CN110894203A - Organic light-emitting compound, application thereof and organic electroluminescent device - Google Patents

Organic light-emitting compound, application thereof and organic electroluminescent device Download PDF

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CN110894203A
CN110894203A CN201811069329.8A CN201811069329A CN110894203A CN 110894203 A CN110894203 A CN 110894203A CN 201811069329 A CN201811069329 A CN 201811069329A CN 110894203 A CN110894203 A CN 110894203A
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indolyl
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吕瑶
冯美娟
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Green People's Science And Technology Ltd Co In Beijing
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Abstract

The invention relates to the field of organic electroluminescent devices, and discloses an organic luminescent compound, application thereof and an organic electroluminescent device, wherein the compound has a structure shown in a formula (I). The organic luminescent compound provided by the invention can regulate and control the HOMO energy level and LUMO energy level of an organic electroluminescent material, and simultaneously, the organic electroluminescent material containing the organic luminescent compound has higher fluorescence quantum yield, so that the luminous efficiency of the organic electroluminescent material is improved, the service life of the material is prolonged, and the organic luminescent compound provided by the invention can emit blue light when being used in an organic electroluminescent device.

Description

Organic light-emitting compound, application thereof and organic electroluminescent device
Technical Field
The invention relates to the field of organic electroluminescent devices, in particular to an organic luminescent compound, application of the organic luminescent compound in an organic electroluminescent device, and an organic electroluminescent device containing one or more than two compounds in the organic luminescent compound.
Background
Compared with the traditional liquid crystal technology, the organic electroluminescence (OLED) technology does not need backlight source irradiation and a color filter, pixels can emit light to be displayed on a color display panel, and the OLED technology has the characteristics of ultrahigh contrast, ultra-wide visual angle, curved surface, thinness and the like.
Organic electroluminescence mainly utilizes the phenomenon that organic substances convert electric energy into light energy, an organic light-emitting element generally comprises a cathode and an anode and an organic layer structure between the cathode and the anode, and the organic layer generally comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer and an electron injection layer. When a voltage is applied to the anode and the cathode, holes are injected from the anode side to the light-emitting layer, electrons are injected from the cathode side to the light-emitting layer, the injected holes and electrons combine in the light-emitting layer to form excitons, and the excitons emit light when returning to the ground state, wherein 25% of excited states return to the ground state through singlet excited states, and the emitted light is called fluorescence; 75% returns to the ground state through the triplet excited state, and the emitted light is called phosphorescence. The singlet excited state forms a triplet excited state by down-conversion, and if phosphorescence is used, the light emission efficiency can theoretically reach 100%.
Materials used as an organic layer in an organic electroluminescent device can be classified into a luminescent material and a charge transport material according to functions, the luminescent material can be classified into a fluorescent material and a phosphorescent material, a host-guest doping system can be used as the luminescent material, and the guest material receives energy of the host material to emit light; the charge transport material may be classified into a hole injection material, a hole transport material, an electron blocking material, an electron transport material, and an electron injection material.
The currently used materials for forming the layers of the OLED still have the defects of high driving voltage, short service life, low current efficiency and low brightness, especially the defects of efficiency and life of the blue organic electroluminescent material.
Disclosure of Invention
The present invention aims to overcome the above-mentioned defects of the prior art, and provides an organic compound capable of adjusting and controlling the HOMO level and the LUMO level of an organic electroluminescent material, and at the same time, the organic electroluminescent material containing the organic compound has a high fluorescence quantum yield, thereby improving the luminous efficiency and reducing the driving voltage.
The inventor of the present invention finds, in research, that the organic light emitting compound having the structure shown in formula (I) provided by the present invention has a good thermodynamic stability, a high glass transition temperature, a good film forming property, a suitable energy gap when used as an organic electroluminescent material, through the presence of triphenyl silicon and pyrene structure and B element, and can significantly improve light emitting efficiency and prolong the service life of the material. Accordingly, the inventors have completed the technical solution of the present invention.
In order to achieve the above object, a first aspect of the present invention provides an organic light emitting compound having a structure represented by formula (I),
Figure BDA0001799117730000021
wherein, in the formula (I),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or L1And L2Each independently is absent;
R1、R2and R3Each independently selected from H and C1-12Alkyl groups of (a);
R4and R5Each independently selected from H, C1-12Alkyl, substituted or unsubstituted phenyl of (a);
R6and R7Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted monocyclic radical with or without heteroatoms selected from O, S, N and B, a substituted or unsubstituted bicyclic radical with or without heteroatoms selected from O, S and N, or a monocyclic radical with or without heteroatoms selected from O, S and NA substituted or unsubstituted tricyclic group of a subgroup;
L1、L2、R4、R5、R6and R7Wherein the substituents are each independently selected from C1-12Alkyl group of (A), phenyl group, biphenyl group, cyano group, fluorine atom, C substituted by 1 to 3 fluorine atoms1-12And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
A second aspect of the present invention provides the use of an organic light-emitting compound as described in the first aspect above in an organic electroluminescent device.
A third aspect of the present invention provides an organic electroluminescent device comprising one or two or more of the organic light-emitting compounds according to the first aspect.
The organic luminescent compound provided by the invention can regulate and control the HOMO energy level and LUMO energy level of an organic electroluminescent material, and simultaneously, the organic electroluminescent material containing the organic luminescent compound has higher fluorescence quantum yield, so that the luminous efficiency of the organic electroluminescent material is improved, the service life of the material is prolonged, and the organic luminescent compound provided by the invention can emit blue light when being used in an organic electroluminescent device.
