CN107108408B - Spiro-ring-type compound and organic light emitting device including the same - Google Patents
Spiro-ring-type compound and organic light emitting device including the same Download PDFInfo
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- CN107108408B CN107108408B CN201680004811.6A CN201680004811A CN107108408B CN 107108408 B CN107108408 B CN 107108408B CN 201680004811 A CN201680004811 A CN 201680004811A CN 107108408 B CN107108408 B CN 107108408B
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- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
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- 150000004056 anthraquinones Chemical class 0.000 description 1
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- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
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- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 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
- 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
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
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- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 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
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- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005240 diheteroarylamino group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
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- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
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- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
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- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 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
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 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
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- YGNUPJXMDOFFDO-UHFFFAOYSA-N n,4-diphenylaniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 YGNUPJXMDOFFDO-UHFFFAOYSA-N 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
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 239000003960 organic solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 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
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 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
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 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
- 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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 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
- 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
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/72—Spiro hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Engineering & Computer Science (AREA)
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- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present specification provides a compound having a spiro ring structure of chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
This application claims priority and benefit from korean patent application No. 10-2015-0149014, filed on 26.10.2015, and korean patent application No. 10-2016-0130731, filed on 10.10.2016, filed on 10.10.731 of the korean intellectual property office, the entire contents of which are incorporated herein by reference.
The present specification relates to a compound having a spiro ring structure and an organic light emitting device including the same.
Background
The organic light emitting phenomenon generally refers to a phenomenon of converting electric energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure in which: which includes an anode, a cathode, and an organic material layer interposed therebetween. Herein, the organic material layer is generally formed as a multi-layered structure formed of different materials to improve efficiency and stability of the organic light emitting device, for example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in such an organic light emitting device structure, holes and electrons are injected from an anode and a cathode, respectively, into an organic material layer, excitons are formed when the injected holes and electrons meet, and light is emitted when the excitons return to a ground state.
There is a continuing need to develop new materials for such organic light emitting devices.
Disclosure of Invention
Technical problem
The present specification describes compounds having a spiro structure and organic light emitting devices comprising the same.
Technical scheme
One embodiment of the present specification provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
Wherein, in chemical formula 1,
r1 to R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamino group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or may be bonded to an adjacent group to form a substituted or unsubstituted ring,
a is an integer of 0 to 10,
b is an integer of 0 to 7,
c is an integer of 0 to 5,
d is an integer of 0 to 4, and
when a, b, c and d are each 2 or more, the structures in parentheses are the same as or different from each other.
Another embodiment of the present specification provides an organic light emitting device including a first electrode; a second electrode disposed opposite the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the compound of chemical formula 1.
Advantageous effects
The compound described in this specification can be used as a material for an organic material layer of an organic light-emitting device. The compound according to at least one embodiment can improve efficiency, a driving voltage, and/or a lifetime characteristic of an organic light emitting device. In particular, the compounds described in the present specification can be used as a material for hole injection, hole transport, hole injection and hole transport, light emission, electron transport, or electron injection. Further, the compound described in the present specification can be preferably used as a material for a light-emitting layer, electron transport, or electron injection. More preferably, when the compound described in the present specification is used as a material for a hole injection, hole transport, and electron blocking layer, characteristics of low voltage, high efficiency, and/or long life are exhibited.
Drawings
Fig. 1 shows an organic light-emitting device formed of a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4).
Fig. 2 shows an organic light-emitting device formed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron transport layer (7), and a cathode (4).
< reference character >
1: substrate
2: anode
3: luminescent layer
4: cathode electrode
5: hole injection layer
6: hole transport layer
7: electron transport layer
Detailed Description
Hereinafter, the present specification will be described in more detail.
One embodiment of the present specification provides a compound represented by chemical formula 1.
Examples of the substituent are described below, but the substituent is not limited thereto.
In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents 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 amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an unsubstituted or alkyl-substituted silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heterocyclic group, or is unsubstituted, or is substituted with a substituent to which two or more substituents among the above-exemplified substituents are attached, or is. For example, "a substituent having two or more substituents attached" may include biphenyl. In other words, biphenyl can be an aryl group, or interpreted as a substituent having two phenyl groups attached.
In the present description, the expression "substituted or unsubstituted" may mean substituted preferably with one or more substituents selected from: deuterium, halogen groups, nitrile groups, alkyl groups, trimethylsilyl groups, aryl groups, and heterocyclic groups, or unsubstituted.
In the present specification, an "adjacent" group may mean a substituent that substitutes for an atom directly connected to an atom substituted by the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or another substituent that substitutes for an atom substituted by the corresponding substituent. For example, two substituents in the phenyl ring that substitute the ortho position and two substituents in the aliphatic ring that substitute the same carbon can be interpreted as groups that are "adjacent" to each other.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, a compound having the following structure may be included, but the carbonyl group is not limited thereto.
In the present specification, in the ester group, the 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, a compound having the following structural formula may be included, but the ester group is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, compounds having the following structures may be included, but the imide group is not limited thereto.
In the present specification, the silyl group may be represented by the formula-SiRR 'R ", and R, R' and R" may each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the silyl group may include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.
In the present specification, a boron group may be represented by the formula-BRR ', and R' may each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the boron group may include a trimethyl boron group, a triethyl boron group, a tert-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but are not limited thereto.
In the present specification, examples of the halogen group may include fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is from 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is from 1 to 10. According to yet another embodiment, the number of carbon atoms of the alkyl group is from 1 to 6. Specific examples of the alkyl group may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and although the number of carbon atoms is not particularly limited, it is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is from 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is from 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is from 2 to 6. Specific examples thereof may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl, styryl and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is from 3 to 20. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is from 3 to 6. Specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.
In the present specification, the alkoxy group is not particularly limited, but preferably has 1 to 40 carbon atoms. According to one embodiment, the number of carbon atoms of the alkoxy group is from 1 to 10. According to another embodiment, the number of carbon atoms of the alkoxy group is from 1 to 6. Specific examples of the alkoxy group may include, but are not limited to, methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, hexyloxy, and the like.
In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group may include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthracylamino group, a 9-methylanthrylamino group, a diphenylamino group, a phenylnaphthylamino group, a xylylamino group, a phenyltolylamino group, a triphenylamino group, and the like.
In the present specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups, substituted or unsubstituted diarylamine groups, or substituted or unsubstituted triarylamine groups. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. Arylamine groups comprising two or more aryl groups can include monocyclic aryl groups, polycyclic aryl groups, or both monocyclic aryl groups and polycyclic aryl groups.
Specific examples of the arylamine group may include a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 3-methylphenylamino group, a 4-methylnaphthylamino group, a 2-methylbiphenylamino group, a 9-methylanthrylamino group, a diphenylamino group, a phenylnaphthylamino group, a ditolylamino group, a phenyltolylamino group, a carbazole, a triphenylamino group, etc., but are not limited thereto.
In the present specification, examples of heteroarylamino groups include a substituted or unsubstituted monoheteroarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted triheteroarylamino group. The heteroaryl group in the heteroarylamino group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. Heteroaryl amine groups containing two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or both a monocyclic heterocyclic group and a polycyclic heterocyclic group.
In the present specification, arylheteroarylamino means an amino group substituted with an aryl group and a heterocyclic group.
In the present specification, examples of the arylphosphino group include a substituted or unsubstituted monoarylphosphino group, a substituted or unsubstituted diarylphosphino group, or a substituted or unsubstituted triarylphosphino group. The aryl group in the arylphosphino group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphino group comprising two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group.
In the present specification, the aryl group is not particularly limited, but is preferablyHas 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is from 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is from 6 to 20. Examples of the monocyclic aryl group may include phenyl, biphenyl, terphenyl, and the like, but are not limited thereto. Examples of the polycyclic aromatic group may include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, perylene, etc,
A fluorenyl group, a triphenylene group, etc., but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and two of the substituents may be bonded to each other to form a spiro ring structure.
