CN111560009A - Novel organic compound and organic light emitting diode including the same - Google Patents
Novel organic compound and organic light emitting diode including the same Download PDFInfo
- Publication number
- CN111560009A CN111560009A CN202010467992.4A CN202010467992A CN111560009A CN 111560009 A CN111560009 A CN 111560009A CN 202010467992 A CN202010467992 A CN 202010467992A CN 111560009 A CN111560009 A CN 111560009A
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- light emitting
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 5
- 239000010410 layer Substances 0.000 claims abstract description 55
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- 239000013307 optical fiber Substances 0.000 claims abstract description 5
- 230000005693 optoelectronics Effects 0.000 claims abstract description 5
- 108091008695 photoreceptors Proteins 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
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- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 9
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- 125000004076 pyridyl group Chemical group 0.000 claims description 9
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- 125000005493 quinolyl group Chemical group 0.000 claims description 8
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
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- 150000001923 cyclic compounds Chemical class 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 230000005525 hole transport Effects 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
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- 229910052762 osmium Inorganic materials 0.000 claims description 2
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- 229910052709 silver Inorganic materials 0.000 claims description 2
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000005259 measurement Methods 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
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- 125000001424 substituent group Chemical group 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 11
- 238000000921 elemental analysis Methods 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 3
- 150000001412 amines Chemical group 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
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- 125000003367 polycyclic group Chemical group 0.000 description 3
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
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- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N carbon tetrachloride Substances ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005241 heteroarylamino 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
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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Abstract
The invention belongs to the field of organic light emitting display, and particularly relates to a novel organic compound shown in a formula 1 below and an organic light emitting diode comprising the novel organic compound. The organic light emitting diode includes a substrate, a cathode, an anode, an emission layer including the novel compound, at least one first organic layer, and at least one second organic layer. It also relates to products comprising the light emitting diode and to the use of the light emitting diode in optoelectronics, medicine, biotechnology, optical fibers, lighting devices, electrophotographic photoreceptors, photoelectric converters, organic solar cells, switching elements, organic light emitting field effect transistors, image sensors and dye lasers. The compound of the present invention can realize a lower driving voltage, and the device including the compound of the present invention can have an extended lifetime and excellent luminous efficiency.<Formula 1>
Description
Technical Field
The present invention relates to a novel organic compound and an organic light emitting diode including the same.
Background
Recently, as the size of displays increases, there is an increasing interest in flat display elements that occupy less space. In the art, the technology of organic light emitting displays including Organic Light Emitting Diodes (OLEDs) used as flat display elements has been rapidly developed.
The organic light emitting diode realizes light emission by annihilating pairs of holes and electrons generated by injecting holes and electrons from a hole injection electrode (anode) and an electron injection electrode (cathode) into an emission layer between the anode and the cathode. Advantageously, such organic light emitting diodes may be formed on flexible transparent substrates such as plastic and the like, may be operated at low voltages, consume relatively low power, and have good color reproduction.
Disclosure of Invention
It is an object of the present invention to provide novel compounds that can be used as host materials for emissive layers.
It is another object of the present invention to provide an organic light emitting diode in which an emission layer includes the novel compound to achieve a lower driving voltage, and in which a device includes the novel compound of the present invention, thereby prolonging a lifetime and achieving excellent luminous efficiency.
The object of the present invention is not limited to the above object. Other objects and advantages of the present invention not mentioned above can be understood from the following description, and more clearly understood through embodiments of the present invention. Further, it is easily understood that the objects and advantages of the present invention can be achieved by the features disclosed in the claims and the combinations thereof.
In one aspect, the present invention provides a compound represented by the following formula 1:
< formula 1>
Wherein, X1To X3Each independently is N or CR17Each being the same or different, provided that X1、X2And X3At least one of which is N,
is selected from R1-R6Is selected from R7-R12Is selected from R13-R16And when two or more R are present17Is selected from R17May be combined to form a saturated or unsaturated cyclic compound having a carbon number of 6 to 14,
R1-R6、R7-R12、R13-R16and R17Wherein the moieties not forming a ring are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C2-C30Alkenyl of (a), substituted or unsubstituted C2-C24Alkynyl, substituted or unsubstituted C2-C30With heteroalkyl, substituted or unsubstituted C6-C30Arylalkyl of, substituted or unsubstituted C5-C30Aryl, substituted or unsubstituted C2-C30Heteroaryl, substituted or unsubstituted C3-C30Heteroarylalkyl (heteroaryl), substituted or unsubstituted C3-C30Cycloalkyl, substituted or unsubstituted C3-C20With heterocycloalkyl radical, substituted or unsubstituted C3-C20Cycloalkenyl group of (1), substituted or unsubstituted C3-C30Heteroarylalkyl (heteroaryl), substituted or unsubstituted C1-C20Substituted or unsubstituted arylamino, substituted or unsubstituted alkylamino, substituted or unsubstituted aryloxy, and substituted or unsubstituted alkoxy, with the proviso that all R are excluded1-R12Are each a case selected from one of the group consisting of hydrogen and deuterium.
