CN112142605A - Compound, application thereof and organic electroluminescent device comprising compound - Google Patents
Compound, application thereof and organic electroluminescent device comprising compound Download PDFInfo
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- CN112142605A CN112142605A CN201910573218.9A CN201910573218A CN112142605A CN 112142605 A CN112142605 A CN 112142605A CN 201910573218 A CN201910573218 A CN 201910573218A CN 112142605 A CN112142605 A CN 112142605A
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- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005579 tetracene group Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to a compound, application thereof and an organic electroluminescent device comprising the compound, wherein the compound has the following formulaI is shown as the structure:
L1～L4each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene; ar (Ar)1～Ar4Each independently selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; x1‑X6Are each independently selected from CR1、CR2Or CR3. When the compound is used as a hole transport layer material in an OLED device or an electron blocking layer material, excellent device performance and stability are shown. The invention also protects the organic electroluminescent device adopting the compound with the general formula.
Description
Technical Field
The invention relates to the field of organic light-emitting compounds and organic electroluminescent devices, in particular to a compound, application thereof and an organic electroluminescent device containing the compound.
Background
In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them well suited for fabrication on flexible substrates, allowing for the design and production of aesthetically pleasing and crunchy optoelectronic products, with unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLEDs have been developed particularly rapidly, and have been commercially successful in the field of information display. The OLED can provide three colors of red, green and blue with high saturation, and a full-color display device manufactured by using the OLED does not need an additional backlight source and has the advantages of colorful, light, thin and soft color and the like.
The core of the OLED device is a thin film structure containing various organic functional materials. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like. When electricity is applied, electrons and holes are injected, transported to the light emitting region, and recombined therein, respectively, thereby generating excitons and emitting light.
People have developed various organic materials, and the organic materials are combined with various peculiar device structures, so that the carrier mobility can be improved, the carrier balance can be regulated, the electroluminescent efficiency can be broken through, and the attenuation of the device can be delayed. For quantum mechanical reasons, common fluorescent luminophores mainly utilize singlet excitons generated when electrons and air are combined to emit light, and are still widely applied to various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet excitons and singlet excitons, which are called phosphorescent emitters, and the energy conversion efficiency can be increased by up to four times as compared with conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technology can still effectively utilize triplet excitons to achieve higher luminous efficiency without using a metal complex by promoting the conversion of triplet excitons to singlet excitons. Thermal excitation sensitized fluorescence (TASF) technology also achieves higher luminous efficiency by sensitizing the emitter by energy transfer using TADF-like materials.
As OLED products gradually enter the market, there are increasingly higher requirements on the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, service life, cost and the like. The present inventors have discovered a clever molecular design through careful consideration and ongoing experimentation, and are described in detail below. Surprisingly, the compounds disclosed in the present invention are very suitable for application in OLEDs and improve the performance of the devices.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide a novel compound, an organic electroluminescent device containing the compound and application thereof, and an OLED device based on the compound has low starting voltage, high luminous efficiency and better service life and can meet the requirements of panel manufacturing enterprises on high-performance materials at present.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides a compound having the structure shown in formula I below:
wherein L is1～L4Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene;
Ar1～Ar4each independently selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
X1-X6are each independently selected from CR1、CR2Or CR3And X1、X4And X5At least one of which is not CR1；
R1Is hydrogen, R2Is selected from C1～C12Alkyl radical, C3～C12Cycloalkyl radical, C1～C12One of the alkoxy radicals, R3Selected from substituted or unsubstituted C6～C30One of aryl and substituted or unsubstituted C3-C30 heteroaryl;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic aromatic hydrocarbon or fused ring aromatic hydrocarbon group, C3-C30 monocyclic heteroaromatic hydrocarbon or fused ring heteroaromatic hydrocarbon group.
Further, in the formula I, L1～L4Preferably a single bond.
