KR20230171384A - Novel organic compounds and an organic electroluminescent device comprising the same - Google Patents
Novel organic compounds and an organic electroluminescent device comprising the same Download PDFInfo
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- KR20230171384A KR20230171384A KR1020230071975A KR20230071975A KR20230171384A KR 20230171384 A KR20230171384 A KR 20230171384A KR 1020230071975 A KR1020230071975 A KR 1020230071975A KR 20230071975 A KR20230071975 A KR 20230071975A KR 20230171384 A KR20230171384 A KR 20230171384A
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- South Korea
- Prior art keywords
- group
- carbon atoms
- phenyl
- substituted
- pyrenyl
- Prior art date
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 148
- -1 9,9-dimethylfluorenyl Chemical group 0.000 claims description 114
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 72
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 54
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 54
- 125000001725 pyrenyl group Chemical group 0.000 claims description 54
- 125000005580 triphenylene group Chemical group 0.000 claims description 54
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000004001 thioalkyl group Chemical group 0.000 claims description 36
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 35
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 34
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 30
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 229910052805 deuterium Inorganic materials 0.000 claims description 30
- 229910052710 silicon Inorganic materials 0.000 claims description 30
- 229910052722 tritium Inorganic materials 0.000 claims description 30
- 239000004305 biphenyl Substances 0.000 claims description 28
- 235000010290 biphenyl Nutrition 0.000 claims description 27
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 27
- 125000001624 naphthyl group Chemical group 0.000 claims description 27
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 27
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 27
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 27
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 24
- 150000003852 triazoles Chemical class 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 9
- 229910052796 boron Inorganic materials 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 150000002430 hydrocarbons Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims description 6
- IRTLROCMFSDSNF-UHFFFAOYSA-N 2-phenyl-1h-pyrrole Chemical compound C1=CNC(C=2C=CC=CC=2)=C1 IRTLROCMFSDSNF-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 5
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical group C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 3
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 claims description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical group C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 claims description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 3
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 3
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- FQOBINBWTPHVEO-UHFFFAOYSA-N pyrazino[2,3-b]pyrazine Chemical group N1=CC=NC2=NC=CN=C21 FQOBINBWTPHVEO-UHFFFAOYSA-N 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical group N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 239000000463 material Substances 0.000 description 19
- 238000002347 injection Methods 0.000 description 16
- 239000007924 injection Substances 0.000 description 16
- 230000032258 transport Effects 0.000 description 16
- 230000005525 hole transport Effects 0.000 description 13
- 230000000903 blocking effect Effects 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 230000005281 excited state Effects 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 239000011575 calcium Substances 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- QKLPIYTUUFFRLV-YTEMWHBBSA-N 1,4-bis[(e)-2-(2-methylphenyl)ethenyl]benzene Chemical compound CC1=CC=CC=C1\C=C\C(C=C1)=CC=C1\C=C\C1=CC=CC=C1C QKLPIYTUUFFRLV-YTEMWHBBSA-N 0.000 description 1
- BCASZEAAHJEDAL-PHEQNACWSA-N 1,4-bis[(e)-2-(4-methylphenyl)ethenyl]benzene Chemical compound C1=CC(C)=CC=C1\C=C\C(C=C1)=CC=C1\C=C\C1=CC=C(C)C=C1 BCASZEAAHJEDAL-PHEQNACWSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- TWZYORZPYCRVAX-UHFFFAOYSA-N 2-(2h-thiopyran-1-ylidene)propanedinitrile Chemical compound N#CC(C#N)=S1CC=CC=C1 TWZYORZPYCRVAX-UHFFFAOYSA-N 0.000 description 1
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 1
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 1
- KYGSXEYUWRFVNY-UHFFFAOYSA-N 2-pyran-2-ylidenepropanedinitrile Chemical compound N#CC(C#N)=C1OC=CC=C1 KYGSXEYUWRFVNY-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- VLDFXDUAENINOO-UHFFFAOYSA-N 4-methyl-2-[4-(4-methyl-5-phenyl-1,3-oxazol-2-yl)phenyl]-5-phenyl-1,3-oxazole Chemical compound CC=1N=C(C=2C=CC(=CC=2)C=2OC(=C(C)N=2)C=2C=CC=CC=2)OC=1C1=CC=CC=C1 VLDFXDUAENINOO-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- AIXZBGVLNVRQSS-UHFFFAOYSA-N 5-tert-butyl-2-[5-(5-tert-butyl-1,3-benzoxazol-2-yl)thiophen-2-yl]-1,3-benzoxazole Chemical compound CC(C)(C)C1=CC=C2OC(C3=CC=C(S3)C=3OC4=CC=C(C=C4N=3)C(C)(C)C)=NC2=C1 AIXZBGVLNVRQSS-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- MASVCBBIUQRUKL-UHFFFAOYSA-N POPOP Chemical compound C=1N=C(C=2C=CC(=CC=2)C=2OC(=CN=2)C=2C=CC=CC=2)OC=1C1=CC=CC=C1 MASVCBBIUQRUKL-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- FZYXURZMAQWVFY-UHFFFAOYSA-K [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.FC1=C(C#N)C(F)=CC(C=2N=CC=CC=2)=C1.FC1=C(C#N)C(F)=CC(C=2N=CC=CC=2)=C1 Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.FC1=C(C#N)C(F)=CC(C=2N=CC=CC=2)=C1.FC1=C(C#N)C(F)=CC(C=2N=CC=CC=2)=C1 FZYXURZMAQWVFY-UHFFFAOYSA-K 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000005606 carbostyryl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
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- 238000012921 fluorescence analysis Methods 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
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- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 239000011780 sodium chloride Substances 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical compound C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
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Abstract
본 발명은 하기 화학식 1로 표시되는 유기화합물 및 이를 포함하는 유기전계발광소자를 제공한다:
[화학식 1]
The present invention provides an organic compound represented by the following formula (1) and an organic electroluminescent device containing the same:
[Formula 1]
Description
본 발명은 디스플레이 분야에 관한 것으로서, 보다 상세하게는 디스플레이의 일종인 유기전계발광소자 제조시 이용할 수 있는 유기화합물 및 이를 포함하는 유기전계발광소자에 관한 것이다.The present invention relates to the field of displays, and more specifically, to organic compounds that can be used in the manufacture of organic electroluminescent devices, which are a type of display, and organic electroluminescent devices containing the same.
현재까지 평판 디스플레이의 대부분을 액정 디스플레이가 차지하고 있으나, 보다 경제적이고 성능이 뛰어나면서 액정 디스플레이와 차별화된 새로운 평판 디스플레이를 개발하려는 노력이 전세계적으로 활발히 진행되고 있다. 최근 차세대 평판 디스플레이로 각광을 받고 있는 유기전계발광소자는 액정 디스플레이에 비해 낮은 구동전압, 빠른 응답속도 및 광시야각 등의 장점을 가지고 있다.Liquid crystal displays account for most of the flat displays to date, but efforts are being made around the world to develop new flat displays that are more economical, have better performance, and are differentiated from liquid crystal displays. Organic electroluminescent devices, which have recently been in the spotlight as next-generation flat displays, have advantages such as low driving voltage, fast response speed, and wide viewing angle compared to liquid crystal displays.