In one embodiment of the present invention, there is provided an organic light emitting diode comprising a substrate, a cathode, an anode, an Emission Layer (EL) stacked between the cathode and the anode, at least one first organic layer stacked between the cathode and the emission layer, and at least one second organic layer stacked between the emission layer and the anode, wherein the emission layer comprises the compound represented by formula 1 above.
The organic light emitting diode has an organic layer including a novel carbazolyl compound represented by formula 1 above to reduce a driving voltage, prolong a lifetime, and achieve excellent light emitting efficiency.
Detailed Description
Embodiments of the present invention are provided in order to more fully describe the present invention to those skilled in the art. The following embodiments may be modified in various forms. The scope of the present invention is not limited to the following embodiments. These embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the invention to those skilled in the art.
As used herein, the term "halo group" may include fluorine, chlorine, bromine or iodine.
As used herein, the term "alkyl" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, and hexyl.
As used herein, the term "alkenyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon double bonds and having from 2 to 40 carbon atoms. Examples include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
As used herein, the term "alkynyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds and having from 2 to 40 carbon atoms. Examples include, but are not limited to, ethynyl, 2-propynyl, and the like.
As used herein, the term "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having 2 to 60 carbon atoms. Further, such aryl groups may have a form in which two or more rings are simply pendant from each other or fused to each other. Examples of such aryl groups include, but are not limited to, phenyl, naphthyl, phenanthryl, anthracyl, dimethylfluorenyl, and the like.
As used herein, the term "heteroaryl" refers to a monovalent substituent derived from a mono-or poly-heterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. In this connection, at least one carbon, preferably 1 to 3 carbons, in the ring is substituted with a heteroatom, such as N, O, S or Se. Furthermore, such heteroaryl groups can have a form in which two or more rings are simply pendant from each other or fused to an aryl group. Examples of such heteroaryl groups include six-membered monocyclic rings (e.g., pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl), polycyclic rings (e.g., phenoxythienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, 2-pyrimidinyl, and the like). However, the present invention is not limited thereto.
As used herein, the term "aryloxy" refers to a monovalent substituent represented by RO-, wherein R represents an aryl group having 6 to 60 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthoxy, diphenoxy, and the like.
As used herein, the term "alkyloxy" refers to a monovalent substituent represented by R 'O-, wherein R' refers to an alkyl group having 1 to 40 carbon atoms. Such an alkyloxy group has a linear, branched or cyclic structure. Examples of alkyloxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.
As used herein, the term "alkoxy (alkoxy)" refers to a straight, branched, or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited herein, but the alkoxy group preferably has 1 to 20 carbon atoms. Specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy (isopropoxy), isopropoxy (i-propyloxy), n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy.
As used herein, the term "aralkyl" refers to a monovalent group derived from an alkyl group by substituting one or more hydrogen atoms with an aryl group. Preferred aralkyl groups include lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenylethyl and naphthylmethyl. The bond to the parent moiety is through the alkyl group.
As used herein, unless otherwise specified, the term "arylamino" refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.
As used herein, unless otherwise specified, the term "alkylamino" refers to an amine substituted with an alkyl group having 1 to 30 carbon atoms.
As used herein, unless otherwise specified, the term "aralkylaminogroup" refers to an amine substituted with an aryl-alkyl group having from 6 to 30 carbon atoms.
As used herein, unless otherwise specified, the term "heteroarylamino group" refers to an amine group substituted with an aryl group and a heterocyclic group having 6 to 30 carbon atoms.
As used herein, unless otherwise specified, the term "heteroarylalkyl" refers to an aryl-alkyl group substituted with a heterocyclyl group.