Further, in formula I, X1、X4And X5At least one of which is CR3。
Further, in formula I, X1Is CR2Or CR3(ii) a Still further, X is preferred1Is CR3。
Further, in formula I, X2、X3And X6Are all CR1。
Further, in formula I, X1、X4And X5One of them is CR3，X1～X6The other five are CR1。
Further, in formula I, X1Is CR2Or CR3，X1～X6Middle removing X1The other five are CR1；
Further, in the formula I, X1Is CR3，X1～X6Middle removing X1The other five are CR1。
Further, in formula I, preferably, Ar is1～Ar4Selected from substituted or unsubstitutedSubstituted of the following groups: one of phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothienyl;
further, in the formula I, R3One selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 electron donating heteroaryl;
further, in the formula I, preferably, R is3Selected from the following substituted or unsubstituted groups: one of phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, dibenzofuranyl or dibenzothienyl;
in the present invention, said C6-C30Substituted or unsubstituted arylene of and C6-C30C in substituted or unsubstituted aryl6-C30Represents the number of carbon atoms in the group and may be, for example, 6, 10, 12, 15, 18, 20, 23, 25, 28, 30 carbon atoms; in the same way, C3-C30Substituted or unsubstituted heteroarylene of (1) and C3-C30The number of carbon atoms in the substituted or unsubstituted heteroaryl group can be 8, 12, 15, 18, 20, 23, 25, 28, or 30; c1-C20The number of carbon atoms in the alkyl group of (a) may be 1, 3, 5, 8, 10, 12, 15, 18 or 20, and as such other limitation of the range of carbon atoms indicates that the number of carbon atoms in the group may take any integer within the recited range of values. Unless otherwise specified, generally the number of carbon atoms does not include the number of carbon atoms of the substituent.
In the present invention, the expression of chemical elements includes the concept of chemically identical isotopes, such as the expression of "hydrogen", and also includes the concept of chemically identical "deuterium" and "tritium".
The term heteroatom as used herein is generally intended to mean a heteroatom selected from N, O, S.
In the structure shown in the present invention, the expression "connecting bond to a substituent" - "crossing a ring structure means that the connecting site is located at an arbitrary position on the ring structure where a bond can be formed.
The substituted or unsubstituted C1-C12 alkyl group is preferably a C1-C10 alkyl group, more preferably a C1-C6 alkyl group, and examples thereof include: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl and the like.
The substituted or unsubstituted C3-C12 cycloalkyl group is preferably C3-C10 cycloalkyl group, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
The substituted or unsubstituted C6-C30 aryl group preferably has 6 to 20 skeletal carbon atoms, and is preferably a phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, phenanthryl group, indenyl group, fluorenyl group and derivatives thereof, fluoranthryl group, triphenylene group, pyrenyl group, perylenyl group, perylene group, or the like,
A group of the group consisting of a phenyl group and a tetracenyl group. The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group is a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from the group consisting of 1-anthracene group, 2-anthracene group, and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9 '-dimethylfluorene, 9, 9' -spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene.
The substituted or unsubstituted C6 to C30 heteroaryl group preferably has 6 to 20 skeletal carbon atoms, and is preferably a furyl group, a thienyl group, a pyrrolyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group and a derivative thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole.
Wherein,
represents an access position of a group; the expression of the "underlined loop structure" indicates that the linking site is located at an arbitrary position on the loop structure where the linkage can be formed.
Preferably, the compound is any one of the following compounds P1-P209:
in the present invention, the compound is any one of P1 to P209, but is not limited to these exemplary compounds.
As another aspect of the present invention, the present invention provides the use of the compound as described above in an organic electroluminescent device, and the compound of the present invention is preferably used in an organic electroluminescent device as a hole transport material or an electron blocking layer material, and can further reduce the driving voltage of the device, improve the light emitting efficiency of the device, and prolong the service life of the device, compared with the compounds in the prior art.
In the present invention, the organic layer containing the compound of the present invention can be used as, but not limited to, a hole transport layer and an electron blocking layer. The compound of the present invention can be applied to organic electronic devices such as organic electroluminescent devices, lighting devices, organic thin-film transistors, organic field-effect transistors, organic thin-film solar cells, information tags, electronic artificial skin sheets, large-area sensors such as sheet scanners, electronic paper, and organic EL panels.
In another aspect, the present invention also provides an organic electroluminescent device comprising a substrate, a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layers comprise at least one compound represented by any one of the above general formulae or specific formulae of the present invention.
Specifically, another technical scheme of the present invention provides an organic electroluminescent device, including a substrate, and an anode layer, a plurality of light emitting functional layers and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer and an electron transport layer, wherein at least one of the hole transport layer and the electron blocking layer contains the compound shown in any one of the general formula or the specific structural formula.
