CN116199656A - Compound containing naphthofuran and anthracene and organic light-emitting device using compound - Google Patents
Compound containing naphthofuran and anthracene and organic light-emitting device using compound Download PDFInfo
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- CN116199656A CN116199656A CN202310222392.5A CN202310222392A CN116199656A CN 116199656 A CN116199656 A CN 116199656A CN 202310222392 A CN202310222392 A CN 202310222392A CN 116199656 A CN116199656 A CN 116199656A
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- Prior art keywords
- naphthofuran
- anthracene
- compound
- light
- organic light
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 150000001875 compounds Chemical class 0.000 title claims abstract description 52
- MFMVRILBADIIJO-UHFFFAOYSA-N benzo[e][1]benzofuran Chemical compound C1=CC=C2C(C=CO3)=C3C=CC2=C1 MFMVRILBADIIJO-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 239000000463 material Substances 0.000 claims abstract description 21
- 239000010410 layer Substances 0.000 claims description 30
- 239000012044 organic layer Substances 0.000 claims description 14
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 12
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 7
- -1 benzophenanthryl Chemical group 0.000 claims description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004431 deuterium atom Chemical group 0.000 claims description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000001816 cooling Methods 0.000 description 18
- 239000012065 filter cake Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 238000000967 suction filtration Methods 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 14
- 239000002994 raw material Substances 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000004537 pulping Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000012544 monitoring process Methods 0.000 description 6
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- KJRJBBVVHYGROV-UHFFFAOYSA-N ClP(C1=CC=C(C=C1)N(C)C)(C(C)(C)C)(C(C)(C)C)Cl Chemical compound ClP(C1=CC=C(C=C1)N(C)C)(C(C)(C)C)(C(C)(C)C)Cl KJRJBBVVHYGROV-UHFFFAOYSA-N 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006757 chemical reactions by type Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940127271 compound 49 Drugs 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- ZXVFTTRBWPOSLL-UHFFFAOYSA-N thieno[3,2-b][1]benzofuran Chemical compound O1C2=CC=CC=C2C2=C1C=CS2 ZXVFTTRBWPOSLL-UHFFFAOYSA-N 0.000 description 2
- ASQXKNXJNDLXQV-UHFFFAOYSA-N (10-naphthalen-1-ylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 ASQXKNXJNDLXQV-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 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
- PQVIOPAWVAOHOA-UHFFFAOYSA-N 3-bromonaphthalen-2-ol Chemical compound C1=CC=C2C=C(Br)C(O)=CC2=C1 PQVIOPAWVAOHOA-UHFFFAOYSA-N 0.000 description 1
- CHFHJZQNRFZRNY-UHFFFAOYSA-N 4-[tert-butyl-(1,1-dichloro-2-methylpropan-2-yl)phosphanyl]-N,N-dimethylaniline Chemical compound ClC(C(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C)Cl CHFHJZQNRFZRNY-UHFFFAOYSA-N 0.000 description 1
- IQTHEAQKKVAXGV-UHFFFAOYSA-N 4-ditert-butylphosphanyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1 IQTHEAQKKVAXGV-UHFFFAOYSA-N 0.000 description 1
- RSQXKVWKJVUZDG-UHFFFAOYSA-N 9-bromophenanthrene Chemical compound C1=CC=C2C(Br)=CC3=CC=CC=C3C2=C1 RSQXKVWKJVUZDG-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 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
- 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000013078 crystal Substances 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
- 238000004090 dissolution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 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
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
-
- 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
- C09K2211/1007—Non-condensed systems
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- 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
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- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A compound containing naphthofuran and anthracene and an organic light-emitting device using the compound belong to the field of OLED materials. The compound has the structures shown in formulas (I) - (III), has good thermal stability, film forming stability and excellent light emission performance, can be used for preparing OLED light-emitting devices, especially can be used as a blue light main material of a light-emitting layer in the OLED devices, and can effectively improve the light-emitting efficiency and service life of the organic light-emitting devices.
Description
Technical Field
The present invention relates to a naphthofuran and anthracene-containing compound that can be used in an organic light-emitting element and an organic light-emitting device using the same, and more particularly, to a naphthofuran and anthracene-containing compound that can be used in a light-emitting layer in an organic light-emitting element and thus realize element characteristics such as high light-emitting efficiency, long life, and low voltage driving, an organic light-emitting device using the same, and an organic light-emitting element including the same.