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
As described above, the first aspect of the present invention provides an organic light-emitting compound having a structure represented by formula (I),
Figure BDA0001799117730000041
wherein, in the formula (I),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or L1And L2Each independently is absent;
R1、R2and R3Each independently selected from H and C1-12Alkyl groups of (a);
R4and R5Each independently selected from H, C1-12Alkyl, substituted or unsubstituted phenyl of (a);
R6and R7Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted monocyclic group with or without heteroatoms selected from O, S, N and B, a substituted or unsubstituted bicyclic group with or without heteroatoms selected from O, S and N, or a substituted or unsubstituted tricyclic group with or without heteroatoms selected from O, S and N;
L1、L2、R4、R5、R6and R7Wherein the substituents are each independently selected from C1-12Alkyl group of (A), phenyl group, biphenyl group, cyano group, fluorine atom, C substituted by 1 to 3 fluorine atoms1-12And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
“C1-12The "alkyl group" of (a) represents an alkyl group having 1 to 12 carbon atoms in total, and may be, for example, an alkyl group having 1,2,3, 4,5, 6, 7, 8, 9, 10, 11 and 12 carbon atoms in total, respectively, and is directed to "C1-8Alkyl of and C1-6The term "alkyl" has similar definitions, and the present invention is not repeated in detail, and those skilled in the art should not be construed as limiting the present invention.
“L1And L2Each independently absent represents L1And L2May be a non-substituent but only a chemical bond such that the B atom in formula (I) is directly bonded to the pyrene structure and/or the Si atom in formula (I) is directly bonded to the pyrene structure.
When the group referred to in the present invention is an indolyl group, it is preferred that the pyrrole group in the bicyclic structure of the indolyl group is attached to the corresponding position.
When the group referred to in the present invention is a phenyl-substituted indolyl group, it is preferred that the pyrrole group in the bicyclic structure of the indolyl group is attached to the corresponding position.
In the related groups "substituted or unsubstituted" in the present invention, if the group is a substituted group, the substituent may be at any position of the corresponding group which can be substituted, unless otherwise specified.
According to a preferred embodiment of the method according to the invention,
in the formula (I), the compound represented by the formula (I),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or L1And L2Each independently is absent;
R1、R2and R3Each independently selected from H and C1-8Alkyl groups of (a);
R4and R5Each independently selected from H, C1-8Alkyl, substituted or unsubstituted phenyl of (a);
R6and R7Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted monocyclic radical containing or not containing a heteroatom selected from O, S and B, containing or not containing a heteroatom selected from O, S and BA substituted or unsubstituted bicyclic group or a substituted or unsubstituted tricyclic group with or without a heteroatom selected from O, S and B;
L1、L2、R4、R5、R6and R7Wherein the substituents are each independently selected from C1-8Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms1-8And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
Provided below is R6And R7Several preferred embodiments of (a):
embodiment mode 1:
in the formula (I), R6And R7Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted monocyclic group containing an O atom, wherein the unsubstituted monocyclic group containing an O atom is represented by the following structure:
Figure BDA0001799117730000061
and R is6And R7Wherein the substituents are each independently selected from C1-6Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms1-6And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
Embodiment mode 2:
in the formula (I), R6And R7Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted fluorenylSubstituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted monocyclic group containing an O atom, wherein the unsubstituted monocyclic group containing an O atom is represented by the following structure:
Figure BDA0001799117730000062
and R is6And R7Wherein the substituents are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, phenyl, biphenyl, cyano, fluoro, C substituted with 1-3 fluorine atoms1-6And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
In embodiments 1 and 2, when R6And R7When a substituted monocyclic group containing an O atom is formed together with the B atom in the formula (I), the substituent may be substituted at an arbitrary position of the monocyclic group which may be substituted.
Embodiment mode 3:
in the formula (I), R6And R7Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted bicyclic group containing an O atom, wherein the unsubstituted bicyclic group containing an O atom is represented by the following structure:
Figure BDA0001799117730000071
and R is6And R7Wherein the substituents are each independently selected from C1-6Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms1-6And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
Embodiment 4:
in the formula (I), R6And R7Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted bicyclic group containing an O atom, wherein the unsubstituted bicyclic group containing an O atom is represented by the following structure:
Figure BDA0001799117730000081
and R is6And R7Wherein the substituents are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, phenyl, biphenyl, cyano, fluoro, C substituted with 1-3 fluorine atoms1-6And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
In embodiments 3 and 4, when R6And R7When a substituted bicyclic group containing an O atom is formed together with the B atom in the formula (I), the substituent may be substituted at any position of the bicyclic group which may be substituted.
Embodiment 5:
in the formula (I), R6And R7Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted fluorenylSubstituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted tricyclic group with or without a heteroatom selected from O, S and B, wherein the unsubstituted tricyclic group with or without a heteroatom selected from O, S and B is represented by any one of the following structures:
Figure BDA0001799117730000082
and in the structure shown as a2, X is O, S, CH2Or BH;
and R6And R7Wherein the substituents are each independently selected from C1-6Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms1-6And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
Embodiment 6:
in the formula (I), R6And R7Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted tricyclic group with or without a heteroatom selected from O, S and B, wherein the unsubstituted tricyclic group with or without a heteroatom selected from O, S and B is represented by any one of the following structures:
Figure BDA0001799117730000091
and in the structure shown as a2, X is O, S, CH2Or BH；
And R is6And R7Wherein the substituents are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, phenyl, biphenyl, cyano, fluoro, C substituted with 1-3 fluorine atoms1-6And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
In embodiments 5 and 6, when R6And R7When a substituted tricyclic group containing or not containing a heteroatom selected from the group consisting of O, S and B is formed together with the B atom in the formula (I), the substituent may be substituted at any position of the tricyclic group which may be substituted.
And, in the embodiments 5 and 6, when R6And R7And B atom in formula (I) together form a substituted tricyclic group which may or may not contain a heteroatom selected from O, S and B, and when X in the structure represented by a2 is C or B, H present on X may be substituted with at least one of the substituents defined above, for example, when X is C or B, H present on X may be substituted with a group such as methyl, ethyl, isopropyl, tert-butyl, phenyl, etc.
Preferably, in the aforementioned embodiments 1 to 6 of the present invention,
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or L1And L2Each independently is absent;
R1、R2and R3Each independently selected from H and C1-8Alkyl groups of (a);
R4and R5Each independently selected from H, C1-8Alkyl, substituted or unsubstituted phenyl.
According to another preferred embodiment, the organic light-emitting compound of the present invention is selected from at least one of the specific compounds listed in claim 6.
