example 9: preparation of Compound HT2-26
Compound HT2-26 was obtained by replacing bromide C-1 with an equimolar amount of bromide C-26 and carrying out the same procedures as in example 1. Mass spectrum m/z: 880.27 (calculated value: 880.38). Theoretical element content (%) C67H48N2: c, 91.33; h, 5.49; and N, 3.18. Measured elemental content (%): c, 91.28; h, 5.46; and N, 3.17. The above results confirmed that the obtained product was the objective product.
Example 10: preparation of Compound HT2-29
Compound HT2-29 was obtained by the same procedure as in example 1 except that bromide B-1 was replaced with an equal molar amount of bromide B-4 and bromide C-1 was replaced with an equal molar amount of bromide C-26. Mass spectrum m/z: 992.46 (calculated value: 992.51). Theoretical element content (%) C75H64N2: c, 90.69; h, 6.49; and N, 2.82. Measured elemental content (%): c, 90.61; h, 6.45; n, 2.84. The above results confirmed that the obtained product was the objective product.
Example 11: preparation of Compound HT2-30
Adding bromineCompound HT2-30 was obtained by replacing compound B-1 with an equimolar amount of bromide B-5 and replacing bromide C-1 with an equimolar amount of bromide C-26, and the other procedures were the same as in example 1. Mass spectrum m/z: 956.54 (calculated value: 956.41). Theoretical element content (%) C73H52N2: c, 91.60; h, 5.48; and N, 2.93. Measured elemental content (%): c, 91.70; h, 5.48; and N, 2.94. The above results confirmed that the obtained product was the objective product.
Example 12: preparation of Compound HT2-35
Compound HT2-35 was obtained by the same procedure as in example 1 except that bromide B-1 was replaced with an equal molar amount of bromide B-10 and bromide C-1 was replaced with an equal molar amount of bromide C-26. Mass spectrum m/z: 930.34 (calculated value: 930.40). Theoretical element content (%) C71H50N2: c, 91.58; h, 5.41; and N, 3.01. Measured elemental content (%): c, 91.49; h, 5.40; and N, 3.02. The above results confirmed that the obtained product was the objective product.
Example 13: preparation of Compound HT2-38
Compound HT2-38 was obtained by the same procedure as in example 1 except that bromide B-1 was replaced with an equal molar amount of bromide B-13 and bromide C-1 was replaced with an equal molar amount of bromide C-26. Mass spectrum m/z: 930.32 (calculated value: 930.40). Theoretical element content (%) C71H50N2: c, 91.58; h, 5.41; and N, 3.01. Measured elemental content (%): c, 91.52; h, 5.40; and N, 3.02. The above results confirmed that the obtained product was the objective product.
Example 14: preparation of Compound HT2-49
Compound HT2-49 was obtained by the same procedure as in example 1 except that bromide B-1 was replaced with an equal molar amount of bromide B-4 and bromide C-1 was replaced with an equal molar amount of bromide C-49. Mass spectrum m/z: 992.47 (calculated value: 992.51). Theoretical element content (%) C75H64N2: c, 90.69; h, 6.49; and N, 2.82. Measured elemental content (%): c, 90.71; h, 6.47; n, 2.81. The above results confirmed that the obtained product was the objective product.
Example 15: preparation of Compound HT2-51
Compound HT2-51 was obtained by replacing bromide C-1 with an equimolar amount of bromide C-51 and carrying out the same procedures as in example 1. Mass spectrum m/z: 764.44 (calculated value: 764.32). Theoretical element content (%) C58H40N2: c, 91.07; h, 5.27; and N, 3.66. Measured elemental content (%): c, 91.11; h, 5.27; and N, 3.65. The above results confirmed that the obtained product was the objective product.
Example 16: preparation of Compound HT2-54
Compound HT2-54 was obtained by the same procedure as in example 1 except that bromide B-1 was replaced with an equal molar amount of bromide B-4 and bromide C-1 was replaced with an equal molar amount of bromide C-54. Mass spectrum m/z: 926.37 (calculated value: 926.46). Theoretical element content (%) C70H58N2: c, 90.67; h, 6.31; and N, 3.02. Measured elemental content (%): c, 90.61; h, 6.29; and N, 3.02. The above results confirmed that the obtained product was the objective product.