Background
The organic light emitting element (organic light emitting diode; OLED) is a display device utilizing a self-luminescence phenomenon, has a large viewing angle, is thinner and thinner than a liquid crystal display device, has a faster response speed, and can realize flexible display, and therefore is expected to be applied as a full-color display device or an illumination device.
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting element utilizing an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic layer interposed between the anode and the cathode.
In many cases, the organic layer is composed of a multilayer structure of different materials, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like, in order to improve efficiency and stability of the organic light emitting element. If a voltage is applied between two electrodes in the structure of such an organic light emitting element, holes in the anode will be injected into the organic layer, and electrons in the cathode will also be injected into the organic layer, forming excitons (exiton) when the injected holes and electrons meet at the light emitting layer, which will emit photons when the excitons release energy to transition to the ground state, thereby generating light. Such an organic light-emitting element is widely known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, high-speed responsiveness, and the like.
At present, research on organic electroluminescent materials has been widely conducted in academia and industry, wherein a blue light host material is an important component of an organic electroluminescent device, and there is still a great room for improvement on stability and luminescence properties of the blue light host material, which restricts industrialization of the luminescent device. Therefore, the design and search of a compound as a novel material of the OLED to overcome the defects of the compound in the practical application process are important points in the research work of the OLED material and the research trend in the future.
Disclosure of Invention
The invention aims to provide a compound containing naphthofuran and anthracene and an organic light-emitting device using the compound, wherein the compound has good thermal stability, and the light-emitting device prepared by using the compound has higher light-emitting efficiency and service life.
The invention provides a compound containing naphthofuran and anthracene, which has a structural general formula shown as formula (I) or (ll) or (III)
Wherein R is 1 、R 2 Independently selected from substituted or unsubstituted C 6 ～C 30 Aromatic hydrocarbon group or C 6 ～C 30 Aromatic heterocyclic groups of (a).
Preferably, the aromatic hydrocarbon group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, indenyl, fluorenyl, perylenyl, phenanthryl, pyrenyl, fluoranthenyl, or benzophenanthryl.
Preferably, the heteroatom in the aromatic heterocyclic group is oxygen or sulfur.
Preferably, the aromatic heterocyclic group is selected from benzofuran, benzothiophene, dibenzofuran or dibenzothiophene, benzofuranothiophene and the like, more preferably dibenzofuran or dibenzothiophene.
Preferably, the compound containing naphthofuran and anthracene is shown in any one of formulas 1 to 90, and hydrogen atoms in the following formulas 1 to 90 may be replaced by deuterium atoms, which is also in the scope of the present invention:
the invention also provides an organic light-emitting device comprising the naphthofuran and anthracene containing compound.
Preferably, the organic light emitting device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode; the organic layer comprises the compound containing naphthofuran and anthracene.
Preferably, the organic layer is a light emitting layer, and the compound containing naphthofuran and anthracene is used as a blue light host material of the light emitting layer.
The invention has the beneficial effects that:
compared with the prior art, the compound containing the naphthofuran and the anthracene and the organic light-emitting device using the compound are provided, the compound containing the naphthofuran and the anthracene has the structures shown in formulas (I) to (III), and the compound containing the naphthofuran and the anthracene has good thermal stability and excellent light-emitting performance, can be used for preparing organic light-emitting devices, particularly can be used as a blue light main material in the organic light-emitting devices, and can effectively improve the light-emitting efficiency and the service life of the organic light-emitting devices.
Detailed Description
For a further understanding of the present invention, preferred embodiments of the invention are described below in conjunction with the examples, but it should be understood that these descriptions are merely intended to illustrate further features and advantages of the invention, and are not limiting of the claims of the invention.
Unless otherwise defined, technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art.
The aromatic hydrocarbon group in the present invention refers to a generic term that a monovalent group remains after one hydrogen atom is removed from the aromatic nucleus carbon of an aromatic hydrocarbon molecule, and may be a monocyclic aryl group or a condensed ring aryl group, for example, but not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthryl, indenyl, fluorenyl, perylenyl, phenanthryl, pyrenyl, fluoranthryl, or benzophenanthryl.
