CN115043801B - Anthracene-naphthalenyl heteroaryl compound, intermediate, organic electroluminescent device and display device - Google Patents
Anthracene-naphthalenyl heteroaryl compound, intermediate, organic electroluminescent device and display device Download PDFInfo
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- CN115043801B CN115043801B CN202210638789.8A CN202210638789A CN115043801B CN 115043801 B CN115043801 B CN 115043801B CN 202210638789 A CN202210638789 A CN 202210638789A CN 115043801 B CN115043801 B CN 115043801B
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- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 239000000463 material Substances 0.000 claims abstract description 21
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims abstract description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- -1 dibenzofuranyl Chemical group 0.000 claims description 19
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- 125000005580 triphenylene group Chemical group 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 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
- 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
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 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
- 239000000543 intermediate Substances 0.000 claims 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000001308 synthesis method Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 125000005577 anthracene group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- RVPCPPWNSMAZKR-UHFFFAOYSA-N (10-phenylanthracen-9-yl)boronic acid Chemical group C12=CC=CC=C2C(B(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 RVPCPPWNSMAZKR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229940001593 sodium carbonate Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 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 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BUADUHVXMFJVLH-UHFFFAOYSA-N 7-chloro-3-imidazol-1-yl-2H-1,2,4-benzotriazin-1-ium 1-oxide Chemical compound N1[N+](=O)C2=CC(Cl)=CC=C2N=C1N1C=CN=C1 BUADUHVXMFJVLH-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007547 defect 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
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005304 joining 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
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
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- 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
-
- 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
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an anthryl naphthoheteroaryl compound, an intermediate, an organic electroluminescent device and a display device. The anthryl naphthoheteroaryl compound has a structure shown in a formula BH-A or a structure shown in a formula BH-B; the intermediate is used for preparing anthryl naphthoheteroaryl compounds. The anthracene-based naphthoheteroaryl compound provided by the invention is used as a main material of a luminescent layer, and the prepared organic electroluminescent 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 an anthryl naphthoheteroaryl compound, an intermediate, an organic electroluminescent device and a display 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 a display has high brightness, high resolution, wide viewing angle and low energy consumption, so that the display becomes a research hot spot. The organic electroluminescence (OLED) display technology can meet the above requirements of people, and has a wide operating temperature, and can realize other advantages such as flexible display, so that it is a new pet for new generation of flat panel display after CRT (cathode ray tube) display, LCD (liquid crystal display) and PDP (plasma display) flat panel display, and the organic electroluminescence display technology is also known as a flat panel display technology with fantasy display characteristics.
In general, an OLED light emitting device is composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. The hole transport layer HTL is responsible for adjusting the injection speed and the injection amount of holes, and the electron transport layer ETL is responsible for adjusting the injection speed and the injection amount of electrons.
At present, organic electroluminescence has become a mainstream display technology, and accordingly, various novel materials have been developed to prepare an organic layer, but with the development of society and technology, people have put higher demands on various performances of organic electroluminescent devices, especially in terms of efficiency, lifetime, voltage, etc. Accordingly, there is a need in the art to develop a greater variety of higher performance materials to meet the higher demands of OLED devices.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide an anthryl naphthoheteroaryl compound, an intermediate, an organic electroluminescent device and a display device. The anthryl naphthoheteroaryl compound provided by the invention can be used as a main material of a luminescent layer of an organic electroluminescent device, so that the organic electroluminescent 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 an anthracenyl-naphthoheteroaryl compound having a structure represented by formula BH-A or a structure represented by formula BH-B:
Wherein Ar 101 and Ar 102 in the anthracenyl-naphthoheteroaryl compound shown in the formula BH-A and the anthracenyl-naphthoheteroaryl compound shown in the formula BH-B are respectively and independently selected from substituted or unsubstituted C6-C40 aryl and substituted or unsubstituted C12-C20 heteroaryl;
In the anthracenyl naphthoheteroaryl compounds shown in the formula BH-A and the anthracenyl naphthoheteroaryl compounds shown in the formula BH-B, X is independently selected from O or S;
each of the substituted substituents in Ar 101 and Ar 102 is independently selected from at least one of-D, C1 to C10 alkyl or C6 to C15 aryl;
The hydrogen atoms in the anthracenyl-naphthoheteroaryl compounds represented by the formula BH-A and the anthracenyl-naphthoheteroaryl compounds represented by the formula BH-B can be substituted independently by at least one of-D, -F, -CN, C1-C5 alkyl, C6-C15 aryl or C12-C20 heteroaryl.
