KR101449227B1 - 유기 발광 소자 - Google Patents
유기 발광 소자 Download PDFInfo
- Publication number
- KR101449227B1 KR101449227B1 KR1020127030127A KR20127030127A KR101449227B1 KR 101449227 B1 KR101449227 B1 KR 101449227B1 KR 1020127030127 A KR1020127030127 A KR 1020127030127A KR 20127030127 A KR20127030127 A KR 20127030127A KR 101449227 B1 KR101449227 B1 KR 101449227B1
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- KR
- South Korea
- Prior art keywords
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- substituted
- light emitting
- unsubstituted
- compound
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- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims abstract description 64
- 239000000463 material Substances 0.000 claims description 106
- -1 xanthone compound Chemical class 0.000 claims description 78
- 150000002894 organic compounds Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 239000010410 layer Substances 0.000 description 139
- 150000001875 compounds Chemical class 0.000 description 76
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 16
- 230000032258 transport Effects 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
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- 238000003786 synthesis reaction Methods 0.000 description 14
- 229940125904 compound 1 Drugs 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 150000007964 xanthones Chemical class 0.000 description 12
- 230000000903 blocking effect Effects 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 101000687716 Drosophila melanogaster SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 homolog Proteins 0.000 description 9
- 101000687741 Mus musculus SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 Proteins 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- QFFGPRCMQTXBTH-UHFFFAOYSA-N 2-[5-tert-butyl-2-(4-tert-butylphenyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(C(C)(C)C)C=C1B1OC(C)(C)C(C)(C)O1 QFFGPRCMQTXBTH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 238000004020 luminiscence type Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 0 *c(cc1Oc2ccccc22)ccc1C2=O Chemical compound *c(cc1Oc2ccccc22)ccc1C2=O 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000000059 patterning Methods 0.000 description 3
- 238000001296 phosphorescence spectrum Methods 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 125000005580 triphenylene group Chemical group 0.000 description 3
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FOQJHZPURACERJ-UHFFFAOYSA-N CB1OC(C)(C)C(C)(C)O1 Chemical compound CB1OC(C)(C)C(C)(C)O1 FOQJHZPURACERJ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XCJHDJAODLKGLG-UHFFFAOYSA-N Oc(cc1Oc2c3cccc2)ccc1C3=O Chemical compound Oc(cc1Oc2c3cccc2)ccc1C3=O XCJHDJAODLKGLG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000004050 hot filament vapor deposition Methods 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000004776 molecular orbital Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000002161 passivation Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- 239000004332 silver Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 description 1
- MRBZYVMZUBUDAX-UHFFFAOYSA-N (3,5-diphenylphenyl)boronic acid Chemical compound C=1C(B(O)O)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 MRBZYVMZUBUDAX-UHFFFAOYSA-N 0.000 description 1
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
- ATZAUOICJHZAFI-UHFFFAOYSA-N 1-(2-phenylphenyl)dibenzofuran Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC2=C1C1=CC=CC=C1O2 ATZAUOICJHZAFI-UHFFFAOYSA-N 0.000 description 1
- MXVLMYZRJAHEIS-UHFFFAOYSA-N 1-(2-phenylphenyl)naphthalene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 MXVLMYZRJAHEIS-UHFFFAOYSA-N 0.000 description 1
- FJGCHSOBUSYEGR-UHFFFAOYSA-N 1-(2-phenylphenyl)triphenylene Chemical group c1ccc(cc1)-c1ccccc1-c1cccc2c3ccccc3c3ccccc3c12 FJGCHSOBUSYEGR-UHFFFAOYSA-N 0.000 description 1
- CDKCEZNPAYWORX-UHFFFAOYSA-N 1-tert-butyl-4-(4-tert-butylphenyl)benzene Chemical group C1=CC(C(C)(C)C)=CC=C1C1=CC=C(C(C)(C)C)C=C1 CDKCEZNPAYWORX-UHFFFAOYSA-N 0.000 description 1
- HISQGSPPFXDPLK-UHFFFAOYSA-N 2-(9,9-dimethylfluoren-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 HISQGSPPFXDPLK-UHFFFAOYSA-N 0.000 description 1
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
- YREWNAIHDLIYMI-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-phenanthren-9-yl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC2=CC=CC=C2C2=CC=CC=C12 YREWNAIHDLIYMI-UHFFFAOYSA-N 0.000 description 1