The aromatic heterocyclic group refers to a generic term for groups obtained by substituting one or more aromatic nucleus carbon in an aryl group with a heteroatom, wherein the heteroatom includes but is not limited to oxygen and sulfur, and the heteroaryl group can be a monocyclic heteroaryl group or a condensed ring heteroaryl group, and can be selected from benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzofuranothiophene and the like, but is not limited thereto.
The invention firstly provides a compound containing naphthofuran and anthracene, which has a structural general formula shown in formulas (I) to (III):
wherein R is 1 、R 2 Independently selected from a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group.
According to the invention, said R 1 、R 2 Independently selected from substituted or unsubstitutedSubstituted C 6 ～C 30 Aromatic hydrocarbon groups of (C), or substituted or unsubstituted C 6 ～C 30 Aromatic heterocyclic groups of (a). More specifically, it is preferably selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, indenyl, fluorenyl, perylenyl, phenanthryl, pyrenyl, fluoranthenyl or benzophenanthryl. The heteroatom in the aromatic heterocyclic group is oxygen or sulfur, preferably dibenzofuran or dibenzothiophene.
According to the present invention, the naphthofuran and anthracene-containing compound is preferably represented by any one of formulas 1 to 90, and the hydrogen atom in the following formulas 1 to 90 may be replaced with a deuterium atom, and is also within the scope of the present invention:
the specific structural forms of the naphthofuran-and anthracene-containing compound of the present invention are exemplified above, but the naphthofuran-and anthracene-containing compound of the present invention is not limited to the chemical structures listed, and R is based on the structures represented by the formulae (I) to (III) 1 、R 2 Groups as defined above should be included.
The invention relates to a preparation method of a compound containing naphthofuran and anthracene, wherein one reaction route is shown in the following general formula.
The conditions of the above reactions are not particularly critical in the present invention, as such reactions are well known to those skilled in the artAnd (5) conventional conditions are adopted. The source of the raw materials used in the above reaction is not particularly limited in the present invention, and the raw materials or intermediates may be commercially available products or prepared by a preparation method well known to those skilled in the art. Wherein the R is 1 、R 2 The selection of (a) is the same as described above and will not be described in detail here.
For the naphthofuran and anthracene-containing compound provided by the invention, the synthesis method can be other reaction types well known to those skilled in the art, and the reaction general formula is only one of the possible reaction types.
The present invention also provides an organic light-emitting device including the naphthofuran and anthracene-containing compound. The organic light emitting device may be an organic light emitting device well known to those skilled in the art, and the organic light emitting device of the present invention preferably includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode; the organic layer comprises the compound containing naphthofuran and anthracene. The organic layer may include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and preferably the compound containing naphthofuran and anthracene is used as a blue light host material in the organic layer.
The source of the raw materials used in the following examples is not particularly limited and may be a commercially available product or may be prepared by a preparation method well known to those skilled in the art.
Example 1: synthesis of intermediate I-a
To the reaction flask were added 20g (0.09 mol) of 3-bromo-2-naphthol, 28.1g of triethylamine (0.278 mol) and 500mL of methylene chloride, 10.4g of acetic anhydride (0.102 mol) was added dropwise at 0℃and stirred at 25℃for 16 hours after the addition was completed, then 100mL of a 10% by mass aqueous hydrochloric acid solution was added to quench the reaction, the organic phase was separated, washed with water to neutrality, and the organic phase was dried over 100g of anhydrous magnesium sulfate and concentrated to give 21.3g of a yellow solid with a purity of 99.5% and a yield of 90%.
I-a-A2
Into a reaction flask was charged 26g l-a-A1 (0.1 mol), 300ml triethylamine and 300ml DMF, and 11.8g trimethylsilylaletylene (0.12 mol), 2.21g (0.003 mol) Pd (Ph) 3 P) 2 Cl 2 1.14g (0.006 mol) of Cul are stirred at 25℃for 16h, then 100ml of 10% strength by mass aqueous hydrochloric acid are added to quench the reaction, then 500ml of 3% strength by mass aqueous dichloromethane are added to extract the product, the dichloromethane phases are combined, washed 4 times with 200ml of 4% strength by mass aqueous water, dried over 100g of anhydrous magnesium sulfate and passed through a chromatographic column packed with 100g of silica gel (200-300 mesh), and the resulting column filtrate is concentrated to give 25.4g of pale yellow solid with a purity of 99.2% and a yield of 90%.
