CN116082338A - Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device - Google Patents
Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device Download PDFInfo
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- CN116082338A CN116082338A CN202111280697.9A CN202111280697A CN116082338A CN 116082338 A CN116082338 A CN 116082338A CN 202111280697 A CN202111280697 A CN 202111280697A CN 116082338 A CN116082338 A CN 116082338A
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- emitting auxiliary
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- 239000000463 material Substances 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000000376 reactant Substances 0.000 claims description 17
- 238000005406 washing Methods 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 239000012153 distilled water Substances 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000003003 spiro group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000012065 filter cake Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005909 Kieselgur Substances 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 3
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- -1 dibenzofuranyl Chemical group 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- 125000005264 aryl amine group Chemical group 0.000 abstract description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
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- 239000000758 substrate Substances 0.000 description 14
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- 230000000903 blocking effect Effects 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 2
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- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
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- 239000002346 layers by function Substances 0.000 description 2
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- 238000004020 luminiscence type Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- 238000004440 column chromatography Methods 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
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- 239000003208 petroleum Substances 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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Abstract
The invention relates to a luminescent auxiliary material, a preparation method thereof and an organic electroluminescent device, belonging to the field of organic photoelectric luminescent materials, wherein the luminescent auxiliary material has the structural general formula of
The invention uses seven-membered nitrogen-containing impuritiesThe ring is a mother nucleus and is connected with an arylamine group, the obtained compound can be used for organic electroluminescent devices of green light and red light, and the prepared device has the characteristics of high luminous efficiency, low driving voltage, long service life and the like.
Description
Technical Field
The invention relates to the technical field of organic photoelectric luminescent materials, in particular to a luminescent auxiliary material, a preparation method thereof and an organic electroluminescent device.
Background
Along with the rapid development of information technology, new targets and requirements are also put forward on the performance of an information display system, and an organic electroluminescent device (OLED) has high brightness, high resolution, wide viewing angle and low energy consumption, so that the OLED becomes a research hot spot. The requirements of people can be met, meanwhile, the multifunctional flat panel display device has the advantages of wider working temperature, flexible display and the like, and becomes a new generation of flat panel display pet.
The organic light emitting diode generally has the following structure: an anode, a cathode, and an organic material layer interposed therebetween. In order to improve efficiency and stability of the organic EL element, the organic material layer includes a plurality of layers having different materials, such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a light emitting auxiliary layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL). Among them, a layer having a hole transporting function such as a hole injection layer, a hole transport layer, an electron blocking layer, etc. can change hole transport efficiency, light emitting efficiency, lifetime, etc. of holes to a light emitting layer, and has a great influence on performance data of an electronic device.
A light-emitting auxiliary layer (i.e., a plurality of hole transport layers) is typically added between the hole transport layer and the light-emitting layer to improve device lifetime and efficiency. The light-emitting auxiliary layer can play a role in reducing potential barrier between the hole transmission layer and the light-emitting layer and reducing driving voltage of the organic electroluminescent device, and further increases the utilization rate of holes, so that the light-emitting efficiency and the service life of the device are improved, and the driving voltage is reduced. However, the existing functional materials capable of forming the light-emitting auxiliary layer are less, particularly the problems of the OLED such as insignificant life and light-emitting efficiency improvement, low glass transition temperature and the like, so that the development of the organic functional materials with higher performance is particularly important to meet the requirements of panel manufacturing enterprises.
Disclosure of Invention
The invention aims to provide a luminescent auxiliary material, a preparation method thereof and an organic electroluminescent device, so as to solve the problems in the background technology.
In order to achieve the above purpose, the present invention provides the following technical solutions:
a luminescent auxiliary material, the structural general formula of which is formula I:
wherein X is O, S, -CR4R5-, -NR6;
R1-R3 are each independently hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl;
r4 and R5 are each independently substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl;
L 1 is at least one of a bond, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3-to 20-membered heteroaryl group, a substituted or unsubstituted C10-C30 fused ring group, a substituted or unsubstituted C5-C30 spiro ring group;
r6, ar1, ar2 represent a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted 3-to 30-membered heterocycloalkyl group; a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted 3-to 20-membered heteroaryl; at least one of a substituted or unsubstituted C10-C30 fused ring group and a substituted or unsubstituted C5-C30 spiro ring group.
