CN117616006A - Compound and organic light emitting device comprising the same - Google Patents
Compound and organic light emitting device comprising the same Download PDFInfo
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- CN117616006A CN117616006A CN202380012490.4A CN202380012490A CN117616006A CN 117616006 A CN117616006 A CN 117616006A CN 202380012490 A CN202380012490 A CN 202380012490A CN 117616006 A CN117616006 A CN 117616006A
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 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
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 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
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 239000011630 iodine Substances 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
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 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
- 239000011133 lead Substances 0.000 description 1
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- BGTFRFFRQKBWLS-UHFFFAOYSA-M lithium;quinolin-2-olate Chemical compound [Li+].C1=CC=CC2=NC([O-])=CC=C21 BGTFRFFRQKBWLS-UHFFFAOYSA-M 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000000203 mixture Substances 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
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-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
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- NQFOGDIWKQWFMN-UHFFFAOYSA-N phenalene Chemical compound C1=CC([CH]C=C2)=C3C2=CC=CC3=C1 NQFOGDIWKQWFMN-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 150000004882 thiopyrans Chemical class 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
- 238000012546 transfer Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 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
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- C07C211/57—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 carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—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 carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- 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
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- 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
- C07C211/57—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 carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/60—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 carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton containing a ring other than a six-membered aromatic ring forming part of at least one of the condensed ring systems
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- 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
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- 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
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- 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
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- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/18—Carrier blocking layers
- H10K50/181—Electron blocking layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/95—Spiro compounds containing "not free" spiro atoms
- C07C2603/96—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members
- C07C2603/97—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members containing five-membered rings
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Abstract
The present specification provides a compound represented by chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present application claims priority from korean patent application No. 10-2022-0045344, filed to the korean patent office on 12 months of 2022, the entire contents of the disclosure of which are incorporated herein by reference.
The present specification relates to a compound and an organic light emitting device including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
Prior art literature
Patent literature
(patent document 1) KR 10-2014-007688
Disclosure of Invention
Technical problem
The present specification provides compounds and organic light emitting devices comprising the same.
Solution to the problem
An embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
r1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
at least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms,
at least one of R2 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
ar1 and Ar2 are the same as or different from each other, each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
l1 to L3 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group having a valence of 2,
a is an integer of 1 to 8, R1 are the same or different from each other when a is 2 or more,
b is an integer of 1 to 3, and when b is 2 or more, R2 are the same or different from each other.
In addition, an embodiment of the present specification provides an organic light emitting device, including: an anode, a cathode, and 1 or more organic layers provided between the anode and the cathode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compounds described in the present specification can be used as materials for organic layers of organic light-emitting devices. The compound according to at least one embodiment of the present specification may achieve an improvement in efficiency, a lower driving voltage, and/or an improvement in lifetime characteristics in an organic light emitting device. In particular, the compounds described in this specification can be used as a material for hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection. In addition, it has effects of low driving voltage, high efficiency and/or long life compared to the existing organic light emitting device.
Drawings
Fig. 1 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, an organic layer 10, and a cathode 9 are stacked in this order.
Fig. 2 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 9 are stacked in this order.
[ description of the symbols ]
1: substrate board
2: anode
3: hole injection layer
4: hole transport layer
5: electron blocking layer
6: light-emitting layer
7: hole blocking layer
8: electron injection and transport layers
9: cathode electrode
10: organic layer
Detailed Description
The present specification will be described in more detail below.
In the present specification, when a certain component is referred to as "including/comprising" a certain component, unless otherwise specified, it means that other components may be further included, rather than excluded.
In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.
In the present specification, examples of substituents are described below, but are not limited thereto.
The term "substituted" as used herein means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with a member selected from deuterium, halogen group, nitrile group (-CN), nitro, hydroxy, alkyl, cycloalkyl, alkoxy, phosphine oxide group, aryloxy, alkylthio groupArylthio groupsAlkylsulfonyl->Arylsulfonyl->1 or more substituents selected from alkenyl, silyl, boron, amino, aryl and heterocyclic groups, or a substituent obtained by linking 2 or more substituents selected from the above-exemplified substituents, or a substituent not having any substituent. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen group, nitrile group, nitro group, hydroxyl group, amino group, silyl group, boron group, alkoxy group, aryloxy group, alkyl group, cycloalkyl group, aryl group, and heterocyclic group, or substituted with a substituent in which 2 or more substituents selected from the above-exemplified substituents are linked, or does not have any substituent.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen groups, nitrile groups, alkyl groups, aryl groups, and heterocyclic groups, or substituted with a substituent in which 2 or more substituents out of the above-exemplified substituents are linked, or does not have any substituent.
Examples of the above substituents are described below, but are not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
In the present specification, the silyl group may be represented by-SiY a Y b Y c The chemical formula of (A) is shown in the specification, Y is shown in the specification a 、Y b And Y c Each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically, but not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group may be represented BY-BY d Y e The chemical formula of (A) is shown in the specification, Y is shown in the specification d And Y e Each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Examples of the boron group include trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but are not limited thereto.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, and the like.
In this specification, the above description of the alkyl group may be applied to the arylalkyl group other than the aryl group.
In the present specification, the above-mentioned alkoxy group may be a straight chain, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy and the like are possible, but not limited thereto.
The alkyl groups, alkoxy groups, and other substituents containing an alkyl moiety described in this specification are all included in straight or branched chain forms.
In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylen-1-yl, 2-diphenylethylene-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene-1-yl, 2-bis (diphenyl-1-yl) ethylene-1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, the alkynyl group is a substituent group including a triple bond between carbon atoms, and may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkynyl group has 2 to 20 carbon atoms. According to another embodiment, the above alkynyl group has 2 to 10 carbon atoms.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like, but not limited thereto.