I-a-A3
25.4g (0.09 mol) of I-a-A2, 130g of cesium carbonate (0.4 mol), 800ml of DMF and 100ml of water are added into a reaction flask, the mixture is reacted at 80 ℃ for 5 hours under heat preservation, then the temperature is reduced to room temperature, the reaction solution is poured into 2L of saturated ammonium chloride aqueous solution, the product is separated out, the obtained solid is directly filtered by suction, the obtained solid is washed three times with 50ml of water, the obtained solid is dissolved by 200ml of dichloromethane, and then is subjected to a chromatographic column filled with 50g of silica gel (200-300 meshes), and the column passing solution is concentrated to obtain 11.8g of pale yellow crystal I-a-A3, the purity is 98.5%, and the yield is 78%.
I-a
3.36g (0.02 mol) of l-a-A3 is taken and dissolved in 50ml of tetrahydrofuran, the temperature is reduced to-80 ℃ under the protection of nitrogen, 10ml of 2.5M butyl lithium (0.025 mol) is added dropwise, after the dropwise addition is finished, the system temperature is kept between-80 ℃ and-75 ℃ for reaction for 2 hours, 3.12g (0.03 mol) of trimethyl borate is added dropwise, the temperature is slowly increased to room temperature after the dropwise addition is finished, and the sample is taken and sent for inspection. After the reaction of the raw materials is completed, 100ml of 1M diluted hydrochloric acid is added dropwise, and the mixture is stirred for 30min at normal temperature. Separating, extracting the water phase with 50ml of ethyl acetate 3 times, mixing the organic phases, concentrating to dryness, adding 10ml of n-heptane into the obtained viscous substance, cooling to 0deg.C, and maintaining for 1 hr to obtain the final product. Suction filtration gave 2g of solid with a purity of 99.4% and a yield of 50%. The total yield of the four-step reaction was 31.6%.
Mass spectrum m/z:212.02 (calculated: 212.06). Theoretical element content (%) C 12 H9 B O 3 : c,67.98; h,4.28; b,5.10; o,22.64. Measured element content (%): c,67.96; h,4.30; b,5.09.
The following intermediate compounds were obtained in a similar manner:
TABLE 1
Example 2: synthesis of intermediate 1-A2
Synthesis of intermediate 1-A1
21.2g (0.1 mol) of L-a and 15.7g (0.1 mol) of bromobenzene, 20.7g (0.15 mol) of potassium carbonate and 0.021g of Pd-132 (di-tert-butyl (4-dimethylaminophenyl) phosphine palladium (II)) are added into A1L reaction flask, 200ml of toluene, 100ml of ethanol and 100ml of water are added, the reaction is carried out for 12h at 80 ℃ under nitrogen temperature, TLC monitoring is carried out, the raw materials are separated, water is washed with 100ml of toluene for two times, an organic phase is combined, the organic phase is washed with 300ml of toluene for 2 times, the organic phase is dried and then passes through a chromatographic column filled with 50g of silica gel (200-300 meshes), the column passing solution is concentrated to dryness, 100ml of ethanol and 20ml of toluene are added to 80 ℃ for dissolution, then 20ml of water is slowly added dropwise, the solution is cooled to room temperature, suction filtration is carried out, and the solid 1-A1 is obtained, 17.8g, the purity is 99.7%, and the purity is 73%.
Synthesis of intermediate 1-A2
17.8g (0.073 mol) of 1-A1 and 22.5g (0.1 mol) of NIS are added to 200ml of THF, and the mixture is reacted under nitrogen at 60℃for 16 hours; monitoring the gas phase, after the reaction of the raw materials is finished, 100ml of ethanol and 2L of water are used for separating out solids, suction filtration is carried out, 200ml of water is used for refluxing and pulping a filter cake for 1h, cooling to room temperature and suction filtration is carried out, 50ml of ethanol is used for refluxing and pulping for 1h, cooling to room temperature and suction filtration is carried out, the obtained filter cake is sampled and sent for inspection, the main purity is 99.7%, 12.16g is obtained after drying, the yield of the step is 45%, and the total yield is 32.85%.
Compound 1-A2 mass spectrum m/z:370.12 (calculated: 369.99). Management deviceTheoretical element content (%) C 18 H 11 IO: c,58.40; h,3.00; i,34.28; o,4.32. Measured element content (%): c,58.38; h,3.02; l,34.27.
