KR102458681B1 - 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자 - Google Patents
헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자 Download PDFInfo
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- KR102458681B1 KR102458681B1 KR1020170048532A KR20170048532A KR102458681B1 KR 102458681 B1 KR102458681 B1 KR 102458681B1 KR 1020170048532 A KR1020170048532 A KR 1020170048532A KR 20170048532 A KR20170048532 A KR 20170048532A KR 102458681 B1 KR102458681 B1 KR 102458681B1
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 49
- -1 cya No group Chemical group 0.000 claims description 231
- 239000010410 layer Substances 0.000 claims description 205
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 106
- 125000003118 aryl group Chemical group 0.000 claims description 100
- 150000001875 compounds Chemical class 0.000 claims description 71
- 229910052805 deuterium Inorganic materials 0.000 claims description 71
- 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 claims description 68
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 67
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 67
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 67
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 66
- 125000001624 naphthyl group Chemical group 0.000 claims description 65
- 125000003367 polycyclic group Chemical group 0.000 claims description 64
- 125000006267 biphenyl group Chemical group 0.000 claims description 58
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 50
- 125000005638 hydrazono group Chemical group 0.000 claims description 50
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 49
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 45
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 45
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 44
- 238000002347 injection Methods 0.000 claims description 42
- 239000007924 injection Substances 0.000 claims description 42
- 230000005525 hole transport Effects 0.000 claims description 41
- 239000002019 doping agent Substances 0.000 claims description 40
- 125000006753 (C1-C60) heteroaryl group Chemical group 0.000 claims description 39
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 39
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 39
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 38
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 38
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 38
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 37
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 125000004076 pyridyl group Chemical group 0.000 claims description 34
- 125000004585 polycyclic heterocycle group Chemical group 0.000 claims description 33
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 32
- 125000002837 carbocyclic group Chemical group 0.000 claims description 32
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 30
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 29