In the present specification, the amine group is-NH 2 The amine group may be substituted with the alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, a combination thereof, or the like. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the amine group has 1 to 20 carbon atoms. According to one embodiment, the amine group has 1 to 10 carbon atoms. Specific examples of the substituted amine group include, but are not limited to, methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamino group, 9-dimethylfluorenylphenylamino group, pyridylphenylamino group, diphenylamino group, phenylpyridylamino group, naphthylamino group, biphenylamino group, anthracenyl amino group, dibenzofuranylphenylamino group, 9-methylanthracenylamino group, diphenylamino group, phenylnaphthylamino group, xylylamino group, phenyltolylamino group, and diphenylamino group.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as phenyl, biphenyl, terphenyl, or tetrabiphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenyl,Radicals, fluorenyl radicals, triphenylene radicals, and the likeHowever, the present invention is not limited thereto.
In the present specification, the substituted aryl group may include a form in which an aliphatic ring is condensed on the aryl group. For example, tetrahydronaphthyl of the following structure is included in the substituted aryl group. In the following structures, one of the carbon atoms of the benzene ring may be attached to the other position.
In the present specification, the aryl group in the aryloxy group may be applied to the above description about the aryl group.
In the present specification, the above-mentioned alkyl groups in the alkylthio group and the alkylsulfonyl group may be applied to the above-mentioned explanation about the alkyl group.
In the present specification, the above-described aryl groups in the arylthio group and the arylsulfonyl group can be applied to the above-described description about the aryl group.
In the present specification, the heterocyclic group is a ring group containing 1 or more heteroatoms in N, O, P, S, si and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to one embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarzolyl, triazinyl, and the like.
In this specification, the heteroaryl group is aromatic, and the above description of the heterocyclic group can be applied thereto.
In the present specification, the arylene group is not limited to 2, and the description of the aryl group may be applied.
In this specification, the heterocyclic ring having 2 valences may be applied to the above description of the heterocyclic group, except that the heterocyclic ring has 2 valences.
In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a hydrocarbon ring or a heterocyclic ring.
The hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic group and an aliphatic ring, and may be selected from the examples of cycloalkyl groups and aryl groups.
In the present specification, the meaning of forming a ring by bonding adjacent groups to each other means that 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 condensed rings thereof are formed by bonding adjacent groups to each other. The hydrocarbon ring refers to a ring composed of only carbon and hydrogen atoms. The heterocyclic ring is a ring containing 1 or more elements selected from N, O, P, S, si and Se. 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.
In the present specification, the aliphatic hydrocarbon ring means a ring which is not aromatic and is composed of only carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1, 4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like.
In the present specification, an aromatic hydrocarbon ring means an aromatic ring composed of only carbon and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, and, Pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, and the like, but is not limited thereto. In the present specification, an aromatic hydrocarbon ring can be interpreted as having the same meaning as an aryl group.
In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing 1 or more hetero atoms. Examples of aliphatic heterocycles include ethylene oxide (oxalane), tetrahydrofuran, and 1, 4-di-Alkyl (1, 4-dioxane), pyrrolidine, piperidine, morpholine, oxepane> Azacyclooctane->Thiocyclooctane->And the like, but is not limited thereto.
In the present specification, an aromatic heterocycle means an aromatic ring containing 1 or more hetero atoms. Examples of the aromatic heterocyclic ring include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, and the like,Azole, i->Oxazole, thiazole, isothiazole, triazole, < >>Diazoles, thiadiazoles, dithiazoles, tetrazoles, pyrans, thiopyrans, pyridazines,/->Oxazine, thiazide, di->Alkene, triazine, tetrazine, isoquinoline, quinoline, benzoquinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazaindene, indole, indolizine, benzothiazole, benzo->Oxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, pheno- >Oxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.
Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiment of the present invention may be modified into various forms, and the scope of the present invention is not limited to the embodiment described below.
The compound represented by chemical formula 1 according to the present invention can adjust HOMO and LUMO energy levels of the compound by attaching an amine group to tetralin, thereby adjusting an energy barrier with an organic layer.
In particular, the compound represented by chemical formula 1 according to the present invention may adjust the hole transporting property of the compound by having an alkyl substituent of 1 to 3 carbon atoms on tetrahydronaphthalene or an alkyl or aryl substituent on the benzene ring moiety of tetrahydronaphthalene, thereby adjusting the balance of holes and electrons of the device.
Accordingly, when the compound represented by the above chemical formula 1 is applied to an organic light emitting device, an organic light emitting device having high efficiency, low voltage, and/or long life characteristics can be obtained.
Chemical formula 1 will be described in detail below.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
r1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
At least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms,
at least one of R2 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
ar1 and Ar2 are the same as or different from each other, each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
l1 to L3 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group having a valence of 2,
a is an integer of 1 to 8, R1 are the same or different from each other when a is 2 or more,
b is an integer of 1 to 3, and when b is 2 or more, R2 are the same or different from each other.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, an alkyl group having 1 to 60 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 12 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, an alkyl group of 1 to 3 carbon atoms substituted or unsubstituted with deuterium, or an aryl group of 6 to 20 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, an alkyl group of 1 to 3 carbon atoms substituted or unsubstituted with deuterium, or an aryl group of 6 to 12 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, an alkyl group of 1 to 3 carbon atoms substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms, or a phenyl group.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, or phenyl.
In one embodiment of the present description, R1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, methyl, isopropyl or phenyl.
In one embodiment of the present specification, at least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms.
In one embodiment of the present description, at least one of R1 and R2 is methyl, ethyl or isopropyl.
In one embodiment of the present description, at least one of R1 and R2 is methyl or isopropyl.
In one embodiment of the present description, at least one of R1 and R2 is methyl.
In one embodiment of the present description, at least one of R2 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, at least one of R2 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, at least one of R2 is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.
In one embodiment of the present specification, at least one of R2 is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms, or a substituted or unsubstituted phenyl group.
In one embodiment of the present specification, at least one of R2 is an alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium.
In one embodiment of the present specification, at least one of R2 is an alkyl group having 1 to 3 carbon atoms or a phenyl group.
In one embodiment of the present description, at least one of R2 is methyl, ethyl, propyl, isopropyl, or phenyl.
