CN117946664A - Anthracene-based compound-containing composition and organic electroluminescent device comprising same - Google Patents
Anthracene-based compound-containing composition and organic electroluminescent device comprising same Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 84
- 239000000203 mixture Substances 0.000 title claims abstract description 51
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 41
- 125000004431 deuterium atom Chemical group 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 15
- -1 1-methylcyclopentyl Chemical group 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 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 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000006738 (C6-C20) heteroaryl group Chemical group 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
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims 2
- 239000010410 layer Substances 0.000 description 45
- 238000001704 evaporation Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a composition containing an anthracene-based compound and an organic electroluminescent device containing the same. The composition comprises at least two compounds with structures shown in a formula I; the composition is used as a material of a luminescent layer of an organic electroluminescent device. According to the invention, through designing the structure of the compound and adopting the composition with specific composition as the material of the light-emitting layer of the OLED light-emitting device, the OLED light-emitting device has lower driving voltage, higher current efficiency and longer service life.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a composition containing an anthracene-based compound and an organic electroluminescent device containing the composition.
Background
Organic electroluminescent devices (OLEDs) have simpler structures, various processing advantages, higher brightness, excellent viewing angle characteristics, faster response speed, and lower driving voltage than other flat panel displays (e.g., liquid Crystal Displays (LCDs), plasma Display Panels (PDPs), field Emission Displays (FEDs), etc.), and thus have been fully developed for use as light sources of flat panel displays (e.g., wall-mounted TVs, etc.), or as backlight units of displays, illuminators, advertisement boards, etc.
The organic electroluminescent device has the following structure: an anode, a cathode, and an organic layer therebetween. In order to improve efficiency and stability of the organic electroluminescent 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 hole blocking layer, a light emitting layer, an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL). Currently, organic electroluminescence has become a mainstream display technology, and accordingly, various novel OLED materials have been developed.
In order to meet the higher demands of OLED devices, there is a need in the art to develop more kinds of materials to improve the performance of OLED devices in terms of current efficiency, lifetime, etc.
Disclosure of Invention
In view of the shortcomings of the prior art, the invention aims to provide a composition containing an anthracene-based compound and an organic electroluminescent device containing the same. According to the invention, through designing the structure of the compound and adopting the composition with specific composition as the material of the light-emitting layer of the OLED light-emitting device, the OLED light-emitting device has lower driving voltage, higher current efficiency and longer service life.
To achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a composition comprising at least two compounds each having a structure as shown in formula I;
Wherein Ar 11、Ar12 is independently selected from any one of substituted or unsubstituted phenyl, naphthyl or biphenyl;
x is selected from O or S;
the substituent groups of Ar 11、Ar12 are at least one of-F, -CN, C1-C12 alkyl, C1-C12 alkoxy, C6-C20 aryl and C6-C20 heteroaryl independently;
the compound of formula I meets at least one of the following conditions:
(1) The compound shown in the formula I does not contain deuterium atoms;
(2) The hydrogen atoms of at least one of the substituents in Ar 11 are all substituted with deuterium atoms;
(3) The hydrogen atoms of at least one of the substituents in Ar 12 are all substituted with deuterium atoms;
(4) At least one hydrogen atom in Ar 11 is substituted by deuterium atoms;
(5) At least one hydrogen atom in Ar 12 is substituted by deuterium atoms;
(6) The hydrogen atoms of ring a are all substituted with deuterium atoms;
(7) The hydrogen atoms of ring B are all substituted by deuterium atoms;
(8) The hydrogen atoms of ring C are all substituted by deuterium atoms;
(9) The hydrogen atoms of ring E are all substituted with deuterium atoms.
According to the invention, through designing the structure of the compound, the compound with a specific structural formula is further selected for common use, and the composition is used as a material of a light-emitting layer of the OLED light-emitting device, so that the OLED light-emitting device has lower driving voltage, higher current efficiency and longer service life.