- VXLBBSLCTFTKOE-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-triphenylen-2-yl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C(=CC=CC=2)C=2C3=CC=CC=2)C3=C1 VXLBBSLCTFTKOE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical class C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- QXLPTKBEKXPBRC-UHFFFAOYSA-N CC(C)(C)c(cc1)cc(Oc2cc(C(C)(C)C)ccc22)c1C2=O Chemical compound CC(C)(C)c(cc1)cc(Oc2cc(C(C)(C)C)ccc22)c1C2=O QXLPTKBEKXPBRC-UHFFFAOYSA-N 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C Chemical compound CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- NUEQZABYJDKUTI-UHFFFAOYSA-N CC1(C)OB(c2cc(-c3cccc(-c4cccc5c4[s]c4ccccc54)c3)ccc2)OC1(C)C Chemical compound CC1(C)OB(c2cc(-c3cccc(-c4cccc5c4[s]c4ccccc54)c3)ccc2)OC1(C)C NUEQZABYJDKUTI-UHFFFAOYSA-N 0.000 description 1
- GEZUSWQDBBINQD-UHFFFAOYSA-N CC1(C)c2cc(-c(cc3)cc(Oc4c5ccc(-c6ccc7-c8ccccc8C(C)(C)c7c6)c4)c3C5=O)ccc2-c2c1cccc2 Chemical compound CC1(C)c2cc(-c(cc3)cc(Oc4c5ccc(-c6ccc7-c8ccccc8C(C)(C)c7c6)c4)c3C5=O)ccc2-c2c1cccc2 GEZUSWQDBBINQD-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- 238000003775 Density Functional Theory Methods 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N Nc(cc1)ccc1-c1ccccc1 Chemical compound Nc(cc1)ccc1-c1ccccc1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- WJRLNYUGAABWDI-UHFFFAOYSA-N O=C(c1c2)c(cc(cc3)-c4ccc5-c6ccccc6C6(c7ccccc7-c7ccccc67)c5c4)c3Oc1ccc2-c1ccc2-c3ccccc3C3(c4ccccc4-c4ccccc34)c2c1 Chemical compound O=C(c1c2)c(cc(cc3)-c4ccc5-c6ccccc6C6(c7ccccc7-c7ccccc67)c5c4)c3Oc1ccc2-c1ccc2-c3ccccc3C3(c4ccccc4-c4ccccc34)c2c1 WJRLNYUGAABWDI-UHFFFAOYSA-N 0.000 description 1
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| PCT/JP2011/060008 WO2011136156A1 (en) | 2010-04-26 | 2011-04-19 | Organic light-emitting device |
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| JP5677036B2 (ja) | 2010-11-08 | 2015-02-25 | キヤノン株式会社 | 有機発光素子 |
| JP5760217B2 (ja) * | 2011-08-02 | 2015-08-05 | キヤノン株式会社 | 有機金属錯体及びこれを用いた有機発光素子 |
| JP6157125B2 (ja) | 2013-01-22 | 2017-07-05 | キヤノン株式会社 | イリジウム錯体およびそれを有する有機発光素子 |
| JP6271154B2 (ja) * | 2013-05-10 | 2018-01-31 | 住友化学株式会社 | 発光素子 |
| WO2015002213A1 (ja) * | 2013-07-03 | 2015-01-08 | 国立大学法人九州大学 | 発光材料、遅延蛍光体、有機発光素子および化合物 |
| US20160164002A1 (en) * | 2013-07-30 | 2016-06-09 | Merck Patent Gmbh | Materials for electronic devices |
| CN105408448B (zh) | 2013-07-30 | 2018-11-02 | 默克专利有限公司 | 用于电子器件的材料 |
| WO2015071473A1 (en) * | 2013-11-17 | 2015-05-21 | Solvay Sa | Multilayer structure with sbf matrix materials in adjacent layers |
| US10355227B2 (en) | 2013-12-16 | 2019-07-16 | Universal Display Corporation | Metal complex for phosphorescent OLED |
| KR101764002B1 (ko) * | 2014-05-22 | 2017-08-02 | 주식회사 엘지화학 | 헤테로환 화합물 및 이를 포함하는 유기발광소자 |
| CN104725343B (zh) * | 2015-01-19 | 2017-03-22 | 甘肃天元农业科技有限公司 | 一种呫吨酮化合物及其制备方法和应用 |
| CN106892944A (zh) * | 2015-12-17 | 2017-06-27 | 上海和辉光电有限公司 | 一种吡啶联嘧啶的铱配合物 |
| CN107068876B (zh) * | 2016-04-25 | 2018-12-28 | 中节能万润股份有限公司 | 一种基于10,10-二芳基蒽酮化合物的有机电致发光器件及其应用 |
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| EP3618578B1 (en) * | 2017-04-27 | 2023-09-06 | Sumitomo Chemical Company, Limited | Composition and light-emitting element using same |
| CN109748916B (zh) * | 2017-11-03 | 2021-06-15 | 中节能万润股份有限公司 | 一种以氮杂螺芴和芳基酮为核心的化合物、其制备方法及其在oled上的应用 |
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| CN111200067B (zh) * | 2018-11-20 | 2022-08-02 | 江苏三月科技股份有限公司 | 有机电致发光器件、其制备方法及包含其的显示装置 |
| CN112010843B (zh) * | 2019-05-30 | 2022-03-08 | 烟台显华光电材料研究院有限公司 | 一类用于制备有机光电器件的化合物及其应用 |
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| CN111253393B (zh) * | 2020-02-05 | 2022-01-25 | 北京大学 | 长寿命三线态激子限域材料及其在oled器件中的应用 |
| JP7665313B2 (ja) * | 2020-11-02 | 2025-04-21 | キヤノン株式会社 | 有機化合物及び有機発光素子 |
| JP2023015701A (ja) * | 2021-07-20 | 2023-02-01 | キヤノン株式会社 | 有機発光素子及び有機化合物 |
| JP2023019417A (ja) * | 2021-07-29 | 2023-02-09 | キヤノン株式会社 | 有機発光素子、表示装置、光電変換装置、電子機器、照明装置、移動体、および、露光光源 |
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|---|---|
| CN102870248A (zh) | 2013-01-09 |
| EP2564441B1 (en) | 2019-03-06 |
| JP2011249754A (ja) | 2011-12-08 |
| EP2564441A4 (en) | 2017-12-27 |
| WO2011136156A1 (en) | 2011-11-03 |
| JP5618753B2 (ja) | 2014-11-05 |
| CN102870248B (zh) | 2015-07-29 |
| US20130037791A1 (en) | 2013-02-14 |
| US9269911B2 (en) | 2016-02-23 |
| KR20130010015A (ko) | 2013-01-24 |
| EP2564441A1 (en) | 2013-03-06 |
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