When the fluorenyl group is substituted, it may comprise
And the like. However, the structure is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing one or more of N, O, S, Si and Se as a heteroatom, and although the number of carbon atoms thereof is not particularly limited, it is preferably 2 to 60. Examples of the heterocyclic group may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl
Oxazolyl, thiadiazolyl, benzothiazolyl, phenazinyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In this specification, the description provided above for heterocyclyl groups can be applied to heteroaryl groups, with the difference that heteroaryl groups are aromatic groups.
In this specification, the description provided above for aryl groups can be applied to aryl groups in aryloxy, arylthio, arylsulfonyl, arylphosphino, aralkyl, aralkylamino, aralkenyl, alkylaryl, arylamino, and arylheteroarylamino groups.
In the present specification, the description provided above regarding the alkyl group is applicable to the alkyl group in the alkylthio group, the alkylsulfonyl group, the aralkyl group, the aralkylamino group, the alkylaryl group and the alkylamino group.
In this specification, the description provided above for heterocyclic groups is applicable to heteroaryl groups in heteroaryl, heteroarylamino and arylheteroarylamino groups.
In the present specification, the description provided above about alkenyl groups can be applied to alkenyl groups among aralkenyl groups.
In this specification, the description provided above with respect to aryl groups is applicable to arylene groups, with the exception that arylene groups are divalent.
In this specification, the description provided above for heterocyclyl groups may be applied to heteroarylenes, with the difference that the heteroarylene group is divalent.
In the present specification, bonding to adjacent groups to form a ring means bonding to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a condensed ring thereof.
In the present specification, an aliphatic hydrocarbon ring means a ring which is not aromatic and is formed only of carbon and hydrogen atoms.
In the present specification, examples of the aromatic hydrocarbon ring may include, but are not limited to, phenyl, naphthyl, anthryl, and the like.
In the present specification, an aliphatic heterocyclic ring refers to an aliphatic ring containing one or more heteroatoms.
In the present specification, an aromatic heterocycle refers to an aromatic ring comprising one or more heteroatoms.
In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.
According to one embodiment of the present specification, in chemical formula 1, a is 1 to 10, at least one of R1 is represented by- (L) m-a, L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 10, and a is-NAr 1Ar2, a substituted or unsubstituted N-containing heterocyclic group, -P (═ O) R5R6, a substituted or unsubstituted anthracenyl group; or an aryl group substituted with a halogen group or a nitrile group. Herein, Ar1, Ar2, R5 and R6 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamino group, A substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or may be bonded to an adjacent group to form a substituted or unsubstituted ring.
According to one embodiment of the present specification, in chemical formula 1, a is 1 to 10, at least one of R1 is represented by- (L) m-a, L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 10, and a is-NAr 1Ar 2.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 2, and a is-NAr 1Ar 2.
According to one embodiment of the present specification, chemical formula 1 may be represented by the following chemical formula 2.
[ chemical formula 2]
In the chemical formula 2, the first and second organic solvents,
r2 to R4, b, c and d are as defined in chemical formula 1,
r11 has the same meaning as R1 to R4,
l is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
ar1 and Ar2 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamino group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or may be bonded to an adjacent group to form a substituted or unsubstituted ring,
p is an integer of 1 to 10,
f is an integer of 0 to 10,
1≤p+f≤10，
m is an integer of 1 to 10, and
when p, f and m are each 2 or more, the structures in parentheses are the same as or different from each other.
According to one embodiment of the present specification, chemical formula 1 may be represented by the following chemical formula 3 or 4.
[ chemical formula 3]
[ chemical formula 4]
In the chemical formulae 3 and 4,
r2 to R4, b, c and d are as defined in chemical formula 1,
l1 and L2 are the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
ar1 to Ar4 and Y1 and Y2 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamino group, A substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or may be bonded to an adjacent group to form a substituted or unsubstituted ring,
y1 is an integer from 0 to 9,
y2 is an integer from 0 to 8,
m1 and m2 are the same as or different from each other, and are each independently an integer of 1 to 10, and
when y1, y2, m1, and m2 are each 2 or more, the structures in parentheses are the same as or different from each other.
According to one embodiment of the present specification, chemical formula 1 may be represented by any one of the following chemical formulae 5 to 8:
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
[ chemical formula 8]
In the chemical formulae 5 to 8,
r2 to R4, b, c and d are as defined in chemical formula 1,
l1 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
ar1, Ar2 and Y1 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamino group, A substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or may be bonded to an adjacent group to form a substituted or unsubstituted ring,
y1 is an integer from 0 to 9,
m1 is an integer of 1 to 10, and
when y1 and m1 are each 2 or more, the structures in parentheses are the same as or different from each other.
According to one embodiment of the present specification, chemical formula 1 may be represented by any one of the following chemical formulae 9 to 12:
[ chemical formula 9]
[ chemical formula 10]
[ chemical formula 11]
[ chemical formula 12]
In the chemical formulae 9 to 12,
r2 to R4, b, c and d are as defined in chemical formula 1,
l1 and L2 are the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
ar1 to Ar4 and Y2 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamino group, A substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or may be bonded to an adjacent group to form a substituted or unsubstituted ring,
y2 is an integer from 0 to 8,
m1 and m2 are the same as or different from each other, and are each independently an integer of 1 to 10, and
when y2, m1, and m2 are each 2 or more, the structures in parentheses are the same as or different from each other.
According to one embodiment of the present specification, chemical formula 1 may be represented by the following chemical formula 13 or 14.
[ chemical formula 13]
[ chemical formula 14]
In the chemical formulae 13 and 14,
r2 to R4, b, c and d are as defined in chemical formula 1,
r11 has the same meaning as R2 to R4,
l, L11 and L21 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
ar2, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamino group, A substituted or unsubstituted aralkylamino group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or may be bonded to an adjacent group to form a substituted or unsubstituted ring,
p is an integer of 1 to 10,
f is an integer of 0 to 10,
1≤p+f≤10，
m, m11 and m21 are the same as or different from each other, and are each independently an integer of 1 to 10, and
when p, f, m11, and m21 are each 2 or more, the structures in parentheses are the same as or different from each other.
According to one embodiment of the present disclosure, L, L1, L2, L11, and L21 are the same or different from each other and each independently is a direct bond, or a substituted or unsubstituted monocyclic to pentacyclic arylene.
According to one embodiment of the present disclosure, L, L1, L2, L11, and L21 are the same or different from each other, and each is independently a direct bond, or a substituted or unsubstituted monocyclic to tetracyclic arylene group.
According to one embodiment of the present disclosure, L, L1, L2, L11, and L21 are the same or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene.
L, L1, L2, L11 and L21 are the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted divalent naphthyl group, a substituted or unsubstituted divalent anthracenyl group, a substituted or unsubstituted divalent fluorenyl group, a substituted or unsubstituted divalent phenanthrenyl group, a substituted or unsubstituted divalent pyrenyl group, or a substituted or unsubstituted divalent phenanthrenyl group
And (4) a base.
According to one embodiment of the present disclosure, L, L1, L2, L11, and L21 are the same as or different from each other, and are each independently a direct bond, phenylene, divalent biphenyl, divalent terphenyl, divalent tetrabiphenyl, divalent naphthyl, divalent anthracenyl, divalent fluorenyl, divalent phenanthryl, divalent pyrenyl, or divalent pyrenyl
And (4) a base.
According to one embodiment of the present disclosure, L, L1, L2, L11, and L21 are the same or different from each other, and are each independently a substituted or unsubstituted heteroarylene.
According to one embodiment of the present disclosure, L, L1, L2, L11, and L21 are the same or different from each other and each independently is a direct bond, or may be any one selected from the following structures.
In the structural formula, in the formula,
a1 and A2 are the same as or different from each other, and each is independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or may be bonded to each other to form a substituted or unsubstituted ring, and
the structure may be unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heterocyclic group.
According to one embodiment of the present disclosure, L, L1, L2, L11, and L21 are the same or different from each other and each independently is a direct bond, or may be any one selected from the following structures.