In the present invention, the substituents substituted in Ar 11、Ar12 are each independently selected from at least one of-F, -CN, C1-C12 (e.g., C1, C2, C5, C6, C8, C10, or C12, etc.) alkyl, C1-C12 (e.g., C1, C2, C5, C6, C8, C10, or C12, etc.) alkoxy, C6-C20 (e.g., C6, C7, C10, C12, C18, or C20) aryl, C6-C20 (e.g., C6, C7, C10, C12, C18, or C20) heteroaryl.
The following is a preferred technical scheme of the present invention, but not a limitation of the technical scheme provided by the present invention, and the following preferred technical scheme can better achieve and achieve the objects and advantages of the present invention.
As a preferred embodiment of the present invention, the composition comprises at least one compound of formula I satisfying any one of the conditions (2) to (9).
Preferably, the compound of formula I is selected from the group consisting of the compounds of formula I-1 and the compounds of formula I-2:
Wherein Ar 11、Ar12 has the same protection range as the above;
preferably, the compound of formula I is selected from the group consisting of the compounds of formula I-3 and the compounds of formula I-4:
Wherein Ar 11、Ar12 has the same protection scope as described above.
As a preferred embodiment of the present invention, one of Ar 11、Ar12 is selected from phenyl.
Preferably, one of Ar 11、Ar12 is biphenyl.
Preferably, ar 11、Ar12 is selected from phenyl.
Preferably, ar 11、Ar12 is selected from biphenyl.
Preferably, the substituents of the substituents in Ar 11、Ar12 are each independently selected from at least one of-F, -CN, methyl, ethyl, t-butyl, adamantyl, cyclohexyl, cyclopentyl, 1-methylcyclopentyl, 1-methylcyclohexyl, methoxy, phenyl, biphenyl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl or naphthyl.
As a preferred embodiment of the present invention, the compound of formula I is selected from any one of the following substituted or unsubstituted compounds:
Wherein, the substitution means that the hydrogen atoms in the above compounds can be substituted by deuterium atoms independently. In the above-mentioned compound, D is a deuterium atom (the same applies hereinafter).
As a preferred embodiment of the present invention, the composition further comprises a compound having a structure as shown in formula II:
Wherein R 21、R22 and R 23 are each independently selected from any one of hydrogen, C1-C12 (e.g., may be C1, C2, C4, C6, C8, C10, or C12, etc.) linear or branched alkyl, C6-C12 (e.g., may be C6, C7, C8, C9, C10, C11, or C12) cycloalkyl, -NAr 23Ar24;
Ar 21、Ar22、Ar23、Ar24 is independently selected from any one of substituted or unsubstituted C6-C20 (for example, C6, C8, C10, C12, C14, C16, C18 or C20) aryl, substituted or unsubstituted C3-C20 (for example, C3, C6, C8, C10, C12, C14, C16, C18 or C20) heteroaryl;
The substituents substituted in Ar 21、Ar22、Ar23、Ar24 are each independently selected from C1-C5 straight or branched alkyl (e.g., methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, etc.) or C6-C12 aryl (e.g., phenyl, toluyl, naphthyl, etc.).
As a preferred embodiment of the present invention, ar 21、Ar22、Ar23、Ar24 is each independently selected from the group consisting of Any of which, the dotted line indicates the attachment site.
Preferably, R 21、R22 and R 23 are each independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl or adamantyl.
Preferably, the compound of formula II is selected from any one of the following compounds:
As a preferred embodiment of the present invention, the composition further comprises a compound having the formula III:
Wherein Ar 31、Ar32、Ar33 and Ar 34 are each independently selected from any of substituted or unsubstituted C6-C22 aryl (e.g., which may be C6, C8, C10, C12, C14, C16, C18, or C20, etc.), substituted or unsubstituted C12-C40 heteroaryl (e.g., which may be C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.);
r 31 is selected from any one of phenyl, naphthyl or biphenyl;
a is selected from 0 or 1;
the substituents substituted in Ar 31、Ar32、Ar33、Ar34 are each independently selected from C1-C5 straight or branched alkyl (e.g., methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, etc.) or C6-C12 aryl (e.g., phenyl, etc.).
Preferably, each of Ar 31、Ar32、Ar33 and Ar 34 is independently selected from Any one or a combination of at least two, the dotted line represents the ligation site.