Example 17: preparation of Compound HT2-55
Compound HT2-55 was obtained by the same procedure as in example 1 except that bromide B-1 was replaced with an equal molar amount of bromide B-5 and bromide C-1 was replaced with an equal molar amount of bromide C-54. Mass spectrum m/z: 890.29 (calculated value: 890.37). Theoretical element content (%) C68H46N2: c, 91.65; h, 5.20; and N, 3.14. Measured elemental content (%): c, 91.60; h, 5.19; and N, 3.12. The above results confirmed that the obtained product was the objective product.
Example 18: preparation of Compound HT2-76
Compound HT2-76 was obtained by replacing bromide C-1 with an equimolar amount of bromide C-76 and carrying out the same procedures as in example 1. Mass spectrum m/z: 870.25 (calculated value: 870.31). Theoretical element content (%) C64H42N2S: c, 88.24; h, 4.86; n, 3.22; and S, 3.68. Measured elemental content (%): c, 88.20; h, 4.89; n, 3.22; and S, 3.68. The above results confirmed that the obtained product was the objective product.
Example 19: preparation of Compound HT2-80
Compound HT2-80 was obtained by the same procedure as in example 1 except that bromide B-1 was replaced with an equal molar amount of bromide B-5 and bromide C-1 was replaced with an equal molar amount of bromide C-76. Mass spectrum m/z: 964.25 (calculated value: 964.34). Theoretical element content (%) C70H46N2S: c, 88.76; h, 4.90; n, 2.96; and S, 3.38. Measured elemental content (%): c, 88.70; h, 4.89; n, 2.96; and S, 3.38. The above results confirmed that the obtained product was the objective product.
Example 20: preparation of Compound HT2-101
Compound HT2-101 was obtained by replacing bromide C-1 with an equimolar amount of bromide C-101 and performing the same procedures as in example 1. Mass spectrum m/z: 854.23 (calculated value: 854.33). Theoretical element content (%) C64H42N2O: c, 89.90; h, 4.95; n, 3.28; o, 1.87. Measured elemental content (%): c, 89.85; h, 4.94; n, 3.26; o, 1.88. The above results confirmed that the obtained product was the objective product.
Example 21: preparation of Compound HT2-105
Compound HT2-105 was obtained by the same procedure as in example 1 except that bromide B-1 was replaced with an equal molar amount of bromide B-5 and bromide C-1 was replaced with an equal molar amount of bromide C-101. Mass spectrum m/z: 930.25 (calculated value: 930.36). Theoretical element content (%) C70H46N2O: c, 90.29; h, 4.98; n, 3.01; o, 1.72. Measured elemental content (%): c, 90.26; h, 4.94; n, 3.02; o, 1.72. The above results confirmed that the obtained product was the objective product.
Example 22: preparation of Compound HT2-126
Compound HT2-126 was obtained by replacing amide A-1 with an equimolar amount of amide A-126 and performing the same procedures as in example 1. Mass spectrum m/z: 929.50 (calculated value: 929.38). Theoretical element content (%) C70H47N3: c, 90.39; h, 5.09; n, 4.52. Measured elemental content (%): c, 90.47; h, 5.04; n,4.53. The above results confirmed that the obtained product was the objective product.
Example 23: preparation of Compound HT2-130
Compound HT2-130 was obtained by replacing bromide B-1 with an equimolar amount of bromide B-130 and carrying out the same procedures as in example 1. Mass spectrum m/z: 1013.35 (calculated value: 1013.47). Theoretical element content (%) C76H59N3: c, 89.99; h, 5.86; n, 4.14. Measured elemental content (%): c, 89.89; h, 5.84; and N, 4.12. The above results confirmed that the obtained product was the objective product.
Example 24: preparation of Compound HT2-145
Compound HT2-145 was obtained by replacing amide A-1 with an equimolar amount of amide A-126 and bromide C-1 with an equimolar amount of bromide C-26, and the procedure was otherwise the same as in example 1. Mass spectrum m/z: 880.49 (calculated value: 880.38). Theoretical element content (%) C67H48N2: c, 91.33; h, 5.49; and N, 3.18. Measured elemental content (%): c, 91.37; h, 5.49; and N, 3.18. The above results confirmed that the obtained product was the objective product.
