CN113968835A - Substituted anthracene compound and organic electroluminescent device comprising same - Google Patents
Substituted anthracene compound and organic electroluminescent device comprising same Download PDFInfo
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- CN113968835A CN113968835A CN202010710838.5A CN202010710838A CN113968835A CN 113968835 A CN113968835 A CN 113968835A CN 202010710838 A CN202010710838 A CN 202010710838A CN 113968835 A CN113968835 A CN 113968835A
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- China
- Prior art keywords
- anthracene compound
- substituted anthracene
- organic electroluminescent
- electroluminescent device
- substituted
- Prior art date
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- -1 anthracene compound Chemical class 0.000 title claims abstract description 75
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000002019 doping agent Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 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 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 238000004020 luminiscence type Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229940126657 Compound 17 Drugs 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 101100451713 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) HTL1 gene Proteins 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 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 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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
- H10K85/649—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
-
- 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
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a substituted anthracene compound and an organic electroluminescent device comprising the same, wherein the substituted anthracene compound is a fluorescent blue luminous body and has the characteristics of high external quantum efficiency, narrow half-peak width, deep blue luminescence and the like; the organic electroluminescent device using the substituted anthracene compound of the present invention as a light emitting layer has advantages of low driving voltage, high luminance and current efficiency, and long service life.
Description
Technical Field
The invention relates to the field of organic electroluminescent devices, in particular to a substituted anthracene compound and an organic electroluminescent device comprising the same.
Background
Electroluminescence is a physical phenomenon in which a luminescent material directly converts electric energy into light energy under the action of an electric field. Although the research and application of inorganic electroluminescent materials (LEDs) have been developed for some time, there are still many unsolved problems of inorganic electroluminescent materials to date, such as: the material has the advantages of few types, small adjustability, incapability of actively emitting light, low energy efficiency, slow response, harsh use conditions, difficulty in obtaining blue light and the like. In contrast, Organic Light-Emitting Materials (Organic Light-Emitting Materials) are considered to be the most advanced Materials currently used as display screens, and may replace liquid crystal Materials in the near future. Because the Organic Light-Emitting Diode (OLED) has the advantages of an ultra-wide viewing angle, a self-Light-Emitting device does not need to be added with a backlight source, high brightness, high luminance, low power consumption, all-solid-state components, good shock resistance, ultra-thinness, full colorization and the like.
The development of OLED devices has gone through several stages, with the initial use of fluorescent emitters with external quantum efficiencies of only 25%. Heavy metal atoms are introduced into organic molecules later, the addition of the metal atoms promotes phosphorescence emission, the external quantum efficiency can reach 100%, and the method can improve the performance of green and red phosphorescence devices to a great extent. However, the efficiency of blue fluorescent OLED devices has yet to be improved. It follows that the choice of fluorescent blue emitter is particularly important.
It is to be noted that the information disclosed in the above background section is only for enhancement of understanding of the background of the present invention and therefore may include information that does not constitute prior art known to a person of ordinary skill in the art.
Disclosure of Invention
The invention aims to provide a substituted anthracene compound and an organic electroluminescent device comprising the same, wherein the substituted anthracene compound is a fluorescent blue light-emitting body and has the characteristics of high external quantum efficiency, narrow half-peak width, deep blue light emission and the like.
Embodiments of the present invention provide a substituted anthracene compound, a compound having a structure represented by formula I:
wherein,
x is O or S;
Ar1-Ar2each independently selected from structural formula C1To C5Any one of (a);
Ar3-Ar4each independently selected from hydrogen or structural formula C1To C5Any one of (a);
structural formula C1To C5The following were used:
R1-R5each independently is hydrogen, deuterium, cyano, alkyl, cycloalkyl, alkoxy, aryloxy, alkenyl, silyl, amino, aryl or heteroaryl.
According to an example of the present invention, Ar is1-Ar4Each independently selected from structural formula C1To C5Any one of the above.
According to an example of the present invention, R1-R5Each independently is hydrogen, cyano, C1-C30 alkyl, C3-C8 cycloalkyl or C1-C10 alkoxy.
According to an example of the present invention, R1-R5Each independently is hydrogen, cyano, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy or ethoxy.
According to an embodiment of the present invention, the substituted anthracene compound is selected from any one of the following compounds:
further embodiments of the present invention also provide use of the substituted anthracene compound described above in an organic electroluminescent device.
Still further embodiments of the present invention also provide an organic electroluminescent device comprising an anode, a cathode, and one or more organic thin film layers located between the anode and the cathode, wherein at least one of the organic thin film layers comprises the substituted anthracene compound described above.
According to an example of the present invention, at least one of the organic thin film layers is a light-emitting layer, and the light-emitting layer contains the substituted anthracene compound described above.
