CN110894203B - 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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CN110894203B
CN110894203B CN201811069329.8A CN201811069329A CN110894203B CN 110894203 B CN110894203 B CN 110894203B CN 201811069329 A CN201811069329 A CN 201811069329A CN 110894203 B CN110894203 B CN 110894203B
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吕瑶
冯美娟
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Beijing Green Guardee Technology Co ltd
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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 light-emitting compound provided by the invention can regulate and control the HOMO energy level and LUMO energy level of an organic light-emitting material, and simultaneously can enable an organic light-emitting device containing the organic light-emitting compound to have higher fluorescence quantum yield, so that the light-emitting efficiency of the organic light-emitting device is improved, the service life of the organic light-emitting device is prolonged, and the organic light-emitting compound provided by the invention can emit blue light when being used in the organic light-emitting 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 divided into luminescent materials and charge transport materials according to functions, the luminescent materials can be divided into fluorescent materials and phosphorescent materials, a host-guest doping system can be used as the luminescent materials, and the guest materials receive the energy of host materials 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 current OLED formed by adopting materials of all layers still has the defects of high driving voltage, short service life, low current efficiency and low brightness, in particular to the defects of efficiency and service life of a blue organic electroluminescent device.
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, an organic electroluminescent device 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 better thermodynamic stability, a higher glass transition temperature, a good film forming property, and a suitable energy gap through the presence of triphenyl silicon and pyrene structure and B element, and can significantly improve light emitting efficiency and prolong device service life when used as an organic electroluminescent 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 GDA0003571291540000021
wherein, in the formula (I),
L 1 and L 2 Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or L 1 And L 2 Each independently is absent;
R 1 、R 2 and R 3 Each independently selected from H and C 1-12 Alkyl groups of (a);
R 4 and R 5 Each independently selected from H, C 1-12 Substituted or unsubstituted phenyl;
R 6 and R 7 Each 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 R 6 And R 7 Together 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;
L 1 、L 2 、R 4 、R 5 、R 6 and R 7 Wherein the substituents are each independently selected from C 1-12 Alkyl group of (A), phenyl group, biphenyl group, cyano group, fluorine atom, C substituted by 1 to 3 fluorine atoms 1-12 And 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 hereinbefore 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 described in 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, an organic electroluminescent device containing the organic luminescent compound has higher fluorescence quantum yield, so that the luminous efficiency of the organic electroluminescent device is improved, the service life of the device is prolonged, and the organic luminescent compound provided by the invention can emit blue light when being used in the 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 GDA0003571291540000041
wherein, in the formula (I),
L 1 and L 2 Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or L 1 And L 2 Each independently is absent;
R 1 、R 2 and R 3 Each independently selected from H and C 1-12 Alkyl groups of (a);
R 4 and R 5 Each independently selected from H, C 1-12 Alkyl, substituted or unsubstituted phenyl of (a);
R 6 and R 7 Each 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 substitutedOr unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R 6 And R 7 Together 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;
L 1 、L 2 、R 4 、R 5 、R 6 and R 7 Wherein the substituents are each independently selected from C 1-12 Alkyl group of (A), phenyl group, biphenyl group, cyano group, fluorine atom, C substituted by 1 to 3 fluorine atoms 1-12 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
“C 1-12 The "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 "C 1-8 Alkyl of and C 1-6 The 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.
“L 1 And L 2 Each independently absent represents L 1 And L 2 May 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),
L 1 and L 2 Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or L 1 And L 2 Each independently is absent;
R 1 、R 2 and R 3 Each independently selected from H and C 1-8 Alkyl groups of (a);
R 4 and R 5 Each independently selected from H, C 1-8 Substituted or unsubstituted phenyl;
R 6 and R 7 Each 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 R 6 And R 7 Together 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;
L 1 、L 2 、R 4 、R 5 、R 6 and R 7 Wherein the substituents are each independently selected from C 1-8 Alkyl, phenyl, biphenyl, cyano, fluorine, C substituted by 1 to 3 fluorine atoms 1-8 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
Provided below is R 6 And R 7 Several preferred embodiments of (a):
embodiment mode 1:
in the formula (I), R 6 And R 7 Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienylSubstituted 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 R 6 And R 7 Together 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 GDA0003571291540000061
and R is 6 And R 7 Wherein the substituents are each independently selected from C 1-6 Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms 1-6 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
Embodiment mode 2:
in the formula (I), R 6 And R 7 Each 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 R 6 And R 7 Together 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 GDA0003571291540000062
and R is 6 And R 7 Wherein 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 atoms 1-6 Alkyl, pyridine ofAt least one of an aryl, a pyrimidinyl, an indolyl and a phenyl substituted indolyl.