Preferably, the compound of formula III is selected from any one of the following compounds:
in a second aspect, the present invention provides a compound comprising any one of the following compounds:
the compound is used for preparing the composition according to the first aspect.
In the above-mentioned compound, D is a deuterium atom.
In a third aspect, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;
the material of the organic thin film layer comprises the composition according to the first aspect.
Preferably, the organic thin film layer includes a light emitting layer;
the material of the light emitting layer comprises the composition according to the first aspect.
In a fourth aspect, the present invention provides a display device comprising an organic electroluminescent device as described in the third aspect.
Compared with the prior art, the invention has the following beneficial effects:
According to the invention, the specific composition of the composition is designed, and the compound with a specific structural formula is selected for common use, so that the OLED light-emitting device has lower driving voltage, higher current efficiency and longer service life by taking the composition as a main material of a light-emitting layer of the OLED light-emitting device.
Detailed Description
To facilitate understanding of the present invention, examples are set forth below. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Synthesis example 1
This synthetic example provides compound BH3 and a method of synthesizing the same, as follows:
100mL of toluene, 20mL of ethanol and 10mL of water are sequentially added into a 250mL three-necked flask under the protection of nitrogen, BH3-1 (3.5 g), BH3-2 (3.0 g), sodium carbonate (2.1 g) and tetraphenylphosphine palladium (0.15 g) are added, the temperature is slowly increased to reflux reaction for 8h, the temperature is reduced to room temperature, water is added, an organic layer is washed with water, magnesium sulfate is dried, after the magnesium sulfate is removed by filtration, a solvent is removed by decompression, silica gel column chromatography separation is performed, petroleum ether: ethyl acetate: dichloromethane=10:1:0.2 (volume ratio) to give compound BH3 (3.9 g).
Mass spectrometry detection of compound BH 3: the mass to charge ratio (m/z) was measured to be 514.17.
Synthesis examples 2 to 7
Synthetic examples 2-7 provide a compound and a synthetic method thereof, respectively, the synthetic method of the compound referring to the synthetic method of the compound BH3 in example 1, except that the corresponding compound is synthesized using the corresponding bromo-and boric acid-based compounds (see table 1 for details); and mass spectrometry detection is carried out on the synthesized compound, and the mass-to-charge ratio (m/z) of the compound is measured as shown in the following table 1.
TABLE 1
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Other compounds not specifically identified as synthetic steps may be prepared by the general knowledge in the art, in combination with the above examples.
The specific structures of the compounds used in the following device examples and device comparative examples are as follows:
the specific structures of the compounds employed in the examples below are shown below:
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Device example 1
The embodiment of the device provides an organic electroluminescent device, and the structure of the organic electroluminescent device is ITO/HT (40 nm)/luminescent layer (30 nm): BD-1 (3%)/TPBI (30 nm)/LiF (0.5 nm)/Al (150 nm);
the preparation method of the organic electroluminescent device comprises the following steps:
(1) Carrying out ultrasonic treatment on a glass substrate coated with an ITO transparent conductive layer (serving as an anode) in a cleaning agent, then flushing in deionized water, then carrying out ultrasonic degreasing in a mixed solvent of acetone and ethanol, drying in a clean environment to remove water completely, cleaning with ultraviolet light and ozone, bombarding the surface with a low-energy cation beam to improve the property of the ITO surface and improve the bonding capability with a hole injection layer;
(2) Placing the glass substrate in a vacuum cavity, vacuumizing to 1X 10 -5～1×10-4 Pa, and vacuum evaporating HT on an anode to serve as a hole transport layer, wherein the evaporation rate is 0.01nm/s, and the thickness of an evaporation film is 40nm;
(3) Vacuum evaporating a light-emitting layer on the hole transport layer, wherein the evaporation rate is 0.01nm/s, the total evaporation film thickness is 30nm, the main materials of the light-emitting layer comprise BH5 and BH5-D (the volume ratio of the main materials is 1:1), the doping material is BD-1, and the volume ratio of the main materials of the light-emitting layer to the doping material is 100:3; when the main materials of the luminous layer are more than two substances, respectively placing different main materials in different evaporation sources, and controlling the evaporation speed of the different main materials so that the mixture with different volume ratios is used as the main materials of the luminous layer in the organic electroluminescent device;
(4) Vacuum evaporating TPBI on the organic light-emitting layer to serve as an electron transport layer of the organic electroluminescent device; the vapor deposition rate is 0.01nm/s, and the total film thickness of vapor deposition is 30nm;
(5) And vacuum evaporating LiF with the wavelength of 0.5nm and Al with the wavelength of 150nm on the electron transport layer to serve as an electron injection layer and a cathode, so as to obtain the organic electroluminescent device.