According to an example of the present invention, the substituted anthracene compound described above is present in the light-emitting layer as a dopant material, a co-dopant material, or a host material.
The substituted anthracene compound provided by the invention is a fluorescent blue light-emitting body, and has the characteristics of high external quantum efficiency, narrow half-peak width, deep blue light emission and the like; the organic electroluminescent device using the substituted anthracene compound of the present invention as a light emitting layer has advantages of low driving voltage, high luminance and current efficiency, and long service life.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying examples. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art.
The "substitution" in the present application means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as the position is a position at which the hydrogen atom is substituted (i.e., a position at which the substituent may be substituted), and when two or more substitutions are made, the two or more substituents may be the same as or different from each other.
Embodiments of the present invention provide a substituted anthracene compound, a compound having a structure represented by formula I:
wherein,
x is O or S;
Ar1-Ar2each independently selected from structural formula C1To C5Any one of (a);
Ar3-Ar4each independently selected from hydrogen or structural formula C1To C5Any one of (a); in one embodiment, the Ar is1-Ar4Each independently selected from structural formula C1To C5Any one of the above.
Structural formula C1To C5The following were used:
R1-R5each independently is hydrogen, deuterium, cyano, alkyl, cycloalkyl, alkoxy, aryloxy, alkenyl, silyl, amino, aryl or heteroaryl.
The alkyl, cycloalkyl, alkoxy, aryloxy, alkenyl, silyl, amine, aryl, or heteroaryl groups can each be substituted or unsubstituted, such as substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted amine, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
The above substituted or unsubstituted alkyl group may be linear or branched, and preferably has 1 to 30 carbon atoms. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but are not limited thereto. Further, R1-R5Each independently is methyl.
The above-mentioned substituted or unsubstituted cycloalkyl group is not particularly limited, preferably, has 3 to 8 carbon atoms, and may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but is not limited thereto.
The above substituted or unsubstituted alkoxy group may be linear, branched or cyclic, and preferably, has 1 to 10 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy (isopropoxyxy), isopropyloxy (i-propyloxy), n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but is not limited thereto.
The above substituted or unsubstituted alkenyl group may be straight-chain or branched, preferably, has 2 to 10 carbon atoms, and includes vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, styryl and the like, but is not limited thereto.
The above substituted or unsubstituted aryloxy group is not particularly limited, and preferably, has 6 to 60 carbon atoms.
The above substituted or unsubstituted silyl group may include, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc.
The substituted or unsubstituted amine group may be selected from-NH 2; an alkylamino group; n-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino, heteroarylamino and the like, preferably having 1 to 30 carbon atoms. Specific examples of the amine group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, an N-phenylnaphthylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group; n-phenylnaphthylamino; n-biphenylnaphthylamino; n-naphthyl fluorenylamino; n-phenylphenanthrylamino; n-biphenylphenanthrylamino; n-phenylfluorenylamino; n-phenyl terphenylamino; n-phenanthrylfluorenylamino; n-biphenylfluorenylamine, and the like, but are not limited thereto. The above-mentioned N-alkylarylamino group means an amino group in which N of the amino group is substituted with an alkyl group and an aryl group; N-Arylheteroarylamine refers to an amine group wherein the N of the amine group is substituted with an aryl or heteroaryl group.
The above substituted or unsubstituted aryl group may be monocyclic or polycyclic, preferably, has 6 to 50 carbon atoms, including phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, yl, fluorenyl and the like, but is not limited thereto.
The above substituted or unsubstituted heteroaryl group contains one or more atoms other than carbon, i.e., heteroatoms, which may include one or more atoms selected from O, N, Se and S, etc. The substituted or unsubstituted heteroaryl group may be monocyclic or polycyclic, preferably, having 2 to 50 carbon atoms.
For example, the substituted anthracene compound of the present invention may be selected from any one of the following compounds:
the following specific preparation examples describe the preparation method of the substituted anthracene compound of the present invention.
Preparation example 1: preparation of Compound 1
In the first step, the first step is that,
the second step is that:
the third step:
after obtaining intermediate a by the above procedure, compound 1 was obtained using the following reaction scheme:
preparation example 2: preparation of Compound 2
Firstly, synthesizing an intermediate A in the same way of preparing a compound 1;
then, compound 2 was obtained using the following reaction formula:
preparation example 3: preparation of Compound 3
In the first step, the first step is that,
the second step is that:
the third step:
after obtaining intermediate B by the above procedure, compound 3 was obtained using the following reaction scheme:
the preparation method of the compound 4-8 is the same as that for the compound 1-3, different intermediates are generated by the same method as in the first to third steps in preparation example 1, and the compound 4-8 is obtained by replacing different intermediates, which is not described herein again.