In embodiments 1 and 2, when R 6 And R 7 When 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 optional substitutable position of the monocyclic group.
Embodiment mode 3:
in the formula (I), R 6 And R 7 Each 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 R 6 And R 7 Together 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 GDA0003571291540000071
and R is 6 And R 7 Wherein the substituents are each independently selected from C 1-6 Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms 1-6 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
Embodiment 4:
in the formula (I), R 6 And R 7 Each 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 R 6 And R 7 Together with the B atom in formula (I) form a radical containingA substituted or unsubstituted bicyclic group having an O atom, wherein the unsubstituted bicyclic group having an O atom is represented by the following structure:
Figure GDA0003571291540000081
and R is 6 And R 7 Wherein 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 atoms 1-6 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
In embodiments 3 and 4, when R 6 And R 7 When 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), R 6 And R 7 Each 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 R 6 And R 7 Together with the B atom in formula (I) form a substituted or unsubstituted tricyclic group with or without heteroatoms selected from O, S and B, wherein the unsubstituted tricyclic group with or without heteroatoms selected from O, S and B is any of the following structures:
Figure GDA0003571291540000082
and in the structure shown as a2, X is O, S, CH 2 Or BH;
and R 6 And R 7 Wherein the substituents are each independently selected from C 1-6 Alkyl, phenyl, biphenyl, cyano, fluorine, C substituted by 1 to 3 fluorine atoms 1-6 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
Embodiment 6:
in the formula (I), R 6 And R 7 Each 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 quinlinyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R 6 And R 7 Together with the B atom in formula (I) form a substituted or unsubstituted tricyclic group with or without heteroatoms selected from O, S and B, wherein the unsubstituted tricyclic group with or without heteroatoms selected from O, S and B is any of the following structures:
Figure GDA0003571291540000091
and in the structure shown as a2, X is O, S, CH 2 Or BH;
and R is 6 And R 7 Wherein 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 atoms 1-6 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
In embodiments 5 and 6, when R 6 And R 7 When a substituted tricyclic group containing a heteroatom selected from O, S and B is formed together with the B atom in formula (I), the substituent may be substituted at any position of the tricyclic group that can be substituted.
And, in the detailed descriptionIn formulas 5 and 6, when R 6 And R 7 Together with the B atom in formula (I) form a substituted tricyclic group with or without heteroatoms selected from O, S and B, and when X in the structure shown by a2 is C or B, H present on X can be substituted with at least one of the substituents defined above, for example, when X is C or B, H present on X can be substituted with a group such as methyl, ethyl, isopropyl, tert-butyl, phenyl, and the like.
Preferably, in the aforementioned embodiments 1 to 6 of the present invention,
L 1 and L 2 Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or L 1 And L 2 Each independently is absent;
R 1 、R 2 and R 3 Each independently selected from H and C 1-8 Alkyl groups of (a);
R 4 and R 5 Each independently selected from H, C 1-8 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 following compounds:
Figure GDA0003571291540000101
Figure GDA0003571291540000111
Figure GDA0003571291540000121
Figure GDA0003571291540000131
Figure GDA0003571291540000141
Figure GDA0003571291540000151
Figure GDA0003571291540000161
in order to further increase the luminous efficiency of the organic electroluminescent device comprising the present invention, according to another preferred embodiment, the organic luminescent compound of the present invention is selected from at least one of the following compounds:
Figure GDA0003571291540000162
Figure GDA0003571291540000171
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 GDA0003571291540000181
wherein, in the formula (II),
R 11 、R 12 and R 13 May 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, pyrimidineImidazole, 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 GDA0003571291540000191
wherein, in the formula (III),
R 14 、R 15 and R 16 May 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 sulfone derivative has a structure represented by formula (IV):
Figure GDA0003571291540000192
wherein the ketone derivative has a structure represented by formula (V):
Figure GDA0003571291540000193
wherein R is 17 、R 18 、R 19 And R 20 May 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, and quinolineAn 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 to 1000 angstroms, more preferably 150 to 400 angstroms.