As a further technical scheme of the invention, the heteroatom in the 3-to 30-membered heterocycloalkyl is at least one of N, O, S, si, P, se; the heteroatom in the substituted or unsubstituted 3-to 20-membered heteroaryl is at least one of N, O, S, si, P, se.
As a still further embodiment of the present invention, each of R1 to R3 is independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, alkoxy, phenyl, methylbenzene, biphenyl, naphthyl, terphenyl, butyl, pentyl, hexyl, dibenzofuranyl, dibenzothienyl, phenanthryl, carbazolyl, pyridinyl; R1-R3 are respectively substituted at any position on the benzene ring, and the number of substitution is 0-4.
As a still further aspect of the present invention, the Ar1 and Ar2 are connected to N at any connectable position, and each of Ar1 and Ar2 is independently at least one of the following groups:
as a still further technical scheme of the present invention, the general formula I is one of the following general formulas I-a to I-f:
wherein L is 1 Is one of the following groups:
as a still further technical scheme of the invention, the general formula I-a is one of the following general formulas I-a-1 to I-a-4; the general formula I-f is one of the following general formulas I-f-1 to I-f-4:
as a still further aspect of the present invention, R 4 -R 6 Each independently is methyl, ethyl, phenyl, biphenyl, methylbenzene, naphthyl, or terphenyl.
As a still further aspect of the present invention, the L 1 Is at least one of phenyl, naphthyl, biphenyl, terphenyl and phenanthryl.
A preparation method of a luminescent auxiliary material comprises the following synthetic routes:
when L 1 When the bond is non-chemical bond, the method comprises the following steps: under the protection of N2, respectively adding reactants A-I, reactants B-I, tetra (triphenylphosphine) palladium and potassium carbonate into a solvent formed by mixing toluene, ethanol and water, heating for reaction, cooling to room temperature, after solid precipitation, filtering, washing with water to remove salt, eluting with a small amount of ethanol, and drying a filter cake; recrystallizing in 1, 4-dioxane to obtain luminescent auxiliary material;
when L 1 When the compound is a chemical bond, the method comprises the following steps: after adding reactants A-I and B-II into a reaction vessel and dissolving in toluene, pd2 (dba) 3, P (t-Bu) 3 and t-Buona are added under the atmosphere of nitrogen; after the addition, the reaction temperature is slowly increased and stirred; filtering with diatomaceous earth while hot, removing salt and catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and the solvent was removed using a rotary evaporator to give a luminescent auxiliary material, the synthetic route of which was as follows:
compared with the prior art, the invention has the beneficial effects that: the seven-membered nitrogen-containing heterocycle is used as a parent nucleus to be connected with an arylamine group, the obtained compound can be used for preparing an organic electroluminescent device with green light and red light at the same time, and the prepared device has the characteristics of high luminous efficiency, low driving voltage, long service life and the like.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a luminescent auxiliary material prepared in example 1;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the luminescent auxiliary material prepared in example 2;
fig. 3 is a nuclear magnetic resonance hydrogen spectrum of the light emitting auxiliary material prepared in example 3.
Detailed Description
A luminescent auxiliary material has a structural general formula as shown in the specification:
wherein X is O, S, -CR 4 R 5 -，-NR 6 ；
R 1 -R 3 Each independently is hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl;
R 4 、R 5 each independently is a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C24 aryl group, a substituted or unsubstituted 3-to 30-membered heteroaryl group;
L 1 is at least one of a bond, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3-to 20-membered heteroaryl group, a substituted or unsubstituted C10-C30 fused ring group, a substituted or unsubstituted C5-C30 spiro ring group;
R 6 、Ar 1 、Ar 2 represents a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted 3-to 30-membered heterocycloalkyl group; substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 20-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring group, substituted or unsubstitutedAt least one of the C5-C30 spirocyclic groups of (C).
