WO2017086729A1 - Organic electroluminescent compound, organic electroluminescent material and organic electroluminescent device comprising the same - Google Patents
Organic electroluminescent compound, organic electroluminescent material and organic electroluminescent device comprising the same Download PDFInfo
- Publication number
- WO2017086729A1 WO2017086729A1 PCT/KR2016/013314 KR2016013314W WO2017086729A1 WO 2017086729 A1 WO2017086729 A1 WO 2017086729A1 KR 2016013314 W KR2016013314 W KR 2016013314W WO 2017086729 A1 WO2017086729 A1 WO 2017086729A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- organic electroluminescent
- alkyl
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 189
- 239000000463 material Substances 0.000 title claims abstract description 92
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 42
- 239000000872 buffer Substances 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 125000005104 aryl silyl group Chemical group 0.000 claims description 26
- 125000001769 aryl amino group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 16
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 13
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000003367 polycyclic group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- 229910052796 boron Inorganic materials 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Chemical group 0.000 claims description 9
- 239000011593 sulfur Chemical group 0.000 claims description 9
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 229910052720 vanadium Inorganic materials 0.000 claims description 6
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 141
- 239000002019 doping agent Substances 0.000 description 33
- 238000002347 injection Methods 0.000 description 28
- 239000007924 injection Substances 0.000 description 28
- 230000005525 hole transport Effects 0.000 description 25
- 0 c(cc1)ccc1-c1ccc(*(c2ccccc2*2c3c-4cccc3)c(cccc3)c3-c3c2c-4ccc3)cc1 Chemical compound c(cc1)ccc1-c1ccc(*(c2ccccc2*2c3c-4cccc3)c(cccc3)c3-c3c2c-4ccc3)cc1 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000007740 vapor deposition Methods 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- -1 dibenzofuranyl Chemical group 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000004305 biphenyl Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 10
- 235000010290 biphenyl Nutrition 0.000 description 10
- 230000000903 blocking effect Effects 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 8
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 7
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 5
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 5
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 229910052741 iridium Inorganic materials 0.000 description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 125000004306 triazinyl group Chemical group 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 3
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 238000002061 vacuum sublimation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- MPEOPBCQHNWNFB-UHFFFAOYSA-N 1-chloro-2-iodobenzene Chemical compound ClC1=CC=CC=C1I MPEOPBCQHNWNFB-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 1
- JLGXRQBMJFAZRY-UHFFFAOYSA-N 2-(4-bromonaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=C(C2=CC=CC=C12)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 JLGXRQBMJFAZRY-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- ZGNCKIDXVHSMJL-UHFFFAOYSA-N 2-methylquinoline-8-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C)=CC=C21 ZGNCKIDXVHSMJL-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
- ZGFNHXQEPSZEQZ-UHFFFAOYSA-N 6,6-dichlorohexyl-[2-(2,6-dimethoxyphenyl)phenyl]phosphane Chemical group ClC(CCCCCPC1=C(C=CC=C1)C1=C(C=CC=C1OC)OC)Cl ZGFNHXQEPSZEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N Cc1ccccc1N Chemical compound Cc1ccccc1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/90—Multiple hosts in the emissive layer
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/166—Electron transporting layers comprising a multilayered structure
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
Definitions
- the present disclosure relates to an organic electroluminescent compound, an organic electroluminescent material and an organic electroluminescent device comprising the same.
- an electroluminescent device is a self-light-emitting display device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
- the first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
- Iridium(III) complexes have been widely known as phosphorescent light-emitting materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C-3’)iridium(acetylacetonate) [(acac)Ir(btp) 2 ], tris(2-phenylpyridine)iridium [Ir(ppy) 3 ] and bis(4,6-difluorophenylpyridinato-N,C2)picolinato iridium (Firpic) as red-, green- and blue-emitting materials, respectively.
- CBP 4,4’-N,N’-dicarbazol-biphenyl
- BCP bathocuproine
- BAlq aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate)
- the organic electroluminescent device may consist of a multi-layered structure in which a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., are comprised.
- a compound comprised for the hole transport layer is important to enhance characteristics of the device, such as efficiency for transporting holes to the light-emitting layer, luminous efficiency, and lifespan.
- CuPc copper phthalocyanine
- NPB 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
- TPD N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine
- MTDATA 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine
- an organic electroluminescent device optimizing the device is required as well as developing an organic electroluminescent material comprised in the device.
- studies have been made to improve the efficiency of an organic electroluminescent device by inserting an electron buffer layer between a light-emitting layer and an electron injection layer.
- the electron buffer layer is equipped to improve a problem of light-emitting luminance reduction which may occur due to the change of current properties in the device when the device is exposed to a high temperature during a process of producing panels.
- the properties of the compounds comprised for the electron buffer layer are important.
- the compound used for the electron buffer layer is desirable to perform a role of controlling an electron injection by the electron withdrawing characteristics and the electron affinity LUMO (lowest unoccupied molecular orbital) energy level, and thus may perform a role to improve the efficiency of the organic electroluminescent device.
- the development of an electron buffer material constituting an electron buffer layer is required in order to improve deterioration characteristics according to temperature of an organic electroluminescent device and improve the efficiency by controlling electron injection.
- Korean Patent Application Laid-Open No. 2015-0070827 discloses an organic electroluminescent device comprising a compound having a backbone in which arylamine moieties are respectively bonded to carbon positions 2 and 3 of a carbazole moiety and fused with each other to form an 8-membered ring.
- the above reference fails to disclose a compound having a structure in which two aryls bonded directly to carbon position 1 and the nitrogen atom of a carbazole moiety form an 8-membered ring via a nitrogen atom, an oxygen atom or a sulfur atom as a linker.
- the object of the present disclosure is firstly, to provide an organic electroluminescent compound effective to produce an organic electroluminescent device having low driving voltage and/or excellent luminous efficiency such as current and/or power efficiencies, secondly, to provide an organic electroluminescent material comprising the organic electroluminescent compound, and thirdly, to provide an organic electroluminescent device comprising the organic electroluminescent compound.
- Y represents S, O or NR 5 ;
- R 1 to R 5 each independently, represent deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C
- the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P;
- a, b and d each independently, represent an integer of 0 to 4
- c represents an integer of 0 to 3
- R 1 to R 4 may be the same or different
- the organic electroluminescent compound has the fused ring structure of an 8-membered ring based on a carbazole, and has a relatively high glass transition temperature as compared to low molecular weight.
- the compound of the present disclosure having a high glass transition temperature is excellent in thermal stability and can have morphological stability even at high temperatures during device operation.
- the compound of the present disclosure may be easily substituted due to the structural characteristics, and may be applied to various layers depending on the substituents.
- the organic electroluminescent compound of the present disclosure can provide an organic electroluminescent device having low driving voltage and/or excellent current and/or power efficiencies.
- an organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised of any layers constituting an organic electroluminescent device, if necessary.
- an organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound. If necessary, the organic electroluminescent material may be comprised of any layers constituting an organic electroluminescent device.
- the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
- Y represents S, O or NR 5 .
- R 1 to R 5 each independently, represent deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C
- R 1 to R 4 each independently, represent a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or a substituted or unsubstituted di(C6-C25)arylamino; or are linked to adjacent R 1 to R 4 , respectively, to form a substituted or unsubstituted, mono- or polycyclic, (C5-C25) aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
- R 1 to R 4 each independently, represent a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (5- to 20-membered)heteroaryl, or an unsubstituted di(C6-C25)arylamino; or are linked to adjacent R 1 to R 4 , respectively, to form an unsubstituted, mono- or polycyclic, (C5-C20) aromatic ring.
- R 1 to R 4 each independently, represent a substituted or unsubstituted phenyl, an unsubstituted biphenyl, an unsubstituted terphenyl, a carbazolyl substituted with a phenyl, an unsubstituted dibenzofuranyl, an unsubstituted dibenzothiophenyl, a quinoxalinyl substituted with a phenyl, a quinazolinyl substituted with a biphenyl, a pyridyl substituted with a dibiphenylamino, a triazinyl substituted with a diphenyl, or an unsubstituted dibiphenylamino; or are linked to adjacent R 1 to R 4 , respectively, to form a benzene ring.