As used herein, unless otherwise specified, the term "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantane and the like.
As used herein, unless otherwise specified, the term "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms in which at least one carbon, preferably 1 to 3 carbons, in the ring is substituted with a heteroatom (e.g., N, O, S or Se). Examples of such heterocycloalkyl groups include, but are not limited to, morpholine, piperazine and the like.
As used herein, the term "fused (or condensed) ring" refers to a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.
As used herein, the term "a specific group is bonded to an adjacent group to form a ring (aliphatic groups to an ad jacent group to form a ring)" means that the specific group is bonded to the adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a condensed ring thereof.
As used herein, the term "aliphatic hydrocarbon ring" refers to a ring that is not aromatic and consists only of carbon and hydrogen atoms.
Examples of "aromatic hydrocarbon rings" as used in the present invention include, but are not limited to, phenyl, naphthyl, anthracenyl, and the like.
As used herein, the term "aliphatic heterocyclic ring" refers to an aliphatic ring containing one or more heteroatoms.
As used herein, the term "aromatic heterocyclic ring" refers to an aromatic ring containing one or more heteroatoms.
As used in the present invention, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.
As used herein, the term "substituted" means that a hydrogen atom bonded to a carbon atom in a compound is substituted with another substituent. The position at which the substitution occurs may be a position at which a hydrogen atom is substituted. That is, the position is not limited to a specific position as long as hydrogen at the position can be substituted by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.
As used herein, unless otherwise specified, hydrogen atoms include protium, deuterium, and tritium.
Herein, the substituent substituting for the hydrogen atom may be selected from any one of the group consisting of the following elements: substituted or unsubstituted C1-C20Alkyl (preferably C)1-C6Alkyl), substituted or unsubstituted C1-C20Alkoxy (preferably C)1-C6Alkoxy), halogen, cyano, carboxyl, carbonyl, amino, C1-C20Alkylamino (preferably C)1-C6Alkylamino), nitro, hydrazide, sulfonic acid group, C1-C20Alkylsilyl group (preferably C)1-C6Alkylsilyl) C1-C20Alkoxysilyl radical (Excellent)Is selected as C1-C6Alkoxysilyl group), C3-C30Cycloalkylsilyl (preferably C)3-C7Cycloalkylsilyl group), C5-C30Arylsilyl group (preferably C)6-C14Arylsilyl), unsubstituted or substituted C5-C30Aryl (preferably C)6-C14Aryl group), C4-C30Heteroaryl (preferably C)5-C14Heteroaryl), and combinations thereof, but is not limited thereto.
The present invention relates to a compound represented by the following formula 1:
< formula 1>
Wherein, X1To X3Each independently is N or CR17Each being the same or different, provided that X1、X2And X3At least one of which is N,
is selected from R1-R6Is selected from R7-R12Is selected from R13-R16And when two or more R are present17Is selected from R17May be combined to form a saturated or unsaturated cyclic compound having a carbon number of 6 to 14,
R1-R6、R7-R12、R13-R16and R17Wherein the moieties not forming a ring are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C2-C30Alkenyl of (a), substituted or unsubstituted C2-C24Alkynyl, substituted or unsubstituted C2-C30With heteroalkyl, substituted or unsubstituted C6-C30Arylalkyl of, substituted or unsubstituted C5-C30Aryl, substituted or unsubstituted C2-C30Heteroaryl, substituted or unsubstituted C3-C30Heteroarylalkyl, substituted or unsubstituted C3-C30Cycloalkyl, substituted or unsubstituted C3-C20With heterocycloalkyl radical, substituted or unsubstituted C3-C20Cycloalkenyl group of (1), substituted or unsubstituted C3-C30Heteroarylalkyl, substituted or unsubstituted C1-C20Substituted or unsubstituted arylamino, substituted or unsubstituted alkylamino, substituted or unsubstituted aryloxy, and substituted or unsubstituted alkoxy, with the proviso that all R are excluded1-R12Are each a case selected from one of the group consisting of hydrogen and deuterium.
Specifically, R1-R12Each independently selected from the group consisting of:
in the above-mentioned formula, the compound of formula,
representing a connection (i.e., direct bond) to the remaining structure of formula 1.
In one embodiment, when two or more R are present17When adjacent to R17Combined to form substituted or unsubstituted C6-C10Aryl or C2-C10Fused rings of heteroaryl groups.