In the structural formula, in the formula,
a1 and A2 are the same as or different from each other, and each is independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or may be bonded to each other to form a substituted or unsubstituted ring, and
the structure may be unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heterocyclic group.
According to one embodiment of the present disclosure, L, L1, L2, L11, and L21 are the same or different from each other and each independently is a direct bond, or may be any one selected from the following structures.
In the structural formula, in the formula,
a1 and A2 are the same as or different from each other, and each is independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or may be bonded to each other to form a substituted or unsubstituted ring, and
the structure may be unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heterocyclic group.
According to one embodiment of the present disclosure, L, L1, L2, L11, and L21 are the same as or different from each other, and each is independently a direct bond, a phenylene group, a biphenylene group, or a fluorenylene group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group containing one or more of N, O and S.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted monocyclic to decacyclic aryl group or a substituted or unsubstituted monocyclic to decacyclic heterocyclic group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted monocyclic to nonacyclic aryl group or a substituted or unsubstituted monocyclic to hexacyclic heterocyclic group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted aryl group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted monocyclic to hexacyclic aryl group.
According to one embodiment of the present description, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently an aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a; or a heterocyclic group which is unsubstituted or substituted with one or more substituents 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 amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently an aryl group which is unsubstituted or substituted with a substituent selected from: deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; or a heterocyclic group unsubstituted or substituted with a substituent selected from: deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl
A group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted phenanthrenyl group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently phenyl unsubstituted or substituted with a substituent selected from: deuterium, halogen radicals, nitrile radicals, substituted orUnsubstituted alkyl, substituted or unsubstituted silyl, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic group; biphenyl unsubstituted or substituted with a substituent selected from: deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; naphthyl unsubstituted or substituted with a substituent selected from: deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; an anthracenyl group unsubstituted or substituted with a substituent selected from: deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; unsubstituted or substituted by a substituent selected from
Base: deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; pyrenyl unsubstituted or substituted with a substituent selected from: deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a terphenyl group unsubstituted or substituted with a substituent selected from the group consisting of: deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group;a tetrakisphenyl group unsubstituted or substituted with a substituent selected from: deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a phenanthryl group which is unsubstituted or substituted with a substituent selected from: deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a triphenylene group unsubstituted or substituted with a substituent selected from: deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; or fluorenyl unsubstituted or substituted with a substituent selected from: deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other, and each is independently a substituted or unsubstituted heterocyclic group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted heterocyclic group comprising one or more of N, O and S.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted monocyclic to hexacyclic heterocyclic group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted monocyclic to pentacyclic heterocyclic group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted bicyclic to hexacyclic heterocyclic group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted tricyclic to hexacyclic heterocyclic group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted thienyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted thiazolyl group
Azolyl, substituted or unsubstituted
Oxadiazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted bipyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted acridinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted phthalazinyl, substituted or unsubstituted pyridopyrimidinyl, substituted or unsubstituted pyridopyrazinyl, substituted or unsubstituted pyrazinopyrazinyl, substituted or unsubstituted pyridylIsoquinolinyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzo
An azole group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted isoquinoid group
An oxazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted phenothiazinyl group, or a substituted or unsubstituted dibenzofuranyl group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl
An oxazolyl, thiadiazolyl, phenothiazinyl or dibenzofuranyl group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted pyridyl group; substituted or unsubstituted pyrimidinyl; substituted or unsubstituted triazinyl; substituted or unsubstituted carbazolyl; substituted or unsubstituted indolocarbazolyl; substituted or unsubstituted benzocarbazolyl; substituted or unsubstituted thienyl; substituted or unsubstituted furyl; substituted or unsubstituted dibenzothienyl; a substituted or unsubstituted dibenzofuranyl group; substituted or unsubstituted quinolyl; substituted or unsubstituted quinoxalinyl; a substituted or unsubstituted quinazolinyl; a substituted or unsubstituted phosphine oxide group; substituted or unsubstituted silyl; a substituted or unsubstituted bicyclic heterocyclic group comprising one or more of N, S and O; a substituted or unsubstituted tricyclic heterocyclyl containing two or more of N, O and S; a substituted or unsubstituted tetracyclic heterocyclyl comprising one or more of S and O; or a substituted or unsubstituted pentacyclic or hexacyclic heterocyclic group comprising one or more N.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a pyridyl group; a pyrimidinyl group; a triazine group; a carbazolyl group; indolocarbazolyl; a benzocarbazolyl group; a thienyl group; a furyl group; a dibenzothienyl group; a dibenzofuranyl group; a quinolyl group; a quinoxalinyl group; a quinazolinyl group; a phosphine oxide group; a silyl group; a bicyclic heterocyclic group comprising one or more of N, S and O; a tricyclic heterocyclic group containing two or more of N, O and S; a tetracyclic heterocyclyl comprising one or more of S and O; or a five or six ring heterocyclic group containing one or more N.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently an aryl group that is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, alkyl groups, trimethylsilyl groups, aryl groups, and heterocyclic groups; or a heterocyclic group which is unsubstituted or substituted with one or more substituents selected from: deuterium, halogen groups, nitrile groups, alkyl groups, trimethylsilyl groups, aryl groups, and heterocyclic groups.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently phenyl unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, alkyl and alkyl-substituted silyl groups, naphthyl groups, biphenyl groups, terphenyl groups, quaterphenyl groups, unsubstituted or alkyl-or aryl-substituted fluorenyl groups, phenanthryl groups, triphenylene groups, dibenzofuranyl groups, dibenzothiophenyl groups, unsubstituted or aryl-substituted carbazolyl groups, or unsubstituted or aryl-substituted benzocarbazolyl groups.
According to one embodiment of the present description, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted 1-naphthyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 2-phenanthrenyl group, a substituted or unsubstituted 3-phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, or a substituted or unsubstituted 9-phenanthrenyl group.
According to one embodiment of the present description, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently a substituted or unsubstituted 2-dibenzothienyl group, a substituted or unsubstituted 2-dibenzofuranyl group, a substituted or unsubstituted 4-dibenzofuranyl group, a substituted or unsubstituted N-carbazolyl group, a substituted or unsubstituted 1-carbazolyl group, a substituted or unsubstituted 2-carbazolyl group, a substituted or unsubstituted 3-carbazolyl group, a substituted or unsubstituted a-benzocarbazolyl group, or a substituted or unsubstituted c-benzocarbazolyl group.
According to one embodiment of the present specification, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a 1-naphthyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 2-phenanthryl group, a triphenylene group, a 3-phenanthryl group or a 9-phenanthryl group.
According to one embodiment of the present description, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently 2-dibenzothienyl, 2-dibenzofuryl, 4-dibenzofuryl, N-carbazolyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, a-benzocarbazolyl or c-benzocarbazolyl.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently an aryl group that is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, alkyl groups, trimethylsilyl groups, aryl groups, and heterocyclic groups; or a heterocyclic group which is unsubstituted or substituted with one or more substituents selected from: deuterium, halogen groups, nitrile groups, alkyl groups, trimethylsilyl groups, aryl groups, and heterocyclic groups.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other and are each independently phenyl unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen groups, nitrile groups, alkyl and alkyl-substituted silyl groups, naphthyl groups, biphenyl groups, terphenyl groups, quaterphenyl groups, unsubstituted or alkyl-or aryl-substituted fluorenyl groups, phenanthryl groups, triphenylene groups, dibenzofuranyl groups, dibenzothiophenyl groups, unsubstituted or aryl-substituted carbazolyl groups, or unsubstituted or aryl-substituted benzocarbazolyl groups.
According to one embodiment of the present disclosure, Ar1 to Ar4, Ar11, Ar12, Ar21 and Ar22 are the same or different from each other, and may each independently be any one selected from the following structures.
The structure may be unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heterocyclic group.
In accordance with one embodiment of the present specification,
may be any one selected from the following structures.
The structure may be unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heterocyclic group.
According to one embodiment of the present disclosure, the compound of chemical formula 1 may be any one selected from the following compounds.
According to one embodiment of the present disclosure, the compound of chemical formula 1 may be any one selected from the following compounds.