- R 5 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 25-membered)heteroaryl. More preferably, R 5 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 18-membered)heteroaryl.
- R 5 represents a substituted or unsubstituted phenyl, an unsubstituted naphthylphenyl, an unsubstituted naphthyl, a biphenyl unsubstituted or substituted with a dibiphenylamino, an unsubstituted terphenyl, an unsubstituted quaterphenyl, an unsubstituted pentaphenyl, a fluorenyl substituted with a methyl or a phenyl, a carbazolyl substituted with a phenyl, an unsubstituted dibenzofuranyl, an unsubstituted dibenzothiophenyl, a triazinyl substituted with at least one phenyl, a quinoxalinyl substituted with a phenyl, a quinazolinyl substituted with a biphenyl, or a pyridyl substituted with a
- the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P, and preferably, at least one heteroatom selected from N, O and S.
- a, b and d each independently, represent an integer of 0 to 4
- c represents an integer of 0 to 3
- a to d each independently, represent an integer of 2 or more, each of R 1 to R 4 may be the same or different.
- a to d each independently, represent an integer of 0 to 2.
- the organic electroluminescent compound represented by formula 1 may be represented by any one of the following formulas 2 to 4:
- R 1 to R 5 , and a to d are as defined in formula 1.
- (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
- (C3-C30)cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
- (3- to 7- membered) heterocycloalkyl is a cycloalkyl having 3 to 7, preferably 5 to 7, ring backbone atoms, including at least one heteroatom selected from B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
- (C6-C30)aryl(ene) is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, may be partially saturated, and may comprise a spiro structure.
- the above aryl(ene) may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc.
- (3- to 30-membered)heteroaryl(ene) is an aryl having 3 to 30 ring backbone atoms, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P.
- the above heteroaryl(ene) may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); may comprise a spiro structure; and includes a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and a fused ring-type heteroaryl such as benzofur
- substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group, i.e. a substituent.
- the organic electroluminescent compound represented by formula 1 includes the following compounds, but is not limited thereto:
- organic electroluminescent compound of the present disclosure may be produced by a synthetic method known to a person skilled in the art, for example, the following reaction schemes:
- R 1 to R 4 are as defined in formula 1.
- the organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes.
- One of the first and second electrodes may be an anode, and the other may be a cathode.
- the organic layer may comprise at least one light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
- the hole auxiliary layer or the light-emitting auxiliary layer may be placed between the hole transport layer and the light-emitting layer, which may control a transport rate of a hole.
- the hole auxiliary layer or the light-emitting auxiliary layer may be effective to produce an organic electroluminescent device having excellent efficiencies and/or improved lifespan.
- the electron buffer layer may be composed of two or more layers in order to control the electron injection and improve characteristics of interface between the light-emitting layer and the electron injection layer. Each of the layers may comprise two or more compounds.
- the hole blocking layer or electron transport layer may be composed of two or more layers, and each of the layers may comprise two or more compounds.
- the present disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound represented by formula 1.
- the organic electroluminescent material may consist of the organic electroluminescent compound represented by formula 1 as a sole compound, or may further comprise conventional materials generally used in organic electroluminescent materials.
- the organic electroluminescent material may comprise the compound represented by formula 1, the compound represented by formula 5, or both of them.
- the organic electroluminescent material may be a host material, a hole transport material, or an electron buffer material, and preferably, a host material or an electron buffer material, but is not limited thereto.
- the compound represented by formula 1 may be comprised in an organic electroluminescent device as an electron buffer material.
- the electron buffer material may comprise the compound represented by formula 1.
- the electron buffer material may control flow properties of an electron.
- the electron buffer material may trap an electron, block an electron, or lower an energy barrier between an electron transport zone and a light-emitting layer.
- the electron buffer material may be an electron buffer material of an organic electroluminescent device.
- the electron buffer material in an organic electroluminescent device may be used for an electron buffer layer, or may also be simultaneously used for other zones such as an electron transport layer, an electron injection layer or a light-emitting layer.
- the electron buffer material may be a mixture or a composition further comprising conventional materials generally used in producing an organic electroluminescent device.
- the compound represented by formula 1 may be comprised in an organic electroluminescent device as a host material.
- the host material may comprise the compound represented by formula 1.
- the host material may comprise at least one of a first host compound and at least one of a second host compound.
- the weight ratio of the first host compound to the second host compound is in the range of 1:99 to 99:1.
- the second host compound may be any of the known phosphorescent hosts. It is prefeble to use the compound represented by the following formula 5 in terms of driving voltage, luminous efficiency and/or power efficiency.
- the first host compound may comprise the compound represented by formula 1
- the second host compound may comprise the compound represented by the following formula 5.
- the organic electroluminescent material may comprise the organic electroluminescent compound represented by formula 1 and the compound represented by the following formula 5:
- Ma represents a substituted or unsubstituted nitrogen-containing (5- to 30-membered)heteroaryl; preferably, a substituted or unsubstituted nitrogen-containing (5- to 25-membered)heteroaryl; and more preferably, a substituted or unsubstituted nitrogen-containing (5- to 18-membered)heteroaryl.
- Ma may represent a substituted triazinyl, a substituted pyrimidinyl, a substituted benzimidazolyl, a substituted quinoxalinyl, a substituted quinolyl, a substituted quinazolinyl, or an unsubstituted naphthyridinyl; and the substituents of the substituted nitrogen-containing (5- to 30-membered)heteroaryl may be a phenyl unsubstituted or substituted with a dibenzothiophenyl, a tert-butyl or a cyano; an unsubstituted biphenyl; an unsubstituted terphenyl; an unsubstituted naphthyl; an unsubstitued dibenzothiophenyl; or a carbazolyl substituted with a phenyl.
- La represents a single bond, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C6-C30)arylene; preferably, a single bond, a substituted or unsubstituted (3- to 25-membered)heteroarylene, or a substituted or unsubstituted (C6-C25)arylene; more preferably, a single bond, an unsubstituted (5- to 18-membered)heteroarylene or an unsubstituted (C6-C18)arylene; and for example, a single bond, an unsubstituted phenylene, an unsubstituted biphenylene, an unsubstituted naphthylene, or an unsubstituted pyridinylene.
- one of V and W represents a single bond, and the other of V and W represents any one of NR 6 , CR 7 R 8 , S and O.
- one of V and W represents a single bond, and the other of V and W represents any one of NR 6 , S and O.
- Xa to Xi each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a
- Xa to Xi each independently, represent hydrogen, a cyano, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 25-membered)heteroaryl, or a substituted or unsubstituted tri(C6-C25)arylsilyl. More preferably, Xa to Xi, each independently, represent hydrogen, an unsubstituted (C6-C18)aryl, or (6- to 18-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl.
- Xa to Xi each independently, may represent hydrogen, an unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, or a carbazolyl substituted with a phenyl.
- R 6 to R 8 each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; and preferably, a substituted or unsubstituted (C6-C25)aryl; more preferably, an unsubstituted (C6-C18)aryl; and for example, an unsubstituted phen
- the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P, and preferably, N.
- the organic electroluminescent compound represented by formula 5 includes the following compounds, but is not limited thereto:
- the compound represented by formula 5 of the present disclosure may be produced by a synthetic method known to a person skilled in the art, in particular, a synthetic method disclosed in numerous patent publications.
- compounds B-1 and B-15 which are well-known materials, may be synthesized by the method disclosed in the following Patent Application Laid-Open, but are not limited thereto.
- the synthesis methods of compound B-1 and the derivatives thereof are disclosed in Korean Patent Application Laid-Open No. 2016-0010333, published on January 27, 2016.
- the synthesis methods of compound B-15 and the derivatives thereof are disclosed in Korean Patent Application Laid-Open No. 2013-0011446, published on January 30, 2013.
- the dopant comprised in the organic electroluminescent device of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably at least one phosphorescent dopant.
- the phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particulary limited, but may be preferably selected from the metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
- the dopant comprised in the organic electroluminescent device of the present disclosure may comprise a compound selected from the group consisting of the compounds represented by the following formulas 101 to 103.