유기전계발광소자의 구조는 기판, 애노드, 애노드에서 정공을 받아들이는 정공주입층, 정공을 수송하는 정공수송층, 발광층으로부터 정공수송층으로 전자의 진입을 저지하는 전자 저지층, 정공과 전자가 결합하여 빛을 내는 발광층, 발광층에서 전자 수송층으로 정공의 진입을 저지하는 정공 저지층, 캐소드에서 전자를 받아들여 발광층으로 수송하는 전자 수송층, 캐소드에서 전자를 받아들이는 전자 주입층 및 캐소드로 구성되어 있다. 경우에 따라서 별도의 발광층 없이 전자 수송층이나 정공수송층에 소량의 형광 또는 인광성 염료를 도핑하여 발광층을 구성할 수도 있으며, 고분자를 사용할 경우에는 일반적으로 하나의 고분자가 정공수송층과 발광층 및 전자 수송층의 역할을 동시에 수행할 수 있다. 두 전극 사이의 유기물 박막층들은 진공증착법 또는 스핀 코팅, 잉크젯 프린팅, 레이저 열전사법등의 방법으로 형성된다. 이렇게 유기전계발광소자를 다층 박막 구조로 제작하는 이유는 전극과 유기물 사이의 계면 안정화를 위함이며 또한 유기물질의 경우, 정공과 전자의 이동 속도 차이가 크므로 적절한 정공수송층과 전자 수송층을 사용하여 정공과 전자를 발광층으로 효과적으로 전달하여 정공과 전자의 밀도가 균형을 이루도록 하면 발광 효율을 높일 수 있기 때문이다.The structure of an organic electroluminescent device consists of a substrate, an anode, a hole injection layer that accepts holes from the anode, a hole transport layer that transports holes, an electron blocking layer that blocks electrons from entering the hole transport layer from the light-emitting layer, and holes and electrons combine to produce light. It consists of a light emitting layer that emits light, a hole blocking layer that blocks the entry of holes from the light emitting layer to the electron transport layer, an electron transport layer that accepts electrons from the cathode and transports them to the light emitting layer, an electron injection layer that accepts electrons from the cathode, and a cathode. In some cases, a light-emitting layer may be formed by doping a small amount of fluorescent or phosphorescent dye into the electron transport layer or hole transport layer without a separate light-emitting layer. When polymers are used, one polymer generally serves as the hole transport layer, light-emitting layer, and electron transport layer. can be performed simultaneously. The organic thin film layers between the two electrodes are formed by methods such as vacuum deposition, spin coating, inkjet printing, or laser thermal transfer. The reason why organic electroluminescent devices are manufactured with a multi-layer thin film structure is to stabilize the interface between the electrode and the organic material. Also, in the case of organic materials, the difference in movement speed between holes and electrons is large, so an appropriate hole transport layer and electron transport layer are used to This is because luminous efficiency can be increased by effectively transferring excess electrons to the light emitting layer and balancing the densities of holes and electrons.
유기전계발광소자의 구동 원리는 다음과 같다. 상기 애노드 및 캐소드 간에 전압을 인가하면 애노드로부터 주입된 정공은 정공주입층 및 정공수송층을 경유하여 발광층으로 이동된다. 한편, 전자는 캐소드로부터 전자 주입층 및 전자 수송층을 경유하여 발광층에 주입되고 발광층 영역에서 캐리어들이 재결합하여 엑시톤(exiton)을 생성한다. 이 엑시톤이 여기 상태에서 기저 상태로 변화되고, 이로 인하여 발광층의 형광성 분자가 발광함으로써 화상이 형성된다. 이때 여기 상태가 일중항 여기 상태를 통하여 기저 상태로 떨어지면서 발광하는 것을 "형광"이라고 하며, 삼중항 여기 상태를 통하여 기저 상태로 떨어지면서 발광하는 것을 "인광"이라고 한다. 형광의 경우, 일중항 여기 상태의 확률이 25%(삼중항 상태 75%)이며, 발광 효율의 한계가 있는 반면에 인광을 사용하면 삼중항 상태 75%와 일중항 여기 상태 25%까지 발광에 이용할 수 있으므로 이론적으로 내부양자 효율 100%까지 가능하다.The driving principle of the organic electroluminescent device is as follows. When a voltage is applied between the anode and the cathode, holes injected from the anode are moved to the light emitting layer via the hole injection layer and the hole transport layer. Meanwhile, electrons are injected into the light-emitting layer from the cathode via the electron injection layer and the electron transport layer, and carriers recombine in the light-emitting layer area to generate excitons. This exciton changes from the excited state to the ground state, and as a result, the fluorescent molecules in the light-emitting layer emit light, forming an image. At this time, light emission as the excited state falls to the ground state through a singlet excitation state is called “fluorescence,” and light emission as the excited state falls to the ground state through a triplet excitation state is called “phosphorescence.” In the case of fluorescence, the probability of a singlet excited state is 25% (75% of a triplet state), and there is a limit to the luminous efficiency, whereas when using phosphorescence, up to 75% of the triplet state and 25% of the singlet excited state can be used for luminescence. Therefore, theoretically, internal quantum efficiency of up to 100% is possible.
이러한 유기전계발광소자에 있어 가장 문제가 되는 것은 수명과 효율인데, 디스플레이가 대면적화 되면서 이러한 효율이나 수명문제는 반드시 해결해야되는 상황이다.The biggest problems with these organic electroluminescent devices are lifespan and efficiency, but as displays become larger in area, these efficiency and lifespan issues must be resolved.
본 발명은 종래기술의 상기와 같은 문제를 해소하기 위하여 안출된 것으로서, The present invention was devised to solve the above problems of the prior art,
유기전계발광소자의 재료로 사용되어 유기전계발광소자의 발광 효율 및 발광 수명을 향상시키는 신규한 유기화합물을 제공하는 것을 목적으로한다.The purpose is to provide a novel organic compound that is used as a material for organic electroluminescent devices and improves the luminous efficiency and luminous lifetime of organic electroluminescent devices.
또한, 본 발명은 상기와 같은 유기전계발광소자의 재료를 포함함으로써, 구동전압, 발광 효율 및 발광 수명이 향상된 유기전계발광소자를 제공하는 것을 목적으로한다.In addition, the present invention aims to provide an organic electroluminescent device with improved driving voltage, luminous efficiency, and luminous lifetime by including the organic electroluminescent device material as described above.