In one embodiment of the present description, at least one of R2 is methyl, isopropyl, or phenyl.
In one embodiment of the present description, R1 is hydrogen, deuterium, or methyl, and R2 is hydrogen, deuterium, methyl, isopropyl, or phenyl.
In one embodiment of the present disclosure, R1 is hydrogen or deuterium, and R2 is hydrogen, deuterium, methyl or isopropyl.
In one embodiment of the present description, R1 is hydrogen and R2 is hydrogen, methyl or isopropyl.
In one embodiment of the present description, R1 is hydrogen and R2 is hydrogen or methyl.
In one embodiment of the present description, R1 is hydrogen and R2 is hydrogen or isopropyl.
In one embodiment of the present description, R1 is hydrogen and R2 is methyl or isopropyl.
In one embodiment of the present description, R1 is hydrogen and R2 is methyl.
In one embodiment of the present description, R1 is hydrogen and R2 is isopropyl.
In one embodiment of the present description, R1 is methyl and R2 is hydrogen, deuterium, methyl, isopropyl or phenyl.
In one embodiment of the present description, R1 is methyl and R2 is methyl or isopropyl.
In one embodiment of the present description, R1 is methyl and R2 is phenyl.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group having a valence of 2.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms and having 2 valencies.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, which has 2 valences.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, and having 2 valencies.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, each independently being a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having a valence of O, S or N and having 2 to 60 carbon atoms.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, each independently being a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having a valence of O, S or N and having 2 to 30 carbon atoms.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, each independently being a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having a valence of O, S or N and having 2 to 20 carbon atoms.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently arylene groups having 6 to 30 carbon atoms, which are directly bonded, or substituted or unsubstituted with deuterium or an alkyl group.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently arylene groups having 6 to 30 carbon atoms, which are directly bonded, or substituted or unsubstituted with deuterium or an alkyl group having 1 to 30 carbon atoms.
In an embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted fluorenyl group of 2 valence.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
In an embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium or an alkyl group, or a biphenylene group substituted or unsubstituted with deuterium or an alkyl group.
In an embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium or an alkyl group having 1 to 10 carbon atoms, or a biphenylene group substituted or unsubstituted with deuterium or an alkyl group having 1 to 10 carbon atoms.
In an embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium or an alkyl group having 1 to 3 carbon atoms, or a biphenylene group substituted or unsubstituted with deuterium or an alkyl group having 1 to 3 carbon atoms.
In an embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a directly bonded, or a phenylene group substituted or unsubstituted with deuterium or methyl, a biphenylene group substituted or unsubstituted with deuterium or methyl.
In an embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted with a methyl group, or a biphenylene group substituted or unsubstituted with a methyl group.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted with a methyl group, or a biphenylene group.
In one embodiment of the present specification, L1 to L3 are identical to each other and are directly bonded, or substituted or unsubstituted phenyl groups.
In one embodiment of the present specification, L1 to L3 are identical to each other and are phenyl groups directly bonded, or substituted or unsubstituted with deuterium.
In one embodiment of the present specification, L1 to L3 are identical to each other and are direct bonding or phenyl.
In one embodiment of the present specification, L1 to L3 are identical to each other and are directly bonded.
In one embodiment of the present description, L1 is a direct bond, or a substituted or unsubstituted phenyl group.
In one embodiment of the present description, L1 is a phenyl group directly bonded, or substituted or unsubstituted with deuterium or methyl.
In one embodiment of the present description, L1 is a phenyl group directly bonded, or substituted or unsubstituted with deuterium.
In one embodiment of the present description, L1 is a direct bond or phenyl.
In one embodiment of the present disclosure, L1 is a direct bond.
In one embodiment of the present specification, L2 and L3 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
In one embodiment of the present specification, L2 and L3 are the same or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium or methyl, or a biphenylene group substituted or unsubstituted with deuterium or methyl.
In one embodiment of the present specification, L2 and L3 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
In one embodiment of the present specification, L2 and L3 are the same or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium or an alkyl group, or a biphenylene group substituted or unsubstituted with deuterium or an alkyl group.
In one embodiment of the present specification, L2 and L3 are the same or different from each other, and are each independently a direct bond, a phenylene group substituted or unsubstituted with a methyl group, or a biphenylene group.
In one embodiment of the present description, L2 and L3 are directly bonded.
In one embodiment of the present specification, ar1 and Ar2 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, ar1 and Ar2 are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having O, S or N and having 2 to 60 carbon atoms.
In one embodiment of the present specification, ar1 and Ar2 are the same as or different from each other, and each is independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having O, S or N and having 2 to 30 carbon atoms.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and are each independently an arylene group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms and having 2 to 60 carbon atoms.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and are each independently an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms and having 2 to 30 carbon atoms.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and are each independently an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms and having 2 to 30 carbon atoms.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and are each independently an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms and having 2 to 30 carbon atoms.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and are each independently an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 3 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 3 carbon atoms or an aryl group having 6 to 30 carbon atoms and having 2 to 30 carbon atoms.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and are each independently an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 3 carbon atoms, or an aryl group having 6 to 12 carbon atoms; or a heterocyclic group containing O, S or N which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 3 carbon atoms or an aryl group having 6 to 12 carbon atoms and has 2 to 30 carbon atoms.
In one embodiment of the present specification, ar1 and Ar2 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 naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, each independently being a phenyl group substituted or unsubstituted with deuterium; biphenyl substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; phenanthryl substituted or unsubstituted with deuterium; triphenylene substituted or unsubstituted with deuterium; tetrahydronaphthyl substituted or unsubstituted with 1 or more substituents selected from deuterium, alkyl groups having 1 to 10 carbon atoms, and aryl groups having 6 to 20 carbon atoms; a dibenzofuranyl group substituted or unsubstituted with deuterium; a dibenzothienyl group substituted or unsubstituted with deuterium; or a carbazolyl group substituted or unsubstituted with deuterium.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, each independently being phenyl; a biphenyl group; a terphenyl group; a naphthyl group; phenanthryl; triphenylene; tetrahydronaphthyl substituted or unsubstituted with 1 or more substituents selected from methyl, isopropyl and phenyl; dibenzofuranyl; dibenzothienyl or carbazolyl.