In order to further improve the luminous efficiency of the organic electroluminescent material containing the present invention, according to another preferred embodiment, the organic luminescent compound of the present invention is selected from at least one of the specific compounds listed in claim 7.
The synthesis method of the organic light-emitting compound provided by the present invention is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the structural formula of the organic light-emitting compound provided by the present invention in combination with the preparation method of the preparation example.
Further, some preparation methods of the organic light emitting compound are exemplarily given in the preparation examples of the present invention, and those skilled in the art can obtain the organic light emitting compound provided by the present invention according to the preparation methods of these exemplary preparation examples. The present invention will not be described in detail herein with respect to specific methods of preparing the various compounds of the present invention, which should not be construed as limiting the invention to those skilled in the art.
As described above, the second aspect of the present invention provides the use of the organic light-emitting compound described in the first aspect in an organic electroluminescent device.
As described above, the third aspect of the present invention provides an organic electroluminescent device comprising the organic luminescent compound according to the first aspect.
Preferably, the organic light emitting compound is present in at least one of an electron transport layer, a light emitting layer and a hole transport layer of the organic electroluminescent device.
Preferably, the organic light emitting compound is present in a light emitting layer of the organic electroluminescent device.
More preferably, the organic light-emitting compound is present in a light-emitting layer of the organic electroluminescent device and serves as a guest material of the light-emitting layer.
According to the present invention, other materials may be further contained in the light emitting layer, and in the present invention, the other materials may be compounds that generate emission via at least one of phosphorescence, fluorescence, Thermally Activated Delayed Fluorescence (TADF), metal-to-ligand charge transfer (MLCT), a hybrid CT state (HLCT), and a triplet-triplet annihilation method.
Preferably, the light-emitting layer further contains one or more of anthracene derivatives, carbazole derivatives, fluorene derivatives, arylamine derivatives, organosilicon derivatives, carbazole-triazine derivatives, phosphoxy derivatives, perylene derivatives, distyrylaryl derivatives, organoboron derivatives, acridine derivatives, ketone-containing derivatives, sulfone-based derivatives, cyano derivatives, and xanthene derivatives.
Wherein the anthracene derivative has a structure represented by formula (II):
Figure BDA0001799117730000111
wherein, in the formula (II),
R11、R12and R13May be the same or different and are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenylnaphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine.
Wherein the phosphorus oxy derivative has a general formula shown in formula (III):
Figure BDA0001799117730000112
wherein, in the formula (III),
R14、R15and R16May be the same or different and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl, benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenylnaphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazineOxazine, pyridazine or triazine.
Wherein the sulfone derivative has a structure represented by formula (IV):
Figure BDA0001799117730000121
wherein the ketone derivative has a structure represented by formula (V):
Figure BDA0001799117730000122
wherein R is17、R18、R19And R20May be the same or different and are each independently selected from the group consisting of a single bond, hydrogen, deuterium, substituted or unsubstituted alkyl, benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenylnaphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine.
According to the present invention, the organic electroluminescent device preferably includes a substrate, an anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an optional electron blocking layer, an emission layer (EML), an optional hole blocking layer, an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and a cathode, which are sequentially stacked.
Preferably, the thickness of the light-emitting layer is 100-1000 angstroms, and more preferably 150-400 angstroms.
Preferably, the organic electroluminescent device may further include a first cover layer and/or a second cover layer, wherein the first cover layer is disposed on an outer surface of the anode, and the second cover layer is disposed on an outer surface of the cathode.
For example, the organic electroluminescent device may be sequentially stacked with a first capping layer, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode, and a second capping layer.
Preferably, the first cover layer and the second cover layer each independently contain one or more organic light-emitting compounds described in any one of the above.
According to the present invention, the substrate may use a glass substrate, a plastic substrate, or a metal substrate.
Preferably, the anode material forming the anode may be selected from one or more of indium tin oxide, indium zinc oxide, and tin dioxide; the thickness of the anode active layer (anode) formed by the anode material can be, for example, 100-1700 angstroms.
Preferably, the material forming the hole injection layer may be a hole injection material, and the material forming the hole transport layer may be a hole transport material, and the hole injection material and the hole transport material may each be independently selected from aromatic amine derivatives (e.g., NPB, SqMA1), hexaazatriphenylene derivatives (e.g., HACTN), indolocarbazole derivatives, conductive polymers (e.g., PEDOT/PSS), phthalocyanine or porphyrin derivatives, dibenzoindenofluorenamine, or spirobifluorenylamine.
The hole injection layer and the hole transport layer have any one of structures represented by formulas (VI) to (IX):
Figure BDA0001799117730000131
wherein, in formulae (VI) to (IX):
R′1to R'9The groups of (a) may be the same or different and are each independently selected from a single bond, hydrogen, deuterium, substituted or unsubstituted alkyl, benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, dimethylfluorene, spirobifluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine.
Preferably, the hole injection layer has a thickness of 100-2000 angstroms, more preferably 200-600 angstroms.
Preferably, the hole transport layer has a thickness of 100-1000 angstroms, more preferably 200-400 angstroms.
Preferably, the material forming the electron transport layer can also be selected from at least one of a metal complex, a benzimidazole derivative, a pyrimidine derivative, a pyridine derivative, a quinoline derivative, and a quinoxaline derivative; preferably, the thickness of the electron transport layer is 100-600 angstroms.
The material for forming the electron blocking layer is not particularly limited, and in general, any compound capable of satisfying the following conditions can be considered:
(1) the luminescent layer has a higher LUMO energy level, and the purpose of the luminescent layer is to reduce the number of electrons leaving the luminescent layer, so that the recombination probability of the electrons and holes in the luminescent layer is improved.
(2) The light emitting layer has larger triplet energy, and the purpose of the light emitting layer is to reduce the number of excitons which leave the light emitting layer, thereby improving the efficiency of exciton conversion and light emission.
Materials forming the electron blocking layer include, but are not limited to, aromatic amine derivatives (e.g., NPB), spirobifluorene amines (e.g., SpMA2), in which a portion of the electron blocking material is similar in structure to the hole injecting material and the hole transporting material.