본 발명은 하기 화학식 1로 표시되는 유기화합물을 제공한다:The present invention provides an organic compound represented by the following formula (1):
[화학식 1][Formula 1]
상기 식에서 In the above equation
R1는 아다만탄, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 또는 탄소수 3 내지 40의 시클로 알킬기이거나,R1 is adamantane, straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, thioalkyl with 1 to 40 carbon atoms, or cycloalkyl group with 3 to 40 carbon atoms,
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌 및 페릴렌으로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌, 페릴렌, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~60의 방향족 탄화수소기이거나,Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, Substituted or unsubstituted with one or more selected from the group consisting of thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene and perylene Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group and It is an aromatic hydrocarbon group having 6 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of quinolinyl groups, or
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌 및 페릴렌으로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌, 페릴렌, 9,9-디메틸플루오레닐, 스파이로바이플루오레닐, 티오펜기, 퓨라닐기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 피리딘기, 바이피리딘기, 피리미단기, 트리아진기, 트리아졸기, 아크리딘기, 피리다진기, 피라진기, 퀴놀린기, 퀴나졸린기, 퀴녹살린기, 프탈라진기, 피리도피리딘기, 피리도피라진기, 피라지노피라진기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨란기, 페난쓰롤리닐기(phenanthroline), 티아졸기, 이소옥사졸기, 옥사디아졸기, 티아디아졸기, 벤조티아졸기, 페노티아진기, 디벤조퓨란기, 디하이드로페노티아진기, 디하이드로벤조이소퀴놀린기, 크로멘기 및 헥사하이드로카바졸릴기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N, B, P 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 70의 헤테로 방향족 탄화수소기이거나, Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, Substituted or unsubstituted with one or more selected from the group consisting of thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene and perylene Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, spirobifluorenyl, thiophene group, furanyl group, pyrrole group, imidazole group, thiazole group, Oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimi group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, Pyridopyridine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiol ophene group, benzofuran group, phenanthrolinyl group, thiazole group, isoxazole group, oxadiazole group, thiadiazole group, benzothiazole group, phenothiazine group, dibenzofuran group, dihydrophenothiazine group, di It is substituted or unsubstituted with one or more elements selected from the group consisting of hydrobenzoisoquinoline group, chromene group, and hexahydrocarbazolyl group, and contains one or more elements selected from the group consisting of S, O, N, B, P, and Si. It is a heteroaromatic hydrocarbon group having 5 to 70 carbon atoms, or
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 및 탄소수 3 내지 40의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌, 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌, 페릴렌, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이며;Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene, phenyl, substituted or unsubstituted with one or more types selected from the group consisting of thioalkyl groups having 1 to 40 carbon atoms, and cycloalkyl groups having 3 to 40 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, di-substituted or unsubstituted with one or more selected from the group consisting of rylene It is an amino group substituted with one or more types selected from the group consisting of benzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups;
Z1, Z2, Z3 및 Z4는 각각 독립적으로 단일결합이거나 산소, 황이거나 할로겐, CN, CF3, 페닐, 나프타닐, 페닐 피리디닐, 페닐 피리미디닐, 페닐 이미다졸 및 Si(CH3)3기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 페닐이며;Z1, Z2, Z3, and Z4 are each independently a single bond or oxygen, sulfur, halogen, CN, CF 3 , phenyl, naphthanyl, phenyl pyridinyl, phenyl pyrimidinyl, phenyl imidazole, and Si(CH 3 ) 3 group. It is phenyl substituted or unsubstituted with one or more selected from the group consisting of;
a, b, c는 각각 독립적으로 0 또는 1이고, 0일 경우 결합이 존재하지 않는 것을 의미하며;a, b, and c are each independently 0 or 1, and 0 means that no bond exists;
d, e는 각각 독립적으로 0 ~ 5의 정수이고, 0일 경우 단순한 단일결합을 의미하며;d and e are each independently integers from 0 to 5, and when 0, it means a simple single bond;
m, n은 각각 독립적으로 0~3의 정수이고, m + n 은 3이하이며;m and n are each independently integers from 0 to 3, and m + n is 3 or less;
M은 Ir 또는 Pt 또는 Os 또는 Au 또는 Co 또는 C 또는 Si 또는 Ge이며;M is Ir or Pt or Os or Au or Co or C or Si or Ge;
X1은 탄소 또는 질소이며;X1 is carbon or nitrogen;
R2, R3는 각각 독립적으로 아다만탄, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 또는 탄소수 3 내지 30의 시클로 알킬기이거나,R2 and R3 are each independently adamantane, straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, thioalkyl with 1 to 30 carbon atoms, or cycloalkyl group with 3 to 30 carbon atoms,
삼중수소, 중수소, 수소, 아다만탄, 할로겐, CN, CF3, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 탄소수 3 내지 30의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐기, 피렌일, 트리페닐렌 및 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 페닐아민, 바이페닐아민, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐, 퀴놀리닐, 페닐 피리디닐, 페닐아민, 바이페닐아민, 페닐 피리미디닐, 페닐 이미다졸, 이미다조피라지닐 및 페닐 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~50의 방향족 탄화수소기이거나,Tritium, deuterium, hydrogen, adamantane, halogen, CN, CF 3 , straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, thioalkyl with 1 to 30 carbon atoms, cyclo with 3 to 30 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene substituted or unsubstituted with one or more selected from the group consisting of alkyl, phenyl, biphenyl, naphthyl, anthracenyl group, pyrenyl, triphenylene, and perylene. , perylene, phenylamine, biphenylamine, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyrrole. An aromatic hydrocarbon group having 6 to 50 carbon atoms that is substituted or unsubstituted with one or more selected from the group consisting of dinyl, phenylamine, biphenylamine, phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl and phenyl triazinyl groups, or
삼중수소, 중수소, 아다만탄, 할로겐, CN, CF3, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 탄소수 3 내지 30의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐기, 피렌일, 트리페닐렌 및 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 9,9-디메틸플루오레닐, 스파이로바이플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐, 퀴놀리닐, 페닐 피리디닐, 페닐 피리미디닐, 페닐 이미다졸, 이미다조피라지닐 및 페닐 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N, B, P 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 60의 헤테로 방향족 탄화수소기이거나,Tritium, deuterium, adamantane, halogen, CN, CF 3 , straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, thioalkyl with 1 to 30 carbon atoms, cycloalkyl with 3 to 30 carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, phenyl, substituted or unsubstituted with one or more selected from the group consisting of phenyl, biphenyl, naphthyl, anthracenyl group, pyrenyl, triphenylene, and perylene. rylene, 9,9-dimethylfluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyridinyl, Substituted or unsubstituted with one or more selected from the group consisting of phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl and phenyl triazinyl groups, and one selected from the group consisting of S, O, N, B, P and Si. It is a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms containing the above elements, or
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 및 탄소수 3 내지 30의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌,페릴렌기로 치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이며;Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, Phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene, phenyl, substituted or unsubstituted with one or more types selected from the group consisting of thioalkyl groups having 1 to 30 carbon atoms and cycloalkyl groups having 3 to 30 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl substituted with rylene group. , an amino group substituted with one or more types selected from the group consisting of pyrazinyl and pyrimidinyl groups;
R4, R5, R6, R7, R8, R9 및 R10은 각각 독립적으로 삼중수소, 수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, 탄소수 1 내지 20의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 20의 알콕시, 탄소수 1 내지 20의 티오알킬, 또는 탄소수 3 내지 20의 시클로 알킬기이거나,R4, R5, R6, R7, R8, R9 and R10 are each independently selected from tritium, hydrogen, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , and having 1 to 20 carbon atoms. It is a straight-chain or branched-chain alkyl group, an alkoxyl group with 1 to 20 carbon atoms, a thioalkyl group with 1 to 20 carbon atoms, or a cycloalkyl group with 3 to 20 carbon atoms, or
삼중수소, 중수소, 수소, 아다만탄, 할로겐, CN, CF3, 탄소수 1 내지 20의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 20의 알콕시, 탄소수 1 내지 20의 티오알킬, 탄소수 3 내지 20의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐기, 피렌일, 트리페닐렌 및 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 페닐아민, 바이페닐아민, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐, 퀴놀리닐, 페닐 피리디닐, 페닐아민, 바이페닐아민, 페닐 피리미디닐, 페닐 이미다졸, 이미다조피라지닐 및 페닐 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~50의 방향족 탄화수소기이거나,Tritium, deuterium, hydrogen, adamantane, halogen, CN, CF 3 , straight or branched chain alkyl with 1 to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms, thioalkyl with 1 to 20 carbon atoms, cyclo with 3 to 20 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene substituted or unsubstituted with one or more selected from the group consisting of alkyl, phenyl, biphenyl, naphthyl, anthracenyl group, pyrenyl, triphenylene, and perylene. , perylene, phenylamine, biphenylamine, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyrrole. An aromatic hydrocarbon group having 6 to 50 carbon atoms that is substituted or unsubstituted with one or more selected from the group consisting of dinyl, phenylamine, biphenylamine, phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl and phenyl triazinyl groups, or
삼중수소, 중수소, 아다만탄, 할로겐, CN, CF3, 탄소수 1 내지 20의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 20의 알콕시, 탄소수 1 내지 20의 티오알킬, 탄소수 3 내지 20의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐기, 피렌일, 트리페닐렌 및 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 9,9-디메틸플루오레닐, 스파이로바이플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐, 퀴놀리닐, 페닐 피리디닐, 페닐 피리미디닐, 페닐 이미다졸, 이미다조피라지닐 및 페닐 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N, B, P 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 60의 헤테로 방향족 탄화수소기이거나,Tritium, deuterium, adamantane, halogen, CN, CF 3 , straight or branched chain alkyl with 1 to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms, thioalkyl with 1 to 20 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, phenyl, substituted or unsubstituted with one or more selected from the group consisting of phenyl, biphenyl, naphthyl, anthracenyl group, pyrenyl, triphenylene, and perylene. rylene, 9,9-dimethylfluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyridinyl, Substituted or unsubstituted with one or more selected from the group consisting of phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl and phenyl triazinyl groups, and one selected from the group consisting of S, O, N, B, P and Si. It is a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms containing the above elements, or
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 및 탄소수 3 내지 30의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌 및 페릴렌기로 치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이다.Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, Phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene and phenyl substituted or unsubstituted with one or more types selected from the group consisting of thioalkyl groups having 1 to 30 carbon atoms and cycloalkyl groups having 3 to 30 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl substituted with rylene group. , an amino group substituted with one or more types selected from the group consisting of pyrazinyl and pyrimidinyl groups.