According to the invention, through the design of the molecular structure of the anthryl naphthoheteroaryl compound, the positions of the anthryl and naphthoheteroaryl groups and two substituents (Ar 101 and Ar 102) are further designed, and the prepared anthryl naphthoheteroaryl compound has excellent performance. The anthryl naphthoheteroaryl compound provided by the invention can be used as a main material of a luminescent layer of an organic electroluminescent device, so that the organic electroluminescent device has lower driving voltage, higher current efficiency and longer service life.
The compounds of the invention contain an anthracene group in position 9 or 10 and(X represents the site of attachment to the 9 or 10 position of the anthracenyl group, X is selected from O or S, the same applies hereinafter), the degree of torsion of the molecular structure increases, andOne of the two is connected with an anthracene group, and the other carbon atom is not connected with H, so that the stability of the structure of the molecule is improved (H connected at the position is more active) while the higher fluorescence quantum efficiency of the whole molecule is maintained, and the prepared OLED device has better performance.
In the present invention, ar 101 and Ar 102 in the anthracenyl-naphthoheteroaryl compound represented by the formula BH-A and the anthracenyl-naphthoheteroaryl compound represented by the formula BH-B are each independently selected from a substituted or unsubstituted C6 to C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, C40, etc.) aryl group and a substituted or unsubstituted C12 to C20 (for example, C12, C14, C16, C18, C20, etc.) heteroaryl group.
The substituents substituted in Ar 101 and Ar 102 are each independently selected from at least one of-D, C1 to C10 alkyl groups or C6 to C15 aryl groups (which may be phenyl, naphthyl, biphenyl, etc.).
The hydrogen atoms in the anthracenyl-naphthoheteroaryl compounds represented by the formula BH-A and the anthracenyl-naphthoheteroaryl compounds represented by the formula BH-B may each independently be substituted by at least one of-D, -F, -CN, C1-C5 alkyl (for example, methyl, ethyl, propyl, etc.), C6-C15 aryl (for example, phenyl, naphthyl, biphenyl, etc.), or C12-C20 heteroaryl (for example, dibenzothienyl, dibenzofuranyl, etc.).
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 preferable embodiment of the present invention, the C6-C40 aryl group is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylene, fluoranthryl, hydrogenated benzoanthryl, indenofluorenyl, benzindene fluorenyl, dibenzoindenofluorenyl, naphthofluorenyl, and benzonaphtofluorenyl.
Preferably, the C12-C20 heteroaryl is selected from any one of dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, dinaphthofuranyl or dinaphthothienyl.
As a preferred embodiment of the present invention, each of Ar 101 and Ar 102 is independently selected from any one of phenyl, biphenyl, fluorenyl, naphthyl, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothienyl, naphtobenzofuranyl, naphtobenzothienyl.
Preferably, the hydrogen atoms in the anthracenyl-naphthoheteroaryl compounds represented by the formula BH-A and the anthracenyl-naphthoheteroaryl compounds represented by the formula BH-B can be substituted by at least one of-D, methyl, ethyl, propyl, butyl, phenyl, biphenyl, naphthyl, dibenzofuranyl and dibenzothienyl.
As a preferable technical scheme of the invention, the anthracenyl-naphthoheteroaryl compound is selected from any one of the following compounds, isomers of the following compounds, deuterated compounds of the following compounds or deuterated compounds of the following compounds isomers:
/>
/>
/>
/>
/>
/>
/>
/>
Wherein each X is independently selected from O or S;
The isomer refers to mother nucleus of the compound The dotted line indicates the attachment site, and X is selected from O or S) and is attached to a carbon atom hybridized with a different sp 2 of substituents Ar 101 and Ar 102.
For example, for compoundsIsomers thereof include, but are not limited to: /(I)Also for example, for compound/>Isomers thereof include, but are not limited to: /(I)
If Ar 101 and/or Ar 102 are composed of two or more substituents (aryl and/or heteroaryl), the parent nucleus of the isomer of the above compound may be linked to any sp 2 hybridized carbon atom of Ar 101 and/or Ar 102 to give the corresponding isomer.