Nuclear magnetic data for compounds 1-A2: 1H-NMR (Bruker, avanccII400MHz Nuclear magnetic resonance spectrometer, CDCl3, switzerland), δ8.62 (d, 1H), δ8.33 (m, 1H), δ8.12-8.04 (m, 3H), δ7.85 (m, 1H), δ7.70 (m, 1H), δ7.57 (m, 3H), δ7.39 (m, 1H).
The following intermediate compounds were obtained in a similar manner:
TABLE 2
Example 3: synthesis of Compound 1
24.3g (0.065 mol) of intermediate 1-A2, 25.5g (0.085 mol) of 1-B,17.6g (0.127 mol) of potassium carbonate, and 0.025g of Pd-132 (di-tert-butyl-dichloro- (4-dimethylaminophenyl) phosphine palladium (II)) were charged into a 1L reaction flask, 300ml of toluene, 150ml of ethanol and 150ml of water were added, and the reaction was carried out at 80℃for 12 hours under nitrogen, and monitored by TLC. After the raw materials react, cooling to room temperature, carrying out suction filtration, refluxing and pulping a filter cake with 300ml of water for 1h, carrying out suction filtration, refluxing and pulping with 50ml of ethanol for 1h, cooling to room temperature, carrying out suction filtration, refluxing and cleaning the obtained filter cake with 2L of toluene, concentrating the obtained chromatographic liquid of a chromatographic column filled with 100g of silica gel (200-300 meshes) until about 200ml remains, cooling to room temperature, carrying out suction filtration, and drying the obtained filter cake to obtain 22.5g, wherein the main purity is 99.92%, and the yield is 70%.
Mass spectrum m/z:496.20 (calculated: 496.18). Theoretical element content (%) C 38 H 24 O: c,91.91; h,4.87; o,3.22. Measured element content (%):c,91.90; h,4.88. The above results confirm that the obtained product was the target product.
Example 4: synthesis of Compound 49
Synthesis of intermediate 49-A1
21.2g (0.1 mol) of II-a and 25.7g (0.1 mol) of 9-bromophenanthrene, 20.7g (0.15 mol) of potassium carbonate, and 0.021g of Pd-132 (dichlorodi-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (II)) were charged into a 1L reaction flask, and 200ml of toluene, 100ml of ethanol and 100ml of water were added, and reacted at 80℃for 12 hours under nitrogen, followed by TLC monitoring. Separating the solution after the reaction of the raw materials, washing with 100ml of toluene for two times, mixing the organic phases, washing with 300ml of toluene for 2 times, drying the organic phases, passing through a chromatographic column filled with 50g of silica gel (200-300 meshes), concentrating the column passing solution, adding 100ml of ethanol and 20ml of toluene, heating to 80 ℃ for dissolving, slowly dripping 20ml of water, cooling to room temperature, suction filtering to obtain solid 49-A1, drying to obtain 19.2g, and the purity is 99.7%, and the yield is 56%.
Synthesis of intermediate 49-A2
19.2g (0.056 mol) of 49-A1 and 16.4g (0.073 mol) of NIS are added to 200ml of THF, and the mixture is reacted under nitrogen at 60℃for 16 hours; monitoring the gas phase, separating out solid by using 100ml of ethanol and 2L of water after the reaction of the raw materials is finished, carrying out suction filtration, refluxing and pulping a filter cake by using 200ml of water for 1h, cooling to room temperature, carrying out suction filtration, refluxing and pulping by using 50ml of ethanol for 1h, cooling to room temperature, carrying out suction filtration, sampling and sending the obtained filter cake to a sample, wherein the main purity is 99.7%, and drying to obtain 11.2g, and the yield of the step is 42.5%.
Synthesis of Compound 49
22.4g (0.0476 mol) of intermediate 49-A2, 24.86g (0.0714 mol) of 9- (1-naphthyl) -10-anthraceneboronic acid, 13.8g (0.1 mol) of potassium carbonate, and 0.022g of Pd-132 (di-tert-butyl-dichloro- (4-dimethylaminophenyl) phosphine palladium (II)) were charged into a 1L reaction flask, 250ml of toluene, 100ml of ethanol and 100ml of water were added, and the reaction was carried out at 80℃for 12 hours under nitrogen, monitored by TLC. After the raw materials react, cooling to room temperature, suction filtering, refluxing and pulping a filter cake with 300ml of water for 1h, suction filtering, refluxing and pulping with 50ml of ethanol for 1h, cooling to room temperature, suction filtering, refluxing and cleaning the obtained filter cake with 2L of toluene, filtering with a chromatographic column filled with 100g of silica gel (200-300 meshes), concentrating the obtained chromatographic liquid to about 200-m L, cooling to room temperature, suction filtering, drying the obtained filter cake to obtain 20.9g, wherein the main purity is 99.89%, and the yield is 68%.