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- 239000012044 organic layer Substances 0.000 claims description 29
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 28
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 28
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 26
- 229910005965 SO 2 Inorganic materials 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000004306 triazinyl group Chemical group 0.000 claims description 24
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 23
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 23
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 22
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
- 230000003111 delayed effect Effects 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 18
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 14
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000011575 calcium Substances 0.000 claims description 9
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 9
- 239000011777 magnesium Substances 0.000 claims description 9
- 239000000872 buffer Substances 0.000 claims description 8
- 230000002950 deficient Effects 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 238000004776 molecular orbital Methods 0.000 claims description 5
- 229910001148 Al-Li alloy Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 3
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 229910006404 SnO 2 Inorganic materials 0.000 claims description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical group [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 2
- 229910001887 tin oxide Inorganic materials 0.000 claims description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 claims description 2
- 125000006757 (C2-C30) heterocyclic group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000000463 material Substances 0.000 description 33
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 32
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 29
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 26
- 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 24
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 22
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 22
- 125000003373 pyrazinyl group Chemical group 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 21
- 229940125904 compound 1 Drugs 0.000 description 21
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 21
- 125000001725 pyrenyl group Chemical group 0.000 description 21
- 229910052783 alkali metal Inorganic materials 0.000 description 20
- 150000001340 alkali metals Chemical class 0.000 description 20
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 19
- 150000001342 alkaline earth metals Chemical class 0.000 description 19
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 19
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 19
- 125000001041 indolyl group Chemical group 0.000 description 19
- 125000001544 thienyl group Chemical group 0.000 description 19
- 125000002541 furyl group Chemical group 0.000 description 18
