CN111328329B - Novel heterocyclic compound and organic light-emitting device using same - Google Patents
Novel heterocyclic compound and organic light-emitting device using same Download PDFInfo
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- CN111328329B CN111328329B CN201980005102.3A CN201980005102A CN111328329B CN 111328329 B CN111328329 B CN 111328329B CN 201980005102 A CN201980005102 A CN 201980005102A CN 111328329 B CN111328329 B CN 111328329B
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 7
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- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000000113 cyclohexyl group Chemical group [H]C1([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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
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- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 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 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-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
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 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
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- 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
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 239000005416 organic matter Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
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- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002098 pyridazinyl group Chemical group 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing 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
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000004434 sulfur atom Chemical group 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical group [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 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
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/08—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- C07D409/08—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 alicyclic rings
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
Abstract
The present invention provides a novel heterocyclic compound and an organic light-emitting device using the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2018-0123386, 10-16 of 2018, the entire contents of the disclosure of the document of which are incorporated as part of the present specification.
The present invention relates to a novel heterocyclic compound and an organic light-emitting device including the same.
Background
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 device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from an anode to an organic layer, electrons are injected from a cathode to the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons re-transition to a ground state.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
Prior art literature
Patent literature
(patent document 0001) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Problems to be solved
The present invention relates to a novel heterocyclic compound and an organic light-emitting device including the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
q is substituted or unsubstituted C 10-30 An aromatic ring having an aromatic ring structure,
y is O or S, and the total number of the catalyst is O or S,
l is a direct bond, or a substituted or unsubstituted C 6-60 An arylene group,
x is each independently N or C (R 4 ) But at least one of X is N,
Ar 1 and Ar is a group 2 Each independently is hydrogen; deuterium; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
a to c are each independently integers from 0 to 3,
R 1 to R 4 Each independently is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 1-60 Alkoxy, substituted or unsubstituted C 1-60 Thioalkyl, substituted or unsubstituted C 3-60 Cycloalkyl, substituted or unsubstituted C 6-60 Aryl, or tri (C) 1-60 Alkyl) silyl groups, or combine with each other to form a substituted or unsubstituted monocyclic or polycyclic ring.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 can be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, lower driving voltage and/or improvement of lifetime characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
The present invention provides a compound represented by the above chemical formula 1.
In the present description of the invention,
or->
Refers to a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio group [ ]
Alkylthio) is described; arylthio (/ ->
，Arylthio) is described; alkylsulfonyl (+)>
Alkylsulfoxy); arylsulfonyl (+)>
Aryl sulfoxy); a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent comprising N, O and 1 or more substituents in a heterocyclic group comprising 1 or more of S atoms, or a substituent which is bonded to 2 or more substituents in the above-exemplified substituents. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked. />
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but the number of carbon atoms is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-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, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but cycloalkyl having 3 to 60 carbon atoms is preferable. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are 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 the present invention is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,
A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the fluorenyl group is substituted, it may be that
Etc. However, the present invention is not limited thereto.
In the present specification, the heterocyclic group is a group comprising 1 of O, N, P, si and SThe heterocyclic group as the hetero atom is not particularly limited in the number of carbon atoms, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl, (-) -and (II) radicals>
Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->
Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the above-mentioned examples of the aryl group. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, or alkylamino group is the same as the above-mentioned examples of the alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heterocyclic group. In this specification, alkenyl groups in aralkenyl groups are the same as the examples of alkenyl groups described above. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied thereto. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heterocyclic group can be applied thereto. In the present specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied. In this specification, the heterocyclic ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the heterocyclic group can be applied thereto.
In the above chemical formula 1, preferably, Q may be naphthalene, phenanthrene or triphenylene ring.
More preferably, the above chemical formula 1 may be the following chemical formulas 1-1 to 1-4.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
In the above chemical formulas 1-1 to 1-4,
for Y, a to c, R 1 To R 3 、L、X、Ar 1 And Ar is a group 2 The description of (2) is the same as the previous definition.