In particular, selected from R1-R6Is selected from R7-R12And is selected from R13-R16Are combined to form one of the group consisting of:
and the hydrogen atoms bonded to carbon atoms in the above groups may be substituted or unsubstituted.
In the above-mentioned formula, the compound of formula,
represents a connection (i.e., direct bond) to a carbon atom shared in a fused ring.
Specifically, R1-R17Each independently selected from: substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted methoxy, substituted or unsubstituted ethoxy, substituted or unsubstituted propoxy, substituted or unsubstituted dimethylamino, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylnaphthylamino, and substituted or unsubstituted dinaphthylamino.
In particular, selected from R1-R6Is selected from R7-R12And is selected from R13-R16Are combined to form a fused ring of: a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted piperidyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenylphenyl group, and R not having fused rings joined together1-R6、R7-R12、R13-R16And R17Each independently selected from the group consisting of H, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted piperidyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted anthracenyl, and substituted or unsubstituted phenanthryl.
In one embodiment, formula 1 is represented by formula 1(a) below:
< formula 1(a) >
Wherein R is2-R4
a) Each independently selected from: H. substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted piperidyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted anthracenyl, and substituted or unsubstituted phenanthryl, or
b) And R2-R4The carbon atom to which one of them is bonded and the carbon atom adjacent thereto, together form a fused ring of: a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted piperidyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenylphenyl group. And R2-R4One bonded carbon atom and its adjacent carbon atom in (b) are carbon atoms shared in a condensed ring.
Specifically, R2-R4Each independently selected from: substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted methoxy, substituted or unsubstituted ethoxy, substituted or unsubstituted propoxy, substituted or unsubstituted dimethylamino, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylnaphthylamino, and substituted or unsubstituted dinaphthylamino.
Specifically, the compound of formula 1 may be represented by any of the following structures:
in another embodiment of the present invention, there is provided an organic light emitting diode including a substrate, a cathode, an anode, an Emission Layer (EL) stacked between the cathode and the anode, at least one first organic layer stacked between the cathode and the emission layer, and at least one second organic layer stacked between the emission layer and the anode, wherein the emission layer includes the above-described compound according to one embodiment of the present invention.
The emission layer includes a compound represented by the following formula 1:
< formula 1>
Wherein, X1To X3Each independently is N or CR17Each being the same or different, provided that X1、X2And X3At least one of which is N,
is selected from R1-R6Is selected from R7-R12Is selected from R13-R16And when two or more R are present17Is selected from R17May be combined to form a saturated or unsaturated cyclic compound having a carbon number of 6 to 14,
R1-R6、R7-R12、R13-R16and R17Wherein the moieties not forming a ring are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C2-C30Alkenyl of (a), substituted or unsubstituted C2-C24Alkynyl, substituted or notSubstituted C2-C30With heteroalkyl, substituted or unsubstituted C6-C30Arylalkyl of, substituted or unsubstituted C5-C30Aryl, substituted or unsubstituted C2-C30Heteroaryl, substituted or unsubstituted C3-C30Heteroarylalkyl, substituted or unsubstituted C3-C30Cycloalkyl, substituted or unsubstituted C3-C20With heterocycloalkyl radical, substituted or unsubstituted C3-C20Cycloalkenyl group of (1), substituted or unsubstituted C3-C30Heteroarylalkyl, substituted or unsubstituted C1-C20Substituted or unsubstituted arylamino, substituted or unsubstituted alkylamino, substituted or unsubstituted aryloxy, and substituted or unsubstituted alkoxy, with the proviso that all R are excluded1-R12Are each a case selected from one of the group consisting of hydrogen and deuterium.
The compounds represented by formula 1 are described in detail above.
In particular, the at least one first organic layer is selected from: an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), a Hole Blocking Layer (HBL), and a Buffer Layer (BL).
In particular, the at least one second organic layer is selected from: a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), and a Buffer Layer (BL).
The materials of the Hole Injection Layer (HIL), the Hole Transport Layer (HTL), the Electron Blocking Layer (EBL), the Buffer Layer (BL), the Electron Injection Layer (EIL), the Electron Transport Layer (ETL), the Hole Blocking Layer (HBL), and the Buffer Layer (BL) are known materials having such functions, respectively.