According to one embodiment of the present disclosure, the compound of chemical formula 1 may be any one selected from the following compounds.
According to one embodiment of the present disclosure, the compound of chemical formula 1 may be any one selected from the following compounds.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 2, a is-NAr 1Ar2, and at least one of Ar1 and Ar2 is a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted benzocarbazolyl group, and the remainder is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond, arylene or heteroarylene, m is an integer of 1 to 2, a is-NAr 1Ar2, and at least one of Ar1 and Ar2 is unsubstituted or aryl-substituted carbazolyl or unsubstituted or aryl-substituted benzocarbazolyl, and the remainder is substituted or unsubstituted aryl.
According to one embodiment of the present disclosure, the compound of chemical formula 1 may be any one selected from the following compounds.
According to one embodiment of the present specification, in chemical formula 1, a is 1 to 10, at least one of R1 is represented by- (L) m-a, L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 10, and a is a substituted or unsubstituted N-containing heterocyclic group.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, m is 1 or 2, and a is a substituted or unsubstituted N-containing heterocyclic group.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, and a is an N-containing heterocyclic group which is unsubstituted or substituted with an aryl group or a heterocyclic group.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, and a is an N-containing heterocyclic group which is unsubstituted or substituted with an aryl group or a heterocyclic group, and herein, the N-containing heterocyclic group is triazinyl, pyrimidinyl, pyridyl, quinazolinyl, quinolyl, isoquinolyl, benzimidazolyl, carbazolyl or benzocarbazolyl.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, and a is an aryl group having 6 to 20 carbon atoms or an N-containing heterocyclic group which is unsubstituted or substituted with a heterocyclic group containing N, O or S and having 2 to 20 carbon atoms, and herein, the N-containing heterocyclic group is triazinyl, pyrimidinyl, pyridyl, quinazolinyl, quinolyl, isoquinolyl, benzimidazolyl, carbazolyl or benzocarbazolyl.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond, phenylene or biphenylene, m is 1 or 2, and a is phenyl, naphthyl, biphenyl, unsubstituted or phenyl-or naphthyl-substituted carbazolyl, unsubstituted or phenyl-or naphthyl-substituted benzocarbazolyl, dibenzothienyl, or unsubstituted or dibenzofuranyl-substituted N-containing heterocyclic group, and herein, the N-containing heterocyclic group is triazinyl, pyrimidinyl, pyridyl, quinazolinyl, quinolyl, isoquinolyl, benzimidazolyl, carbazolyl or benzocarbazolyl.
According to one embodiment of the present disclosure, the compound of chemical formula 1 may be any one selected from the following compounds.
According to one embodiment of the present disclosure, the compound of chemical formula 1 may be any one selected from the following compounds.
According to one embodiment of the present disclosure, the compound of chemical formula 1 may be any one selected from the following compounds.
According to one embodiment of the present specification, in chemical formula 1, a is 1 to 10, at least one of R1 is represented by- (L) m-a, L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 10, a is-P (═ O) R5R6, and R5 and R6 are the same as or different from each other and each independently is a substituted or unsubstituted aryl group.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond, or a substituted or unsubstituted arylene group, m is 1 or 2, a is-P (═ O) R5R6, and R5 and R6 are the same as or different from each other and each independently is a substituted or unsubstituted aryl group.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond, or an arylene group having 6 to 20 carbon atoms, m is 1 or 2, a is-P (═ O) R5R6, and R5 and R6 are the same as or different from each other and each independently an aryl group having 6 to 20 carbon atoms.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is phenylene, m is 1 or 2, a is-P (═ O) R5R6, and R5 and R6 are each phenyl groups.
According to one embodiment of the present disclosure, the compound of chemical formula 1 may be any one selected from the following compounds.
According to one embodiment of the present specification, in chemical formula 1, a is 1 to 10, at least one of R1 is represented by- (L) m-a, L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, m is an integer of 1 to 10, and a is a substituted or unsubstituted anthryl group, or an aryl group substituted with a halogen group or a nitrile group.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, m is 1 or 2, and a is a substituted or unsubstituted anthryl group, or an aryl group substituted with a halogen group or a nitrile group.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond, arylene or heteroarylene, m is 1 or 2, and a is an anthracene group substituted with an aryl group which is unsubstituted or substituted with a halogen group or a nitrile group, or an aryl group substituted with a halogen group or a nitrile group.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond or arylene group, m is 1 or 2, and a is an anthracene group substituted with an aryl group which is unsubstituted or substituted with a fluorine group or a nitrile group, or an aryl group substituted with a fluorine group or a nitrile group.
According to one embodiment of the present specification, in chemical formula 1, a is 1 or 2, at least one of R1 is represented by- (L) m-a, L is a direct bond, m is 1 or 2, and a is an anthracene group substituted with a phenyl group which is unsubstituted or substituted with a nitrile group, or a phenyl group substituted with a fluorine group or a nitrile group.
According to one embodiment of the present disclosure, the compound of chemical formula 1 may be any one selected from the following compounds.
The compound represented by chemical formula 1 may be prepared based on the following preparation examples.
According to one embodiment, the compound represented by chemical formula 1 may be prepared by a procedure such as the following reaction formulas 1-1, 1-2 and 1-3.
[ reaction formula 1-1]
[ reaction formulae 1-2]
[ reaction formulae 1 to 3]
In the reaction scheme, the reaction is carried out,
ar1, Ar2, Ar3 and Ar4 are defined as in chemical formula 1.
Examples of the preparation of compounds having specific substituents at specific positions are described in equations 1-1, 1-2 and 1-3, but those skilled in the art can modify the positions, types and numbers of substituents with reference to the above equations using materials known in the art.
In addition, the present specification provides an organic light emitting device including the compound represented by chemical formula 1.
One embodiment of the present specification provides an organic light emitting device including a first electrode; a second electrode disposed opposite the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the compound of chemical formula 1.
The organic material layer of the organic light emitting device of the present specification may be formed in a single layer structure, but may also be formed in a multilayer structure in which two or more organic material layers are laminated. For example, the organic light emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as organic material layers. However, the structure of the organic light emitting device is not limited thereto, but may include a smaller number of organic material layers.
In one embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, the hole transport layer, or the layer simultaneously performing hole injection and transport includes the compound of chemical formula 1.
In one embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound of chemical formula 1.
In another embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of chemical formula 1.
In one embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound of chemical formula 1.
In one embodiment of the present specification, the electron transport layer, the electron injection layer, or the layer simultaneously performing electron transport and electron injection includes the compound of chemical formula 1.
In another embodiment, the organic material layer includes a light emitting layer and an electron transport layer, and the electron transport layer includes the compound of chemical formula 1.
One embodiment of the present specification provides an organic light emitting device including a first electrode; a second electrode disposed opposite the first electrode; a light emitting layer disposed between the first electrode and the second electrode; and two or more organic material layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the compound. In one embodiment, as the two or more organic material layers, two or more may be selected from an electron transport layer, an electron injection layer, a layer simultaneously performing electron transfer and electron injection, and a hole blocking layer.
In one embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound. Specifically, in one embodiment of the present specification, the compound may be included in one of two or more electron transport layers, or may be included in each of two or more electron transport layers.
In one embodiment of the present specification, when the compound is contained in each of two or more electron transport layers, materials other than the compound may be the same as or different from each other.
In another embodiment, the organic light emitting device may be an organic light emitting device having a structure (conventional type) in which an anode, one or more organic material layers, and a cathode are sequentially laminated on a substrate.
In another embodiment, the organic light emitting device may be an organic light emitting device having a reverse structure (inverted type) in which a cathode, one or more organic material layers, and an anode are sequentially laminated on a substrate.
For example, the structure of an organic light emitting device according to an embodiment of the present specification is shown in fig. 1 and 2.
Fig. 1 shows an organic light-emitting device formed of a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4). In such a structure, the compound may be contained in the light-emitting layer.
Fig. 2 shows an organic light-emitting device formed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron transport layer (7), and a cathode (4). In such a structure, the compound may be included in one or more layers of a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.