- 125000001633 hexacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C12)* 0.000 description 18
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 18
- 239000002356 single layer Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 16
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 15
- 229910052761 rare earth metal Inorganic materials 0.000 description 15
- 150000002910 rare earth metals Chemical class 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
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 13
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 12
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 12
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 11
- 125000002883 imidazolyl group Chemical group 0.000 description 11
- 125000000842 isoxazolyl group Chemical group 0.000 description 11
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 11
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 11
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 11
- 125000003226 pyrazolyl group Chemical group 0.000 description 11
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 11
- 125000002098 pyridazinyl group Chemical group 0.000 description 11
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 10
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 10
- 229940125782 compound 2 Drugs 0.000 description 10
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 10
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 10
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 125000005580 triphenylene group Chemical group 0.000 description 10
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 9
- 125000005578 chrysene group Chemical group 0.000 description 9
- 229940126214 compound 3 Drugs 0.000 description 9
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 125000005581 pyrene group Chemical group 0.000 description 9
- 125000006762 (C1-C60) heteroarylene group Chemical group 0.000 description 8
- 125000006761 (C6-C60) arylene group Chemical group 0.000 description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- 150000001339 alkali metal compounds Chemical class 0.000 description 8
- 125000004653 anthracenylene group Chemical group 0.000 description 8
- 125000005566 carbazolylene group Chemical group 0.000 description 8
- 125000005584 chrysenylene group Chemical group 0.000 description 8
- XNKVIGSNRYAOQZ-UHFFFAOYSA-N dibenzofluorene Chemical group C12=CC=CC=C2C2=CC=CC=C2C2=C1CC1=CC=CC=C12 XNKVIGSNRYAOQZ-UHFFFAOYSA-N 0.000 description 8
- 125000005567 fluorenylene group Chemical group 0.000 description 8
- 125000002192 heptalenyl group Chemical group 0.000 description 8
- 125000001786 isothiazolyl group Chemical group 0.000 description 8
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- 125000001715 oxadiazolyl group Chemical group 0.000 description 8
- 125000002971 oxazolyl group Chemical group 0.000 description 8