Example 25: preparation of Compound HT2-163
Compound HT2-163 was obtained by replacing bromide C-1 with an equimolar amount of bromide C-54 and carrying out the same procedures as in example 1. Mass spectrum m/z: 814.29 (calculated value: 814.33). Theoretical element content (%) C62H42N2: c, 91.37; h, 5.19; n, 3.44. Measured elemental content (%): c,91.30(ii) a H, 5.19; n, 3.43. The above results confirmed that the obtained product was the objective product.
Example 26: preparation of Compound HT2-167
Compound HT2-167 was obtained by replacing bromide C-1 with an equimolar amount of bromide C-167 in the same manner as in example 1. Mass spectrum m/z: 764.28 (calculated value: 764.32). Theoretical element content (%) C58H40N2: c, 91.07; h, 5.27; and N, 3.66. Measured elemental content (%): c, 91.00; h, 5.29; and N, 3.66. The above results confirmed that the obtained product was the objective product.
Example 27: preparation of Compound HT2-194
Compound HT2-194 was obtained by replacing the equimolar amount of amide A-1 with the amide A-194 and performing the same procedures as in example 1. Mass spectrum m/z: 813.26 (calculated value: 813.31). Theoretical element content (%) C61H39N3: c, 90.01; h, 4.83; and N, 5.16. Measured elemental content (%): c, 89.98; h, 4.82; and N, 5.16. The above results confirmed that the obtained product was the objective product.
Example 28: preparation of Compound HT2-203
Compound HT2-203 was obtained by replacing bromide B-203 with an equimolar amount of bromide B-1 and carrying out the same procedures as in example 1. Mass spectrum m/z: 691.20 (calculated value: 691.30). Theoretical element content (%) C51H37N3: c, 88.54; h, 5.39; and N, 6.07. Measured elemental content (%): c, 88.50; h, 5.39; and N, 6.06. The above results confirmedThe obtained product is the target product.
EXAMPLE 29 Synthesis of Compound ET1
Step 1: 3, 5-Dichlorobiphenyl (9.4g, 42.4mmol) was charged into a three-necked flask, THF (100 mL) was added, and the mixture was stirred at-78 ℃ for 30 minutes under nitrogen protection, then 21mL of n-butyllithium (2.5M) was added, and the mixture was reacted for 1 hour, 14g of triisopropyl borate was further added, and the reaction was carried out at low temperature for 1 hour, followed by gradual recovery to room temperature. After-treatment, 2M hydrochloric acid was added to the system to adjust the pH of the solution to 4-5, the mixture was allowed to stand for liquid separation, the aqueous layer was extracted with ethyl acetate, and the organic layers were combined and spin-dried to obtain intermediate ET1-1(8.2g, 80%).
Step 2: tetrakistriphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) were added to a solution of intermediate ET1-1(44.3g, 183mmol) and 2-bromo-9, 9-dimethylfluorene (50.3g, 185mmol) in degassed tetrahydrofuran (500mL), and the mixture was heated at reflux for 4 h. Suction filtration while hot gave a large amount of solid, which was dissolved in a solvent, concentrated and subjected to silica gel column chromatography to give intermediate ET1-2(50.0g, 70%).
Step 3: tetrakistriphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) were added to a solution of intermediate ET1-2(150g, 384mmol) and 2, 4-dibromo-6-phenyl-1, 3, 5-triazine (41.3g, 183mmol) in degassed tetrahydrofuran (500mL), and the mixture was heated at reflux for 4 h. Suction filtration while hot gave a large amount of solid, which was dissolved in a solvent, followed by concentration and column chromatography on silica gel to give compound ET1(92.9g, 60%). Mass spectrum m/z: 845.31 (calculated value: 845.38). Theoretical element content (%) C63H47N3: c, 89.43; h, 5.60; and N, 4.97. Measured elemental content (%): c, 89.40; h, 5.59; and N, 4.96. The above results confirmed that the obtained product was the objective product.
EXAMPLE 30 Synthesis of Compound ET41
Step 1: the 4H-cyclopentaphenanthrene is substituted by methyl iodide and then reacts with liquid bromine to obtain 8-bromo-4, 4-dimethylcyclopentaphenanthrene. 8-bromo-4, 4-dimethylcyclopentaphenanthrene (12.6g, 42.4mmol) was charged into a three-necked flask, and 100mL of THF was added under nitrogen protection, and stirred at-78 ℃ for 30 minutes, then 21mL of n-butyllithium (2.5M) was added, followed by reaction for 1 hour, further addition of 7g of triisopropyl borate, reaction at low temperature for 1 hour, and gradual return to room temperature. After-treatment, 2M hydrochloric acid was added to the system to adjust the pH of the solution to 4-5, the mixture was allowed to stand for liquid separation, the aqueous layer was extracted with ethyl acetate, and the organic layers were combined and spin-dried to obtain intermediate ET41-1(8.3g, 75%).