본 발명은 유기전계발광소자의 재료로 사용되어 유기전계발광소자의 발광 효율 및 발광 수명을 향상시키는 신규한 유기화합물을 제공한다.The present invention provides a novel organic compound that is used as a material for organic electroluminescent devices and improves the luminous efficiency and luminous lifetime of organic electroluminescent devices.
또한, 본 발명은 상기와 같은 유기전계발광소자의 재료를 포함함으로써, 구동전압, 발광 효율 및 발광 수명이 향상된 유기전계발광소자를 제공한다.In addition, the present invention provides an organic electroluminescent device with improved driving voltage, luminous efficiency, and luminous lifetime by including the organic electroluminescent device material as described above.
본 발명은 하기 화학식 1로 표시되는 신규한 유기화합물에 관한 것이다:The present invention relates to a novel organic compound represented by the following formula (1):
[화학식 1][Formula 1]
상기 식에서 In the above equation
R1는 아다만탄, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 또는 탄소수 3 내지 40의 시클로 알킬기이거나,R1 is adamantane, straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, thioalkyl with 1 to 40 carbon atoms, or cycloalkyl group with 3 to 40 carbon atoms,
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌 및 페릴렌으로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌, 페릴렌, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~60의 방향족 탄화수소기이거나,Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, Substituted or unsubstituted with one or more selected from the group consisting of thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene and perylene Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group and It is an aromatic hydrocarbon group having 6 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of quinolinyl groups, or
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌 및 페릴렌으로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌, 페릴렌, 9,9-디메틸플루오레닐, 스파이로바이플루오레닐, 티오펜기, 퓨라닐기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 피리딘기, 바이피리딘기, 피리미단기, 트리아진기, 트리아졸기, 아크리딘기, 피리다진기, 피라진기, 퀴놀린기, 퀴나졸린기, 퀴녹살린기, 프탈라진기, 피리도피리딘기, 피리도피라진기, 피라지노피라진기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨란기, 페난쓰롤리닐기(phenanthroline), 티아졸기, 이소옥사졸기, 옥사디아졸기, 티아디아졸기, 벤조티아졸기, 페노티아진기, 디벤조퓨란기, 디하이드로페노티아진기, 디하이드로벤조이소퀴놀린기, 크로멘기 및 헥사하이드로카바졸릴기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N, B, P 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 70의 헤테로 방향족 탄화수소기이거나, Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, Substituted or unsubstituted with one or more selected from the group consisting of thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene and perylene Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, spirobifluorenyl, thiophene group, furanyl group, pyrrole group, imidazole group, thiazole group, Oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimi group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, Pyridopyridine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiol ophene group, benzofuran group, phenanthrolinyl group, thiazole group, isoxazole group, oxadiazole group, thiadiazole group, benzothiazole group, phenothiazine group, dibenzofuran group, dihydrophenothiazine group, di It is substituted or unsubstituted with one or more elements selected from the group consisting of hydrobenzoisoquinoline group, chromene group, and hexahydrocarbazolyl group, and contains one or more elements selected from the group consisting of S, O, N, B, P, and Si. It is a heteroaromatic hydrocarbon group having 5 to 70 carbon atoms, or
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 및 탄소수 3 내지 40의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌, 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌, 페릴렌, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이며;Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene, phenyl, substituted or unsubstituted with one or more types selected from the group consisting of thioalkyl groups having 1 to 40 carbon atoms, and cycloalkyl groups having 3 to 40 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, di-substituted or unsubstituted with one or more selected from the group consisting of rylene It is an amino group substituted with one or more types selected from the group consisting of benzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups;
Z1, Z2, Z3 및 Z4는 각각 독립적으로 단일결합이거나 산소, 황이거나 할로겐, CN, CF3, 페닐, 나프타닐, 페닐 피리디닐, 페닐 피리미디닐, 페닐 이미다졸 및 Si(CH3)3기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 페닐이며;Z1, Z2, Z3, and Z4 are each independently a single bond or oxygen, sulfur, halogen, CN, CF 3 , phenyl, naphthanyl, phenyl pyridinyl, phenyl pyrimidinyl, phenyl imidazole, and Si(CH 3 ) 3 group. It is phenyl substituted or unsubstituted with one or more selected from the group consisting of;
a, b, c는 각각 독립적으로 0 또는 1이고, 0일 경우 결합이 존재하지 않는 것을 의미하며;a, b, and c are each independently 0 or 1, and 0 means that no bond exists;
d, e는 각각 독립적으로 0 ~ 5의 정수이고, 0일 경우 단순한 단일결합을 의미하며;d and e are each independently integers from 0 to 5, and when 0, it means a simple single bond;
m, n은 각각 독립적으로 0~3의 정수이고, m + n 은 3이하이며;m and n are each independently integers from 0 to 3, and m + n is 3 or less;
M은 Ir 또는 Pt 또는 Os 또는 Au 또는 Co 또는 C 또는 Si 또는 Ge이며;M is Ir or Pt or Os or Au or Co or C or Si or Ge;
X1은 탄소 또는 질소이며;X1 is carbon or nitrogen;
R2, R3는 각각 독립적으로 아다만탄, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 또는 탄소수 3 내지 30의 시클로 알킬기이거나,R2 and R3 are each independently adamantane, straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, thioalkyl with 1 to 30 carbon atoms, or cycloalkyl group with 3 to 30 carbon atoms,
삼중수소, 중수소, 수소, 아다만탄, 할로겐, CN, CF3, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 탄소수 3 내지 30의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐기, 피렌일, 트리페닐렌 및 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 페닐아민, 바이페닐아민, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐, 퀴놀리닐, 페닐 피리디닐, 페닐아민, 바이페닐아민, 페닐 피리미디닐, 페닐 이미다졸, 이미다조피라지닐 및 페닐 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~50의 방향족 탄화수소기이거나,Tritium, deuterium, hydrogen, adamantane, halogen, CN, CF 3 , straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, thioalkyl with 1 to 30 carbon atoms, cyclo with 3 to 30 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene substituted or unsubstituted with one or more selected from the group consisting of alkyl, phenyl, biphenyl, naphthyl, anthracenyl group, pyrenyl, triphenylene, and perylene. , perylene, phenylamine, biphenylamine, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyrrole. An aromatic hydrocarbon group having 6 to 50 carbon atoms that is substituted or unsubstituted with one or more selected from the group consisting of dinyl, phenylamine, biphenylamine, phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl and phenyl triazinyl groups, or