- MHAUGLFOVCQYNR-UHFFFAOYSA-N pentaphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 MHAUGLFOVCQYNR-UHFFFAOYSA-N 0.000 description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 8
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 8
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- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 7
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000005577 anthracene group Chemical group 0.000 description 7
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 7
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 7
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 7
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- 125000005560 phenanthrenylene group Chemical group 0.000 description 7
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- 125000003831 tetrazolyl group Chemical group 0.000 description 7
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- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 6
- KXZQISAMEOLCJR-UHFFFAOYSA-N 7H-indeno[2,1-a]anthracene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5CC4=CC=C3C2=C1 KXZQISAMEOLCJR-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 125000003828 azulenyl group Chemical group 0.000 description 6
- 229940125851 compound 27 Drugs 0.000 description 6
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 6
- 125000006588 heterocycloalkylene group Chemical group 0.000 description 6
- 125000003427 indacenyl group Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229920000767 polyaniline Polymers 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 5
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 5
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 5
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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Abstract
Description
화합물 |
1H NMR (CDCl3 , 400 MHz) | MS/FAB | |
Found [M+1] |
calc. | ||
1 | 7.31 (d, 2H), 7.27-7.23 (m, 3H), 7.18-7.14 (m, 12H), 6.92 (t, 4H), 1.65 (s, 12H) | 541.33 | 540.23 |
2 | 7.33 (d, 2H), 7.28-7.22 (m, 19H), 7.19 -7.13 (m, 16H), 7.11 (d, 8H), 6.92 (t, 4H) | 789.33 | 788.30 |
3 | 7.47 (d, 8H), 7.41-7.36 (m, 20H), 7.30-7.20 (m, 9H), 7.03 (t, 4H) | 821.27 | 820.25 |
7 | 9.13 (s, 1H), 8.77 (d, 1H), 8.55 (d, 11H), 8.26 (d, 1H), 7.93 (d, 1H), 7.76 (d, 2H), 7.55-7.51 (m, 5H), 7.36-7.32 (m, 3H), 7.20-7.13 (m, 7H), 6.99 (t, 2H), 1.69 (s, 6H) | 576.44 | 575.21 |
8 | 8.54 (d, 1H), 7.93 (d, 1H), 7.76 (d, 4H), 7.52 (d, 1H), 7.36-7.31 (m, 3H), 7.17-7.12 (m, 7H), 6.94 (t, 2H), 1.67 (s, 6H) | 575.11 | 574.22 |
11 | 8.56-8.54 (m, 2H), 8.20 (d, 1H), 7.95 (d, 1H), 7.78-7.70 (m, 5H), 7.67 (s, 1H), 7.57 (d, 1H), 7.52-7.48 (m, 7H), 7.39-7.32 (m, 3H), 7.2-7.15 (m, 3H) | 533.21 | 532.17 |
27 | 7.47-7.40 (m, 12H), 7.37-7.32 (m, 16H), 7.29-7.25 (m, 3H), 7.01 (t, 4H) | 837.41 | 836.23 |
발광층 | 구동전압 (V) |
전류밀도 (㎃/㎠) |
최대양자 효율 (%) |
발광색 | |
실시예 1 | 화합물1 | 4.2 | 5.5 | 20.5 | 청색 |
실시예 2 | 화합물2 | 4.3 | 5.5 | 19.9 | 청색 |
실시예 3 | 화합물3 | 4.4 | 5.5 | 18.8 | 청색 |
실시예 4 | 화합물7 | 3.8 | 5.5 | 21 | 청색 |
실시예 5 | 화합물8 | 3.7 | 5.5 | 22.1 | 청색 |