In one embodiment of the present specification, ar1 and Ar2 are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a tetrahydronaphthyl group substituted or unsubstituted with 1 or more substituents of a methyl group and an isopropyl group, a dibenzofuranyl group, a dibenzothienyl group, or a carbazolyl group.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, each independently being a phenyl group substituted or unsubstituted with deuterium; biphenyl substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; phenanthryl substituted or unsubstituted with deuterium; triphenylene substituted or unsubstituted with deuterium; tetrahydronaphthyl substituted or unsubstituted with more than 1 substituent of deuterium, methyl, isopropyl, and phenyl; a dibenzofuranyl group substituted or unsubstituted with deuterium; a dibenzothienyl group substituted or unsubstituted with deuterium; or a carbazolyl group substituted or unsubstituted with deuterium.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, each independently being phenyl; a biphenyl group; a terphenyl group; a naphthyl group; phenanthryl; triphenylene; tetrahydronaphthyl substituted or unsubstituted with 1 or more substituents selected from methyl, isopropyl and phenyl; dibenzofuranyl; dibenzothienyl or carbazolyl.
In one embodiment of the present specification, ar1 and Ar2 are the same as or different from each other, and each is independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a tetrahydronaphthyl group substituted or unsubstituted with 1 or more substituents of a methyl group and an isopropyl group, a dibenzofuranyl group, a dibenzothienyl group, or a carbazolyl group.
In one embodiment of the present specification, a is an integer of 1 to 8.
In one embodiment of the present specification, a is an integer of 1 to 4.
In one embodiment of the present description, a is 8.
In one embodiment of the present description, a is 7.
In one embodiment of the present description, a is 6.
In one embodiment of the present description, a is 5.
In one embodiment of the present description, a is 4.
In one embodiment of the present description, a is 3.
In one embodiment of the present description, a is 2.
In one embodiment of the present description, a is 1.
In one embodiment of the present description, b is an integer from 1 to 3.
In one embodiment of the present description, b is 3.
In one embodiment of the present description, b is 2.
In one embodiment of the present description, b is 1.
In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 1-1.
[ chemical formula 1-1]
In the above-mentioned chemical formula 1-1,
r1, L1 to L3, ar1, ar2 and a are as defined in the above chemical formula 1, and R3 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, R3 is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
In one embodiment of the present specification, R3 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, R3 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, R3 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
In one embodiment of the present specification, R3 is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.
In one embodiment of the present specification, R3 is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms, or a substituted or unsubstituted phenyl group.
In one embodiment of the present specification, R3 is an alkyl group having 1 to 60 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R3 is an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R3 is an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R3 is an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 12 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R3 is an alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 10 carbon atoms substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R3 is an alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium, or a phenyl group substituted or unsubstituted with deuterium.
In one embodiment of the present description, R3 is methyl, ethyl, propyl, isopropyl, or phenyl substituted or unsubstituted with deuterium.
In one embodiment of the present description, R3 is methyl, ethyl, propyl, isopropyl or phenyl.
In one embodiment of the present description, R3 is methyl, isopropyl or phenyl.
In one embodiment of the present description, R3 is methyl or phenyl.
In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-3.
[ chemical formula 2-1]
[ chemical formula 2-2]
[ chemical formulas 2-3]
In the above chemical formulas 2-1 to 2-3,
the definitions of R1, R2, L1 to L3, ar1, ar2, a and b are the same as those in the above chemical formula 1.
In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 2-1, 2-2 and 2-3-1.
[ chemical formula 2-1]
[ chemical formula 2-2]
[ chemical formula 2-3-1]
In the above chemical formulas 2-1, 2-2 and 2-3-1,
the definitions of R1, R2, L1 to L3, ar1, ar2 and a are the same as those in the above chemical formula 1.
In one embodiment of the present specification, the above chemical formula 1 is represented by the following chemical formula 3-1 or 3-2.
[ chemical formula 3-1]
[ chemical formula 3-2]
In the above chemical formulas 3-1 and 3-2,
the definitions of R1, R2, L1 to L3, ar1, ar2, a and b are the same as those in the above chemical formula 1.
In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following compounds.
The compound represented by chemical formula 1 according to an embodiment of the present specification may manufacture a core structure as in the following reaction formula 1. The substituents may be bonded by methods known in the art, and the kinds, positions or numbers of the substituents may be changed according to techniques known in the art.
< reaction No. 1>
In the above reaction formula 1, the definitions of R1 to R2, ar1 to Ar2, L1 to L3, a and b are the same as those in the above chemical formula 1.
In the above reaction formula 1, X may be a halogen group such as Cl, br, I, etc.
In the above reaction formula 1, a process of synthesizing a compound having a specific substituent bonded to a specific position is exemplified, but a compound falling within the range of the above chemical formula 1 may be synthesized by a synthesis method known in the art using a starting material, an intermediate material, or the like known in the art.
In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above chemical formula 1. In addition, in this specification, by introducing various substituents into the core structure of the structure shown above, HOMO and LUMO energy levels of the compound can also be adjusted.
In addition, the present specification provides an organic light emitting device including the above-mentioned compound.
In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.
In the present specification, when a certain component is referred to as "including/comprising" a certain component, unless otherwise specified, it means that other components may be further included, rather than excluded.
The organic light emitting device according to the present specification is characterized by comprising: an anode, a cathode, and 1 or more organic layers provided between the anode and the cathode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic light emitting device of the present specification can be manufactured by a general method and material for manufacturing an organic light emitting device, except that the organic layer is formed by using the compound of chemical formula 1.