The specific reason why the above-mentioned compound of the present invention is excellent in the performance as a hole transporting material and/or an electron blocking material in an organic electroluminescent device is not clear, and it is presumed that the following reasons are possible:
in the compound structure, the parent nucleus has a double triarylamine structure, and has better hole transport capability compared with a single triarylamine compound; secondly, introduction of R into the ortho position2Or R3Group through R2Or R3The size of the steric hindrance at the ortho position is reasonably adjusted, so that the torsion resistance of the molecule is properly regulated and controlled, and the crystallization property and the material transmission property of the molecule are coordinated to meet the requirements of devices on materials.
When the compound is used as a hole transport layer material or an electron blocking layer material of an organic electroluminescent device, compared with the prior art, the compound can further reduce the driving voltage, improve the luminous efficiency and prolong the service life. Experiments prove that when the material designed by the mother nucleus is used as a hole transport layer material or an electron blocking layer of an organic electroluminescent device, the luminous efficiency can be improved, the starting voltage can be reduced, and the service life of the device can be prolonged. The organic electroluminescent device using the compound of the invention has a luminance of 5000cd/m2When the voltage is low, the driving voltage is below 7.5V, the current efficiency is above 13.5cd/A, and LT95 is above 42 h.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The solvents and reagents used in the following synthesis examples in the present invention, such as aryl bromide, 2-bromo-9, 9 '-dimethylfluorene, 2-bromo-dibenzofuran, 2-bromo-dibenzothiophene, 4-bromo-biphenyl, [1, 1' -bis (diphenylphosphino) ferrocene ] dichloropalladium, tris (dibenzylideneacetone) dipalladium, toluene, petroleum ether, n-hexane, methylene chloride, acetone, sodium sulfate, ethyl acetate, ethanol, tri-tert-butylphosphine, potassium/sodium tert-butoxide, etc., can be purchased or customized from domestic chemical product markets, such as from national drug group reagents, Sigma-Aldrich, bercarb reagents, and intermediate M is customized by reagents. In addition, they can be synthesized by a known method by those skilled in the art.
In the present invention, a method for synthesizing the compound is briefly described, and a representative synthetic route of the compound is as follows:
based on the synthetic route and thought of the above compounds, the skilled person can obtain the substituent Ar1～Ar4、R1～R3A compound of formula I.
Synthesis example 1: synthesis of Compound P1
In a 1000ml single neck flask, 5.8g (25mmol) of M1, 15.7g (100mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 144g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P1, wherein the theoretical value of M/Z is 538, and the actual value of M/Z is 539.
Synthesis example 2: synthesis of Compound P2
In a 1000ml single neck flask, 11.7g (50mmol) of M1, 15.6g (50mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M1-1.
In a 1000ml single-necked flask, 19.3g (50mmol) of M1-1, 20.6g (100mmol) of 2-bromonaphthalene, and 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P2, wherein the theoretical value of M/Z is 700, and the actual value of M/Z is 701.
Synthesis example 3: synthesis of Compound P4
In a 1000ml single-neck bottle, add11.7g (50mmol) M1, 15.6g (50mmol) bromobenzene, 0.9g (1mmol) tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M1-1.
In a 1000ml single-neck flask were added 19.3g (50mmol) of M1-1, 27.2g (100mmol) of 2-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P4, wherein the theoretical value of M/Z is 770, and the actual value of M/Z is 771.
Synthesis example 4: synthesis of Compound P7
In a 1000ml single neck flask, 11.7g (50mmol) of M1, 15.6g (50mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M1-1.
In a 1000ml single-neck flask were added 19.3g (50mmol) of M1-1, 27.2g (100mmol) of 3-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished.Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P7, wherein the theoretical value of M/Z is 770, and the actual value of M/Z is 771.
Synthesis example 5: synthesis of Compound P8
In a 1000ml single neck flask, 11.7g (50mmol) of M1, 15.6g (50mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M1-1.
In a 1000ml single-neck flask were added 19.3g (50mmol) of M1-1, 24.6g (100mmol) of 3-bromodibenzofuran, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P8, wherein the theoretical value of M/Z is 718, and the actual value of M/Z is 719.