실시예 6 | 화합물11 | 3.8 | 5.5 | 19.9 | 청색 |
실시예 7 | 화합물27 | 4.4 | 5.5 | 18.9 | 청색 |
비교예1 | BCPO | 4.9 | 5.5 | 14.9 | 청색 |
비교예2 | 비교 화합물 1 | 4.7 | 5.5 | 4.4 | 청색 |
비교예 3 | 비교 화합물 2 | 4.9 | 5.5 | 14.4 | 청색 |
비교예 4 | 비교 화합물 3 | 5.5 | 5.5 | 13.3 | 청색 |
발광층 | 구동전압 (V) |
전류밀도 (㎃/㎠) |
최대 양자 효율 (%) |
발광색 | |
실시예 8 | 화합물 3 | 6.4 | 2 | 22.5 | 청색 |
실시예 9 | 화합물 7 | 6.2 | 2 | 23.9 | 청색 |
실시예 10 | 화합물 8 | 6.3 | 2 | 19.3 | 청색 |
실시예 11 | 화합물 11 | 6.2 | 2 | 22 | 청색 |
비교예5 | DPS | 7.4 | 2 | 16.7 | 청색 |
110: 제1전극
150: 유기층
190: 제2전극
Claims (20)
- 하기 화학식 1로 표시되는 헤테로시클릭 화합물:
<화학식 1>
<화학식 2-1>
<화학식 2-2>
<화학식 3-1>
<화학식 3-2>
상기 화학식 1, 2-1, 2-2, 3-1 및 3-2 중,
X1은 O 또는 S이고,
Ar1 및 Ar2는 서로 독립적으로, 치환 또는 비치환된 방향족 C6-C30카보시클릭 그룹 또는 치환 또는 비치환된 파이 전자 결핍성 함질소 C2-C30헤테로시클릭 그룹 중에서 선택되고,
a1 및 a2는 서로 독립적으로, 0 또는 1이고,
b1 및 b2는 서로 독립적으로, 0 또는 1이고,
상기 a1, a2, b1 및 b2는 a1+b1≥1, a2+b2≥1을 만족하고,
R1 및 R2는 서로 독립적으로, 화학식 2-1로 표시되는 그룹이고,
R3는 화학식 2-2로 표시되는 그룹이고,
A1 내지 A4는 서로 독립적으로, 벤젠 그룹, 피리딘 그룹, 또는 피리미딘 그룹이고,
A5 내지 A8은 서로 독립적으로, 벤젠 그룹, 피리딘 그룹, 또는 피리미딘 그룹이고,
Y1은 단일결합, O, S, SO2, C(R19)(R20) 또는 Si(R19)(R20)이고,
Y2는 단일결합, O, S, SO2, C(R19)(R20), Si(R19)(R20), S(=O)(R19) 또는 S(=O)2(R19)이고,
Y3은 단일결합, O, S, SO2, C(R19)(R20) 또는 Si(R19)(R20)이고,
Y4는 단일결합, O, S, SO2, N(R19), C(R19)(R20), Si(R19)(R20), S(=O)(R19), S(=O)2(R19) 또는 P(=O)(R19)이고,
Y5는 단일결합, O, S, SO2, N(R19), C(R19)(R20), Si(R19)(R20), S(=O)(R19), S(=O)2(R19) 또는 P(=O)(R19)이고,
Y2가 O 또는 S인 경우에, 상기 화학식 2-1로 표시되는 그룹과 상기 화학식 2-2로 표시되는 그룹은 서로 상이하고,
R11 내지 R14는 서로 독립적으로, 화학식 3-1로 표시되는 그룹, 화학식 3-2로 표시되는 그룹, 수소, 중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미디노기, 히드라지노기, 히드라조노기, 치환 또는 비치환된 C1-C60알킬기, 치환 또는 비치환된 C2-C60알케닐기, 치환 또는 비치환된 C2-C60알키닐기, 치환 또는 비치환된 C1-C60알콕시기, 치환 또는 비치환된 C3-C10시클로알킬기, 치환 또는 비치환된 C1-C10헤테로시클로알킬기, 치환 또는 비치환된 C3-C10시클로알케닐기, 치환 또는 비치환된 C1-C10헤테로시클로알케닐기, 치환 또는 비치환된 C6-C60아릴기, 치환 또는 비치환된 C6-C60아릴옥시기, 치환 또는 비치환된 C6-C60아릴티오기, 치환 또는 비치환된 C1-C60헤테로아릴기, 치환 또는 비치환된 1가 비-방향족 축합다환 그룹(substituted or unsubstituted monovalent non-aromatic condensed polycyclic group), 치환 또는 비치환된 1가 비-방향족 헤테로축합다환 그룹(substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group), -S(=O)(Q1) 또는 -P(=O)(Q1)(Q2)이고, 2 이상의 R11이 선택적으로(optionally) 결합하여, 치환 또는 비치환된 C5-C60 카보시클릭 그룹 또는 치환 또는 비치환된 C2-C60 헤테로시클릭 그룹을 형성할 수 있고, 2 이상의 R12가 선택적으로 결합하여, 치환 또는 비치환된 C5-C60 카보시클릭 그룹 또는 치환 또는 비치환된 C2-C60 헤테로시클릭 그룹을 형성할 수 있고, 2 이상의 R13이 선택적으로 결합하여, 치환 또는 비치환된 C5-C60 카보시클릭 그룹 또는 치환 또는 비치환된 C2-C60 헤테로시클릭 그룹을 형성할 수 있고, 2 이상의 R14이 선택적으로 결합하여, 치환 또는 비치환된 C5-C60 카보시클릭 그룹 또는 치환 또는 비치환된 C2-C60 헤테로시클릭 그룹을 형성할 수 있고,
b11 내지 b14는 서로 독립적으로 1 내지 8의 정수 중에서 선택되고,
Y2가 단일결합일 때, R13 및 R14 중 적어도 하나가 화학식 3-1으로 표시되는 그룹 또는 화학식 3-2로 표시되는 그룹이고,
상기 화학식 1 중 -(Ar1)a1-(R1)b1 및 -(Ar2)a2-(R2)b2가 각각 페닐기인 경우에, Y2는 S(=O)(R19) 또는 S(=O)2(R19)이거나, R13 및 R14 중 적어도 하나가 화학식 3-1 또는 화학식 3-2로 표시되는 그룹이고,