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 to 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, sqMA 1), 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 GDA0003571291540000201
wherein, in formulae (VI) to (IX):
R′ 1 to R' 9 May 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, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, dimethylfluorene, spirobifluorene, carbazole, perylene, and mixtures thereof,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 to 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 higher LUMO energy level is provided, and the purpose is to reduce the number of electrons leaving the light-emitting layer, thereby improving the recombination probability of electrons and holes in the light-emitting layer.
(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., spMA 2), 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 device has larger triplet energy, and the purpose of the triplet energy is to reduce the number of excitons leaving the light emitting layer, thereby improving the efficiency of exciton conversion 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 Al 2 O 3 And 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 800-1500 angstroms.
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 vacuum sublimation temperature is less than 10 deg.C -3 Pa, preferably less than 10 -6 The 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 -6 The 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 preparing the organic electroluminescent device 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, in particular 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, decalin, dodecylbenzene, methyl benzoate, NMP, p-methylisobenzoic benzene, 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, diethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 3924 zxft 3534-bis (3534-dimethylphenyl) ethane, and 3-dimethylheptanol.
Preferably, the organic electroluminescent device of the present invention is prepared byThe organic light-emitting compound and the other compound are first mixed well and then a layer or layers are formed by the above-described application method. More preferably, in the vacuum sublimation system, less than 10 -3 Pa, preferably less than 10 -6 Pa, the respective compound is applied by vapour deposition to form a layer or 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 GDA0003571291540000241
Synthesis of intermediate 1-1-1-1: dissolving 0.1mol of 1,6-dibromopyrene in 360ml of dioxane solvent, sequentially adding 0.2mol of p-isopropylphenylboronic acid, 0.25mol of K2CO3 and 0.001mol 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 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 that for the intermediate 1-1-1-1, and the intermediate 1-1-1-3 was obtained (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, detecting that the reaction of the raw materials is finished, dropwise adding 500ml of water into the reaction solution to separate out a large amount of solid, stirring for half an hour, filtering to obtain a residue, and performing column chromatography to obtain an intermediate 1-1-1-4 (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 C70H57Bsi:937.10 ± 1.1H-NMR (400MHz, CDCl3) (ppm) delta = 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 GDA0003571291540000251
Synthesis of Compounds 1-1-14: adding 0.01mol of bis (trimethylphenyl) boron fluoride into 20ml of tetrahydrofuran, adding 0.1mol of magnesium chips, heating to reflux, dropwise adding a small amount of 1,2-dibromoethane to initiate reaction, and continuously supplementing 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-butyl lithium 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 (the yield is 53%).
Calcd for C76H69Bsi:1021.26 ± 1.1H-NMR (400MHz, CDCl3) (ppm) delta = 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 GDA0003571291540000261
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 diboride, 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 performing column chromatography on residues to obtain intermediate 1-1-39-2 (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 C82H61BO2Si:1117.26 ± 1.1H-NMR (400MHz, CDCl3) (ppm) delta =1.20 to 1.20 (12H, d), 2.87 to 2.88 (2H, m), 7.32 to 7.55 (31H, m), 7.66 to 7.70 (8H, m), 7.80 to 7.81 (2H, m), 7.89 to 7.90 (4H, m), 8.0 to 8.0 (1H, s), 8.3 to 8.3 (1H, s).
Preparation example 4: compounds 1-1-54
Figure GDA0003571291540000271
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 C70H55BOSi:951.08 ± 1.1H-NMR (400MHz, CDCl3) (ppm) delta =1.20 to 1.21 (12H, d), 2.87 to 2.88 (2H, m), 7.14 to 7.17 (4H, m), 7.36 to 7.55 (27H, m), 7.70 to 7.71 (6H, m), 7.88 to 7.89 (2H, m), 8.20 to 8.21 (1H, s), 8.29 to 8.30 (1H, s).
Preparation example 5: compounds 1-1-70
Figure GDA0003571291540000281
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 minus 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 C82H73Bsi:1097.35 ± 1.1H-NMR (400MHz, CDCl3) (ppm) delta = 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 (2H, s).