According to one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following chemical formula 15.
[ chemical formula 15]
In the chemical formula 15, the first and second compounds,
z1 is an integer of 1 or more, and when z1 is 2 or more, the structures in parentheses are the same as or different from each other,
ar100 is a substituted or unsubstituted monovalent or higher benzofluorenyl group, a substituted or unsubstituted monovalent or higher fluoranthenyl group, a substituted or unsubstituted monovalent or higher pyrenyl group, or a substituted or unsubstituted monovalent or higher pyrenyl group
The base group is a group of a compound,
l100 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, and
r100 and R101 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group, or may be bonded to each other to form a substituted or unsubstituted ring.
According to one embodiment of the present specification, the light emitting layer includes the compound represented by chemical formula 15 as a dopant of the light emitting layer.
According to one embodiment of the present description, L100 is a direct bond.
According to one embodiment of the present description, z1 is 2.
According to one embodiment of the present description, Ar100 is a divalent pyrenyl group unsubstituted or substituted with deuterium, methyl, ethyl, isopropyl, or tert-butyl; or divalent unsubstituted or substituted by deuterium, methyl, ethyl, isopropyl or tert-butyl
And (4) a base.
According to one embodiment of the present description, Ar100 is a divalent pyrenyl group unsubstituted or substituted with deuterium, methyl, ethyl, isopropyl or tert-butyl.
According to one embodiment of the present description, Ar100 is a divalent pyrenyl group.
According to one embodiment of the present specification, R100 and R101 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
According to one embodiment of the present description, R100 and R101 are the same or different from each other and are each independently an aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted with deuterium, an alkyl group, a nitrile group, an aryl group, an alkylsilyl group or an alkylgermanium group; or a heterocyclic group having 2 to 60 carbon atoms which is unsubstituted or substituted with deuterium, an alkyl group, a nitrile group, an aryl group, an alkylsilyl group or an alkylgermanium group.
According to one embodiment of the present description, R100 and R101 are the same or different from each other and are each independently an aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted with deuterium, methyl, ethyl, isopropyl, tert-butyl, nitrile group, phenyl, trimethylsilyl or trimethylgermanium group; or a heterocyclic group having 2 to 60 carbon atoms which is unsubstituted or substituted with deuterium, methyl, ethyl, isopropyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium group.
According to one embodiment of the present description, R100 and R101 are the same or different from each other and are each independently phenyl unsubstituted or substituted with deuterium, methyl, ethyl, isopropyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium; biphenyl unsubstituted or substituted with deuterium, methyl, ethyl, isopropyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium groups; a terphenyl group unsubstituted or substituted with deuterium, methyl, ethyl, isopropyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium group; or a dibenzofuranyl radical which is unsubstituted or substituted by deuterium, methyl, ethyl, isopropyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium.
According to one embodiment of the present description, R100 and R101 are the same or different from each other and are each independently phenyl unsubstituted or substituted with trimethylgermanium groups.
According to one embodiment of the present specification, R100 is phenyl.
According to one embodiment of the present description, R101 is phenyl substituted with trimethylgermanium.
According to one embodiment of the present specification, chemical formula 15 may be selected from the following compounds.
According to one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following chemical formula 16.
[ chemical formula 16]
In the chemical formula 16, the first and second,
ar101 and Ar102 are the same as or different from each other and each independently is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,
l101 and L102 are the same as or different from each other and each independently is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
r102 is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted aralkylamino group, a substituted or unsubstituted alkoxylamine group, a substituted or unsubstituted aminoalkylamine group, a substituted or unsubstituted alkoxylamine group, a substituted or unsubstituted, A substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
z2 and z3 are the same as or different from each other and are each independently an integer of 1 or 2, z4 is an integer of 0 to 8, and when z2 to z4 are 2 or more, substituents in parentheses are the same as or different from each other,
v is an integer of 1 or more, and when v is an integer of 2 or more, the substituents in parentheses are the same as or different from each other.
According to one embodiment of the present specification, the light emitting layer includes the compound represented by chemical formula 16 as a host of the light emitting layer.
According to one embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
According to one embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently is an aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; or a heterocyclic group having 2 to 60 carbon atoms which is unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group.
According to one embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each is independently phenyl unsubstituted or substituted with an aryl group or a heterocyclic group; biphenyl, unsubstituted or substituted with aryl or heterocyclyl; a terphenyl group unsubstituted or substituted with an aryl or heterocyclic group; naphthyl unsubstituted or substituted with aryl or heterocyclyl; fluorenyl, unsubstituted or substituted with alkyl, aryl or heterocyclyl groups; phenanthryl unsubstituted or substituted with aryl or heterocyclyl; or triphenylene which is unsubstituted or substituted by an aryl or heterocyclic group.
According to one embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group which is unsubstituted or substituted with a methyl group or a phenyl group, a phenanthryl group, or a triphenylene group.
According to one embodiment of the present description, Ar101 is 2-naphthyl.
According to one embodiment of the present description, Ar102 is 1-naphthyl.
According to one embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently is a direct bond, phenylene or naphthylene.
According to one embodiment of the present description, L101 is phenylene.
According to one embodiment of the present specification, L102 is a direct bond.
According to one embodiment of the present description, R102 is hydrogen.
According to one embodiment of the present description, z2 is 1.
According to one embodiment of the present description, v is 1.
According to one embodiment of the present description, v is 2.
According to one embodiment of the present specification, chemical formula 16 may be selected from the following compounds.
According to one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by chemical formula 15 as a dopant of the light emitting layer and includes the compound represented by chemical formula 16 as a host of the light emitting layer.
The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that one or more of the organic material layers include the compound of the present specification, i.e., the compound of chemical formula 1.
When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same or different materials from each other.
The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that one or more of the organic material layers include the compound of chemical formula 1, i.e., the compound represented by chemical formula 1.
For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. Herein, the organic light emitting device may be manufactured by the following process: depositing a metal, a metal oxide having conductivity, or an alloy thereof using a Physical Vapor Deposition (PVD) method such as sputtering or electron beam evaporation to form an anode on a substrate; forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon; and then a material capable of functioning as a cathode is deposited thereon. In addition to such a method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
In addition, when the organic light emitting device is manufactured, the compound of chemical formula 1 may be formed into an organic material layer using a solution coating method and a vacuum deposition method. Here, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, etc., but is not limited thereto.
In addition to such a method, an organic light emitting device may be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (international patent publication No. 2003/012890). However, the manufacturing method is not limited thereto.
In one embodiment of the present description, the first electrode is an anode and the second electrode is a cathode.
In another embodiment, the first single agent is the cathode and the second electrode is the anode.
As the anode material, a material having a large work function is generally preferable so that holes are smoothly injected into the organic material layer. Specific examples of anode materials that can be used in the present disclosure include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO: Al or SnO2Sb; conducting polymers, e.g. poly (3-methylthiophene), poly [3,4- (methylenedioxy)Ethyl-1, 2-dioxy) thiophene](PEDOT), polypyrrole, polyaniline, and the like, but are not limited thereto.
As the cathode material, a material having a small work function is generally preferable so that electrons are smoothly injected into the organic material layer. Specific examples of cathode materials that can be used in the present disclosure include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO2Al, etc., but are not limited thereto.
The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound of: it has an ability to transport holes to have a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from migrating to an electron injection layer or an electron injection material, and in addition, has an excellent thin film forming ability. The Highest Occupied Molecular Orbital (HOMO) of the hole injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic material, hexanenitrile-based hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, and polyaniline-and polythiophene-based conductive polymer, etc., but are not limited thereto.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and as a hole transport material, a material that can receive holes from the anode or the hole injection layer, transport the holes to the light emitting layer, and has high mobility to the holes is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, a block copolymer having both a conjugated portion and a non-conjugated portion, and the like, but are not limited thereto.