Preferably, L may be a direct bond, phenylene, biphenyldiyl or naphthalenediyl.
In addition, preferably Ar 1 And Ar is a group 2 Each may independently be any one selected from the following structures.
Preferably, a to c may each be 0.
For example, the above-mentioned compounds may be selected from the following compounds:
on the other hand, the compound represented by the above chemical formula 1 can be produced by the following production method represented by the following reaction formula 1.
[ reaction type 1]
The above reaction formula 1 is a suzuki coupling reaction, preferably each reaction is carried out in the presence of a palladium catalyst and a base, and the reactive groups for the suzuki coupling reaction may be modified according to techniques known in the art. The above-described production method can be more specifically described in the production example described later.
In addition, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
The organic layer may include a hole injection layer, a hole transport layer, or a layer that performs hole injection and transport simultaneously, and the hole injection layer, the hole transport layer, or the layer that performs hole injection and transport simultaneously may include a compound represented by chemical formula 1.
The organic layer may include a light-emitting layer, and the light-emitting layer may include a compound represented by chemical formula 1.
The organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by chemical formula 1.
In addition, the electron transport layer, the electron injection layer, or the layer performing both electron transport and electron injection may contain a compound represented by the above chemical formula 1.
In addition, the organic layer includes a light emitting layer and an electron transporting layer, and the electron transporting layer may include a compound represented by the chemical formula 1.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in one or more of the above hole injection layer, hole transport layer, light emitting layer, and electron injection and transport layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that one or more of the organic layers contains the compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO: al or SnO 2 : a combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: the light-emitting device has a hole transporting capability, a hole injecting effect from an anode, an excellent hole injecting effect for a light-emitting layer or a light-emitting material, prevention of migration of excitons generated in the light-emitting layer to the electron injecting layer or the electron injecting material, and an excellent thin film forming capability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer is preferable, and a substance having a large mobility to the holes is preferable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. As a specific example, there is 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (E
Azole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
) Pyrimidine derivatives, and the like, but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,
DiindenopyreneAnd the like, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and is preferably a substance having high mobility for electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: has an electron transporting ability, an electron injecting effect from a cathode, an excellent electron injecting effect to a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from migrating to a hole injecting layer, and has an excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,/->
Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Example 1 (E1)
1) E1-P1 production
The above chemical formula 1- (2-bromophenyl) naphthalene compound (20 g,70.6 mmol) was added to 200mL of tetrahydrofuran, n-butyllithium (25.4 mL,63.6 mmol) was added dropwise at-78℃and then stirred for about 1 hour. After 2-bromo-9H-xanthen-9-one compound (15.5 g,56.5 mmol) was added thereto, the mixture was stirred at room temperature for 2 hours. After extraction with ethyl acetate, concentration was performed, whereby a compound represented by the above formula E1-P1 was produced (23.0 g, yield 95%).
MS[M+H]+＝479
2) E1-P2 production
The above chemical formula E1-P1 (23 g,50.0 mmol) was added to 200mL of acetic acid, and after adding 1 to 2 drops of sulfuric acid at 80℃the mixture was refluxed for 3 hours. The temperature was lowered to room temperature, and after the reaction was completed, the mixture was filtered to obtain a white solid. The filtered white solid was washed with THF and ethyl acetate, respectively, 2 times, thereby producing a compound represented by the above chemical formula E1-P2 (17.7 g, yield 80%).
MS[M+H] + ＝461
3) E1-P3 production
The compound represented by the above formula E1-P2 (17 g,36.8 mmol) and the compound of the formula E1-P2-A (10.3 g,40.5 mmol) were completely dissolved in two
After alkane (Dioxane) (170 mL), potassium acetate (10.8 g,110.5 mmol) was added and stirred with heating. The temperature is reduced to normal temperature, and after the reaction is finished, the potassium carbonate solution is removed, and the potassium acetate is removed by filtration. The filtrate was solidified with ethanol and filtered. The white solids were washed with ethanol 2 times, respectively, to thereby produce compounds represented by the above chemical formulas E1 to P3 (15.3 g, yield 82%).