Preferably, the electron blocking layer has a thickness of 50 to 600 angstroms.
The material for forming the hole blocking layer is preferably a compound having the following conditions:
(1) the organic electroluminescent device has a higher HOMO energy level, and the purpose of the organic electroluminescent device is to reduce the number of holes leaving a light-emitting layer, so that the recombination probability of electrons and holes in the light-emitting layer is improved.
(2) The light emitting layer has larger triplet energy, and the purpose of the light emitting layer is to reduce the number of excitons which leave the light emitting layer, thereby improving the efficiency of exciton conversion and light emission.
The material forming the hole blocking layer may further contain, for example, one or more of phenanthroline derivatives (e.g., Bphen, BCP), triphenylene derivatives, and benzimidazole derivatives.
Preferably, the hole blocking layer has a thickness of 50 to 600 angstroms.
Preferably, the material of the electron injection layer can be LiF or Al2O3And MnO or a plurality of MnO.
Preferably, the electron injection layer has a thickness of 1 to 50 angstroms.
Preferably, the cathode material may be one or more of Al, Mg, and Ag.
Preferably, the cathode layer has a thickness of 800-.
According to the present invention, the method for manufacturing the organic electroluminescent device may specifically adopt any one of the following methods.
The organic electroluminescent device of the invention is preferably coated in one layer or in a plurality of layers by means of a sublimation process. In this case, in the vacuum sublimation system, the temperature is less than 10 DEG-3Pa, preferably less than 10-6The organic light-emitting compound provided by the present invention is applied by vapor deposition at an initial pressure of Pa.
The organic electroluminescent device of the invention is preferably coated with one layer or a plurality of layers by an organic vapor deposition method or sublimation with the aid of a carrier gas. In this case, 10-6The organic light-emitting compound provided by the present invention is applied under a pressure of Pa to 100 Pa. A particular example of such a process is an organic vapor deposition jet printing process in which the organic light-emitting compounds provided by the present invention are applied directly through a nozzle and form an organic electroluminescent device.
The organic electroluminescent device of the present invention is preferably formed into a one-layer or multi-layer structure by photo-induced thermal imaging or thermal transfer.
The organic electroluminescent device of the present invention preferably comprises the organic luminescent compound of the present invention formulated as a solution, formed into a layer or a plurality of layers by spin coating or by any printing means, such as screen printing, flexographic printing, ink jet printing or offset printing, more preferably by ink jet printing. However, when a plurality of layers are formed by this method, the layers are easily damaged, that is, when one layer is formed and another layer is formed by using a solution, the formed layer is damaged by a solvent in the solution, which is not favorable for manufacturing a device. The organic luminescent compound provided by the invention can be substituted by structural modification, so that the organic luminescent compound provided by the invention can generate a crosslinking effect under the condition of heating or ultraviolet exposure, and a complete layer can be kept without being damaged. The organic light-emitting compounds according to the invention can additionally be applied from solution and fixed in the respective layer by subsequent crosslinking in the polymer network.
Preferably, the organic electroluminescent device of the invention is manufactured by applying one or more layers from a solution and one or more layers by a sublimation method.
The solvent for the preparation of the organic electroluminescent element of the present invention is preferably selected from the group consisting of toluene, anisole, o-xylene, m-xylene, p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, THF, methyl-THF, THP, chlorobenzene, phenoxytoluene, particularly 3-phenoxytoluene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, benzothiazole, butyl benzoate, isopropanol, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, One or more of methyl benzoate, NMP, p-methylisobenzene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dibutyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1-bis (3, 4-dimethylphenyl) ethane, 2-heptanol, and 3-heptanol.
Preferably, in the preparation of the organic electroluminescent device of the present invention, the organic luminescent compound of the present invention and other compounds are sufficiently mixed and then a layer or layers are formed by the above application method. More preferably, in the vacuum sublimation system, less than 10-3Pa, preferably less than 10-6Pa, by applying the respective compounds by vapour depositionForming one or more layers.
The technical solution of the present invention is described in detail by specific examples below.
The various starting materials used in the present invention are commercially available unless otherwise specified.
Preparation example 1: compound 1-1
Figure BDA0001799117730000171
Synthesis of intermediate 1-1-1-1: dissolving 0.1mol of 1, 6-dibromopyrene in 360ml of dioxane solvent, sequentially adding 0.1mol of p-isopropylphenylboronic acid, 0.25mol of K2CO3 and 0.001mol of ferrocene palladium dichloride under the protection of nitrogen, heating to reflux reaction, detecting basic reaction of raw materials by HPLC after 4 hours, decompressing and spin-drying reaction liquid, and performing column chromatography on residues to obtain an intermediate 1-1-1-1. (yield: 75%)
Synthesis of intermediate 1-1-1-2: 0.075mol of intermediate 1-1-1-1 is added to 330ml of chloroform and stirred, the temperature is kept constant at 0 ℃, 0.075mol of benzyltrimethylammonium tribromide is gradually added in portions, and after the reaction is finished, the temperature is raised to room temperature again. After 12h, the reaction of the raw materials is detected to be finished, the reaction solution is concentrated and steamed in a rotary mode, and then the intermediate 1-1-1-2 is obtained through column chromatography (yield is 72%).
Synthesis of intermediate 1-1-1-3: the synthesis method was the same as the synthesis of intermediate 1-1-1-1 to obtain intermediate 1-1-1-3 (yield 74%).
Synthesis of intermediate 1-1-1-4: 0.040mol of the intermediate 1-1-1-3 is added into 380ml of DMF, stirred and kept at 60 ℃, 0.040mol of DMF solution of NBS is added dropwise, and the temperature is raised to 85 ℃ again after the dropwise addition. After 5h, the reaction of the raw materials is detected to be finished, 500ml of water is dripped into the reaction liquid, a large amount of solid is separated out, the mixture is stirred for half an hour and filtered, and the residue is subjected to column chromatography to obtain the intermediate 1-1-1-4 (the yield is 48%).