In one embodiment, the emissive layer further comprises a dopant. The material of the dopant is a known material having a dopant function. For example, the dopant can be a metal complex comprising Ir, Pt, Ni, Au, Os, Re, Rh, Zn, Ag, Fe, or W.
In one embodiment, the emission layer further includes another host material other than the compound represented by formula 1. The material for another host material is a known material having a function of a host material, for example, a red host material, a blue host material, a yellow host material, or the like.
In one embodiment, the emission layer includes a dopant and a compound represented by formula 1 as a host. The emission of an Organic Light Emitting Diode (OLED) device is caused by charge recombination at an Emission Layer (EL) therein. When the electrons and holes meet in the desired region, high-energy excitons of the host material are formed. Thus, energy is transferred to the dopant material and causes the desired emission.
The compound of formula 1 above the emissive layer can reduce the HOMO energy gap with the dopant material. The compound represented by formula 1 also has a greater singlet and triplet energy than the dopant material in the emissive layer. A smaller bandgap energy may result in a lower operating voltage compared to the reference material.
In one embodiment, at least two of the organic light emitting diodes according to one embodiment of the present invention are stacked to form a series structure.
In another embodiment of the present invention, there is provided a product including an organic light emitting diode according to an embodiment of the present invention.
In another embodiment of the present invention, there is provided a use of the organic light emitting diode according to one embodiment of the present invention in optoelectronics, medicine, biotechnology, optical fiber, lighting device, electrophotographic photoreceptor, photoelectric converter, organic solar cell, switching element, organic light emitting field effect transistor, image sensor, and dye laser.
In another embodiment of the invention, there is provided a use of the product of one embodiment of the invention in optoelectronics, medicine, biotechnology, optical fiber, lighting device, electrophotographic photoreceptor, photoelectric converter, organic solar cell, switching element, organic light-emitting field-effect transistor, image sensor, and dye laser.
Hereinafter, examples and comparative examples are explained. The embodiments are merely examples of the invention. Therefore, the present invention is not limited to these examples.
(examples)
Compounds were synthesized as follows according to examples and comparative examples. In the examples, the following compounds 1-1, 1-2 and 1-3 were prepared.
Synthesis of Compound 1-1:
< reaction formula 1>
Compound S2
Into a 2500ml two-necked flask, N was introduced2S1(14.319g, 1.0 equiv (eq.)), 2, 3-diboronaphthalene (30.026g, 1.05 equiv.), Pd2(dba)3(2.747g，3mol％)、P(t-Bu)3(3 mol% in toluene, 33.333ml, 1 mol%) and Na (O-t-Bu) (50.890g, 2.1 eq.) in toluene (1000ml) were refluxed for 8 hours. After cooling to room temperature, H was added2O (300ml) and stirred for a further 30 minutes then the reaction mixture was extracted with ethyl acetate (3 × 200ml) the organic layers were collected successively over MgSO4Dried, filtered and concentrated to dryness. The crude product was purified by flash column chromatography (ethyl acetate/hexane, 1/15) to afford S2(32.735g, 94%).
C20H14Elemental analysis of BrN:
calculated values: c, 68.98; h, 4.05; n, 4.02; measurement values: c, 68.94; h, 4.03; n, 4.04
C20H14HRMS (EI) M/z (M) for BrN+)：
Calculated values: 347.0310, respectively; measurement values: 347.0302
Compound S3
Into a 1000ml two-necked flask was added N2A solution of S2(27.859g, 1.0 eq.) and triethylphosphine (28.361g, 3.0 eq.) in 1, 2-dichlorobenzene (500ml) was stirred at 185 ℃ for 30 hours. After cooling to room temperature, H was added2O(300ml) and stirred for a further 30 minutes then the reaction mixture was extracted with ethyl acetate (3 × 200ml) the organic layers were collected successively over MgSO4Dried, filtered and concentrated to dryness. The crude product was purified by flash column chromatography (ethyl acetate/hexane, 1/30) to afford S3(16.472g, 77%).
C20H13Elemental analysis of N:
calculated values: c, 89.86; h, 4.90; n, 5.24; measurement values: c, 89.87; h, 4.88; n, 5.25
C20H13HRMS (EI) M/z (M) of N+)：
Calculated values: 267.1048, respectively; measurement values: 267.1041
Compound S4
Into a 500ml three-necked flask, N was introduced2S3(13.370g, 1.0 equiv.) solution and CCl4CuBr (8.609g, 1.2 eq.) in (250ml) was refluxed for 24 hours. After cooling to room temperature, H was added2O (150ml) and stirred for a further 30 minutes then the reaction mixture was extracted with ethyl acetate (3 × 100ml) the organic layers were collected successively over MgSO4Dried, filtered and concentrated to dryness. The crude product was purified by flash column chromatography (ethyl acetate/hexane, 1/25) to afford S4(11.252g, 65%).