The compound may be used not only in the vacuum vapor deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device of the present specification may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including 1 or more of a hole transporting layer, a hole injecting layer, an electron blocking layer, a hole transporting and injecting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and an electron injecting and transporting layer as an organic layer. However, the structure of the organic light emitting device of the present specification is not limited thereto, and may include a smaller or larger number of organic layers.
In the organic light emitting device of the present specification, the organic layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include a compound represented by chemical formula 1 described above.
In the organic light emitting device of the present specification, the organic layer may include a hole transporting layer or a hole injecting layer, and the hole transporting layer or the hole injecting layer may include a compound represented by chemical formula 1.
In one embodiment of the present specification, the organic layer includes an electron blocking layer including a compound represented by chemical formula 1.
In an embodiment of the present specification, the organic layer may include an electron injection layer, an electron transport and injection layer, or a hole blocking layer, and the electron injection layer, the electron transport and injection layer, or the hole blocking layer may include a compound represented by chemical formula 1.
In the organic light emitting device of the present specification, the organic layer may include an electron transporting layer, an electron injecting layer, or an electron transporting and injecting layer, and the electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer may include a compound represented by chemical formula 1 described above.
In one embodiment of the present specification, the organic layer includes an electron modulation layer, and the electron modulation layer may include a compound represented by chemical formula 1.
In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by chemical formula 1.
In the organic light emitting device of the present specification, the organic layer is an electron transporting and injecting layer including the compound represented by chemical formula 1.
In one embodiment of the present specification, the thickness of the organic layer including the compound of formula 1 isTo->Preferably +.>To->More preferably +.>To->
In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1.
In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1 as a main body.
In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1 as a dopant.
In another embodiment, the organic layer may further include other organic compounds, metals, or metal compounds other than the compound represented by chemical formula 1.
In an organic light emitting device according to an embodiment of the present specification, the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. At this time, the dopant in the light emitting layer includes 1 to 50 parts by weight with respect to 100 parts by weight of the host.
As another example, the organic layer includes a light-emitting layer including the compound represented by the chemical formula 1 as a host, and may further include another host.
In one embodiment of the present disclosure, the organic layer includes a light-emitting layer including an anthracene compound.
In one embodiment of the present disclosure, the organic layer includes a light-emitting layer including an anthracene compound as a main body.
In one embodiment of the present disclosure, the organic layer includes a light-emitting layer including an anthracene compound as a host and further including a dopant.
In one embodiment of the present specification, the dopant includes an arylamine compound, a heterocyclic compound including boron and nitrogen, an Ir complex, or the like.
In one embodiment of the present disclosure, the organic layer includes a light-emitting layer including an anthracene compound as a host and an arylamine compound as a dopant.
In an embodiment of the present specification, the organic light emitting device of the present specification may further include 1 or more organic layers among a hole transporting layer, a hole injecting layer, an electron blocking layer, an electron injecting and transporting layer, an electron injecting layer, a hole blocking layer, and a hole transporting and injecting layer.
In an embodiment of the present specification, the organic light emitting device includes: an anode, a cathode, and at least 2 organic layers disposed between the anode and the cathode, wherein at least one of the at least 2 organic layers contains a compound represented by the chemical formula 1.
In one embodiment of the present specification, the organic layer of 2 or more layers may be two or more selected from the group consisting of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, a hole-transporting and injecting layer, and an electron blocking layer.
In one embodiment of the present specification, the 2 or more organic layers may be two or more selected from the group consisting of a light-emitting layer, an electron transporting layer, an electron injecting layer, an electron transporting and injecting layer, an electron adjusting layer, and a hole blocking layer.
In one embodiment of the present specification, the organic layer includes 2 or more electron transport layers, and at least one of the 2 or more electron transport layers includes a compound represented by chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by chemical formula 1 may be contained in 1 layer of the 2 or more electron transport layers, or may be contained in each of the 2 or more electron transport layers.
In addition, in an embodiment of the present specification, when the compound is included in each of the 2 or more electron transport layers, materials other than the compound represented by the chemical formula 1 may be the same as or different from each other.
When the organic layer containing the compound represented by the above chemical formula 1 is an electron transporting layer, an electron injecting layer, or an electron transporting and injecting layer, the electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer may further contain an n-type dopant. The n-type dopant may use materials known in the art, for example, a metal or a metal complex may be used. For example, the electron transport layer including the compound represented by the above chemical formula 1 may further include LiQ (Lithium Quinolate, lithium quinolinolate). According to one example, the compound represented by chemical formula 1 above and the n-type dopant above may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.
According to one example, the compound represented by chemical formula 1 above and the n-type dopant above may be included in a weight ratio of 1:1.
In one embodiment of the present specification, the organic layer includes 2 or more hole transport layers, and at least one of the 2 or more hole transport layers includes a compound represented by chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by chemical formula 1 may be contained in 1 layer of the above-described 2 or more hole transport layers, or may be contained in each of the 2 or more hole transport layers.
In addition, in an embodiment of the present specification, when the compound represented by the above chemical formula 1 is included in each of the 2 or more hole transport layers, materials other than the compound represented by the above chemical formula 1 may be the same or different from each other.
In one embodiment of the present specification, the organic layer may include a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazole group, or a benzocarbazole group, in addition to the organic layer including the compound represented by the chemical formula 1.
In one embodiment of the present specification, the organic light-emitting device may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.
In the organic light emitting device of the present invention, the organic layer may include an electron blocking layer, and the electron blocking layer may use materials known in the art.
For example, the above-described organic light emitting device may have a laminated structure as shown below, but is not limited thereto.
(1) Anode/hole transport layer/light emitting layer/cathode
(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode
(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(10) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(11) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(13) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(14) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(15) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
The structure of the organic light emitting device of the present specification may have the structure shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, an organic layer 10, and a cathode 9 are sequentially stacked. In the structure described above, the above-described compound may be contained in the above-described organic layer 10.
Fig. 2 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 9 are sequentially stacked. In the structure described above, the above-described compound may be contained in the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light emitting layer 6, the hole blocking layer 7, or the electron injection and transport layer 8.