- L is selected from the following structures:
- R 100 represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
- R 101 to R 109 and R 111 to R 123 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, or a substituted or unsubstituted (C1-C30)alkoxy;
- R 106 to R 109 may be linked to adjacent R 106 to R 109 , respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl; and R 120 to R 123 may be linked to
- R 124 to R 127 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; and R 124 to R 127 may be linked to adjacent R 124 to R 127 , respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
- R 201 to R 211 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; and R 208 to R 211 may be linked to adjacent R 208 to R 211 , respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
- f and g each independently, represent an integer of 1 to 3; where if f or g is an integer of 2 or more, each R 100 may be the same or different; and
- n an integer of 1 to 3.
- the organic electroluminescent device of the present disclosure may comprise the compound of formula 1, and further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds, simultaneously.
- At least one layer of the emitting-layer in the organic electroluminescent device of the present disclosure may comprise at least one dopant compound and at least one host compound, wherein the host compound may be the compound represented by formula 1.
- an electron buffer layer of the organic electroluminescent device may comprise the compound represented by formula 1.
- At least one layer of the light-emitting layer in the organic electroluminescent device of the present disclosure may comprise at least one dopant compound and at least two host compounds, wherein the first host compound in the host compounds may be the compound represented by formula 1, and wherein the second host compound in the host compounds may be the compound represented by formula 5.
- an electron buffer layer of the organic electroluminescent device may comprise the compound represented by formula 1.
- the organic layer may comprise at least one organic electroluminescent compound represented by formula 1. Also, the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides, and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
- the organic layer may further comprise one or more additional light-emitting layers and a charge generating layer.
- the organic electroluminescent device of the present disclosure may emit white light by further comprising at least one light-emitting layer, which comprises a blue, red, or green electroluminescent compound known in the field, besides the compound of the present disclosure. If necessary, it may further comprise a yellow or orange light-emitting layer.
- a surface layer may be placed on an inner surface(s) of one or both electrode(s), selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer.
- a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
- a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
- the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
- the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
- the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
- the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
- the oxidative dopant includes various Lewis acids and acceptor compounds
- the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a reductive dopant layer may be employed as a charge generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.
- dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc.
- wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc., can be used, but are not limited thereto.
- a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
- the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
- An OLED device was produced by using the organic electroluminescent compound according to the present disclosure.
- a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
- the ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus.
- Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr.
- compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
- Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
- Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 30 nm on the first hole transport layer.
- a light-emitting layer was formed thereon as follows: Compound C-7 and compound B-51 were introduced into two cells of the vacuum vapor depositing apparatus, respectively, as a host, and compound D-1 was introduced into another cell as a dopant.
- the two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
- Compound ET-1 and compound EI-1 were then introduced into another two cells, and respectively evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
- an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus.
- an OLED device was produced.
- Each of the materials used for producing the OLED device was purified by vacuum sublimation at 10 -6 torr.
- Comparative Example 1-1 Producing an OLED device comprising a second
- An OLED device was produced in the same manner as in Device Example 1-1, except that only compound B-51 was used as a host for a light-emitting layer.
- Comparative Example 1-2 Producing an OLED device comprising a
- An OLED device was produced in the same manner as in Device Example 1-1, except for the following: A light-emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by using compound CBP as a host and compound D-1 as a dopant; compound Balq was deposited as a hole blocking layer having a thickness of 10 nm; and thereafter, compound ET-1 and compound EI-1 were introduced into another two cells, and evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 25 nm on the light-emitting layer.
- the driving voltage, the luminous efficiency, the power efficiency, and the CIE color coordinate at a luminance of 1,000 nits of the OLED devices produced in Device Example 1-1, and Comparative Examples 1-1 and 1-2 are provided in Table 1 below.
- An OLED device was produced in the same manner as in Device Examples 1-1, except for using compound D-13 as a dopant, and using the first and second host compounds shown in Table 2 below as a host.
- Comparative Example 2-1 Producing an OLED device comprising a second
- An OLED device was produced in the same manner as in Device Examples 2-1, except that only compound B-51 was used as a host for a light-emitting layer.
- Comparative Example 2-2 Producing an OLED device comprising a
- An OLED device was produced in the same manner as in Device Example 2-1, except for the following: A light-emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by using compound CBP as a host and compound D-13 as a dopant; compound Balq was deposited as a hole blocking layer having a thickness of 10 nm; and thereafter, compound ET-1 and compound EI-1 were introduced into another two cells, and evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 25 nm on the light-emitting layer.
- the driving voltage, the luminous efficiency, the power efficiency, and the CIE color coordinate at a luminance of 1,000 nits of the OLED devices produced in Device Example 2-1, and Comparative Examples 2-1 and 2-2 are provided in Table 2 below.
- An OLED device was produced in the same manner as in Device Example 1-1, except for the following: Compound C-91 was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-13 was introduced into another cell as a dopant. The dopant was evaporated at a different rate from the host compound, so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
- Comparative Example 3-1 Producing an OLED device comprising a
- An OLED device was produced in the same manner as in Device Example 3-1, except for the following: A light-emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by using compound CBP as a host and compound D-13 as a dopant; compound Balq was deposited as a hole blocking layer having a thickness of 10 nm; and thereafter, compound ET-1 and compound EI-1 were introduced into another two cells, and evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 25 nm on the light-emitting layer.
- the driving voltage, the luminous efficiency, the power efficiency, and the CIE color coordinate at a luminance of 1,000 nits of the OLED devices produced in Device Example 3-1 and Comparative Example 3-1 are provided in Table 3 below.
- An OLED device was produced in the same manner as in Device Example 1-1, except for the following: Compound C-91 was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-74 was introduced into another cell as a dopant. The dopant was evaporated at a different rate from the host compound, so that the dopant was deposited in a doping amount of 10 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
- Comparative Example 4-1 Producing an OLED device comprising a
- An OLED device was produced in the same manner as in Device Example 4-1, except for the following: A light-emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by using compound CBP as a host and compound D-74 as a dopant; compound Balq was deposited as a hole blocking layer having a thickness of 10 nm; and thereafter, compound ET-1 and compound EI-1 were introduced into another two cells, and evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 25 nm on the light-emitting layer.
- the driving voltage, the luminous efficiency, the power efficiency, and the CIE color coordinate based on 10 mA/cm 2 of the OLED devices produced in Device Example 4-1 and Comparative Example 4-1 are provided in Table 4 below.
- the OLED device comprising the compound of the present disclosure as a host not only has excellent luminance property, but also improved power consumption by lowering the driving voltage and increasing luminous and power efficiencies, compared to the OLED device using conventional luminescent material.
- Comparative Example 5-1 Producing a blue light-emitting OLED device
- An OLED device was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to 10 -7 torr.
- ITO transparent electrode indium tin oxide
- Compound HT-3 was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming the second hole transport layer having a thickness of 5 nm on the first hole transport layer.
- a light-emitting layer was then deposited as follows.
- Compound BH-1 as a host was introduced into one cell of the vacuum vapor deposition apparatus and compound BD-1 as a dopant was introduced into another cell of the apparatus.
- the two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 2 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 20 nm on the second hole transport layer.
- compound ET-2 as an electron transport material was introduced into one cell of the vacuum vapor deposition apparatus, and compound EI-1 was introduced into another cell of the vacuum vapor deposition apparatus.
- the two materials were evaporated at the same rate and doped in a doping amount of 50 wt%, respectively, to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
- an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
- All the materials used for producing the OLED device were purified by vacuum sublimation at 10 -6 torr.
- An OLED device was produced in the same manner as in Comparative Example 5-1, except that the thickness of an electron transport layer was reduced to 25 nm and an electron buffer layer having a thickness of 5 nm was inserted between the light-emitting layer and the electron transport layer.
- the driving voltage, the luminous efficiency, and the CIE color coordinate at a luminance of 1,000 nits of the OLED devices produced in Comparative Example 5-1 and Device Examples 5-1 and 5-2 are provided in Table 5 below.
- the OLED device comprising the compound of the present disclosure as an electron buffer material improves the power consumption by lowering the driving voltage and increasing luminous efficiency, compared to the OLED device not comprising an electron buffer material.