Synthesis example 6: synthesis of Compound P11
In a 1000ml single neck flask, 11.7g (50mmol) of M1, 15.6g (50mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3)、0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuum pumping and nitrogen exchange 3 times, reaction temperature rising to 90 ℃ reaction for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M1-1.
In a 1000ml single-necked flask, 19.3g (50mmol) of M1-1, 23.2g (100mmol) of 3-bromobiphenyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P11, wherein the theoretical value of M/Z is 690, and the actual value of M/Z is 691.
Synthesis example 7: synthesis of Compound P16
In a 1000ml single-neck flask, 11.7g (50mmol) of M1, 23.2g (50mmol) of 3-bromobiphenyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M1-2.
In a 1000ml single-neck flask, 26.9g (50mmol) of M1-2, 27.2g (50mmol) of 3-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P16, M/Z theory922, found value of M/Z, 923.
Synthesis example 8: synthesis of Compound P28
In a 1000ml single neck flask, 7.1g (25mmol) of M2, 15.7g (100mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P28, wherein the theoretical value of M/Z is 588, and the actual value of M/Z is 589.
Synthesis example 9: synthesis of Compound P34
In a 1000ml single neck flask were added 14.2g (50mmol) of M2, 15.6g (50mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M2-1.
In a 1000ml single-neck flask, 20.8g (50mmol) of M2-1, 27.2g (100mmol) of 3-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol, stirring for 1h, and vacuum filtering to obtain light yellow powderP34, theoretical M/Z value 820, and measured M/Z value 821.
Synthesis example 10: synthesis of Compound P43
In a 1000ml single-neck flask, 14.2g (50mmol) of M2, 23.2g (50mmol) of 3-bromobiphenyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M2-2.
In a 1000ml single-necked flask, 29.9g (50mmol) of M2-2, 27.2g (50mmol) of 3-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P43 with theoretical M/Z value of 972 and actual M/Z value of 973.
Synthesis example 11: synthesis of Compound P58
In a 1000ml single neck flask, 15.5g (50mmol) of M3, 15.6g (50mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M3-1.
In a 1000ml single-neck flask were added 19.3g (50mmol) of M3-1, 27.2g (100mmol) of 2-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P58, wherein the theoretical value of M/Z is 846, and the actual value of M/Z is 847.
Synthesis example 12: synthesis of Compound P83
In a 1000ml single neck flask, 7.1g (25mmol) of M4, 15.7g (100mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P83, wherein the theoretical value of M/Z is 588, and the actual value of M/Z is 589.
Synthesis example 13: synthesis of Compound P110
In a 1000ml single neck flask, 8.1g (25mmol) of M5, 15.7g (100mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol, stirring for 1h, and pumpingFiltration gave P110 as a pale yellow powder, which had a theoretical value of M/Z of 628 and an actual value of M/Z of 629.
Synthesis example 14: synthesis of Compound P116
In a 1000ml single neck flask, 16.2g (50mmol) of M5, 15.6g (50mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M5-1.
In a 1000ml single-neck flask, 24g (50mmol) of M5-1, 27.2g (100mmol) of 3-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P116, wherein the theoretical value of M/Z is 860, and the actual value of M/Z is 861.
Synthesis example 15: synthesis of Compound P152
In a 1000ml single-neck flask, 17g (50mmol) of M6, 23.2g (50mmol) of 3-bromobiphenyl, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction solution, concentrating the organic phase, adding methanol, stirring for 1h, and vacuum filtering to obtain light yellowColor powder M6-1.
In a 1000ml single-neck flask, 32.2g (50mmol) of M6-1, 27.2g (50mmol) of 3-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P152, wherein the theoretical value of M/Z is 1028, and the actual value of M/Z is 1029.
Synthesis example 16: synthesis of Compound P170
In a 1000ml single neck flask, 17.5g (50mmol) of M7, 15.6g (50mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M7-1.
In a 1000ml single-neck flask, 25g (50mmol) of M7-1, 27.2g (100mmol) of 3-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P170 with an M/Z theoretical value of 886 and an M/Z measured value of 887.
Synthesis example 17: synthesis of compound P178
In a 1000ml single-neck flask, 17.5g (50mmol) of M7, 20.6g (50mmol) of 2-bromonaphthalene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5g IPr. HCl, 500ml Toluene (Toluene), 14.4g (150mmol) sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M7-2.