Preferably, the light emitting auxiliary material is any one of the following structural formulas 1 to 179:
example 1
A preparation method of a luminescent auxiliary material comprises the following synthetic routes:
wherein, the CAS of the reactant A-24 is 2493275-15-1.
The preparation method comprises the following steps: after adding reactant A-24 (30 mmol) and reactant B-24 (36 mmol) to the reaction vessel and dissolving in toluene, pd2 (dba) 3 (0.3 mmol), P (t-Bu) 3 (0.6 mmol), t-BuONa (60 mmol) were added under nitrogen atmosphere; after the addition, the reaction temperature was slowly raised to 105 ℃ and the mixture was stirred for 8h; filtering with diatomaceous earth while hot, removing salt and catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; the combined organic layers were then dried over magnesium sulfate and the solvent was removed using a rotary evaporator; dichloromethane: petroleum ether volume ratio of 1 (1-9) was used as eluent and the remaining material was purified by column chromatography to give compound 24 (18.7 g, yield: 87%).
Compound 24 was characterized as follows:
HPLC purity: > 99.7%;
mass spectrometry test: theoretical value 718.94; the test value is Ms 718.61;
elemental analysis:
theoretical value: c,90.21; h,5.89; n,3.90;
test value: c,90.03; h,6.05; n,4.02;
the nuclear magnetic resonance hydrogen spectrum is shown in figure 1.
Example 2
A preparation method of a luminescent auxiliary material comprises the following synthetic routes:
wherein, CAS for reactant A-132: 2493275-15-1 (same as reactant A-24).
The preparation method comprises the following steps: n (N) 2 Under the protection, adding reactants A-132 (30 mmol), reactants B-132 (36 mmol), tetrakis (triphenylphosphine) palladium (0.45 mmol) and potassium carbonate (66 mmol) into a mixed solvent of toluene, ethanol and water (300 ml:100 ml) respectively, heating to 110 ℃, reacting for 8 hours, cooling to room temperature, after the solid precipitation is finished, filtering, washing with water to remove salt, leaching with a small amount of ethanol, and drying a filter cake; placed in 1, 4-dioxaneRecrystallization gave compound 132 (20.4 g, yield: 90%).
Compound 132 was characterized as follows:
HPLC purity: > 99.8%;
mass spectrometry test: theoretical value 754.98; the test value is Ms 754.72;
elemental analysis:
theoretical value: c,90.68; h,5.61; n,3.71;
test value: c,90.38; h,5.88; n,3.82;
the nuclear magnetic resonance hydrogen spectrum is shown in fig. 2.
Example 3
A preparation method of a luminescent auxiliary material comprises the following synthetic routes:
wherein, CAS for reactant A-150: 2493274-82-9.
The preparation method comprises the following steps: n (N) 2 Under the protection, respectively adding the reactant A-150 (30 mmol), the reactant B-150 (45 mmol), the tetrakis (triphenylphosphine) palladium (0.3 mmol) and potassium carbonate (63 mmol) into a mixed solvent of toluene, ethanol and water (400 ml:100 ml), heating to 115 ℃, reacting for 8 hours, cooling to room temperature, after the solid is precipitated, filtering, washing with water to remove salt, leaching with a small amount of ethanol, and drying a filter cake; recrystallisation from 1, 4-dioxane gave compound 150 (20.7 g, yield: 80%, ms: 861.27).
Compound 150 was characterized as follows:
HPLC purity: > 99.6%;
mass spectrometry test: theoretical value 861.12; the test value is Ms 861.27;
elemental analysis:
theoretical value: c,87.87; h,5.15; n,3.25; s,3.72;
test value: c,87.67; h,5.34; n,3.30; s,3.81;
the nuclear magnetic resonance hydrogen spectrum is shown in fig. 3.