Preparation example 4: preparation of Compound 9
In contrast to compound 1, the following intermediates were produced in the same manner as in the first to third steps in preparation example 1 in the preparation of compound 9:
compound 9 is then obtained using the following reaction scheme:
preparation of compound 17:
the following intermediates were produced in the same manner as in the first to third steps in preparation example 1:
compound 9 is then obtained using the following reaction scheme:
compounds 18 to 22 were obtained by replacing the substituent groups with those used for the preparation of compound 17, similarly to compound 17, and are not described in detail herein.
The above compounds were tested for their performance, and table 1 shows the results of the performance tests for each compound.
Table 1 shows the results of the performance test of each compound
From Table 1, where MS is the molecular weight of the compound, it can be seen that the substituted anthracene compound has a narrow half-peak width (12-15 nm), and a high external quantum efficiency (9.8%).
Still further embodiments of the present invention also provide an organic electroluminescent device including an anode, a cathode, and one or more organic thin film layers between the anode and the cathode, the organic thin film layers including at least one light emitting layer, and a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof. The light-emitting layer contains the substituted anthracene compound described above, and the substituted anthracene compound is present in the light-emitting layer as a dopant material, a co-dopant material, or a host material.
Example 1
Coating thereon with thickness
The glass substrate of Indium Tin Oxide (ITO) thin film of (a) was put in distilled water in which a detergent was dissolved and cleaned using ultrasonic waves, where a product manufactured by Fischer co.
Cleaning the ITO for 30 minutes, and then repeatedly performing ultrasonic cleaning twice for 10 minutes by using distilled water; after the washing with distilled water was completed, ultrasonic washing was performed using isopropyl alcohol, acetone, and methanol solvents, and the resultant was dried and then transferred to a plasma washing machine. Further, the substrate was cleaned by using oxygen plasma for 5 minutes, and then transferred to a vacuum depositor.
Depositing hexa-nitrile Hexaazatriphenylene (HAT) film on the transparent electrode by thermal vacuum deposition method to obtain a thickness of
Forming a Hole Injection Layer (HIL), the hexanitrile hexaazatriphenylene having the following structural formula:
preparing a hole transport layer HTL1 on the HAT film with a thickness of
The hole injection transport layer HTL1 has the following structural formula:
a hole injection transport layer HTL2 was prepared on the hole injection transport layer HTL1 to a thickness of
The hole injection transport layer HTL2 has the following structural formula:
a light-emitting layer was obtained by vacuum deposition of the inventive compound 1 and BD in a weight ratio of 25:1, the light-emitting layer having a thickness of
BD has the following structural formula:
an electron transport layer ETL is vapor-deposited on the light-emitting layer to a thickness of
The ETL has the following structure: formula (II):
depositing an electron injection layer EIL on the electron transport layer ETL to a thickness of
The EIL has the following structure:
sequentially depositing the electron injection layer EIL with the thickness of
And
the lithium fluoride (LiF) film and the aluminum film form a cathode of the organic electroluminescent device.
In the foregoing process, the deposition rate of the organic material is maintained at
Per second to
The deposition rates of lithium fluoride and aluminum are respectively maintained between one second and one second
Per second to
Second, the vacuum degree during deposition is maintained at 2X 10-7Torr to 5X 10-6Torr.
Examples 2 to 8
An organic electroluminescent device was produced in the same manner as in example 1 except that compounds 4, 6, 8, 9, 12, 15, 19 and 21 were used instead of compound 1 in example 1, respectively. The detailed process is not described again.
Comparative example
An organic electroluminescent device was fabricated by the same method as in example 1, except that an existing BH1 material was used instead of compound 1 in example 1.
BH1 has the following structure:
when current was applied to the organic electroluminescent devices of the above examples 1 to 8, and the comparative example, respectively, voltage, current density, luminance, color coordinates, and service life were measured, and the results are shown in table 2. Where T95 refers to the time it takes for the luminance to decrease to 95% (5000 nits) of the initial luminance.
Table 2 shows the results of the performance tests of the organic electroluminescent devices of examples 1 to 8 and comparative example
As can be seen from the performance test results in table 2, the substituted anthracene compound according to the embodiment of the present invention can be used as a light emitting layer material of an organic electroluminescent device.
The driving voltage of the organic electroluminescent device of the invention is between 3.44V and 3.71V, which is lower than that of the comparative device, namely 4.65V; the current efficiency is 5.52Cd/A to 5.88Cd/AHigher than 4.28Cd/A for the comparative example device; the luminance of the organic electroluminescent device was between 1830V and 1930V, which is greater than 1680V of the comparative example device, except for example 8, and further, T95 of the organic electroluminescent device of the present invention was between 465 hours and 495 hours, which is much longer than 290 hours of the comparative example device. The driving voltage means that the current density of the organic electroluminescent device reaches 10mA/cm2The current density of the required voltage and current efficiency reaches 10mA/cm2Efficiency of the time.