Step 2: tetrakistriphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) were added to a solution of intermediate ET41-1(100.6g, 384mmol) and 2, 4-dibromo-6-phenyl-1, 3, 5-triazine (41.3g, 183mmol) in degassed tetrahydrofuran (500mL), and the mixture was heated at reflux for 4 h. Suction filtration while hot gave a large amount of solid, which was dissolved in a solvent, followed by concentration and column chromatography on silica gel to give compound ET41(70.0g, 65%). Mass spectrum m/z: 589.20 (calculated value: 589.25). Theoretical element content (%) C43H31N3: c, 87.58; h, 5.30; and N, 7.13. Measured elemental content (%): c, 87.51; h, 5.30; and N, 7.10. The above results confirmed that the obtained product was the objective product.
EXAMPLE 31 Synthesis of Compound ET63
Step 1: the 4H-cyclopentaphenanthrene is reduced by Pd/C and then reacts with liquid bromine to obtain a brominated compound, then the brominated compound is oxidized and cyclized to obtain 2-bromo-4H-cyclopentaphenanthrene, and methyl iodide reacts with the brominated compound to obtain 2-bromo-4, 4-dimethylcyclopentaphenanthrene. 2-bromo-4, 4-dimethylcyclopentaphenanthrene (12.6g, 42.4mmol) was charged into a three-necked flask, THF (100 mL) was added and stirred at-78 ℃ for 30 minutes under nitrogen protection, then 21mL of n-butyllithium (2.5M) was added and reacted for 1 hour, 7g of triisopropyl borate was further added and reacted for 1 hour at low temperature, and the temperature was gradually returned to room temperature. After-treatment, 2M hydrochloric acid was added to the system to adjust the pH of the solution to 4-5, the mixture was allowed to stand for liquid separation, the aqueous layer was extracted with ethyl acetate, and the organic layers were combined and spin-dried to obtain intermediate ET63-1(8.3g, 75%).
Step 2: tetrakistriphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) were added to a solution of intermediate ET63-1(100.6g, 384mmol) and compound d (57.6g, 183mmol) in degassed tetrahydrofuran (500mL), and the mixture was heated at reflux for 4 h. Suction filtration while hot gave a large amount of solid, which was dissolved in a solvent, followed by concentration and column chromatography on silica gel to give compound ET63(74.5g, 60%). Mass spectrum m/z: 679.19 (calculated value: 679.26). Theoretical element content (%) C49H33N3O: c, 86.57; h, 4.89; n, 6.18; o, 2.35. Measured elemental content (%): c, 86.50; h, 4.89; n, 6.16; o, 2.35. The above results confirmed that the obtained product was the objective product.
EXAMPLE 32 Synthesis of Compound ET77
Step 1: 2-bromo-9, 9-spirobifluorene (16.7g, 42.4mmol) was charged into a three-necked flask, and 100mL of THF was added under nitrogen protection, and stirred at-78 ℃ for 30 minutes, then 21mL of n-butyllithium (2.5M) was added, and the mixture was reacted for 1 hour, and 7g of triisopropyl borate was further added, and the reaction was carried out at low temperature for 1 hour, and then the temperature was gradually returned to room temperature. And in the post-treatment process, 2M hydrochloric acid is added into the system to ensure that the pH value of the solution is 4-5, standing and liquid separation are carried out, a water layer is extracted by ethyl acetate, organic layers are combined and spin-dried to obtain 2-boric acid-9, 9-spirobifluorene (12.2g, 80%).
Step 2: tetrakistriphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) were added to a solution of 2-boronic acid-9, 9-spirobifluorene (65.8g, 183mmol) and 2-chloro-4- (biphenyl-4-yl) -6-phenyl-1, 3, 5-triazine (63.6g, 185mmol) in degassed tetrahydrofuran (500mL) and the mixture was heated at reflux for 4 h. Suction filtration while hot gave a large amount of solid, which was dissolved in a solvent, followed by concentration and column chromatography on silica gel to give compound ET77(71.8g, 60%). Mass spectrum m/z: 623.18 (calculated value: 623.24). Theory of the inventionElement content (%) C46H29N3: c, 88.58; h, 4.69; n, 6.74. Measured elemental content (%): c, 88.55; h, 4.69; and N, 6.76. The above results confirmed that the obtained product was the objective product.