Abstract
The present disclosure relates to an organic electroluminescent compound, an organic electroluminescent material, and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound of the present disclosure, it is possible to provide an organic electroluminescent device having low driving voltage, and/or excellent current and/or power efficiencies.
Description
The present disclosure relates to an organic electroluminescent compound, an organic electroluminescent material and an organic electroluminescent device comprising the same.
Among display devices, an electroluminescent device (EL device) is a self-light-emitting display device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. The first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
The most important factor determining luminous efficiency in an organic electroluminescent device is light-emitting materials. Until now, fluorescent materials have been widely used as the light-emitting material. However, in view of electroluminescent mechanisms, since phosphorescent light-emitting materials theoretically enhance luminous efficiency by four (4) times compared to fluorescent light-emitting materials, phosphorescent light-emitting materials have been widely researched. Iridium(III) complexes have been widely known as phosphorescent light-emitting materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C-3’)iridium(acetylacetonate) [(acac)Ir(btp)2], tris(2-phenylpyridine)iridium [Ir(ppy)3] and bis(4,6-difluorophenylpyridinato-N,C2)picolinato iridium (Firpic) as red-, green- and blue-emitting materials, respectively.
In conventional technology, 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Recently, Pioneer (Japan) et al., developed a high performance organic electroluminescent device using bathocuproine (BCP) and aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate) (BAlq), etc., as host materials, which were known as hole blocking materials.
Although these materials provide good luminous characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum, and the lifespan of the device may be shortened. (2) The power efficiency of the organic electroluminescent device is given by [(π/voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage. Although the organic electroluminescent device comprising phosphorescent host materials provides higher current efficiency (cd/A) than one comprising fluorescent materials, a significantly high driving voltage is necessary. Thus, there is no merit in terms of power efficiency (lm/W). (3) Also, the operational lifespan of the organic electroluminescent device is short, and luminous efficiency is still necessary to improve. Accordingly, the materials constituting the organic layer in the device, in particular a host constituting the light-emitting material, must be selected appropriately in order to realize the excellent characteristics of the organic EL device.
To improve efficiencies and stability, the organic electroluminescent device may consist of a multi-layered structure in which a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., are comprised. In the structure, a compound comprised for the hole transport layer is important to enhance characteristics of the device, such as efficiency for transporting holes to the light-emitting layer, luminous efficiency, and lifespan.
In this regard, copper phthalocyanine (CuPc), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), etc., were used as hole injection and transport materials for an organic electroluminescent device. However, the organic electroluminescent device using these materials is problematic in lowering quantum efficiency and lifespan. It is due to thermal stress occuring between an anode and a hole injection layer, when the organic electroluminescent device is driven under high current. Thermal stress significantly reduces the lifespan of the device. Furthermore, since the organic material used for the hole injection layer has very high hole mobility, the hole-electron charge balance may be broken and quantum yield (cd/A) may decrease. Thus, development of a hole transport layer for improving the durability of an organic electroluminescent device is still required.
Meanwhile, in order to improve the efficienty of an organic electroluminescent device, optimizing the device is required as well as developing an organic electroluminescent material comprised in the device. Thus, studies have been made to improve the efficiency of an organic electroluminescent device by inserting an electron buffer layer between a light-emitting layer and an electron injection layer. The electron buffer layer is equipped to improve a problem of light-emitting luminance reduction which may occur due to the change of current properties in the device when the device is exposed to a high temperature during a process of producing panels. Thus, the properties of the compounds comprised for the electron buffer layer are important. In addition, the compound used for the the electron buffer layer is desirable to perform a role of controlling an electron injection by the electron withdrawing characteristics and the electron affinity LUMO (lowest unoccupied molecular orbital) energy level, and thus may perform a role to improve the efficiency of the organic electroluminescent device. Thus, the development of an electron buffer material constituting an electron buffer layer is required in order to improve deterioration characteristics according to temperature of an organic electroluminescent device and improve the efficiency by controlling electron injection.
Korean Patent Application Laid-Open No. 2015-0070827 discloses an organic electroluminescent device comprising a compound having a backbone in which arylamine moieties are respectively bonded to carbon positions 2 and 3 of a carbazole moiety and fused with each other to form an 8-membered ring. However, the above reference fails to disclose a compound having a structure in which two aryls bonded directly to carbon position 1 and the nitrogen atom of a carbazole moiety form an 8-membered ring via a nitrogen atom, an oxygen atom or a sulfur atom as a linker.
The object of the present disclosure is firstly, to provide an organic electroluminescent compound effective to produce an organic electroluminescent device having low driving voltage and/or excellent luminous efficiency such as current and/or power efficiencies, secondly, to provide an organic electroluminescent material comprising the organic electroluminescent compound, and thirdly, to provide an organic electroluminescent device comprising the organic electroluminescent compound.
As a result of intensive studies to solve the technical problem above, the present inventors found that the above objective can be achieved by an organic electroluminescent compound represented by the following formula 1:
wherein
Y represents S, O or NR5;
R1 to R5, each independently, represent deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or are linked to adjacent R1 to R5 to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P;
a, b and d, each independently, represent an integer of 0 to 4, c represents an integer of 0 to 3; where if a to d, each independently, represent an integer of 2 or more, each of R1 to R4 may be the same or different; and
with the proviso, when Y represents NR5 and a represents 2, two R1 are not fused with the aryl ring to which they are attached to form a carbazole ring.
The organic electroluminescent compound has the fused ring structure of an 8-membered ring based on a carbazole, and has a relatively high glass transition temperature as compared to low molecular weight. The compound of the present disclosure having a high glass transition temperature is excellent in thermal stability and can have morphological stability even at high temperatures during device operation. In addition, the compound of the present disclosure may be easily substituted due to the structural characteristics, and may be applied to various layers depending on the substituents.
The organic electroluminescent compound of the present disclosure can provide an organic electroluminescent device having low driving voltage and/or excellent current and/or power efficiencies.
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the disclosure, and is not meant in any way to restrict the scope of the disclosure.
The term “an organic electroluminescent compound” in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised of any layers constituting an organic electroluminescent device, if necessary.
The term “an organic electroluminescent material” in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound. If necessary, the organic electroluminescent material may be comprised of any layers constituting an organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
The compound represented by formula 1 will be described in detail as follows.
In formula 1, Y represents S, O or NR5.
In formula 1, R1 to R5, each independently, represent deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or are linked to adjacent R1 to R5 to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or a combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur. With the proviso, when Y represents NR5 and a represnets 2, two R1 are not fused with the aryl ring to which they are attached to form a carbazole ring.
Preferably, R1 to R4, each independently, represent a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or a substituted or unsubstituted di(C6-C25)arylamino; or are linked to adjacent R1 to R4, respectively, to form a substituted or unsubstituted, mono- or polycyclic, (C5-C25) aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur. More preferably, R1 to R4, each independently, represent a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (5- to 20-membered)heteroaryl, or an unsubstituted di(C6-C25)arylamino; or are linked to adjacent R1 to R4, respectively, to form an unsubstituted, mono- or polycyclic, (C5-C20) aromatic ring. For example, R1 to R4, each independently, represent a substituted or unsubstituted phenyl, an unsubstituted biphenyl, an unsubstituted terphenyl, a carbazolyl substituted with a phenyl, an unsubstituted dibenzofuranyl, an unsubstituted dibenzothiophenyl, a quinoxalinyl substituted with a phenyl, a quinazolinyl substituted with a biphenyl, a pyridyl substituted with a dibiphenylamino, a triazinyl substituted with a diphenyl, or an unsubstituted dibiphenylamino; or are linked to adjacent R1 to R4, respectively, to form a benzene ring.
Preferably, R5 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 25-membered)heteroaryl. More preferably, R5 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 18-membered)heteroaryl. For example, R5 represents a substituted or unsubstituted phenyl, an unsubstituted naphthylphenyl, an unsubstituted naphthyl, a biphenyl unsubstituted or substituted with a dibiphenylamino, an unsubstituted terphenyl, an unsubstituted quaterphenyl, an unsubstituted pentaphenyl, a fluorenyl substituted with a methyl or a phenyl, a carbazolyl substituted with a phenyl, an unsubstituted dibenzofuranyl, an unsubstituted dibenzothiophenyl, a triazinyl substituted with at least one phenyl, a quinoxalinyl substituted with a phenyl, a quinazolinyl substituted with a biphenyl, or a pyridyl substituted with a dibiphenylamino.