C20H12Elemental analysis of BrN:
calculated values: c, 69.38; h, 3.49; n, 4.05; measurement values: c, 69.36; h, 3.48; n, 4.07
C20H12HRMS (EI) M/z (M) for BrN+)：
Calculated values: 345.0153, respectively; measurement values: 345.0159
Compound S5a-c
Into a 100ml two-necked flask was added N2A solution of S4(3.462g, 1.0 eq.), the corresponding boric acid (12mmol, 1.2 eq.), Pd (PPh)3)4(0.578g, 5 mol%) and toluene/H2Na in O (100/10ml)2CO3(2.650g, 2.5 eq.) and refluxed for 19 hours. After cooling to room temperature, H was added2O (30ml) and stirred for a further 30 minutes. The reaction mixture was then washed with ethyl acetate(3 × 20ml) the organic layer was collected in order and extracted over MgSO4Dried, filtered and concentrated to dryness. The crude product was purified by flash column chromatography (ethyl acetate/hexanes, 1/20) to afford S5 a-c.
5a(3.160g，92％)：
C26H17Elemental analysis of N:
calculated values: c, 90.93; h, 4.99; n, 4.08; measurement values: c, 90.90; h, 4.99; n, 4.10
C40H25N3HRMS (EI) M/z (M)+)：
Calculated values: 343.1361, respectively; measurement values: 343.1367
5b(3.541g，90％)：
C30H19Elemental analysis of N:
calculated values: c, 91.57; h, 4.87; n, 3.56; measurement values: c, 91.54; h, 4.86; n, 3.60
C44H27N3HRMS (EI) M/z (M)+)：
Calculated values: 393.1517, respectively; measurement values: 393.1511
5c(3.384g，86％)：
C30H19Elemental analysis of N:
calculated values: c, 91.57; h, 4.87; n, 3.56; measurement values: c, 91.54; h, 4.86; n, 3.60
C44H27N3HRMS (EI) M/z (M)+)：
Calculated values: 393.1517, respectively; measurement values: 393.1514
Compounds 1-1 to 1-3
Into a 100ml two-necked flask was added N2S5a-c (5mmol, 1.0 equiv.), I1(1.264g, 1.05 equiv.), Pd2(dba)3(0.137g，3mol％)、P(t-Bu)3(3 mol% in toluene, 0.167ml, 1 mol%) and Na (O-t-Bu) (2.545g, 2.1 eq.) in toluene (50ml) were refluxed for 8 hours. After cooling to room temperature, H was added2O (30ml) and stirred for a further 30 minutes then the reaction mixture was extracted with ethyl acetate (3 × 20ml). The organic layers were collected in sequence over MgSO4Dried, filtered and concentrated to dryness. The crude product was purified by flash column chromatography (ethyl acetate/hexane, 1/25) to afford 1-1 to 1-3.
1-1(2.300g，84％)：
C40H25N3Elemental analysis of (2):
calculated values: c, 87.73; h, 4.60; n, 7.67; measurement values: c, 87.74; h, 4.58; n, 7.68
C40H25N3HRMS (EI) M/z (M)+)：
Calculated values: 547.2048, respectively; measurement values: 547.2042
1-2(2.361g，79％)：
C44H27N3Elemental analysis of (2):
calculated values: c, 88.42; h, 4.55; n, 7.03; measurement values: c, 88.40; h, 4.54; n, 7.06
C44H27N3HRMS (EI) M/z (M)+)：
Calculated values: 597.2205, respectively; measurement values: 597.2211
1-3(2.122g，71％)：
C44H27N3Elemental analysis of (2):
calculated values: c, 88.42; h, 4.55; n, 7.03; measurement values: c, 88.43; h, 4.54; n, 7.03
C44H27N3HRMS (EI) M/z (M)+)：
Calculated values: 597.2205, respectively; measurement values: 597.2201
(evaluation)
Thoroughly cleaning patterned Indium Tin Oxide (ITO) coated glass substrates (NHT, 2mm x 2mm, 20. omega. cm)-2) And oxygen plasma (150W, 5min, 4X 10)-2torr) processing. Prior to the device experiments, the organic material was purified by thermal sublimation. In a multi-source thermal evaporation system, at 3X10-6Preparing the organic light emitting diode under the base pressure of torr or below. Deposition rate of organic materials controlled by dopant (Inficone IC/5)A rate of
It is excluded that the dopant is co-evaporated at a suitable rate to obtain the desired doping level. All organic light emitting diodes are characterized by using a light source unit (Keithley2400) and a spectrometer (Photo research pr 650).