R15 내지 R20은 서로 독립적으로, 수소, 중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미디노기, 히드라지노기, 히드라조노기, 치환 또는 비치환된 C1-C60알킬기, 치환 또는 비치환된 C2-C60알케닐기, 치환 또는 비치환된 C2-C60알키닐기, 치환 또는 비치환된 C1-C60알콕시기, 치환 또는 비치환된 C3-C10시클로알킬기, 치환 또는 비치환된 C1-C10헤테로시클로알킬기, 치환 또는 비치환된 C3-C10시클로알케닐기, 치환 또는 비치환된 C1-C10헤테로시클로알케닐기, 치환 또는 비치환된 C6-C60아릴기, 치환 또는 비치환된 C6-C60아릴옥시기, 치환 또는 비치환된 C6-C60아릴티오기, 치환 또는 비치환된 C1-C60헤테로아릴기, 치환 또는 비치환된 1가 비-방향족 축합다환 그룹, 치환 또는 비치환된 1가 비-방향족 헤테로축합다환, -S(=O)(Q1) 및 -P(=O)(Q1)(Q2) 그룹 중에서 선택되고,
b15 내지 b18은 서로 독립적으로 1 내지 8의 정수 중에서 선택되고,
상기 치환된 C5-C60 카보시클릭 그룹, 치환된 C2-C60 헤테로시클릭 그룹 치환된 C1-C60 알킬기, 치환된 C2-C60 알케닐기, 치환된 C2-C60 알키닐기, 치환된 C1-C60 알콕시기, 치환된 C3-C10 시클로알킬기, 치환된 C1-C10 헤테로시클로알킬기, 치환된 C3-C10 시클로알케닐기, 치환된 C1-C10 헤테로시클로알케닐기, 치환된 C6-C60 아릴기, 치환된 C6-C60 아릴옥시기, 치환된 C6-C60 아릴티오기, 치환된 C1-C60 헤테로아릴기, 치환된 1가 비-방향족 축합다환 그룹 및 치환된 1가 비-방향족 헤테로축합다환 그룹의 치환기 중 적어도 하나는,
중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미디노기, 히드라지노기, 히드라조노기, C1-C60알킬기, C2-C60알케닐기, C2-C60알키닐기, C1-C60알콕시기;
중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미디노기, 히드라지노기, 히드라조노기, C3-C10시클로알킬기, C1-C10헤테로시클로알킬기, C3-C10시클로알케닐기, C1-C10헤테로시클로알케닐기, C6-C60아릴기, C6-C60아릴옥시기, C6-C60아릴티오기, C1-C60헤테로아릴기, 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹, -Si(Q11)(Q12)(Q13), -N(Q11)(Q12), -B(Q11)(Q12), -C(=O)(Q11), -S(=O)2(Q11) 및 -P(=O)(Q11)(Q12) 중에서 선택된 적어도 하나로 치환된, C1-C60알킬기, C2-C60알케닐기, C2-C60알키닐기 및 C1-C60알콕시기;
C3-C10시클로알킬기, C1-C10헤테로시클로알킬기, C3-C10시클로알케닐기, C1-C10헤테로시클로알케닐기, C6-C60아릴기, C6-C60아릴옥시기, C6-C60아릴티오기, C1-C60헤테로아릴기, 1가 비-방향족 축합다환 그룹 및 1가 비-방향족 헤테로축합다환 그룹;
중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미디노기, 히드라지노기, 히드라조노기, C1-C60알킬기, C2-C60알케닐기, C2-C60알키닐기, C1-C60알콕시기, C3-C10시클로알킬기, C1-C10헤테로시클로알킬기, C3-C10시클로알케닐기, C1-C10헤테로시클로알케닐기, C6-C60아릴기, C6-C60아릴옥시기, C6-C60아릴티오기, C1-C60헤테로아릴기, 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹, -Si(Q21)(Q22)(Q23), -N(Q21)(Q22), -B(Q21)(Q22), -C(=O)(Q21), -S(=O)2(Q21) 및 -P(=O)(Q21)(Q22) 중에서 선택된 적어도 하나로 치환된, C3-C10시클로알킬기, C1-C10헤테로시클로알킬기, C3-C10시클로알케닐기, C1-C10헤테로시클로알케닐기, C6-C60아릴기, C6-C60아릴옥시기, C6-C60아릴티오기, C1-C60헤테로아릴기, 1가 비-방향족 축합다환 그룹 및 1가 비-방향족 헤테로축합다환 그룹; 및
-Si(Q31)(Q32)(Q33), -N(Q31)(Q32), -B(Q31)(Q32), -C(=O)(Q31), -S(=O)2(Q31) 및 -P(=O)(Q31)(Q32);
중에서 선택되고,
상기 Q1, Q2, Q11 내지 Q13, Q21 내지 Q23 및 Q31 내지 Q33은 서로 독립적으로, 수소, 중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미디노기, 히드라지노기, 히드라조노기, C1-C60알킬기, C2-C60알케닐기, C2-C60알키닐기, C1-C60알콕시기, C3-C10시클로알킬기, C1-C10헤테로시클로알킬기, C3-C10시클로알케닐기, C1-C10헤테로시클로알케닐기, C6-C60아릴기, C1-C60헤테로아릴기, 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹, 비페닐기 및 터페닐기 중에서 선택되고,
*는 이웃하는 원자와의 결합 사이트이다. - 제1항에 있어서, 상기 a1, a2, b1 및 b2는
a1+b1=1 및 a2+b2=1을 만족하는, 헤테로시클릭 화합물. - 제1항에 있어서, 상기 b1 및 b2는
b1+b2=0 또는 b1+b2=1를 만족하는, 헤테로시클릭 화합물. - 제1항에 있어서, 상기 Y2가 O인 경우에, 상기 Y1은 단일결합, S, SO2, C(R19)(R20) 또는 Si(R19)(R20)이고,
상기 Y2가 S인 경우에, 상기 Y1은 단일결합, O, SO2, C(R19)(R20) 또는 Si(R19)(R20)인, 헤테로시클릭 화합물. - 삭제
- 삭제
- 삭제
- 제1항에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 1-1 또는 1-2로 표시되는, 헤테로시클릭 화합물:
<화학식 1-1>
<화학식 1-2>
상기 화학식 1-1 및 1-2 중,
A11, A12, A21, A22, A31 및 A32의 정의는 제1항에서의 A1 내지 A4의 정의와 동일하고,
Y11 및 Y13의 정의는 제1항에서의 Y1의 정의와 동일하고,
Y12는 정의는 제1항에서의 Y2의 정의와 동일하고,
Y11 및 Y12 중 어느 하나가 O인 경우에, 나머지 하나는 O가 아니고,