Device examples 2 to 11
Device examples 2-11 each provided an organic electroluminescent device differing from device example 1 only in that the luminescent layer host materials were different in specific composition as shown in table 2 below, the volume ratio of each compound in the luminescent layer host materials was the same (the volume ratio of two compounds was 1:1 if the luminescent layer host materials were two compounds, the volume ratio of three compounds was 1:1:1 if the luminescent layer host materials were three compounds), and other structures, materials, and preparation methods were the same as device example 1.
Device comparative examples 1 to 5
Device comparative examples 1to 5 each provided an organic electroluminescent device differing from device example 1 only in that the host material of the light-emitting layer was different in specific composition as shown in table 2 below, the volume ratio of each compound in the host material of the light-emitting layer was 1:1, and the other structures, materials and preparation methods were the same as those of device example 1.
Performance test:
The OLED-1000 multichannel accelerated aging life and photochromic performance analysis system manufactured in Hangzhou is used for testing the driving voltage, the current efficiency and the life LT90 of the organic electroluminescent device; the LT90 is the time required for maintaining the current density at the initial luminance of 2000nit and decreasing the luminance to 90% of the original luminance, and the specific test results are shown in table 2, wherein the driving voltage, the current efficiency, and the LT90 are all relative values.
TABLE 2
Note that: in table 2 "/" indicates that the host material of the light-emitting layer of the device example or the device comparative example does not contain the compound.
As can be seen from the contents of table 2, the specific composition of the composition is designed, and the compound with a specific structural formula is used together, so that the composition is used as a main material of a light-emitting layer of the OLED light-emitting device, and the OLED light-emitting device has lower driving voltage, higher current efficiency and longer service life.
As can be seen from device examples 1, 4, 6-11 and device examples 2-3, 5, the OLED device prepared by controlling the composition to contain at least one compound containing deuterium atoms has more excellent comprehensive properties.
As can be seen from the device examples 1-9 and the device examples 10-11, the invention can further improve the service life of the OLED by selecting three compounds of formula I to form a composition, and using the composition as a main body material of the light-emitting layer of the OLED device through the cooperation of the three compounds.
As is apparent from the device examples 1 to 11 and the device comparative examples 1 to 2 and 5, the OLED light-emitting device can have a lower driving voltage, a higher current efficiency and a longer lifetime by selecting a compound having a specific structure to form a composition and using the composition as a host material for a light-emitting layer of the OLED light-emitting device.
As can be seen from device examples 1-11 and device comparative examples 3-4, OLED devices having more excellent overall properties can be prepared by selecting at least two compounds of formula I to form a composition in the present invention.
Device examples 12 to 13
Device examples 12-13 each provided an organic electroluminescent device differing from device example 1 only in that BD-2 was used instead of BD-1, and in addition, the light-emitting layer host materials were different in specific composition as shown in Table 3 below, the volume ratio of each compound in the light-emitting layer host materials was 1:1, and the other structures, materials and preparation methods were the same as those of device example 1.
Device comparative examples 6 to 7
Device comparative examples 6 to 7 each provided an organic electroluminescent device differing from device example 12 only in that the host material of the light-emitting layer was different in specific composition as shown in table 3 below, the volume ratio of each compound in the host material of the light-emitting layer was 1:1, and the other structures, materials and preparation methods were the same as those of device example 12.
Performance test:
The OLED-1000 multichannel accelerated aging life and photochromic performance analysis system manufactured in Hangzhou is used for testing the driving voltage, the current efficiency and the life LT90 of the organic electroluminescent device; the LT90 is the time required for maintaining the current density at the initial luminance of 2000nit and decreasing the luminance to 90% of the original luminance, and the specific test results are shown in table 2, wherein the driving voltage, the current efficiency, and the LT90 are all relative values.