Mass spectrum m/z:646.22 (calculated: 646.23). Theoretical element content (%) C 50 H 30 O: c,92.85; h,4.68; o,2.47. Measured element content (%): c,92.86; h,4.68. The above results confirm that the obtained product was the target product.
Example 5: synthesis of Compound 81
Synthesis of intermediate 81-A1
21.2g (0.1 mol) of III-a and 15.7g (0.1 mol) of bromobenzene, 20.7g (0.15 mol) of potassium carbonate, and 0.021g of Pd-132 (di-tert-butyl-dichloro- (4-dimethylaminophenyl) phosphine palladium (II)) were charged into a 1L reaction flask, and 200ml of toluene, 100ml of ethanol and 100ml of water were added, and reacted at 80℃for 12 hours under nitrogen atmosphere, monitored by TLC. Separating the solution after the reaction of the raw materials, washing with 100ml of toluene for two times, mixing the organic phases, washing with 300ml of toluene for 2 times, drying the organic phases, passing through a chromatographic column filled with 50g of silica gel (200-300 meshes), concentrating the column passing solution, adding 100ml of ethanol and 20ml of toluene, heating to 80 ℃ for dissolving, slowly dripping 20ml of water, cooling to room temperature, suction filtering to obtain solid 81-A1, drying to obtain 18.5g, purity of 99.7%, and yield of 76%.
Synthesis of intermediate 81-A2
18.5g (0.076 mol) of 81-A1 and 22.5g (0.1 mol) of NIS are added to 200ml of THF, and the mixture is reacted under nitrogen at 60℃for 16 hours; monitoring the gas phase, separating out solid by using 100ml of ethanol and 2L of water after the reaction of the raw materials is finished, carrying out suction filtration, refluxing and pulping a filter cake by using 200ml of water for 1h, cooling to room temperature, carrying out suction filtration, refluxing and pulping by using 50ml of ethanol for 1h, cooling to room temperature, carrying out suction filtration, sampling and sending the obtained filter cake to a sample, wherein the main purity is 99.1%, and drying to obtain 12.4g, and the yield of the step is 44%.
Synthesis of Compound 81
24.3g (0.067 mol) of intermediate 81-A2, 38.9g (0.1 mol) of 81-B,20.7g (0.15 mol) of potassium carbonate, and 0.024g of Pd-132 (di-tert-butyl-dichloro- (4-dimethylaminophenyl) phosphine palladium (II)) were charged into a 1L reaction flask, 300ml of toluene, 150ml of ethanol and 150ml of water were added, and the reaction was carried out at 80℃under nitrogen for 12 hours, followed by TLC monitoring. After the raw materials react, cooling to room temperature, suction filtering, refluxing and pulping a filter cake with 300ml of water for 1h, suction filtering, refluxing and pulping with 50ml of ethanol for 1h, cooling to room temperature, suction filtering, refluxing and cleaning the obtained filter cake with 2L of toluene, and then filtering with a chromatographic column filled with 100g of silica gel (200-300 meshes), concentrating the obtained chromatographic liquid until 200ml remains, cooling to room temperature, suction filtering, drying the obtained filter cake to obtain 25.5g, wherein the main purity is 99.86%, and the yield is 65%.
Mass spectrum m/z:586.21 (calculated: 586.19). Theoretical element content (%) C 44 H 26 O 2 : c,90.08; h,4.47; o,5.45. Measured element content (%): c,90.06; h,4.48. The above results confirm that the obtained product was the target product.
Other compounds can be obtained in a similar synthetic manner.
In the present invention, the specific structures of the materials used in the following application examples are as follows:
device example 1
Device example an organic electroluminescent device was provided, using the compound 1 provided in synthetic example 1 of the present invention as a host material for the light-emitting layer; the organic electroluminescent device structure is as follows:
ITO/HT (40 nm)/luminescent layer host: BD-23% (30 nm)/TPBI (30 nm)/LiF (0.Snm)/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.