Synthesis of Compound 1-1-1: adding 0.0019mol of bromodiphenylborane into 20ml of tetrahydrofuran, adding 0.019mol of magnesium chips, heating to reflux, dropwise adding a small amount of 1, 2-dibromoethane to initiate reaction, and continuously adding the remaining 0.0171mol of bromodiphenylborane to prepare the Grignard reagent. 0.019mol of the intermediate 1-1-1-4 is added into 100ml of anhydrous tetrahydrofuran, the temperature is controlled to-78 ℃, 0.019mol of N-butyllithium is dropwise added under the protection of N2, and the mixture is heated to room temperature and stirred for 2 hours. Cooling the reaction solution to-78 ℃, dropwise adding the prepared Grignard reagent, heating to room temperature, continuing the reaction for 5 hours, quenching the reaction by using dilute acid solution after the reaction is finished, spin-drying the organic phase, and passing through a chromatographic column to obtain the compound 1-1-1 (the yield is 41%).
Calcd for C70H57 Bsi: 937.10 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.20-1.21 (12H, d), 2.87-2.88 (2H, m), 7.36-7.55 (31H, m), 7.70-7.75 (8H, m), 7.88-7.89 (2H, m), 8.00-8.01 (1H, s), 8.30-8.30 (1H, s).
Preparation example 2: compounds 1-1-14
Figure BDA0001799117730000181
Synthesis of Compounds 1-1-14: adding 0.01mol of bis (trimethylphenyl) boron fluoride into 20ml of tetrahydrofuran, adding 0.01mol of magnesium chips, heating to reflux, dropwise adding a small amount of 1, 2-dibromoethane to initiate reaction, and continuously adding the rest 0.09mol of bis (trimethylphenyl) boron fluoride to prepare the Grignard reagent. 0.1mol of the intermediate 1-1-1-4 is added into 100ml of anhydrous tetrahydrofuran, the temperature is controlled to-78 ℃, 0.1mol of N-butyllithium is dropwise added under the protection of N2, and the mixture is heated to room temperature and stirred for 2 hours. Cooling the reaction solution to-78 ℃, dropwise adding the prepared Grignard reagent, heating to room temperature, continuing the reaction for 5 hours, quenching the reaction by using dilute acid solution after the reaction is finished, spin-drying the organic phase, and passing through a chromatographic column to obtain the compound 1-1-14 (yield is 53%).
Calcd for C76H69 Bsi: 1021.26 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.20-1.21 (12H, d), 2.34-2.35 (18H, m), 2.87-2.88 (2H, m), 6.91-6.91 (4H, s), 7.36-7.37 (14H, m), 7.46-7.55 (11H, m), 7.70-7.71 (4H, m), 7.89-7.90 (2H, m), 8.00-8.01 (1H, s), 8.30-8.30 (1H, s).
Preparation example 3: compounds 1-1-39
Figure BDA0001799117730000191
Synthesis of intermediate 1-1-39-1: preparing a Grignard reagent, adding 0.01mol of 3-bromodibenzofuran and 0.4mol of magnesium into 30ml of tetrahydrofuran, heating to initiate a reflux reaction, slowly dropping the rest 0.09mol of tetrahydrofuran saturated solution of the 3-bromodibenzofuran, preserving heat and refluxing for about 1h, protecting nitrogen, then cooling to 0 ℃, slowly dropping 0.05mol of boron trifluoride diethyl etherate solution, stirring for 30min after dropping, slowly heating to reflux, detecting that the reaction of raw materials is finished after 2h, adding n-hexane into reaction liquid for extraction, taking organic phase, performing pressure spin drying on the organic phase, and performing column chromatography on the residue to obtain an intermediate 1-1-39-1 (yield 51%).
Synthesis of intermediate 1-1-39-2: dissolving 0.1mol of intermediate 1-1-1-4 in 900ml of 1, 4-dioxane solvent, introducing nitrogen, stirring, sequentially adding 0.1mol of pinacol diboron, 0.25mol of potassium acetate and 0.001mol of ferrocene palladium dichloride, heating to reflux reaction, detecting basic reaction of raw materials by HPLC after 4 hours, decompressing and spin-drying reaction liquid, and carrying out column chromatography on residues to obtain the intermediate 1-1-39-2 (the yield is 40%).
Synthesis of Compounds 1-1-39: dissolving 0.04mol of intermediate 1-1-39-2 in 360ml of dioxane solvent, sequentially adding 0.04mol of intermediate 1-1-39-1, 0.1mol of K2CO3 and 0.0004mol of ferrocene palladium dichloride under the protection of nitrogen, heating to reflux reaction, after 4h, detecting basic reaction of raw materials by HPLC, decompressing and spin-drying reaction liquid, and performing column chromatography on residues to obtain an intermediate compound 1-1-39. (yield 50%)
Calcd for C82H61BO2 Si: 1117.26 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.20-1.20 (12H, d), 2.87-2.88 (2H, m), 7.32-7.55 (31H, m), 7.66-7.70 (8H, m), 7.80-7.81 (2H, m), 7.89-7.90 (4H, m), 8.0-8.0 (1H, s), 8.3-8.3 (1H, s).
Preparation example 4: compounds 1-1-54
Figure BDA0001799117730000201
Synthesis of Compounds 1-1-54: adding 0.0019mol of su1 into 20ml of tetrahydrofuran, adding 0.019mol of magnesium chips, heating to reflux, dropwise adding a small amount of 1, 2-dibromoethane to initiate reaction, and continuously adding the rest 0.0171mol of su1 to prepare the Grignard reagent. 0.019mol of the intermediate 1-1-1-4 is added into 100ml of anhydrous tetrahydrofuran, the temperature is controlled to-78 ℃, 0.019mol of N-butyllithium is dropwise added under the protection of N2, and the mixture is heated to room temperature and stirred for 2 hours. Cooling the reaction solution to-78 ℃, dropwise adding the prepared Grignard reagent, heating to room temperature, continuing the reaction for 5 hours, quenching the reaction by using dilute acid solution after the reaction is finished, spin-drying the organic phase, and passing through a chromatographic column to obtain the compound 1-1-54 (the yield is 41%).