For example, for compoundsIts parent nucleus structure is/>Ar 102 is/>Ar 101 is(Ar 101 is composed of two substituents, phenyl and dibenzofuranyl, respectively), the isomers include: a compound formed by linking a parent nucleus with any one of sp 2 hybridized carbon atoms in Ar 102, and a compound formed by linking a parent nucleus with any one of sp 2 hybridized carbon atoms in Ar 101, and wherein Ar 101 comprises not only/>Also included are structures formed by joining any two sp 2 hybridized carbon atoms in phenyl and dibenzofuran. Thus, the compound/>Including but not limited to: /(I)
The deuterated compound refers to a compound obtained by substituting at least one hydrogen atom in the compound or an isomer of the compound with a deuterium atom.
Preferably, the anthracenyl naphthoheteroaryl group compound is selected from any one of the following compounds:
/>
In a second aspect, the present invention provides an intermediate having any one of the structures shown in formulas 1-3:
Wherein X is selected from O or S;
y and Z are each independently selected from any one of-Cl, -Br or-I;
Ar 102 has the same protective range as described above;
the intermediate is used for preparing the anthryl naphthoheteroaryl compound.
Preferably, the intermediate is selected from any one of the following compounds:
In the invention, the preparation method of the intermediate and the anthryl naphthoheteroaryl compound is as follows:
/>
Or alternatively
Wherein X is selected from O or S;
Y and Z are each independently selected from any one of-Cl, -Br or-I; and when Z is selected from I, Y is selected from Br and Cl, and when Z is selected from Br, Y is selected from Cl;
Ar 101 and Ar 102 each independently have the same protective ranges as described above.
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 anthracenyl naphthoheteroaryl compound as described in the first aspect.
Preferably, the organic thin film layer comprises a light emitting layer, the material of which comprises an anthracenyl naphthoheteroaryl group compound as described in the first aspect.
As a preferred technical scheme of the invention, the material of the light-emitting layer further comprises a compound with a structure shown in a formula II and/or a compound with a structure shown in a formula III:
Wherein Ar 21、Ar22 is each independently selected from any one of substituted or unsubstituted C6-C20 (e.g., may be C6, C8, C10, C12, C16, or C20, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., may be C3, C6, C8, C10, C12, C16, or C20, etc.) heteroaryl;
r 21、R22 and R 23 are each independently selected from any one of hydrogen, C1-C12 (e.g., C1, C2, C4, C6, C8, C10, C12, etc.) linear or branched alkyl, C6-C12 (e.g., C6, C8, C10, C12, etc.) cycloalkyl;
The substituents substituted in Ar 21、Ar22 are each independently selected from C1-C5 (e.g., methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, etc.) linear or branched alkyl or C6-C12 (e.g., phenyl, biphenyl, naphthyl, etc.) aryl;
ar 31、Ar32、Ar33 and Ar 34 are each independently selected from any of substituted or unsubstituted C6-C22 (e.g., may be C6, C8, C10, C16, C18, or C22, etc.) aryl, substituted or unsubstituted C12-C40 (e.g., may be C12, C18, C20, C24, C30, C36, or C40, etc.) 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 (e.g., methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, etc.) or C6-C12 (e.g., C6, C8, C10, C12, etc.) aryl.
As a preferred embodiment of the present invention, ar 21、Ar22 is each independently selected from the group consisting of Any one of the following.
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.
Preferably, ar 31、Ar32、Ar33 and Ar 34 are each independently selected from Any one or a combination of at least two of these.
As a preferred technical scheme of the invention, the compound with the structure shown in the formula II is selected from any one of the following compounds:
/>
preferably, the compound having a structure shown in formula III is selected from any one of the following compounds:
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, through the design of the molecular structure of the anthryl naphthoheteroaryl compound, the positions of the anthryl and naphthoheteroaryl groups and two substituents (Ar 101 and Ar 102) are further designed, and the prepared anthryl naphthoheteroaryl compound has excellent performance. The anthryl naphthoheteroaryl compound provided by the invention can be used as a main material of a luminescent layer of an organic electroluminescent device, so that the organic electroluminescent device has lower driving voltage, higher current efficiency and longer service life.
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.
Preparation example 1
The preparation example provides an intermediate MD-1, and the synthesis method is as follows:
(1) SynthesisofintermediateM-A
100MLofDMF(dimethylformamide)andthenacompoundshownasM-0(2.97g)areaddedintoa250mLthree-neckedflask,thetemperatureisraisedto40℃understirring,N-iodosuccinimidesolid(2.5g)isaddedinbatches,themixtureisreactedfor2hoursat40℃,thetemperatureisraisedto80℃for12hours,themixtureiscooledtoroomtemperature,waterandchloroformareaddedforseparating,anorganiclayeriswashedwithwater,thendriedwithmagnesiumsulfate,afterthemagnesiumsulfateisfiltered,concentratedtodryness,andthemixtureisseparatedbysilicagelcolumnchromatography,andpetroleumether,methylenedichloride=20:0.5(volumeratio)iselutedtoobtainthecompoundshownasM-A(1.7g)asaturquoisesolid.