In a 1000ml single-neck flask, 30g (50mmol) of M7-2, 26.2g (100mmol) of 3-bromodibenzothiophene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P178, wherein the theoretical value of M/Z is 966, and the actual value of M/Z is 967.
Synthesis example 18: synthesis of compound P192
In a 1000ml single neck flask, 8.8g (25mmol) of M8, 15.7g (100mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P192, wherein the theoretical value of M/Z is 568, and the measured value of M/Z is 569.
Synthesis example 19: synthesis of Compound P193
In a 1000ml single neck flask, 7.6g (25mmol) of M9, 15.7g (100mmol) of bromobenzene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tributylphosphine ((t-Bu)3P), 500ml of Toluene (Toluene), 14.4g (150mmol) of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 h. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P193, wherein the theoretical value of M/Z is 608, and the actual value of M/Z is 609.
Next, the organic electroluminescent device will be explained in detail.
The OLED includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
In one aspect of the present invention, the hole transport region material may be selected from one or more compounds of formula i of the present invention, and the electron blocking layer of the hole transport region may be absent, or may be present and selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrene sulfonate) (Pani/PSS), aromatic amine derivatives such as compounds represented by HT-1 to HT-34 below; or any combination thereof. When the hole transport layer of the hole transport region is selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown below as HT-1 to HT-34, or any combination thereof; the electron blocking layer of the hole transport region is selected from one or any combination of the compounds described above.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI-1-HI-3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI-1-HI-3 described below.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI 1-HI3 described below; combinations of these compounds may also be used.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but not limited to, the combination of one or more of BFH-1 through BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent dopant may be selected from, but is not limited to, combinations of one or more of BFD-1 through BFD-12 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light emitting layer is selected from, but not limited to, one or more of GPH-1 to GPH-80.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer can be selected from, but is not limited to, one or more of GPD-1 to GPD-47 listed below.
Wherein D is deuterium.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but is not limited to, one or more of YPD-1-YPD-11 listed below.
In one aspect of the invention, the light-emitting layer employs a thermally activated delayed fluorescence emission technique. The fluorescent dopant of the light-emitting layer can be selected from, but is not limited to, one or more of TDE1-TDE39 listed below.
In one aspect of the invention, the light-emitting layer employs a thermally activated delayed fluorescence emission technique. The host material of the light emitting layer is selected from, but not limited to, one or more of TDH-1-TDH-24.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-57 listed below.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, combinations of one or more of the following: LiQ, LiF, NaCl, CsF, Li2O,Cs2CO3,BaO,Na,Li,Ca。
Example 1
The preparation process of the organic electroluminescent device in the embodiment is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to<1×10-5Pa, performing vacuum evaporation on the anode layer film to obtain HI-3 serving as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
the compound P1 prepared in synthesis example 1 was vacuum-evaporated on the hole injection layer at an evaporation rate of 0.1nm/s and a total film thickness of 80nm as a hole transport layer of the device;
on the hole transport layer, vacuum evaporation plating HT-14 as an electron barrier layer of the device, wherein the evaporation plating rate is 0.1nm/s, and the total film thickness of the evaporation plating is 80 nm;
a luminescent layer of the device is vacuum evaporated on the electron blocking layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material GPH-59 is adjusted to be 0.1nm/s, the evaporation rate of the dye RPD-8 is set in a proportion of 3%, and the total film thickness of evaporation is 30nm by using a multi-source co-evaporation method;
vacuum evaporating an electron transport layer material ET-46 of the device on the light emitting layer, wherein the proportion of 50 percent and ET-57, 50 percent are set, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 30 nm;
LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
Example 2
The organic electroluminescent device in this example was fabricated in the same manner as in example 1 except that compound P1 was replaced with compound P2 as the hole transport layer material.
Example 3
The organic electroluminescent device in this example was fabricated in the same manner as in example 1 except that compound P1 was replaced with compound P7 as the hole transport layer material.
Example 4
The organic electroluminescent device in this example was fabricated in the same manner as in example 1 except that compound P1 was replaced with compound P11 as the hole transport layer material.
Example 5
The organic electroluminescent device in this example was fabricated in the same manner as in example 1 except that compound P1 was replaced with compound P28 as the hole transport layer material.
Example 6
The organic electroluminescent device in this example was fabricated in the same manner as in example 1 except that compound P1 was replaced with compound P34 as the hole transport layer material.