Placing the material into a vacuum cavity, vacuumizing to 1X 10-5-1X 10-6Pa, and sequentially vacuum evaporating on the cleaned ITO substrate. Wherein, the luminescent layer host material: BD-23% (30 nm) refers to the device where the light-emitting layer host material and BD-2 were mixed at 97:3 to form a luminescent layer with the thickness of 30nm.
Device examples 2 to 10
Device examples 2 to 10 each provided an organic electroluminescent device differing from device example 1 only in the host material of the light-emitting layer (see table 3 below for details), and the other conditions were the same as those of device example 1.
Device examples 11 to 13
Device examples 11 to 13 each provided an organic electroluminescent device differing from device example 1 only in that the host material of the light-emitting layer was different, and BD-3 was used instead of BD-2 (see Table 3 below for details), except that the other conditions were the same as device example 1.
Device comparative examples 1 to 7
Device comparative examples 1 to 7 each provided an organic electroluminescent device differing from device example 1 only in the light-emitting layer main body (see table 3 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 relative values at the luminance of 1000cd/m 2. The performance test results of the organic electroluminescent device are shown in the following table 3:
TABLE 3 Table 3
As is clear from the contents of Table 3, the present invention provides a compound having naphthofuran and anthracene through molecular design. The compound with the naphthofuran and anthracene structure provided by the invention can be used as a main material of a luminescent layer of an OLED luminescent device, so that the OLED luminescent device has lower driving voltage, higher current efficiency and longer service life.
In addition, when the compound with the naphthofuran and anthracene structure is used as a main material of a light-emitting layer of the OLED light-emitting device to be matched with BD-3, the performance is further improved.
The detailed process flow of the present invention is described by the above embodiments, 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 (9)
1. A compound containing naphthofuran and anthracene has the structural general formula shown in formulas (I) - (III)
Wherein R is 1 、R 2 Independently selected from substituted or unsubstituted C 6 ～C 30 Aromatic hydrocarbon group or C 6 ～C 30 Aromatic heterocyclic groups of (a).
2. A compound containing naphthofuran and anthracene according to claim 1, characterized in that said aromatic hydrocarbon group is selected from phenyl, biphenyl, terphenyl, naphthyl, indenyl, fluorenyl, perylenyl, phenanthryl, pyrenyl, fluoranthenyl or benzophenanthryl.
3. A compound containing naphthofuran and anthracene according to claim 1, characterized in that the heteroatom in the aromatic heterocyclic group is oxygen or sulfur.
4. A naphthofuran and anthracene containing compound according to claim 3, characterized in that said aromatic heterocyclic group is selected from one of benzofuran, benzothiophene, dibenzofuran, dibenzothiophene or benzofuranothiene.
5. The compound of claim 4, wherein the aromatic heterocyclic group is selected from one of dibenzofuran and dibenzothiophene.
6. A compound containing naphthofuran and anthracene according to any one of claims 1 to 5, characterized by being represented by any one of formulae 1 to 90:
and the hydrogen atoms in formulas 1 to 90 may be replaced with deuterium atoms.
7. An organic light-emitting device comprising the naphthofuran-and-anthracene-containing compound according to any one of claims 1 to 6.
8. The organic light-emitting device according to claim 7, comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode; the organic layer comprising the naphthofuran-and-anthracene-containing compound according to any one of claims 1 to 6.
9. An organic light-emitting device according to any one of claims 7 to 8, wherein the organic layer is a light-emitting layer, and the compound containing naphthofuran and anthracene is used as a blue host material of the light-emitting layer.
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| WO2024005432A1 (en) * | 2022-06-29 | 2024-01-04 | 주식회사 엘지화학 | Compound and organic light-emitting device comprising same |
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| KR20240003039A (en) * | 2022-06-29 | 2024-01-08 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
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| JP2001196182A (en) * | 2000-01-14 | 2001-07-19 | Toray Ind Inc | Luminous element |
| CN114514225A (en) * | 2019-07-31 | 2022-05-17 | 杜邦电子公司 | Electroactive compounds |
| WO2022240219A1 (en) * | 2021-05-14 | 2022-11-17 | 에스에프씨 주식회사 | Novel organic compound and organic light-emitting device comprising same |
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