삼중수소, 중수소, 아다만탄, 할로겐, CN, CF3, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 탄소수 3 내지 30의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐기, 피렌일, 트리페닐렌 및 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 9,9-디메틸플루오레닐, 스파이로바이플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐, 퀴놀리닐, 페닐 피리디닐, 페닐 피리미디닐, 페닐 이미다졸, 이미다조피라지닐 및 페닐 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N, B, P 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 60의 헤테로 방향족 탄화수소기이거나,Tritium, deuterium, adamantane, halogen, CN, CF 3 , straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, thioalkyl with 1 to 30 carbon atoms, cycloalkyl with 3 to 30 carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, phenyl, substituted or unsubstituted with one or more selected from the group consisting of phenyl, biphenyl, naphthyl, anthracenyl group, pyrenyl, triphenylene, and perylene. rylene, 9,9-dimethylfluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyridinyl, Substituted or unsubstituted with one or more selected from the group consisting of phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl and phenyl triazinyl groups, and one selected from the group consisting of S, O, N, B, P and Si. It is a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms containing the above elements, or
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 및 탄소수 3 내지 30의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌,페릴렌기로 치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이며;Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, Phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene, phenyl, substituted or unsubstituted with one or more types selected from the group consisting of thioalkyl groups having 1 to 30 carbon atoms and cycloalkyl groups having 3 to 30 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl substituted with rylene group. , an amino group substituted with one or more types selected from the group consisting of pyrazinyl and pyrimidinyl groups;
R4, R5, R6, R7, R8, R9 및 R10은 각각 독립적으로 삼중수소, 수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, 탄소수 1 내지 20의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 20의 알콕시, 탄소수 1 내지 20의 티오알킬, 또는 탄소수 3 내지 20의 시클로 알킬기이거나,R4, R5, R6, R7, R8, R9 and R10 are each independently selected from tritium, hydrogen, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , and having 1 to 20 carbon atoms. It is a straight-chain or branched-chain alkyl group, an alkoxyl group with 1 to 20 carbon atoms, a thioalkyl group with 1 to 20 carbon atoms, or a cycloalkyl group with 3 to 20 carbon atoms, or
삼중수소, 중수소, 수소, 아다만탄, 할로겐, CN, CF3, 탄소수 1 내지 20의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 20의 알콕시, 탄소수 1 내지 20의 티오알킬, 탄소수 3 내지 20의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐기, 피렌일, 트리페닐렌 및 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 페닐아민, 바이페닐아민, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐, 퀴놀리닐, 페닐 피리디닐, 페닐아민, 바이페닐아민, 페닐 피리미디닐, 페닐 이미다졸, 이미다조피라지닐 및 페닐 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~50의 방향족 탄화수소기이거나,Tritium, deuterium, hydrogen, adamantane, halogen, CN, CF 3 , straight or branched chain alkyl with 1 to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms, thioalkyl with 1 to 20 carbon atoms, cyclo with 3 to 20 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene substituted or unsubstituted with one or more selected from the group consisting of alkyl, phenyl, biphenyl, naphthyl, anthracenyl group, pyrenyl, triphenylene, and perylene. , perylene, phenylamine, biphenylamine, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyrrole. An aromatic hydrocarbon group having 6 to 50 carbon atoms that is substituted or unsubstituted with one or more selected from the group consisting of dinyl, phenylamine, biphenylamine, phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl and phenyl triazinyl groups, or
삼중수소, 중수소, 아다만탄, 할로겐, CN, CF3, 탄소수 1 내지 20의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 20의 알콕시, 탄소수 1 내지 20의 티오알킬, 탄소수 3 내지 20의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐기, 피렌일, 트리페닐렌 및 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 9,9-디메틸플루오레닐, 스파이로바이플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐, 퀴놀리닐, 페닐 피리디닐, 페닐 피리미디닐, 페닐 이미다졸, 이미다조피라지닐 및 페닐 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N, B, P 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 60의 헤테로 방향족 탄화수소기이거나,Tritium, deuterium, adamantane, halogen, CN, CF 3 , straight or branched chain alkyl with 1 to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms, thioalkyl with 1 to 20 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, phenyl, substituted or unsubstituted with one or more selected from the group consisting of phenyl, biphenyl, naphthyl, anthracenyl group, pyrenyl, triphenylene, and perylene. rylene, 9,9-dimethylfluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyridinyl, Substituted or unsubstituted with one or more selected from the group consisting of phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl and phenyl triazinyl groups, and one selected from the group consisting of S, O, N, B, P and Si. It is a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms containing the above elements, or
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 및 탄소수 3 내지 30의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌 및 페릴렌기로 치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이다.Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, Phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene and phenyl substituted or unsubstituted with one or more types selected from the group consisting of thioalkyl groups having 1 to 30 carbon atoms and cycloalkyl groups having 3 to 30 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl substituted with rylene group. , an amino group substituted with one or more types selected from the group consisting of pyrazinyl and pyrimidinyl groups.
상기 유기화합물의 구체적인 예로는 하기 화합물 1 내지 420 중의 어느 하나를 들 수 있다.Specific examples of the organic compounds include any one of the following compounds 1 to 420.
이하에서, 본 발명의 유기전계발광소자에 대하여 예를 들어 설명한다. 그러나, 하기에 예시된 내용이 본 발명의 유기전계발광소자를 한정하는 것은 아니다.Below, the organic electroluminescent device of the present invention will be described as an example. However, the contents illustrated below do not limit the organic electroluminescent device of the present invention.
본 발명에 따른 유기 전계발광 소자의 제조방법으로는, 먼저 기판표면에 양극용 물질을 통상적인 방법으로 코팅하여 양극을 형성한다. 이때, 사용되는 기판은 투명성, 표면평활성, 취급용이성 및 방수성이 우수한 유리기판 또는 투명플라스틱기판이 바람직하다. 또한, 양극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등이 사용될 수 있다.In the method of manufacturing an organic electroluminescent device according to the present invention, an anode is first formed by coating the surface of a substrate with an anode material in a conventional manner. At this time, the substrate used is preferably a glass substrate or a transparent plastic substrate with excellent transparency, surface smoothness, ease of handling, and waterproofness. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, can be used as materials for the anode.