The light emitting material is a material capable of emitting light in a visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and the electrons, and is preferably a material having good quantum efficiency for fluorescence or phosphorescence. It is embodied in the form ofExamples include: 8-Hydroxyquinoline aluminum Complex (Alq)3) (ii) a A carbazole-based compound; a di-polystyrene based compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; based on benzene
Compounds of oxazole, benzothiazole and benzimidazole; polymers based on poly (p-phenylene vinylene) (PPV); a spiro compound; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. Host materials include fused aromatic ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the fused aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocycle-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, and the like, but the material is not limited thereto.
Dopant materials include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group and includes pyrene, anthracene, perylene, and the like containing an arylamine group,
And diindenopyrene, etc., and the styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one, two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, the styrylamine compound includes, but is not limited to, styrylamine, styrenediamine, styrenetriamine, styrenetetramine, and the like. Further, the metal complex includes iridium complex, platinum complex, and the like, but is not limited thereto.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and as an electron transport material, can well receive electrons from the electron injection layerElectrons of the cathode, a material that transports the electrons to the light-emitting layer and has high mobility to the electrons are suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline, Al complexes containing Alq3The complex of (2), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode materials include, in particular, common materials with a small work function, followed by an aluminum or silver layer. In particular, the cathode material comprises cesium, barium, calcium, ytterbium and samarium, and is in each case followed by an aluminum or silver layer.
The electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound of: which has an ability to transport electrons, has an electron injection effect from a cathode and has an excellent electron injection effect on a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from migrating to a hole injection layer, and, in addition, has an excellent thin film forming ability. Specific examples thereof include fluorenones, anthraquinone dimethanes, diphenoquinones, thiopyran dioxides, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, etc., and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, etc., but not limited thereto.
The metal complex compound includes lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), chlorogallium bis (2-methyl-8-quinolinolato), gallium bis (2-methyl-8-quinolinolato) (o-cresol), aluminum bis (2-methyl-8-quinolinolato) (1-naphthol), gallium bis (2-methyl-8-quinolinolato) (2-naphthol), and the like, but is not limited thereto.
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-side emission type, depending on the material used.
In one embodiment of the present specification, the compound of chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
The preparation of the compound represented by chemical formula 1 and the fabrication of an organic light emitting device including the same will be specifically described with reference to the following examples. However, the following examples are for illustrative purposes only, and the scope of the present specification is not limited thereto.
< Synthesis example 1>
< preparation example 1>
Synthesis of Compound 1
After completely dissolving compound a (10.0g, 17.83mmol) and diphenylamine (3.31g, 19.61mmol) in 180ml of xylene in a 500ml round bottom flask under nitrogen atmosphere, sodium tert-butoxide (2.05g, 21.39mol) was added thereto, then bis (tri-tert-butylphosphine) palladium (0) (0.09g, 0.18mmol) was added, and the resultant was heated and stirred for 2 hours. The resultant was cooled to room temperature, filtered to remove the base, and then the xylene was concentrated in vacuo. The resultant was recrystallized from 150ml of ethyl acetate to prepare Compound 1(8.85g, yield: 77%).
MS[M+H]+＝650
< preparation example 2>
Synthesis of Compound 2
After completely dissolving compound A (10.0g, 17.83mmol) and N-phenyl- [1, 1' -biphenyl ] -4-amine (4.80g, 19.61mmol) in 200ml of xylene in a 500ml round bottom flask under nitrogen atmosphere, sodium tert-butoxide (2.05g, 21.39mol) was added thereto, then bis (tri-tert-butylphosphine) palladium (0) (0.09g, 0.18mmol) was added, and the resultant was heated and stirred for 3 hours. The resultant was cooled to room temperature, filtered to remove the base, and then the xylene was concentrated in vacuo. The resultant was recrystallized from 200ml of ethyl acetate to prepare Compound 2(9.42g, yield: 73%).
MS[M+H]+＝726
< preparation example 3>
Synthesis of Compound 3
After completely dissolving compound a (10.0g, 17.83mmol) and bis ([1, 1' -biphenyl ] -4-yl) amine (6.29g, 19.61mmol) in 220ml of xylene in a 500ml round bottom flask under nitrogen atmosphere, sodium tert-butoxide (2.05g, 21.39mol) was added thereto, then bis (tri-tert-butylphosphine) palladium (0) (0.09g, 0.18mmol) was added, and the resultant was heated and stirred for 4 hours. The resultant was cooled to room temperature, filtered to remove the base, and then the xylene was concentrated in vacuo. The resultant was recrystallized from 250ml of ethyl acetate to prepare Compound 3(12.22g, yield: 86%).
MS[M+H]+＝803
< preparation example 4>
Synthesis of Compound 4 below
After completely dissolving compound a (10.0g, 17.83mmol) and N- ([1,1 '-biphenyl ] -4-yl) - [1, 1' -biphenyl ] -2-amine (6.29g, 19.61mmol) in 220ml xylene under a nitrogen atmosphere in a 500ml round bottom flask, sodium tert-butoxide (2.05g, 21.39mol) was added thereto, followed by bis (tri-tert-butylphosphine) palladium (0) (0.09g, 0.18mmol), and the resultant was heated and stirred for 3 hours. The resultant was cooled to room temperature, filtered to remove the base, and then the xylene was concentrated in vacuo. The resultant was recrystallized from 230ml of ethyl acetate to prepare Compound 4(11.01g, yield: 77%).
MS[M+H]+＝803
< preparation example 5>
Synthesis of Compound 5 below
After completely dissolving compound a (10.0g, 17.83mmol) and N- ([1, 1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoren-2-amine (7.08g, 19.61mmol) in 240ml of xylene under a nitrogen atmosphere in a 500ml round bottom flask, sodium tert-butoxide (2.05g, 21.39mol) was added thereto, followed by bis (tri-tert-butylphosphine) palladium (0) (0.09g, 0.18mmol), and the resultant was heated and stirred for 5 hours. The resultant was cooled to room temperature, filtered to remove the base, and then the xylene was concentrated in vacuo. The resultant was recrystallized from 280ml of ethyl acetate to prepare Compound 5(11.32g, yield: 76%).
MS[M+H]+＝843
< preparation example 6>
Synthesis of Compound 6
After completely dissolving compound a (10.0g, 17.83mmol) and N- ([1, 1' -biphenyl ] -2-yl) -9, 9-dimethyl-9H-fluoren-2-amine (7.08g, 19.61mmol) in 220ml xylene under nitrogen atmosphere in a 500ml round bottom flask, sodium tert-butoxide (2.05g, 21.39mol) was added thereto, followed by bis (tri-tert-butylphosphine) palladium (0) (0.09g, 0.18mmol), and the resultant was heated and stirred for 3 hours. The resultant was cooled to room temperature, filtered to remove the base, and then the xylene was concentrated in vacuo. The resultant was recrystallized from 240ml of ethyl acetate to prepare Compound 6(10.19g, yield: 68%).
MS[M+H]+＝843
< preparation example 7>
Synthesis of Compound 7 below
After completely dissolving compound a (10.0g, 17.83mmol) and 9, 9-dimethyl-N-phenyl-9H-fluoren-2-amine (5.59g, 19.61mmol) in 220ml xylene under nitrogen in a 500ml round bottom flask, sodium tert-butoxide (2.05g, 21.39mol) was added thereto, then bis (tri-tert-butylphosphine) palladium (0) (0.09g, 0.18mmol) was added, and the resultant was heated and stirred for 3 hours. The resultant was cooled to room temperature, filtered to remove the base, and then the xylene was concentrated in vacuo. The resultant was recrystallized from 240ml of ethyl acetate to prepare Compound 7(10.02g, yield: 75%).
MS[M+H]+＝767
< preparation example 8>
Synthesis of Compound 8
After completely dissolving compound a (10.0g, 17.83mmol) and (4- (diphenylamino) phenyl) boronic acid (5.92g, 20.50mmol) in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, a 2M potassium carbonate aqueous solution (110ml) was added thereto, followed by tetrakis (triphenylphosphine) palladium (0.21g, 0.18mmol), and the resultant was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated in vacuo, and then recrystallized from 210ml of ethyl acetate to prepare compound 8(9.97g, 77%).