R101, R102, R111, R112, R121 및 R122의 정의는 제1항에서의 R11 내지 R14의 정의와 동일하고,
b101, b102, b111, b112, b121 및 b122는 서로 독립적으로 1 내지 8의 정수 중에서 선택되고,
X1, Ar1 및 Ar2는 제1항에서 정의된 바와 동일하다. - 제1항에 있어서,
상기 R11 내지 R14는 서로 독립적으로, 화학식 3-1로 표시되는 그룹, 화학식 3-2로 표시되는 그룹, 수소, 중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 메틸기, 에틸기, 프로필기, 이소부틸기, sec-부틸기, ter-부틸기, C1-C20알콕시기, 페닐기, 아크리딜기 및 카바졸기; 및
중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 메틸기, 에틸기, 프로필기, 이소부틸기, sec-부틸기, ter-부틸기 및 C1-C20알콕시기 중에서 선택된 적어도 하나의 치환기로 치환된, 페닐기, 아크리딜기 및 카바졸기; 중에서 선택된. 헤테로시클릭 화합물. - 제10항에 있어서,
상기 R23은 수소, 중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 메틸기, 에틸기, 프로필기, 이소부틸기, sec-부틸기, ter-부틸기, C1-C20알콕시기, 시클로펜틸기, 시클로헥실기, 페닐기, 나프틸기, 플루오레닐기, 피리디닐기, 피리미딜기, 퀴놀리닐기, 이소퀴놀리닐기, 벤조퀴놀리닐기, 나프티리디닐기, 퀴녹살리닐기, 퀴나졸리닐기, 카바졸일기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 비페닐기 및 터페닐기; 및
중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미디노기, 히드라지노기, 히드라조노기, 메틸기, 에틸기, 프로필기, 이소부틸기, sec-부틸기, ter-부틸기, 페닐기, 나프틸기, 플루오레닐기, 카바졸일기, 디벤조퓨라닐기, 디벤조티오페닐기, 비페닐기 및 터페닐기 중에서 선택된 적어도 하나로 치환된, 중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 메틸기, 에틸기, 프로필기, 이소부틸기, sec-부틸기, ter-부틸기, C1-C20알콕시기, 시클로펜틸기, 시클로헥실기, 페닐기, 나프틸기, 플루오레닐기, 피리디닐기, 피리미딜기, 퀴놀리닐기, 이소퀴놀리닐기, 벤조퀴놀리닐기, 나프티리디닐기, 퀴녹살리닐기, 퀴나졸리닐기, 카바졸일기, 트리아지닐기, 디벤조퓨라닐기, 디벤조티오페닐기, 비페닐기 및 터페닐기; 중에서 선택되고,
R21, R22 및 R24 내지 R27은 수소인, 헤테로시클릭 화합물. - 제1항에 있어서,
상기 R15 내지 R20은 서로 독립적으로, 수소, 중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 메틸기, 에틸기, 프로필기, 이소부틸기, sec-부틸기, ter-부틸기, C1-C20알콕시기 및 페닐기; 및
중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 메틸기, 에틸기, 프로필기, 이소부틸기, sec-부틸기, ter-부틸기 및 C1-C20알콕시기 중에서 선택된 적어도 하나의 치환기로 치환된 페닐기; 중에서 선택된. 헤테로시클릭 화합물. - 제1전극;
상기 제1전극에 대향하는 제2전극; 및
상기 제1전극과 상기 제2전극 사이에 개재되고, 발광층을 포함한 유기층;을 포함하고,
상기 제1전극은 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO), 마그네슘(Mg), 은(Ag), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag), 또는 이의 임의의 조합을 포함하고,
상기 제2전극은 리튬(Li), Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, ITO, IZO, 또는 이의 임의의 조합을 포함하고,
상기 유기층은 제1항 내지 제4항 및 제8항 내지 제13항 중 어느 한 항의 헤테로시클릭 화합물을 1종 이상 포함한, 유기 발광 소자. - 제14항에 있어서,
상기 제1전극이 애노드이고,
상기 제2전극이 캐소드이고,
상기 유기층은 상기 제1전극과 상기 발광층 사이에 개재된 정공 수송 영역 및 상기 발광층과 상기 제2전극 사이에 개재된 전자 수송 영역을 더 포함하고,
상기 정공 수송 영역은 정공 주입층, 정공 수송층, 버퍼층, 발광 보조층 및 전자 저지층 중에서 선택된 적어도 하나를 포함하고,
상기 전자 수송 영역은, 정공 저지층, 전자 수송층 및 전자 주입층 중에서 선택된 적어도 하나를 포함한, 유기 발광 소자. - 제14항에 있어서,
상기 발광층에 상기 헤테로시클릭 화합물이 포함되어 있는, 유기 발광 소자. - 제16항에 있어서,
상기 발광층에 포함된 헤테로시클릭 화합물은 호스트이고,
상기 발광층이 인광 도펀트를 더 포함한, 유기 발광 소자. - 제16항에 있어서,
상기 발광층에 포함된 헤테로시클릭 화합물이 지연 형광 도펀트이고, 하기 수식 1을 만족하는, 유기 발광 소자:
<수식 1>
│ED, S1 - ED, T1│ ≤ 0.3 eV
상기 수식 1 중
ED, S1는 상기 지연 형광 도펀트의 일중항 에너지(eV)이고
ED, T1는 상기 지연 형광 도펀트의 삼중항 에너지(eV)이다. - 제16항에 있어서,
상기 발광층에 포함된 헤테로시클릭 화합물이 지연 형광 도펀트이고,
상기 발광층이 호스트를 더 포함하고,
상기 지연 형광 도펀트 및 상기 호스트는 하기 수식 2 또는 3을 만족하는, 유기 발광 소자:
<수식 2>
│EH, HOMO - ED, HOMO│≤ 0.5 eV
<수식 3>
│EH, LUMO - ED, LUMO│≤ 0.5 eV
상기 수식 2 및 3 중
EH, HOMO는 상기 호스트의 최고준위 점유 분자궤도 레벨이고,
ED, HOMO는 상기 도펀트의 최고준위 점유 분자궤도 레벨이고,
EH, LUMO는 상기 호스트의 최저준위 점유 분자궤도 레벨이고,
ED, LUMO는 상기 도펀트의 최저준위 점유 분자궤도 레벨이다.