Example 7
The organic electroluminescent device in this example was fabricated in the same manner as in example 1 except that compound P1 was replaced with compound P58 as the hole transport layer material.
Example 8
The organic electroluminescent device in this example was fabricated in the same manner as in example 1 except that compound P1 was replaced with compound P83 as the hole transport layer material.
Example 9
The organic electroluminescent device in this example was fabricated in the same manner as in example 1 except that compound P1 was replaced with compound P110 as the hole transport layer material.
Example 10
The organic electroluminescent device in this example was fabricated in the same manner as in example 1 except that compound P1 was replaced with compound P152 as the hole transport layer material.
Example 11
The organic electroluminescent device in this example was fabricated in the same manner as in example 1 except that compound P1 was replaced with compound P170 as a hole transport layer material.
Example 12
The organic electroluminescent device in this example was fabricated in the same manner as in example 1 except that compound P1 was replaced with compound P192 as the hole transport layer material.
Comparative example 1
In this comparative example, an organic electroluminescent device was fabricated in the same manner as in example 1 except that compound P1 was replaced with R-1 as a hole transport material, and the structure of R-1 was as follows:
comparative example 2
In this comparative example, the organic electroluminescent device was fabricated in the same manner as in example 1 except that compound P1 was replaced with R-2 as a hole transporting material, and the structure of R-2 was as follows.
Comparative example 3
In this comparative example, an organic electroluminescent device was fabricated in the same manner as in example 1 except that compound P1 was replaced with R-3 as a hole transporting material, the structure of R-3 being as follows:
the following performance measurements were made for the organic electroluminescent devices prepared in examples 1 to 12 and comparative examples 1 to 3:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples 1 to 12 and comparative examples 1 to 3 and the lifetime of the devices were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 5000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 5000cd/m2The luminance drop of the organic electroluminescent device was measured to be 4750cd/m by maintaining a constant current at luminance2Time in hours. The measurement results are shown in table 1.
Table 1:
as can be seen from the results in Table 1, when the compound of the invention is used in a hole transport material of an organic electroluminescent device, the luminance of the device reaches 5000cd/m2When the hole transport material is used, the driving voltage is low below 6.5V, the current efficiency is as high as more than 13.5cd/A, LT95 is more than 76h, the driving voltage can be effectively reduced, the current efficiency is improved, the service life of the device is prolonged, and the hole transport material is good in performance.
Example 13
The organic electroluminescent device in the examples was prepared as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to<1×10-5Pa, performing vacuum evaporation on the anode layer film to obtain HI-3 serving as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
evaporating HT-4 on the hole injection layer in vacuum to serve as a hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 80 nm;
the compound P1 synthesized in synthesis example 1 is evaporated in vacuum on the hole transport layer to be used as an electron barrier layer material of a device, the evaporation rate is 0.1nm/s, and the total film thickness is 80 nm;
a luminescent layer of the device is vacuum evaporated on the electron blocking layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material GPH-59 is adjusted to be 0.1nm/s, the evaporation rate of the dye RPD-8 is set in a proportion of 3%, and the total film thickness of evaporation is 30nm by using a multi-source co-evaporation method;
vacuum evaporating an electron transport layer material ET-46 of the device on the light emitting layer, wherein the proportion of 50 percent and ET-57, 50 percent are set, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 30 nm;
LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
Example 14
The organic electroluminescent device in this example was fabricated in the same manner as in example 13 except that compound P1 was replaced with compound P4 as an electron blocking layer material.
Example 15
The organic electroluminescent device in this example was fabricated in the same manner as in example 13 except that compound P1 was replaced with compound P8 as an electron blocking layer material.
Example 16
The organic electroluminescent device in this example was fabricated in the same manner as in example 13 except that compound P1 was replaced with compound P16 as an electron blocking layer material.
Example 17
The organic electroluminescent device in this example was fabricated in the same manner as in example 13 except that compound P1 was replaced with compound P28 as an electron blocking layer material.
Example 18
The organic electroluminescent device in this example was fabricated in the same manner as in example 13 except that compound P1 was replaced with compound P43 as an electron blocking layer material.
Example 19
The organic electroluminescent device in this example was fabricated in the same manner as in example 13 except that compound P1 was replaced with compound P83 as an electron blocking layer material.