Red organic light emitting diodes are made by high vacuum thermal evaporation of organic light emitting diode material onto ITO coated glass used as the anode.
For the red device, first, 60nm thick 4,4' -bis [ N- {4- (N, N-di-m-tolylamino) phenyl } -N-phenylamino ] was deposited]A biphenyl (DNTPD) hole injection layer, followed by deposition of a 30nm thick layer of 4,4' -bis [ N- (1-naphthyl) -N-phenylamino]Biphenyl (NPB) acts as a Hole Transport Layer (HTL). Secondly, by co-depositing 5 wt% of (piq) as a dopant2Ir (acac) and a bipolar material as a red host form an Emission Layer (EL) 30nm thick. Finally, an Electron Transport Layer (ETL) of 35nm thickness was formed, containing 2- (4- (9, 10-bis (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d]Imidazole (ET 1). LiF (0.5nm) and Al (100nm) as electron injection promoting layer and cathode, respectively
Reference example 1
Ref 1 shown below is used as a red host material with the above-described device architecture.
Reference example 2
Ref 2 shown below is used as the red host material with the device architecture described above.
Reference example 3
Ref 3 shown below is used as the red host material with the device architecture described above.
Example 1
Compound 1-1 was used as the red host material with the device architecture described above.
Example 2
Compound 1-2 was used as the red host material with the device architecture described above.
Example 3
Compounds 1-3 were used as red host materials with the device architecture described above.
When we apply 10mA/cm2The properties of the material when loaded into the apparatus are shown in table 1 below.
[ Table 1]
| Red body | Voltage regulator | Cd/A | lm/W | CIE x | CIE y | |
| Reference example 1 | Ref 1 | 4.7 | 13 | 8.68 | 0.668 | 0.326 |
| Reference example 2 | Ref 2 | 4.6 | 10 | 6.82 | 0.670 | 0.324 |
| Reference example 3 | Ref 3 | 4.9 | 9 | 5.76 | 0.665 | 0.329 |
| Example 1 | Compound 1-1 | 4.5 | 15 | 10.46 | 0.668 | 0.327 |
| Example 2 | Compound 1-2 | 4.6 | 16 | 10.92 | 0.667 | 0.326 |
| Example 3 | Compounds 1 to 3 | 4.5 | 18 | 12.56 | 0.669 | 0.328 |
Embodiments of the present invention have been described in order to enable any person skilled in the art to make or use the invention. Various modifications to these embodiments will be readily apparent to those skilled in the art. The general principles defined by the present invention may be applied to other embodiments without departing from the scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (18)
1. A compound represented by the following formula 1:
< formula 1>
Wherein, X1To X3Each independently is N or CR17Each being the same or different, provided that X1、X2And X3At least one of which is N,
is selected from R1-R6Is selected from R7-R12Is selected from R13-R16And when two or more R are present17Is selected from R17May be combined to form a saturated or unsaturated cyclic compound having a carbon number of 6 to 14,
R1-R6、R7-R12、R13-R16and R17Wherein each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C2-C30Alkenyl of (a), substituted or unsubstituted C2-C24Alkynyl, substituted or unsubstitutedSubstituted C2-C30With heteroalkyl, substituted or unsubstituted C6-C30Arylalkyl of, substituted or unsubstituted C5-C30Aryl, substituted or unsubstituted C2-C30Heteroaryl, substituted or unsubstituted C3-C30Heteroarylalkyl, substituted or unsubstituted C3-C30Cycloalkyl, substituted or unsubstituted C3-C20With heterocycloalkyl radical, substituted or unsubstituted C3-C20Cycloalkenyl group of (1), substituted or unsubstituted C3-C30Heteroarylalkyl, substituted or unsubstituted C1-C20Substituted or unsubstituted arylamino, substituted or unsubstituted alkylamino, substituted or unsubstituted aryloxy, and substituted or unsubstituted alkoxy, with the proviso that all R are excluded1-R12Are each a case selected from one of the group consisting of hydrogen and deuterium.