Calcd for C70H55 BOSi: 951.08 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.20-1.21 (12H, d), 2.87-2.88 (2H, m), 7.14-7.17 (4H, m), 7.36-7.55 (27H, m), 7.70-7.71 (6H, m), 7.88-7.89 (2H, m), 8.20-8.21 (1H, s), 8.29-8.30 (1H, s).
Preparation example 5: compounds 1-1-70
Figure BDA0001799117730000211
Synthesis of intermediate 1-1-70-1: preparing a Grignard reagent, adding 0.01mol of bis (trimethylphenyl) boron fluoride and 0.4mol of magnesium into 30ml of tetrahydrofuran, heating until the reflux reaction is initiated, slowly dripping the residual 0.09mol of tetrahydrofuran saturated solution of bis (trimethylphenyl) boron fluoride, preserving the temperature and refluxing for about 1h, and keeping the solution under the protection of nitrogen for later use. Adding 0.1mol of p-bromofluorobenzene and tetrahydrofuran into another three-necked bottle, uniformly stirring, carrying out nitrogen protection, cooling to-5 ℃, transferring the prepared Grignard reagent into a dropping funnel, slowly dropwise adding, keeping the temperature of the system not to exceed 10 ℃, stirring for 30min after dropwise adding, slowly raising the temperature to room temperature, detecting that the reaction of the raw materials is finished after 5h, dropwise adding a saturated ammonium chloride aqueous solution into the reaction liquid, stirring for 5min, adding dichloromethane for extraction, taking organic phase, carrying out pressure spin drying on the organic phase, and carrying out column chromatography on the residue to obtain an intermediate 1-1-70-1 (the yield is 45%).
Synthesis of Compounds 1-1-70: adding 0.004mol of the intermediate 1-1-70-1 into 20ml of tetrahydrofuran, adding 0.16mol of magnesium chips, heating to reflux, dropwise adding a small amount of 1, 2-dibromoethane to initiate reaction, continuously supplementing the rest 0.036mol of the intermediate 1-1-70-1 to prepare a Grignard reagent, adding 0.04mol of the intermediate 1-1-1-4 into 340ml of anhydrous tetrahydrofuran, controlling the temperature to be-78 ℃, dropwise adding 0.04mol of N-butyllithium under the protection of N2, heating to room temperature, and stirring for 2 hours. Cooling the reaction solution to-78 ℃, dropwise adding the prepared Grignard reagent, heating to room temperature, continuing the reaction for 5 hours, quenching the reaction by using dilute acid solution after the reaction is finished, spin-drying the organic phase, and passing through a chromatographic column to obtain the compound 1-1-70 (the yield is 40%).
Calcd for C82H73 Bsi: 1097.35 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.20-1.21 (12H, d), 2.34-2.34 (18H, s), 2.87-2.88 (2H, m), 6.91-6.91 (4H, s), 7.36-7.37 (14H, m), 7.46-7.55 (11H, m), 7.71-7.71 (4H, s), 7.79-7.81 (4H, m), 7.89-7.90 (2H, m), 8.26-8.26 (1H, s).
Preparation example 6: compounds 1-1-109
Figure BDA0001799117730000221
Synthesis of Compounds 1-1-109: dissolving 0.04mol of intermediate 1-1-39-2 in 360ml of dioxane solvent, sequentially adding 0.04mol of B-chlorophthalic diborane, 0.1mol of K2CO3 and 0.0004mol of ferrocene palladium dichloride under the protection of nitrogen, heating to reflux reaction, detecting basic reaction of raw materials by HPLC after 4 hours, decompressing and spin-drying reaction liquid, and performing column chromatography on residues to obtain intermediate compounds 1-1-109. (yield 65%)
Calcd for C64H51BO2 Si: 890.99 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.20-1.20 (12H, d), 2.87-2.88 (2H, m), 6.84-6.85 (4H, m), 7.36-7.55 (25H, m), 7.7-7.71 (4H, s), 7.89-7.90 (2H, m), 8.0-8.0 (1H, s), 8.3-8.3 (1H, s).
Preparation example 7: compounds 1-2-17
Figure BDA0001799117730000222
And (3) synthesizing an intermediate 1-2-17-1: preparing a Grignard reagent, adding 0.01mol of 3- (4-chlorphenyl) -pyridine and 0.4mol of magnesium into 30ml of tetrahydrofuran, heating to reflux, dropwise adding a small amount of 1, 2-dibromoethane to initiate reaction, slowly dropwise adding the rest 0.09mol of saturated tetrahydrofuran solution of 3- (4-chlorphenyl) -pyridine, preserving heat and refluxing for about 1h, protecting with nitrogen, then cooling to 0 ℃, slowly dropwise adding 0.05mol of boron trifluoride diethyl etherate solution, stirring for 30min after dropwise adding, then slowly heating to reflux, detecting the reaction of raw materials after 2h, extracting the reaction liquid by adding n-hexane, taking organic phase, performing pressure spin drying, and performing column chromatography on the residue to obtain an intermediate 1-2-17-1 (yield 51%).
Synthesis of Compounds 1-2-17: adding 0.005mol of intermediate 1-2-17-1 into 20ml of tetrahydrofuran, adding 0.16mol of magnesium chips, heating to reflux, dropwise adding a small amount of 1, 2-dibromoethane to initiate reaction, continuously supplementing the rest 0.045mol of intermediate 1-2-17-1 to prepare a Grignard reagent, adding 0.05mol of intermediate 1-1-1-4 into 450ml of anhydrous tetrahydrofuran, controlling the temperature to be-78 ℃, dropwise adding 0.05mol of N-butyllithium under the protection of N2, heating to room temperature, and stirring for 2 hours. Cooling the reaction solution to-78 ℃, dropwise adding a Grignard reagent, heating to room temperature, continuing the reaction for 5 hours, quenching the reaction by using a dilute acid solution after the reaction is finished, spin-drying an organic phase, and passing through a chromatographic column to obtain the compound 1-2-17 (the yield is 32%).