MS[M+H]+＝726
< preparation example 9>
Synthesis of Compound 9
After completely dissolving compound a (10.0g, 17.83mmol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (5.92g, 20.50mmol) in 260ml tetrahydrofuran under nitrogen in a 500ml round bottom flask, a 2M aqueous potassium carbonate solution (130ml) was added thereto, followed by tetrakis (triphenylphosphine) palladium (0.21g, 0.18mmol), and the resultant was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated in vacuo, and then recrystallized from 280ml of ethyl acetate to prepare compound 9(10.47g, 81%).
MS[M+H]+＝724
< preparation example 10>
Synthesis of Compound 10 below
After completely dissolving compound a (10.0g, 17.83mmol) and (4- (diphenylphosphoryl) phenyl) boronic acid (6.60g, 20.50mmol) in 220ml of tetrahydrofuran under a nitrogen atmosphere in a 500ml round-bottom flask, a 2M potassium carbonate aqueous solution (110ml) was added thereto, followed by tetrakis (triphenylphosphine) palladium (0.21g, 0.18mmol), and the resultant was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated in vacuo, and then recrystallized from 210ml of ethyl acetate to prepare compound 10(11.46g, 85%).
MS[M+H]+＝759
< preparation example 11>
Synthesis of Compound 11
After completely dissolving compound A-1(10.0g, 16.50mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.83g, 14.34mmol) in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added thereto, followed by tetrakis (triphenylphosphine) palladium (0.17g, 0.14mmol), and the resultant was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated in vacuo, and then recrystallized from 210ml of ethyl acetate to prepare compound 11(9.44g, 80%).
MS[M+H]+＝714
< preparation example 12>
Synthesis of Compound 12
After completely dissolving compound A-1(10.0g, 16.50mmol) and 2-chloro-4, 6-diphenylpyrimidine (3.83g, 14.34mmol) in 280ml of tetrahydrofuran in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (140ml) was added thereto, followed by tetrakis (triphenylphosphine) palladium (0.17g, 0.14mmol), and the resultant was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated in vacuo, and then recrystallized from 230ml of ethyl acetate to prepare compound 12(8.49g, 71%).
MS[M+H]+＝713
< preparation example 13>
Synthesis of Compound 13
After completely dissolving compound A-1(10.0g, 16.50mmol) and 4-chloro-4, 6-diphenylpyrimidine (3.83g, 14.34mmol) in 240ml of tetrahydrofuran under a nitrogen atmosphere in a 500ml round-bottom flask, a 2M aqueous potassium carbonate solution (120ml) was added thereto, followed by tetrakis (triphenylphosphine) palladium (0.17g, 0.14mmol), and the resultant was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated in vacuo, and then recrystallized from 260ml of ethyl acetate to prepare compound 13(7.92g, 67%).
MS[M+H]+＝713
< preparation example 14>
Synthesis of Compound 14
After completely dissolving compound A-1(10.0g, 16.50mmol) and 2-chloro-4, 6-diphenylpyridine (3.83g, 14.34mmol) in 240ml of tetrahydrofuran in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added thereto, followed by tetrakis (triphenylphosphine) palladium (0.17g, 0.14mmol), and the resultant was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the resultant was dried over anhydrous magnesium sulfate, concentrated in vacuo, and then recrystallized from 210ml of ethyl acetate to prepare compound 14(8.23g, 70%).
MS[M+H]+＝712
< preparation examples 15> to < preparation example 28>
< examples 1 to 1>
Is coated thereon with a thickness of
Indium Tin Oxide (ITO) as a glass substrate of the thin film was put in distilled water in which a detergent was dissolved and subjected to ultrasonic cleaning. Here, a product of Fischer co. was used as a cleaning agent, and distilled water filtered twice by a filter manufactured by Millipore co. was used as distilled water. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeatedly performed twice for 10 minutes using distilled water. After the completion of the cleaning using distilled water, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol solvents, and then dried, and then transferred to a plasma cleaning machine. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then transferred to a vacuum depositor.
On the transparent ITO electrode prepared as above, the following compound, hexacyano-Hexaazatriphenylene (HAT), was formed to a thickness of
The hole injection layer of (1).
[HAT]
The following compound 4-4' -bis [ N- (1-naphthyl) -N-phenylamino was deposited by vacuum as a hole-transporting material]Biphenyl (NPB)
To form a hole transport layer on the hole injection layer.
[NPB]
Subsequently, the following compound 1 was formed on the hole transport layer by vacuum deposition to a film thickness of
The electron blocking layer of (1).
[ Compound 1]
Next, a film thickness of BH and BD shown below was formed on the electron blocking layer by vacuum deposition at a weight ratio of 25:1
The light emitting layer of (1).
The compound ET1 and the compound lithium quinolinate (LiQ) were formed on the light-emitting layer by vacuum deposition at a weight ratio of 1:1 to a thickness of
Electron injection and transport layers. By depositing in sequential order to a thickness of
With a thickness of lithium fluoride (LiF) of
The aluminum of (a) to form a cathode on the electron injection and transport layer.
By maintaining the deposition rate of the organic material at
To
The cathode has a deposition rate of lithium fluoride and aluminum of
And
and the vacuum during deposition was 2 × 10-7Tray to 5 × 10-6And manufacturing the organic light emitting device.
< examples 1 and 2>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 2 was used instead of compound 1.
< examples 1 to 3>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 3 was used instead of compound 1.
< examples 1 to 4>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 4 was used instead of compound 1.
< examples 1 to 5>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 5 was used instead of compound 1.
< examples 1 to 6>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 6 was used instead of compound 1.
< examples 1 to 7>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 7 was used instead of compound 1.
< examples 1 to 8>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 8 was used instead of compound 1.
< examples 1 to 9>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 15 was used instead of compound 1.
< examples 1 to 10>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 16 was used instead of compound 1.
< examples 1 to 11>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 17 was used instead of compound 1.
< examples 1 to 12>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 18 was used instead of compound 1.
< examples 1 to 13>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 19 was used instead of compound 1.
< examples 1 to 14>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 20 was used instead of compound 1.
< examples 1 to 15>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 21 was used instead of compound 1.
< examples 1 to 16>
An organic light-emitting device was produced in the same manner as in example 1-1, except that compound 22 was used instead of compound 1.
< comparative example 1-1>
An organic light-emitting device was produced in the same manner as in example 1-1, except that the following EB 1(TCTA) was used instead of compound 1.
[EB 1]
< comparative examples 1 and 2>
An organic light-emitting device was produced in the same manner as in example 1-1, except that EB 2 was used instead of compound 1.
[EB 2]
When current was applied to the organic light emitting devices manufactured in examples 1-1 to 1-16 and comparative examples 1-1 and 1-2, the results of table 1 below were obtained.
[ Table 1]
As can be seen from table 1, the organic light emitting devices of examples 1-1 to 1-16 using the compound represented by chemical formula 1 as an electron blocking layer in the organic light emitting device exhibited low voltage and high efficiency characteristics, as compared to comparative example 1 using the existing TCTA and comparative example 2 having a core structure similar to chemical formula 1 of the present disclosure.
It is determined that the compound of chemical formula 1 according to the present disclosure has excellent electron blocking ability and exhibits characteristics of low voltage and high efficiency, and thus can be used for an organic light emitting device.
< example 2-1>
The compound synthesized in the synthesis example was purified by high-purity sublimation using a known method, and then a green organic light-emitting device was produced using the following method.
Is coated thereon with a thickness of
Indium Tin Oxide (ITO) as a glass substrate of the thin film was put in distilled water in which a detergent was dissolved and subjected to ultrasonic cleaning. Here, a product of Fischer co. was used as a cleaning agent, and distilled water filtered twice by a filter manufactured by Millipore co. was used as distilled water. After the ITO was cleaned for 30 minutes, ultrasonic cleaning was repeatedly performed twice for 10 minutes using distilled water. After the completion of the cleaning using distilled water, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol solvents, and then dried, and then transferred to a plasma cleaning machine. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then transferred to a vacuum depositor.