다음으로, 상기 양극표면에 정공주입층(HIL) 물질을 통상적인 방법으로 진공열증착 또는 스핀코팅하여 정공주입층을 형성한다. 이러한 정공주입층 물질로는 구리프탈로시아닌(CuPc), 4,4',4"-트리스(3-메틸페닐아미노)트리페닐아민(m-MTDATA), 4,4',4"-트리스(3-메틸페닐아미노)페녹시벤젠(m-MTDAPB), 스타버스트(starburst)형아민류인 4,4',4"-트리(N-카바졸릴)트리페닐아민(TCTA), 4,4',4"-트리스(N-(2-나프틸)-N-페닐아미노)-트리페닐아민(2-TNATA) 또는 이데미츠사(Idemitsu)에서 구입가능한 IDE406을 예로 들 수 있다.Next, a hole injection layer (HIL) material is vacuum thermally deposited or spin coated on the surface of the anode using a conventional method to form a hole injection layer. Such hole injection layer materials include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenyl) Amino)phenoxybenzene (m-MTDAPB), starburst type amines 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris Examples include (N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA) or IDE406 available from Idemitsu.
상기 정공주입층 표면에 정공수송층(HTL) 물질을 통상적인 방법으로 진공열증착 또는 스핀코팅하여 정공수송층을 형성한다. 이때, 정공수송층 물질로는 비스(N-(1-나프틸-n-페닐))벤지딘(α-NPD), N,N'-다이(나프탈렌-1-일)-N,N'-바이페닐-벤지딘(NPB) 또는 N,N'-바이페닐-N,N'-비스(3-메틸페닐)-1,1'-바이페닐-4,4'-다이아민(TPD)을 예로 들 수 있으며, 더욱 바람직하게는 본 발명의 화학식 2의 화합물이 사용될 수 있다.A hole transport layer (HTL) material is vacuum thermally deposited or spin coated on the surface of the hole injection layer using a conventional method to form a hole transport layer. At this time, the hole transport layer materials include bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-di(naphthalen-1-yl)-N,N'-biphenyl -Benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), More preferably, the compound of formula 2 of the present invention can be used.
상기 정공수송층 표면에 발광층(EML) 물질을 통상적인 방법으로 진공열증착 또는 스핀코팅하여 발광층을 형성한다. 이때, 사용되는 발광 재료로서 예를 들면 축광 형광재료, 형광증백제, 레이저 색소, 유기 신틸레이터 및 형광 분석용 시약을 들 수 있다. 구체적으로는, 카바졸계 화합물, 포스핀옥사이드계 화합물, 카바졸계 포스핀옥사이드 화합물, 비스((3,5-디플루오로-4-시아노페닐)피리딘) 이리듐 피콜리네이트(FCNIrpic), 트리스(8-히드록시퀴놀린) 알루미늄(Alq3), 안트라센, 페난트렌, 피렌, 크리센, 페릴렌, 코로넨, 루브렌 및 퀴나크리돈과 같은 폴리아로마틱 화합물, 퀴터페닐과 같은 올리고페닐렌 화합물, 1,4-비스 (2-메틸스티릴)벤젠, 1,4-비스(4-메틸스티릴)벤젠, 1,4-비스(4-메틸-5-페닐-2-옥사졸릴)벤젠, 1,4-비스(5-페닐-2-옥사졸릴)벤젠, 2,5-비스(5-t-부틸-2-벤즈옥사졸릴)사이오펜, 1,4-디페닐-1,3-부타디엔, 1,6-디페닐-1,3,5-헥사트리엔, 1,1,4,4-테트라페닐-1,3-부타디엔과 같은 액체신틸레이션용 신틸레이터, 옥신유도체의 금속착체, 쿠마린 색소, 디시아노메틸렌피란 색소, 디시아노메틸렌사이오피란 색소, 폴리메틴 색소, 옥소벤즈안트라센 색소, 크산텐 색소, 카르보스티릴 색소, 페릴렌 색소, 옥사진 화합물, 스틸벤 유도체, 스피로 화합물, 옥사디아졸 화합물 등을 들 수 있다. 특히, 청색 유기전계발광소자의 경우, 본 발명의 화학식 1의 유기화합물을 도판트로 사용하는 것이 바람직할 수 있다. An emitting layer (EML) material is formed on the surface of the hole transport layer by vacuum thermal evaporation or spin coating using a conventional method. At this time, examples of the light-emitting materials used include phosphorescent fluorescent materials, fluorescent whitening agents, laser dyes, organic scintillators, and reagents for fluorescence analysis. Specifically, carbazole-based compounds, phosphine oxide-based compounds, carbazole-based phosphine oxide compounds, bis ((3,5-difluoro-4-cyanophenyl) pyridine) iridium picolinate (FCNIrpic), tris ( 8-hydroxyquinoline) aluminum (Alq3), polyaromatic compounds such as anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds such as quiterphenyl, 1, 4-bis (2-methylstyryl) benzene, 1,4-bis (4-methylstyryl) benzene, 1,4-bis (4-methyl-5-phenyl-2-oxazolyl) benzene, 1,4 -bis(5-phenyl-2-oxazolyl)benzene, 2,5-bis(5-t-butyl-2-benzoxazolyl)thiophene, 1,4-diphenyl-1,3-butadiene, 1, Scintillator for liquid scintillation such as 6-diphenyl-1,3,5-hexatriene, 1,1,4,4-tetraphenyl-1,3-butadiene, metal complex of auxin derivative, coumarin pigment, dicyano Methylenepyran dye, dicyanomethylenethiopyran dye, polymethine dye, oxobenzanthracene dye, xanthene dye, carbostyryl dye, perylene dye, oxazine compound, stilbene derivative, spiro compound, oxadiazole compound, etc. can be mentioned. In particular, in the case of a blue organic electroluminescent device, it may be desirable to use the organic compound of Formula 1 of the present invention as a dopant.
선택적으로는, 정공수송층과 발광층사이에 전자차단층(EBL)을 추가로 형성할 수 있다. Optionally, an electron blocking layer (EBL) may be additionally formed between the hole transport layer and the light emitting layer.
상기 발광층표면에 전자수송층(ETL) 물질을 통상적인 방법으로 진공열증착 또는 스핀코팅하여 전자수송층을 형성한다. 이때, 사용되는 전자수송층 물질의 경우 특별히 제한되지 않으며, 바람직하게는 트리스(8-하이드록시퀴놀리놀라토)알루미늄(Alq3)을 사용할 수 있다.An electron transport layer (ETL) material is vacuum thermally deposited or spin coated on the surface of the light emitting layer using a conventional method to form an electron transport layer. At this time, the electron transport layer material used is not particularly limited, and tris(8-hydroxyquinolinolato)aluminum (Alq 3 ) can be preferably used.
선택적으로는, 발광층과 전자수송층사이에 정공차단층(HBL)을 추가로 형성하고 발광층에 인광도판트를 함께 사용함으로써, 삼중항여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지할 수 있다. Optionally, by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant in the light emitting layer, diffusion of triplet excitons or holes into the electron transport layer can be prevented.