In an embodiment of the present disclosure, the electron blocking layer and the light emitting layer may be disposed adjacent to each other. For example, the electron blocking layer and the light emitting layer may be physically connected to each other.
In an embodiment of the present disclosure, the hole transport layer and the electron blocking layer may be disposed adjacent to each other. For example, the hole transport layer and the electron blocking layer may be physically connected to each other.
The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that 1 or more of the organic layers include the above-described compound, i.e., the compound represented by the above chemical formula 1.
When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present specification may be manufactured as follows: PVD (physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation) is used to vapor deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer is formed on the anode, and then a substance that can function as a cathode is vapor deposited on the organic layer to manufacture the anode. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
The organic layer may further include one or more of a hole transporting layer, a hole injecting layer, an electron blocking layer, an electron injecting and transporting layer, an electron injecting layer, a hole blocking layer, and a hole transporting and injecting layer.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection and transport layer, or the like, but is not limited thereto, and may have a single-layer structure. The organic layer may be formed into a smaller number of layers by a solvent process (solvent process) other than vapor deposition, such as spin coating, dip coating, knife coating, screen printing, ink jet printing, or thermal transfer printing, using various polymer materials.
The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention 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, indium Zinc Oxide); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
The cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that functions to smooth injection of holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can well receive holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers. The thickness of the hole injection layer may be 1 to 150nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the degradation of the hole injection characteristic can be prevented, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the increase of the driving voltage for improving the migration of holes can be prevented.
The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
An electron blocking layer may be disposed between the hole transport layer and the light emitting layer. The above-mentioned compounds or materials known in the art may be used in the above-mentioned electron blocking layer.
The light-emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. As a specific example, there is 8-hydroxy-quinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compoundA material; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
Examples of the host material of the light-emitting layer include an aromatic condensed ring derivative and a heterocyclic compound. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.
When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent substance such as PIQIr (acac) (bi (1-phenylisoquinoline) acetylacetonide), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium), bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) irium, tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin), or Alq may be used 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum, etc., but not limited thereto. When the light emitting layer emits green light, ir (ppy) can be used as a light emitting dopant 3 Phosphorescent substances such as (factris (2-phenylpyridine) iridium, planar tris (2-phenylpyridine) iridium), or Alq 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum), but are not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, (4, 6-F 2 ppy) 2 Irpic or other phosphorescent substance, or spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DS B), distyrylarylene (DSA), PFO-based polymer, PPV-based polymer or other fluorescent substanceThe light substance is not limited thereto.
A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
The electron transport layer can play a role in enabling electron transport to be smooth. The electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high mobility of electrons. As specific examples, there are the above-mentioned compounds or Al complexes of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1 to 50nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the degradation of the electron transport property can be prevented, and when it is 50nm or less, there is an advantage that the increase of the driving voltage for the purpose of improving the electron transfer can be prevented when the thickness of the electron transport layer is too thick.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for 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 has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed generally under the same conditions as those of the hole injection layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
In the following, examples will be given to explain the present specification in detail. However, the embodiments according to the present specification may be modified into various forms, and the scope of the present application is not to be construed as limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully explain the present description to those skilled in the art.
Synthesis example
Synthesis example 1 Synthesis of Compound 1
In N- ([ 1,1' -biphenyl)]-4-yl) -4'- (phenanthren-9-yl) - [1,1' -biphenyl]Toluene (300 ml) was added to 4-amine (20.0 g,40.19 mmol), 6-bromo-7-methyl-1, 2,3, 4-tetrahydronaphthalene (9.23 g,40.99 mmol), and sodium t-butoxide (5.41 g,56.27 mmol), followed by stirring with heating for 10 minutes. To the above mixture was added bis (tri-t-butylphosphine) palladium (0.10 g,0.20 mmol) dissolved in toluene (30 ml), followed by stirring with heating for 1 hour. After completion of the reaction and filtration, the layers were separated with toluene and water. After removal of the solvent, ethyl acetate was used The ester was recrystallized, whereby the above-mentioned compound 1 (20.0 g,77.53% yield) was obtained. (MS [ M+H)] + ＝642)
Synthesis example 2 Synthesis of Compound 2
Using N- (4- (phenanthren-9-yl) phenyl) - [1,1' -biphenyl ]]-4-amine (20.0 g,47.45 mmol) and 6-bromo-1, 4-tetramethyl-7-phenyl-1, 2,3, 4-tetrahydronaphthalene (16.61 g,48.39 mmol), the above compound 2 (25.5 g,78.58% yield) was obtained by the same method as in the above synthesis example 1. (MS [ M+H)] + ＝684)