Preparation example 6: compounds 1-1-109
Figure GDA0003571291540000291
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 2-chlorophthalic diborane, 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 intermediate compounds 1-1-109. (yield 65%)
Calcd for C64H51BO2Si:890.99 ± 1.1H-NMR (400MHz, CDCl3) (ppm) delta = 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 GDA0003571291540000292
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 tetrahydrofuran saturated solution of the 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 that the reaction of the raw materials is finished after 2h, adding n-hexane into the reaction liquid for extraction, taking organic phase for pressure spin drying, and carrying out 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 C80H63BN2Si:1091.27 ± 1.1H-NMR (400MHz, CDCl3) (ppm) delta = 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 GDA0003571291540000301
And (3) synthesizing an intermediate 2-1-1-1: 1,6-diisopropylpyrene (2.94 mmol), benzyl trimethyl ammonium bromide (3.22 mmol) and chloroform (60 ml) were put in 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: 2-1-1-1-1.0mmol of the intermediate and 50ml of anhydrous tetrahydrofuran are put into a 250ml three-necked bottle, the temperature is reduced to minus 78 ℃ by liquid nitrogen under the protection of nitrogen, 6.3ml of 1.6M n-butyllithium/n-hexane solution (10 mmol) is dropwise added, after the dropwise addition is finished, the mixture is stirred for 1.5 hours at minus 78 ℃, 30ml of tetrahydrofuran solution of 10mmol of fluorobenzylborane is dropwise added, and after the dropwise addition is finished, the reaction is continued for 12 hours. 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 the intermediate 2-1-1-324.75mmol,27.22mmol 4- (triphenylsilyl) phenylboronic acid, 1.23mmol Pd (PPh) 3 ) 4 ，61.9mmol K 2 CO 3 61.9mmol, 10ml of purified water and 120ml of 1-4-dioxane, and the mixture was refluxed for 12 hours after being replaced with nitrogen gas for 3 times. 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 C 58 H 49 BSi：784.91±1。1H-NMR(400MHz，CDCl 3 )(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 compound 1-1-1 was co-deposited with ADN at a ratio of 6.
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 GDA0003571291540000321
examples 2 to 18
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 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 in a weight ratio of 4.
Example 20
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.
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 GDA0003571291540000331
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 GDA0003571291540000341
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 current 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) 2 Current efficiency at luminance.
(4) Measurement of half-life
Hold 500cd/m 2 Luminance (cd/m) 2 ) And the time for the current efficiency (cd/a) to decrease to 95% was measured.
TABLE 1
Figure GDA0003571291540000342
Figure GDA0003571291540000351
It can be seen from the examples and comparative example 1 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 19 and example 20 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 various technical features being combined 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 (15)

1. An organic light-emitting compound having a structure represented by formula (I),
Figure FDA0003571291530000011
wherein, in the formula (I),
L 1 and L 2 Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or L 1 And L 2 Each independently is absent;
R 1 、R 2 and R 3 Each independently selected from H and C 1-12 Alkyl groups of (a);
R 4 and R 5 Each independently selected from H, C 1-12 Alkyl, substituted or unsubstituted phenyl of (a);
R 6 and R 7 Each 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 R 6 And R 7 Together 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;
L 1 、L 2 、R 4 、R 5 、R 6 and R 7 Wherein the substituents are each independently selected from C 1-12 Alkyl group of (2), phenyl group, biphenyl group, cyano group, fluorine atom, C substituted by 1 to 3 fluorine atoms 1-12 Alkyl, pyridyl, pyrimidyl, indolyl and benzene ofAt least one of an indolyl group substituted with a substituent.
2. The compound according to claim 1, wherein, in formula (I),
L 1 and L 2 Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or L 1 And L 2 Each independently is absent;
R 1 、R 2 and R 3 Each independently selected from H and C 1-8 Alkyl groups of (a);
R 4 and R 5 Each independently selected from H, C 1-8 Substituted or unsubstituted phenyl;
R 6 and R 7 Each 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 R 6 And R 7 Together 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;
L 1 、L 2 、R 4 、R 5 、R 6 and R 7 Wherein the substituents are each independently selected from C 1-8 Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms 1-8 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
3. A compound according to claim 2, wherein, in formula (I), R 6 And R 7 Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substitutedOr unsubstituted dibenzothienyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinuclidinyl, substituted or unsubstituted pyrimidinyl, and substituted or unsubstituted indolyl, substituted or unsubstituted benzimidazolyl, or R 6 And R 7 Together 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 FDA0003571291530000021
and R is 6 And R 7 Wherein the substituents are each independently selected from C 1-6 Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms 1-6 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
4. A compound according to claim 3, wherein R 6 And R 7 Wherein 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 atoms 1-6 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
5. A compound according to claim 2, wherein, in formula (I), R 6 And R 7 Each 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 R 6 And R 7 Together with the B atom in formula (I) form a substituted or unsubstituted bicyclic radical containing an O atomWherein the unsubstituted bicyclic group containing an O atom is represented by the following structure:
Figure FDA0003571291530000031
and R is 6 And R 7 Wherein the substituents are each independently selected from C 1-6 Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms 1-6 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
6. The compound of claim 5, wherein R 6 And R 7 Each of the substituents in (1) is independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, phenyl, biphenyl, cyano, fluorine, C substituted with 1-3 fluorine atoms 1-6 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl, and phenyl-substituted indolyl.