By using compound 11 as a host, m-MTDATA (60nm)/TCTA (80 nm)/compound 11+ 10% Ir (ppy)3(300nm)/BCP(10nm)/Alq3(30nm)/LiF (1nm)/Al (200nm) in this order a light emitting element was formed on the transparent ITO electrode prepared as above to fabricate an organic light emitting device.
m-MTDATA、TCTA、Ir(ppy)3And the structure of BCP is as follows.
[ Compound 11]
< examples 2 to 2>
An organic light-emitting device was produced in the same manner as in example 2-1, except that compound 12 was used instead of compound 11.
< examples 2 to 3>
An organic light-emitting device was produced in the same manner as in example 2-1, except that compound 13 was used instead of compound 11.
< examples 2 to 4>
An organic light-emitting device was produced in the same manner as in example 2-1, except that compound 14 was used instead of compound 11.
< examples 2 to 5>
An organic light-emitting device was produced in the same manner as in example 2-1, except that compound 25 was used instead of compound 11.
< examples 2 to 6>
An organic light-emitting device was produced in the same manner as in example 2-1, except that compound 26 was used instead of compound 11.
< examples 2 to 7>
An organic light-emitting device was produced in the same manner as in example 2-1, except that compound 27 was used instead of compound 11.
< examples 2 to 8>
An organic light-emitting device was produced in the same manner as in example 2-1, except that compound 28 was used instead of compound 11.
< comparative example 1>
An organic light-emitting device was fabricated in the same manner as in example 2-1, except that the following GH 1(CBP) was used instead of compound 11.
[GH 1]
< comparative example 2>
An organic light-emitting device was produced in the same manner as in example 2-1, except that the following GH 2 was used instead of compound 11.
[GH 2]
When current was applied to the organic light emitting devices manufactured in examples 2-1 to 2-8 and comparative examples 1 and 2, the results of table 2 below were obtained.
[ Table 2]
From the test results, it was confirmed that the green organic light emitting devices of examples 2-1 to 2-8 using the compound represented by chemical formula 1 according to the present disclosure as a host material of a green light emitting layer exhibited superior performance in terms of current efficiency and driving voltage, as compared to the green organic light emitting device of comparative example 1 using the existing CBP and comparative example 2 having a core structure similar to chemical formula 1 of the present disclosure.
Hereinabove, preferred embodiments (electron blocking layer, green light emitting layer) of the present disclosure are described, however, the present disclosure is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description, and the modifications are also included in the scope of the present disclosure.
Claims (10)
1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
Wherein, in chemical formula 1,
r1 is represented by- (L) m-A,
l is a direct bond; or an arylene group having 6 to 20 carbon atoms,
m is 1, m is a linear chain,
a is-NAr 1Ar2 or an N-containing heterocyclic group which is unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms, and wherein the N-containing heterocyclic group is a triazinyl group, a pyrimidinyl group or a pyridyl group,
ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbons which is unsubstituted or substituted with one or more substituents selected from deuterium and an alkyl group having 1 to 6 carbons,
r2 to R4 are the same or different from each other and are each independently hydrogen or deuterium,
a is 1, and a is a linear alpha-olefin,
b is an integer of 0 to 7,
c is an integer of 0 to 5,
d is an integer of 0 to 4, and
when b, c and d are each 2 or more, the structures in parentheses are the same as or different from each other.
2. The compound according to claim 1, wherein chemical formula 1 is represented by the following chemical formula 2:
[ chemical formula 2]
Wherein, in chemical formula 2,
l, m, Ar1, Ar2, R2 to R4, b, c and d are as defined in chemical formula 1,
r11 has the same definition as R2 to R4,
p is 1, and p is a group of,
f is an integer of 0 to 10,
1≤p+f≤10，
when f is 2 or more, the structures in parentheses are the same as or different from each other.
3. The compound according to claim 1, wherein chemical formula 1 is represented by any one of the following chemical formulae 5 to 8:
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
[ chemical formula 8]
Wherein, in chemical formulas 5 to 8,
r2 to R4, b, c and d are as defined in chemical formula 1,
l1 is a direct bond or an arylene group having 6 to 20 carbon atoms,
ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbons which is unsubstituted or substituted with one or more substituents selected from deuterium and an alkyl group having 1 to 6 carbons,
y1 is hydrogen or deuterium,
y1 is an integer from 0 to 9,
m1 is 1, and
when y1 is 2 or more, the structures in parentheses are the same as or different from each other.
4. The compound of claim 1, wherein the compound of formula 1 is selected from any one of the following structural formulas:
5. the compound of claim 1, wherein the compound of formula 1 is selected from any one of the following structural formulas:
6. the compound of claim 1, wherein the compound of formula 1 is selected from any one of the following structural formulas:
7. an organic light emitting device comprising:
a first electrode;
a second electrode disposed opposite the first electrode; and
one or more layers of organic material disposed between the first electrode and the second electrode,
wherein one or more of the layers of organic material comprise the compound of claim 1,
wherein the organic material layer includes at least one layer 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 the light emitting layer and/or the electron blocking layer contains the compound according to claim 1.
8. The organic light emitting device according to claim 7, wherein the organic material layer comprises a light emitting layer, and the light emitting layer contains a compound represented by the following chemical formula 15:
[ chemical formula 15]
Wherein, in chemical formula 15,
z1 is an integer of 1 or more, and when z1 is an integer of 2 or more, the structures in parentheses are the same as or different from each other,
ar100 is a substituted or unsubstituted monovalent or higher benzofluorenyl group, a substituted or unsubstituted monovalent or higher fluoranthenyl group, a substituted or unsubstituted monovalent or higher pyrenyl group, or a substituted or unsubstituted monovalent or higher pyrenyl group
The base group is a group of a compound,
l100 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, and
r100 and R101 are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group, or are bonded to each other to form a substituted or unsubstituted ring.
9. The organic light emitting device according to claim 7, wherein the organic material layer comprises a light emitting layer, and the light emitting layer contains a compound represented by the following chemical formula 16:
[ chemical formula 16]
Wherein, in chemical formula 16,
ar101 and Ar102 are the same as or different from each other and each independently is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,
l101 and L102 are the same as or different from each other and each independently is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
r102 is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted aralkylamino group, a substituted or unsubstituted alkoxylamine group, a substituted or unsubstituted aminoalkylamine group, a substituted or unsubstituted alkoxylamine group, a substituted or unsubstituted, A substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
z2 and z3 are the same as or different from each other and are each independently an integer of 1 or 2, z4 is an integer of 0 to 8, and when z2 to z4 are 2 or more, substituents in parentheses are the same as or different from each other, and
v is an integer of 1 or more, and when v is an integer of 2 or more, the substituents in parentheses are the same as or different from each other.
10. The organic light emitting device according to claim 8, wherein the light emitting layer comprises a compound represented by the following chemical formula 16:
[ chemical formula 16]
Wherein, in chemical formula 16,
ar101 and Ar102 are the same as or different from each other and each independently is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,
l101 and L102 are the same as or different from each other and each independently is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
r102 is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkenyl group, a substituted or unsubstituted alkylaryl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted aralkylamino group, a substituted or unsubstituted alkoxylamine group, a substituted or unsubstituted aminoalkylamine group, a substituted or unsubstituted alkoxylamine group, a substituted or unsubstituted, A substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
z2 and z3 are the same as or different from each other and are each independently an integer of 1 or 2, z4 is an integer of 0 to 8, and when z2 to z4 are 2 or more, substituents in parentheses are the same as or different from each other, and
v is an integer of 1 or more, and when v is an integer of 2 or more, the substituents in parentheses are the same as or different from each other.
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| KR1020160130731A KR102000177B1 (en) | 2015-10-26 | 2016-10-10 | Compound having spiro structure and organic light emitting device comprising the same |
| PCT/KR2016/011421 WO2017073933A1 (en) | 2015-10-26 | 2016-10-12 | Spiro-type compound and organic light emitting element comprising same |
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