In formula 1, the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P, and preferably, at least one heteroatom selected from N, O and S.
In formula 1, a, b and d, each independently, represent an integer of 0 to 4, c represents an integer of 0 to 3; where if a to d, each independently, represent an integer of 2 or more, each of R1 to R4 may be the same or different. Preferably, a to d, each independently, represent an integer of 0 to 2.
The organic electroluminescent compound represented by formula 1 may be represented by any one of the following formulas 2 to 4:
wherein, R1 to R5, and a to d are as defined in formula 1.
In formula 2, when a represents 2, two R1 are not fused with the aryl ring to which they are attached to form a carbazole ring.
Herein, the term “(C1-C30)alkyl” is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. The term “(C3-C30)cycloalkyl” is a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term “(3- to 7- membered) heterocycloalkyl” is a cycloalkyl having 3 to 7, preferably 5 to 7, ring backbone atoms, including at least one heteroatom selected from B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. The term “(C6-C30)aryl(ene)” is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, may be partially saturated, and may comprise a spiro structure. The above aryl(ene) may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc. The term “(3- to 30-membered)heteroaryl(ene)” is an aryl having 3 to 30 ring backbone atoms, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The above heteroaryl(ene) may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); may comprise a spiro structure; and includes a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, benzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, and dihydroacridinyl. Furthermore, “halogen” includes F, Cl, Br, and I.
Herein, “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group, i.e. a substituent. The substituents of the substituted (C1-C30)alkyl, the substituted (C2-C30)alkenyl, the substituted (C2-C30)alkynyl, the substituted (C6-C30)aryl(ene), the substituted (3- to 30-membered)heteroaryl(ene), the substituted (C3-C30)cycloalkyl, the substituted (C3-C30)cycloalkenyl, the substituted (3- to 7-membered)heterocycloalkyl, the substituted (C1-C30)alkoxy, the substituted tri(C1-C30)alkylsilyl, the substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the substituted tri(C6-C30)arylsilyl, the substituted mono- or di- (C1-C30)alkylamino, the substituted mono- or di- (C6-C30)arylamino, the substituted (C1-C30)alkyl(C6-C30)arylamino, and the substituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or the combination thereof, in R1 to R8, Ma, La and Xa to Xi, each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (5- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl; a (C6-C30)aryl unsubstituted or substituted with a (5- to 30-membered)heteroaryl; a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di- (C1-C30)alkylamino; a mono- or di- (C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl; preferably, are at least one selected from the group consisting of a (C1-C20)alkyl, a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C20)aryl, a substituted or unsubstituted (C6-C20)aryl, and a di(C6-C20)arylamino unsubstituted or substituted with a (C1-C20)alkyl; more preferably, are at least one selected from the group consisting of a (C1-C10)alkyl, a (6- to 18-membered)heteroaryl unsubstituted or substituted with a (C6-C10)aryl, a substituted or unsubstituted (C6-C18)aryl, and a di(C6-C18)arylamino unsubstituted or substituted with a (C1-C10)alkyl; and for example, may be at least one selected from the group consisting of a methyl; a phenyl unsubstituted or substituted with a dibenzothiophenyl, a tert-butyl or a cyano; an unsubstituted biphenyl; an unsubstituted terphenyl; an unsubstituted naphthyl; a quinoxalinyl substituted with a phenyl; a triazinyl substituted with at least one phenyl; a pyrimidinyl substituted with at least one phenyl; an unsubstituted dibenzothiophenyl; a carbazolyl substituted with a phenyl; a dibiphenylamino; a phenylbiphenylamino; and a fluorenylbiphenylamino substituted with a dimethyl.
The organic electroluminescent compound represented by formula 1 includes the following compounds, but is not limited thereto:
The organic electroluminescent compound of the present disclosure may be produced by a synthetic method known to a person skilled in the art, for example, the following reaction schemes:
[Reaction Scheme 1]
wherein, R1 to R4 are as defined in formula 1.
The organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes. One of the first and second electrodes may be an anode, and the other may be a cathode. The organic layer may comprise at least one light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer. Herein, the hole auxiliary layer or the light-emitting auxiliary layer may be placed between the hole transport layer and the light-emitting layer, which may control a transport rate of a hole. The hole auxiliary layer or the light-emitting auxiliary layer may be effective to produce an organic electroluminescent device having excellent efficiencies and/or improved lifespan. The electron buffer layer may be composed of two or more layers in order to control the electron injection and improve characteristics of interface between the light-emitting layer and the electron injection layer. Each of the layers may comprise two or more compounds. The hole blocking layer or electron transport layer may be composed of two or more layers, and each of the layers may comprise two or more compounds.
According to one embodiment of the present disclosure, the present disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound represented by formula 1. The organic electroluminescent material may consist of the organic electroluminescent compound represented by formula 1 as a sole compound, or may further comprise conventional materials generally used in organic electroluminescent materials. Preferably, the organic electroluminescent material may comprise the compound represented by formula 1, the compound represented by formula 5, or both of them. The organic electroluminescent material may be a host material, a hole transport material, or an electron buffer material, and preferably, a host material or an electron buffer material, but is not limited thereto.
According to one embodiment of the present disclosure, the compound represented by formula 1 may be comprised in an organic electroluminescent device as an electron buffer material. In other words, the electron buffer material may comprise the compound represented by formula 1. The electron buffer material may control flow properties of an electron. For example, the electron buffer material may trap an electron, block an electron, or lower an energy barrier between an electron transport zone and a light-emitting layer. Specifically, the electron buffer material may be an electron buffer material of an organic electroluminescent device. The electron buffer material in an organic electroluminescent device may be used for an electron buffer layer, or may also be simultaneously used for other zones such as an electron transport layer, an electron injection layer or a light-emitting layer. The electron buffer material may be a mixture or a composition further comprising conventional materials generally used in producing an organic electroluminescent device.
According to one embodiment of the present disclosure, the compound represented by formula 1 may be comprised in an organic electroluminescent device as a host material. In other words, the host material may comprise the compound represented by formula 1. Also, the host material may comprise at least one of a first host compound and at least one of a second host compound. Herein, the weight ratio of the first host compound to the second host compound is in the range of 1:99 to 99:1. The second host compound may be any of the known phosphorescent hosts. It is prefeble to use the compound represented by the following formula 5 in terms of driving voltage, luminous efficiency and/or power efficiency. In the host material of the present disclosure, the first host compound may comprise the compound represented by formula 1, and the second host compound may comprise the compound represented by the following formula 5.
The organic electroluminescent material may comprise the organic electroluminescent compound represented by formula 1 and the compound represented by the following formula 5:
In formula 5, Ma represents a substituted or unsubstituted nitrogen-containing (5- to 30-membered)heteroaryl; preferably, a substituted or unsubstituted nitrogen-containing (5- to 25-membered)heteroaryl; and more preferably, a substituted or unsubstituted nitrogen-containing (5- to 18-membered)heteroaryl. For example, Ma may represent a substituted triazinyl, a substituted pyrimidinyl, a substituted benzimidazolyl, a substituted quinoxalinyl, a substituted quinolyl, a substituted quinazolinyl, or an unsubstituted naphthyridinyl; and the substituents of the substituted nitrogen-containing (5- to 30-membered)heteroaryl may be a phenyl unsubstituted or substituted with a dibenzothiophenyl, a tert-butyl or a cyano; an unsubstituted biphenyl; an unsubstituted terphenyl; an unsubstituted naphthyl; an unsubstitued dibenzothiophenyl; or a carbazolyl substituted with a phenyl.
In formula 5, La represents a single bond, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C6-C30)arylene; preferably, a single bond, a substituted or unsubstituted (3- to 25-membered)heteroarylene, or a substituted or unsubstituted (C6-C25)arylene; more preferably, a single bond, an unsubstituted (5- to 18-membered)heteroarylene or an unsubstituted (C6-C18)arylene; and for example, a single bond, an unsubstituted phenylene, an unsubstituted biphenylene, an unsubstituted naphthylene, or an unsubstituted pyridinylene.