2. The compound of claim 1, wherein R1-R12Each independently selected from the group consisting of:
3. the compound of claim 1, wherein when two or more R's are present17When adjacent to R17Combined to form substituted or unsubstituted C6-C10Aryl or C2-C10Fused rings of heteroaryl groups.
4. The compound of claim 1, wherein the is selected from R1-R6Said is selected from R7-R12And said is selected from R13-R16Are combined to form one of the group consisting of:
The hydrogen atoms bonded to carbon atoms in the above groups may be substituted or unsubstituted.
5. The compound of claim 1, wherein R1-R17Each independently selected from: substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted methoxy, substituted or unsubstituted ethoxy, substituted or unsubstituted propoxy, substituted or unsubstituted dimethylamino, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylnaphthylamino, and substituted or unsubstituted dinaphthylamino.
6. The compound of claim 1, wherein the is selected from R1-R6Said is selected from R7-R12And said is selected from R13-R16Are combined to form a fused ring of: a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted piperidyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenylphenyl group,
R1-R6、R7-R12、R13-R16and R17Each independently selected from the group consisting of H, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinaA quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted anthracenyl group, and a substituted or unsubstituted phenanthryl group.
7. The compound according to claim 1, wherein formula 1 is represented by the following formula 1 (a):
< formula 1(a) >
Wherein R is2-R4
a) Each independently selected from: H. substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted piperidyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted anthracenyl, and substituted or unsubstituted phenanthryl, or
b) And R2-R4The carbon atom to which one is bonded and the carbon atom adjacent thereto, together form a fused ring of: a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted piperidyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenylphenyl group.
8. The compound of claim 7, wherein R2-R4Each independently selected from:
c) substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted methoxy, substituted or unsubstituted ethoxy, substituted or unsubstituted propoxy, substituted or unsubstituted dimethylamino, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylnaphthylamino, and substituted or unsubstituted dinaphthylamino.
9. The compound of claim 1, wherein the compound of formula 1 is selected from compounds represented by the following structures:
10. an organic light emitting diode comprising a substrate, a cathode, an anode, an Emission Layer (EL) stacked between the cathode and the anode, at least one first organic layer stacked between the cathode and the emission layer, and at least one second organic layer stacked between the emission layer and the anode,
wherein the emissive layer comprises a compound according to any one of claims 1-9.
11. An organic light emitting diode according to claim 10 wherein the at least one first organic layer is selected from: an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), a Hole Blocking Layer (HBL) and a Buffer Layer (BL), and
the at least one second organic layer is selected from: a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), and a Buffer Layer (BL).
12. The organic light emitting diode of claim 10, wherein the emissive layer further comprises a doping material.
13. The organic light-emitting diode of claim 12, wherein the doping material is a metal complex comprising Ir, Pt, Ni, Au, Os, Re, Rh, Zn, Ag, Fe, or W.
14. The organic light-emitting diode of claim 10, wherein the emissive layer further comprises another host material.
15. An organic light emitting diode wherein at least two of the organic light emitting diodes according to claim 10 are stacked to form a series structure.
16. A product comprising the organic light emitting diode of claim 10.
17. Use of the organic light emitting diode according to claim 10 in optoelectronics, medicine, biotechnology, optical fiber, lighting device, electrophotographic photoreceptor, photoelectric converter, organic solar cell, switching element, organic light emitting field effect transistor, image sensor, and dye laser.
18. Use of the product according to claim 16 in optoelectronics, medicine, biotechnology, optical fibers, lighting devices, electrophotographic photoreceptors, photoelectric converters, organic solar cells, switching elements, organic light emitting field effect transistors, image sensors, and dye lasers.
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| CN115925703A (en) * | 2023-01-03 | 2023-04-07 | 烟台九目化学股份有限公司 | Benzoindole benzoquinoline structure compound, preparation method and OLED device |
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| CN115925703B (en) * | 2023-01-03 | 2023-12-01 | 烟台九目化学股份有限公司 | Benzoindolebenzoquinoline structural compound, preparation method and OLED device |
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