Synthesis example 3 Synthesis of Compound 3
Using N- (4- (phenanthren-9-yl) phenyl) - [1,1' -biphenyl ]]-4-amine (20.0 g,47.45 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1, 2,3, 4-tetrahydronaphthalene (13.61 g,48.39 mmol), the above compound 3 (23.3 g, 78.96% yield) was obtained by the same method as in the above synthesis example 1. (MS [ M+H)] + ＝622)
Synthesis example 4 Synthesis of Compound 4
Using bis (4- (phenanthren-9-yl) phenyl) amine (20.0 g,38.34 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1, 2,3, 4-tetrahydronaphthalene (11.00 g,39.11 mmol), the above-described compound 4 (22.0 g,79.48% yield) was obtained by the same method as in the above-described synthetic example 1. (MS [ M+H)] + ＝722)
Synthesis example 5 Synthesis of Compound 5
By N-(4- (triphenylen-2-yl) phenyl) - [1,1' -biphenyl ]]-4-amine (20.0 g,42.41 mmol) and 5-bromo-6-methyl-1, 2,3, 4-tetrahydronaphthalene (9.74 g,43.26 mmol), the above compound 5 (20.5 g,78.49% yield) was obtained by the same method as in the above synthesis example 1. (MS [ M+H) ] + ＝616)
Synthesis example 6 Synthesis of Compound 6
Using N- (4- (triphenylen-2-yl) phenyl) - [1,1' -biphenyl ]]-4-amine (20.0 g,42.41 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1, 2,3, 4-tetrahydronaphthalene (12.17 g,43.26 mmol), the above compound 6 (22.5 g,78.96% yield) was obtained by the same method as in the above synthetic example 1. (MS [ M+H)] + ＝672)
Synthesis example 7 Synthesis of Compound 7
Using N- (4- (naphthalen-1-yl) phenyl) - [1,1',4', 1' -terphenyl ]]-4-amine (20.0 g,44.68 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1, 2,3, 4-tetrahydronaphthalene (12.82 g,45.58 mmol), the above compound 7 (22.5 g,77.72% yield) was obtained by the same method as in the above synthesis example 1. (MS [ M+H)] + ＝648)
Synthesis example 8 Synthesis of Compound 8
Using 4- (naphthalen-1-yl) aniline (10.0 g,45.60 mmol) and 6- (4-chlorophenyl) -1,1,4,4,7-pentamethyl-1, 2,3, 4-tetrahydronaphthalene (29.25 g,93.48 mmol), the above-described compound 8 (27.0 g,76.68% yield) was obtained by the same method as in the above-described synthetic example 1. (MS [ M+H)] + ＝772)
Synthesis example 9 Synthesis of Compound 9
By N- ([ 1,1' -biphenyl)]-4-yl) -2'- (9H-carbazol-9-yl) - [1,1' -biphenyl ]]-4-amine (20.0 g,41.10 mmol) and 6- (4-chlorophenyl) -7-methyl-1, 2,3, 4-tetrahydronaphthalene (10.76 g,41.92 mmol), the above-mentioned compound 9 (23.0 g,79.16% yield) was obtained by the same method as in the above-mentioned synthesis example 1. (MS [ M+H) ] + ＝707)
Synthesis example 10 Synthesis of Compound 10
Using N- (2 '- (9H-carbazol-9-yl) - [1,1' -biphenyl ]]-4-yl) - [1.1',4',1 "-terphenyl]-4-amine (20.0 g,35.54 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1, 2,3, 4-tetrahydronaphthalene (10.20 g,36.25 mmol), the above-described compound 10 (21.0 g,77.44% yield) was obtained by the same method as in the above-described synthetic example 1. (MS [ M+H)] + ＝763)
Synthesis example 11 Synthesis of Compound 11
By N- ([ 1,1' -biphenyl)]-4-yl) -2'- (9H-carbazol-9-yl) - [1,1' -biphenyl ]]-4-amine (20.0 g,41.10 mmol) and 6- (4-chlorophenyl) -1,1,4,4,7-pentamethyl-1, 2,3, 4-tetrahydronaphthalene (13.12 g,41.92 mmol), the above-mentioned compound 11 (25.0 g,79.72% yield) was obtained by the same method as in the above-mentioned synthesis example 1. (MS [ M+H)] + ＝763)
Synthesis example 12 Synthesis of Compound 12
By N- ([ 1,1' -biphenyl)]-4-yl) -2'- (9H-carbazol-9-yl) - [1,1' -biphenyl ]]-4-amine (20.0 g,41.10 mmol) and 5- (4-chlorophenyl) -1,1,4,4,6-pentamethyl-1, 2,3, 4-tetrahydronaphthalene (13.12 g,41.92 mmol) of the above compound 12 (24.0 g,76.53% yield) was obtained by the same method as in the above synthetic example 1. (MS [ M+H)] + ＝763)
Synthesis example 13 Synthesis of Compound 13
By N- ([ 1,1' -biphenyl)]-4-yl) -2'- (9H-carbazol-9-yl) - [1,1' -biphenyl ]]-4-amine (20.0 g,41.10 mmol) and 6-bromo-1, 4-tetramethyl-7-phenyl-1, 2,3, 4-tetrahydronaphthalene (14.39 g,41.92 mmol), the above-mentioned compound 13 (24.0 g,77.96% yield) was obtained by the same method as in the above-mentioned synthetic example 1. (MS [ M+H) ] + ＝749)
Synthesis example 14 Synthesis of Compound 14
By N- (4- (dibenzo [ b, d)]Furan-4-yl) phenyl) - [1,1',4',1 "-terphenyl]-4-amine (20.0 g,41.02 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1, 2,3, 4-tetrahydronaphthalene (11.77 g,41.84 mmol), the above-mentioned compound 14 (22.5 g,79.73% yield) was obtained by the same method as in the above-mentioned synthetic example 1. (MS [ M+H)] + ＝688)
Synthesis example 15 Synthesis of Compound 15
Using bis (4- (dibenzo [ b, d)]Furan-4-yl) phenyl) amine (20.0 g,39.87 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1, 2,3, 4-tetrahydronaphthalene (11.44 g,40.67 mmol), the above-mentioned compound 15 (21.5 g,76.83% yield) was obtained by the same method as in the above-mentioned synthetic example 1. (MS [ M+H)] + ＝702)
Synthesis example 16 Synthesis of Compound 16
By N- ([ 1,1' -biphenyl)]-4-yl) -2'- (9H-carbazol-9-yl) - [1,1' -biphenyl ]]-4-amine (20.0 g,41.10 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1, 2,3, 4-tetrahydronaphthalene (11.79 g,41.92 mmol), the above compound 16 (22.5 g,79.69% yield) was obtained by the same method as in the above synthesis example 1. (MS [ M+H)] + ＝687)
< experimental example and comparative experimental example >
Experimental example 1-1
ITO (indium tin oxide) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, a compound represented by the following formula HAT was preparedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, as a hole transport layer, a compound represented by the following chemical formula HT1 is added +.>After vacuum evaporation, the compound 1 produced in synthesis example 1 was treated with +.>Is subjected to thermal vacuum evaporation. Next, as a light-emitting layer, a compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were combined at a weight ratio of 25:1 +.>Vacuum evaporation was performed on the thickness of (c). Next, as a hole blocking layer, a compound represented by the following chemical formula HB1 was used +.>Vacuum evaporation was performed on the thickness of (c). Next, as an electron injection and transport layer, a compound represented by the following chemical formula ET1 and a compound represented by the following LiQ were added at a weight ratio of 1:1 and +.>Is subjected to thermal vacuum evaporation. On the electron transport and injection layer, lithium fluoride (LiF) is added in sequence +.>Is made of aluminum +.>And vapor deposition is performed to form a cathode, thereby manufacturing an organic light-emitting device.