Example 4-example 24
The synthesis of compounds 7, 12, 16, 18, 22, 24, 28, 36, 43, 55, 66, 70, 83, 99, 114, 124, 125, 140, 157, 164, 174 was completed with reference to the synthesis methods of examples 1 to 3; mass spectra, molecular formulas and yields are shown in table 1 below.
TABLE 1
| Examples | Compounds of formula (I) | Molecular formula | Theoretical mass spectrum value | Mass spectrometry test values | Yield% |
| Example 4 | 7 | C 58 H 44 N 2 | 769.00 | 769.23 | 88 |
| Example 5 | 12 | C 60 H 46 N 2 | 795.04 | 795.30 | 81 |
| Example 6 | 16 | C 60 H 45 N 3 | 808.04 | 808.28 | 75 |
| Example 7 | 18 | C 55 H 38 N 2 O | 742.92 | 743.11 | 85 |
| Example 8 | 22 | C 56 H 42 N 2 | 742.97 | 742.75 | 87 |
| Example 9 | 24 | C 54 H 42 N 2 | 718.94 | 718.80 | 90 |
| Example 10 | 28 | C 53 H 38 N 2 | 702.90 | 702.58 | 86 |
| Example 11 | 36 | C 57 H 42 N 2 | 754.98 | 754.77 | 88 |
| Example 12 | 43 | C 69 H 49 N 3 | 920.17 | 920.44 | 72 |
| Example 13 | 55 | C 49 H 34 N 2 S | 682.89 | 683.09 | 83 |
| Example 14 | 66 | C 56 H 34 N 2 O 2 | 766.90 | 766.71 | 78 |
| Example 15 | 70 | C 63 H 43 N 3 O | 858.06 | 858.24 | 82 |
| Example 16 | 83 | C 56 H 36 N 2 O | 752.92 | 752.84 | 85 |
| Example 17 | 99 | C 54 H 35 N 3 O | 741.89 | 741.66 | 83 |
| Example 18 | 114 | C 63 H 45 N 3 | 844.07 | 844.07 | 87 |
| Example 19 | 124 | C 66 H 48 N 2 | 869.12 | 869.34 | 75 |
| Example 20 | 125 | C 57 H 42 N 2 | 754.98 | 755.31 | 86 |
| Example 21 | 140 | C 66 H 49 N 3 | 884.14 | 884.41 | 74 |
| Example 22 | 157 | C 61 H 41 N 3 O | 832.02 | 832.17 | 80 |
| Example 23 | 164 | C 63 H 45 N 3 | 844.07 | 844.31 | 81 |
| Example 24 | 174 | C 55 H 40 N 2 | 728.94 | 729.10 | 72 |
Further, since other compounds of the present application can be obtained by referring to the synthetic methods of the examples listed above, they are not listed here.