Calcd for C80H63BN2 Si: 1091.27 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.20-1.21 (12H, d), 2.87-2.88 (2H, m), 7.36-7.57 (27H, m), 7.70-7.71 (4H, s), 7.79-7.81 (8H, m), 7.89-7.90 (2H, m), 8.0-8.0 (1H, s), 8.3-8.3 (1H, s), 8.42-8.43 (2H, m), 8.7-8.7 (2H, m), 9.24-9.25 (2H, d).
Preparation example 8: compound 2-1
Figure BDA0001799117730000231
And (3) synthesizing an intermediate 2-1-1-1: 2.94mmol of 1, 6-diisopropylpyrene, 3.22mmol of benzyltrimethylammonium bromide and 60ml of chloroform were put into a 250ml three-necked flask and stirred at room temperature for 3 hours. After completion of the reaction, 100ml of water was added, and the organic layer was extracted with toluene. The organic layer was dried over anhydrous sodium sulfate and rotary evaporated to dryness to give the crude product. The crude product was purified by silica gel column to obtain intermediate 2-1-1-1 (yield 75%).
And (3) synthesizing an intermediate 2-1-1-2: adding the intermediate 2-1-1-110 mmol and anhydrous tetrahydrofuran 50ml into a 250ml three-necked bottle, cooling to-78 ℃ by liquid nitrogen under the protection of nitrogen, dropwise adding 6.3ml of 1.6M n-butyllithium/n-hexane solution (10mmol), stirring for 1.5 hours at-78 ℃ after dropwise adding, dropwise adding 10mmol of fluorobenzyl borane in 30ml of tetrahydrofuran solution, and continuing to react for 12 hours after dropwise adding. And adding 50ml of purified water dropwise for quenching, returning the temperature to room temperature, and extracting with ethyl acetate for 2 times. Ethyl acetate was collected, spin-dried, and the crude product was purified by silica gel column to give intermediate 2-1-1-2 (yield 72%).
And (3) synthesizing an intermediate 2-1-1-3: the intermediate 2-1-1-32.94mmol, benzyltrimethylammonium bromide 3.22mmol, and chloroform 60ml were put into a 250ml three-necked flask, and stirred at room temperature for 3 hours. After completion of the reaction, 100ml of water was added, and the organic layer was extracted with toluene. The organic layer was dried over anhydrous sodium sulfate and rotary evaporated to dryness to give the crude product. The crude product was purified by silica gel column to obtain intermediate 2-1-1-3 (yield 70%).
Synthesis of Compound 2-1-1: a250 ml three-necked flask was charged with intermediate 2-1-1-324.75mmol, 27.22mmol4- (triphenylsilyl) phenylboronic acid, 1.23mmol Pd (PPh)3)4，61.9mmol K2CO361.9mmol, purified water 10ml, 1-4-dioxane 120ml, nitrogen gas replacement 3 times, reflux 12 hours. After the reaction was completed, it was cooled to room temperature. The reaction mixture was rotary-evaporated to dryness, and 500ml of ethyl acetate was dissolved, and 200ml of purified water was washed 2 times, and 200ml of saturated saline was washed 1 time, and after drying over anhydrous magnesium sulfate, the ethyl acetate-methanol solution was recrystallized to obtain compound 2-1-1 (yield 68%).
Calculated value C58H49BSi：784.91±1。1H-NMR(400MHz，CDCl3)(ppm)δ＝1.3～1.4(12H，d)，2.8～2.9(2H，m)，7.3～7.4(6H，t)，7.4～7.5(6H，d)，7.4～7.6(9H，t)，7.50～7.55(2H，d)，7.69～7.71(1H,s),7.69～7.71(4H,d),7.74～7.76(4H，d)，7.8～8.0(1H，s)，7.8～8.0(2H，d)。
Example 1
This example consists in preparing an organic electroluminescent device according to the invention.
After ultrasonically washing a glass substrate having an Indium Tin Oxide (ITO) electrode (first electrode, anode) with a thickness of about 1500 angstroms with distilled water and methanol in sequence, the washed glass substrate was dried, moved to a plasma cleaning system, and then cleaned using an oxygen plasma for about 5 minutes. The glass substrate is then loaded into a vacuum deposition apparatus.
Vacuum depositing HAT-CN onto the ITO electrode of the glass substrate to form a hole injection layer HIL having a thickness of about 100 angstroms; vacuum deposition of NPB onto the hole injection layer formed a hole transport layer HTL having a thickness of about 400 angstroms.
The organic light emitting compounds 1-1-1 and ADN were co-deposited on the hole transport region at a ratio of 6:94 to form an emission layer EML having a thickness of about 300 angstroms.
TPBi is vacuum deposited on the EML to form an electron transport layer ETL having a thickness of about 300 angstroms. Then, LiF was deposited on the ETL to form an electron injection layer EIL having a thickness of about 5 angstroms, and Al was deposited on the EIL to a thickness of about 1000 angstroms to form a second electrode (cathode), thereby preparing an organic electroluminescent device of the present invention:
Figure BDA0001799117730000251
examples 2 to 17
An organic electroluminescent device was fabricated by the same method as in example 1, except that the organic luminescent compound in table 1 was used instead of compound 1-1-1 in example 1.
Example 18
An organic electroluminescent device was fabricated by the same method as in example 1, except that the organic luminescent compound 1-1-1 and ADN were deposited on the hole transport region at a weight ratio of 4: 96.
Example 19
An organic electroluminescent device was fabricated by the same method as in example 1, except that the organic luminescent compound 1-1-1 and ADN were deposited on the hole transport region at a weight ratio of 10: 90.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound BD-1 was used in place of the compound 1-1-1 in example 1.
Figure BDA0001799117730000261
Comparative example 2
An organic light-emitting device was produced in the same manner as in example 1, except that the compound BD-2 was used in place of the compound 1-1-1 in example 1.
Figure BDA0001799117730000271
Evaluation: evaluation of characteristics of organic light-emitting device
The driving voltage, emission efficiency and lifetime of the organic light emitting devices in examples and comparative examples were measured using a current-voltage source meter (Keithley 2400) and a Minolta CS-1000A spectroradiometer. The results are shown in table 1 below.