Example 20
The organic electroluminescent device in this example was prepared in the same manner as in example 13 except that compound P1 was replaced with compound P116 as an electron blocking layer material.
Example 21
The organic electroluminescent device in this example was prepared in the same manner as in example 13 except that compound P1 was replaced with compound P152 as an electron blocking layer material.
Example 22
The organic electroluminescent device in this example was prepared in the same manner as in example 13 except that compound P1 was replaced with compound P178 as an electron blocking layer material.
Example 23
The organic electroluminescent device in this example was fabricated in the same manner as in example 13 except that compound P1 was replaced with compound P193 as an electron blocking layer material.
Comparative example 4
In this comparative example, an organic electroluminescent device was fabricated in the same manner as in example 13 except that compound P1 was replaced with R-1 as an electron blocking material, and the structure of R-1 was as follows.
Comparative example 5
In this comparative example, an organic electroluminescent device was fabricated in the same manner as in example 13 except that compound P1 was replaced with R-2 as an electron blocking material, and the structure of R-2 was as follows.
Comparative example 6
In this comparative example, an organic electroluminescent device was fabricated in the same manner as in example 13 except that compound P1 was replaced with R-3 as an electron blocking material, and the structure of R-3 was as follows.
The following performance measurements were made for the organic electroluminescent devices prepared by the procedures of the above examples 13 to 23 and comparative examples 4 to 6:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples 13 to 23 and comparative examples 4 to 6 and the lifetime of the devices were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 5000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 5000cd/m2The luminance drop of the organic electroluminescent device was measured to be 4750cd/m by maintaining a constant current at luminance2The time (d) is in hours, and the measurement results are shown in Table 2.
TABLE 2
As can be seen from the data in Table 2, when the compound of the invention is used as an electron barrier material of an organic electroluminescent device, the luminance of the device reaches 5000cd/m2When the material is used, the driving voltage is low below 7.5V, the current efficiency is as high as more than 14.5cd/A, LT95 is more than 42h, the driving voltage can be effectively reduced, the current efficiency is improved, the service life of the device is prolonged, and the material is an electron barrier material with good performance.
From the above results, it is clear that the above compound can be used as a hole transport material, and can also be used as an electron blocking layer material in combination with other hole transport materials. The device prepared by the materials has the characteristics of low starting voltage, high performance and long service life. These performance enhancements may be relevant to the particular diamine structure in the parent nucleus of the compounds provided by the present invention.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (13)
1. A compound of the general formula I:
wherein: l is1～L4Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C3-C30 heteroarylene;
Ar1～Ar4each independently selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
X1-X6are each independently selected from CR1、CR2Or CR3And X1、X4And X5At least one of which is not CR1；
R1Is hydrogen, R2One selected from C1-C12 alkyl, C3-C12 cycloalkyl and C1-C12 alkoxy, R3One selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic aromatic hydrocarbon or fused ring aromatic hydrocarbon group, C3-C30 monocyclic heteroaromatic hydrocarbon or fused ring heteroaromatic hydrocarbon group.
2. A compound of formula I, wherein L is1～L4Are all single bonds.
3. A compound of formula I in which X is1、X4And X5At least one of which is CR3。
4. A compound of formula I in which X is1Is CR2Or CR3。
5. A compound of formula I in which X is1Is CR3。
6. Any of claims 1 to 5A compound of the general formula I, wherein X2、X3And X6Are all CR1。
7. A compound of formula I in which X is1、X4And X5One of them is CR3，X1～X6The other five are CR1。
8. A compound of formula I as claimed in any one of claims 4 to 6 wherein X1～X6Middle removing X1The other five are CR1。
9. A compound of formula I as claimed in any one of claims 1 to 8 wherein Ar is1～Ar4Selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothienyl.
10. A compound of formula I as claimed in any one of claims 1 to 8 wherein R is3Selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, dibenzofuranyl, or dibenzothienyl.
11. A compound of formula (la) according to claim 1, selected from the compounds of the following specific structures:
12. use of a compound as claimed in any one of claims 1 to 11 as a hole transport layer material or an electron blocking layer material in an organic electroluminescent device.
13. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between said first and second electrodes, characterized in that said organic layers comprise at least one compound according to any one of claims 1 to 11.
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