7. A compound according to claim 2, wherein, in formula (I), R 6 And R 7 Each 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 R 6 And R 7 Together with the B atom in formula (I) form a substituted or unsubstituted tricyclic group with or without heteroatoms selected from O, S and B, wherein the unsubstituted tricyclic group with or without heteroatoms selected from O, S and B is any of the following structures:
Figure FDA0003571291530000041
and in the structure shown as a2, X is O, S, CH 2 Or BH;
and R 6 And R 7 Wherein the substituents are each independently selected from C 1-6 Alkyl, phenyl, biphenyl, cyano, fluoro, C substituted by 1-3 fluorine atoms 1-6 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl and phenyl-substituted indolyl.
8. The compound of claim 7, wherein R 6 And R 7 Wherein 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 atoms 1-6 And at least one of alkyl, pyridyl, pyrimidinyl, indolyl, and phenyl-substituted indolyl.
9. The compound according to any one of claims 1 to 8, wherein the organic light-emitting compound is selected from at least one of the following compounds:
Figure FDA0003571291530000051
Figure FDA0003571291530000061
Figure FDA0003571291530000071
Figure FDA0003571291530000081
Figure FDA0003571291530000091
Figure FDA0003571291530000101
Figure FDA0003571291530000111
10. the compound according to any one of claims 1 to 8, wherein the organic light-emitting compound is selected from at least one of the following compounds:
Figure FDA0003571291530000112
Figure FDA0003571291530000121
11. use of the organic light emitting compound of any one of claims 1 to 10 in an organic electroluminescent device.
12. An organic electroluminescent device comprising one or more of the organic light-emitting compounds according to any one of claims 1 to 10.
13. The organic electroluminescent device according to claim 12, wherein the organic luminescent 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.
14. The organic electroluminescent device according to claim 13, wherein the organic luminescent compound is present in a luminescent layer of the organic electroluminescent device.
15. The organic electroluminescent device according to any one of claims 12 to 14, 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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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090236975A1 (en) * 2006-05-09 2009-09-24 Idemitsu Kosan Co., Ltd. Silicon-containing compound and organic electroluminescent device utilizing the same
CN103896973A (en) * 2014-04-11 2014-07-02 中国科学院理化技术研究所 Di (trimethyl phenyl) boron derivative and application thereof in white organic electroluminescent diode
CN106565433A (en) * 2016-10-26 2017-04-19 北京绿人科技有限责任公司 Organic compound and application thereof in electroluminescent device
CN108409774A (en) * 2017-12-19 2018-08-17 北京绿人科技有限责任公司 Organic electroluminescent compounds and its application and organic electroluminescence device
CN108424420A (en) * 2017-09-30 2018-08-21 北京绿人科技有限责任公司 Triaizine compounds containing silicon atom and its application and a kind of organic electroluminescence device

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Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090236975A1 (en) * 2006-05-09 2009-09-24 Idemitsu Kosan Co., Ltd. Silicon-containing compound and organic electroluminescent device utilizing the same
CN103896973A (en) * 2014-04-11 2014-07-02 中国科学院理化技术研究所 Di (trimethyl phenyl) boron derivative and application thereof in white organic electroluminescent diode
CN106565433A (en) * 2016-10-26 2017-04-19 北京绿人科技有限责任公司 Organic compound and application thereof in electroluminescent device
CN108424420A (en) * 2017-09-30 2018-08-21 北京绿人科技有限责任公司 Triaizine compounds containing silicon atom and its application and a kind of organic electroluminescence device
CN108409774A (en) * 2017-12-19 2018-08-17 北京绿人科技有限责任公司 Organic electroluminescent compounds and its application and organic electroluminescence device

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