(1) Measurement of current density change with respect to voltage change
The current density was obtained by measuring the value of current flowing through each of the organic electroluminescent devices while increasing the voltage from 0 volt (V) to about 10V by using a current-voltage source meter (Keithley 2400), and then dividing it by the area of the corresponding light emitting device.
(2) Measurement of brightness variation with respect to voltage variation
The luminance of the organic electroluminescent device was measured while increasing the voltage from about 0V to about 10V by using a Minolta CS-1000A spectroradiometer.
(3) Measurement of emission efficiency
The organic light emitting device was calculated at 1000cd/m based on the current density, voltage and luminance obtained by the above-described measurements (1) and (2)2Current efficiency at luminance.
(4) Measurement of half-life
Hold 500cd/m2Luminance (cd/m)2) And measuring the current efficiencyThe time for the rate (cd/A) to decrease to 95%.
TABLE 1
Figure BDA0001799117730000272
Figure BDA0001799117730000281
It can be seen from the examples and comparative examples that when the organic light emitting compound of the present invention is used as a guest material of a light emitting layer in an organic electroluminescent device, the organic electroluminescent device of the present invention has reduced driving voltage, improved light emitting efficiency, and significantly prolonged service life.
It can be seen from the results of example 1, example 18 and example 19 that, when the organic light-emitting compound of the present invention is used as a guest material of a light-emitting layer in an organic electroluminescent device, when the host and the guest are formed into light-emitting layers in different proportions, the same effect is obtained, so that the organic electroluminescent device of the present invention has a lower driving voltage, a higher light-emitting efficiency and a longer service life.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.

Claims (10)

1. An organic light-emitting compound having a structure represented by formula (I),
Figure FDA0001799117720000011
wherein, in the formula (I),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthaleneOr L is1And L2Each independently is absent;
R1、R2and R3Each independently selected from H and C1-12Alkyl groups of (a);
R4and R5Each independently selected from H, C1-12Alkyl, substituted or unsubstituted phenyl of (a);
R6and R7Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted indolyl, and substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted monocyclic group with or without heteroatoms selected from O, S, N and B, a substituted or unsubstituted bicyclic group with or without heteroatoms selected from O, S and N, or a substituted or unsubstituted tricyclic group with or without heteroatoms selected from O, S and N;
L1、L2、R4、R5、R6and R7Wherein the substituents are each independently selected from C1-12Alkyl group of (A), phenyl group, biphenyl group, cyano group, fluorine atom, C substituted by 1 to 3 fluorine atoms1-12And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
2. The compound according to claim 1, wherein, in formula (I),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or L1And L2Each independently is absent;
R1、R2and R3Each independently selected from H and C1-8Alkyl groups of (a);
R4and R5Each independently selected from H, C1-8Alkyl of (2)A substituted or unsubstituted phenyl group;
R6and R7Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted monocyclic group with or without heteroatoms selected from O, S and B, a substituted or unsubstituted bicyclic group with or without heteroatoms selected from O, S and B, or a substituted or unsubstituted tricyclic group with or without heteroatoms selected from O, S and B;
L1、L2、R4、R5、R6and R7Wherein the substituents are each independently selected from C1-8Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms1-8And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
3. A compound according to claim 2, wherein, in formula (I), R6And R7Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted monocyclic group containing an O atom, wherein the unsubstituted monocyclic group containing an O atom is represented by the following structure:
Figure FDA0001799117720000021
and R is6And R7Wherein the substituents are each independently selected from C1-6Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms1-6At least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl of (a);
preferably, R6And R7Wherein the substituents are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, phenyl, biphenyl, cyano, fluoro, C substituted with 1-3 fluorine atoms1-6And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
4. A compound according to claim 2, wherein, in formula (I), R6And R7Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted bicyclic group containing an O atom, wherein the unsubstituted bicyclic group containing an O atom is represented by the following structure:
Figure FDA0001799117720000031
and R is6And R7Wherein the substituents are each independently selected from C1-6Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms1-6At least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl of (a);
preferably, R6And R7Wherein the substituents are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentylN-hexyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms1-6And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
5. A compound according to claim 2, wherein, in formula (I), R6And R7Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinalinyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R6And R7Together with the B atom in formula (I) form a substituted or unsubstituted tricyclic group with or without a heteroatom selected from O, S and B, wherein the unsubstituted tricyclic group with or without a heteroatom selected from O, S and B is represented by any one of the following structures:
Figure FDA0001799117720000041
and in the structure shown as a2, X is O, S, CH2Or BH;
and R6And R7Wherein the substituents are each independently selected from C1-6Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms1-6At least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl of (a);
preferably, R6And R7Wherein the substituents are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, phenyl, biphenyl, cyano, fluoro, C substituted with 1-3 fluorine atoms1-6And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
6. The compound according to any one of claims 1 to 5, wherein the organic light-emitting compound is selected from at least one of the following compounds:
Figure FDA0001799117720000042
Figure FDA0001799117720000051
Figure FDA0001799117720000061
Figure FDA0001799117720000071
Figure FDA0001799117720000081
Figure FDA0001799117720000091
Figure FDA0001799117720000101
Figure FDA0001799117720000111
7. the compound according to any one of claims 1 to 5, wherein the organic light-emitting compound is selected from at least one of the following compounds:
Figure FDA0001799117720000112
Figure FDA0001799117720000121
8. use of the organic light emitting compound according to any one of claims 1 to 7 in an organic electroluminescent device.
9. An organic electroluminescent device comprising one or more compounds of the organic luminescent compounds according to any one of claims 1 to 7; preferably, the first and second electrodes are formed of a metal,
the organic light-emitting compound is present in at least one of an electron transport layer, a light-emitting layer and a hole transport layer of the organic electroluminescent device; preferably, the first and second electrodes are formed of a metal,
the organic light-emitting compound is present in a light-emitting layer of the organic electroluminescent device.
10. The compound according to claim 9, wherein the organic electroluminescent device comprises a substrate, an anode, a hole injection layer, a hole transport layer, an optional electron blocking layer, a light-emitting layer, an optional hole blocking layer, an electron transport layer, an electron injection layer and a cathode, which are sequentially stacked.
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