MassspectrometrydetectionwasperformedontheobtainedM-Acompound: the two peaks with the largest mass-to-charge ratio (m/z) were measured to be 421.88, 423.88 and the product molecular formula was determined to be C 16H8 BrIO.
And(3)performingnuclearmagneticresonancedetectionontheobtainedM-A: 1 H-NMR (Bruker, switzerland, avance II 400MHz Nuclear magnetic resonance spectrometer, CDCl 3), δ8.02 (m, 1H), δ7.88 (m, 2H), δ7.59 (m, 1H), δ7.47 (m, 2H), δ7.35 (m, 1H), δ7.27 (m, 1H).
(2) Synthesis of intermediate MD-1
100MLoftoluene,30mLofethanoland15mLofwateraresequentiallyaddedintoa250mLthree-neckedflaskundertheprotectionofnitrogen,thenanintermediateM-A(4.23g),9-phenyl-10-anthraceneboricacid(2.98g),sodiumcarbonate(2.12g,0.02mol)andtetraphenylphosphinepalladium(0.115g,0.0001mol)areadded,thetemperatureisslowlyincreasedto50℃forreactionfor2h,thetemperatureisincreasedto70℃forreactionfor6h,thetemperatureisreducedtoroomtemperature,waterisadded,theorganiclayeriswashedwithwater,thenmagnesiumsulfateisdried,thesolventisremovedunderreducedpressureafterthemagnesiumsulfateisremovedbyfiltration,andtolueneiscrystallizedtoobtainanintermediateMD-1(3.9g).
Mass spectrometry detection was performed on intermediate MD-1: the two peaks with the largest mass-to-charge ratio (m/z) were measured to be 550.08, 548.08 and the product molecular formula was determined to be C 36H21 BrO.
Preparation examples 2 to 13
The preparation examples provided an intermediate, respectively, the synthesis method of which was referred to the synthesis method of intermediate MD-1, except that 9-phenyl-10-anthraceneboronic acid was replaced with other boric acid compounds in the same amount (see Table 1 for details), and the other conditions were the same as those of intermediate MD-1.
TABLE 1
/>
Preparation example 14
The preparation example provides an intermediate MD-1S, and the synthesis method is as follows:
(1) Synthesis of intermediate M-AS
ThesynthesismethodoftheintermediateM-AisdifferentfromthesynthesismethodoftheintermediateM-AonlyinthatthecompoundrepresentedbyM-0isreplacedbyacompoundrepresentedbyM-0Sinanequalamount,andotherconditionsarethesameasthoseofthesynthesismethodoftheintermediateM-A.
Mass spectrometry detection was performed on the obtained M-AS-indicated compound: the two peaks with the largest mass-to-charge ratio (m/z) are 437.86 and 439.86, and the molecular formula of the product is determined as follows: C16H8BrIS.
(2) Synthesis of intermediate MD-1S
ThesynthesismethodofintermediateMD-1isreferredto,andonlythedifferenceisthatthecompoundrepresentedbyM-AisreplacedwiththecompoundrepresentedbyM-ASinthesameamountasthecompoundrepresentedbyM-A,andtheotherconditionsarethesameasthoseofintermediateMD-1.
Mass spectrometric detection of the resulting MD-1S compound: the two peaks with the largest mass-to-charge ratio (m/z) were measured to be 566.05, 564.05 and the product molecular formula was determined to be C 36H21 BrS.
Preparation examples 15 to 16
Preparation examples 15 to 16 each provided an intermediate, the synthesis of which was referred to the synthesis of intermediate MD-1S, except that 9-phenyl-10-anthraceneboronic acid was replaced with other boronic acid compounds in amounts equivalent to those shown in Table 2, under the same conditions as the synthesis of intermediate MD-1S.