Application example 1
The preparation method of the red light organic electroluminescent device comprises the following steps:
a. ITO anode: washing an ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, washing by ultrasonic waves for 30min, repeatedly washing by distilled water for 2 times, washing by ultrasonic waves for 10min, transferring into a spin dryer for spin drying after washing, baking for 2 hours at 220 ℃ by a vacuum oven, and cooling after baking is finished, so that the glass substrate can be used; using the substrate as an anode, and using an evaporator to perform an evaporation device process, and evaporating other functional layers on the substrate in sequence;
b. HIL (hole injection layer): to be used for
Vacuum evaporating cavity injection layer materials HT and P-dock, the chemical formula of which is shown as follows; the evaporation rate ratio of HT to P-dock is 97:3, the thickness is 10nm;
c. HTL (hole transport layer): to be used for
Vacuum evaporating 125nm HT as a hole transport layer on the hole injection layer;
d. light-emitting auxiliary layer: to be used for
Vacuum evaporating 100nm of the compound provided in example 1 above as a light-emitting auxiliary layer on top of the hole transport layer;
e. EML (light emitting layer): then on the light-emitting auxiliary layer to
A Host material (Host) and a Dopant material (Dopant) having a thickness of 40nm were vacuum-evaporated as light-emitting layers, the chemical formulas of Host and Dopant being as follows; wherein the evaporation rate ratio of Host to Dopant is 97:3, a step of;
f. HB (hole blocking layer): to be used for
Vacuum evaporating a hole blocking layer with the thickness of 5.0 nm;
g. ETL (electron transport layer): to be used for
ET and Liq with a thickness of 30nm are vacuum-evaporated as electron transport layers, and the chemical formula of ET is shown below; wherein the evaporation rate ratio of ET to Liq is 50:50;
h. EIL (electron injection layer): to be used for
Evaporating Yb film layer with a thickness of 1.0nm to form an electron injection layer;
i. and (3) cathode: to be used for
The vapor deposition rate ratio of magnesium and silver is 18nm, and the vapor deposition rate ratio is 1:9, so that a cathode is formed;
j. light extraction layer: to be used for
CPL with the thickness of 70nm is vacuum deposited on the cathode to be used as a light extraction layer;
k. and packaging the substrate subjected to evaporation. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
The prepared red light organic electroluminescent device structure and the raw materials during preparation are as follows:
ITO/Ag/ITO/HT P-dose (10 nm)/HT (125 nm)/Compound 1 (100 nm)/Host-R dose-R (40 nm)/HB (5 nm)/ET: liq (30 nm)/Yb (1 nm)/Mg: ag (18 nm)/CPL (70 nm);
application examples 2 to 117
The organic electroluminescent devices of application examples 2 to 117 were prepared according to the above-described method for preparing a red organic electroluminescent device, except that compound 1 of application example 1 was replaced with the corresponding compound, respectively, to form a light-emitting auxiliary layer.
Comparative examples 1 to 8
An organic electroluminescent device was prepared according to the above-described method for preparing a red organic electroluminescent device in application example 1, except that compound 1 in application example 1 was replaced with comparative compounds 1 to 8, wherein the structural formulae of comparative compounds 1 to 8 are as follows:
the organic electroluminescent devices obtained in examples 1 to 117 and comparative examples 1 to 8 above were characterized in terms of driving voltage, luminous efficiency, and lifetime at 6000 (nits) luminance, and the test results are shown in table 2 below:
TABLE 2 luminescence property test results (brightness value 6000 nits)
As can be seen from table 2, the organic electroluminescent devices prepared using the light-emitting auxiliary materials provided by the present invention have improved light-emitting efficiency and lifetime at driving voltage, compared with the conventional organic electroluminescent devices provided by comparative examples 1 to 8.
Application example 118
The preparation method of the green light organic electroluminescent device comprises the following steps:
a. ITO anode: washing an ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, washing by ultrasonic waves for 30min, repeatedly washing by distilled water for 2 times, washing by ultrasonic waves for 10min, transferring into a spin dryer for spin drying after washing, baking for 2 hours at 220 ℃ by a vacuum oven, and cooling after baking is finished, so that the glass substrate can be used; using the substrate as an anode, and using an evaporator to perform an evaporation device process, and evaporating other functional layers on the substrate in sequence;
b. HIL (hole injection layer): to be used for
Vacuum evaporating cavity injection layer materials HT and P-dock, the chemical formula of which is shown as follows; the evaporation rate ratio of HT to P-dock is 97:3, the thickness is 10nm;
c. HTL (hole transport layer): to be used for
Vacuum evaporating 120nm HT as a hole transport layer on the hole injection layer;
d. light-emitting auxiliary layer: to be used for