Comparative device example:
the ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, after the cleaning of the distilled water is finished, solvents such as isopropanol, acetone, methanol and the like are sequentially subjected to ultrasonic cleaning and then dried, the substrate is transferred into a plasma cleaning machine, the substrate is cleaned for 5 minutes, and the substrate is sent to an evaporation machine.
On the prepared ITO transparent electrode, layer by layer: hole injection layer 2-TNATA/60nm, hole transport layer compound NPB/30nm, evaporation host ADN: BDAVBi 2% doped mixed/30 nm, electron transport layer Alq330nm, electron injection layer LiF/1nm, cathode Al/300 nm.
Device examples 1-8:
the materials in the hole transport layer and the electron transport layer in the comparative device example were replaced as shown in table 1 below.
Device examples 9 to 16
The ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, after the cleaning of the distilled water is finished, solvents such as isopropanol, acetone, methanol and the like are sequentially subjected to ultrasonic cleaning and then dried, the substrate is transferred into a plasma cleaning machine, the substrate is cleaned for 5 minutes, and the substrate is sent to an evaporation machine.
On the prepared ITO transparent electrode, layer by layer: hole injection layer 2-TNATA/60nm, hole transport layer compound NPB/30nm, luminescence auxiliary layer compound/20 nm, evaporation host ADN: doping BDAVBi 2% and mixing the materials at 30nm, electron transport layer compounds at 30nm, electron injection layer LiF at 1nm and cathode Al at 300 nm.
Device examples 17 to 24
The ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, after the cleaning of the distilled water is finished, solvents such as isopropanol, acetone, methanol and the like are sequentially subjected to ultrasonic cleaning and then dried, the substrate is transferred into a plasma cleaning machine, the substrate is cleaned for 5 minutes, and the substrate is sent to an evaporation machine.
Evaporating a hole injection layer 2-TNATA/60nm, a hole transport layer/30 nm, a luminescence auxiliary layer compound/20 nm and an evaporation main body ADN on the prepared ITO transparent electrode layer by layer: doping BDAVBi 2% and mixing the materials at 30nm, forming an electron transport layer at 30nm, forming an electron injection layer LiF at 1nm and forming a cathode Al at 300 nm.
The results of the light emitting characteristic tests of the light emitting devices prepared in the comparative device example of the present invention and the device examples 1 to 24 are shown in table 1.
[ TABLE 1 ]
The above results show that, by combining the compounds represented by the chemical formulas (i) and (ii) of the present invention, the organic electroluminescent device having different hole transport layers, light-emitting auxiliary layers, and electron transport layers is designed, and under the combined action of the corresponding hole transport layer and/or light-emitting auxiliary layer, and electron transport layer, the injection, transport, and recombination in the light-emitting layer of carriers are effectively improved, the light-emitting efficiency of the organic electroluminescent device of the present invention is effectively improved, and the injection of carriers in the light-emitting layer is balanced, thereby avoiding energy accumulation and non-radiative energy dissipation on the electron transport layer side, and thus effectively improving the service life of the device. The organic electroluminescent device provided by the invention has the advantages of low starting voltage, high luminous efficiency and long service life, and the compound for preparing the organic electroluminescent device provided by the invention has the advantages of easily available raw materials, simple synthesis method and easy operation, and meets the requirements of industry and market to a great extent.
It is obvious that the above description of the embodiments is only intended to assist the understanding of the method of the invention and its core ideas. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.
Claims (1)
1. An organic electroluminescent device, comprising a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer comprises a hole transport layer, a light-emitting auxiliary layer and an electron transport layer, and the hole transport layer and the light-emitting auxiliary layer contain a compound represented by formula (I):
wherein L is1、L2Selected from single bonds, L3Selected from single bonds or phenyl; ar (Ar)1Selected from 9, 9-dimethylfluorenyl; ar (Ar)2One selected from the following groups;
Ar3one selected from the following groups;
wherein the electron transport layer contains a compound represented by the formula (II):
wherein Ar is4Selected from phenyl, naphthylOr dibenzothienyl; ar (Ar)5、Ar6Independently selected from one of the following groups:
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