TABLE 2
Synthesis example 1
The present synthetic example provides a compound 1, which is synthesized as follows:
100mL of dioxane and 8mL of water are sequentially added into a 250mL three-necked flask under the protection of nitrogen, then an intermediate M-1 (3.73 g), 9-phenyl-10-anthracene boric acid (2.98 g), sodium carbonate (2.12 g,0.02 mol) and tetraphenylphosphine palladium (0.115 g,0.0001 mol) 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, then magnesium sulfate is dried, after the magnesium sulfate is removed by filtration, the solvent is removed under reduced pressure, and toluene is recrystallized to obtain a compound 1 (3.6 g).
Mass spectrometry detection was performed on compound 1: the mass to charge ratio (m/z) was measured to be 546.20.
The nuclear magnetic resonance of the obtained compound 1 was detected: 1 H-NMR (Bruker, switzerland, avance II 400MHz Nuclear magnetic resonance spectrometer ,CDCl3),δ8.91(m,2H),δ8.22(m,4H),δ7.82(m,1H),δ7.67(m,4H),δ7.56～7.51(m,5H),δ7.49～7.39(m,9H),δ7.28(m,1H).)
Synthesis examples 2 to 44
Examples 2 to 44 each provide a compound, the synthesis method of which is referred to the synthesis method of compound 1, except that intermediate M-1 is replaced with other intermediate in the amount of the same substance, and 9-phenyl-10-anthraceneboronic acid is replaced with boric acid compound in the amount of the same substance (see Table 3 for details), and the other conditions are the same as those of the synthesis method of compound 1.
TABLE 3 Table 3
/>
/>
/>
/>
/>
/>
/>
/>
Other compounds not listed in the synthesis methods can be synthesized by referring to the above examples in combination with common general knowledge in the art, and the present invention is not limited to the above examples.
Specific structures of materials used in the following device examples are as follows:
/>
device example 1
The embodiment of the device provides an organic electroluminescent device, wherein the compound 1 provided by the invention is used as a main material of a luminescent layer;
The organic electroluminescent device structure is as follows: ITO/HT (40 nm)/luminescent layer host material: BD-2 3% (30 nm)/TPBI (30 nm)/LiF (0.5 nm)/Al (150 nm).
The preparation method of the organic electroluminescent device comprises the following steps:
The glass substrate coated with the ITO transparent conductive layer (serving as an anode) is subjected to ultrasonic treatment in a cleaning agent, then washed in deionized water, then subjected to ultrasonic degreasing in a mixed solvent of acetone and ethanol, then baked in a clean environment until the water is completely removed, cleaned by ultraviolet light and ozone, and bombarded on the surface by a low-energy cation beam so as to improve the property of the surface and the bonding capability with a hole layer.
And placing the material in a vacuum cavity, vacuumizing to 1X 10 -5～1×10-6 Pa, and sequentially carrying out vacuum evaporation on the cleaned ITO substrate. Wherein, the luminescent layer host material: BD-2 3% (30 nm) refers to the fact that in the device, the host material of the light-emitting layer and BD-2 are co-evaporated in a volume ratio of 97:3 to form the light-emitting layer, and the thickness of the light-emitting layer is 30nm.
Device examples 2 to 20
Device examples 2-20 provided an organic electroluminescent device differing from device example 1 only in the host material of the light-emitting layer (see table 4 below), and the other conditions were the same as device example 1.
Device comparative examples 1 to 4
Device comparative examples 1 to 4 provided an organic electroluminescent device differing from device example 1 only in the host material of the light-emitting layer (see table 4 below for details), and the other conditions were the same as device example 1.
Performance testing
The testing method comprises the following steps: 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 OLED device; the LT90 is the time required for maintaining the current density at the initial luminance of 1000nit and reducing the luminance to 90% of the original luminance, and the test items include luminance, driving voltage and current efficiency of the organic electroluminescent device, and the driving voltage and current efficiency and LT90 data are all relative values at the luminance of 1000cd/m 2.
TABLE 4 Table 4
As is clear from the contents of Table 4, in the present invention, by designing the structure of the anthracenyl naphthoheteroaryl group compound, the compound contains the 9-position or 10-position of the anthracenyl group and(Representing the structure of the linkage to the 9 or 10 position of the anthracenyl group), the torsion of the molecular structure is increased, and/>One of the two positions is connected with an anthracene group, and the other position is not connected with H on a carbon atom, so that the stability of the structure of the molecule is improved while the higher fluorescence quantum efficiency of the whole molecule is maintained, and the prepared OLED device has better performance. The anthracene-based naphthoheteroaryl compound provided by the invention is used as a main material of a luminescent layer, and the prepared organic electroluminescent device has lower driving voltage, higher current efficiency and longer service life.