MS[M+H] + ＝509
4) E1 production
After completely dissolving the compound represented by the above formula E1-P3 (7 g,13.8 mmol) and the compound represented by the above formula E1-P3-A (3.7 g,13.8 mmol) in THF (100 mL), potassium carbonate (5.7 g,41.3 mmol) was dissolved in 40mL of water and added. After adding tetrakis (triphenylphosphine) palladium (0.48 g,0.413 mmol), the mixture was stirred with heating for 8 hours. The temperature was lowered to room temperature, and after the reaction was completed, the potassium carbonate solution was removed to filter out a white solid. The filtered white solid was washed with THF and ethyl acetate, respectively, 2 times, thereby producing a compound represented by the above chemical formula E1 (5.9 g, yield 70%).
MS[M+H] + ＝614
Example 2 (E2)
Except that each starting material was used as shown in the above reaction formula, the compound represented by the above chemical formula E2 was produced by the same method as the production method of E1 of example 1.
MS[M+H] + ＝766
Example 3 (E3)
The compound represented by the above chemical formula E3 was produced by the same method as the method for producing E1 of example 1, except that each starting material was used as shown in the above reaction formula.
MS[M+H] + ＝790
Example 4 (E4)
The compound represented by the above chemical formula E4 was produced by the same method as the method for producing E1 of example 1, except that each starting material was used as shown in the above reaction formula.
MS[M+H] + ＝613
Example 5 (E5)
Except that each starting material was used as shown in the above reaction formula, a compound represented by the above chemical formula E5 was produced by the same method as the production method of E1 of example 1.
MS[M+H] + ＝689
Example 6 (E6)
The compound represented by the above chemical formula E6 was produced by the same method as the method for producing E1 of example 1, except that each starting material was used as shown in the above reaction formula.
MS[M+H] + ＝690
Example 7 (E7)
Except that each starting material was used as shown in the above reaction formula, the compound represented by the above chemical formula E7 was produced by the same method as the production method of E1 of example 1.
MS[M+H] + ＝740
Example 8 (E8)
Except that each starting material was used as shown in the above reaction formula, a compound represented by the above chemical formula E8 was produced by the same method as the production method of E1 of example 1.
MS[M+H] + ＝642
Example 9 (E9)
Except that each starting material was used as shown in the above reaction formula, a compound represented by the above chemical formula E9 was produced by the same method as the production method of E1 of example 1.
MS[M+H] + ＝706
Example 10 (E10)
Except that each starting material was used as shown in the above reaction formula, the compound represented by the above chemical formula E10 was produced by the same method as the production method of E1 of example 1.
MS[M+H] + ＝706
Example 11 (E11)
Except that each starting material was used as shown in the above reaction formula, the compound represented by the above chemical formula E11 was produced by the same method as the production method of E1 of example 1.
MS[M+H] + ＝757
Example 12 (E12)
The compound represented by the above chemical formula E12 was produced by the same method as the production method of E1 of example 1, except that each starting material was used as shown in the above reaction formula.
MS[M+H] + ＝720
Example 13 (E13)
The compound represented by the above chemical formula E13 was produced by the same method as the production method of E1 of example 1, except that each starting material was used as shown in the above reaction formula.
MS[M+H] + ＝740
Example 14 (E14)
The compound represented by the above chemical formula E14 was produced by the same method as the production method of E1 of example 1, except that each starting material was used as shown in the above reaction formula.
MS[M+H] + ＝729
Experimental example 1
To ITO (indium tin oxide)
The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following HI-A compound was used
And performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, the following HAT compound is vacuum evaporated in sequence>
And HT-A compounds of the following->
And a hole transport layer is formed.
Next, a light-emitting layer was formed by vacuum deposition of the BH compound and BD compound described below at a weight ratio of 25:1 at a film thickness of 20nm on the hole transport layer.