TABLE 3 Table 3
As can be seen from the contents of table 3, the compound of the structure shown in the formula I with a specific structure is used together with the compound of the structure shown in the formula III to obtain a composition, and the composition is used as a main material of a light emitting layer of an OLED light emitting device, so that the OLED light emitting device has a lower driving voltage, a higher current efficiency and a longer service life.
The applicant states that the detailed process flow of the present invention is illustrated by the above examples, but the present invention is not limited to the above detailed process flow, i.e. it does not mean that the present invention must be implemented depending on the above detailed process flow. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (10)
1. A composition comprising an anthracene-based compound, wherein the composition comprises at least two compounds each having a structure according to formula I;
Wherein Ar 11、Ar12 is independently selected from any one of substituted or unsubstituted phenyl, naphthyl or biphenyl;
x is selected from O or S;
the substituent groups of Ar 11、Ar12 are at least one of-F, -CN, C1-C12 alkyl, C1-C12 alkoxy, C6-C20 aryl and C6-C20 heteroaryl independently;
the compound of formula I meets at least one of the following conditions:
(1) The compound shown in the formula I does not contain deuterium atoms;
(2) The hydrogen atoms of at least one of the substituents in Ar 11 are all substituted with deuterium atoms;
(3) The hydrogen atoms of at least one of the substituents in Ar 12 are all substituted with deuterium atoms;
(4) At least one hydrogen atom in Ar 11 is substituted by deuterium atoms;
(5) At least one hydrogen atom in Ar 12 is substituted by deuterium atoms;
(6) The hydrogen atoms of ring a are all substituted with deuterium atoms;
(7) The hydrogen atoms of ring B are all substituted by deuterium atoms;
(8) The hydrogen atoms of ring C are all substituted by deuterium atoms;
(9) The hydrogen atoms of ring E are all substituted with deuterium atoms.
2. The composition according to claim 1, wherein at least one compound of formula I satisfying any one of conditions (2) to (9) is included in the composition;
preferably, the compound of formula I is selected from the group consisting of the compounds of formula I-1 and the compounds of formula I-2:
wherein Ar 11、Ar12 has the same protective range as claim 1;
preferably, the compound of formula I is selected from the group consisting of the compounds of formula I-3 and the compounds of formula I-4:
Wherein Ar 11、Ar12 has the same protective scope as claim 1.
3. The composition according to claim 1 or 2, wherein one of Ar 11、Ar12 is selected from phenyl;
Preferably, one of Ar 11、Ar12 is biphenyl;
Preferably, ar 11、Ar12 is selected from phenyl;
preferably, ar 11、Ar12 is selected from biphenyl;
Preferably, the substituents of the substituents in Ar 11、Ar12 are each independently selected from at least one of-F, -CN, methyl, ethyl, t-butyl, adamantyl, cyclohexyl, cyclopentyl, 1-methylcyclopentyl, 1-methylcyclohexyl, methoxy, phenyl, biphenyl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl or naphthyl.
4. A composition according to any one of claims 1 to 3, wherein the compound of formula I is selected from any one of the following substituted or unsubstituted compounds:
wherein, the substitution means that the hydrogen atoms in the above compounds can be substituted by deuterium atoms independently.
5. The composition of any one of claims 1-4, further comprising a compound having a structure according to formula II:
Wherein R 21、R22 and R 23 are each independently selected from any one of hydrogen, C1-C12 straight or branched alkyl, C6-C12 cycloalkyl and NAr 23Ar24;
ar 21、Ar22、Ar23、Ar24 is independently selected from any one of substituted or unsubstituted C6-C20 aryl and substituted or unsubstituted C3-C20 heteroaryl;
The substituents mentioned for Ar 21、Ar22、Ar23、Ar24 are each independently selected from C1-C5 straight-chain or branched alkyl or C6-C12 aryl.
6. The composition of claim 5, wherein each Ar 21、Ar22、Ar23、Ar24 is independently selected from the group consisting of Any of which, the dotted line represents the ligation site;
Preferably, each of R 21、R22 and R 23 is independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl or adamantyl.