If it isOne position of the group is connected with 9 or 10 positions of the anthracene group, and the other position is a hydrogen atom (BH 1, BH2 and BH 3), so that the prepared OLED device (device comparative examples 1-3) has poor performance; if/>The performance of the OLED device prepared (device comparative example 4) was also poor if the groups were not attached to the anthracene group (BH 4).
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 (15)
1. The anthryl naphthoheteroaryl compound is characterized by having a structure shown in a formula BH-A or a structure shown in a formula BH-B:
Wherein Ar 101 and Ar 102 are each independently selected from any one of phenyl, biphenyl, fluorenyl, naphthyl, triphenylene, fluoranthenyl, dibenzofuranyl, dibenzothienyl, naphthodibenzofuranyl, and naphthodibenzothienyl;
In the anthracenyl naphthoheteroaryl compounds shown in the formula BH-A and the anthracenyl naphthoheteroaryl compounds shown in the formula BH-B, X is independently selected from O or S;
The hydrogen atoms in the anthracenyl-naphthoheteroaryl compounds represented by the formula BH-A and the anthracenyl-naphthoheteroaryl compounds represented by the formula BH-B can be substituted independently by at least one of-D, -F, -CN, C1-C5 alkyl, C6-C15 aryl or C12-C20 heteroaryl.
2. The anthracenyl naphthoheteroaryl group according to claim 1, wherein the C12-C20 heteroaryl group is selected from any one of dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, dinaphthofuranyl or dinaphthothienyl.
3. The anthracenyl-naphthoheteroaryl-like compound of claim 1, wherein the hydrogen atoms in the anthracenyl-naphthoheteroaryl-like compound of formula BH-a and the anthracenyl-naphthoheteroaryl-like compound of formula BH-B are each independently substituted with at least one of-D, methyl, ethyl, propyl, butyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl.
4. The anthracenyl-naphthoheteroaryl-like compound of claim 1, wherein the anthracenyl-naphthoheteroaryl-like compound is selected from any one of the following compounds, deuterated compounds of the following compounds:
/>
/>
/>
/>
/>
/>
Wherein each X is independently selected from O or S.
5. An intermediate, characterized in that the intermediate has any one of the structures shown in formulas 1-3:
Wherein X is selected from O or S;
Y is selected from any one of-Cl, -Br or-I, Z is-I;
Ar 102 has the same protective scope as claim 1;
The intermediates are used for the preparation of the anthracenyl naphthoheteroaryl-like compounds according to any of claims 1 to 4.
6. An intermediate according to claim 5, wherein the intermediate is selected from any one of the following compounds:
7. 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 comprises the anthracenyl naphthoheteroaryl group compound as claimed in any one of claims 1 to 4.
8. The organic electroluminescent device according to claim 7, wherein the organic thin film layer comprises a light emitting layer, and a material of the light emitting layer comprises the anthracenyl naphthoheteroaryl group compound according to any one of claims 1 to 4.
9. The organic electroluminescent device according to claim 8, wherein the material of the light-emitting layer further comprises a compound having a structure shown in formula II and/or a compound having a structure shown in formula III:
Wherein Ar 21、Ar22 is independently selected from any one of substituted or unsubstituted C6-C20 aryl and substituted or unsubstituted C3-C20 heteroaryl;
R 21、R22 and R 23 are each independently selected from any one of hydrogen, C1-C12 straight or branched alkyl, C6-C12 cycloalkyl;
The substituents substituted in Ar 21、Ar22 are each independently selected from C1-C5 straight or branched alkyl or C6-C12 aryl;
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 mentioned for Ar 31、Ar32、Ar33、Ar34 are each independently selected from C1-C5 straight-chain or branched alkyl or C6-C12 aryl.
10. The organic electroluminescent device of claim 9, wherein each Ar 21、Ar22 is independently selected from the group consisting of Any one of the following.
11. The organic electroluminescent device according to claim 9, wherein 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.
12. The organic electroluminescent device of claim 9, wherein each of Ar 31、Ar32、Ar33 and Ar 34 is independently selected from the group consisting ofAny one or a combination of at least two of these.
13. The organic electroluminescent device according to claim 9, wherein the compound having a structure represented by formula II is selected from any one of the following compounds:
/>
14. The organic electroluminescent device according to claim 9, wherein the compound having a structure represented by formula III is selected from any one of the following compounds:
15. a display device, characterized in that it comprises an organic electroluminescent device as claimed in any one of claims 7-14.
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