Compared with the organic electroluminescent device adopting the BH1 material in the comparative example, the organic electroluminescent device with the substituted anthracene compound as the light-emitting layer has the advantages of lower driving voltage, higher brightness, improved current efficiency, longer service life and the like.
In conclusion, the substituted anthracene compound and the organic electroluminescent device containing the substituted anthracene compound have the characteristics of high external quantum efficiency, narrow half-peak width, deep blue luminescence and the like, and are a fluorescent blue luminous body; the organic electroluminescent device using the substituted anthracene compound of the present invention as a light emitting layer has advantages of low driving voltage, high luminance and current efficiency, and long service life.
The foregoing is a more detailed description of the invention in connection with specific preferred embodiments and it is not intended that the invention be limited to these specific details. It will be evident to those skilled in the art that the present application is not limited to the details of the foregoing illustrative embodiments, and that the present application may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the application 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.
Claims (9)
1. A substituted anthracene compound, characterized by a compound having a structure according to formula I:
wherein,
x is O or S;
Ar1-Ar2each independently selected from structural formula C1To C5Any one of (a);
Ar3-Ar4each independently selected from hydrogen or structural formula C1To C5Any one of (a);
structural formula C1To C5The following were used:
R1-R5each independently is hydrogen, deuterium, cyano, alkyl, cycloalkyl, alkoxy, aryloxy, alkenyl, silyl, amino, aryl or heteroaryl.
2. The substituted anthracene compound according to claim 1, wherein Ar is Ar1-Ar4Each independently selected from structural formula C1To C5Any one of the above.
3. The substituted anthracene compound according to claim 1, wherein R is R1-R5Each independently is hydrogen, cyano, C1-C30 alkyl, C3-C8 cycloalkyl or C1-C10 alkoxy.
4. The substituted anthracene compound according to claim 1, wherein R is R1-R5Each independently is hydrogen, cyano, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy or ethoxy.
5. The substituted anthracene compound according to any one of claims 1 to 4, wherein the substituted anthracene compound is selected from any one of the following compounds:
6. use of the substituted anthracene compound according to any one of claims 1 to 5 in an organic electroluminescent device.
7. An organic electroluminescent device comprising an anode, a cathode, and one or more organic thin film layers disposed between the anode and the cathode, wherein at least one of the organic thin film layers contains the substituted anthracene compound according to any one of claims 1 to 5.
8. The organic electroluminescent device according to claim 7, wherein at least one of the organic thin film layers is a light-emitting layer, and the light-emitting layer contains the substituted anthracene compound according to any one of claims 1 to 5.
9. The organic electroluminescent device according to claim 8, wherein the substituted anthracene compound according to any one of claims 1 to 5 is present in the light-emitting layer as a dopant material, a co-dopant material, or a host material.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1842509A (en) * | 2004-06-09 | 2006-10-04 | 出光兴产株式会社 | Anthracene derivative and organic electroluminescent device using the same |
| CN102448945A (en) * | 2009-05-29 | 2012-05-09 | 出光兴产株式会社 | Anthracene derivative and organic electroluminescent element using the same |
| CN104892432A (en) * | 2015-05-29 | 2015-09-09 | 上海道亦化工科技有限公司 | Organic electroluminescent anthracene compound and organic electroluminescent device |
| CN106206964A (en) * | 2015-05-27 | 2016-12-07 | 三星显示有限公司 | Organic luminescent device |
| CN109671852A (en) * | 2017-10-16 | 2019-04-23 | 三星显示有限公司 | Organic luminescent device and panel display apparatus including it |
| CN111434658A (en) * | 2019-01-15 | 2020-07-21 | 机光科技股份有限公司 | Organic electroluminescent materials and devices |
-
2020
- 2020-07-22 CN CN202010710838.5A patent/CN113968835A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1842509A (en) * | 2004-06-09 | 2006-10-04 | 出光兴产株式会社 | Anthracene derivative and organic electroluminescent device using the same |
| CN102448945A (en) * | 2009-05-29 | 2012-05-09 | 出光兴产株式会社 | Anthracene derivative and organic electroluminescent element using the same |
| CN106206964A (en) * | 2015-05-27 | 2016-12-07 | 三星显示有限公司 | Organic luminescent device |
| CN104892432A (en) * | 2015-05-29 | 2015-09-09 | 上海道亦化工科技有限公司 | Organic electroluminescent anthracene compound and organic electroluminescent device |
| CN109671852A (en) * | 2017-10-16 | 2019-04-23 | 三星显示有限公司 | Organic luminescent device and panel display apparatus including it |
| CN111434658A (en) * | 2019-01-15 | 2020-07-21 | 机光科技股份有限公司 | Organic electroluminescent materials and devices |
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