The compound (E1) of example 1 and the following LiQ compound were vacuum-evaporated on the light-emitting layer at a weight ratio of 1:1 to give a light-emitting layer
Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>
Is made of aluminum +.>
And the thickness of the metal layer is evaporated to form a cathode.
In the process, the evaporation rate of the organic matters is maintained to be 0.4 to
Lithium fluoride maintenance of cathode
Is kept at>
Is to maintain a vacuum degree of 1X 10 during vapor deposition -7 Up to 5X 10 -5 The support, thereby manufacturing the organic light emitting device. />
Experimental examples 2 to 14
An organic light-emitting device was manufactured by the same method as in experimental example 1 described above, except that the compounds (E2 to E14) of examples 2 to 14 were used instead of the compound (E1) of example 1.
Comparative examples 1 to 9
An organic light-emitting device was manufactured by the same method as in experimental example 1 described above, except that the following compounds (ET-1-a to ET-1-I) were used instead of the compound (E1) of example 1.
The organic light-emitting devices manufactured in the above experimental examples and comparative examples were subjected to a temperature of 10mA/cm 2 The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm 2 The time required for the initial luminance to be 90% with respect to the initial luminance was measured (T90). The results are shown in Table 1 below.
[ Table 1]
As described in table 1 above, the compound represented by chemical formula 1 according to the present invention can be used for an organic layer of an organic light emitting device that can simultaneously perform electron injection and electron transport.
Comparing experimental examples 1 to 8 and 13 of table 1 above with experimental examples 9 to 11 and 14, it was confirmed that the effects of both cores of xanthene (xanthene) or thioxanthene (thioxanthene) show significantly excellent characteristics in terms of driving voltage, efficiency and lifetime of the organic light emitting device without distinction.
Comparing the experimental examples of table 1 above with comparative examples 1 to 2, it was confirmed that the compound substituted with triazine or pyrimidine in xanthene or thioxanthene as in chemical formula 1 according to the present invention shows significantly superior characteristics in terms of efficiency and lifetime of the organic light emitting device compared to the compound unsubstituted with triazine or pyrimidine in xanthene or thioxanthene.
Comparing the experimental examples of table 1 described above with comparative examples 3,4, 7, 8 and 9, it was confirmed that the compound having an aromatic ring formed on the fluorenyl group of xanthene or thioxanthene as in chemical formula 1 according to the present invention showed significantly superior characteristics in terms of lifetime of the organic light emitting device as compared to the compound having no aromatic ring formed on the fluorenyl group of xanthene or thioxanthene.
Comparing the experimental examples of table 1 above with comparative examples 3,4, 7, 8 and 9, it was confirmed that the compound substituted with the aromatic ring and the triazine or pyrimidine on the different planes from each other on the fluorenyl group of xanthene or thioxanthene as in chemical formula 1 according to the present invention showed significantly superior characteristics in terms of lifetime of the organic light emitting device as compared with the compound substituted with the aromatic ring and the triazine or pyrimidine on the same plane as each other on the fluorenyl group of xanthene or thioxanthene.
[ symbolic description ]
1: substrate 2: anode
3: light emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: electron injection and transport layers.
Claims (5)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
q is naphthalene, phenanthrene or triphenylene ring,
y is O or S, and the total number of the catalyst is O or S,
l is a direct bond, phenylene, biphenyldiyl, or naphthalenediyl,
x is each independently N or C (R 4 ) But at least one of X is N,
Ar 1 and Ar is a group 2 Each independently is any one selected from the following structures:
a to c are each independently integers from 0 to 3,
R 1 to R 4 Each independently is hydrogen, deuterium or C 1-6 An alkyl group.
2. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formulas 1-1 to 1-4:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1-3
Chemical formulas 1-4
In the chemical formulas 1-1 to 1-4,
for Y, a to c, R 1 To R 3 、L、X、Ar 1 And Ar is a group 2 Is the same as defined in claim 1.
3. The compound of claim 1, wherein a to c are each 0.
4. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the following structures:
5. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains the compound according to any one of claims 1 to 4.
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