The compound 1 provided in the above example was vacuum-evaporated as a light-emitting auxiliary layer on top of the hole transport layer at 45 nm;
e. EML (light emitting layer): then on the light-emitting auxiliary layer to
Host materials (Host-G1 and Host-G2) and doping materials (Dopant) with thickness of 400nm are vacuum evaporated as light-emitting layers, wherein Host-G1 and Host-G2 are co-evaporated with doping materials as double Host materials, and the ratio of Host-G1 to Host-G2 is 50%:50, the chemical formulas of Host-G1, host-G2 and Dopant are shown below; wherein the evaporation rate ratio of the host material and the Dopant is 88:12;
f. HB (hole blocking layer): to be used for
Vacuum evaporating a hole blocking layer with the thickness of 5.0 nm;
g. ETL (electron transport layer): to be used for
ET and Liq with a thickness of 30nm are vacuum-evaporated as electron transport layers, and the chemical formula of ET is shown below; wherein the evaporation rate ratio of ET to Liq is 50:50;
h. EIL (electron injection layer): to be used for
The vapor deposition rate of Yb film layer is 1.0nm,forming an electron injection layer;
i. and (3) cathode: to be used for
The vapor deposition rate ratio of magnesium and silver is 18nm, and the vapor deposition rate ratio is 1:9, so that a cathode is formed;
j. light extraction layer: to be used for
CPL with the thickness of 70nm is vacuum deposited on the cathode to be used as a light extraction layer;
k. and packaging the substrate subjected to evaporation. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
The prepared green light organic electroluminescent device structure and the raw materials during preparation are as follows: :
ITO/Ag/ITO/HT P-dose (10 nm)/HT (120 nm)/Compound 1 (45 nm)/(Host-G1+host-G2)/(Host-G (400 nm)/HB (5 nm)/ET: liq (30 nm)/Yb (1 nm)/Mg: ag (18 nm)/CPL (70 nm);
application examples 119 to 165
The organic electroluminescent devices of application examples 119 to 165 were prepared according to the above-described method for preparing a green organic electroluminescent device, except that compound 1 in application example 118 was replaced with the corresponding compound, respectively, to form a light-emitting auxiliary layer.
Comparative examples 9 to 16
An organic electroluminescent device was fabricated according to the above-described method for fabricating a green organic electroluminescent device in application example 118, except that compound 1 in application example 118 was replaced with comparative compounds 1 to 8, wherein the structural formulae of comparative compounds 1 to 8 are shown in comparative examples 1 to 8.
The organic electroluminescent devices obtained in the above device application examples 118 to 165 and device comparative examples 9 to 16 were characterized in terms of driving voltage, luminous efficiency and lifetime at 15000 (nits) luminance, and the test results are shown in table 3 below:
TABLE 3 luminescence property test results (luminance value 15000 nits)
As can be seen from table 3, the organic electroluminescent devices prepared using the light-emitting auxiliary materials provided by the present invention have improved light-emitting efficiency and lifetime at driving voltages, compared to the conventional organic electroluminescent devices provided by comparative examples 9 to 16.
For a red light device, the efficiency of the top emission device system provided by the invention can be generally improved by 4-6%, and the individual efficiency can reach 7%, and the efficiency of the top emission device system is obviously improved for the collocation of the device.
For green light devices, the efficiency of the top emission device system provided by the invention can be generally improved by 4-7%, and for the collocation of the devices, the efficiency is obviously improved.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential characteristics thereof. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.
Furthermore, it should be understood that although the present disclosure describes embodiments, not every embodiment is provided with a separate embodiment, and that this description is provided for clarity only, and that the disclosure is not limited to the embodiments described in detail below, and that the embodiments described in the examples may be combined as appropriate to form other embodiments that will be apparent to those skilled in the art.
Claims (10)
1. The luminous auxiliary material is characterized by having a structural general formula of formula I:
wherein X is O, S, -CR 4 R 5 -，-NR 6 ；
R 1 -R 3 Each independently is hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl;
R 4 、R 5 each independently is a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C24 aryl group, a substituted or unsubstituted 3-to 30-membered heteroaryl group;
L 1 is a bond, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3-to 20-membered heteroaryl group, a substituted or unsubstituted C10-C30 fused ring group, a substituted or unsubstituted C5-C30 spiro ring groupOne less;
R 6 、Ar 1 、Ar 2 represents a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted 3-to 30-membered heterocycloalkyl group; a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted 3-to 20-membered heteroaryl; at least one of a substituted or unsubstituted C10-C30 fused ring group and a substituted or unsubstituted C5-C30 spiro ring group.