Experimental examples 1-2 to 1-16 and comparative experimental examples 1-1 to 1-3
Organic light-emitting devices of examples 1-2 to 1-16 and comparative examples 1-1 to 1-3 were produced in the same manner as in example 1-1 except that the compound described in table 1 below was used instead of compound 1 in example 1-1. Applying 10mA/cm to the organic light emitting devices manufactured in the experimental example and the comparative experimental example 2 Voltage, efficiency, color coordinates and lifetime were measured at the current of (2), and the junction was measuredThe results are shown in Table 1 below. On the other hand, T95 represents the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
TABLE 1
As shown in table 1 above, it was confirmed that the compound of the present invention is excellent in electron blocking ability, and an organic light emitting device using the compound for an electron blocking layer exhibits remarkable effects in terms of driving voltage, efficiency and lifetime.
Comparing examples 1-1 to 1-16 with comparative examples 1-1 to 1-3, it was confirmed that the compounds of the present invention have low driving voltage, high efficiency and long life in organic light emitting devices using them for electron blocking layers by having an alkyl substituent of 1 to 3 carbon atoms on tetrahydronaphthalene and an alkyl or aryl substituent on the benzene ring moiety of tetrahydronaphthalene.
Experimental examples 2-1 to 2-10 and comparative experimental examples 1-1, 2-1 to 2-4
In the above-described experimental example 1-1, the organic light emitting devices of experimental examples 2-1 to 2-10 and comparative experimental examples 2-1 to 2-4 were fabricated by the same method as the above-described experimental example 1-1 except that the compound represented by the above-described chemical formula EB1 was used instead of the compound 1 as the electron blocking layer and the compound represented by the above-described chemical formula HT1 was used as the hole transporting layer. Applying 10mA/cm to the organic light emitting devices manufactured in the experimental example and the comparative experimental example 2 The voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in table 2 below. On the other hand, T95 represents the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%
TABLE 2
As shown in table 2 above, it was confirmed that the compound of the present invention is excellent in hole transport ability, and an organic light emitting device using the compound for a hole transport layer exhibits remarkable effects in terms of driving voltage, efficiency and lifetime.
Comparing examples 2-1 to 2-10 with comparative examples 1-1 and 2-1 to 2-4, it was confirmed that the compounds of the present invention have low driving voltage, high efficiency and long life for the organic light emitting device for hole transport layer by having alkyl substituent of 1 to 3 carbon atoms on tetrahydronaphthalene and alkyl or aryl substituent on benzene ring moiety of tetrahydronaphthalene.
Claims (14)
1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
r1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
at least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms,
at least one of R2 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
ar1 and Ar2 are the same as or different from each other, each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
l1 to L3 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heterocyclic group having a valence of 2,
a is an integer of 1 to 8, R1 are the same or different from each other when a is 2 or more,
b is an integer of 1 to 3, and when b is 2 or more, R2 are the same or different from each other.
2. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1:
[ chemical formula 1-1]
In the chemical formula 1-1 described above,
r1, L1 to L3, ar1, ar2 and a are as defined in the chemical formula 1,
r3 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
3. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-3:
[ chemical formula 2-1]
[ chemical formula 2-2]
[ chemical formulas 2-3]
In the chemical formulas 2-1 to 2-3,
the definitions of R1, R2, L1 to L3, ar1, ar2, a and b are the same as those in the chemical formula 1.
4. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 3-1 or 3-2:
[ chemical formula 3-1]
[ chemical formula 3-2]
In the chemical formulas 3-1 and 3-2,
the definitions of R1, R2, L1 to L3, ar1, ar2, a and b are the same as those in the chemical formula 1.
5. The compound of claim 1, wherein L1 to L3 are the same or different from each other, each independently being directly bonded, or an arylene group of 6 to 30 carbon atoms substituted or unsubstituted with deuterium or an alkyl group of 1 to 30 carbon atoms.
6. The compound of claim 1, wherein Ar1 and Ar2 are the same or different from each other, each independently being an aryl group of 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group of 1 to 30 carbon atoms, or an aryl group of 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms and having 2 to 30 carbon atoms.
7. The compound of claim 1, wherein L1 to L3 are the same or different from each other, each independently is a direct bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.
8. The compound of claim 1, wherein Ar1 and Ar2 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 naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
9. The compound according to claim 1, wherein R1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
ar1 and Ar2 are the same as or different from each other, and each is independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms and having 2 to 30 carbon atoms,
L1 to L3 are the same or different from each other and are each independently a direct bond; arylene having 6 to 30 carbon atoms substituted or unsubstituted with deuterium or alkyl having 1 to 30 carbon atoms; or a heterocyclic group having a valence of O, S or N and having 2 to 30 carbon atoms, which is substituted or unsubstituted with deuterium.
10. The compound of claim 1, wherein the chemical formula 1 is represented by any one of the following compounds:
11. an organic light emitting device, comprising: an anode, a cathode, and 1 or more organic layers disposed between the anode and the cathode, the 1 or more of the organic layers comprising the compound of any one of claims 1 to 10.
12. The organic light-emitting device of claim 11, wherein the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, the hole injection layer, hole transport layer, or hole injection and transport layer comprising the compound.
13. The organic light-emitting device of claim 11, wherein the organic layer comprises an electron blocking layer comprising the compound.
14. The organic light-emitting device of claim 11, wherein the organic layer further comprises 1 or more of a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron injection and transport layer.
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