In formula 5, one of V and W represents a single bond, and the other of V and W represents any one of NR6, CR7R8, S and O. Preferably, one of V and W represents a single bond, and the other of V and W represents any one of NR6, S and O.
In formula 5, Xa to Xi, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to adjacent Xa to Xi, respectively, to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur. Preferably, Xa to Xi, each independently, represent hydrogen, a cyano, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 25-membered)heteroaryl, or a substituted or unsubstituted tri(C6-C25)arylsilyl. More preferably, Xa to Xi, each independently, represent hydrogen, an unsubstituted (C6-C18)aryl, or (6- to 18-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl. For example, Xa to Xi, each independently, may represent hydrogen, an unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, or a carbazolyl substituted with a phenyl.
In formula 5, R6 to R8, each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; and preferably, a substituted or unsubstituted (C6-C25)aryl; more preferably, an unsubstituted (C6-C18)aryl; and for example, an unsubstituted phenyl, an unsubstituted naphthyl, or an unsubstituted biphenyl.
In formula 5, the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P, and preferably, N.
The organic electroluminescent compound represented by formula 5 includes the following compounds, but is not limited thereto:
The compound represented by formula 5 of the present disclosure may be produced by a synthetic method known to a person skilled in the art, in particular, a synthetic method disclosed in numerous patent publications. For example, compounds B-1 and B-15, which are well-known materials, may be synthesized by the method disclosed in the following Patent Application Laid-Open, but are not limited thereto. Specifically, the synthesis methods of compound B-1 and the derivatives thereof are disclosed in Korean Patent Application Laid-Open No. 2016-0010333, published on January 27, 2016. Also, the synthesis methods of compound B-15 and the derivatives thereof are disclosed in Korean Patent Application Laid-Open No. 2013-0011446, published on January 30, 2013.
The dopant comprised in the organic electroluminescent device of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably at least one phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particulary limited, but may be preferably selected from the metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
The dopant comprised in the organic electroluminescent device of the present disclosure may comprise a compound selected from the group consisting of the compounds represented by the following formulas 101 to 103.
wherein, L is selected from the following structures:
R100 represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
R101 to R109 and R111 to R123, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, or a substituted or unsubstituted (C1-C30)alkoxy; R106 to R109 may be linked to adjacent R106 to R109, respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl; and R120 to R123 may be linked to adjacent R120 to R123, respectively, to form a substituted or unsubstituted fused ring, e.g., a quinoline unsubstituted or substituted with an alkyl or an aryl;
R124 to R127, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; and R124 to R127 may be linked to adjacent R124 to R127, respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
R201 to R211, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; and R208 to R211 may be linked to adjacent R208 to R211, respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
f and g, each independently, represent an integer of 1 to 3; where if f or g is an integer of 2 or more, each R100 may be the same or different; and
n represents an integer of 1 to 3.
The specific examples of the compound used as a dopant are as follows:
The organic electroluminescent device of the present disclosure may comprise the compound of formula 1, and further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds, simultaneously.
According to one embodiment of the present disclosure, at least one layer of the emitting-layer in the organic electroluminescent device of the present disclosure may comprise at least one dopant compound and at least one host compound, wherein the host compound may be the compound represented by formula 1. Also, an electron buffer layer of the organic electroluminescent device may comprise the compound represented by formula 1.
According to one embodiment of the present disclosure, at least one layer of the light-emitting layer in the organic electroluminescent device of the present disclosure may comprise at least one dopant compound and at least two host compounds, wherein the first host compound in the host compounds may be the compound represented by formula 1, and wherein the second host compound in the host compounds may be the compound represented by formula 5. Also, an electron buffer layer of the organic electroluminescent device may comprise the compound represented by formula 1.
In the organic electroluminescent device of the present disclosure, the organic layer may comprise at least one organic electroluminescent compound represented by formula 1. Also, the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides, and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal. The organic layer may further comprise one or more additional light-emitting layers and a charge generating layer.
In addition, the organic electroluminescent device of the present disclosure may emit white light by further comprising at least one light-emitting layer, which comprises a blue, red, or green electroluminescent compound known in the field, besides the compound of the present disclosure. If necessary, it may further comprise a yellow or orange light-emitting layer.
In the organic electroluminescent device of the present disclosure, preferably, at least one layer (hereinafter, "a surface layer”) may be placed on an inner surface(s) of one or both electrode(s), selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer. Specifically, a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer. Such a surface layer provides operation stability for the organic electroluminescent device. Preferably, the chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. A reductive dopant layer may be employed as a charge generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.
In order to form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc., can be used, but are not limited thereto.
When using a wet film-forming method, a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
Hereinafter, the preparation method of the compounds of the present disclosure, and the properties of the device comprising the compounds will be explained in detail with reference to the representative compounds of the present disclosure. However, the present disclosure is not limited by the following examples.
Example 1: Preparation of compound C-73
1) Preparation of compound
1-1
After introducing 20 g of compound A (81.2 mmol), 26.8 g of bis(pinacolato)diborane (105 mmol), 2.8 g of bis(triphenylphosphine)palladium(II) dichloride (4 mmol), 16 g of potassium acetate (162 mmol), and 400 mL of 1,4-dioxane into a reaction vessel, the mixture was stirred overnight at 140℃. After completion of the reaction, the reaction product was cooled to room temperature, and then was extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. Thereafter, the resulting product was purified by column chromatography to obtain 15.4 g of compound 1-1 (77 %).
2) Preparation of compound
1-2
After introducing 14 g of compound 1-1 (56.6 mmol), 6.1 mL of 2-bromoaniline (54 mmol), 2.6 g of tetrakis(triphenylphosphine)palladium (2.3 mmol), 19.6 g of potassium carbonate (142 mmol), 280 mL of toluene, 70 mL of ethanol, and 70 mL of distilled water into a reaction vessel, the mixture was stirred for 5 hours at 120℃. After completion of the reaction, the reaction product was cooled to room temperature, and then was extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. Thereafter, the resulting product was purified by column chromatography to obtain 8.6 g of compound 1-2 (59 %).
3) Preparation of compound
1-3
After introducing 8.3 g of compound 1-2 (32 mmol), 4.3 mL of 1-chloro-2-iodobenzene (35 mmol), 289 mg of palladium(II) acetate (1.3 mmol), 1.27 mL of tri-tert-butylphosphine (2.6 mmol), 6.2 g of sodium tert-butoxide (64 mmol), and 160 mL of o-xylene into a reaction vessel, the mixture was stirred for 2 hours at 160℃. After completion of the reaction, the reaction product was cooled to room temperature, and then was extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. Thereafter, the resulting product was purified by column chromatography to obtain 3.4 g of compound 1-3 (29 %).
4) Preparation of compound
1-4
After introducing 3.4 g of compound 1-3 (9.2 mmol), 1 g of palladium(II) acetate (4.6 mmol), 4.3 mL of tri-tert-butylphosphine (9.2 mmol), 12 g of cesium carbonate (36.8 mmol), and 60 mL of o-xylene into a reaction vessel, the mixture was stirred for 2 hours at 160℃. After completion of the reaction, the reaction product was cooled to room temperature, and then was extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. Thereafter, the resulting product was purified by column chromatography to obtain 1.2 g of compound 1-4 (40 %).
5) Preparation of compound
2-1
After introducing 10 g of compound B (31 mmol), 13.2 g of 1-bromo-4-iodobenzene (46 mmol), 855 mg of tris(dibenzylideneacetone)dipalladium(0) (0.9 mmol), 757 mg of tri(o-tolyl)phosphine (2.5 mmol), 6 g of sodium tert-butoxide (62 mmol), and 310 mL of toluene into a reaction vessel, the mixture was stirred for 4 hours at 120℃. After completion of the reaction, the reaction product was cooled to room temperature, and then was extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. Thereafter, the resulting product was purified by column chromatography to obtain 7 g of compound 2-1 (47 %).