2. The light-emitting auxiliary material according to claim 1, wherein a heteroatom in the 3-to 30-membered heterocycloalkyl group is at least one of N, O, S, si, P, se; the heteroatom in the substituted or unsubstituted 3-to 20-membered heteroaryl is at least one of N, O, S, si, P, se.
3. The light-emitting auxiliary material according to claim 1, wherein the R 1 -R 3 Each independently is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, alkoxy, phenyl, methylbenzene, biphenyl, naphthyl, terphenyl, butyl, pentyl, hexyl, dibenzofuranyl, dibenzothiophenyl, phenanthryl, carbazolyl, pyridinyl; r is R 1 -R 3 Each substituted at any position on the benzene ring, the number of substitution is 0-4.
4. A light-emitting auxiliary material according to claim 1, characterized in that: the Ar is as follows 1、 Ar 2 Is connected with N at any connectable position, ar 1 、Ar 2 Each independently is at least one of the following groups:
5. the light-emitting auxiliary material according to claim 1, wherein the general formula I is one of the following general formulae I-a to I-f:
wherein L is 1 Is one of the following groups:
6. the light-emitting auxiliary material according to claim 5, wherein the general formula I-a is one of the following general formulae I-a-1 to I-a-4; the general formula I-f is one of the following general formulas I-f-1 to I-f-4:
7. the light-emitting auxiliary material according to claim 5, wherein R 4 -R 6 Each independently is methyl, ethyl, phenyl, biphenyl, methylbenzene, naphthyl, or terphenyl; the L is 1 Is at least one of phenyl, naphthyl, biphenyl, terphenyl and phenanthryl.
8. The light-emitting auxiliary material according to claim 5, wherein the light-emitting auxiliary material has a chemical formula of any one of formulas 1 to 179:
9. a method for preparing a luminescent auxiliary material as claimed in any one of claims 1 to 8, wherein when L 1 When the compound is a chemical bond, the method comprises the following steps:
after adding reactants A-I and B-I into a reaction vessel and dissolving in toluene, pd2 (dba) 3, P (t-Bu) 3 and t-Buona are added under the atmosphere of nitrogen; after the addition, the reaction temperature is slowly increased and stirred; filtering with diatomaceous earth while hot, removing salt and catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate, washing, separating to obtain organic phase, and extracting water phase with ethyl acetate; drying the combined organic layers by using magnesium sulfate, and removing the solvent by using a rotary evaporator to obtain a light-emitting auxiliary material;
when L 1 When the bond is non-chemical bond, the method comprises the following steps:
under the protection of N2, respectively adding reactants A-I, reactants B-II, tetra (triphenylphosphine) palladium and potassium carbonate into a solvent formed by mixing toluene, ethanol and water, heating for reaction, cooling to room temperature, after solid precipitation, filtering, washing with water to remove salt, eluting with a small amount of ethanol, and drying a filter cake; recrystallizing in 1, 4-dioxane to obtain luminescent auxiliary material;
the structures of the reactants A-I, B-I and B-II are respectively as follows:
10. an organic electroluminescent device comprising a first electrode, a second electrode opposite to the first electrode, and 1 or more organic layers between the first electrode and the second electrode, wherein at least 1 of the organic layers comprises the light-emitting auxiliary material according to any one of claims 1 to 8.
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| KR20200118281A (en) * | 2019-04-04 | 2020-10-15 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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| CN107108623A (en) * | 2014-12-23 | 2017-08-29 | 默克专利有限公司 | Heterocyclic compound with the tall and erect structure of dibenzazepine |
| KR20200118281A (en) * | 2019-04-04 | 2020-10-15 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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