7. The composition of any one of claims 1-6, further comprising a compound having a structure according to formula III:
Wherein Ar 31、Ar32、Ar33 and Ar 34 are each independently selected from any one of substituted or unsubstituted C6-C22 aryl, substituted or unsubstituted C12-C40 heteroaryl;
r 31 is selected from any one of phenyl, naphthyl or biphenyl;
a is selected from 0 or 1;
The substituents substituted in Ar 31、Ar32、Ar33、Ar34 are each independently selected from C1-C5 straight or branched alkyl or C6-C12 aryl;
Preferably, each of Ar 31、Ar32、Ar33 and Ar 34 is independently selected from Any one or a combination of at least two, the dotted line represents the ligation site.
8. A compound, characterized in that the compound comprises any one of the following compounds:
The compound is used for preparing the composition as claimed in any one of claims 1 to 7.
9. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;
The material of the organic thin film layer comprising the composition of any one of claims 1 to 7;
preferably, the organic thin film layer includes a light emitting layer;
A material of the light emitting layer comprising the composition of any one of claims 1-7.
10. A display device characterized in that the display device comprises the organic electroluminescent device according to claim 9.
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| CN202211260977.8A CN117946664A (en) | 2022-10-14 | 2022-10-14 | Anthracene-based compound-containing composition and organic electroluminescent device comprising same |
| PCT/CN2023/121169 WO2024078314A1 (en) | 2022-10-14 | 2023-09-25 | Anthryl-compound-containing composition and organic electroluminescent device comprising same |
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| KR102637961B1 (en) * | 2018-04-03 | 2024-02-19 | 에스에프씨 주식회사 | organic light-emitting diode with High efficiency |
| KR102144446B1 (en) * | 2019-01-21 | 2020-08-13 | 에스에프씨주식회사 | Organic Compound for organic light emitting diode and an organic light emitting diode including the same with long life |
| KR20210033434A (en) * | 2019-09-18 | 2021-03-26 | 주식회사 엘지화학 | Organic light emitting device |
| CN114175296A (en) * | 2019-11-05 | 2022-03-11 | 株式会社Lg化学 | Organic light emitting device |
| US20230092585A1 (en) * | 2019-11-29 | 2023-03-23 | Lg Chem, Ltd. | Organic light-emitting device |
| WO2022039365A1 (en) * | 2020-08-21 | 2022-02-24 | 주식회사 엘지화학 | Organic light-emitting device comprising organic compound |
| CN115968592A (en) * | 2020-12-24 | 2023-04-14 | 株式会社Lg化学 | Organic light emitting device comprising organic compound |
| US20240122063A1 (en) * | 2021-01-26 | 2024-04-11 | Idemitsu Kosan Co.,Ltd. | Composition, powder, organic electroluminescent element, method for manufacturing organic electroluminescent element, and electronic device |
| CN115073501A (en) * | 2021-03-10 | 2022-09-20 | 北京夏禾科技有限公司 | Organic electroluminescent material and device thereof |
| CN115073503A (en) * | 2021-03-12 | 2022-09-20 | Sfc株式会社 | Polycyclic compound and organic electroluminescent device using the same |
| EP4056577A1 (en) * | 2021-03-12 | 2022-09-14 | SFC Co., Ltd. | Polycyclic compound and organic electroluminescent device using the same |
| CN115611937A (en) * | 2021-07-12 | 2023-01-17 | Sfc株式会社 | Polycyclic compound and organic light emitting device using the same |
| CN114835663A (en) * | 2022-06-07 | 2022-08-02 | 阜阳欣奕华材料科技有限公司 | Naphtho heteroaryl compound, organic electroluminescent device and display device |
| CN114890970A (en) * | 2022-06-08 | 2022-08-12 | 阜阳欣奕华材料科技有限公司 | Anthracene compound, organic electroluminescent device and display device |
| CN115160273A (en) * | 2022-08-08 | 2022-10-11 | 上海传勤新材料有限公司 | Compound containing dibenzo heterocycle and preparation method and application thereof |
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