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US15/788,605 US11145823B2 (en) | 2017-04-14 | 2017-10-19 | Heterocyclic compound and organic light emitting device including the same |
EP21170572.8A EP3879593A1 (en) | 2017-04-14 | 2018-04-10 | Heterocycle substituted phosphorous derivatives and organic light-emitting device including the same |
EP18166673.6A EP3389109B1 (en) | 2017-04-14 | 2018-04-10 | Heterocycle substituted phosphorous derivatives and organic light-emitting device including the same |
CN201810324263.6A CN108727429B (zh) | 2017-04-14 | 2018-04-12 | 杂环化合物和包括该杂环化合物的有机发光器件 |
US17/489,613 US12069948B2 (en) | 2017-04-14 | 2021-09-29 | Heterocyclic compound and organic light-emitting device including the same |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015201463A (ja) * | 2012-08-07 | 2015-11-12 | 国立大学法人九州大学 | 有機エレクトロルミネッセンス素子、並びに、それに用いる化合物、キャリア輸送材料およびホスト材料 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004200141A (ja) * | 2002-10-24 | 2004-07-15 | Toyota Industries Corp | 有機el素子 |
TW200903877A (en) * | 2007-07-10 | 2009-01-16 | Idemitsu Kosan Co | Material for organic electroluminescence device and organic electroluminescence device utilizing the same |
JP5808252B2 (ja) * | 2009-01-07 | 2015-11-10 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | カルバゾール、ジベンゾフラン、ジベンゾチオフェンおよびジベンゾホスホールから選択されたシリル置換およびヘテロ原子置換された化合物および該化合物の有機エレクトロニクスへの使用 |
JP5495578B2 (ja) | 2009-02-13 | 2014-05-21 | ケミプロ化成株式会社 | 新規なトリアリールホスフィンオキシド誘導体、それよりなるホスト材料およびそれを含む有機エレクトロルミネッセンス素子 |
TWI466980B (zh) | 2009-02-27 | 2015-01-01 | Nippon Steel & Sumikin Chem Co | Organic electroluminescent elements |
DE102010005697A1 (de) | 2010-01-25 | 2011-07-28 | Merck Patent GmbH, 64293 | Verbindungen für elektronische Vorrichtungen |
US10177312B2 (en) | 2011-05-05 | 2019-01-08 | Merck Patent Gmbh | Compounds for electronic devices |
WO2015115530A1 (ja) * | 2014-01-31 | 2015-08-06 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 |
EP2933849A1 (de) * | 2014-04-15 | 2015-10-21 | cynora GmbH | Hostmaterialien für OLEDs |
CN104212439B (zh) * | 2014-08-15 | 2016-08-17 | 南京邮电大学 | 一种含n-p=s共振结构的光电功能材料、制备方法及应用 |
KR101813761B1 (ko) * | 2014-10-17 | 2018-01-30 | 주식회사 엘지화학 | 신규한 유기 화합물 및 이를 포함하는 유기 발광 소자 |
US10700289B2 (en) * | 2015-03-05 | 2020-06-30 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting element comprising same |
CN107406471B (zh) | 2015-03-05 | 2020-06-02 | 株式会社Lg化学 | 杂环化合物和包含其的有机发光元件 |
KR102458681B1 (ko) * | 2017-04-14 | 2022-10-26 | 삼성디스플레이 주식회사 | 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자 |
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---|---|---|---|---|
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