6) Preparation of compound
C-73
After introducing 2.7 g of compound 1-4 (8.1 mmol), 4.6 g of compound 2-1 (9.7 mmol), 223 mg of tris(dibenzylideneacetone)dipalladium(0) (0.2 mmol), 198 mg of tri(o-tolyl)phosphine (0.6 mmol), 1.6 g of sodium tert-butoxide (16 mmol), and 80 mL of toluene into a reaction vessel, the mixture was stirred for 2 hours at 120℃. After completion of the reaction, the reaction product was cooled to room temperature, and then was extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. Thereafter, the resulting product was purified by column chromatography to obtain 4 g of compound C-73 (61 %).
Example 2: Preparation of compound C-7
After introducing 3.1 g of compound 1-4 (9.3 mmol), which was prepared by the same method as in Example 1, 2.6 g of 3-bromo-1,1'-biphenyl (11.2 mmol), 256 mg of tris(dibenzylideneacetone)dipalladium(0) (0.28 mmol), 227 mg of tri(o-tolyl)phosphine (0.74 mmol), 1.8 g of sodium tert-butoxide (18.6 mmol), and 93 mL of toluene into a reaction vessel, the mixture was stirred for 3 hours at 120℃. After completion of the reaction, the reaction product was cooled to room temperature, and then was extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. Thereafter, the resulting product was purified by column chromatography to obtain 2.8 g of compound C-7 (62 %).
Example 3: Preparation of compound C-91
After introducing 3.5 g of compound 1-4 (10.5 mmol), which was prepared by the same method as in Example 1, 4.9 g of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (12.6 mmol), 385 mg of tris(dibenzylideneacetone)dipalladium(0) (0.4 mmol), 256 mg of tri(o-tolyl)phosphine (0.8 mmol), 2.0 g of sodium tert-butoxide (21 mmol), and 90 mL of toluene into a reaction vessel, the mixture was stirred for 2 hours at 130℃. After completion of the reaction, the reaction product was cooled to room temperature, and the solvent was removed with a rotary evaporator. Thereafter, the resulting product was purified by column chromatography to obtain 2.4 g of compound C-91 (36 %).
Example 4: Preparation of compound C-92
After introducing 2.7 g of compound 1-4 (8.1 mmol), which was prepared by the same method as in Example 1, 3.9 g of 2-(4-bromo-1-naphthalenyl)-4,6-diphenyl-1,3,5-triazine (8.9 mmol), 300 mg of tris(dibenzylideneacetone)dipalladium(0) (0.3 mmol), 333 mg of 2- dichlorohexylphosphino-2',6'-dimethoxybiphenyl (0.8 mmol), 2.0 g of sodium tert-butoxide (21 mmol), and 41 mL of o-xylene into a reaction vessel, the mixture was stirred for 2 hours at 150℃. After completion of the reaction, the reaction product was cooled to room temperature, and the solvent was removed with a rotary evaporator. Thereafter, the resulting product was purified by column chromatography to obtain 3.0 g of compound C-92 (54 %).
Hereinafter, the luminescent properties of the organic light-emitting diode (OLED) device comprising the compound of the present disclosure will be explained in detail.
Device Example 1-1: Producing an OLED device by a co-evaporation of
first and second host compounds of the present disclosure
An OLED device was produced by using the organic electroluminescent compound according to the present disclosure. A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 30 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer was formed thereon as follows: Compound C-7 and compound B-51 were introduced into two cells of the vacuum vapor depositing apparatus, respectively, as a host, and compound D-1 was introduced into another cell as a dopant. The two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Compound ET-1 and compound EI-1 were then introduced into another two cells, and respectively evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus. Thus, an OLED device was produced. Each of the materials used for producing the OLED device was purified by vacuum sublimation at 10-6 torr.
Comparative Example 1-1: Producing an OLED device comprising a second
host compound as a sole host
An OLED device was produced in the same manner as in Device Example 1-1, except that only compound B-51 was used as a host for a light-emitting layer.
Comparative Example 1-2: Producing an OLED device comprising a
conventional compound as a host
An OLED device was produced in the same manner as in Device Example 1-1, except for the following: A light-emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by using compound CBP as a host and compound D-1 as a dopant; compound Balq was deposited as a hole blocking layer having a thickness of 10 nm; and thereafter, compound ET-1 and compound EI-1 were introduced into another two cells, and evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 25 nm on the light-emitting layer.
The driving voltage, the luminous efficiency, the power efficiency, and the CIE color coordinate at a luminance of 1,000 nits of the OLED devices produced in Device Example 1-1, and Comparative Examples 1-1 and 1-2 are provided in Table 1 below.
Device Example 2-1: Producing an OLED device by a co-evaporation of
first and second host compounds of the present disclosure
An OLED device was produced in the same manner as in Device Examples 1-1, except for using compound D-13 as a dopant, and using the first and second host compounds shown in Table 2 below as a host.
Comparative Example 2-1: Producing an OLED device comprising a second
host compound as a sole host
An OLED device was produced in the same manner as in Device Examples 2-1, except that only compound B-51 was used as a host for a light-emitting layer.
Comparative Example 2-2: Producing an OLED device comprising a
conventional compound as a host
An OLED device was produced in the same manner as in Device Example 2-1, except for the following: A light-emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by using compound CBP as a host and compound D-13 as a dopant; compound Balq was deposited as a hole blocking layer having a thickness of 10 nm; and thereafter, compound ET-1 and compound EI-1 were introduced into another two cells, and evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 25 nm on the light-emitting layer.
The driving voltage, the luminous efficiency, the power efficiency, and the CIE color coordinate at a luminance of 1,000 nits of the OLED devices produced in Device Example 2-1, and Comparative Examples 2-1 and 2-2 are provided in Table 2 below.
Device Example 3-1: Producing an OLED device by an evaporation of a
host compound of the present disclosure
An OLED device was produced in the same manner as in Device Example 1-1, except for the following: Compound C-91 was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-13 was introduced into another cell as a dopant. The dopant was evaporated at a different rate from the host compound, so that the dopant was deposited in a doping amount of 15 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
Comparative Example 3-1: Producing an OLED device comprising a
conventional compound as a host
An OLED device was produced in the same manner as in Device Example 3-1, except for the following: A light-emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by using compound CBP as a host and compound D-13 as a dopant; compound Balq was deposited as a hole blocking layer having a thickness of 10 nm; and thereafter, compound ET-1 and compound EI-1 were introduced into another two cells, and evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 25 nm on the light-emitting layer.
The driving voltage, the luminous efficiency, the power efficiency, and the CIE color coordinate at a luminance of 1,000 nits of the OLED devices produced in Device Example 3-1 and Comparative Example 3-1 are provided in Table 3 below.
Device Example 4-1: Producing an OLED device by an evaporation of a
host compound of the present disclosure
An OLED device was produced in the same manner as in Device Example 1-1, except for the following: Compound C-91 was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-74 was introduced into another cell as a dopant. The dopant was evaporated at a different rate from the host compound, so that the dopant was deposited in a doping amount of 10 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
Comparative Example 4-1: Producing an OLED device comprising a
conventional compound as a host
An OLED device was produced in the same manner as in Device Example 4-1, except for the following: A light-emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by using compound CBP as a host and compound D-74 as a dopant; compound Balq was deposited as a hole blocking layer having a thickness of 10 nm; and thereafter, compound ET-1 and compound EI-1 were introduced into another two cells, and evaporated at a rate of 4:6 to form an electron transport layer having a thickness of 25 nm on the light-emitting layer.
The driving voltage, the luminous efficiency, the power efficiency, and the CIE color coordinate based on 10 mA/cm2 of the OLED devices produced in Device Example 4-1 and Comparative Example 4-1 are provided in Table 4 below.
From Tables 1 to 4 above, it can be seen that the OLED device comprising the compound of the present disclosure as a host not only has excellent luminance property, but also improved power consumption by lowering the driving voltage and increasing luminous and power efficiencies, compared to the OLED device using conventional luminescent material.