정공차단층의 형성은 정공차단층물질을 통상적인 방법으로 진공열증착 및 스핀코팅하여 실시할 수 있으며, 정공차단층 물질의 경우 특별히 제한되지는 않으나, 바람직하게는 (8-하이드록시퀴놀리놀라토)리튬(Liq), 비스(8-하이드록시-2-메틸퀴놀리놀나토)-알루미늄비페녹사이드(BAlq), 바쏘쿠프로인 (bathocuproine, BCP) 및 LiF 등을 사용할 수 있다.The formation of the hole blocking layer can be performed by vacuum thermal evaporation and spin coating of the hole blocking material by conventional methods. The hole blocking material is not particularly limited, but is preferably (8-hydroxyquinolinola). To) Lithium (Liq), bis(8-hydroxy-2-methylquinolinolnato)-aluminum biphenoxide (BAlq), bathocuproine (BCP), and LiF can be used.
상기 전자수송층 표면에 전자주입층(EIL) 물질을 통상적인 방법으로 진공열증착 또는 스핀코팅하여 전자주입층을 형성한다. 이때, 사용되는 전자주입층 물질로는 LiF, Liq, Li2O, BaO, NaCl, CsF 등의 물질이 사용될 수 있다.An electron injection layer (EIL) material is vacuum thermally deposited or spin coated on the surface of the electron transport layer using a conventional method to form an electron injection layer. At this time, materials such as LiF, Liq, Li 2 O, BaO, NaCl, and CsF may be used as the electron injection layer material.
상기 전자주입층표면에 음극용물질을 통상적인 방법으로 진공열증착하여 음극을 형성한다.A cathode material is vacuum thermally deposited on the surface of the electron injection layer using a conventional method to form a cathode.
이때, 사용되는 음극용물질로는 리튬(Li), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘(Mg), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등이 사용될 수 있다. 또한, 전면발광유기 전계발광 소자의 경우 산화인듐주석(ITO) 또는 산화인듐아연(IZO)를 사용하여 빛이 투과할 수 있는 투명한 음극을 형성할 수도 있다.At this time, the cathode materials used are lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver. (Mg-Ag) etc. may be used. Additionally, in the case of a top-emitting organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) can be used to form a transparent cathode through which light can transmit.
상기 음극의 표면에는 본 발명의 캡핑층 형성용 조성물에 의해 캡핑층(CPL)이 형성될 수 있다.A capping layer (CPL) may be formed on the surface of the cathode using the composition for forming a capping layer of the present invention.
본 발명에 따른 유기전계발광소자는 상술한 바와 같은 순서, 즉 양극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/음극 순으로 제조하여도 되고, 그 반대로 음극/전자주입층/전자수송층/발광층/정공수송층/정공주입층/양극 순서로 제조하여도 무방하다.The organic electroluminescent device according to the present invention may be manufactured in the order described above, that is, anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode, and vice versa, cathode/electron injection layer/cathode. It may be manufactured in the following order: electron transport layer/light emitting layer/hole transport layer/hole injection layer/anode.
Claims (4)
[화학식 1]
상기 식에서
R1는 아다만탄, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 또는 탄소수 3 내지 40의 시클로 알킬기이거나,
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌 및 페릴렌으로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌, 페릴렌, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~60의 방향족 탄화수소기이거나,
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌 및 페릴렌으로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌, 페릴렌, 9,9-디메틸플루오레닐, 스파이로바이플루오레닐, 티오펜기, 퓨라닐기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 피리딘기, 바이피리딘기, 피리미단기, 트리아진기, 트리아졸기, 아크리딘기, 피리다진기, 피라진기, 퀴놀린기, 퀴나졸린기, 퀴녹살린기, 프탈라진기, 피리도피리딘기, 피리도피라진기, 피라지노피라진기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨란기, 페난쓰롤리닐기(phenanthroline), 티아졸기, 이소옥사졸기, 옥사디아졸기, 티아디아졸기, 벤조티아졸기, 페노티아진기, 디벤조퓨란기, 디하이드로페노티아진기, 디하이드로벤조이소퀴놀린기, 크로멘기 및 헥사하이드로카바졸릴기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N, B, P 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 70의 헤테로 방향족 탄화수소기이거나,
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 및 탄소수 3 내지 40의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌, 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌, 페릴렌, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이며;
Z1, Z2, Z3 및 Z4는 각각 독립적으로 단일결합이거나 산소, 황이거나 할로겐, CN, CF3, 페닐, 나프타닐, 페닐 피리디닐, 페닐 피리미디닐, 페닐 이미다졸 및 Si(CH3)3기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 페닐이며;
a, b, c는 각각 독립적으로 0 또는 1이고, 0일 경우 결합이 존재하지 않는 것을 의미하며;
d, e는 각각 독립적으로 0 ~ 5의 정수이고, 0일 경우 단순한 단일결합을 의미하며;
m, n은 각각 독립적으로 0~3의 정수이고, m + n 은 3이하이며;
M은 Ir 또는 Pt 또는 Os 또는 Au 또는 Co 또는 C 또는 Si 또는 Ge이며;
X1은 탄소 또는 질소이며;
R2, R3는 각각 독립적으로 아다만탄, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 또는 탄소수 3 내지 30의 시클로 알킬기이거나,
삼중수소, 중수소, 수소, 아다만탄, 할로겐, CN, CF3, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 탄소수 3 내지 30의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐기, 피렌일, 트리페닐렌 및 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 페닐아민, 바이페닐아민, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐, 퀴놀리닐, 페닐 피리디닐, 페닐아민, 바이페닐아민, 페닐 피리미디닐, 페닐 이미다졸, 이미다조피라지닐 및 페닐 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~50의 방향족 탄화수소기이거나,
삼중수소, 중수소, 아다만탄, 할로겐, CN, CF3, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 탄소수 3 내지 30의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐기, 피렌일, 트리페닐렌 및 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 9,9-디메틸플루오레닐, 스파이로바이플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐, 퀴놀리닐, 페닐 피리디닐, 페닐 피리미디닐, 페닐 이미다졸, 이미다조피라지닐 및 페닐 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N, B, P 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 60의 헤테로 방향족 탄화수소기이거나,
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 및 탄소수 3 내지 30의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌,페릴렌기로 치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이며;
R4, R5, R6, R7, R8, R9 및 R10은 각각 독립적으로 삼중수소, 수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, 탄소수 1 내지 20의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 20의 알콕시, 탄소수 1 내지 20의 티오알킬, 또는 탄소수 3 내지 20의 시클로 알킬기이거나,
삼중수소, 중수소, 수소, 아다만탄, 할로겐, CN, CF3, 탄소수 1 내지 20의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 20의 알콕시, 탄소수 1 내지 20의 티오알킬, 탄소수 3 내지 20의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐기, 피렌일, 트리페닐렌 및 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 페닐아민, 바이페닐아민, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐, 퀴놀리닐, 페닐 피리디닐, 페닐아민, 바이페닐아민, 페닐 피리미디닐, 페닐 이미다졸, 이미다조피라지닐 및 페닐 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~50의 방향족 탄화수소기이거나,
삼중수소, 중수소, 아다만탄, 할로겐, CN, CF3, 탄소수 1 내지 20의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 20의 알콕시, 탄소수 1 내지 20의 티오알킬, 탄소수 3 내지 20의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐기, 피렌일, 트리페닐렌 및 페릴렌로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 9,9-디메틸플루오레닐, 스파이로바이플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐, 퀴놀리닐, 페닐 피리디닐, 페닐 피리미디닐, 페닐 이미다졸, 이미다조피라지닐 및 페닐 트리아지닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N, B, P 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 60의 헤테로 방향족 탄화수소기이거나,
삼중수소, 중수소, 아다만탄, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 30의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 30의 알콕시, 탄소수 1 내지 30의 티오알킬, 및 탄소수 3 내지 30의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 피렌일, 트리페닐렌 및 페릴렌기로 치환된 안트라세닐, 페난트렌일, 피렌일, 트리페닐렌,페릴렌, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이다.Organic compounds represented by the following formula (1):
[Formula 1]
In the above equation
R1 is adamantane, straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, thioalkyl with 1 to 40 carbon atoms, or cycloalkyl group with 3 to 40 carbon atoms,
Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, Substituted or unsubstituted with one or more selected from the group consisting of thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene and perylene Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group and It is an aromatic hydrocarbon group having 6 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of quinolinyl groups, or
Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, Substituted or unsubstituted with one or more selected from the group consisting of thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene and perylene Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, spirobifluorenyl, thiophene group, furanyl group, pyrrole group, imidazole group, thiazole group, Oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimi group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, Pyridopyridine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiol ophene group, benzofuran group, phenanthrolinyl group, thiazole group, isoxazole group, oxadiazole group, thiadiazole group, benzothiazole group, phenothiazine group, dibenzofuran group, dihydrophenothiazine group, di It is substituted or unsubstituted with one or more elements selected from the group consisting of hydrobenzoisoquinoline group, chromene group, and hexahydrocarbazolyl group, and contains one or more elements selected from the group consisting of S, O, N, B, P, and Si. It is a heteroaromatic hydrocarbon group having 5 to 70 carbon atoms, or
Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene, phenyl, substituted or unsubstituted with one or more types selected from the group consisting of thioalkyl groups having 1 to 40 carbon atoms, and cycloalkyl groups having 3 to 40 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, di-substituted or unsubstituted with one or more selected from the group consisting of rylene It is an amino group substituted with one or more types selected from the group consisting of benzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups;
Z1, Z2, Z3, and Z4 are each independently a single bond or oxygen, sulfur, halogen, CN, CF 3 , phenyl, naphthanyl, phenyl pyridinyl, phenyl pyrimidinyl, phenyl imidazole, and Si(CH 3 ) 3 group. It is phenyl substituted or unsubstituted with one or more selected from the group consisting of;
a, b, and c are each independently 0 or 1, and 0 means that no bond exists;
d and e are each independently integers from 0 to 5, and when 0, it means a simple single bond;
m and n are each independently integers from 0 to 3, and m + n is 3 or less;
M is Ir or Pt or Os or Au or Co or C or Si or Ge;
X1 is carbon or nitrogen;
R2 and R3 are each independently adamantane, straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, thioalkyl with 1 to 30 carbon atoms, or cycloalkyl group with 3 to 30 carbon atoms,
Tritium, deuterium, hydrogen, adamantane, halogen, CN, CF 3 , straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, thioalkyl with 1 to 30 carbon atoms, cyclo with 3 to 30 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene substituted or unsubstituted with one or more selected from the group consisting of alkyl, phenyl, biphenyl, naphthyl, anthracenyl group, pyrenyl, triphenylene, and perylene. , perylene, phenylamine, biphenylamine, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyrrole. An aromatic hydrocarbon group having 6 to 50 carbon atoms that is substituted or unsubstituted with one or more selected from the group consisting of dinyl, phenylamine, biphenylamine, phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl and phenyl triazinyl groups, or
Tritium, deuterium, adamantane, halogen, CN, CF 3 , straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, thioalkyl with 1 to 30 carbon atoms, cycloalkyl with 3 to 30 carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, phenyl, substituted or unsubstituted with one or more selected from the group consisting of phenyl, biphenyl, naphthyl, anthracenyl group, pyrenyl, triphenylene, and perylene. rylene, 9,9-dimethylfluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyridinyl, Substituted or unsubstituted with one or more selected from the group consisting of phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl and phenyl triazinyl groups, and one selected from the group consisting of S, O, N, B, P and Si. It is a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms containing the above elements, or
Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, Phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene, phenyl, substituted or unsubstituted with one or more types selected from the group consisting of thioalkyl groups having 1 to 30 carbon atoms and cycloalkyl groups having 3 to 30 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl substituted with rylene group. , an amino group substituted with one or more types selected from the group consisting of pyrazinyl and pyrimidinyl groups;
R4, R5, R6, R7, R8, R9 and R10 are each independently selected from tritium, hydrogen, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , and having 1 to 20 carbon atoms. It is a straight-chain or branched-chain alkyl group, an alkoxyl group with 1 to 20 carbon atoms, a thioalkyl group with 1 to 20 carbon atoms, or a cycloalkyl group with 3 to 20 carbon atoms, or
Tritium, deuterium, hydrogen, adamantane, halogen, CN, CF 3 , straight or branched chain alkyl with 1 to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms, thioalkyl with 1 to 20 carbon atoms, cyclo with 3 to 20 carbon atoms Anthracenyl, phenanthrenyl, pyrenyl, triphenylene substituted or unsubstituted with one or more selected from the group consisting of alkyl, phenyl, biphenyl, naphthyl, anthracenyl group, pyrenyl, triphenylene, and perylene. , perylene, phenylamine, biphenylamine, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyrrole. An aromatic hydrocarbon group having 6 to 50 carbon atoms that is substituted or unsubstituted with one or more selected from the group consisting of dinyl, phenylamine, biphenylamine, phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl and phenyl triazinyl groups, or
Tritium, deuterium, adamantane, halogen, CN, CF 3 , straight or branched chain alkyl with 1 to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms, thioalkyl with 1 to 20 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, phenyl, substituted or unsubstituted with one or more selected from the group consisting of phenyl, biphenyl, naphthyl, anthracenyl group, pyrenyl, triphenylene and perylene. rylene, 9,9-dimethylfluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyridinyl, Substituted or unsubstituted with one or more selected from the group consisting of phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl and phenyl triazinyl groups, and one selected from the group consisting of S, O, N, B, P and Si. It is a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms containing the above elements, or
Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH 3 ) 3 , B(OH) 2 , straight or branched chain alkyl with 1 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, pyrenyl, triphenylene, and phenyl, substituted or unsubstituted with one or more types selected from the group consisting of thioalkyl groups having 1 to 30 carbon atoms, and cycloalkyl groups having 3 to 30 carbon atoms. Anthracenyl, phenanthrenyl, pyrenyl, triphenylene, perylene, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl substituted with rylene group. , an amino group substituted with one or more types selected from the group consisting of pyrazinyl and pyrimidinyl groups.
상기 유기화합물은 하기 화합물 1 내지 420 중의 어느 하나인 것을 특징으로 하는 유기화합물.
In claim 1,
The organic compound is any one of the following compounds 1 to 420.
상기 발광층이 청구항 1의 유기화합물을 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기전계발광소자.In an organic electroluminescent device in which an organic thin film layer consisting of one or multiple layers including at least a light-emitting layer is laminated between the cathode and the anode,
An organic electroluminescent device characterized in that the light-emitting layer contains the organic compound of claim 1 alone or in a combination of two or more types.
상기 발광층을 제외한 유기박막층이 청구항 1의 유기화합물을 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기전계발광소자.In an organic electroluminescent device in which an organic thin film layer consisting of one or multiple layers including at least a light-emitting layer is laminated between the cathode and the anode,
An organic electroluminescent device, characterized in that the organic thin film layer excluding the light-emitting layer contains the organic compound of claim 1 alone or in a combination of two or more types.
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