Comparative Example 5-1: Producing a blue light-emitting OLED device
not comprising an electron buffer layer
An OLED device was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to 10-7 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming the first hole injection layer having a thickness of 60 nm on the ITO substrate. Compound HI-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming the second hole injection layer having a thickness of 5 nm on the first hole injection layer. Compound HT-1 was introduced into another cell of the vacuum vapor deposition apparatus. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming the first hole transport layer having a thickness of 20 nm on the second hole injection layer. Compound HT-3 was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming the second hole transport layer having a thickness of 5 nm on the first hole transport layer. After forming the hole injection layers and the hole transport layers, a light-emitting layer was then deposited as follows. Compound BH-1 as a host was introduced into one cell of the vacuum vapor deposition apparatus and compound BD-1 as a dopant was introduced into another cell of the apparatus. The two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 2 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 20 nm on the second hole transport layer. Next, compound ET-2 as an electron transport material was introduced into one cell of the vacuum vapor deposition apparatus, and compound EI-1 was introduced into another cell of the vacuum vapor deposition apparatus. The two materials were evaporated at the same rate and doped in a doping amount of 50 wt%, respectively, to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10-6 torr.
Device Examples 5-1 and 5-2: Producing a blue light-emitting OLED
device comprising the compound of the present disclosure as an
electron buffer material
An OLED device was produced in the same manner as in Comparative Example 5-1, except that the thickness of an electron transport layer was reduced to 25 nm and an electron buffer layer having a thickness of 5 nm was inserted between the light-emitting layer and the electron transport layer.
The driving voltage, the luminous efficiency, and the CIE color coordinate at a luminance of 1,000 nits of the OLED devices produced in Comparative Example 5-1 and Device Examples 5-1 and 5-2 are provided in Table 5 below.
From Table 5 above, it can be seen that the OLED device comprising the compound of the present disclosure as an electron buffer material improves the power consumption by lowering the driving voltage and increasing luminous efficiency, compared to the OLED device not comprising an electron buffer material.
The compounds used in the Device Examples and the Comparative Examples are provided in Table 6 below.
Claims (10)
- An organic electroluminescent compound represented by the following formula 1:
whereinY represents S, O or NR5;R1 to R5, each independently, represent deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or are linked to adjacent R1 to R5 to form a substituted or unsubstituted, mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P;a, b and d, each independently, represent an integer of 0 to 4, c represents an integer of 0 to 3; where if a to d, each independently, represent an integer of 2 or more, each of R1 to R4 may be the same or different; andwith the proviso, when Y represents NR5 and a represents 2, two R1 are not fused with the aryl ring to which they are attached to form a carbazole ring. - The organic electroluminescent compound according to claim 1, wherein the substituents of the substituted (C1-C30)alkyl, the substituted (C6-C30)aryl, the substituted (3- to 30-membered)heteroaryl, the substituted (C3-C30)cycloalkyl, the substituted (C1-C30)alkoxy, the substituted tri(C1-C30)alkylsilyl, the substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the substituted tri(C6-C30)arylsilyl, the substituted mono- or di- (C1-C30)alkylamino, the substituted mono- or di- (C6-C30)arylamino, the substituted (C1-C30)alkyl(C6-C30)arylamino, and the substituted mono- or polycyclic, (C3-C30) alicyclic or aromatic ring, or the combination thereof, in R1 to R5, each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (5- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl; a (C6-C30)aryl unsubstituted or substituted with a (5- to 30-membered)heteroaryl; a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di- (C1-C30)alkylamino; a mono- or di- (C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl.
- The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by the following formula 2:
whereinR1 to R4, each independently, represent a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or a substituted or unsubstituted di(C6-C25)arylamino; or are linked to adjacent R1 to R4, respectively, to form a substituted or unsubstituted, mono- or polycyclic, (C5-C25) aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;R5 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 25-membered)heteroaryl;the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P;a to d are as defined in claim 1; andwith the proviso, when a represents 2, two R1 are not fused with the aryl ring to which they are attached to form a carbazole ring. - The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by the following formula 3:
whereinR1 to R4, each independently, represent a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or a substituted or unsubstituted di(C6-C25)arylamino; or are linked to adjacent R1 to R4, respectively, to form a substituted or unsubstituted, mono- or polycyclic, (C5-C25) aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P; anda to d are as defined in claim 1. - The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by the following formula 4:
whereinR1 to R4, each independently, represent a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or a substituted or unsubstituted di(C6-C25)arylamino; or are linked to adjacent R1 to R4, respectively, to form a substituted or unsubstituted, mono- or polycyclic, (C5-C25) aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P; anda to d are as defined in claim 1. - The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
- An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1.
- The organic electroluminescent material according to claim 7, wherein the organic electroluminescent material is a host material or an electron buffer material.
- The organic electroluminescent material according to claim 7, wherein the organic electroluminescent material is a host material comprising at least one of a first host compound and at least one of a second host compound, wherein the first host compound comprises the compound represented by the formula 1, and wherein the second host compound comprises the compound represented by the following formula 5:
whereinMa represents a substituted or unsubstituted nitrogen-containing (5- to 30-membered)heteroaryl;La represents a single bond, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C6-C30)arylene;one of V and W represents a single bond, and the other of V and W represents any one of NR6, CR7R8, S and O;Xa to Xi, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to adjacent Xa to Xi, respectively, to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;R6 to R8, each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; andthe heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P. - An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15/775,136 US10854824B2 (en) | 2015-11-20 | 2016-11-18 | Organic electroluminescent compound, organic electroluminescent material and organic electroluminescent device comprising the same |
| CN201680063074.7A CN108368120B (en) | 2015-11-20 | 2016-11-18 | Organic electroluminescent compound, organic electroluminescent material and organic electroluminescent device comprising same |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20150162980 | 2015-11-20 | ||
| KR10-2015-0162980 | 2015-11-20 | ||
| KR10-2016-0153209 | 2016-11-17 | ||
| KR1020160153209A KR20170059408A (en) | 2015-11-20 | 2016-11-17 | Organic electroluminescent compound, organic electroluminescent material and organic electroluminescent device comprising the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2017086729A1 true WO2017086729A1 (en) | 2017-05-26 |
Family
ID=58719038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2016/013314 WO2017086729A1 (en) | 2015-11-20 | 2016-11-18 | Organic electroluminescent compound, organic electroluminescent material and organic electroluminescent device comprising the same |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN108368120B (en) |
| WO (1) | WO2017086729A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200107836A (en) | 2019-03-07 | 2020-09-16 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound and organic electroluminescent material comprising the same, and organic electroluminescent device |
| WO2024056625A1 (en) * | 2022-09-15 | 2024-03-21 | Merck Patent Gmbh | Method for producing materials for use in electronic devices |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015093813A2 (en) * | 2013-12-17 | 2015-06-25 | 주식회사 두산 | Organic compound, and organic electroluminescent device comprising same |
-
2016
- 2016-11-18 WO PCT/KR2016/013314 patent/WO2017086729A1/en active Application Filing
- 2016-11-18 CN CN201680063074.7A patent/CN108368120B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015093813A2 (en) * | 2013-12-17 | 2015-06-25 | 주식회사 두산 | Organic compound, and organic electroluminescent device comprising same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200107836A (en) | 2019-03-07 | 2020-09-16 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound and organic electroluminescent material comprising the same, and organic electroluminescent device |
| WO2024056625A1 (en) * | 2022-09-15 | 2024-03-21 | Merck Patent Gmbh | Method for producing materials for use in electronic devices |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108368120A (en) | 2018-08-03 |
| CN108368120B (en) | 2022-02-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3494117A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2015037965A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| WO2018021841A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2015084021A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| WO2018151520A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2015084114A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2015099485A1 (en) | An organic electroluminescent compound and an organic electroluminescent device comprising the same | |
| WO2015012618A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2013109045A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2013180478A1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
| EP2828264A1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
| WO2015099486A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| WO2014196805A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| EP3201200A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| EP3563437A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| EP3177628A1 (en) | Organic electroluminescent compounds and organic electroluminescent devices comprising the same | |
| WO2018124697A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| EP3386987A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| EP3189035A1 (en) | A hole transport material and an organic electroluminescent device comprising the same | |
| WO2014200244A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| WO2016021989A1 (en) | Organic electroluminescent compounds and organic electroluminescent devices comprising the same | |
| WO2014104704A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| WO2016052962A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2017095156A1 (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| EP3152197A1 (en) | An organic electroluminescent compound and an organic electroluminescent device comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 16866681 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 16866681 Country of ref document: EP Kind code of ref document: A1 |